In the thirteen years we’d been building Moz, we only ever got one serious acquisition offer. It all went down over 24 freezing cold hours in Washington, D.C.

It started with a friendship. Back in 2009, I’d become friends with Dharmesh Shah, the cofounder of HubSpot. We were in a similar space—marketing software—and we bonded over the shared struggles of building a company. We’d have late-night calls about everything from raising money from VCs to product strategy and what was happening with Google. When we were in the same city, our families would go out for these long, fancy vegetarian dinners. Building a business can be lonely, and having that connection was invaluable.

As our companies grew, it became clear there were opportunities to work together. Then, on a call in January 2011, Dharmesh mentioned that HubSpot was looking to make some acquisitions, and Moz might be on their list. This was a different level of conversation, moving beyond a simple partnership to something that could change everything about our path—and was a world away from the early days of simply starting a side business while employed.

He introduced me to his cofounder and CEO, Brian Halligan. We were both scheduled to speak at a conference in D.C., so we planned to grab coffee. I walked into a cavernous, deserted cafeteria, my coat still on because the heat could barely keep up with the cold outside. I wasn't sure what to expect. A casual chat? An exploratory talk?

Nope. Brian got right down to business. Within minutes, he laid it all out: HubSpot was making a formal cash and stock offer to buy Moz. He wanted me working on products with Dharmesh and to merge our teams. But before diving into the details, he needed to know if the financials would work.

At the time, Moz was doing well. We’d hit $5.7 million in revenue in 2010 and were on track for $10 million in 2011. Brian said HubSpot was thinking in the range of twenty to thirty million dollars.

What Silicon Valley Logic Does to Your Brain

Let's just pause for a second. Twenty-five million dollars is an incredible amount of money. The startup world warps your perception with constant news of billion-dollar deals, making you think anything less is a failure. But for my family, for most American families, a million dollars is life-changing. And here we were, talking about twenty-five times that. It was more than just a million dollar side hustle; it was the kind of money that secures futures.

So, I’m a little ashamed to tell you what happened next.

I immediately called my investors, my mom (who was also my cofounder), and my COO. We spent the day running scenarios. We looked at HubSpot’s private stock value and its future potential. We weighed the risks and benefits. Our logic was pure Silicon Valley textbook:

• Software-as-a-Service companies were being valued at 4-10x revenue.
• The offer was around a 4-5x multiplier on our current revenue. We felt our growth and market position deserved a premium, maybe 6-8x.
• For our investors, the return would only be 3-4x their money, which wasn't a huge win for them. That's a tough pill to swallow when you've taken on startup funding.

Late that afternoon, I spoke to Brian again. I told him we were excited, but the number felt too low. I said that if we were talking north of $40 million, we could keep the conversation going. Anything below that, we weren’t interested.

The next morning, an email came through with a subject line that said it all: "I don’t think we can really afford you." Brian said they could probably do $25 million. If that was worth discussing, we could continue. If not, maybe we could talk again down the road.

I replied quickly: "Thanks Brian—I think we’re not in the ballpark, but really appreciate you thinking of us."

And that was it.

The Lingering Cost of a "No"

I have probably looked at that email thread fifty times over the last six years. Twenty-five million dollars. My 32.5% stake would have been $8.125 million. And when HubSpot went public in 2014, their stock soared. That $25 million would have easily doubled, maybe more.

That decision haunts me. Every time I think about my grandparents stretching their budget for a retirement community, or my mother-in-law renting out rooms to make ends meet, I think about that offer. Every time we write a small check to a charity that deserves more, I think about that offer. When Moz has struggled, when we’ve had to make gut-wrenching decisions or lay people off, I think about that offer.

Don’t get me wrong, my wife and I are not poor. But $8 million is a completely different reality. It’s the kind of money that changes everything for you and the people you love. That decision was a hard lesson in the difference between paper wealth and real security, and it’s a story that’s rarely told in the triumphant tales of those chasing the jobs to become a millionaire.

The Hard Truth About Founder Equity

You might think that since Moz's revenue grew 7.5 times since that offer, my stake would be worth much more today. But that’s not how venture capital & funding works. Thanks to follow-on investment rounds, my ownership has been diluted. Today, my wife and I own about 23%, down from 32.5%. Our investors also have a liquidation preference, meaning they get their money back first in a sale.

Let’s imagine a successful $250 million exit for Moz in the future. After dilution and investor preferences, it's very possible my financial return wouldn't even reach what that 2011 offer from HubSpot would have. That's the peculiar reality of this game. You can build a much bigger company and still walk away with less.

It’s uncomfortable to talk about the money, but it’s a huge part of why people start companies. We hide this motivation behind talk of "changing the world," but the hope for an extraordinary payday is real. Being transparent about it feels necessary, because it’s one of the most misunderstood and uncomfortable parts of being an entrepreneur.