Founder Evolution or Extinction: There’s No Middle Ground

"The difference between a vision and a hallucination is execution."
— Thomas Edison

Founder Evolution or Extinction: There's No Middle Ground

Dear Reader,

Startup founders either evolve faster than their startup or become its anchor. Maturity isn’t optional; it’s your startup’s life insurance. [Tweet]

Stakeholders expect milestones: customers seek value; employees need growth; investors demand returns; markets want innovation. Growth KPIs are universal. Your job is to deliver.

Book: Principles by Ray Dalio – the playbook for evolving endlessly and navigating complexity.

Last Week: StartUp Founders: The Misunderstood Lunatics?

Relentless self-belief got you here, your trust in yourself is at an all-time high. This is an asset and a trap. It introduces a blind spot, your way isn’t always THE way. Maturity and adaptive leadership means knowing when to listen, pivot or double down.

Founder maturity is akin to race car driving. You have to employ two mindsets: one for the immediate road ahead (Run the Business or RTB) and one for the bends and straights you can’t see (Invest in the Business or ITB). These mindsets are not separate, they are deeply interlinked. RTB is reflex, ITB is strategy.

The obsession with your first few customers in RTB mode is a rite of passage, showing those early customers who took a gamble that they made the right choice. You’re in the weeds, probably texting each other, they are shaping your product with immediate feedback, and that’s building traction and hopefully a loyal customer. But there’s a pivot point, one where if you don’t get off this path, you hit a ceiling you created unnecessarily.

You risk letting competitors leapfrog you, sales will naturally plateau and innovation is in the context of features; you are a feature factory, thinking one more “thing” will change everything – it never does. The maturity challenge is to transition from being reactive (RTB) to strategically scaling (ITB), showing customers they aren’t just vested in your product; they’re betting on your vision and your ability to execute. If you can’t switch to ITB, you become your startup’s biggest liability.

Maturity means ascending your own CEO ladder. The transition from a “founder” praying for your first customer to a wave of new “CEO” priorities, terms, expectations and a new set of problems. How you think about literally everything around you is changing. Each step signals a refinement in your leadership, business acumen and confirms you are the right leader.

ITB is your North Star. It’s not just about now; it’s about setting the wheels in motion for tomorrow. Of course, move fast, cut intelligent corners, but always keep an eye on the tomorrow. Every stakeholder bets on your vision, more than your day to day operations. Investors, customers and employees never stop gauging your potential, not just your today.

Maturity is mastering context-switching. It’s more than toggling between RTB and ITB. It’s bringing your full self to every meeting without a hitch, that ability to change topics on a dime and still be epic. Incredible founders context-switch seamlessly, with high functionality.

This whole speech feels like the startup paradox in all its f’n glory: you’re picking out your IPO symbol while still barely making payroll. It feels like having one eye on a microscope and the other on a telescope. How do you possibly reconcile this cognitive dissonance? Simply unsimple: 70% RTB keeps the lights on, 20% ITB sets the North Star, and the remaining 10%? That’s the space for adaptive leadership, the sand box that allows you to aim higher, the moon shots.

Every successful founder has done this walk. Going from the founder who met their angel investor in a hotel lobby to the CEO expected to master a VC boardroom. You have to feel it, right, you feel the metamorphosis happening? It’s a whole different ball game, and it requires a whole different athlete… that’s you!!

As you morph from player to player/coach, from frontline warrior to a tactical general. Part of that maturity curve is about letting go. Broadening your vision to include the insights of others. It’s time to delegate. You think you can’t afford a new exec, but you can’t afford not to. The right hire pays for themselves by driving progress that accelerates revenue, a profit center not a cost center. To mature means you need to cut the noise and zero in on what maximizes ROI. Welcome to maturity. Maturity is understanding value. True value. To the market. To yourself.

This journey is a combo of experience from just being in the game and a choice to undertake intentional learning. The battlefield teaches you resilience, but intentional learning keeps you adaptable. You’re always being judged, and without maturity, you’re a default ‘no’ in the eyes of the market.

Evolution is not optional; there’s no middle ground.

Go get a mentor. It’s likely time. It will change your life.

— James

(LinkedIn | Twitter | Tiktok)

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