Don’t start a startup

Whenever someone tells me they want to start a company, I say the same thing: “Don’t.” 

Our culture glorifies successful startup CEOs. But most of the bright-eyed people I talk to every week actually shouldn't become founders.

Becoming a founder is the hardest job you could possibly take on.

Starting a company is like wandering in the cold fog in the woods while you search for product market fit. It's eating glass as problem after problem pops up without no else to fix them except you. It's being disappointed by bad behavior from employees, investors, partners, and vendors over and over again.

And even if you make it through the early-stage gauntlet, it only gets harder from there. It's a mountain with no summit, just ever thinner air. 

I tell people there’s only two reasons you should start a company: 

1. It’s the only thing you can do. If staying in a “normal” job and working for others will ultimately get you fired or sidelined, being a founder is your calling.  

2. You have an idea that has kept you up at night for months, and that you can imagine waking up excited to work on for the next 10 years.

Both have been true for me. If my story sounds familiar, you might be a founder too.

Charting a course without a map

The truth is, I never had a grand plan to get where I am today. In fact, I never really knew what I wanted to do for much of my early career, and I made most decisions in the spur of the moment just by using my gut.

After a few years working in the Obama White House, at the nonprofit consulting firm Bridgespan, and managing network planning for Hawaiian Airlines, I arrived at Harvard Business School with a bunch of awesome professional experiences under my belt—but with still little idea of what I really wanted to do for the rest of my career.

I felt out of place amongst my peers who were clearer on their ambitions. Before I knew it, it was time to apply for summer internships. With little other bearings, I decided I wanted to work at one of three companies that seemed uniquely great at building distinctive internal cultures and brands customers loved: Starbucks, Nike, or Apple. 

I took an offer at Apple on the iOS product marketing team, but had very little previous experience with anything Apple-related—they even had to send me an iPhone because I had only used Android devices to that point.

"The only way to do great work is to love what you do"

The first day of my internship overlapped with the start of Apple’s WWDC Conference, where Tim Cook and other executives debuted the latest and greatest new features in the upcoming iOS release in their famous annual keynote presentation.

I walked up to the Moscone Center in San Francisco early that morning surprised to see thousands of excited engineers queuing in a line that snaked down several blocks. As soon as they dropped the ropes, an avalanche of people sprinted to get the best seats near the front. I was amazed by the palpable love all these people felt—for a company.

After the presentation, I ate lunch the park across the street, watching groups of enthralled attendees huddled around their computers to download the latest SDKs and beta apps, already racing to use the latest and greatest from the Apple team.

And that's when it clicked: "this is what I want to do," I thought. I wanted to create something that millions of customers would be excited to use, a product that would make their lives a little better each day, a brand that people would identify with to their core.

Since my time as a Duke undergrad studying systems change, I've always evaluated my life through the impact I make on others. But that first day at Apple was the first time I connected my "why" to a "how." And my realization that I was meant to be a founder has never changed since that day.

Being a founder is a repeat game

You might think, after this epiphany, it was all up and to the right from there, a smooth ride into the sunset. But that's not the end of the story.

It took me 5 more years to commit to being a founder full time. That included one failed attempt at starting something, 3 years of unhappily working for bigger companies, and a year of evaluating idea after idea until Almanac started to take shape.

Because I had considered so many concepts before it, the reaction to our first version of Almanac—Github for docs, an open source repo of validated templates and playbooks for tech—felt electric. People understood it quickly and wanted access immediately. We raised funding in just days, and the early momentum created the kind of energy I had hoped for years to capture.

But again, that spark was just the beginning. We found product market fit, pivoted to enterprise, found product market fit again, raised money, overscaled the team, laid off people, iterated endlessly on product and positioning to try and ignite sales, and then pivoted again to Blaze—before finally achieving venture-scale hypergrowth five years later.

My point in telling this story is that knowing you want to be a founder is not enough. Success requires finding an idea you care about enough to get out of bed each morning, even if the rest of the day will be deeply painful from there. Then it requires the grit and commitment to trudge through years of failure, battling against obscurity, until you're finally an "overnight success."

And regardless of whether Blaze continues on its trajectory to massive success or fails, I know it won't be the last company I run. In fact, I'll likely start something even bigger and more ambitious next. If I'm lucky, I will do this job for the next 40 or 50 years.

And because being a founder is a repeat game, my daily focus has always been on trying to get better. I treat each day as not just something to get through, but as a set of experiences to grow from. How do I master the subtle craft of starting and scaling companies? How do I reflect on and learn from my mistakes so I can move up the curve quickly? How do I identify and mitigate my own weaknesses as a leader and manager to become the best version of myself for our team and our customers?

But being a great founder is not just about mastering the hard and soft skills required for growth. Success also requires doing the right thing, as much as I can. In startupland, we work with the same small pool of investors, employees, and vendors across companies and years. So trying to be good to others—and apologizing when I fall short—is as important to my reputation and my internal sense of self as any business metric.

This job is the hardest thing I've ever done. But it's also the most satisfying thing I've ever done. I've experienced lows I never could have imagined. But through them, I've learned, I've grown, and I've triumphed—alongside a team of colleagues and friends I love, who built a product that makes a real impact in millions of people's lives.

My life as a founder is not easy, but it's been totally worth it. And it's still just beginning.

Next week - fundraising playbook!

Next week, I’ll write about how I’ve raised $50M from venture capital firms. Harsh truth: there’s a right and a wrong way to do it. If you want to get the most out of my fundraising playbook, share Startup Tycoon with just one friend and I’ll send you exclusive access to the deck I used to raise Almanac’s $9M seed round in 2019. More show, less tell, right?