When Fast in and Fast out Money F*cks It All: The Bootstrap debate
“I thought scaling was success. Now I just want to feel like me again.”
We often celebrate growth, scale, and the hustle. Yet, seldom do we discuss what gets trampled in this relentless pursuit:
The founder’s passion.
The team's cohesion.
The very essence of the business.
This is a reflection for those who’ve been told that more is always better, yet feel a dissonance deep within. For the ones who feel the success story doesn’t match the pressure and the sleepless 3:48 a.m. wakeups.
As Rory Sutherland would say, the logical mind gets all the airtime, but the emotional, alchemical, irrational parts of decision-making are what actually move the needle. Scaling sounds rational. It’s defendable in a boardroom. But maybe, just maybe, the magic isn’t in doing what everyone else is doing. Maybe the truly successful founder doesn’t chase scale, they design their own game.
And maybe the smart money isn’t fast money at all.
Warren Buffett puts it simply:
"Only buy something that you’d be perfectly happy to hold if the market shut down for ten years."
His investment ethos isn’t driven by noise or exit velocity. It’s built on patience, discipline, and long-term conviction. Buffett doesn’t just invest in businesses. He invests in enduring models, principled leadership, and 100-year visions.
Buffett's favourite holding period is, famously, "forever" a principle that reflects a deep commitment to long-term value creation over short-term speculation.
Which begs the question:
Why are we building companies like we’re flipping houses, when the real masters build like they’re planting trees?
🚨 The Hidden Cost of Fast In, Fast Out
Misaligned Motives
External investment brings money, but often misaligns the mission.
Founders build with love. Investors optimise for return. One is human. The other is transactional.
At first, it seems like rocket fuel. But it often turns into a fire you can’t control.
"We stopped building what we believed in. We started building what we thought they wanted."
And that’s when the compass starts to spin.
💣 I Was There: The Beenz.com Experience
Let me tell you a story I lived.
In 1999, I was part of the senior leadership team looking after EMEA & APAC RIM at Beenz.com, a pioneering startup (bleeding edge) creating a universal internet currency before anyone had heard of crypto.
We raised nearly $100 million from the likes of Larry Ellison and François Pinault. Offices in 15 countries, 250 + people. Global rollout. PR galore. The dream was alive.
And then came the pressure.
The pressure was massive, from the top to the bottom.
Decision-making became fogged. Emotions ran hot. Fear, urgency, and expectation filled every room.
Every roadmap led to one question:
"How do we get out of this, with an IPO?"
It was the only viable path to justify the investment. Until the dotcom crash. Until the story changed.
The IPO window slammed shut. Investors went quiet. We sold what was left to Carlson Marketing Group.
But the emotional cost?
That stayed.
The passion turned to exhaustion. Confidence to confusion. We didn’t just lose the company, we lost a piece of ourselves.
That experience shaped everything I do now with The Alchemists. Because I know what it’s like to build fast, and burn hard.
And to quote Sutherland, sometimes the irrational, unscalable thing, like slowing down or protecting soul over scale, is the smartest move of all.
📉 What Gets Lost
1. The Culture That Made It Work
Fast scaling erodes intimacy.
You hire too fast. Middle management bloats. Performance becomes theatre. Culture becomes collateral damage.
HBR and McKinsey both confirm: Culture is the first casualty post-funding.
2. The Founder’s Identity
You start to lead someone else’s company. One investor board meeting at a time.
You wake up wondering if you still believe in it. Or worse, if you still believe in yourself.
3. Decision-Making Clarity
You lose your centre of gravity.
Every decision now loops through a layer of financial expectation and strategic detachment. You stop trusting your gut.
4. Post-Exit Void
The day the cheque clears doesn’t feel like freedom. It feels like grief.
Bo Burlingham’s Small Giants. Tugboat Institute. Exit Planning Institute. They’ve all documented it. But most founders won’t say it aloud.
So I will:
You’re not broken. The model was.
🔬 Rich or King?
Noam Wasserman’s The Founder’s Dilemma nails it:
Choose to be Rich (take capital, lose control) or be King (retain control, build slowly).
Beenz chose Rich. So did many others. Most never got the payoff. Some got the cheque, but lost themselves.
Would I do it the same way again? No.
Would I trade the lesson? Also No.
It was one hell of a ride, OMG it was fast.
🪡 Neuroscience of Regret
When your values and your actions misalign, your brain knows.
It spikes cortisol. It sends threat signals. Decision-making collapses.
You’re not just burnt out. You’re biologically and psychologically misaligned.
And no amount of growth metrics or LinkedIn praise will fix it.
That’s why our work at The Alchemists isn’t just about business. It’s about reclaiming your clarity, your fire, your voice.
Because irrational or not, sometimes the most valuable thing you can do is stop scaling long enough to remember who you were when this still mattered.
♻️ What’s the Alternative?
You scale on your terms. With your people. In alignment with your purpose.
At The Alchemists, we help leaders:
STOP and take active time out to think and decide
Grow enduring businesses
Make clearer decisions
Lead without betraying their values
Reconnect with who they were before the pressure took over
You don’t have to play their game. There’s another way.
As Rory Sutherland reminds us: real magic happens when you stop optimising for logic and start listening to what feels right.
And here’s the part many overlook:
📊 The Power of Bootstrapping and Enduring Growth
Bootstrapping isn’t small thinking, it’s long thinking.
Bootstrap founders maintain control, build sustainably, and keep the soul intact. They make decisions based on customers and culture, not cap tables.
The research backs it:
According to The SaaS Bootstrapper's Survey, bootstrapped companies are 2.3x more likely to be profitable after 5 years.
Harvard Business Review notes that founder-led and bootstrapped businesses are more resilient during economic downturns.
Tugboat Institute's Evergreen businesses outperform peers on longevity, retention, and trust.
Bootstrapping forces clarity, constraint-driven creativity, and care.
It’s not about avoiding risk, it’s about owning your decisions and staying true to the business you wanted to build.
In a world drunk on unicorns, this is the unglamorous, high-integrity path that builds legacy.
As Buffett himself might say:
"Someone is sitting in the shade today because someone planted a tree a long time ago."
🔍 You’re Not Alone
📃 Beenz.com – $100M raised. IPO as only exit. Sold post-dotcom collapse. Emotional fallout never discussed.
📚 Small Giants – Those who chose culture over scale thrived longer.
🏛️ Tugboat Institute – Evergreen businesses win with soul, not speed.
🎓 Harvard – 65% of VC-backed founders are removed within 18 months of funding.
🚪 The Invitation
You don’t need more strategy.
You need a space. A room. A breath.
A place to say out loud:
“I don’t want to f*ck up what's next.”
That’s The Alchemists.
Not hype. Not hustle. Just truth, trust, and traction.
If this hit a nerve, maybe it’s time to step into an session with me.
No judgement. No pitch. Just tea. Or whisky. Or a Walk. And your next clear move.
Book your session, face to face or online or reply "Let’s talk."
This is your Skunkworks for the Soul.
Build wisely. Stay grounded. Grow greater.