The Slow Grind That Sets You Free

7 min read Original article ↗

Naveen Gupta

In 2007, Ben Chestnut got the call every founder dreams about.

VCs wanted in. Mailchimp was growing. The money was there for the taking.

He said no.

His co-founder Dan Kurzius backed him up. They’d been running this email tool as a side project since 2001 — bootstrapped, profitable, boring. Why change now?

That decision cost them nothing.

And made them $12 billion.

The Lie We’ve Been Sold

Silicon Valley has a PR problem. And we bought the campaign.

Somewhere along the way, we started believing that “raising money” is success. That a TechCrunch headline about your Series A means you’ve made it. That the goal is to get funded, not to get free.

But here’s the uncomfortable truth: 75% of venture-backed startups fail. Despite the millions. Despite the advisors. Despite the fancy office with the ping-pong table nobody uses.

Meanwhile, 80% of startups are initially bootstrapped. They don’t make headlines. They make rent.

And occasionally? They make history.

The Mailchimp Math

Let’s break down what Ben and Dan actually did.

For six years, Mailchimp wasn’t even their main focus. They ran a web design agency. The email tool was a side hustle — something they’d built to help clients. No grand vision. No disruption narrative. Just a useful product that paid its own bills.

Then in 2009, they made a bet. They switched to a freemium model.

Within a year, their user base exploded from 85,000 to 450,000.

Slow grind. Then momentum.

By 2014, the platform was sending 10 billion emails per month. By 2019, they were closing in on $700 million in annual revenue — still with zero outside funding.

No board meetings. No pressure to exit before they were ready. No VCs asking why they hadn’t 10x’d yet.

When Intuit came knocking in 2021, Ben and Dan didn’t have to negotiate around a cap table full of investors. The $12 billion deal was theirs. All of it.

Because they never gave slices away.

Why Slow Actually Means Fast

I know what you’re thinking. But I don’t have 20 years.

Neither did Jason Fried.

He started Basecamp (then called 37signals) in 1999 with just $3,000. Today, the company generates over $100 million annually. Fifty-two employees. No investors. No exit pressure.

Fried has been vocal about why he never took VC money. In his words, a lack of funding helped Basecamp focus on profitability instead of getting distracted by “fun projects.” Constraints became curriculum.

But here’s what’s interesting about “slow” growth:

Research from ChartMogul found that when markets get volatile, bootstrapped companies adapt faster than their VC-backed counterparts. They’re used to doing more with less. They don’t panic when the runway shrinks because they never had a runway — they had wings.

VC-backed startups saw a 300 percentage point decline during recent market turbulence. Bootstrapped companies? Only 180 points.

Slow isn’t just philosophically superior.

It’s strategically smarter.

The Freedom You Can’t Buy Back

Let’s get real about what founders trade when they take outside money.

They trade equity. By Series A, founders retain a median of just 36.1% ownership. By Series B, that drops to 23%. By Series D? A measly 10.3%.

Take Pandora. Co-founder Tim Westergren held only 2.39% of his own company before its IPO. He’d faced over 300 VC rejections before finally securing funding — but the cost was his stake in the thing he’d built.

They trade control. By Series B, external investors own 61.6% of the company. The founder is no longer the decision-maker. They’re the decision-executor.

They trade their health. 83% of founders report diminishing returns from putting in more hours, yet VC pressure pushes them to work more anyway. And get this — 90% of founders don’t even talk to their investors about stress levels. The burnout is baked into the business model.

Now compare that to Basecamp.

Jason Fried famously advocates for 40-hour workweeks. The company doesn’t track vacation days. They’ve been profitable for over two decades while their competitors burned through cash trying to “win” a market.

That’s not just a business philosophy.

That’s a life.

The High-Profile Job Trap

“But what about just taking a high-paying job at a top company?”

I hear this a lot. And I get it. FAANG salaries are seductive. $300K, $400K, $500K packages with stock options and free snacks.

But let’s do different math.

That $400K job comes with golden handcuffs. Your stock vests over four years. Your identity becomes “Senior Staff Engineer at [Big Tech Company].” Your calendar belongs to someone else. Your creativity gets filtered through twelve layers of approval.

And here’s the kicker: you’re still building someone else’s dream.

The bootstrapped founder making $150K from a small SaaS might look “less successful” on paper. But they wake up without an alarm. They take August off. They can’t get fired.

Which one sounds richer to you?

The Grind Is the Gift

I won’t romanticize this.

Bootstrapping is hard.

There are months where founders check their bank accounts three times a day. There are moments when the doubts are louder than the dreams. There are years — years — where nothing seems to move.

Mailchimp existed for eight years before it took off. Basecamp spent its first five years as a web design agency that happened to build software.

But here’s what the slow grind teaches:

When you can’t throw money at problems, you learn to think. When you can’t hire ten people, you learn to prioritize. When you can’t afford to fail fast, you learn to fail smart.

Every skill that makes a great founder — product sense, financial discipline, customer obsession — gets forged in the fire of not having a safety net.

You can’t buy that education. You can only earn it.

The Question Nobody Asks

Here’s what I wish more founders would ask themselves before taking that term sheet:

What do you actually want your days to look like?

Not your exit. Not your valuation. Not your LinkedIn bio.

Your days.

Because here’s the thing about that VC check: it doesn’t buy better days. It usually buys worse ones. More meetings. More pressure. More people with opinions about how you should run the thing you created.

The bootstrapped path is slower.

Undeniably.

But slow is just another word for sustainable. For intentional. For yours.

The goal isn’t to build a billion-dollar company. The goal is to build a life you don’t need to escape from.

So Where Does That Leave You?

Maybe you’re sitting on an idea right now. Maybe a VC just slid into your DMs. Maybe you’re tired of the corporate ladder and wondering if there’s another way.

There is.

It’s not sexy. It won’t make headlines. Your friends in tech might not understand why you’re “playing small.”

But every morning, you’ll wake up and the company will still be yours. Every decision will still be yours. Every dollar of profit will still be yours.

That’s not playing small.

That’s playing infinite.

The $12 billion companies get the documentaries. But the $5 million company that lets a founder coach their kid’s soccer team every Tuesday? That’s the story we should be telling.

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