Let me be unabashedly nerdy for a second: I love SEO.

I love the blend of technical craft and creative strategy it takes to outrank a competitor for a tough keyword. I get a genuine thrill from seeing a small tweak to a webpage drive thousands of new visitors. There’s a certain magic in decoding the mystery of search engine algorithms, and when I stumble upon a new tactic or prove a hypothesis about Google’s ranking process, I feel an incredible sense of discovery. It’s the kind of deep work I can lose myself in for hours.

So, as the CEO of an SEO software company, you’d think I’d be in heaven, right? I was living the dream.

Except, I wasn't.

The CEO Job Is Not the Job You Loved

Early on, when my company was more of a consulting gig, my days were filled with the hands-on SEO work I was passionate about. But as we grew and I stepped into the CEO role, that percentage plummeted. My time spent doing the work I loved dropped from a majority to less than 20%, and some months, it was barely 5%. This is the reality of starting a side hustle while working full time that nobody prepares you for: when it succeeds, the job you signed up for disappears.

The learning curve was brutal. I wasn't just learning how to be a CEO; I had to apply those lessons immediately with high stakes. Employees depended on me to steer the ship. Customers counted on our tools being better than the alternatives. Investors expected rapid growth and financial discipline. A whole community of marketers looked to me for insights.

I remember one week where I was recruiting a CTO, scrambling to close a fundraising round, preparing conference presentations, renegotiating salaries, designing product wireframes, and promoting a book. In all of that, I did almost zero hands-on SEO.

The myth that you can start a company to "do what you love" is deeply flawed. The truth is, that passion might get an early-stage company off the ground, but once you find a working business model and start to grow, your responsibilities change completely. When your side hustle to full time business starts hiring, organizational complexity becomes the mortal enemy of deep, passion-focused work.

Your Passion Must Evolve

Unless you absolutely love managing people, navigating crises, delegating, setting strategy, and repeating the company vision until you’re blue in the face, the CEO role probably isn't the work you dream of. A startup doesn’t let you do the work you love; it gives you the chance to bring a vision you love to life.

You have to reset your passion. It can no longer be, "I want to do this specific work." It has to become, "I want to see the thing I'm building change the world in this specific way." If you can’t make that mental shift, the frustration of being pulled away from your craft can kill your motivation. It's a crucial step in the journey from a side hustle to small business.

And that journey is messy. Great companies are built by wading through a painful slog of failure, learning, and repetition. You realize you have a problem, try a dozen ways to fix it, fail at most of them, find something that partially works, then deal with the new problems your solution created. At my company, Moz, it took us six years and two CEOs just to land on a project planning process that didn't make everyone miserable. In the end, our CEO, Sarah Bird, had the insight to restructure the company to avoid the problem altogether. That’s the real work: digging into problems and untangling the knots that hold people back.

A Startup Carries Its Founder’s Baggage

It’s no secret that a company takes on the personality of its founder. Amazon reflects Jeff Bezos’s passion for logistics and his famous thriftiness. In the same way, Moz has always been a marketing-centric company, because that’s my background. Getting millions of people to our website was the easy part. Building high-quality software? That’s where we always struggled.

Why? Because my co-founder and I had no formal programming experience. We fell into the software world through our marketing work. Almost every founder believes they can just hire people to cover their weaknesses, but it’s rarely that simple. A founder’s attributes get baked into the company’s DNA. Your strengths become the organization’s strengths, and your weaknesses become its chronic problems.

Lacking deep knowledge in a critical area means you’re less likely to identify the right hires, less able to manage them effectively, and less equipped to even know what you don’t know. For years, our software products stagnated while competitors caught up. We hired multiple CTOs and dozens of engineers, but we couldn’t recapture the magic we had with our first engineering team. It wasn’t until Sarah—who also lacked a technical background—invested immense energy to learn the engineering side of the business herself that we turned that fundamental weakness into a strength. She proved you don't have to be an expert, but you have to invest enough to effectively lead experts.

The Hard Truth About Raising Money

When you’re trying to scale, especially with a model like ours, the pressure to seek venture capital & funding is immense. But this is another area where the popular narrative is dangerously misleading. You might think that once an investor puts money into your company, your incentives are aligned. In reality, their success model and yours are often wildly different.

Venture capitalists need outlier returns. Out of ten investments, they expect five to fail, three to break even, and only one or two to deliver the massive gains that make the whole fund profitable. This means a "good" outcome for you—like selling the company for $40 million and making everyone millionaires—is a useless return for them. They need you to swing for the fences, to chase a billion-dollar valuation, even if it means taking risks that could kill the business nine times out of ten. If you aren't prepared for that high-stakes game, taking their money is a mistake. This reality check is vital for anyone dreaming of a million dollar side hustle powered by outside investment.

Even if you do build a successful company, it doesn’t mean you’ll get rich quickly. The idea that you can compress a forty-year career into four years is a myth. For the first thirteen years of Moz, a company that was by most metrics a success, my salary was often below the Seattle tech average. My wife drove a 2003 Kia, and I didn't own a car. Owning a large amount of private stock in your own company sounds great, but it’s illiquid. You can’t use it to pay your rent.

Founding a startup or joining an early-stage company is a gamble. You sacrifice the certainty of a higher-paying job for the hope that your equity will one day be worth something. Don't do it just for the money. Do it for the freedom, the accelerated learning, and the chance to build something you believe in. Let the potential financial payout be the icing on the cake, not the cake itself.