Let’s be honest — most founders are control freaks.

We call it “protecting our vision” or “keeping standards high,” but what we really mean is we don’t trust anyone else to do it right.

And I get it. I’m one of them.

When I started building Rare Founders, I did everything myself — events, partnerships, sponsorships, content, emails, videos. Not because I loved doing all that, but because I thought no one else will do it the way I want.

For a while, that worked. The community grew, events blew up, and people started calling it the most popular founder event in London. But now I’m hitting the same wall Noam Wasserman wrote about in Harvard Business Review back in 2008 — The Founder’s Dilemma.

He nailed it: founders want to be both rich and king — but it’s almost impossible to be both.

Wasserman studied hundreds of startups and found that every founder eventually faces a brutal choice:

Founders who go for “rich” give up equity, hire strong execs, and share decision-making.

Founders who go for “king” keep control but often hit a ceiling.

Most of us convince ourselves we can do both.

We can’t.

Rare Founders is growing fast — new partnerships, bigger events, and now a whole data side to the business. But growth means complexity. Suddenly you need systems, teams, and trust.

If you’re still running everything yourself, the business isn’t scaling — you are.

You’re scaling your workload, stress, and burnout.

For the last two years, I’ve been the “king.” Every decision went through me because I wanted things done right.

But I’m realising I’m the bottleneck. If I don’t let go, I’ll end up killing what I built.

Founders fail not because of product or market — but emotion.

We’re attached to our startups like parents to a child. We sacrifice everything, then panic when someone else touches “our baby.”

But that attachment keeps us small.

Wasserman calls it the founder’s paradox — the better you do, the faster you outgrow your own role.

You start as the visionary who makes everything happen. But once the company needs structure, process, and delegation, that same energy becomes resistance.

You don’t want to hand over the CEO role.

You don’t want to let go.

You don’t want to admit someone else might do it better.

But that’s exactly what your business needs.

By the third year, half of founders aren’t CEOs anymore.

By IPO, fewer than one in four are still in charge.

Not because they failed — because they succeeded.

Success brings investors, boards, and specialists. The founder who built the company becomes the one holding it back.

The irony? The harder you work to make it big, the faster you make yourself replaceable.

I see this all the time in our community.

A founder gets traction but refuses to delegate. Rewrites every post, double-checks every pixel, questions every hire.

They say they’re “protecting quality.”

They’re actually protecting ego.

And it’s not arrogance — it’s fear.

When your business becomes your identity, letting go feels like losing yourself.

I’ve felt that too. Every time I delegate and it’s not perfect, my brain goes: “See? That’s why I should’ve done it myself.”

But that mindset doesn’t scale. It just burns you out and blocks your team.

Rare Founders started as a one-man show. No budget, no marketing, just hustle.

That worked early on. But the bigger the vision gets, the clearer it becomes: being “the one who does it all” turns from strength to liability.

The same instincts that got you here might stop you from going further.

You’re both the reason your company exists — and the reason it can’t grow beyond you.

If you’re wondering whether you’ve become that founder, ask yourself:

If most answers are “no,” congratulations — you’re the bottleneck.

Control feels safe, but it’s an illusion. The tighter you hold on, the slower everything moves.

Sooner or later, you’ll either let go voluntarily, or the business — or investors — will take control for you.

I’ve been thinking a lot about that rich-or-king framework.

At first, every founder says, “I’ll have both.” You picture scaling globally while still calling every shot. But reality doesn’t care what you picture.

You either choose growth and share control — or keep control and accept limits.

Right now, I’m standing at that junction.

Rare Founders can stay small and fully controlled — or grow into something much bigger, data-driven, global.

To get there, I need to delegate more, trust more, and stop micromanaging.

It scares me. Because, yes, I like control.

But if I don’t start letting go, I’ll choke the very thing I’ve built.

So maybe it’s time to stop pretending I can be both rich and king — and decide which game I’m playing.

If you’re a founder reading this, you’ll face this choice too.

You can:

Neither path is wrong.

But pretending you can have both? That’s how startups die.

Wasserman found that founders who were honest about their priorities — money or control — made better long-term decisions. Those who weren’t clear ended up with neither.

If you want wealth and impact — hire smarter people and get out of their way.

If you want autonomy — accept slower, steadier growth.

The mistake is saying you want one while acting like the other.

I’m still learning to step back without feeling like everything will fall apart.

Letting go doesn’t mean giving up — it means trusting others to carry the mission forward.

Maybe that’s what real leadership looks like: not being the one doing everything, but building a team that can do it better.

So if you’re still doing it all — pitching, selling, designing, managing, invoicing — here’s the truth: you’re not a superhero.

You’re a bottleneck with a cape.

And the sooner you accept that, the faster your company (and sanity) will grow.

Wasserman’s research might be 15 years old, but it’s still spot-on. The startup world worships founders who do it all — the lone geniuses, the all-nighters, the “hustle till you die” heroes.

But the real challenge isn’t starting — it’s evolving.

At some point, every founder hits the same fork in the road:

Do I want control, or do I want growth?

For me, I’m learning to choose growth — even if it means stepping back.

Because I’d rather build something that lasts, even if I’m not the one holding the crown.

And if you’re reading this and nodding quietly — maybe you’re at that same point too.

It’s hard as hell to let go. But maybe the next level of success isn’t about doing more — it’s about finally trusting that you’ve built something strong enough to survive without you.

✅ If this hit home, pass it on — there’s probably a founder in your circle still trying to do it all themselves. And drop a comment if you’ve been there — the more we talk about it, the faster we normalise letting go.

(👉 Vote now — we’ll share the results in next week’s issue. All votes are anonymous.)

(Last week’s poll results)

👉 Have you ever been approached by a “fake investor” or something that felt off during fundraising?

💼 Pylyp Samoilenko

Background: Strategy & finance professional with founder and operator experience. Helped scale a healthtech startup from €2M → €5M revenue, secured €2M+ in VC funding, and led M&A due diligence with one of Europe’s largest healthtech firms.

Focus Areas: Product, growth, and strategy.

Currently Seeking: Role in VC or a startup/scaleup at the intersection of product, growth & strategy.

Contact: LinkedIn | [email protected]

🚀 Gaimcontrol

What they do: Building financial services for vulnerable customers — starting with people recovering from gambling addiction. Their first product, Toivo, is live, while the fintech side remains in stealth.

Founder: Jean-Paul Efang Mbome

Looking for: Founding members with early-stage tech or fintech experience to join ahead of the next growth stage.

Contact: LinkedIn | [email protected]

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