When Brian from HubSpot kicked off the financial talk, he mentioned they were thinking of spending somewhere between twenty and thirty million dollars to acquire my company.

Let's just pause on that for a second. That is a staggering amount of cash. The startup world has a way of warping your sense of reality. You’re constantly hearing about nine-figure deals, billion-dollar valuations, and kids fresh out of college cashing out after a few years with enough money to land in the top 0.1% of the wealthiest people on the planet. These stories get all the media attention, making them feel like the norm. That famous line from The Social Network—"A million dollars isn’t cool. You know what’s cool? A billion dollars"—is supposed to be a joke, but in Silicon Valley, it’s practically a mission statement.

That’s completely insane. A million dollars is incredibly cool. A million dollars would have been absolutely life-altering for my family, for my wife Geraldine’s family, and for me at any point in the last decade. That’s true for over 80 percent of American families. Okay, rant over. I apologize.

Still, I’m almost embarrassed to tell you what happened next.

I got on the phone with everyone. I called Michelle Goldberg and Kelly Smith, our first and only investors. I called my mom. I called Sarah, my COO. The calls were short because I had a conference presentation to give, but I called them all again right after. We crunched the numbers, mapping out valuation scenarios and potential outcomes. We debated the value of HubSpot’s stock, which was private at the time but heading toward an IPO. We tried our best to weigh the risks and rewards.

Our logic, which seemed sound for a high-growth startup company at the time, went something like this:

• Software-as-a-Service (SaaS) companies like ours were being valued at 4 to 10 times their annual revenue.
• While the deal would be a great payday for the founders (my mom and I each owned 32.5%), it wasn’t a huge win for our investors, who would only see a three or four-time return on their $1.1 million.
• We were growing fast—about 100 percent year-over-year—with strong 80% net margins.
• We were considered a leader in the SEO software space and felt that our market position deserved a premium price.
• With revenue at $5.7 million in 2010 and on track for $10 million in 2011, Brian’s offer was in the 4-5x range. We thought we could push for a 6-8x multiplier.

Later that afternoon, I reconnected with Brian. I told him we were interested, but the price felt too low. I said that if he could get above $40 million, we could keep talking. Anything less just wasn't compelling enough.

The next morning, this email landed in my inbox:

Subject line: I don’t think we can really afford youHi Rand,You folks just might be too expensive for us . . . eyes bigger than our stomachs. We could probably afford $25 million for y’all. If that’s worth discussing, let’s continue the dialog. If not, perhaps we could have the conversation again down the road.It was great hanging out with you in DC.

My reply was brief:

Thanks Brian—I think we’re not in the ballpark, but really appreciate you thinking of us.Congrats on the raise and good luck with whomever you buy!

I’ve probably read that email thread a hundred times since then.

Twenty-five million dollars.

My 32.5% share of that would have been $8.125 million. Then, in 2014, HubSpot had one of the most successful IPOs in SaaS history, and their stock has soared since. That $25 million in stock would have become something much more. I try not to do the math, but it’s probably double that figure. Maybe more.

Every time I talk to my grandparents about selling their house to afford a retirement community that isn't their first choice, I think about that offer. Every time I visit Geraldine’s mom, who rents out rooms to make ends meet, I think about that offer. Every time we get asked why we’re still renting, I think about that offer. Every time we donate fifty dollars to a cause that deserves five hundred, I think about that offer. I think about it every time Moz struggles, every time we lay off staff, every time I've faced my own professional and personal battles.

Don’t get me wrong, Geraldine and I are not struggling. We’re in the top 20 percent of American earners. We can eat out, take nice vacations, and help our families when they need it. But $8 million is life-changing money. And given the strange math of startup equity, it’s probably more than we’ll ever make from Moz, even in a successful outcome.

The Strange Math of Founder Equity

Back in 2010, Moz had taken one round of startup funding. By 2016, we had taken two more. Thanks to that dilution, my ownership stake dropped from 32.5% to about 23%. That percentage will likely shrink even more over time.

Investors also have what’s called a “liquidity preference,” which means they get their money back first in a sale or IPO. For Moz, that’s $29.1 million off the top before anyone else sees a dime. Let’s imagine a fantastic $250 million exit for Moz. After accounting for dilution and investor payouts, it’s entirely possible my financial return wouldn't even touch what the 2011 HubSpot offer would be worth today. And a massive exit is far from guaranteed; a mediocre outcome is statistically just as likely. This is the reality of the leap from a side hustle to full time behemoth; the financial picture gets complicated.

I know it can be uncomfortable to talk about personal financial gain, but it’s a huge, often unspoken motivation for founding a startup company. We hide it behind noble phrases like “changing the world,” but let’s be honest: the hope of an extraordinary payday is part of the deal. Real transparency means talking about the uncomfortable stuff.

It wasn't just about me, either. In 2011, a Moz employee who’d been with us for a few years likely held between 0.5% and 3% of the company. A $25 million sale would have netted them between $125,000 and $750,000, not even counting what HubSpot’s stock did later. Now, a similar employee gets a more competitive salary but a much smaller stock grant with a higher price, meaning their upside is only a fraction of what it once was. It’s the classic startup trade-off: early stage means high risk for high reward, while later stage means less risk for a much smaller piece of the pie.

The Pressure to Win

Of course, money isn't the only thing at play. There's also ego, reputation, and pride. Startup culture draws a thick line between the "aspiring entrepreneur" and the "successful entrepreneur." Once your side hustle business takes on venture capital & funding, that line becomes even clearer. Your goal shifts from just building a great business to delivering a massive return for your investors. That becomes the sole definition of success.

This pressure creates a psychological obsession with "the exit." I’ve found myself jealously scrolling through tech news, seeing other companies sell for millions, and feeling that desperate desire to cross the finish line. It's a key part of the entrepreneurial psychology that drives founders. It's not just about the money; it’s about earning the title of "successful entrepreneur." That credibility extends to employees, too. Being part of an acquisition by a big name like Google or Facebook adds a certain glow to your resume.

For years, I told my team that if we succeeded, Moz would be an example of how our values could create extraordinary results. But if we failed, those values would fade into obscurity. This is the narrative at most venture-backed companies. You either become one of the 5% that delivers massive returns, or you don't. The culture often dismisses smaller, multi-million dollar sales as "selling out."

My advice to any founder or early employee is to reject that biased, investor-serving mindset. An effective startup management & strategy involves creating your own definition of success. A billion-dollar outcome shouldn't be pursued at the expense of a smaller, life-changing one. Be realistic about your odds and do what’s right for you and your team. Trust me, your investors will be just fine.