StartUp Founders: Cause Problems

Hey Reader,

So many founders, way too early, before they truly know their ICP, their pricing, their product, their channels, their anything, get a tiny bit of traction, and then start racing to normalcy.

Implementing systems and processes trying to stabilize the ship. The thinking is that the mayhem you're running is unsustainable and fixing that is the priority.

It rarely is the priority.

In 2023 I wrote embracing chaos:

"92% of your company is virtually identical to every other firm in your sector. Hidden within the day to day, you'll find your unique 8%: the spark that ignites your proprietary IP, gets your customers excited, your secret sauce."

This is the tactical reality, if you are not directly causing at least 20% of the problems in your company, you are not taking enough risk. By 20% I mean some, but not too much, but enough to have impact. It's directional, not literal!

...and that 20% of problems, the exploring, the finding, the new learnings, the hunch, the ish signal. That's where the 10x feature that leapfrogs your solution ahead comes from.

The key however is about what chaos you are looking to get under control. A majority of your mayhem right now is external. Right?! Customer complaints, bugs in prod, schizophrenic KPIs, team cohesiveness issues, slow sales.

All firefighting. And you need some percentage of the other kind of problem. Building. And you cannot confuse the two. What made you dangerous yesterday must remain tomorrow...

You most likely are trying to stabilize when you don't really have all the answers yet. You certainly don't have PMF because you can't, it's a temporary outcome the market gives you, until they don't.

There are two kinds of problems and most founders only have one of them, the one they think they need to fix, is real, but... This is about the other one.

THE PROBLEMS YOU'RE PRIVILEGED TO HAVE (PASSIVE PROBLEMS)

You can't apologize to a customer you don't have. Not a great mantra, but it's true. Complaints can only come from someone who believed you could solve their problem. Bugs can only come from users actually using the thing. So you are privileged to have them!

IN FACT I would double down, that having customers complaining is a deeply great sign that they see true value in what you are building and where you are going, they just want it to work vs choosing not to escalate and churning.

Standard firefighting aren't wrong problems, they're growing pains as you figure it all out, the point is to ensure this busy work (RTB (Run The Business)), the work you're doing to stay afloat, is not the only work.

Do the important busy work. Do the stabilizing work. We all have these problems. We all have to try not to let entropy win and if you didn't have these problems, it would mean you have no customers.

THE PROBLEMS YOU CREATE ON PURPOSE (ACTIVE PROBLEMS)

Your brain is the same as every other founder on a mission, always thinking 10 steps ahead, always dreaming, always exploring. Your feature roadmap in your head looks ludicrous compared to where you are now. Small side quests that may or may not have shiny object syndrome attached. The mind racing at a million miles an hour.

However, when these ideas trickle down to your team, they look like problems you created on purpose, just to create mayhem, lack of clarity, lack of leadership. They are second-order problems that only exist because you decided to make them a priority, you are willing them into existence:

It normally starts as execution chaos:

• The all hands on a demo for a prospect and everything has to change
• The feature release that is now timed based on an email you want to send
• Selling a feature that isn't quite there
• Changing your position mid-flight because you have a new learning
• You change "everything" from one conversation

Which in turn creates your org chaos:

• You change priorities weekly as you learn
• You kill work-in-progress before completion
• The "forget what I said yesterday, we're doing this now"
• You reorganize how the team works because you are not feeling it

Which maybe end up as:

• Ops & support breaks because you pushed growth
• Tech debt increases because you shipped faster
• The org strains because of load, direction, or your aggressive reqs
• Conflict appears because people don't agree or don't like the change

This is the cascade. Your idea → Execution chaos → Org chaos → Operational strain.

These problems are uncomfortable for literally everyone except you, and end up as impatience with literally everyone around you. But they also mean you're actually doing something that matters because progress and friction are joined at the hip.

The only question is whether your team understands that this is a massive competitive advantage or if this "annoys" them because they just need to "stabilize the ship" or some bullshit phrase or framework that means slowing down.

WHY THIS FEELS UNSAFE

So many founders relent to the team, stand down way too early, moving the focus to this stabilization. Company hygiene sounds lovely and it sure would make everyone happy.

Sure. Yes. But you're confusing implementing some basic groundwork to have a functioning company with enabling problems. They're not mutually exclusive. Also reactive problems are safer.

You're literally reacting to a thing that already happened. Customer complained. Bug shipped. Deal stalled. No one is saying not to focus on those... yes... immediately.

But. Active problems come with you being a leader, putting your name on the dotted line, making a bet, and running into it because you believe strongly in your position. That's the uncomfortable part. And if your employees are not early stage masochists, it can be really hard to be in alignment.

Early employees are not required to be masochists, maybe you haven't provided the incentive to them or it's a new experience or they just want stability. Which means they will struggle with alignment and the constant velocity will be uncomfortable. Which is why creating problems is hard, your team won't always understand, to them it looks like chaos... hence... calling them problems!

THE UNLOCK....

The ability to create problems well is actually a sign of a ship with good hygiene, great culture, and a brilliant team. Because if you have no baseline, if everything is always scattered, firefighting, reactive then of course it's impossible to introduce intentional chaos. Not because the grenade is any less painful when you lob a new idea at your CTO.

But because when you have good company culture, good org hygiene, everyone moderately aligned, there's a structured way for the people around you to embrace it / you.

They understand this velocity, this willingness to make big bets, this fight to get the customer, it's a weapon. It drives the ESOP. It drives investor excitement. It drives customer excitement. It drives org momentum.

Good hygiene doesn't prevent bold moves. It enables them, so the question isn't should we stabilize OR push hard. It's stabilize ENOUGH that you can push hard without breaking everything and everyone.

MEANINGFUL RISK VS NON-MEANINGFUL EXPLORATION

Not all problem creation is good, I am not advocating for your manic chaos as a weapon, you have to learn what needs to stay an inside voice vs distributed to the team because there's a big difference between non-meaningful exploration and meaningful risk - not everyone needs to know everything.

The book would say: random features, unfocused experiments, lack of thesis ARE BAD. Just noise. Exhaust everyone and don't teach you anything. Shows lack of focus, inability to lead, you MUST be intentional and deliberate.

Maybe. Kinda.

The way you must innovate is with clear bets, clear timelines, clear tradeoffs (we are NOT going to do THIS in order to do THAT) - surely this is the framework to produce the signal a founder needs. In failure you learn. In learning you get closer to the truth.

Both are correct.

Non-meaningful exploration based purely on noise is not a strategy, and there is too much noise everywhere for you to be in the pure consumption business. But sometimes small unfocused side quests unlock something. And you only find the something by doing the unfocused side quest because you felt a signal or saw a thing.

The key is to make sure non-meaningful exploration is not your business model and your random acts of problems are not actually random.

Perhaps it's better put as BOLD vs RECKLESS? All founders love calling mistakes some version of we took a bold move, but, a bold move generally does have a hypothesis, a time box, and a learning objective even if it's fuzzy.

So maybe. The question one could ask before embarking on creating a problem is:

What truth will this expose? If this works or fails, what will we know that we don't know today?

If you can't answer it, perhaps that's not a problem worth causing, could just be chaos.

THE 10X FORCING FUNCTION

As I said at the start, this isn't about being chaotic for fun. It's about the 10x forcing function. Every quarter, you have to ship a 10x feature. An "oh fuck" moment that makes your customer feel seen whether they explicitly asked for it or not. Something that even if you have a competitor following your footsteps, they cannot leapfrog your big ideas.

I do believe that founders just have to ship more stuff, better. More than incremental improvements or polish but a 10x leapfrog. And those leapfrogs, those 10x features don't come from reading the book or grooming your backlog, or user research in a silo. They only come from a signal you see that others don't. They come from thinking. Trying. Experimenting. They come from WHAT IF.

They come from the problems you create on purpose. Problems that turn into incredible insights, that deliver insane value for your customers.

So. If you are not responsible for a meaningful portion of your company's problems, you are not pushing hard enough and you certainly won't see the 10x signals.

Just to re-organize the thoughts.

If your week is spent reacting, explaining, smoothing, managing. Those are passive problems from things that occurred in the past.

All important, but you're protecting the present at the expense of tomorrow.

Cause better problems. Increase your likelihood of running into an epic idea. Build enough org hygiene that your company can handle them. Your job isn't to prevent problems. It's to trade up for better ones.

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

LFG.

- James