Hey Founder,

You’ll look back and realize: You didn’t fail. You just never actually tried. Parachutes are for quitters. But most founders don’t bail with a dramatic exit. They drift. Half-loops. Half-commits. All noise. It feels like action. It’s not. Let’s fix that.

You half-execute. Test instead of commit. 
Cold email campaign with no replies? Failed channel. 
Fumbled pitch? Market doesn't work. 
Meanwhile, that email in your inbox, unanswered. That's not nothing. It's THE thing.

You can call it learning mode, but really, it's just avoiding the fact that focus is harder than motion.

As much as you might like the “fail fast” mantra. Most founders aren’t failing fast... they’re failing vague.

Taking one shot, getting no signal, and moving on as if it were a real test isn't iteration. It's lack of pressure. The founder's version of ghosting themselves. Literally f'ing yourself over for no reason.

Most founders, at some point, discover some version of the OODA loop: 
Observe. Orient. Decide. Act.

An epic decision model and the de-facto agile approach.

OODA was built for VUCA environments: Volatile, uncertain, complex, ambiguous. Sound familiar? That’s you.

I live by OODA. Epic in the chaos. The blueprint of how to move fast when so much around you is unknown (and moving).

Learn fast. Iterate fast. Move fast. 
It’s true. The fastest team to learn wins. So surely that’s the loop?

We build a thing, we release a thing, we see how people are using the thing, we learn a thing, we tweak the thing we built and voilà, we’re an agile, rapid iteration, high-falooting startup.

And it’s exactly where you see the stall. Because you think that’s the whole game. Watch, tweak, ship. Watch, tweak, ship. Infinite loop.

No question it’s rapid iteration… but not applying any real pressure.

Most founders are pretty amazing about deciding what to do, but they don’t target. They act without assessing, launch without pressing, and test without tracking. So they never truly learn. It feels like action, but, again, it's just noise.

You think you’re executing, it’s more like circling. It feels like forward motion, even momentum. It feels like you are doing your job. You’re not quitting. This is building, you are working, things are being done. Until you look at the cumulative needle movement and realize you’re not where you want to be.

It’s the difference between adaptability and targeting. OODA is phase one. Kill Chain is what comes next.

This also isn’t about skipping discovery. No one is shackling your founder creativity. Do the chaotic exploration. I live by the rule that you must only do what matters, but you don’t know what matters, so do everything.

Try everything because the signals are weak. You don’t know your moment yet. But when you find the thing that might work… the prospect that clicks, the user that stays, the vertical that opens, something real, some signal - you HAVE to stop circling and start locking in.

You have to draw a line, THE line, between exploration and commitment and in doing so the fail fast metaphor starts to break.

Because OODA is about speed. And speed without precision is just chaos in motion.

You don’t need a funnel. You need a scope.

There’s a concept borrowed from the military called the kill chain. Sounds aggressive, ignore the name, there is no kill, nor chain.

It’s about finishing the job and the mindset to doing it. You don’t just spot a target. You lock in. You track. You follow through. You finish. (You confirm it’s finished)

The technical name rolls right off the tongue... F2T2EA: Find, Fix, Track, Target, Engage, Assess.

OODA is designed for fluidity, the kill chain is designed for completion. Completion is about eliminating randomness. Ruthless and deliberate steps that force focus.

Am I asking you to slow down. Nope. Kill chain isn't about speed, it's about depth. Getting further in three months with one channel done with precision than six months with six channels done halfway. But, you should do six channels, in three months, all the way, because, you know, #foundermode.

<ul>
<li>Find: Who actually matters?</li>
<li>Fix: Where are they, and what are they doing right now?</li>
<li>Track: What signal are they giving you?</li>
<li>Target: What’s the most precise entry point?</li>
<li>Engage: What’s your ask? What are you trying to unlock?</li>
<li>Assess: Did it work? If not, why?</li>
</ul>

The great thing about F2T2EA is that if it didn’t work, you did it wrong. You didn’t complete. You skipped a step. Probably the annoying, hard, unfun one, the not sexy, easy, or fast one...

It’s slow. It’s uncomfortable. It’s pressure. That’s the point. That's the THING!

F2T2EA reframes founder sales as signal acquisition, not pitch delivery.

I’ve got a founder who sent 380 highly targeted investor emails. Cold. Across multiple channels. He kept detailed notes, signals, next steps. Relentless. I watched him F2T2EA a $4.5M round. It wasn’t magic. It was targeting. Precision. Completion. And, the willingness to just do the f’n work.

Work that most founders do as spray-and-pray because it’s easy and you can say to yourself that you did a thing. Kill chain is the discipline.

Not to repeat, but… You didn’t fail. You just never actually tried.

So maybe, ask yourself:

Did I lock in? Did I track signal? Did I engage with purpose? Did I run the full cycle? Did I stay in it long enough to actually learn something?

Or did I do just enough to say I tried?

Don’t die in the gap between “we did the thing” and “we did it with precision.”

No points for pointing your scope in the right direction. Build the kill chain. (without the kill, or chain)

So don’t just move fast, move precisely, build pressure over time. Know exactly what you’re after and don’t flinch when it gets uncomfortable.

You don’t need a funnel. You need a scope.

If I can be of service, feel free to grab time.

LFG. — James

Most founders don’t fail — they drift. Learn how OODA leads to precision with F2T2EA: a kill chain mindset to stop circling and start executing.

Startup Founders: Build a Kill Chain, Not a Funnel

Startup Kill Chain: Move from OODA to Precision Execution

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StartUp Founders: Build a K*ll Chain, Not a Funnel

Hey Reader,Your startup exists in multiple realities simultaneously. You see a unicorn. They see a horse with an ice cream cone stuck to its head.Same startup. Different realities. That gap between perceptions is where founders live every day — the space between what is and what's perceived.The investor who squints at your deck and diagnoses the wrong problem. The advisor who actually knows what's holding you back. The prospect who can't see why your solution matters. The team member who's certain why that feature missed the mark.All looking at the same data you are. All seeing something completely different.It's obviously just a communication problem. If only you explained it better. If only you highlighted the right metrics. If only you told the story differently.It's not a you problem. Well... it is you. It's just you and everyone else.It's this gap between truth and perception. That forces you to recognize you are not only building a product but also building perception infrastructure.<h3>The Reality Construction Site</h3>The journey founders often have to find out for themselves, through long painful cycles, is that it’s not objective. Reality is constructed in real time through emotions, assumptions, timing, fear, bias, memory, noise, and ego.Reality isn’t a fact. It’s a negotiation. It's a mirror. Everyone sees their own reflection. And everyone is convinced that their reflection is the actual room.This isn’t a love letter to you being misunderstood. It’s the opposite. A wake-up call to the universal truth that perception isn’t reality for anyone. The most dangerous distortion isn’t what others might miss. It’s what you miss.A few times a year some college kid emails me about their dinner recommendation app: “We can’t decide where to eat. We end up at the same place. So let’s build an app that makes shared recommendations and splits the check.”They’re not wrong. The problem feels real. But they’re solving the wrong thing. It’s not a discovery problem. It’s decision fatigue. It’s social inertia. It’s the Paradox of Choice. The same conversation I have in my house on a nightly basis.Everyone in their group agrees the app makes sense. It doesn’t.Consensus ≠ reality Perceived utility ≠ usage.<h3>The Perception Chasm</h3>The 2015 dress photo that went viral because some people saw it as blue and black, while others saw it was white and gold. Same image. Different perceptions. It’s literally the perfect metaphor for the founder experience.The pixels didn’t change. The data didn’t lie. But the reality each person experienced was fundamentally different.Your startup is the dress. Your metrics are the pixels.Perception isn’t passive. It’s active. We don’t just receive information. We construct it based on our past experiences, current needs, and future fears. (NOISE)Your customers do it. Your investors do it. Your team does it. YOU DO IT.Think about the last time someone seemed rude, didn’t hold the door or say thank you. Maybe they just got shitty news, lost in their own crisis? Maybe their internal reality is so f'd they didn’t even see you.It’s rarely personal, but there you are building an entire narrative around it. It wasn’t about you. It rarely is. Main character energy!A founder I coach built an AI tool that cuts proposal creation time by 70% for a very specific use case. The win rate for the few clients using it? Insane. Undeniable.Yet still, prospects and investors reflexively ask: “What about ChatGPT?” There’s no amount of explaining that can bridge that gap. He has to find people who can see what he sees, until he has enough of them, to change what they see.<h3>The Real Job</h3>You think you’re building product. You are, go do that. But also you’re building perception infrastructure.Every metric, milestone, market move. It’s not just about what is. It’s about how it’s seen, heard, and understood.It's more than just shipping features. It's narrating, framing, and managing signal distortion in real time.Instead of telling people what to think, you have to create experiences that lead to the right conclusions:<ul><li>Instead of assuming one big launch will change everything, create multiple moments of truth</li><li>Instead of hoping the right people will see what you see, engineer revelation moments</li><li>Instead of explaining complexity, create simple entry points that make the problem visceral</li></ul><h3>The Cognitive Tightrope</h3>But what about your own distortion?<blockquote>Disclaimer: Clever words courtesy of a clever friend:</blockquote>This is where it gets neurologically painful. The cognitive dissonance that keeps you up at night because you must simultaneously:<ul><li>Maintain conviction in your vision when others don’t see it</li><li>Question your own perception when it might be misleading you</li></ul>It requires holding two contradictory thoughts in your mind every single day:<ul><li>I’m right about this thing everyone else is missing.</li><li>I might be missing something everyone else sees.</li></ul>And that second thought inevitably spirals into… What if I’m the one who’s wrong? What if I’m the delusional founder seeing patterns that just aren’t there?This isn’t just hard. It’s against our biological wiring. The human brain desperately wants cognitive consistency, not contradiction.So how do you do both? Who knows. Maybe a truth-seeking machine.<ul><li>Create systems that test your perceptions against reality, not opinions</li><li>Find people who will tell you when your baby is ugly, but also when it’s beautiful</li><li>Learn to distinguish signal from noise in yourself as rigorously as you do in your metrics</li></ul>You have to build frameworks that make this navigation possible.<h3>The Hidden Advantage</h3>The gap between reality and perception isn’t a bug, like everything, it’s a feature!!If everyone could immediately see and understand your vision exactly as you do, it probably wouldn’t be that innovative. The perception gap is both your greatest frustration and your greatest competitive advantage.Truth isn’t obvious. Signal isn’t clean. Reality is not consensus.But when you find those people who see the dress the same way you do? Those are your early adopters. Your true believers. Your aligned investors. They’re the ones who will help you build a reality where everyone else starts to see it too.Your job isn’t just to build something great. It’s to make its greatness perceivable. Master the art of bridging the perception gap.If this is you, I can probably help build that path within the hour. If I can be of service, feel free to grab time.LFG. — James

Founders must navigate the brutal gap between reality and perception — building both a product and the infrastructure of belief. Here's how to survive it.

Reality Construction: The Perception Gap Every Startup Faces

Founders: Build Reality Construction, Not Just Product

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Reality Construction: The Perception Gap

Startups: Build Reality, Not Just Product

Hey Reader,
One of the things you only discover by being a founder is that... You never arrive. The goal posts always move.
We know this. Build the product, no time to celebrate, now you need a customer. Sign the customer, no time to celebrate, now you need to fix the bugs. Fix the bugs, no time to celebrate, now you have to keep your customers. It's always "just one more thing."
Perhaps my fave way of explaining it, is as a founder you are always standing on the edge of a cliff, when something great happens you are allowed to take 2 steps back, when you do, someone then pushes you back to the edge.
Nothing you do at any single step is ever enough. Thats a feature, not a bug :)
This isn't a startup thing. It's not even new.
This exact feeling of being in motion but never arriving is 2,500 years old! It's called Zeno's Dichotomy Paradox.
Zeno argued: in order to reach a destination, you must first get halfway there. Then halfway again. Then halfway again. And so on.
Which means: you're always closing the gap… but never fully arriving.
You're always getting closer, but it never feels like enough. Welcome to startups. Sound familiar?!
To founders? It's a description of startup life.
You're always moving. You're always improving. You're always almost there.
But you never actually land. Because the minute you do, a new gap opens up in front of you.
Ask any founder who has done it before, there's a particular kind of exhaustion that sets in around year three. It's not the adrenaline wearing off. It's deeper. More existential. It's the staring at the ceiling, asking yourself: "Will it always feel like this?" kind of feeling.
You've hit your milestones. You've grown. You've raised some money. Somehow, you still feel like you're scrambling. Still halfway.
Your friends with "normal jobs" are buying houses, taking vacations, talking about the stock market! Meanwhile, you're on your third "this is our breakout year" speech to the team.
In private? You wonder if the finish line is actually any closer.
This isn't failure. This is Zeno's revenge.
So why is this a newsletter? Because this messes with founders, especially first-timers because you were told the journey had stages:
Idea → MVP → PMF → Growth → Scale → Exit
But that's not what it feels like.
It feels like: Idea → Rejection → Slight traction → Confusion → Spike → Churn → Pivot → Repeat
It feels like you're always halfway to product-market fit. One bug away from the product doing what it promises. One feature away from a big customer buying.
Halfway to fundraising. Halfway to clarity. Halfway to feeling like you're finally there.
Again. That's not failure. That's Zeno.
What makes it worse, is the toll compounds. Halfway in year one has a different weight than halfway in year five. The psychological burden gets heavier, not lighter. The cost to your health, your relationships, your sense of self accumulates.
The more you invest, the more time compresses, making every halfway point feel more urgent than the last. It seems to get worse, not better.
The better you get, the more you understand the market, your customers and your vision, the faster the f'n treadmill goes. You never get to enjoy your new pace before it speeds up again.
This is why founder burnout isn't just about hours worked. It's about the perpetual state of almost-but-not-quite. The cognitive load of always being on the edge, never fully arriving.
So maybe, stop trying to arrive?
The trap is thinking there's a "done." A place where it clicks and stays clicked.
There is no end. Just another level of clarity.
You have to learn to stop waiting for that moment. Because it doesn't exist.
Instead, build the muscle to keep moving especially when you're close. Understand how to measure what is the correct amount of "done" right now that enables the immediate goal to be achieved and balacnes time over target.
Close is where doubt creeps in. Where energy dips. Where momentum stalls.
And that's when most founders stop. They mistake the halfway feeling for being stuck instead of seeing it for what it is…. progress with more perspective.
So if, for a second, we agree, there is no mythical arrival moment. You have to weaponize the halfway state.
You have to build decision frameworks knowing the targets will move. Design your personal sustainability differently. Measure progress differently.
The halfway state must become your competitive advantage.
While others are waiting to feel like a goal has arrived or some "made it" moment before making big bets and bold moves, great founders operate from the understanding that bold moves only happen while standing on that cliff edge, not from some imaginary solid ground.
You have to embrace perpetual incompleteness, not as resignation, but as strategy.
You have to develop rituals that acknowledge progress without halting momentum. Celebrations that honor milestones without pretending they're finish lines.
So yes, on customer 1, 100k ARR, something great, open that bottle of Kirkland whisky, just make sure you are mapping out customer 2 before the burn fades...
Not because you shouldn't enjoy the moment, but because you have learned the rhythm: celebrate briefly, then start the next halfway journey before someone pushes you back to the edge.
Founders have built their entire operating systems around this reality:
So. Design your life for endurance, not sprints & embrace the cliff edge as where genuine innovation happens.... And perhaps most importantly, find ways to derive meaning from the motion itself, not just from arriving at destinations.
There is a trait a lot of founders have after they have done this a few times, they love the game, more than the destination.... because they see it for what it is.
Because the job isn't to arrive. The job is to build while halfway. The job is to lead while uncertain. The job is to decide on the cliff edge.
Perhaps the job becomes learning to love the vertigo!
So, if you got this far.
You are not behind. You are not lost. You are not stuck. You are just halfway. Again. And again. And again. To learn, adapt, and repeat inside an infinite loop.
The distinction between good founders and great ones isn't that great ones eventually "arrive."
It's that great ones master the art of building while halfway. They turn Zeno's curse into their superpower.
And just when you think you've got a handle on your own halfway state. Someone else looks at the same progress and sees something totally different. Remember the blue/gold dress! Perception is a whole other paradox.
As always, if I can be of service, feel free to <a href="https://cms.startuptoscaleup.com/products/1-hr-start-up-consulting-call" target="_blank">grab</a> time.
LFG.
-- James

Founders never truly arrive - you're always halfway. This isn't failure. It's Zeno's paradox in startup form. Learn how to weaponize this state and turn it into your competitive advantage.

Never Arrive.

Startup Founders: Why You Never Arrive (And Why That's Power)

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StartUp Founders: Never Arrive.

The Founder Cliff Edge: Embrace the Halfway State

Hey Reader,
You don't grow out of selling. You grow through it.
Sales is just concentrated empathy plus action. You've already got both. I hope.
Sales is about deeply understanding someone else's problem (empathy) and caring enough to do something about it (action). That's not "selling" - that's serving with conviction. To not sell it, would be selfish :)
But selling evolves. Early customers buy you. The chaos. The charm. The promise. That's where you thrive.
Later customers? Expect some clarity. Consistency. Confidence. Your messy brilliance won't scale unless it's wrapped in a process. But process cannot exist without deep founder signal.
Even after customer 1, you think your sales role changes, and it kinda does, yes. But your proximity to the sale can't ever disappear.
It just shifts very slightly.
I've hammered the importance of sales in past newsletters. Yes, I'm about to do it again.
There's a difference between redundancy and repetition....
Redundancy is noise. The same thing over and over. Repetition is how we learn. Driving home what matters until it sticks.
Everything has changed in 2025, one truth now matters more than ever:
Investors aren't throwing money at top-line growth anymore. They want.
Stickiness. Retention. Expansion.
They're funding customer obsession over customer acquisition.
The playbook is being rewritten in real time, this is not a "sell more" newsletter. (But also sell more) It's about reframing your relationship with sales as your mind, your investors, your team, try and push you out of it.
So.. Just for a second. Stop with the engineering.
Sell. Before building. While building. After building. Sell.
Get in traffic. If you're early, figure out what you can sell based on the problem you're solving. Solve that.
Scale is great, we all dream of it, sure, we want more than eight people to care. But if eight people care deeply, there's probably an arena behind them.
Make those 8 happy. Do it again. That's the secret to scale. That's it.
And if you're already live, already doing revenue, already pushing real product and thinking this is a message isn't for you? Still no.
You're likely blind to how people drop off. No funnel <a href="https://www.startuptoscaleup.com/newsletter/observability-stack/https://www.startuptoscaleup.com/newsletter/observability-stack/" target="_blank">observability</a>. No clarity on what users do or don't do. I imagine, you likely cannot answer some very simple questions about your users…
If churn is on the dashboard, retention is part of sales too.
But most importantly. You don't get to delegate your way out of sales. You don't get to rebrand as the "product" founder and hide in design systems. You're not done selling.
"I'm not a natural salesperson" / "I'm an introvert" / "I'm an engineer/product person at heart"
I don't care.
Sales isn't about being smooth or extroverted. It's about caring enough about your solution to have the hard conversations. It's about being obsessed enough with the problem to listen for the answers.
The best founders I know are awful at sales, but they care so f'n much, customers get pulled in anyway. The number of meetings I have listened to where the founder fumbles the pitch, misses the point, goes way over time, shows "one more feature" and ignores any form of next steps...
But their obsession is contagious. People buy where the founder is heading.
So stop hiding behind a self-imposed label (or excuse). REMINDER: Sales is just concentrated empathy plus action.
All the way up to a few million in ARR— You know the problem better than anyone. You feel the objections before they're spoken. You know the pitch that's off by 1% before anyone else notices.
So you know the moment you step out of traffic, you start losing signal.
And without signal, your strategy is now storytelling. Your deck gets prettier. But it stops getting truer.
And signal is what gets you past where you are now:
<ul>
<li>Your adjacent SKU</li>
<li>Your next module</li>
<li>Your segmentation unlock</li>
<li>Your upsell pathway</li>
</ul>
I have a billionaire client. Yup. Why would a billionaire founder have me as a coach? Because coaching isn't about teaching. It's about pressure.
Perspective. Pattern recognition. It's about having someone who's not inside the machine but still knows how it runs. Someone who's built. Sold. Shipped. Who can call bullshit without posturing. Who gets it.
That's something that took me a long time to learn, to stop chasing answers and start valuing perspective.
They don't need me to tell them how to build. They need someone who can help them see. He doesn't do 99.8% of the work. But he is as close to the sale as anyone on the team.
In his words: "the comma is in the signals, not the dashboard" - should have him write the newsletter.
The data might tell you what happened but the sale will tell you why.
Founders who stop selling lose the loop that drives the learning, the urgency, the velocity, and perhpas even the conviction.
Selling isn't just about demos and deals. It's about you staying as close as possible to whats real.
Another founder I work with is running top-of-funnel. Strong campaigns. Smart targeting. But hadn't called a single user who signed up and bailed.
Thirty minutes on Zoom. Three real (rather obvious in hindsight) reasons. One change to onboarding. Results changed. That simple.
It's not magic. &gt; Sales is all the way through to retention. &gt; Retention is sales. Expansion is sales. &gt; Sales is the entire lifecycle of customer success.
Sell to get. Sell to retain. Sell to expand. Sell to survive.
Let's frame this for the right now we are all living.
AI is stripping the value out of anything generic, replaceable, or easy to build. Capital efficiency is the new growth. Retention is the new god metric.
I'm watching founders doing $100K+ in MRR struggle to raise. Not because the top-line isn't working. Because the signal isn't.
Not enough stickiness. Not enough usage depth. Not enough retention clarity. A narrative built on momentum and exciting new features doth not lead to moat building.
Investors now want to see customers who aren't just buying but they're staying, expanding, advocating.
Exactly how I opened this email: VCs aren't funding customer acquisition anymore. They're funding customer obsession.
That's sales. In the trenches. Retention-obsessed. Never-ending sales.
Yes, it's hard. Yes, you want to step back. Yes, the team wants you to scale.
But I've seen too many startups stall because the founder tries to "mature" too early. Too quietly. Too comfortably.
And no, selling doesn't always mean money.
It's time. It's attention. It's commitment. It's effort. It's a user showing up to do a thing that matters. Again. And again.
That's value exchange. That's signal gained. That's selling. That's how you test your assumptions in public.
That's it. That's the big secret.
Unless you know. Like actually know. Then ignore me. Kinda.
Guessing doesn't scale. Conversations can.
As always, if I can be of service, feel free to <a href="https://cms.startuptoscaleup.com/products/1-hr-start-up-consulting-call" target="_blank">grab</a> time.
LFG.
-- James

Sales isn't just a founder's task, it's your lifeline to market signals. Investors don't fund acquisition anymore - they fund customer obsession. Here's why you can't delegate your way out.

Sell.

Why Founders Must Stay Close to Sales (Even When They Scale)

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StartUp Founders: Sell

Why Founders Can't Delegate Sales: The Signal You Can't Afford to Lose

Hey Reader,
Your pitch deck promised X. Your roadmap outlined Y. But today, you're building Z. And that's exactly as it should be.
Founders write plans as if startups operate in predictable environments. They don't. They operate in constant chaos.
Planning creates direction. Preparation creates options. You need both, but most founders over-index on the former and under-invest in the latter.
Your plans are fantasies until they collide with reality because the world rarely reacts how you expect....
We've all seen those founders with gantt charts, with detailed dependencies, overly complete notion sites, OKR maps formatted for investors. Looks so impressive, that must be the secret to what a great founder looks like, right?
Nope. When you have zero clue what's around the next corner, it's a waste of f'n time.
Planning assumes you know how everything is going to play out. Predictable, known, like a vacation. This street, this car, this hotel. We can plan because the constructs won't change.
Preparation, however, assumes chaos. And chaos is almost always where the money hides.
📌 Planning is how you want things to go. (structure) 📌 Preparation is how you move through what you can't predict. (resilience)
Preparation is NOT the fallback, it's the entire framework.
Preparation is Pattern Recognition. Prepared founders don't just react faster. They notice faster. The ability to actually see the signals, it's attunement, its training to see the week signals. That's the edge. The compounding.
This isn't about hating plans, i'm NOT making a binary argument: Planning, bad - Preparation, good. You should plan. You need to plan.
Planning is how you reduce unstructured chaos, align the team, and move with intention in the same direction.
This issue is when founders start treating the plan as reality, instead of what it actually is, a best guess.
<div><div>"Luck is what happens when preparation meets opportunity." — Seneca</div></div>
Preparation kicks in as soon as you start executing. It's not a rejection of planning, it's what makes planning useful under pressure.
I'm making this distinction between three related but fundamentally different things: 
<ul>
<li>PLAN: A static tool. A snapshot of what you think might happen.</li>
<li>PLANNING: The process of organizing your thinking to align and get started.</li>
<li>PREPARATION: Your ability to respond, adapt, and capture value when reality shifts.</li>
</ul>
Founders often think they're choosing between planning and winging it. But that's not the real tradeoff. You should plan. You should organize your thinking. Structure is good. Just don't confuse that for being ready.
Planning is how you organize your thinking. Preparation is how you condition your response. Preparation is the muscle that you need to train, the one that really matters.
Plans MUST Break. Always.
Plans rarely survive that first contact with reality. Your investor doesn't actually believe your pitch deck; they just want to see how you think, how you articulate, how you prioritize, how you organize.
You're not building in a controlled environment. You don't have perfect information. You're making a thousand small bets on incomplete data.
So why do so many founders over plan? Because it feels like control.
The illusion of control is more dangerous than the admission of chaos.
Plans also assume some level of linearity that just does not exist.
Great founders know a plan is a hypothesis at best. So yes, have a plan, love a plan, as a baseline. Plan to learn, prepare to adapt.
You Are Not a General. Generals get time to plan. They have intel, resources, chains of command. You have none of that, it's real time, limited cash, limited data, and everyone looking to you for direction.
Plan if you want to feel smart. Prepare if you want to be smart.
What Preparation Actually Looks Like
Preparation doesn't mean you don't have direction. It means you've built enough awareness and flexibility to adjust without chaos.
You still set guardrails on how you make decisions, how you think about your market, what you know, and where you think you're going. And yes, you plan the immediate steps.
But preparation is:
🔥 Your team's ability to hear, sense, pivot, and move. 🔥 Your capacity to adapt without panic. 🔥 Knowing how to respond, not needing to be right.
It's readiness for surprise, the surprise you want, the surprise you are waiting for.
Four Filters I Consistently See....
1. Clarity on how you make decisions. Not what the decision is. Prepared founders don't say, "Here's what we're building next." They say, "Here's how we decide what to build next."
2. A team that acts without waiting for permission. Prepared teams know the mission, the standard, the pace. They ship, fix, and respond before the standup even starts.
3. Feedback loops that actually shift behavior. Data is not collected for data sake or slides. They hear hesitation in a call today and change "something" tonight.
4. Conditioned for chaos, not surprised by it. They expect the weird stuff. The platform crashing. The lead ghosting. The legal curveball. It still hurts. But it doesn't kill.
The Planning vs. Preparation Gap
This isn't theory. The gap between planners and preparers shows up in how founders handle the exact same situations.
Planning is theory. Preparation is muscle memory. And in startups, muscle memory beats theory every time.
So with that....
1. Murphy's Law: "Anything that can go wrong, will go wrong."
The only founders who survive are the ones who expect chaos. Not as a pessimistic worldview, but as a practical reality. They're not surprised by it and it doesn't scare them.
2. The OODA Loop: Observe. Orient. Decide. Act.
Developed for fighter pilots in combat. It's about decision velocity. Planning gives you a script. Preparation gives you speed. You don't need to predict the future. You need to out-decide it.
3. Antifragility: Some things get stronger from disorder.
This is Taleb's concept, and it's perfect for startups. You shouldn't just be able to survive volatility. You should get better from it.
Prepared teams get sharper with each unexpected turn, with each new data point, each failure a stepping stone.
TLDR; Don't just write a plan. Train for the terrain.
As always, if I can be of service, feel free to <a href="https://cms.startuptoscaleup.com/products/1-hr-start-up-consulting-call" target="_blank">grab</a> time.
LFG.
-- James

Planning assumes control. Preparation assumes chaos. Learn why startups need both, but most founders over-index on planning and under-invest in preparation - and how to fix it.

Planning vs Preparation

Planning vs Preparation: Why Startup Founders Need Both

The best customer? The one already searching for what you sell. No cold emails. Just qualified buyers, walking into your funnel by choice. Get a Free SEO Competitor Report to see how your site stacks up.

StartUp Founders: Planning vs Preparation

Why Plans Always Break: The Founder's Guide to Preparation

Hey Reader,
Toxic employees kill companies. Nope. Mediocre employees do.
If you truly, deeply, obsessively care about what you're building… you've probably been called toxic, probably even felt a little toxics.
But there's a world of difference between destructive behavior (toxic) and productive intensity (diva energy).
If caring too much, pushing too hard, and refusing to lower your standards makes someone a diva? Then yeah. Hire more of them.
intensity ≠ toxicity
What people really mean when they say diva is that you cared more than they were comfortable with. Sounds like a "them" problem.
You give a ridiculous number of f's about things most people think don't matter. You argue over details. You obsess over edge cases. You go quiet when the quality's off. You blow up when the standards drop. You push. You demand. You don't let it slide.
You're not toxic. You're obsessed. And obsession makes people uncomfortable. So they label it.
Great founders are rarely easy to work with.
The first diva is always the founder. Your job is to hire the second.
<h2>Stop Confusing Discomfort with Dysfunction</h2>
The people who take your startup from zero to one, like you, are rarely easy to manage.
They dissent. They push. They challenge. They lay it all on the table not to feed their ego, not to be right, not to have an opinion on everything, but to build something better.
Some of the most talented, driven people are the hardest to work with. That intensity often correlates directly with exceptional results. If you let it.
So yeah. Hire the divas who make people uncomfortable. Because it's way easier to say nothing, collect the paycheck, and not challenge the founder during standup.
You don't want passive agreement. You have to fight for aligned obsession.
<ul>
<li>The best people will often make others uncomfortable. They expose mediocrity.</li>
<li>Intensity is contagious. Standards rise when someone refuses to lower theirs.</li>
<li>You are diva 001 and you can't expect your team to care even close to as much as you do, but the best ones, sure do try.</li>
<li>A-players want to work with other A-players, not just nice people who underperform.</li>
</ul>
If you're hiring for comfort, you're cannot be building for impact.
&gt; Giving fucks doesn't make you an asshole. &gt; Not having a safe space to give those fucks? That's what creates one.
<hr>
<h2>Culture Isn't Chill. It's Aligned Obsession.</h2>
People don't burn out from hard work. They burn out from working with people who don't care.
Culture eats strategy for breakfast... only applies when culture means something.
Not free snacks. Not surface-level positivity. Def not "easy to work with."
Real culture is when everyone swims in the same direction, with the same mission. Where standards are upheld. Together.
That kind of culture - one that demands excellence is not comfortable. But nothing great ever comes from comfortable.
So again. You get labeled.
Because great founders, building great teams, don't operate at the same pace or intensity as everyone else. You just have to accept that.
When someone's constantly pushing, challenging, working obsessively. It's not ego. It's ownership. And on the things they see clearly, they're probably not wrong.
<h2>Diva vs. Toxic: The Line Is Simple</h2>
I had a whole section here. Bullet points. Emojis. The works. Deleted it. It's simpler than that:
Toxic people care more about being right. Divas care more about getting it right.
Toxicity shows up in double standards, blame, manipulation, and quiet sabotage. Divas are passionate and loud and animated. But they're passionate, loud and animated for the mission.
What matters is the environment you build. You either enable dissent, passion, and raised voices... or you suppress the very intensity your company needs.
The market doesn't care about team harmony. It cares about whether you ship something that works, scales, and wins. Which ironically requires team harmony.
<div><div>And just to be clear - don't misread this. This isn't "Beast Mode Tech Bro" energy. This is aligned obsession with the mission. And it takes a few quirky, intense traits to manifest it.</div></div>
If you're truly building something great, you won't always be easy. And the people who can keep up with you? They won't be easy either.
Hire the divas. Not the drama. Not the ego. But the ones with unreasonable standards, sharp opinions, and deep conviction.
They'll push your culture forward. They'll make your product better. And they'll hold the line when you're too tired to.
Uncomfortably yours,
As always, if I can be of service, feel free to <a href="https://cms.startuptoscaleup.com/products/1-hr-start-up-consulting-call" target="_blank">grab</a> time.
LFG.
-- James (<a href="https://startingastartup.com" target="_blank">Diva 001</a>)

Culture isn't chill. Culture is aligned obsession. Learn the critical difference between destructive toxic behavior and productive intensity to build a team that pushes boundaries.

Toxic vs. Diva

Startup Culture: Why You Should Hire Divas, Not Toxic People

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Wegic

StartUp Founders: Toxic vs. Diva

Hire for Intensity: Why Obsessed Team Members Drive Startup Success

Hey Reader,
You can only believe in what you don't know. That's why you started. Right?
Every great startup begins as an act of defiance against the existing reality. Not always to change the world. Sometimes, just to make something a bit better.
You see a gap in the market, an edge, a better way. You imagine the future. The users, the traction, the growth, the impact. You see your life on the other side. Ugh. The seduction of possibility.
Every founder starts at zero. Just the idea, a vision and an insane will / insanity to see it through.
In possibility land everything is in play. Every door is open and every outcome is still on the table.
But we know, possible is a drug, one of the best. Your job. Your only job (aside from the other jobs!). To go from possible. To probable. To inevitable.
Possibility is Free. Probability is Earned.
Possibility is safe, its the work before go live, the dreaming, the building, the ideating, the pitch deck, all within the safe zone of not having to prove it.
No risk of being wrong….
Your job is to force probability. We know what this feels like (<a href="https://www.startuptoscaleup.com/newsletter/navigate-the-dip/" target="_blank" class="ck-link" rel="noopener noreferrer" style="color:#fa1e1e">the dip</a>) but you are searching for signals that something is vibing, a yes, a conversion, a dollar, a fan, a follower… Tiny f'n signals. But a signal nonetheless, a signal you can build on.
It's not certainty, but it's no longer just possibility. It's evidence. And that changes everything.
It's still fragile, unclear and probably feels like you are losing the battle. But at least you're in the fight?
Getting Stuck
Getting stuck between possible and probable has predictable patterns, mostly just not doing enough of the hard work, but also, three cognitive traps that sometimes get in the way:
📌 The Einstellung Effect: You keep trying to prove your original idea, instead of adapting to what's actually working. 📌 Survivorship Bias: You only see the overnight success stories, so you think you're failing when things don't explode instantly. 📌 Loss Aversion: You're more afraid of proving your idea wrong than actually making it work.
The failure is not in being wrong, it's because the possibility never started.
Possible: You have a vision, a deck, hopefully an <a href="https://www.startuptoscaleup.com/newsletter/create-lovers-not-users/" target="_blank" class="ck-link" rel="noopener noreferrer" style="color:#fa1e1e">MDP</a>. The evidence is anecdotal at best. It's more "People like the idea" than people throwing $$.
Probable: You have paying customers (unaffiliated). You have some form of retention. People are starting to find you (inbound). People are solving the problem with your solution.
Inevitable: The unit economics kinda work. Referrals exist. You've found a repeatable sales motion. Recruiting is becoming easier. Product works as advertised!
3 Stages: Possibility → Probability → Inevitable
POSSIBILITY: The Art of the Possible
Where every founder starts.
You're selling a future that doesn't exist yet. You're recruiting a team on belief alone. Everything is uncertain. Investors aren't responding. Prospects go quiet. You're posting on LinkedIn and getting three likes.
Selling the future….
And the challenge isn't just external (convincing investors, customers, co-founders). It's internal.
This is where it all starts, and its brutal, lonely, and again… <a href="https://www.startuptoscaleup.com/newsletter/navigate-the-dip/" target="_blank" class="ck-link" rel="noopener noreferrer" style="color:#fa1e1e">the dip</a>.
Because possibility is just about getting started. This is the stage that makes you a founder, this is the hard part (for now).
PROBABILITY: A Glimmer Of Hope
📌 First paying customer. 📌 First user actually using it. 📌 First investor who wires cash.
Actually, it doesn't even need to be any of these. It's a moment the market gives you a real signal, something that validates what you've been saying all along. Not hype. Something real.
Probability starts small, maybe just a few percent. And that's okay. It just has to be enough to know you're on the right path...and not completely delusional.
But probability doesnt happen by accident.
It's execution. It's testing, iterating, fixing. It's listening to your customers again and again until you find what sticks. Its knowing the fastest team to learn wins, its going back to your original assumptions and understanding whats changed, its listening to the nuance of the market….
You are just trying to build a tiny bit of momentum and stay alive while doing it.
INEVITABLE Is A State Not An Outcome
When you know how to get a yes. You know that if you get someone on the phone, they'll say yes. You know that if you do X, Y will happen. You understand the input/output dynamics of your business. You have customers. You have some revenue. But most of all, you have clear signals. You understand exactly what you need to do.
This is when you start thinking that success is inevitable, if you can just execute. Your capability to do the job is now the blocker.
Inevitable doesn't have to mean your ARR exploded, or you own the category, but it does mean the demand is clearly coming in, its a touch overwhelming, and its all very real. You might call it PMF.
That's when the heavy stuff starts. The real work it takes to grow into inevitable. And maintain the sanity to know inevitable is a state of momentum not a finish line.
Fab founders never stop asking what's next, looking down the line, imagining the next SKU, the next growth lever, the next 10x feature.
Staying inevitable is just as hard, perhaps harder than getting there.
Whatever stage you're at, the question is always the same: What's the one action that moves you meaningfully forward?
Now go do that..
As always, if I can be of service, feel free to <a href="https://cms.startuptoscaleup.com/products/1-hr-start-up-consulting-call" target="_blank" class="ck-link" rel="noopener noreferrer" style="color:#fa1e1e">grab</a> time.
LFG.
-- James

Every great startup begins as an act of defiance against reality. Learn how to move from Possibility to Probability to Inevitable success through execution and market validation.

Possible. Probable. Inevitable.

Startup Founders: The Journey from Possible to Inevitable Success

If you're building a company, achieving compliance is critical to proving strong security practices, winning bigger deals, and deepening trust with customers — but can cost you real time and money.

StartUp Founders: Possible. Probable. Inevitable

The Startup Evolution: From Possible to Inevitable

Hey Reader,
The biggest inflection points in your startup won't feel big when they happen. It's the smallest shifts that change everything.
Big Doors Swing on Small Hinges is tied to decisions, actions, and communication.
🚀 The decision that kills your startup won't feel big when you make it. That's what makes it dangerous. 🚀 The decision that changes everything won't feel big either. That's why most founders miss it.
This is the counter-balance to the <a href="https://www.startuptoscaleup.com/newsletter/entropy-wins/" target="_blank" class="ck-link" rel="noopener noreferrer" style="color:#fa1e1e">entropy newsletter</a>. The thousand tiny compromises that don't feel like failure. Until they do.
Entropy = Passive decline. (failure sneaks up on you) Small Hinges = Active momentum. (success sneaks up on everyone else)
Startups don't die because they miss one giant opportunity. They die because they miss a thousand small ones.
This is not a "play small" story, nor is it thinking small, playing it safe, avoiding big swings, not taking moonshots or any other attempt to assign small hinges to small things.
Its about understanding what makes big swings possible. Massive wins are rarely the result of that one heroic, high risk move, its intelligent, strategic, high leverage decisions that stack over time.
The gold medal at the olympics. Thousands of early mornings, restrictive diets, cancelled plans, injuries, and more.
Yes, one big moment can shift everything. One big feature. One big investor. One big customer. One big partner. Sure. Sometimes, the right big swing pays off. Sometimes, it has to. But that's rarely how the big win happens.
I talked about this in <a href="https://www.startuptoscaleup.com/newsletter/monopsony-trap/" target="_blank" class="ck-link" rel="noopener noreferrer" style="color:#fa1e1e">The Monopsony Trap</a>. Chasing it, sometimes works. Most of the time, it bends your company in ways you can't recover from.
It's not the monster client that changes everything. Its the 100's of prospect calls that came beforehand, the rigorous refinement of messaging, the preparation, the pain, the failure, the rejections.
It's not the massive launch that sets you apart. It's the months of planning, researching, organization and the relentless execution on the tiny details that add up over time. Ask anyone who launched on product hunt with 3 days of prep.
The biggest inflection points in a startup rarely feel big in the moment.
Founders Hate Small Hinges :)
We chase big swings instead of small hinges. Big swings feel like progress. Small hinges feel like maintenance.
We know this, I always talk about it. Your (my) brain is wired for dopamine, not results.
The rush, the thrill, the high, of having an epic opportunity - a logo prospect, a media mention, a VC tickle.
Your brain floods with dopamine from the possibility of massive success. Even when the probability is microscopic.
(Now I have next weeks topic - Possibility vs Probability!)
The small, boring, unsexy work that actually moves the needle barely registers. No glory. No rush. No story to tell at founder happy hour.
You know you know this. Marginal gains is a real thing. If you work on your SEO everyday, you will rank higher, you make one small improvement to your customer support program and less customers will need a human. The 1% rule. Make something 1% better every day… do i need to finish this sentence?
The question is whether you have the discipline to know you know this and ignore the dopamine to focus on the small boring, high leverage decisions, every. single. day.
Small Hinge Filter?
Not perfect... but:
1️⃣ Can it be done in a day? 2️⃣ Can it be measured in a week? 3️⃣ Does it target the critical 20% that drives 80% of results? (pareto) 4️⃣ Can it be amplified if it works? 5️⃣ Does it trigger a chain reaction of positive changes?
✅ If yes to all five, it's a high-leverage hinge. Do it NOW!
It's not about making the perfect move. Just make small, smart moves that compound.
The startups that lose? The ones talking a big game about big moves and ignoring the things that actually matter. The willingness to go into the coal mine (the hard, unseen work).
Words Matter.
Sometimes the hinge is a word. A word that shifts how someone perceives a sentence, a pitch, a deal, or a decision.
<ul><li>"I love your product, but it's missing X." → "I love your product, and it's missing X." One shuts down the conversation. One invites collaboration.</li></ul>
<ul><li>"Would you like to move forward?" → "How can we make this work for you?" One gives an easy "No." One forces engagement.</li></ul>
These aren't tricks just small hinges that move deals, shape decisions, and drive momentum.
Startups aren't built on one moment. They're built on 10,000 small ones.
As always, if I can be of service, feel free to <a href="https://cms.startuptoscaleup.com/products/1-hr-start-up-consulting-call" target="_blank" class="ck-link" rel="noopener noreferrer" style="color:#fa1e1e">grab</a> time. 
LFG.
-- James

Success isn't built on heroic moments. It's built on a thousand small, high-leverage decisions made consistently that open big doors in your startup journey.

Big Doors, Small Hinges

Big Doors, Small Hinges: The Leverage Points That Drive Startup Growth

StartUp Founders: Big Doors, Small Hinges

The Leverage Effect: Finding Your Startup's Small Hinges

Hey Reader,
The quicker you realize your brain has two sides, and they love to compete, the more fun everything gets.
One side wants to grind. To push through. To brute-force a solution. Startup culture punishes inaction... It worships speed.
The other needs you to step aside so it can actually do the work.
The quicker you realize procrastination also has two sides and they feel exactly the same, the more dangerous it gets.
<ul>
<li>One side is destructive. Avoidance, fear, resistance.</li>
<li>The other is constructive. Incubation, refinement, divergence.</li>
</ul>
The problem is that both feel like procrastination. The experience of strategic thinking often feels identical to procrastination. 
In reality, walking away from a hard problem often solves it faster than forcing yourself to grind through it.
You know this. You've felt it. But you ignore it because you're convinced you're wasting time. That you should be pushing harder, forcing the solution, battling through. Founder Mode.
There is a model to achieve excellence in procrastination. A way to do it right.
If it's constructive, it only works if you've actually started. If you haven't danced with the problem, your brain has nothing to solve.
The goal, is to let your brain ambush you with the best ideas while you're wasting time.
Quick Disclaimer:
This isn't a newsletter on hacks to crush procrastination. It's about understanding it and making it work for you. If you're just being lazy, start with Kaizen and come back next week.
They Have Names!!
Strategic thinking feels like procrastination, because of your discomfort of doing nothing. The anxiety of delaying action. The uncertainty of allowing ideas to incubate when it's your job to have all the answers right now.
The outcomes so many founders get are strategic, but the experience for many founders is procrastination.
Your emotions can't tell the difference between destructive avoidance and constructive incubation. That's why we label it all as "procrastination" and hate ourselves for it.
One of my favorite things is finding out that my super unique, ultra-nuanced dysfunction. The thing that makes me think I'm a unique snowflake... actually has a name. Two names, actually.
📌 The Zeigarnik Effect: Your brain hates unfinished tasks, so if you start something and then "procrastinate" your mind keeps working on it in the background.
That's why ideas "suddenly click" when you walk away or when you're in the shower not telling your brain what to think about. It's why software has progress bar during onboarding... (let that sink in)
Your brain doesn't need more brute force. It needs space.
📌 Parkinson's Law: Work expands to fill the time available for its completion.
Translation: The less time you have, the more you get done. 
We know this, it's why the last-minute rush to meet the deadline often produces our best work. When you procrastinate, you compress the timeline, forcing your brain to ruthlessly prioritize and cut the crap that never mattered.
I Spend an Absurd Amount of Time "Doing Nothing."
I call it incubating.
Some of the best work is no work. I know it, I understand it, I manage it, and I love it. A solid TikTok doomscroll does wonders for my mental health.
Would you rather have an engineer churning out endless code, ticking backlog items off like a machine?
Yes. You would. Of course. That's their job. To do the things you put on the list.
BUT, what if an engineer spent all day not coding and realized they could solve the problem with 10 lines instead of 1,000 or make something more future-proofed, more intelligent?
The idea of an engineer sitting in a conference room, doodling in a notebook for six hours, would make your blood boil. But if they took a "mental health day" to reset, you'd probably encourage it.
Both serve the same purpose.
One looks like destructive procrastination. The other is just forced, structured not-thinking (constructive). The difference is only how we choose to frame it.
We accept "rest" as valuable. We struggle to accept "not doing anything" as work.
🚀 The best line of code is no code. 🚀 The best product decisions often come from thinking, not building. 🚀 The best ideas show up when you stop forcing them.
More specifically, as you think about your product and the feature farm you've built, time allows you to think more about the outcome and less about the feature.
Call it procrastination if you want.
The Procrastination Signal.
Not all procrastination is about incubation. Destructive is just that, avoiding something you don't want to do.
It's mostly not laziness. It's fear. Fear of doing the job, where to start or how to do it.
Which gives you two options:
1️⃣ Procrastinate more and pray the problem magically disappears. (This is my default, sometimes I get lucky.) 
2️⃣ Ask yourself why, break it into bite-sized chunks, and do literally the first step. (Back to Kaizen.)
The second option almost always wins no matter how great option one sounds.
I hope you're getting the vibe of this newsletter. I'm asking you to come to terms with who you are, how you operate, and inserting some mild humor and a little truth to let you know we all do it.
It's about naming it and finding your way to make it work for you.
Your brain is a pattern-recognition engine. It works best when you give it input, then let it wander.
Sometimes, the best move is no move.
So take the walk. Watch the stupid video. Stare at the ceiling.
The trick is learning to distinguish between uncomfortable-but-productive incubation and just plain avoidance. Both feel the same in the moment – that's what makes this so tricky. The difference? Intention, starting point, and outcome.
Is it laziness or leverage? Avoidance or optimization?
Anyone else watching the guy on TikTok unclogging drains?
As always, if I can be of service, feel free to <a href="https://cms.startuptoscaleup.com/products/1-hr-start-up-consulting-call" target="_blank" class="ck-link" rel="noopener noreferrer" style="color:#fa1e1e">grab</a> time. 
LFG.
-- James

The quicker you realize procrastination also has two sides and they feel exactly the same, the more dangerous it gets. Learn to distinguish between destructive avoidance and constructive incubation.

Procrastinate More

Strategic Procrastination: Why Stepping Back Leads to Better Startup Solutions

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StartUp Founders: Procrastinate More (Part 2)

Strategic Incubation: The Power of Constructive Procrastination

Hey Reader,
You can't spend your way into product-market fit.
Early days you only have one job. Get people to need what you built. That's it. Move from experiment to business. Anything else is a distraction.
🚀 Early stage? Money buys time. 🚀 Some traction? Money buys growth. 💀 No demand? Money buys nothing.
Almost every founder finds out too late they wasted money chasing fit, either because they run out of money or the grave yard of features no one uses.
Yes, one killer feature can unlock market fit. The trap is thinking that more features = better odds. The double trap is building features instead of asking tough questions.
A true 10x feature is the result of deeply understanding user pain. Startups don't fail because they're one feature short of greatness. They fail because they are not <a href="https://www.amazon.com/Starting-StartUp-Build-Something-People/dp/1774586398/" target="_blank" rel="noopener noreferrer" style="color:#fa1e1e">listening to the market</a>.
When founders don't feel that pull from the market, they panic. Instead of asking tough questions, they start throwing money at the problem in the form of features, often without even realizing.
If the demand isn't there, all you're doing is spending more to force what isn't working. Pushing harder on a door marked pull.
Market fit isn't a cash problem. Market fit is a <a href="https://www.startuptoscaleup.com/newsletter/pmf-phantom-market-fit/" target="_blank" rel="noopener noreferrer" style="color:#fa1e1e">pull</a> problem.
This has been all of us at some point, spending more, something not working.
And deep down, you already know this, it's super scary.
It's easier to throw money at the problem than face reality. Building features feels productive. Hiring feels like progress. Spending money feels like you're doing something.
So much easier than asking the hard questions. Easier than admitting your market isn't pulling you forward, or... that you might have built something no one truly needs.
So you spend.
Hoping volume hides the weakness is a strategy to convince yourself that if you just had more, did more, built more… then everything would click.
But you don't scale into market fit. You discover it, earn it, and prove it. <a href="https://www.startuptoscaleup.com/newsletter/pmf-phantom-market-fit/" target="_blank" rel="noopener noreferrer" style="color:#fa1e1e">Fit is an outcome the market gives you</a>, it cannot be purchased.
Breaking the Paradox
This is not chicken/egg. How do I know what creates demand without building features to test….
The answer isn't "never build features." It's "never build features for features sake." (<a href="https://www.startuptoscaleup.com/newsletter/outcome-driven-design/" target="_blank" rel="noopener noreferrer" style="color:#fa1e1e">and certainly not outside core</a>)
We know this. Don't build features. Build outcomes. Don't focus on what to build. Focus on what behavior you want to enable.
The diff between: - "Let's add a dashboard" (feature-thinking) - "Let's help users understand their progress" (outcome-thinking)
Your job is to create the most value with the fewest features. Finding the simplest possible path to that outcome.
This isn't about never spending on features.
Enterprise needs integrations. Competitive spaces need parity. Scale needs onboarding.
But these accelerate an already working machine. They rarely fix a broken one.
So. Chase necessity.
Instead of spraying and praying the market to get more beans into the top of your funnel, trying to get MRR up, figure out what's keeping the ones inside.
<ul>
<li>Map their <a href="https://www.startuptoscaleup.com/newsletter/startup-value-chain/" target="_blank" rel="noopener noreferrer" style="color:#fa1e1e">value chain</a>. Who else do they interact with in their workflow?</li>
<li>Map their <a href="https://www.startuptoscaleup.com/newsletter/ecosystem-map/" target="_blank" rel="noopener noreferrer" style="color:#fa1e1e">ecosystem</a>. What tools do they rely on / integrate with?</li>
<li>Map their behavior. What pain are they solving that's bigger than your product?</li>
</ul>
You cannot spend your way into market fit. You can only find it, earn it, and scale it. So... What are you going to do differently today?
As always, if I can be of service, feel free to <a href="https://cms.startuptoscaleup.com/products/1-hr-start-up-consulting-call" target="_blank" rel="noopener noreferrer" style="color:#fa1e1e">grab</a> time. 
LFG.
-- James

The harder you push a product no one wants, the more expensive the lesson. Learn why market fit is a pull problem, not a cash problem, and how to find it.

Buying PMF

Why You Can't Spend Your Way to Product-Market Fit: A Guide for Startups

StartUp Founders: Buying Market Fit

The Pull Factor: Why You Can't Buy Product-Market Fit

Hey Reader,
There's a trap founders love walking into (and often have to & should). 
Chasing the dream customer, perfect partnership, frictionless growth channel. The massive logo that will change everything. You know you'll do anything to win it, despite the risks. And you probably should....
Founders don't care. Because the upside is real, and the belief that you can out execute the risk is what makes you a founder. Right?
But now you have to win it, at all costs. It's been the opening sentence to your investor update for the past 6 months.
The trap isn't taking these deals; it's before that. It's the gravitational pull of chasing them, the way they bend your roadmap, your team's energy, your entire company narrative - doing whatever it takes to win the deal.
The platform example: Last weeks AI wrapper newsletter, built on the back of OpenAI. What happens when they change the API, adjust pricing, or build your product natively?
It's the monopsony trap. 
Monopsony: when one entity, a customer, a platform, a partner, or a supplier, controls your destiny. They dictate the terms, control the revenue, and own your future.
Do you want one Nestle, or 10 mid-sized businesses no one has heard of? Nestle. Obvi. The logo on the deck is insta-credibility, and you know you can leverage that logo exponentially.
FYI, the answer is 10 normal customers who like your product, pay their bills, and are manageable to service. But we're founders. Our insane belief in our capability to execute and outrageous risk tolerance mean we'll chase both. Sure.
It feels like a win. That landmark customer or partner. Easier to sell, fundraise, recruit....and the adrenaline of saying Nestle is a customer.
I know the reasons.
✅ They're excited about your product. ✅ They have the size to make your ARR two commas. ✅ They have the distribution into new customers you need. ✅ They can scale you faster than you ever could alone. ✅ They will help you refine your product. ✅ They are not a customer, they are a partner.
Startups don't just die when they get outcompeted. They die when they get absorbed, controlled, or slowly squeezed out. They die when one entity owns them.
This is monopsony power aka dependence.
MONOPOLY vs MONOPSONY:
Monopoly: One seller dominates all buyers. (control supply) Think Shopify dominating e-comm or AWS controlling infra. They have the power to set the rules.
Monopsony: One buyer dominates all sellers. (control demand) Developer relies solely on the App Store (platform). Startup whose revenue comes almost entirely from one company (customer). SaaS platform dependent on a single supplier for its raw materials (OpenAI) (supplier).
Simply put? The restaurant that now gets 35% of its volume from postmates.
Monopolies drive competitors out of the market. Monopsonies own suppliers, control demand, and dictate pricing.
TAKE THE DEAL:
Startup advice is easy when you have options. Founders rarely have options. The TikTok founder telling you to make sure the investor is the right fit.
The right fit? Right now it's whoever has cash and is willing to give it to you.
Don't be dependent on one customer. Control your own destiny. Fab advice. Useless you're fighting to survive.
Its unarguable. Big logo on your customer list? Big name partnership?
Why wouldn't you? It opens doors, pays bills, and fast-tracks credibility. Walking into a monopsony isn't a mistake, do it.
We know that; we know taking that big customer or signing that big partner is going to be a nightmare. We know we will be their outsourced dev shop, fighting to keep them happy so the opportunity is expanded, we can use them as a reference, and they don't churn. We know that.
You should do it. Obviously. Well, you maybe shouldn't, but you have to.
You take it thinking you have the agility, the speed, the control. You can pivot, adjust, and maneuver in ways they can't. You think you have control.
And then one day, something changes. And when they turn, they don't pivot. They roll over everything in their path.
Or, forget about them. The minute they don't actually sign, the minute they don't actually renew, the minute your other customers are getting second-tier service because of them…
So all of this to say, you have the amount of time it takes for the monster to turn, to get in, out, and not be dependent.
So as you take a monopsony deal, a deal you are taking no matter how massive the red flags, we both know you are praying you can leverage this fast enough to not get f'd.
THE PARTNERSHIP TRAP:
Every founder talks about the "one partner" offering to take them into their distribution channels… Why. Would. They. Do. That.
There is NO scenario where any vendor puts a startup in front or alongside them, ever, unless the benefit to them is exponential.
Partnerships are amazing, I happen to think it's the most powerful way to build into a market and most founders think about it too late, it's just about understanding where you stand in the relationship.
You don't have to sell me on the partner model….
Grow fast. Faster than you can alone.
Until they don't sign, or if they do, one day, they tweak the algorithm, remove API, introduce pricing tiers, replicate your product, change direction...
By the time you realize you're in a monopsony, it's too late.
This is how platforms, marketplaces, and major customers kill startups. Slowly, predictably, and completely.
This isn't a new phenomenon. History is littered with startups that got played.
So...
You have exactly as long as it takes for the monster to awaken to do everything in your power to own the customer relationships, own distribution, own the moat, and not be entirely dependent on an entity that wouldn't notice if you disappeared. Start now.
As always, if I can be of service, feel free to grab time. 
LFG.
-- James

That massive logo on your pitch deck? It's a monopsony trap. Learn why founders chase big customers despite the risks and how to escape before it's too late.

The Monopsony Trap

The Monopsony Trap: Why That Big Customer Could Kill Your Startup

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Simply Business

StartUp Founders: The Monopsony Trap

The Gravitational Pull of Single-Customer Dependence

Hey Reader,
"That's just an AI wrapper." "A lazy UI on GPT with some marketing fluff." "A thin interface that adds nothing." "A business that could disappear overnight." 
Okay. And? 
Postmates was kinda a wrapper on top of restaurants? Uber was kinda a wrapper on top of car services? Shopify was kinda a wrapper on top of selling stuff?
Confusing? 
They started by aggregating existing supply, layered on a simple UI that connected users to a service. Isn't that what a wrapper is?
Until they weren't. Because they immediately built infra to adjust user behaviour, workflows, automations and control over the transactions.
The core value was not about connecting A to B - it was reimagining how A and B interacted. More specifically, it was owning the decision layer.
The mistake isn't building an AI wrapper. The mistake is staying one.
People calling your startup a wrapper? Good. Let them. 
Because what starts as a wrapper becomes the foundation of a business if you can evolve upstack quick enough. 
What Isn't a Wrapper?
Your startup is already a wrapper.
You didn't build your own cloud. AWS. You didn't build your own payment processor. Stripe. You didn't build your own database. PostgreSQL.
So if everything is a wrapper on something, why is "AI wrapper" an insult?
Because when people call your startup a wrapper, what they're really saying is:
👉 "You haven't added enough defensibility yet." 👉 "You don't own enough of the workflow." 👉 "If OpenAI builds your feature, your business disappears overnight."
Cursor is technically a wrapper passing GPT-generated code back and forth. But what makes it transcend wrapper status? It's not just generating code - it's integrating those outputs directly into your files, executing inside your workflow, and embedding itself to the left and right of the coding process. AI is the feature, but the workflow becomes the product.
Do Your Customers Care?
You don't demand your chef grow the peppers. You demand that you get the plate you want, how you want it, at an equitable price. The output.
This is the application layer. Where the raw ingredients are transformed into something meaningful, actionable and where your application moves from being a thin layer on top of the model, into delivering real functional value.
People don't care how it happens. They care that it happens better, faster, and easier because of you.
So don't get defensive. Let them call you a wrapper. Then build so they can't anymore.
The secret, is to own the last mile. If you own the experience the user operates in, you own the user, and wrappers, are just that, the last mile.
The Real AI Business Isn't Tech it's Distribution Arbitrage
Your real advantage isn't the LLM. It's how you get users, keep them, and expand what they do inside your platform.
Because winning AI businesses aren't just software companies. They're distribution companies.
The biggest moat isn't owning the model. The biggest moat is owning the user.
The biggest risk isn't being a wrapper. The biggest risk is staying one.
The fastest way to win is through distribution arbitrage.
If you can bring in users, convert them, and expand what they do inside your system, you control the market.
Start with a wrapper if you have to, but use it to build a distribution engine that captures the last mile.
Go Upstack Or Be Obliterated.
The stories are endless, first to market wrappers like medical voice AI startups charging $1K per month with a very reasonable pitch. "Cheaper and better than human medical scribes."
Now? They're fighting to survive at $100 per month. Why? They're competing with 10+ AI voice startups racing to the bottom on price.
Not because of better technology. Not because of changing customer needs.
Because of wrapper competition and the ease to switch between services.
This isn't an argument against wrappers. It's the strongest argument for moving up the stack. Fast.
Because when you own: ✅ The workflow ✅ The user relationship ✅ The distribution
You're not competing on price anymore. You're competing on value.
The Journey: Wrapper → Application Layer → Vertical AI SaaS
🔥 Step 1: AI Wrapper (The Starting Point) Every AI for xxxx starts here. You refine LLM prompts, improve UX, structure inputs, and optimize GPT outputs for a specific niche. It feels like you're adding value.
🚨 The Risk: But you're just passing inputs and outputs. If OpenAI improves prompting, your tool loses value overnight.
You're not a business yet. You're an interface.
✅ How to Evolve: Don't just optimize outputs. Own the workflow to the left and right of the value you deliver. Build execution layers that force users to stay inside your product.
🔥 Step 2: Application Layer (Where You Become More Than a Wrapper) At this stage, you stop just generating text/images/code and start owning the process.
Users aren't just consuming AI-generated content. They're executing tasks inside your product.
AI isn't just generating responses, it's guiding decisions.
🚨 The Risk: If your product is still just an input/output engine, users can replace you with any other AI tool.
✅ How to Evolve: Collect proprietary data that refines outputs over time. Build automation layers that create lock-in. Integrate into workflows so deeply that users can't rip you out.
At this point, you start to have real leverage.
🔥 Step 3: Vertical AI SaaS (Where You Own the Market) You're now part of core operations, of how your user does their job.
You don't just generate content, you own the system that executes it.
Now it's about how you can better control the purchase, execution, and insights inside your platform, how you can integrate deeper, how you can own more of the core.
Your Next Move
✅ Start figuring out how to own the last mile. ✅ Build something users rely on. Then make it better every day.
This isn't just the game. This is the only way AI startups survive.
As always, if I can be of service, feel free to grab time. 
LFG.
-- James

Don't fear the 'AI wrapper' label - but don't stay one. Learn the strategic evolution from wrapper to application layer to vertical AI SaaS your startup needs.

AI Wrappers

Building Beyond the AI Wrapper: From Interface to Market Owner

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StartUp Founders: AI Wrappers

Beyond the Interface: Transforming AI Wrappers into Market Owners

Hey Reader,

The founder is always the protagonist. It's the most epic, terrifying, and brutal part of starting a startup. Until you confuse protagonist with savior.

*"We need to build everything in-house. It's the only way to ensure quality."*

This founder's Series A startup had burned through $8M building their own infrastructure. They shut down last month.

That's not you, you don't have $8m and not building your own infra, but the underlying mistake. That's you.

It wasn't stupidity that killed them.  
It wasn't lack of talent.   
It wasn't even running out of money.

It was an **anti-pattern** - the strategic decision that felt completely logical, even wise, 100% justified in the moment.... but wasn't.

**That's what makes anti-patterns so dangerous.**

They don't feel like mistakes.  
They feel like strategy.  
They masquerade as wisdom.

**This week's newsletter is different.**

After reading a LinkedIn post on startup anti-patterns by [Itamar Novick](https://www.linkedin.com/in/itamarnovick/), Founder & GP of [Recursive Ventures](https://www.recursiveventures.com/?utm_source=startuptoscaleup.com&utm_medium=newsletter&utm_campaign=antipatterns) (an early-stage fund backing pre-seed and seed AI startups), I invited him to write this week's newsletter.

With 100+ investments and hundreds of startup successes and failures, Itamar has documented 74 ways good decisions quietly kill great companies.

Anti-patterns are strategic missteps that feel smart. Until they aren't.

**HYPER RELATED:**

Related: This is week two of silent killers. Death by a thousand cuts. Last week, [entropy](https://www.startuptoscaleup.com/newsletter/entropy-wins/), the slow decay of systems, focus, and execution. This weeks anti-patterns is the brutal follow up.

I'm not in a downer phase. This is our protagonist era. :)

**Startup anti-patterns in Itamar's words...**

When founders ask me what makes startups succeed, I don't have a great answer beyond "strong team, hustle, luck & timing."

But failure? Failure follows a playbook. Statistically, most startups fail, and as a result there is actually much more data about startup failure.

For better or worse, it is only the startups **that repeatedly don't fail** that have the chance to take advantage of luck and timing.

Anti-patterns are the silent killers. They're not stupid mistakes. They're not rookie errors. They're strategic decisions that feel completely justified in the moment.

That's what makes them lethal. They disguise themselves as the right move, never feeling like an anti-pattern when you're in it.

* You're not customizing, you're "landing a whale"
* You're not overbuilding, you're being "thorough"
* You're not losing focus, you're "following the market"
* You're not delaying launch, you're "getting it right"

Then one day you wake up and realize what happened:

* That "strategic" enterprise deal? It owns your roadmap.
* Your "thorough" approach? You missed the market.
* Your "market responsive" strategy? You're chasing competitors.
* Your "perfect" launch? It's six months too late.

Small failures are part of the process. You stumble, adjust, learn, iterate, and just keep moving. Anti-patterns? They don't teach you. They compound. It's too late to recover.

Why are they so lethal? **Because they compound.**

* One custom integration becomes two.   
  (Customize vs Configure)
* Two enterprise pilots become your whole roadmap.   
  (The big customer won't stop demanding features. You're now their outsourced dev team.)
* Your "temporary" tech debt defines your product.   
  (The quick fix so we can push to prod, is now part of core)
* Your "feature chasing" mindset becomes your culture.   
  (Lack of absolute clarity and mixed objectives is the new new)

I've watched hundreds of startups rise and fall. Success stories are unrepeatable.

But failure often follows patterns. You think you're making the right choice. Until you're not.

They often fall into two distinct buckets. Strategic & Execution.

STRATEGIC KILLERS:

1. **If You Build It, They Will Come** ​  
   You: "The product sells itself"   
   Reality: No, it doesn't. Ever.
2. **Ivory Tower Syndrome**   
   You: "We know what users need"   
   Reality: Your assumptions are close but rarely exact.
3. **Competition Obsession**   
   You: "We need feature parity"   
   Reality: You're always one step behind, playing catch-up.
4. **The Perfect Product Trap**   
   You: "We'll launch when it's ready"   
   Reality: It's never ready, and the market moved on.

EXECUTION TRAPS:

1. **The Enterprise Trap**   
   You: "This whale will change everything"   
   Reality: You're now a consulting company pretending to be a startup.
2. **The Infrastructure Trap**   
   You: "We need to control the full stack"   
   Reality: Great tech, no users.
3. **The Feature Factory**   
   You: "Just one more sprint"   
   Reality: Your MVP is never minimal.
4. **The Focus Fallacy**   
   You: "We can do it all"   
   Reality: You're doing nothing well.

I've documented [74 different anti-patterns](https://www.itamarnovick.com/intro-to-startup-anti-pattern-series/?utm_source=startuptoscaleup.com&utm_medium=newsletter&utm_campaign=antipatterns) that kill startups. Each one felt logical at the time. Each one had good reasons behind it. Each one slowly killed otherwise promising companies.

The startup graveyard is full of founders who made "smart" decisions.

Anti-patterns are not a death sentence. They're a test. Spotting them before they become terminal?

Before any "strategic" decision, you align it to a framework of how you make big decisions:

* Speed vs Drag: Will this make us faster or just look busy?
* Real vs Imagined: Are we solving actual customer pain or our own fears?
* Impact vs Effort: Will anyone care about this in 12 months?
* Fight vs Flight: Are we building toward opportunity or running from fear?

Each question you skip is an anti-pattern waiting to happen.

Anti-patterns don't kill you overnight. They kill you slowly. One logical decision at a time.

So many founders after their shutdown will tell you that "Looking back, every decision made sense."

Your startup isn't special. Neither was that Series A company that just died. They made logical decisions. They had good reasons. They were smart people.

But anti-patterns don't care about your IQ. They don't care about your funding. They don't care about your vision.

They just slowly, silently kill otherwise promising startups.

As a founder, your job isn't to know all the traps. It's to try and recognize the signals. To see them coming. Not every anti-pattern is a mistake. Some are calculated bets, and that, is trying to know when to pull back and when to hold the line.

Thanks for reading, please follow me on [LinkedIn](https://www.linkedin.com/in/itamarnovick/) for more.

Itamar

\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_

Thank you Itamar.

As always, if I can be of service, feel free to grab time.

LFG.

-- James

Anti-patterns feel like smart strategic decisions but slowly kill startups. Learn to identify these silent killers that masquerade as wisdom from VC Itamar Novick.

Anti-Patterns

Startup Anti-Patterns: How 'Smart' Decisions Silently Kill Companies

StartUp Founders: Anti-Patterns

The Silent Killers: Strategic Decisions That Destroy Startups

Hey Reader,
Startups rarely fail with a bang. Most fail with a thousand tiny compromises.
But the ones that get a little traction? The rare combo of relentless founder and a validated idea (the jockey and the horse). So many of them die because they can't convert that early traction into something bigger.
Often because entropy wins.
You're doing the work. Motivated. Excited. Probably working harder than ever. Momentum definitely feels real.
And yet...
Things are slipping.
Entropy isn't inaction. It's often misplaced effort.
HYPER RELATED:
Last week, I talked about how <a href="https://www.startuptoscaleup.com/newsletter/motivation-hurts/" target="_blank" rel="noopener noreferrer" style="color:#fa1e1e">motivation</a> isn't what keeps founders moving, it's just the spark. It's systems and discipline that deliver the momentum. But systems, especially in startups are almost designed to break down. That's this week, that's entropy, and it doesn't care how motivated you are.
Feel familiar?
<ul class="unordered_list" style="font-family:Geneva, Calibri, -apple-system, BlinkMacSystemFont, sans-serif;font-size:16px;color:#353535;font-weight:400;letter-spacing:0;line-height:1.5;text-align:left;text-transform:none;margin-top:24px;margin-bottom:24px;list-style-position:inside">
<li class="list_item">Your engineer is suddenly "too busy" for standups. … Your standup was sacred until that one busy Monday.</li>
<li class="list_item">Your sales pipeline? Getting "updated tomorrow." … You're in back-to-backs, so you'll do it later.</li>
<li class="list_item">The tech debt you know is fatal is now "next sprint." … Your QA process worked until that urgent hot fix.</li>
<li class="list_item">Customer feedback? You'll "look into it when things calm down." … Your customer obsession was solid until that big feature launch.</li>
<li class="list_item">Your metrics dashboard? Gathering cobwebs. … Your metrics review was weekly until it wasn't.</li>
</ul>
One exception becomes two. Two become normal. Normal becomes chaos.
We've all been there, overwhelming amount of customer promises, missed release dates, competing priorities, and mounting chaos.
You're a firefighter running around putting out the tiny fires because you don't have the time or money to focus on the inferno, which is just far enough away to be ignored.
Every Slack "ding" is met with the fear it could be an outage or a crisis… because it usually is.
This is why entropy is so dangerous: in the moment, the trade-offs feel completely reasonable and even necessary - you are right to make those trade-offs.
<ul class="unordered_list" style="font-family:Geneva, Calibri, -apple-system, BlinkMacSystemFont, sans-serif;font-size:16px;color:#353535;font-weight:400;letter-spacing:0;line-height:1.5;text-align:left;text-transform:none;margin-top:24px;margin-bottom:24px;list-style-position:inside">
<li class="list_item">Metrics don't matter if the pitch fails and we run out of cash.</li>
<li class="list_item">The hot fix gives us the breathing room to get this customer off our back.</li>
<li class="list_item">Would you rather me selling or updating hubspot?</li>
</ul>
This is what makes fighting entropy so f'd up. It disguises itself as prioritization.
To repeat... Entropy doesn't win with a bang. It wins with a thousand tiny compromises.
I'm pro-chaos. That's not this.
Chaos is fine. Mayhem is fine. A shit show is expected. It's supposed to be messy, unscalable and generally impossible.
Entropy is the slow decay of your systems, focus, and execution.
<ul class="unordered_list" style="font-family:Geneva, Calibri, -apple-system, BlinkMacSystemFont, sans-serif;font-size:16px;color:#353535;font-weight:400;letter-spacing:0;line-height:1.5;text-align:left;text-transform:none;margin-top:24px;margin-bottom:24px;list-style-position:inside">
<li class="list_item">Chaos is shipping a feature the night before launch. Entropy is never revisiting it to fix the bugs.</li>
<li class="list_item">Chaos is running down 10 leads at once. Entropy is forgetting to follow up because you're too busy.</li>
<li class="list_item">Chaos is 2am triaging production issues. Entropy is letting tech debt pile up until it defines your product.</li>
</ul>
Chaos is the grind. Entropy is when the grind become the standard.
Early days, you are E1 (Entropy of One)
It's just you (and your upwork engineer!) - you are the chaos generator. No processes exist outside of what is in your head.
That's normal. Thats the trap. When it's just you, chaos feels like speed. It's not. Chaos only works when it's contained by systems. It cannot be the system.
Every decision. Every action. Big and small. From vision to TestFlight builds.
This is E1: Entropy of One. One founder, no systems, pure chaos. It's not innovation. It's disorder.
You can't beat entropy. Fact. Every system tends toward disorder.
This isn't about motivation (we covered that). This isn't about product-market fit (if you believe in it).
Every founder with a tiny bit of traction thinks they can outwork entropy. You can't.
You can only try to build systems that force order, even when chaos is trying to crush you.
As you grow, things start to take longer. They just do. Not everyone has the founder adrenaline to live and die with every push to prod, every lost customer, or every missed milestone. They shouldn't have to.
The goal isn't to defeat entropy. It's to delay it. To control its pace.
Entropy comes for every startup. The difference isn't work ethic or idea validation or even market traction.
It's systems.
Stay in the fight.
As always, if I can be of service, feel free to <a href="https://cms.startuptoscaleup.com/products/1-hr-start-up-consulting-call" target="_blank" rel="noopener noreferrer" style="color:#fa1e1e">grab</a> time.
LFG.
-- James

Startups don't fail with a bang - they fail with a thousand tiny compromises. Learn how entropy disguises itself as prioritization and how to build systems to combat it.

Entropy Wins.

How Entropy Kills Startups: The Silent System Breakdown

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Increase engagement. Convert trial users. Boost product retention. Send targeted emails when people do or don't do something.

StartUp Founders: Entropy Wins.

The Silent Startup Killer: How Entropy Destroys From Within

Hey Reader,
That motivation you felt on January 1st? Dead?
We all entered January high on motivation. New year, new me, new strategy, new momentum - this is MY year.
Then reality hits...
The fires burned, TikTok turned off, political uncertainty loomed... Your prospects ghosted. Your ads didn't convert. Your dev team just cannot finish that feature.
New Year. New Me. Got you to mid January! It's not even February, and the cracks are already showing, for everyone, not just you.
Motivation is why everyone signs up for the gym membership on Jan 1. Yet... Every founder finds out the hard way, motivation disappears when the real work begins.
Motivation isn't the word. It never was.
HYPER RELATED:
<a href="https://www.linkedin.com/posts/jdsinclair_startup-founders-you-dont-do-product-you-activity-7276525588339666944-T6M5?utm_source=share&amp;utm_medium=member_desktop" target="_blank" rel="noopener noreferrer" style="color:#fa1e1e">Outcomes</a>: Visionaries do the work to earn the outcomes. Wannabes just declare them.
<a href="https://www.linkedin.com/posts/jdsinclair_startup-founders-the-dip-startup-to-scaleup-activity-7263809676369158144-Odhd?utm_source=share&amp;utm_medium=member_desktop" target="_blank" rel="noopener noreferrer" style="color:#fa1e1e">The Dip</a>: Every startup founder has, is, or will feel it. The gap between all the work you've done and the results you're waiting for.
Motivation Is Bullsh*t
I get more calls for founder coaching in the last 15 days of January than at any other time of the year. Why? Because the energy founders started with was never designed to keep you afloat - it evaporates. How can it be this hard, so early in the year.
Motivation is bullshit. It's unreliable, and always f*cks off right when you need it most.
You know this because motivation never shows up on the 50th failed investor pitch. Never checks in on you when your push to prod explodes. Never sends a positive haiku when your prospects ghost you.
Motivation is just the spark to get you started. A spark not designed to last. Discipline is the fuel that keeps you going, what sustains your efforts. Systems are the engine that makes progress inevitable, whether you're feeling motivated or not. (Momentum is the outcome)
Just To Clarify
Founders who don't want to do the hard work or are feeling defeated build fake systems to feel productive without doing the work. The workflows, processes, and tools no one asked for - they build "scalable systems" despite no scale.
Real systems come from doing the atomic work, the simple, disciplined actions that stack over time. The ones you execute relentlessly every single day.
Atomic actions create discipline. Discipline creates predictability. Predictability creates momentum.
Over time, this compounds into the scalable systems and processes every founder wants.
That's what I mean by systems. Not automations, but habits. Not workflows, but actions. Not frameworks, but execution.
To win....
<ul class="unordered_list" style="font-family:Geneva, Calibri, -apple-system, BlinkMacSystemFont, sans-serif;font-size:16px;color:#353535;font-weight:400;letter-spacing:0;line-height:1.5;text-align:left;text-transform:none;margin-top:24px;margin-bottom:24px;list-style-position:inside">
<li class="list_item">The grit to show up when nothing is working.</li>
<li class="list_item">The discipline to do the unglamorous, repetitive work.</li>
<li class="list_item">The systems that make progress inevitable, even when you're not doing so great yourself.</li>
</ul>
Systems + Discipline = The ability to do the work when you'd rather do literally anything else.
Don't Wait for Motivation
When founders fail, it's not because the market was tough (it always is).
It's because they froze, hesitated, or couldn't push through when it got hard.
Execution is what fails most founders. Not ideas. Not timing. Not market conditions. Execution.
Capability to execute is what separates you from them.
Think about it:
<ul class="unordered_list" style="font-family:Geneva, Calibri, -apple-system, BlinkMacSystemFont, sans-serif;font-size:16px;color:#353535;font-weight:400;letter-spacing:0;line-height:1.5;text-align:left;text-transform:none;margin-top:24px;margin-bottom:24px;list-style-position:inside">
<li class="list_item">A system of 5 customer calls daily doesn't care if you're motivated.</li>
<li class="list_item">Backlog grooming happens whether you're inspired or not.</li>
<li class="list_item">Daily standups force progress, no matter your mood.</li>
</ul>
Phenom founders move past relying on motivation and build systems and discipline that keep them moving forward at. all. costs.
The engine is you. Doing the work. Every single day.
SO, WHAT SHOULD YOU DO?
Forget (but don't) the big thing when you're in the trenches. Just do the next job. The next prospect. The next iteration. Build momentum by just doing the work. One tiny thing at a time.
Just maybe....
<ol class="unordered_list" style="font-family:Geneva, Calibri, -apple-system, BlinkMacSystemFont, sans-serif;font-size:16px;color:#353535;font-weight:400;letter-spacing:0;line-height:1.5;text-align:left;text-transform:none;margin-top:24px;margin-bottom:24px;list-style-position:inside">
<li class="list_item">One system that drives prospects (5 cold outreach before 9am)</li>
<li class="list_item">One process that ensures progress (Daily ship something, anything)</li>
<li class="list_item">One mechanism that forces growth (Weekly metrics review, no excuses)</li>
<li class="list_item">One framework that maintains momentum (End of day planning ritual?)</li>
</ol>
Don't overthink it. Do the atomic actions. Do that every (day) quarter. That's it.
Systems don't care about your motivation. They don't have feelings. They don't care about your why. They don't care about your vision board. They just work.
The founders who win aren't the most motivated. 
They're usually the most tired, look like shit (until momentum kicks in then they have a glow up) - aged, battered, bruised, and in pain - but through it all (she offers me protection) they're the ones who built systems that made success inevitable when everything was working against them.
Motivation may be fleeting. But systems? Systems never die.
Stay in the fight.
As always, if I can be of service, feel free to <a href="https://cms.startuptoscaleup.com/products/1-hr-start-up-consulting-call" target="_blank" rel="noopener noreferrer" style="color:#fa1e1e">grab</a> time.
LFG.
-- James

Motivation is just the spark to get started, not the fuel that keeps you going. Learn why systems and discipline are what truly drive startup success.

Motivation Hurts.

Why Motivation Fails Founders (And What Actually Works)

StartUp Founders: Motivation Hurts

Beyond Motivation: Why Systems Beat Willpower Every Time

Hey Reader,
First, wishing you and yours a healthy, happy holiday season, and a moment for real reflection.
Second, thank you. I started this newsletter 18 months ago to stay connected with people who reached out for assistance. 150k readers later, it's the best part of my week. I have no saved drafts. Just me, every Friday night, arguing with myself about what I want to say.
Feel like leaving a <a href="https://senja.io/p/startup-to-scaleup/r/8MWouG" target="_blank">testimonial</a>?
I want to share three (of many) mindset shifts that changed how I think and operate as a founder:
Accountability: It's all my fault aka <a href="https://positivepsychology.com/internal-external-locus-of-control/?utm_source=startuptoscaleup.com&amp;utm_medium=email&amp;utm_campaign=EoY" target="_blank" rel="noopener noreferrer" style="color:#fa1e1e">Internal Locus of Control</a>
It's not always literally true, and often, it's not totally fair, but adopting total ownership over outcomes changes everything.
Accountability is cultivating an internal locus of control. The (real) belief that you have the power to influence events and outcomes vs being a victim of external forces.
When you truly believe you influence every result, an immediate shift occurs. Blame becomes irrelevant. Blame is exhausting.
It's not the algorithm, the engineer, the investor, the market, the economy, or your co-founder. It's you. Own that.
This isn't manifesting. That's the positive thinking and visualizing. ILoC is about taking ownership AND action. Think it, do it, own it (the results).
Judgment: They're not thinking about you at all aka <a href="https://www.verywellmind.com/what-is-the-spotlight-effect-3024470/?utm_source=startuptoscaleup.com&amp;utm_medium=email&amp;utm_campaign=EoY" target="_blank" rel="noopener noreferrer" style="color:#fa1e1e">Escaping the Spotlight Effect</a>
So much isn't done because you are concerned, worried, or feel judgement on whatever it is you are not doing. The LinkedIn post, cold email, build in public, speaking up, product idea. The fear of judgment blocking you is not real, it has a name -> "spotlight effect" -> we overestimate how much attention others pay to our actions.
Eight years ago in NYC a woman waved at me, I waved back, then she got in the cab she was waving down. She probably didn't even see me. I still think about it, sometimes daily. That's the spotlight effect... overestimating how much people notice or care.
Accepting how little people focus on me (was humbling) but.. I got bolder which enabled bigger ideas, bigger bets. The market responded differently because I was showing up differently.
(It's not easy. My <a href="https://www.tiktok.com/@startuptoscaleup" target="_blank" rel="noopener noreferrer" style="color:#fa1e1e">TikTok</a> acct. I would rather be in the coffin than giving the eulogy, I have hundreds of drafts, but when I do post, it almost always leads to something great.)
Every founder who's broken through had to get comfortable being uncomfortable. The first pitch, the bold claim, the controversial take... All started with a founder prioritizing the need to succeed over fear of judgement.
Empathy: Battling the <a href="https://positivepsychology.com/fundamental-attribution-error/?utm_source=startuptoscaleup.com&amp;utm_medium=email&amp;utm_campaign=EoY" target="_blank" rel="noopener noreferrer" style="color:#fa1e1e">Fundamental Attribution Error</a>
We often attribute how other people act to who they are rather than what they're going through. Assumptions are the enemy of understanding.
When you accept that you don't know what battles others are fighting, you default to patience, better communication, and less wasted cycles on resentment. Empathy is a massive strategic advantage, it strengthens how you show up and do everything.
These three mindsets live together. Accountability drives action. Freedom from judgment enables boldness. Empathy ensures we're building something that matters.
In addition to using <a href="https://www.startuptoscaleup.com/newsletter/2025-strategy/" target="_blank" rel="noopener noreferrer" style="color:#fa1e1e">Q5</a> to get your house in order. Maybe also a chance for deeper reflection and remembering why you started this wrecking ball of a journey in the first place.
Showing up better for yourself won't just make you a more effective founder. You'll be a clearer, more resilient human being.
I read every <a href="https://www.startuptoscaleup.com/newsletter/2025-strategy/" target="_blank" rel="noopener noreferrer" style="color:#fa1e1e">end-of-year recap newsletter</a> you sent my way. Thank you. They matter. They're part of your story, and your story matters to me.
Stay human. Stay hungry. Stay humble.
As always, if I can be of service, feel free to <a href="https://cms.startuptoscaleup.com/products/1-hr-start-up-consulting-call" target="_blank" rel="noopener noreferrer" style="color:#fa1e1e">grab</a> time.
LFG.
-- James

Discover the three critical mindset shifts that can transform your startup journey: accountability through internal locus of control, freedom from judgment, and empathy to build what truly matters.

My Fault.

Founder Mindset: How Accountability, Boldness, and Empathy Drive Success

StartUp Founders: My Fault

Three Founder Mindsets That Will Transform Your Business

Hey Reader,
Don't say it. December's a dead zone. Investors are skiing, customer "out of offices" are already appearing, and you've put your pipeline & outbound on ice.
I don't buy it, but let's pretend I agree. That leaves one option…
T-21 days. 504 hours (300 working hours?). To roll into 2025 ready to just f'n explode. Jan 6th. First Monday back. That's your moment of truth.
This isn't the end of a year. It's the start of one.
While everyone's mumbling their "New Year, New Start" mantra, you better be gearing up and already in motion, ready to EXECUTE on day one. Otherwise, you've already lost Q1.
If you didn't build your <a href="https://www.startuptoscaleup.com/newsletter/2025-strategy/">strategy</a>, you can't blame the market for your failure to do the hard work.
HYPER RELATED:
Last <a href="https://www.startuptoscaleup.com/newsletter/reality-construction-perception-gap/">week</a> rattled some feathers: You don't do product. You don't do growth. You don't do innovation. You don't do funding. You don't do disruption. You don't get to self-name these attributes. They are given to you. By the market. They are outcomes.
LETS GET INTO IT:
Most founders write off the stretch between Thanksgiving and New Year as dead. It's not. It's Q5. The pocket of weeks that everyone gets, but few actually leverage.
I had a boss who would turn your Q4 into his Q1. While everyone else treated October - December as a year-end final close / cooldown, he used it to map every account, build his strategy, tune his engines, refine his message, make his critical hires, and line up every ask. By January, when everyone else is just warming up, he was in full stride, his Q2.
First. Your Pipeline: Two Customer Types
<ul class="unordered_list">
<li class="list_item">Not-Ready-to-Close: Send a personal holiday note. Real gratitude, real connection. No automation, no templates, no hidden agenda, no growth hack. Just genuine appreciation. If you can't think of something personal to say, you're not building relationships, you're collecting contacts and haven't realized sales is a personal journey.</li>
<li class="list_item">Proposal Sent (HubSpot Column): Most founders avoid tough questions because they fear tough answers. It's time. Pick up the phone or jump on Zoom: "We've been working on aligning our solution to your needs. Do you think this is a deal we can make happen?" Direct ask, clear intent. If you lose them now, you were going to lose them anyway. If not, you'll get clarity on the close plan. I'm not worried about whether it's 15 days or 5 days before the new year. That's not the point. I'm focused on forcing you to ask the question that's been living in your head since the prospect entered your pipeline... will it close.</li>
</ul>
Second, Your End-of-Year Update
Send it to everyone. Customers, prospects, investors. Show them the future they want to believe in.
<ul class="unordered_list">
<li class="list_item">Thank You: For sticking with us, giving feedback, being part of this journey.</li>
<li class="list_item">Our Outcomes: The real, tangible results you're fighting to deliver.</li>
<li class="list_item">Our Execution: The wins, the lessons, the behind-the-scenes peak into your soul.</li>
<li class="list_item">Our Continuation: How you're doubling down, no matter what.</li>
<li class="list_item">An Ask: Why not ask for something you need (not funding).</li>
</ul>
They know you're early-stage. They know it's not all sunshine and rainbows. Transparency is an underrated quality. Show them you know where you stand, where you're going, and how.
I want to read it too, add me to your mailing list.
More Important: Your team needs to know exactly what they're heading when January hits. Not vague growth goals or general direction, crystal clear and absolute objectives and priorities. It would seem reasonable to ask if everyone in your company knows your top 3 objectives? Can they? Ask them...
.....Fighting the urge to scrap this entire newsletter and rewrite it as a manifesto against founders who isolate knowledge, treat objectives like classified info, and push people to stay in their lane. Don't do that. Make it explicit. Share it. Alignment matters.
So. Before January 6th...
<ul class="unordered_list">
<li class="list_item">Account planning - know exactly who you're targeting</li>
<li class="list_item">Prospect heat maps - know your buyer profiles per target</li>
<li class="list_item">Messaging - refined, deployed & ready</li>
<li class="list_item">Outbound engine - tested & tuned</li>
<li class="list_item">Dashboards - simple, clear & actionable</li>
<li class="list_item">Alignments - a fully sync'd team</li>
<li class="list_item">Blockers - identified & addressed</li>
<li class="list_item">All of it.</li>
</ul>
Wake up January 6th in execution mode. Do the hard work now.
LFG.
-- James

While everyone's treating December as downtime, strategic founders are using these 21 days to prepare for explosive January execution. Don't wait for the new year – start it now.

T-21 Days. Ready?

Why Smart Startup Founders Turn December Into Their Q1

Yes, the TikTok creator we LOVE! Simon Squibb is on a mission to help young entrepreneurs discover their passion and start their business. What's Your Dream? is the step-by-step guide to turn your dream venture into a reality.

What's Your Dream?

StartUp Founders: T-21 Days. Ready?

Turn Your Q4 Into Q1: The Founder's End-of-Year Advantage

Hey Reader,
Every founder is racing to build a product. Every team calls themselves innovative. Every startup claims to be disruptive. Everyone believes they're running a growth playbook. Every pitch deck believes itself to be funding ready.
Nope. Those are outcomes. You don't get to say those words.
You don't do product. You don't do growth. You don't do innovation. You don't do funding. You don't do disruption. You don't get to self-name these attributes. They are given to you. By the market. They are outcomes.
What do you do? You do the work. Do the learning. Do the solving. Do the proof. You earn those titles.
Visionaries do the work to earn the outcomes. Wannabes just declare them.
<a href="https://www.startuptoscaleup.com/module0.7/">Outcomes</a> are what the market gives you when you've solved a killer problem, built something people really want and will pay for, and, done the grind of making sure your market can find, use, and buy it.
HYPER RELATED:
Every startup founder has, is, or will feel it. The gap between all the work you've done and the results you're waiting for. It's awful. It's universal. It's "<a href="https://www.linkedin.com/posts/jdsinclair_startup-founders-the-dip-startup-to-scaleup-activity-7263809676369158144-Odhd?utm_source=share&amp;utm_medium=member_desktop">The Dip.</a>"
LETS GET INTO IT:
You don't build an Oscar winning movie. You build a compelling story, assemble a talented team, craft each scene with precision, perfect the cinematography, refine the editing, and create something that resonates with audiences. The market then decides if they agree with you - first at the box office, then through critical acclaim, and maybe, just maybe, with an Oscar. But that's not up to you. That's an outcome.
You don't build a unicorn. You solve a real problem, assemble the right team, build effective systems, craft exceptional experiences, and create something that resonates with customers. The market decides if they agree with you - first with their wallets, then with their loyalty, and maybe, just maybe, with a billion-dollar valuation. But that's not up to you. That's an outcome.
The founder of Pinterest went coffee shop to coffee shop, day in day out, asking people to try his new thing. Just doing the work, the raw, unglamorous, necessary, dirty, in the trenches work. There's no "kinda" doing the work - either you do it or you don't. EVERYONE started exactly where you are right now, even the unicorn-makers.
Every bone in your body is itching to design, code, and ship. You think you're building a product. You're not. You're building a solution to a problem for people lined up ready to pay for it. Your customers decide if its disruptive or innovative.
<a href="https://www.startuptoscaleup.com/module0.7/">Framework: Outcome Drivers</a>
If you CANNOT CONTROL the outcome, what can you control….
The inputs: - How many customer conversations you have - How many iterations you make - How deeply you understand the problem - How effectively you deliver value - How systematically you build distribution - How consistently you show up to do the work
How quickly you can release, learn, iterate, and, release again... aka Clockspeed.
How do you organize?
The Daily Grind: 
<ul>
<li>Deep problem understanding - relentless investigation into customer pain points </li>
<li>Customer conversations - constant engagement with your market </li>
<li>Solution iteration - continuous refinement based on feedback </li>
<li>Value delivery - consistent creation of customer benefits</li>
</ul>
The Systems Work:
<ul>
<li>Distribution building - systematic creation of channels to reach customers </li>
<li>System development - creating scalable processes and mechanisms </li>
<li>Relationship cultivation - building trust with customers and stakeholders </li>
<li>Data collection - gathering and analyzing market signals</li>
</ul>
The Foundation: 
<ul>
<li>Execution optimization - improving how you deliver your solution </li>
<li>Market listening - staying attuned to shifts and opportunities </li>
<li>Team building - assembling and aligning people around the mission</li>
<li>Foundation laying - creating infrastructure for sustainable growth</li>
</ul>
The market will tell you what you've built. Your job is to keep iterating until it tells you something you like.
As always, if I can be of service, feel free to <a href="https://cms.startuptoscaleup.com/products/1-hr-start-up-consulting-call">grab</a> time. 
LFG.
-- James

Visionaries do the work to earn the outcomes. Wannabes just declare them. Learn how startup founders shift from dreamers to doers by focusing on the inputs they can control.

Don't Build Product.

Why Startup Founders Should Focus on Inputs, Not Outcomes

Nurture, convert, and onboard customers with advanced behavior emails, company profiles, billing integrations, and CRM sync. Increase engagement. Convert trial users. Boost product retention. Send targeted emails when people do or don't do something.

The Marketing Automation Platform For SaaS Apps

StartUp Founders: Don't Build Product.

Stop Self-Labeling: Your Market Decides What You've Built

Hey Reader,
This one's for all the founders heading into 2025 thinking your strategy will unfold naturally, as a sequence of inevitable events. It won't. 
I'm just asking you to clearly articulate your objective and how you intend to hit it, it's a very reasonable question....
There are four types of founders on December 1st: 
<ol>
<li>Those winging it with random acts of execution believing they are following a plan. </li>
<li>Those carrying a strategy in their head, trusting a brain notoriously bad at managing task lists. </li>
<li>Those who think strategy is 10 minutes and an Asana subscription. </li>
<li>Those who know that ambitious goals require breaking them into micro-components, writing them down and relentlessly executing.</li>
</ol>
I don't need to ask which one you are. Hello to all my (a) and (b) founders out there. It doesn't work. Never has. Never will.
Your brain is great for ideas but awful for execution. It lies to you. It tells you the next thing is obvious, that you won't forget, but you do.
"Plans are worthless, but planning is everything." Eisenhower
HYPER RELATED:
Every startup founder has, is, or will feel it. The gap between all the work you've done and the results you're waiting for. It's awful. It's universal. It's "<a href="https://www.linkedin.com/posts/jdsinclair_startup-founders-the-dip-startup-to-scaleup-activity-7263809676369158144-Odhd?utm_source=share&amp;utm_medium=member_desktop">The Dip.</a>"
LETS GET INTO IT:
I'm not suggesting you plan the year. Maybe just 3-6 months out, but, to repeat, it's not unreasonable to expect you to have clarity on your objective and a map of what it takes to hit it.
I hear you....
"I'm not the strategy type." "It's just me and a dev in Slack." "Why would I write a strategy just to read it back to myself?" "I know what I need to do. Writing it down takes me out of beast mode."
Writing down your plan isn't just documentation; it's about <a href="https://www.15secondstartup.com/posts/15-second-startup-rubber-duck-debug">clarifying</a> your thinking, the process itself is where the magic happens.
If you can't write it down clearly, you don't actually know what you're doing. And if you don't know what you're doing and can't articulate it, how can you expect your employees, your contractors, your potential investors, or your prospects to?
"A problem written down is a problem half solved." Taleb.
Strategy is just breaking down your big goal into achievable steps. Then actually writing it down. Then actually doing it.
Four Levels of Planning:
<ol>
<li>Vision (12 Months): Your north star. Ambitious yet achievable. Come this time next year, where do I want to be.</li>
<li>Strategy (6 Months): The roadmap to that vision. The milestones, dependencies, and resources required. Most founders fail here and skip straight from vision to the playbook.</li>
<li>Execution (90 Days): The battleground. What's happening this quarter, month, week that gets us one step closer to our objective.</li>
<li>Atomic Playbook (Weekly Actions): Tiny, consistent steps taken every week that compounds towards your goal. The 3-5 things you can do every week to make progress inevitable?</li>
</ol>
Every strategy must include the Atomic Playbook, the weekly actions you take to ensure your progress compounds. Don't confuse it with a task list, it's not, it's your system to ensure you know exactly what you should be doing.
"Strategy without tactics is the slowest route to victory. Tactics without strategy is the noise before defeat." Sun Tzu
Why Most Strategies Fail
<ol>
<li>Arrogance.​ You just believe you are fast enough, strong enough, quick enough, and great enough to brute force your way into making something you cannot even articulate happen. Overconfidence in the absence of clarity is bananas.</li>
<li>Not Written Down.​ Your brain is for having ideas, not storing them. Write. It. Down.</li>
<li>Vague.​ "Growth" isn't a strategy. "Increase sales" isn't a strategy. If you can't answer who, what, and by when, it's just an idea.</li>
<li>Ignore Dependencies.​ Goals have prerequisites. Milestones have dependencies. Map them out or prep for the inevitable roadblocks.</li>
<li>Not Measurable.​ If you can't measure it, you can't improve it, if you can't track it, you can't fix it when it breaks. And it always breaks.</li>
</ol>
​<a href="https://www.startuptoscaleup.com/startup-framework/startup-basics/startup-project-management/">Not A Strategy Template, But The OPPM Might Help....</a>​
The "Let's Start Somewhere" Strategy
For founders who don't think they need a strategy or don't know where to start. 
Start simple. Start actionable. Start here: 
<ol>
<li>One Clear Objective: What's the ONE thing that must happen in the next 6 months? Not three things. Not five things. One.</li>
<li>Three Key Results: Measurable milestones that prove you're on track. If these don't happen, the objective won't happen.</li>
<li>Critical Dependencies: What has to be true for this to work? What resources, people, or conditions need to exist?</li>
<li>Atomic Actions: What 3-5 small, repeatable steps can you take weekly that will compound toward your objective?</li>
</ol>
When market conditions change (they <a href="https://www.startuptoscaleup.com/newsletter/adapt-to-market-shifts/">will</a>), when customer needs evolve (they do), and when assumptions prove to be wrong (they always do), your strategy is the framework for adaptation vs reactive prayer.
So. Start writing something. Today….
As always, if I can be of service, feel free to <a href="https://cms.startuptoscaleup.com/products/1-hr-start-up-consulting-call">grab</a> time. 
LFG.
-- James

Most founders are winging it with random acts of execution or carrying their entire strategy in their head. Learn why writing down your plan isn't just documentation - it's clarifying your thinking.

2025 Strategy

Why Startup Founders Must Document Their 2025 Strategy Now

StartUp Founders: 2025 Strategy

Your Brain is for Ideas, Not Storage: Why Founders Need a Written Strategy

Hey Reader,
Founders: If I teamed up with your local bookstore to host some meetups - where I buy you a coffee, we share stories, do some founder therapy, and spark new connections - would you come? If so, click <a href="https://www.startuptoscaleup.com/startup-founder-coffee/">here</a>. 
For every founder building helpful, nice-to-have products that people like and might pay for. Are you essential? Without you, is the pain immediate and undeniable? With you, is the value obvious and compounding? Are you CORE?
CORE decides how easy you are to ignore in a sales cycle and push to the next quarter. CORE determines how quickly you'll be cut when budgets tighten. It's that simple.
The shift I am suggesting is from building features to engineering dependencies, from securing customers to creating champions, from surviving to thriving.
It's not all or nothing. Most solutions start by solving one problem, for one champion, extremely well. But to survive long-term, you must become indispensable. The faster you accelerate your journey to becoming CORE, the safer your business becomes.HYPER RELATED:
Every startup founder has, is, or will feel it. The gap between all the work you've done and the results you're waiting for. It's awful. It's universal. It's "<a href="https://www.linkedin.com/posts/jdsinclair_startup-founders-the-dip-startup-to-scaleup-activity-7263809676369158144-Odhd?utm_source=share&amp;utm_medium=member_desktop">The Dip.</a>"
LETS GET INTO IT:
CORE = Must-Have + Accretive Value + Deep Dependencies
None of this works without greatness. The foundation of CORE is a product that does what you say it will, and none of this is a substitute for <a href="https://www.startuptoscaleup.com/module1.8/">delivering</a> exceptionally.
<ol>
<li>Must-Have: Your product solves a problem your customer cannot ignore. It's not a "nice-to-have"; it's essential to their workflow or operation. Without it, something breaks.</li>
<li>Accretive Value: Your product delivers measurable ROI. It justifies its budget allocation by increasing revenue, reducing costs, or improving efficiency (or meeting a compliance requirement).</li>
<li>Deep Dependencies: Your product is integrated across your customer's operations that it's makes it extremely difficult to replace. Switching costs, multi-threaded usage, and organizational reliance make you sticky.</li>
</ol>
Even if you're a must-have and accretive, without deep dependencies, you're still at risk. 
It's why ecosystem marketplaces are so powerful. You use HubSpot, you want to move to Pipedrive but you have a few integrations via their marketplace delivering automations, workflows, and therefore the cost, time, and disruption outweigh the savings or additional features.
Without the integrations, you're a must-have + accretive value. With them, you've added deep dependencies across the organization. CORE.
SOL Score: Sh*t Outta Luck?
The easiest way to reconcile CORE is to ask how many steps it would take for you to be Sh*t Outta Luck (SOL)?
The SOL lens isn't just for retention. It's your sales playbook too. If you're easy to cut after the sale, you're just as easy to dismiss during the sales cycle. Designing your product to solve undeniable pain is how you win deals and keep them.
Said simpler. It's the cold emails that get replied to. They hit because they immediately communicate necessity. They solve a problem that's impossible to ignore. The closer you are to being indispensable, the more likely you are to win.
<ul>
<li>What happens if your internal sponsor leaves tomorrow? </li>
<li>Who would notice if your solution disappeared?</li>
<li>How many business processes would break? </li>
<li>How long would it take to replace you?</li>
<li>Would anyone fight to keep you?</li>
</ul>
This isn't about product-market fit or whether your product is good.
The question is about impact and indispensability. In sales, it helps you articulate why your solution is more than just nice to have. Post-sale, it's a reminder to deepen dependencies and embed yourself in the customer's workflows.
Every conversation, every pitch, every integration should move you closer to being CORE. Whether it's a prospect or a customer, the question is always the same: How catastrophic would it be to remove you? The more catastrophic, the closer you are to winning both the deal and hopefully retention.
The CFO Test....
VCs talk about "hair on the deal" as anything that makes a company less likely to survive scrutiny. Imagine the CFO walking into your customer's office and saying, "Cut your spend." Are you on the list? That's "hair on the deal" - a sign your solution lacks champions, deep dependencies, or irreplaceable value.
If you're easy to slash, lack internal champions, and your removal wouldn't cause immediate pain, you're at risk. Being CORE means people fight to keep you because removing you would break too much.
<a href="https://www.startuptoscaleup.com/module0.6/">Becoming Core: Must Have & Accretive Value</a>
Ignore CORE, Just Get In The Door....
You don't have to start as CORE. Most solutions don't.
Day 0 - your goal is simple: Get in the door. Solve one problem. Be liked. Get vendor approval, get through security, get paid, have a customer. That's your entrance. But once you're in, the mission changes. Every day becomes a relentless push to move from "nice-to-have" to CORE.
Here is how you might think about it:
<ul>
<li>Map Dependencies: Identify every process that touches your product. Then go create more! Build workflows and integration points across the organization and into the stack. More than just SSO.</li>
<li>Increase Pain Awareness: Make sure decision-makers feel the pain you're solving. Reports, dashboards, and ROI metrics make your impact undeniable. It is your responsibility to prove your solution value.</li>
<li>Build Moats: Every feature should increase switching costs. Every integration should make you harder to replace because of the increased value you deliver.</li>
<li>Create Champions: Spread your influence. The more stakeholders who depend on you, the more defenders you'll have when times get tough.</li>
</ul>
The Journey to CORE
Becoming CORE isn't instant. It's a journey:
Entrance: Solve one problem brilliantly and earn trust. 
Expansion: Prove your value across teams and use cases. 
Embedding: Integrate into workflows, operations and processes.
CORE: Become mission-critical. Visible to leadership and impossible to replace.
There's no middle ground. Stay relevent.
As always, if I can be of service, feel free to <a href="https://cms.startuptoscaleup.com/products/1-hr-start-up-consulting-call">grab</a> time. 
LFG.
-- James

Stop building nice-to-have products. Learn how to create solutions that become essential, deliver measurable ROI, and embed deeply enough in your customers' operations that you're impossible to replace.

Becoming Core

How to Make Your Startup Product Mission-Critical for Customers

StartUp Founders: Becoming Core

From Nice-to-Have to Mission-Critical: How to Make Your Product Indispensable

Hey Reader,
There's a part of the startup journey that's brutal and rarely mentioned. The Dip. The exact opposite of the adrenaline, excitement & energy of the beginning. The Dip feels like a deep, personal struggle, and yet, it's a universal founder experience. (<a href="https://ctt.ec/P1e4a" target="_blank">𝕏</a>)
The Dip isn't burnout. That's different. It's also not procrastination. That's avoiding (the right) work. The Dip is the lag between momentum and traction. When your adrenaline has burned out but reality hasn't caught up - the results of your work aren't coming in quick enough to maintain excitement.
You're doing everything mostly right but nothing seems to be moving forward. Small tasks feels massive and there is a total lack of energy coming back at you. You show up, do the work, and still feel like you're punching concrete. Every. Single. Day.
Ironically.... The Dip can be a good sign. You've survived long enough to meet it, that's a milestone most don't make. Not all founders who survive experience The Dip, and not all who experience The Dip survive.
HYPER RELATED:
<a href="https://www.startuptoscaleup.com/module0.3/" target="_blank">Extreme Uncertainty:</a> The Founder's Impact-Certainty Matrix is a powerful tool that helps you navigate extreme uncertainty in your startup. It allows you to balance the impact of your decisions and the certainty of their outcomes, making it easier to make high-stakes decisions quickly and effectively.
LETS GET INTO IT:
Ben Horowitz calls it "<a href="https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205" target="_blank">The Struggle</a>" where everything feels like it's on the line, and you're constantly tested to hold on when everything in you is whispering to let it go. Peter Thiel says building something from zero to one is always unique and lonely because there's no roadmap. A perpetual dip.
Procrastination during The Dip isn't laziness (it might be) - it's often self-preservation, your brain holding back from further taxing itself. Procrastination may be a red flag but might also be masking something bigger, fear of failure, feeling overwhelmed, not knowing where to start. In all scenarios this is your brain sending as clear a signal as it can. It needs a recalibration. Maybe listen?
You have to get through this, work like your life depends on it. It might. It did for us in <a href="https://en.wikipedia.org/wiki/Bleem!" target="_blank">'99</a>.
Why This Happens.
Your brain is literally working against you. That initial dopamine rush of having all the answers and feeling in control and putting in the high performance hours is just rocket fuel. It's what creates the initial launch but was never meant to power the whole journey.
The Dip happens when that dopamine falls away, but you haven't yet built the muscle memory that make this new reality feel normal. You're caught between what was and what will be.
Sound familiar? Everything feels harder than it should. You're going through the motions, mechanically executing tasks. The small wins don't have the same impact. You're questioning everything.
What To Do Now….
<ol>
<li>Acknowledge It: This isn't weakness. It's part of your founder journey, just a part that no one talks about. Name it. Own it. Stop pretending you're fine. It's not fine. </li>
<li>Protect Your Energy: Sleep isn't optional. Exercise isn't negotiable. Eat real food. Your body's fighting a war. Feed it accordingly.</li>
</ol>
There is always a move. There is always a solution.
~~~ The easy advice here would be to find your center, find what excited you at the beginning, find your roots, take a break, go for a run, eat more berries, embrace your <a href="https://www.startuptoscaleup.com/newsletter/embrace-ikigai/" target="_blank">ikigai</a>, re-anchor yourself. Cool. Sure. If that's all it took, it wouldn't be a dip, it would be a small divot in between having a bad day and eating some berries. ~~~
Start with these 4 things:
<ol>
<li>Change your success metrics. (Secretly) Adjust the expectations of what you can achieve. Clean your desk, have one call, send four emails, walk for 15 minutes. Whatever it takes. Humble yourself with some achievable metrics. </li>
<li>Break the Pattern. Insert something new into your routine a tangible change that creates some, tiny, bit, of, forward, momentum. Power hour of emails first thing, writing tomorrow's battle plan before bed, blocking your calendar so you have some peace. The actual new thing doesn't matter, the point is to disrupt your current shitty pattern and creatie a new one. Athlete training. </li>
<li>Get back in traffic. Most founders in The Dip isolate. It's the worst thing you can do. Go to a startup meetup, even if you hate the idea before you even arrive. Just do something. </li>
<li>Wartime CEO mindset. As Horowitz says, wartime CEOs can't afford to waver. They take the hard steps with conviction, they do the work, they do not fall, and they win.</li>
</ol>
The Dip isn't something you overcome, you have to grow through it. Every founder who's built something meaningful has gone through it, most go through it multiple times.
This isn't about who's smarter or works harder. It's about who accepts The Dip as part of the journey rather than fighting it as an obstacle.
The Dip is testing your commitment to your vision and your commitment to not fail.
How badly do you want this?
As always, if I can be of service, feel free to <a href="https://cms.startuptoscaleup.com/products/1-hr-start-up-consulting-call" target="_blank">grab</a> time.
LFG.
-- James

The Dip is the brutal lag between momentum and traction - when your adrenaline has burned out but results haven't caught up. Learn how to recognize it and grow through this universal founder experience.

Navigate The Dip

The Founder's Dip: How to Navigate the Toughest Part of the Startup Journey

StartUp Founders: The Dip.

Surviving The Founder's Dip: When Momentum Meets Reality

Hey Reader,
Everyone talks about IQ & EQ, but what about how you instinctively take action and solve problems? Who you are at your core is not really trainable or changeable, but it's often the hidden reason startups struggle to make progress in the early days.
It's the Conative Index and you care because founders often fight their natural tendencies, believing they need to act a certain "founder" way (move fast & break things). And when that isn't who you really are, you end up battling with yourself.
This isn't about skills or experience. It's about your instinctive approach to getting shit done – the underlying "you" that drives your actions and on which you build your knowledge and expertise.
TL;DR Founders who understand their natural tendencies and stop fighting against themselves are the ones who win. It's not about being right or wrong. It's not a competition. It's about understanding your strengths and building around them.

<h2>Why You Care…</h2>
Two things before you read this and smile or cry. First, it's an index, not a binary label. You might have elements of some or all of these modes. It's about how you lean. Second, this isn't about how well you actually execute. This is the how, not the how well.
It's Not a Competition (it is)
Founders think they need to be great at everything, and you kinda do, kinda. The real win isn't in being everything; it's in having everything. And you get that by not trying to be all of them, embracing what you are, partnering with those who complement what you're not.
The easiest way to explain it... Going to London next Wednesday. How do you pack?
<ul>
<li>Days in advance, researching weather and making lists? (Fact Finder)</li>
<li>Last minute, tossing it all together? (Quick Start)</li>
<li>Overpacking to be prepared for anything? (Implementor)</li>
<li>Organizing into neat categories? (Follow Thru)</li>
</ul>
It's how you naturally approach tasks. In all 4 scenarios, your experience will actually dictate whether you pack right. None of these is better or worse. The idiot thinks it's a competition, the intellect knows it's not.

<h2>Which One Are You?</h2>
Implementor Founders:
The one who makes it happen. Give you an idea, and you'll have a prototype built in your head before lunch and deployed by dinner. This is an insane strength and makes you the most sought-after co-founder. You learn through building, seeing, touching, and can do it with a speed that others dream of. You love to build. But, even the most brilliant execution needs a strategic direction. Are you building something people actually want?
When you partner with a visionary, it's game over. They'll provide the strategic roadmap, and you'll bring it to life.
Quick Start Founders:
The visionary is always thinking, always exploring – it's all about momentum and energy and moving forward. Speed, ideation, clarity and doing whatever it takes to get the win. But, do like to chase shiny objects, do like to run, execute, move on and at times struggles to isolate focus on the right goal? Often hard to translate into leadership and even harder to maintain the momentum.
When you partner with an Implementor who gets you, and a Follow Thru to ensure it's executed with detail, the results are extraordinary.
Fact Finder Founders:
You're data-driven, knowledge-driven and thrives on information. You like to understand the destination before jumping in, the process, the learnings, the why. It takes you a moment, but when you get there, it's magical. You find insights no one else sees and you can make strategic choices with the ideal combo of data and gut. But, speed is critical. Analysis paralysis and letting 'perfect' be the enemy of 'good' are always the demons you battle.
When you partner with domain experts (or if you are the SME) and an action-taker, your knowledge of the market changes the odds dramatically in your favor as you just have a closer pulse of "right".
Follow Thru Founders:
You like to know or do know, how it plays out. The systems, processes, and flows. You bring order to chaos, you create structure, predictability, and enable accountability. You build process so the founding team is not 24/7 putting out fires and can focus on what matters. It's a magical skill. But, flexibility is key. Sometimes the inability to work outside the "book" or the "process," or being stubborn about a way or a purist about a method, shackles innovation, creativity, and the capability to execute.
Put you in any company, and if you can adapt, innovate, and leverage systems as guidelines, everyone has less anxiety, is hyper focused on the objectives, and a clearer path to executing on the strategy. Customers often see the biggest impact.

<h2>Managing It...</h2>
Misalignment: Reading this and believing you are one or the other, or that one beats the other, is a waste of time. It never works, you can only fake it for so long.... because it's not instinctive.
What to do: Take the Conative Index. Be clear on who you are, get off autopilot and embrace your natural tendencies, your strengths.
Blind Spots: (Your Individual Limitations) Without knowing your mode, you miss massive blind spots in your own capability to execute. You need the others in some capacity.
What to do: Ensure there are people around you filling those gaps. Could just be a project manager or product analyst for a few hours a week to ensure your vision is grounded in truth and executed how you want. Build a framework that supports your strengths. Quick Starts need checkpoints. Fact Finders need deadlines.
The Mismatch: (Core Team Composition) Founders often hire people just like them. Two Fact Finders will make excellent research partners but struggle to execute. Two Quick Starts may launch fast but burn through resources without results.
What to do: Hire for your gaps (co-founders, early employees), actively fight to find those with different modes.
Know who you are, move faster, make better decisions, higher more impactful people and burn out less. Lean into your strengths, cover your weaknesses, and watch.
As always, if I can be of service, feel free to grab time.
LFG.
-- James

Learn how founders who understand their natural tendencies and stop fighting against themselves are the ones who win. Discover your conative index and build around your strengths.

Conative Sabotage

Discover Your Founder DNA: The Conative Index for Startups

StartUp Founders: Conative Sabotage

Your Founder DNA: Understanding Your Natural Operating Mode

Hey Reader,
Just like that, without realizing it, you go from founder to NPC. From having a clear vision, some moxie, and a bold idea, to being pushed into normalcy as the market never stops telling you that you're doing it wrong.
NPC often happens in moments of desperation, where you stop (or are forced to stop) critically evaluating, questioning, investigating, and instead go with the flow, follow the popular, execute the so-called "right" advice. Just like the background characters in video games.
This isn't hyperbole. It's an epidemic. (Yes, the irony, claiming not to be hyperbolic, then using hyperbole.)
(NPC. Non-Player Characters. The background nobodies in video games not controlled by players, the ones with no agency.)
TL;DR NPC thinking isn't inherently bad. There's a time to follow the script and a time to rewrite it. Your job is to work out which, when & where.
<h2>It's Almost Impossible.</h2>
This is not a contrarian conversation, it's principled decision making, and it is so impossibly tough to do. It's not like you try to become an NPC. It just happens. The market has a way of wearing you down.
You're not telling a VC to back off, even if their advice derails your vision.
You won't stop a customer from requesting a feature when they're about to sign.
We all do it. Because we can't afford not to. Because we are desperate. Because we are scared it might turn into a no.
The era when everyone was building chatbots or when growth hacking was the only marketing playbook that mattered or when every pitch deck had to have a hockey stick graph? That's NPC in action. Sure, worked great for some founders, but most who just followed the keyword crowd crashed, because it just wasn't authentic to their startup.
Sound familiar?
<h2>NPC Thinking & You.</h2>
Uber did this, Zuck did that, Lenny said this, YC startups do that, all of it, feeding you their story disguised as good advice. And it is good advice, great advice even. Theirs. Not yours. And that's just the outsiders.
Insiders too. Customers asking for features you don't want to build. Engineers pushing for a refactor. Advisors with suggestions. Prospects demanding useless additions. Everyone wants to mold you into their version of a founder.
Other founders parroting the same pitches, with the same investor deck template, same outbound tech stack, same buzzwords, same whateves, building the same forgettable products.
Every accelerator, pitch competition, and "disruptive" startup is one in an army of clones. We are "the Uber for X" or "AI-powered blockchain solution" - You recognize the script, because you've been reciting it.
Even me. Every week, I send a strategy, a thought, a question. Playbooks, pricing, tactics. I fight hard not to give advice, but instead ask you reasonable questions I think you should be able to answer. I am just another voice with a view.
NPC thinking is a scapegoat that lets you avoid the hard questions, because you're following best practices. But.. you are losing your voice and worst of all, it's making you, by mistake, reactive.
<h2>Back. To. Basics.</h2>
When do you follow, when do you iterate, make yours, adapt, disrupt? Impossible to answer, but here's a view.
Universal truths might be safe, but they're not game-changing. Best practices are brilliant, playbooks are helpful, but you have to fight to keep what makes you uniquely you.
Your job is to know when to follow them, when to adapt them, and when to ignore them. Copying the safe moves is a strategy, just likely not a winning one, and you should probably still do them. But the wins normally come from the unique decisions only you can make.
NPC thinking is comfortable. It's safe. It's what everyone else is doing. Safety. Does. Not. Win.
It all comes down to a this. Are you doing what is the "right" thing to do, or what's right for your startup, your vision, your customers?
This is not a founder pep-talk, I'm just asking, are you the protagonist in your story?
I know. A really shitty, impossible, paradox of a newsletter to read on a Sunday.
Sorry. Not sorry.
As always, if I can be of service, feel free to grab time.
LFG.
-- James

Learn to balance industry best practices with your unique vision. Discover when to follow the script and when to rewrite it for your startup's authentic success.

NPC Mode

Startup Founders: Avoiding NPC Mode to Build an Authentic Company

StartUp Founders: NPC Mode.

Escape Founder NPC Mode: Finding Your Authentic Voice

Hey Reader,
There's a whisper we are seeing in SaaS, that improving productivity of your users, or automating functions normally done by users, leads to them buying fewer seats. The irony of building a fab product....
We are seeing the emergence of usage-based pricing expand beyond traditional models (like API & Platform) into new areas, along with the rise of outcome-based pricing. It's not universal, it's not absolute, but it's not not happening.
If Salesforce is the bellwether for the industry, then this shift is likely inevitable.
<ul>
<li>Usage-Based Pricing: Pay based on the volume or quantity of resources or services consumed. (API, time, tokens, action, edit, credits)</li>
<li>Outcome-Based Pricing: Pay based on specific, measurable results or outcomes achieved by the service. (autonomous resolutions, machine, delivery, completed tasks or packages)</li>
<li>Hybrid Models: Combining elements of seat-based, usage-based, and outcome-based pricing (Seats+PAYG / Human+Machine)</li>
</ul>
BUT. Keep pricing clear and simple. If your customer has to ask a question, that's a friction point, and friction rarely leads to conversion. Your customer is likely used to buying a seat - aka "buying access" to your solution.
Whatever model you choose, it's not about choosing between legacy vs new, but for your customers, it might feel that way. They, like you, need predictability in spend. New models mean new risks, and the biggest challenge is making sure it's understood.
As you explore alternatives to seat licensing, even in hybrid form, there are merits in using it to get your first customers across the finish line - no commitments, just pay for what you use, give us a try.
The argument for startups could be the lack of early predictability in revenue, unlike MRR where you know exactly what's dropping on the first.
When done right, despite the variability, usage/outcome pricing can lead to higher overall revenue as customers scale their usage. Growth by increasing ARPU (Avg Revenue Per User). Focusing on extracting more revenue per user rather than solely expanding the user base can help flatten CaC.
There's also the success paradox that as you start charging for success, and it starts working, customers start to question its value. The better your product performs, the less effort it seems to require. Frame pricing around the value of the outcome, not the effort involved in achieving it.
I am liking the sidecar to your existing seat model. Offering a small "pay as you go" option to test the waters. Model it out, understand the metrics, and get your head around it before going all in. I understand for startups already in market, this move likely has technical and observability costs.
Why This Is Happening:
Value Alignment: Founders (& Incumbents) are realizing that seat-based pricing doesn't always reflect the value they provide. For value-driven products, the model is increasingly seen as misaligned with the outcomes they deliver.
Customer Demand: As budgets tighten, customers are pushing for pricing that reflects their actual usage and realized value, No one wants to pay for a dormant seat license or a monthly sub they use 5 times a year.
Competitive Pressure: As giants like Salesforce experiment with usage-based models, it's creating a ripple effect across the industry. You need to at least be prepared to have a position.
Technical Advances: Better analytics and tracking capabilities make it easier to implement and manage usage-based pricing and provide that transparency to customers.
Why do you care?
<ol>
<li>Future-Proofing: Understanding these models now prepares you for potential market shifts.</li>
<li>Competitive Edge: Being early to adopt could differentiate you in a crowded market.</li>
<li>Growth Potential: These models can unlock new growth vectors and customer segments.</li>
<li>Investor Expectations: As the market evolves, so do investor perspectives on pricing strategies.</li>
</ol>
Customer education is expensive, so any model that's not seat-based should probably come with a calculator. It likely requires reframing your marketing to focus on the value or job that gets done, not just on what customers are getting.
Don't jump on the bandwagon. It's about understanding a shift in the SaaS landscape and being prepared to evolve if and when it makes sense.
The goal isn't to be cutting edge – it's to be effective. A model that best aligns with your customers and your startups needs. Win-Win.
For those thinking of leaning in to this new pricing strategy, just remember, it's all an experiment, you are trying to get more right than wrong. Just try to make an informed decision, not a reactive one.
As always, if I can be of service, feel free to grab time.
LFG.
-- James

SaaS companies face a paradox: better products automate away users. Learn how to adapt with usage and outcome-based pricing models that align value with cost and increase ARPU.

Units Of Work

SaaS Pricing Evolution: Moving Beyond the Seat-Based Model

StartUp Founders: Units Of Work

Beyond Seat Pricing: The Shift to Usage and Outcome-Based Models

Hey Reader,
StartUps are built on a foundation of assumptions. Some are spot-on. Others, pure delusion. As a founder, it's hard to tell the difference. Not because you're reckless or ignorant. You're just so deep in your solution that you lost perspective.
Whether you're two weeks or two years into your journey, you need the courage to continually return to first principles. Are the assumptions we made yesterday still true today?
If you are pre-launch or just launched and hearing crickets. It's more likely than not, that you're hiding some flawed assumptions.
This is the assumption detox.
Amidst the mayhem of making something out of nothing, it's easy to lose sight of a foundation upon which your business stands - your assumptions.
The assumption that crushes most startups? That the best product wins. It doesn't. The team capable of learning the quickest, iterating, and repeating wins. The founder who understands that distribution beats product excellence - that's who wins.
It's one of the benefits of a co-founder. They don't let you get away with flawed assumptions. They force you to quantify your position, defend your thinking, and be thorough.
It's why a tribe of mentors & advisors matters - to check and challenge your assumptions.
It's why pivots happen - because someone had the courage to question the foundational assumptions of the business.
Without these external voices - if you're a solo founder or working in isolation - you have an even greater duty to rigorously qualify, quantify, and interrogate your assumptions. You must be your fiercest critic, constantly questioning and fighting against your own biases.
Forward-looking growth assumptions aren't inherently flawed. They're essential, if they are grounded in some reality and constantly tested. A balance between ambition and realism, with the guts to adjust course when necessary.
So, just for a second, can we go back to the beginning?
This isn't about second-guessing yourself into oblivion. It's clarity. Separating intuition from unfounded assumptions, real market insights from your personal biases.
Does the problem you set out to solve still exist? Can you prove it? Are people actively searching for a solution to this problem? Can you prove it? Are people willing to pay for a solution to this problem? Can you prove it? Is there a viable mechanism for your solution to be heard by this audience? Can you prove it? You get the idea.
Assumptions come in three flavors:
<ol>
<li>Blind Spot Assumptions: Silent killers. The ones you've inserted into your narrative without even realizing. Not because you're stupid, but because you're human. They feel like common sense or obvious truths.</li>
<li>Cornerstone Assumptions: The necessary gambles. The big bets, the assumptions your entire strategy is built on. You're hyper-aware of the risk. The ones that, if wrong, tank everything, but you're betting on it anyway.</li>
<li>Unnecessary Assumptions: The distractions. The "what ifs" and "we needs" that distract from the core. Often, they involve thinking too far ahead when you haven't even validated your core idea.</li>
</ol>
The danger is when a Blind Spot Assumption is actually a Cornerstone Assumption. When something you haven't even recognized as an assumption is fundamental to your entire business model.
As a solo founder, how do you strip away years of accumulated "knowledge" and get back to first principles?
Answer One: With a lot of difficulty. (fact)
Answer Two: Get systematic about it.
<ol>
<li>Blank Slate: What questions would you have for a friend thinking about starting the same business? Imagine you're starting your startup today. What would you NEED to know to quantify or qualify that this is a good space to enter and devote the next era of your life to?</li>
<li>Assumption Audit: What do you "know" about your market, customer, product. Everything.</li>
<li>
Categorize: (Across your stack of knowledge): <ul>
<li>Is this a Fact (proven with recent data)?</li>
<li>Is this Intuition (based on experience, but not tested)?</li>
<li>Is this a Blind Spot Assumption I've never questioned?</li>
<li>Is this a Cornerstone Assumption I'm aware of and building upon?</li>
<li>Is this a Legacy Belief (maybe true once, but not checked recently)?</li>
</ul>
</li>
<li>Prioritize: Which Blind Spots, if wrong, derail you? Which Cornerstones need urgent validation?</li>
</ol>
You know the drill from here. Test, Iterate, Repeat.
This audit/detox is part of the founder playbook. Not a moment in time or a quarterly thing. A mindset, a constant state of questioning and learning.
The market only cares about value creation. Not your assumptions, not how long you've been working on your idea, not how much you've invested. Just VALUE.
And it is very difficult to create real value if you're operating on outdated or unfounded assumptions.
This process is uncomfortable. It might force a return to the drawing board, a drastic adjustment. Good. Better to know now.
The flip side is you might also discover new opportunities, a new or bigger market, or that a slight pivot could unlock something better. That's what you are really hoping for.
This is how great founders operate. They're not afraid to go back to basics, to challenge everything they think they know. They run this playbook again and again, always staying connected to first principles, always grounding their decisions in current market realities.
So. Transform guesswork into strategy, assumptions into insights, stagnation into growth.
Returning to first principles isn't a sign of starting over. It's a sign that you have the capability, the maturity, to question everything. Especially the things you're most certain about.
That's what gives you the title of founder.
As always, if I can be of service, feel free to grab time.
LFG.
-- James

Every startup is built on assumptions. Learn how to identify and challenge the ones holding you back with this systematic approach to questioning what you think you know.

Assumption Detox

Startup Assumption Detox: Identifying Hidden Mental Models

StartUp Founders: Assumption Detox

The Startup Assumption Detox: Challenge Your Mental Model

Hey Reader,
The biggest lie, after the diamond industry, greeting cards, and the middle choice at the gas pump, is that you can't have it all; fast, cheap, good - you must pick two. It's a phenomenal sales slogan because it sounds reasonable, but..it's complete bullshit.
Turns out, the people most equipped to execute this trifecta are founders, the ones with a to-do list longer than a CVS receipt.
There are two types of founders: those who make things happen, and those who wonder what happened.
TL;DR Think galactic, act atomic. Break down your "thing" into bite-sized, reasonable, feasible, actionable steps so every small task gets you closer to the goal. It's just a matter of practice.
RELATED:
The Phantom Product Market Fit &gt;&gt;
LETS GET INTO IT:
The startup landscape is shifting back in founders favor, just with a need for a touch more precision than the "move fast and break things" era. Conversations have become hyper-focused on action.
Think Big, Work Small. You're probably already doing this without realizing it. You've got this ridiculous vision, this massive idea, you're nudging it forward. Incrementally. Relentlessly. (especially you marketplace founders).
The trick is to create a cascade of focus, from your vision all the way down to your daily grind.
Early days, this is your model, making sure the daily grind gets you closer to the bigger strategy, As you mature, sure OKR's and all the jazz, but for now, the focus is on action.
This is OPPM - One Page Project Manager. Yes, i just sent you a newsletter asking you to consider a methodology for getting stuff done. Yes, NASA uses it.
Yes, it means admitting you need a plan. But you probably do, your brain is an AWFUL to-do manager.
OPPM is a single, visual page that captures your entire strategy, from the big vision down to the weekly tasks that will move you forward. That simple.
It's hard to be angry at a broadly achievable plan that's flexible enough to change.
Before we dive into the workbook, let's take a moment of silence for the other startup archetypes. Of course, you're none of these:
<ol>
<li>Think Big, Work Big: The "waterfall" approach. Coherent big-picture strategy, but no incremental delivery or experimentation.</li>
<li>Think Small, Work Small: Agile newbies. No coherent bigger picture strategy. Small, scattered tasks lead to incremental, but insignificant progress with no real impact.</li>
<li>Think Small, Work Big: Over-engineers. No coherent bigger picture strategy. Large, unstructured efforts lead to massive work without a release in sight.</li>
<li>Define Big, Work Small (Poorly): They break down big projects but miss the strategic connection. All tactics, no strategy.</li>
</ol>
Your goal? Think Big, Work Small (Effectively): Maintain a clear, ambitious vision while executing through small, iterative steps.
So, what does this mean for you?
Here's how:
<ol>
<li>Have your north star, your goal of goals.</li>
<li>Have a clear goal: Know where you're going. Make it big, make it bold, make it slightly terrifying. But make it within the next 90 days.</li>
<li>What 4-5 objectives have to happen for you meet that goal.</li>
<li>What 4-x tasks have to happen for you to meet that objective.</li>
</ol>
Work backwards if you do all the tasks, do you meet the objective, if you meet all the objectives do you meet your goal, if you meet your goal does it move the needle on your goal of goals…. thats it.
As always, if I can be of service, feel free to grab time.
LFG.
-- James

Master the art of thinking galactic while acting atomic. Break down your vision into bite-sized steps that compound into success. NASA-approved planning for startup founders.

Think Big, Act Small

Think Big, Act Small: The Startup Execution Framework

StartUp Founders: Think Big, Act Small

Hey Reader,
Extreme uncertainty is literally the MO of StartUp Founders. Make decisions that are hopefully on the righter side of right, praying that when you hit, the impact moves the needle.
There's no playbook, no perfect formula. Don't get caught up in finding the right way to do things. Just get out there and build, with a touch of structured intention.
TL;DR Even gut decisions need a framework to drive resources towards actions with the potential for high impact and some level of certainty.
LETS GET INTO IT:
At some point, you'll need to reconcile how you make decisions.
Not to kill your vibe or passion, not even to bring order to the chaos. It's just a personal exercise, a mental model to help you keep on keeping on as your decisions multiply in complexity and impact.
Chaos has merit. It's how we got here. But... When you're overwhelmed, procrastinating, not gaining traction, it might be time to shift gears.
The transition from "founder with a vision" to "founder building a business."
No one is looking to slow you down or kill momentum. It's adding a touch of method to the madness. Perhaps, make decisions faster, with more intention, sleep better (occasionally), and understand why you're doing what you're doing.
Even chaos needs a roadmap.
This isn't organizing or micro-managing day-to-day decisions - features to prioritize or channels to test or which messaging will resonate. Those have tactical frameworks that tend to be right. This is about the big, macro go/no-go decisions for you, the founder, the trajectory creator.
We got here via gut, luck, accidents, and audacity. Founder bravado. But as the stakes get higher, managing that chaos with will power becomes impossible. You become the blocker.
This is the inflection point where you realize that chaos may have got you here, but it will not get you past those first few customers.
No one is stifling your creativity or forcing you into a flowchart. It's not about having all the answers, it's about asking the right questions at the right time.
Pick a framework, any framework, it doesn't matter. What matters is having a consistent way to measure your decisions. It's a grounding tool.
My framework? The Founder's Impact-Certainty Matrix.
So, what does this mean for you?
This is just a forced question to ask yourself as you plan your day, map your priorities, and make sure the work you're doing COULD actually move the needle.
EXPLORE (High Impact, Low Certainty): This is your testing zone, skunk works, crazy, not crazy, who really knows zone. Run experiments, validate assumptions, and allocate time and energy to exploring. It's risky, but innovation lives here.
EXECUTE (High Impact, High[er] Certainty): You've got data, you've got validation, you've got neither but you have some signals – stuff that if you do, it is likely to generate some results. Execute ruthlessly.
AUTOMATE (Low Impact, High Certainty): The necessary evils. Automate, delegate, or systematize these tasks before they become your day job as soon as you understand what needs to happen and how.
IGNORE (Low Impact, Low Certainty): The shiny, sound urgent, might be urgent for someone else, but not for you, not right now. Learn to say no, to yourself and others.
Perhaps, today, categorize your decision, your time, your priorities, against this matrix?
EXPLORE: What experiment will validate your riskiest assumption?
EXECUTE: Name three actions that will tangibly move your core metrics.
AUTOMATE: Identify one task sucking your time that you can systemize or delegate.
IGNORE: What "urgent" distraction can you kill to buy back your focus?
As always, if I can be of service, feel free to grab time.
LFG.
-- James

Master the chaos of startup decision-making with the Impact-Certainty Matrix. Categorize decisions as Explore, Execute, Automate, or Ignore to maximize impact.

Extreme Uncertainty

The Founder's Impact-Certainty Matrix: A Framework for Startup Decision Making

StartUp Founders: Extreme Uncertainty

The Founder's Impact-Certainty Matrix: Navigating Startup Chaos

Hey Reader,
The entire journey of trying to get your StartUp off the ground is so you can delegate something to someone else. Right? That's scalability.
Wrong. Dead wrong.
That thinking often comes from smart, experienced people who think they understand what it takes to manifest something from nothing, but they don't get that founders are a different breed.
RELATED:
<a href="https://www.startuptoscaleup.com/startup-scaleup-newsletter/the-first-time-founder-superpower-ignorance-on-fire/" target="_blank">First Time Founder</a>: Ignorance On Fire <a href="https://www.startuptoscaleup.com/startup-scaleup-newsletter/founder-glow-up-with-all-your-sht-youre-still-the-best-ceo/" target="_blank">You're The Worst CEO:</a> Founder Glow Up <a href="https://www.startuptoscaleup.com/startup-scaleup-newsletter/founder-evolution-or-extinction-theres-no-middle-ground/" target="_blank">Founder Evolution:</a> ....or extinction
LETS GET INTO IT:
Paul Graham had a fire piece last week calling it "<a href="https://paulgraham.com/foundermode.html" target="_blank">Founder Mode</a>" that's making the rounds, giving a lot of founders the confidence to finally say it: manager mode is damaging, they want to stay in control.
The experience of one top performer with a billion-dollar company doesn't always translate to the rest of us. This isn't a "copy Chesky" playbook. It's about aligning some of his thinking with your reality, finding ways to run faster, stronger, better...on your own terms.
Most founders are already in 'Founder Mode' relentlessly revising five words on the website, obsessing over every detail, in the absolute weeds of your product and battling doubts because you're staying true to your vision.
Chesky is not alone. Jobs returning to Apple, Musk sleeping on the Tesla factory floor and countless founders you have never heard of already doing whatever it takes to make magic happen.
Founder Mode means being deep in the weeds of everything, bringing your eyes (vision) and heart (passion) into every single decision. Yes, ITB vs. RTB, yes, allocating your time where it has the most impact, yes to relentless focus. But above all, it's about absolute ownership of your sport.
It's about being the force of nature that only a true founder can be.
It's not as simple as "Founder Mode good, delegation bad." It's also not Founder Mode = Megalomaniac Dictatorship
The Conventional Wisdom: As you scale, hire good people and get out of their way. Build a "real" company.
The "Founder Mode" Approach: Maintain direct control. Fewer things, done better. Leverage founder superpowers longer.
The Reality: It's not black and white. There's a spectrum, and where you fall depends on you, your capabilities and circumstances.
What does Founder Mode really mean?
<ul>
<li>Being so involved that your team thinks you're crazy…until it works.</li>
<li>Bringing your vision and passion into every single decision.</li>
<li>Breaking "good management" rules to get your vision across.</li>
</ul>
Your deep involvement isn't a weakness. Your speed to decision making, your clarity of the market, your fight for velocity. It's your superpower. Your obsession with details isn't micromanagement. It's how you build something truly great. And non-founders can rarely deliver that on your behalf.
Is it scalable? No. Is it exhausting? Absolutely. Is it the only way to build something that changes a market? Probably. But only if you can pull it off.
Founder Mode isn't for everyone. It works for exceptional founders, true pirates.
Founder Mode is not an excuse for your bullshit...
- Needlessly micromanaging every detail - Creating a revolving door of talent - Expecting founder-level dedication without founder-level compensation - Getting angry when things don't go exactly your way
You're doing it wrong.
Founder Mode is about vision, passion, and execution. It's not a free pass for bad leadership. If you're using it as an excuse for toxic behavior, you're not in Founder Mode – you're just being terrible.
Real Founder Mode means taking responsibility, not shirking it. It's about elevating your team, not crushing it. It's about making hard decisions, not throwing tantrums.
If you can't tell the difference, you might not be cut out for this. Harsh, but true.
So, what does this mean for you?
<ol>
<li>Know Yourself: Are you a visionary or do you need to build systems that empower others to act like founders?</li>
<li>Align, Align, Align: Whether you're hands-on or hands-off, your primary job is alignment, everyone pulling in the same direction.</li>
<li>Culture Is Real: If you can't (or shouldn't) micromanage everything, build a culture that makes the right decisions without you.</li>
<li>Play To Your Strengths: If you're great at vision, do that. If you're better at brute force alignment, do that. But you must drive alignment, speed, agility, and vision somehow.</li>
</ol>
You're not here to run a company. You're here to build a brilliant company.
Just be the best founder you can be - whatever that looks like for you and your startup.
Your investors might freak out. Your team might get uncomfortable. It's part of the journey.
LFG.
-- James

Conventional wisdom says founders should delegate as they scale, but Brian Chesky and other visionaries prove the opposite. Learn when to maintain direct control and how to leverage your founder superpowers.

Beast (Founder) Mode

Founder Mode: When Visionary Founders Should Stay in Control

Every Founder/StartUp Needs A Newsletter. Communicate authority, deliver value, and nurture relationships. Whether you're building in public, establishing expertise, or growing your audience, a newsletter is key to sustained engagement.

ConvertKit

StartUp Founders: Beast (Founder) Mode

Embracing Founder Mode: When to Stay in the Weeds

Hey Reader,
Remember when you thought building the product was the hard part? Cute.
The second your product hits the market, a whole new attack sequence starts. Suddenly, everyone's fighting to steer you off course - including yourself.
You're juggling shiny objects, must-have features, demanding customers, and new idea grenades. Straddling sales, product & operations is both your superpower and your kryptonite.
LAST WEEKS FRAMEWORK:
0.2 <a href="https://www.startuptoscaleup.com/module0.2/" target="_blank">Traction x Fame Curve</a>: Anywhere But Red (<a href="https://www.linkedin.com/feed/update/urn:li:activity:7235366891530113024/" target="_blank">Join Convo</a>)
LETS GET INTO IT:
Most founders, the second they hit market, try to please everyone, chase every "opportunity", and end up building a Frankenstein that in an effort to solve everything for everyone, solves nothing for no one.
Don't be that founder.
Sound familiar? Your engineers want two sprints for technical debt. Your sales team (you) is promising features your prospects want. Engineering wants you to sell what they already built. Your customer that is acting as a reference is demanding a feature. Your internal systems are built with silly string.
The pressure to prioritize growth at all costs can lead to a reactive "feature factory" mindset, where the pursuit of short-term gains overshadows long-term vision and customer-centricity. And the only metric anyone seems to care about is growth (at least for now).
You have an impossible job that only works if you have the patience, strength, discipline, and resilience to be moderately right about when to maintain course vs. when to make an adjustment.
It's not about stubbornness. It's about being strategic. Knowing when to hold the line and when to pivot. Making conscious choices that align with your vision - not reactionary decisions that turn you into a feature factory.
Navigating The Forces
<ol>
<li>Know Your Quadrants: Categorize decisions into Vision Investments, Game Changers, Quick Wins, or Nice to Have. You have to shield against shiny object syndrome.</li>
<li>Recognize the Forces: Core strategy, market pressures, internal dynamics - acknowledge where the demand is originating, without ceding control.</li>
<li>Filter Like Your Life Depends On It: Does it align with your vision? Can you execute it? Will it delight your ideal customer? If it's not a hell yes, it's a no.</li>
<li>Decision Point - Hold or Adjust? Sometimes, holding the line is the bravest move. Other times, a strategic pivot is the only move. Learn to tell the difference.</li>
<li>Maintain Your Skunkworks: Keep innovating, have an experimentation pipeline, but don't let it derail your main mission.</li>
<li>Calculated Risks vs. Necessary Compromises: Recognize when a calculated risk is needed to seize an opportunity, and when a compromise, though not ideal, is necessary for the greater good.</li>
</ol>
You're not here to build features. You're here to solve problems and deliver value (<a href="https://www.startuptoscaleup.com/module3.0/" target="_blank">outcomes</a>). Don't let short-term pressures derail your long-term vision. Unless, of course, they absolutely have to...then do whatever it takes.
What Now?
Here's a pro-tip you probably won't do:
Every time a ticket goes from your backlog into sprint, add these 6 fields:
<ol>
<li>Date: When the decision was made.</li>
<li>Decision Made: Concise description.</li>
<li>Quadrant (Impact/Effort): Categorization based on impact and effort.</li>
<li>Rationale: Core reasoning behind the decision.</li>
<li>Expected Impact (Numbers, Not Feelings): Quantifiable anticipated outcomes.</li>
<li>Review Date (Reckoning): When you'll review the decision's effectiveness.</li>
</ol>
If you build a feature that 90 days later has not met the expected impact, it's time for a reckoning. Was the rationale flawed? Did the market shift? Did you execute poorly? This honest reflection is where real growth happens.
Why won't you do the pro-tip? You don't actually have the mechanisms in place to be able to measure the impact of a specific feature. You still don't have <a href="https://www.startuptoscaleup.com/module3.2/" target="_blank">observability</a>.
This isn't busywork. It's forcing your to ask fair questions about your own decisions.
Stay focused, stay strategic, and for f's sake, hold the line.
-- James

Post-launch, founders face pressure from all sides. Learn when to hold the line on your vision vs. when to pivot - a strategic framework for making product decisions with confidence.

Hold The Line

Startup Strategy: When to Hold The Line on Product Decisions

The StartUp To ScaleUp framework gives founders a methodical approach to navigating early-stage decisions.

StartUp To ScaleUp

StartUp Founders: Hold The Line

The Strategic Founder: Knowing When to Say No

Hey Reader,
Despite the predatory fundraising p*rn on your insta feed claiming you're funding ready & they can help. You likely aren't, can't & won't. So, let's pivot to what actually matters. What now?
Money has changed in 2024. You need fame, traction, or a bit of both. The occasional startup raises millions with neither. But that's lightning striking twice or a rich uncle that loves you.
TL;DR The only early-stage metric that matters is PROOF. Can you show that you can create something people want and will pay for?
LAST WEEKS FRAMEWORK:
4.6 StartUp SaaS Pricing: Low End Of Normal
LETS GET INTO IT:
Funded or not, the goal is the same. Build a business more likely to succeed than fail.
The only true currency is evidence, something we all lack in the early days. Real proof doesn't have to be massive. It's about anything, even the tiniest signal, that adds a grain of credibility to your vision.
A single passionate user, an industry expert's approval, a scrappy prototype that shows technical feasibility. It's not about scale; it's about that first flicker of validation that makes you think this might actually work.
Proof is what attracts talent, keeps you sane, secures partners, and wins early adopters. Even if it's just a spark, if it's the right spark in the right context, it ignites everything.
Evidence isn't the pre-requisite to funding; it is the funding. No founder bias, no explanations – just fact.
Building proof is every interaction with a customer, every tweak to the product, every partnership, every anything should add to the credibility you're building. It's this consistent, iterative effort that turns small wins into real evidence.
Early days, this proof comes in two flavors: Traction and Fame.
Traction is the core. It might be early users who rave about your product. It might be revenue, a pre-launch list, successful outcomes, the tech working, anything showing demand or impact of the solution.
Fame is the spark. It's influence, but functional. You're a domain expert, have deep experience with the problem, prior success, a notable name, or work at a relevant company. It's founder-market fit.
Establishing your reputation as a credible expert in your domain can be just as powerful as traction.
Pre/Seed/Angel… You don't need both. But you sure need one.
Your job is to build that evidence. Every. Single. Day.
Traction X Fame > Where Are You On the Curve?
What Now?
Every single day... "What can I do today to prove we're real?" Do it. Then do it again tomorrow.
Investors bet on evidence, and you and your employees are likely your largest investors… so prove it to yourself.
It's normal to feel like you're in the 0 phase (the wilderness), traction and fame seem elusive. Every successful founder started at zero and has navigated this phase. Persistence to find a spark that ignites everything.
So stop chasing and start building something so undeniably awesome that they'll be knocking down your door.
Stay hungry, stay foolish, but above all, every day, one more step towards PROOF.
As always, if I can be of service, feel free to grab time.
-- James
Off topic. I'm thinking of converting all these modules into a cohesive live course, from idea origination to first customers, literally pebble by pebble. Would this be helpful? (also, if you're a wizard at this stuff, reach out)

For early-stage startups, investors demand proof. You need either traction (customer validation) or fame (industry credibility) to stand out. Building evidence daily is your path to success.

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About the Author

James Sinclair