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StartUp Founders: Current-You.

Published September 19, 2026

Core Takeaway

Current-you is the least experienced, least networked, least skilled version of you that will ever run this company, which is the permission slip to punt hard problems to a more capable future version. That only works if a cleverer you actually exists, and it is not automatic. Experience alone does not produce expertise, deliberate practice does, and founders are the only elite performers with no practice pitch at all.

TLDR

  • Current-you is the worst founder you will ever be. Every version from here is an upgrade.
  • Which is the greatest permission slip going: you can punt. Why hand your hardest strategic problem to the least capable version of yourself who will ever exist?
  • It only works if there IS a cleverer you. That part is not automatic and most founders assume it is.
  • Every other discipline splits the job into training and performing. Founders get no practice pitch. Every call is live. Every single day is game day.
  • Ericsson's actual finding, not the Gladwell 10,000 hours version: experience alone does not produce expertise.
  • More experienced and more skilled are two different measurements and most people operate as if they are the same.
  • There is no socially acceptable slot for a founder who is learning. A pianist gets to be a student. You are expected to arrive finished.
  • Deliberate practice has three parts. Prepare, execute, review. Founders only ever do the middle one. Fix: name one thing before a call you are already taking, review it after.

Newsletter

Hey Reader,

Current-you is the least experienced, least networked, least skilled version of you that will ever run this company.

Not an insult, just some math, that on the assumption you didn't just doom scroll all day, then tomorrow you will have had one more day of reps, met one more person, made one more mistake, one more pitch, one more product call - all of it - so the version of you reading this is the worst one there will ever be, and every version from here is an upgrade.

This unlocks the GREATEST permission slip for founders... YOU CAN PUNT as in, why would you hand your hardest strategic problem to the least capable version of yourself who will ever exist!!!

Many of you are trying to solve down the line problems, how this plays out, how this all scales, and this is a nice reminder that sometimes we don't need TODAYS decisions to scale, we just need today to be great and lets PUNT it to a future version of you who is better equipped to solve it.

aka defer the cleverer stuff for a cleverer you as measured by The You Metric.

Obviously only works if there IS a cleverer you. Which is the entire point of this week's newsletter.... What are you actually doing to make sure there is a cleverer you.

Because it isn't automatic, you have to do a thing, a rep, of some kind, but so many founders think that by default, with time, you will get better…

GAME DAY

The concert pianist didn't start as a concert pianist, they started with one finger on one key. The grandmaster started by learning how a knight moves. The extraordinary lawyer started by opening a textbook and thinking what the f am I doing here.

Everyone starts at one finger. BUT BUT BUT…. this does not apply to founders, because in almost every single scenario of mastery, you get a practice pitch - you can learn by yourself, you can Kobe on the court for hours, you can study positions and scenarios and outcomes already known, so by the time the master plays, they have put in "the work".

More explicitly, almost all other professions are able to split their job into two - training and then performing - and every story about every elite anything always has their story of how they just did more training….

You don't get that. Every single thing you do, is live, in game, being scored - every sales call, every hire, every pricing decision - everything you do, is real, with the actual person in the room and there is rarely a take two.

Every single f&cking day, is game day, which means the only model for "more reps" or "better development" is to do it live more…

EXPERIENCE IS NOT EXPERTISE

Anders Ericsson wrote the book on this, how people get world-class at things.

This is not the 10,000 hours story, that's Gladwell and most find that story to be wrong, the real finding is narrower and considerably more uncomfortable... experience alone does not produce expertise.

What produces expertise is deliberate practice on the specific edge of what you can't do, on a weakness you know to be true and a mechanism for fast feedback, repeatedly.

Just to restate, what produces expertise is NOT doing the job, it is doing the hard part of the job, on purpose, as often as possible, as badly as you are, with as much feedback, until you are less awful.

Hence the people you know with twenty years of experience who are not meaningfully better than those with five - sometimes slightly worse.

How can twenty years of showing up not make you better. Rolls back to the opening. Yes, tomorrow-you has more experience than today-you. But more experienced and more skilled are two different measurements, and most people operate as if they are the same. Scar tissue of 20 years in the field, more experience, not necessarily more skilled.

NOW WHAT?

This all sucks for so many founders because the idea around training makes no sense and feels counterintuitive to the performance of being a founder. Admitting you need to learn sales means admitting you can't sell, and if you can't sell, what exactly are you doing here. So most founders just push on, fighting, until hopefully you get to a point you can bring in someone with the skill and the experience.

Someone who says they are training to be a concert pianist is applauded, there is a name for it, a student, but for a founder, there is this awful expectation that you arrive on day one "finished and ready" >>> an expectation which is not true and while founder bravado is important, at some point, every founder has the moment when they actually say… i know nothing about this yet and go on a fishing and research expedition.

STOP F&CKING WINGING IT

You know exactly what you're bad at. Bad at sales, so you send emails instead of picking up the phone. Bad at hiring, so you hire on gut. Bad at reading "data", so you don't prioritize telemetry. Bad at hard conversations, so you have none of them. Almost all scenarios you are the Founder, CEO and Arsonist. Or even worse, think you are great and are blaming everyone else….

And the plan for fixing any of it is… continue.

All of this to say, there is a free video by someone genuinely excellent at the exact thing you're worst at, a free online course, a book, a coach, a consultant, but mainly a freeeeeee video on youtube. There's literally a human who is epic at what you are shit at and you haven't reached out.

There is no lack of available information, there is a lack of you willing to do the work… and often times wrap it in a fun name - founder led sales….

We can run these comps all day. Football teams watch tapes on the opposition, have you ever listened to yourself on zoom, did you know you say "furthermore" 8000 times per call. Any deal or moment or thing that failed, did you go back to the tape and find the moment something changed.

Actual deliberate practice has three parts. Prepare, execute, review. Founders do the middle one. Only the middle one. Forever!!

SO, maybe we can make a tiny adjustment today, your day stays the same, you still have sales calls and everything else, just one change… pre-call be intentional on one thing you are going to try and focus being better on and post-call actually reviewing it….

FYI…

And this isn't the opposite of Conative Sabotage. Your conative style, how you're wired to take action, you build around that, you don't fight it. Skill is not a wiring. You can learn to be better at discovery calls.

I am delighted to know current-you. The worst founder you will ever be.

Feels like a good idea to make sure that stays true.

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

LFG.

— James

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About the Author

James Sinclair

James Sinclair

Founder Coach

3x Exited Founder and Founder Coach helping entrepreneurs navigate the startup journey.