The Final Chapter of My First Startup

I’ve told this story only once before. 

Never in writing. Never on video.

My voice was shaky and I barely stumbled through it. 

But with a few years of distance I think I’m finally ready. 

Here goes…

For 17 years I had one job. A job that defined my adult life, my self-worth, the majority of my friendships, and entirety of my personal finances. On February 27, 2018, I left. Or, depending on who’s telling the story, got pushed out.

It wasn’t just scary, it was heart-wrenching. My insides felt torn up. I couldn’t sleep. I wasn’t eating.

The company I’d founded and led as CEO didn’t want me around. How would I pay our mortgage? Cover healthcare and housing for my grandparents? Who would I be if I wasn’t the “Wizard of Moz” anymore?


That’s how much we had in savings when I left. 

Not terrible, by any means. Not great, if you divided it by 17 years and factored in Seattle’s cost of living. Definitely not enough to retire or fully fund a new venture. Our $5,000/month mortgage on a 110-year-old house that needed constant repairs was feeling mighty stressful. 

Getting another job felt like defeat. I needed to prove to my old board of directors, my ex-CEO (and now ex-best friend), and all the people in my professional world that I could still do this. That my first company wasn’t my only company. It wasn’t a fluke. That they’d bet on the wrong horse. Revenge isn’t the healthiest of motivating emotions, but it damn sure is an effective one.

My last day was one of the worst of my career. Topped only by the layoffs my company had done 18 months prior.

I wrote a whole chapter about how I should have taken Hubspot’s 2011 offer to buy Moz, and never felt that pain more intensely than just before my departure from the company

The next day, February 28, was one of the best.

Not because I had some personal epiphany or found joy in the freedom of starting again, but because of what happened after I published this blog post: My Last Day at Moz. My First Day at SparkToro.

I woke up to literally thousands of messages – in the comments, on LinkedIn and Twitter, Instagram and Facebook, in my new inbox. 


It took me almost two weeks to reply to all of them; almost all were overwhelmingly positive. 

People whose careers I’d helped, or who’d appreciated my work at Moz reached out with generosity, kindness, compliments, and stories … Stories about their own lives and work, and how something I’d done had helped them get a job, or do their job better, move careers, get a client, get a promotion, get customers.

Taken together, the sum of these messages led me to the inevitable conclusion that, although those 17 years at my first startup might have failed to live up to my expectations, my investors’ financial requirements, even my team’s hopes, for tens of thousands of folks in the marketing world, we’d made a real impact. I couldn’t feel sorry for myself in light of an accomplishment like that. That day reframed how I viewed those 17 years forever.

With SparkToro, I resolved to completely overhaul how I designed a business, its goals, and its operation. In Casey Henry, I found the perfect compliment to my skills and vision for the company’s future (granted, he’s a tad bit grumpier than I’d want, but that’s part of his charm). Venture Capital was antithetically aligned to those goals (and I’d so thoroughly slagged off the entire VC asset class in Lost & Founder, my just-published book, that I doubt any of those investors would have replied to my emails). So, we built our own funding model. And we designed a new, Chill Work approach to our professional lives. We created a set of company values that fit with who we wanted to be (BELUX).

SparkToro took almost 2 years to launch as a product, but it’s done quite well since then. We’ve stayed profitable, grown, brought on Amanda, and managed to repay our investors, too.

Rand & Amanda give Casey a hug during a docuseries filming in January 2023

But this isn’t a story about SparkToro, it’s a story about the end of Moz. At least, the end of Moz for me.

While I’d left the company as an employee in 2018, Geraldine and I remained large shareholders (with ~20% of the company’s common stock). I continued to, technically, be the chairman of Moz’s board of directors, albeit a powerless one. The rest of the board, including the CEO, disagreed with me on almost every major decision. When I tried to convince the board that we should sell (in late 2017) and connected them with a potential buyer who’d reached out to me personally with a rough, 2X revenue offer, one board member replied and said they “wouldn’t even entertain a conversation about selling for that price.”

Until 2 years later…

In 2019, the company hired bankers to try and sell the company. After a long, frustrating process, they settled for a suboptimal price (below the 2017 offer!) and signed a term sheet from a private equity buyer. The deal wasn’t great: $90M for a software company doing $52M in revenue is a lackluster multiple. But, growth had stalled the last 4 years, and the market for small-cap SaaS just wasn’t there.

Still, Geraldine and I were set to make over $14 million dollars from that transaction. I don’t know how to describe my feelings other than… it didn’t feel real. The day before the acquirer’s diligence ended we were in Italy, visiting friends, and I splurged on a fancy hotel (I think it was ~$400/night).
That evening, in the not-quite-as-fancy-as-advertised hotel room, I got an email from Moz’s CEO. The buyer was pulling out. The transaction had fallen through.

I didn’t sleep a wink. (Geraldine let out a single barking laugh and went immediately to sleep, like a supervillain.)

$14 million dollars. Poof. It was never real. Moz would probably never be worth anything, at least to our bank account. 

I was angry and sad… and angry at myself for being angry or sad. 

I didn’t need that money! We were in Italy with friends, taking a cooking class. Life was wonderful. Casey and I were already building something better. Something that wouldn’t compromise the principles I believed in. Something I believed could make just as big an impact in the marketing world without the heart-wrenching rollercoaster of a VC-style startup.

In 2020, I left Moz’s board of directors, appointed Asia Orangio to my board seat, and Tara Reed to the long-empty independent seat. I was done. Geraldine and I had long talks about how those 17 years wouldn’t come to anything financial, but the good they’d done for others and the skills they’d helped me (and Casey) build would find value in our new venture. SparkToro kept growing, kept being profitable, kept being a wonderful experience. F*** the $14 million. I had a life and a job and a partner I loved.

I never understood or figured out what happened between myself and our CEO. For more than a decade, we’d been best friends. She’d been the officiant at my and Geraldine’s wedding. We went on vacations together. We babysat her son. When Geraldine had her brain surgery, Sarah waited with me outside the operating room.

A 2014 photo with Sarah, my best friend and longtime COO turned CEO, her family, and our friends Marshall and Tabatha Simmonds on a vacation to Cape Town, South Africa. It still breaks my heart to look back at these.

But, a couple years after she became CEO, our relationship fractured. We fought in almost every meeting, disagreed about the future, the past, what Moz should and shouldn’t do, and how. To me, she seemed like a completely different person than the one I’d loved for so long. I was sure our friendship would only deepen with time, and instead it fractured completely. I found this snippet at the bottom of an email sent to some friends in 2017:

“I’m sad as shit to leave. I love Moz the company. I love 80%+ of the team. I love the work and the mission. And I’ve spent my whole adult life there, built it from deep-in-debt mom-and-son consultancy to a startup I thought had a real shot at hitting a homerun.

To be fair to Sarah, I’m sure from her perspective, the story reads completely the other way and if she were writing this it would be something like: Rand left as CEO in a bad situation in 2014. I had to clean up the mess, and he didn’t support my decisions, and it made me look bad to the team, and cost us morale. Then he hurt his credibility and influence with the board, and (edited for privacy), which felt like kicking me while I was down, so I was forced to reciprocate. His presence is toxic, and even if he might be valuable, it’s not worth it to have him at the company after this year.”

Here comes the weird part.

In May of 2021, I got an email from one of my old board members and investors at Moz. They’d “decided to sell the company.” Sure, whatever you say, buddy. I didn’t make much of it. I was convinced that, much like the 2017 and 2019 deals, this too would pass.

OK – one more little story before I can tell you the big one.

In late 2015, a new sushi restaurant opened in Seattle: Sushi Kashiba. If you come to town, go, because it’s incredible. A few weeks after it opened, some entrepreneur friends invited Geraldine and I to join them for a happy hour there. We hadn’t heard of it, and didn’t look it up, we just went. When we sat down, we only knew about half the party we were joining, but it quickly became clear that everyone else at the table outearned us … by a lot.

Surrounded by millionaires, we opened our menu to find… a $220 per person Omakase (tasting menu) that the whole table had to do together?!

Geraldine immediately tried to find a way out of it. 

“I’m really not that hungry,” she said.

“We’ll finish whatever you don’t!” someone offered. 

“Can we afford this?” she whispered to me.

I whispered back, “technically, it’s our whole eating out budget for the month, but don’t worry. You see that guy over there?” I nodded in the direction of one of our tablemates. “This week, his company sold for $1.2B, and he owned a lot of it. You don’t become a newly-minted almost-billionaire and not pick up the tab.”

The meal was fantastic. The company was a smidge fancy-pants, but fun. The check arrived. Recently minted hundred-millionaire grabbed the bill. And then he said…

“Shall we split this seven ways?”

We paid $550 with tip. (Thank god I didn’t get the sake flight.) Geraldine was incensed.

“New rule,” she said as we left, “if we ever get a big payday, even 1/100th of what that guy made, we cover EVERY TAB IN THE JOINT, got it?” She swirled her finger in the air, the way you do when you’re buying a round.

“Hell yeah.”

Back to 2021. June. We’re on our first trip since Covid, vaccinated and masking, visiting Geraldine’s family in California for the first time in 18 months. We’re out to breakfast at a divey, open-all-hours spot near San Diego’s boat repair and marine industrial complex. A large contingent of dock workers have just ended their night shifts and are impressively inebriated for 9am at the bar. We sit down. I order coffee from “Nana,” the only member of wait staff on duty. I look at my phone, seeking a less rowdy spot to start our morning, and see an email from our bank.

SUBJECT: You have received a deposit larger than $100

Too nervous to open it, I hand the phone to Geraldine so she can. A second later, she shakes her head, smiles, and swirls her finger in the air.

The sum is much less than the $14M I thought we might get in 2019. But it’s still a life-changing amount of money. A lottery-winning amount. We tell Nana that we’ve had a spot of good luck, and we’d like to pick up every tab in the restaurant.

Geraldine in June, 2021, about to buy a whole lot of breakfast beers.

“I feel like Oprah!” she says, processing check after check on our card.

One gentleman arrives at the paystation from the bar and Nana tells him we’ve covered his bill. He looks at us like we’re the FBI and he’s D.B. Cooper.  “Nah, nah… for real?” he asks. And when Nana replies, “Yes, honey! For real,” he drops her a $5 tip and runs out the door like a man being chased.

We laugh, incredulous, and drive to meet Geraldine’s nieces at the mall. 

We tell them, and their parents, that college is officially covered.

We help Geraldine’s brother buy a house.

We invest in a few friends’ startups (sadly, they’ve folded–startups are hard).

We start college funds for a friend-who’s-passed-away’s kids.

We pay off the leaky, 111-year-old house. (Given where mortgage rates went, a poor decision in retrospect).

Geraldine writing a card to an ex-Mozzer, July 2021

We write just north of $700,000 in personal checks to Moz employees and ex-employees whose stock options didn’t pay out fairly (all under the gift tax limit, in case any IRS folks are reading). I hesitate to share this bit because it sounds like I’m trying to make us out to be these saints of capitalism, which we are definitely not (Geraldine would like me to note that she is, “a full-on capitalist goblin who buys all the vintage Springsteen t-shirts on eBay”). We certainly could have given more. I share this only in the hopes of nudging (shaming?) other founders and investors who get big paydays into doing the right #$%ing thing for their own teams, no matter what the cap table says.

Geraldine walked into my shed/office while I was reviewing documents to be signed for the Moz transaction and snagged this photo

We find an investment professional in Portland to manage our savings. He tells us to keep working and living within our current budget until we’re in our sixties, and if the market maintains its usual trends, we should be able to retire comfortably. Neither of us are sure we ever want to retire, but both of us grew up poor enough that we take this advice to heart.

I’m not sure what the private equity company that bought Moz is doing with the business. I know very few people who still work there, and since signing some documents in 2021, have had no news about the performance or future of my old startup. I’m angry that the business did so poorly in those last few years, that they (in my opinion) screwed over so many employees who were key to the company’s success, that the far-superior 2017 offer was never considered and that the 2019 transaction fell through, that the board chose never to listen to me after I stepped down as CEO.

But also, I’m so happy with my new career, with this little company Amanda and Casey and I are building, with the life we have and the future that’s possible. Most of my resentment has turned into gratitude for the lessons I learned, the skills I acquired, the wonderful people I got to meet and become friends with, and the incredible kindness the Moz community showed me after my departure. The financial windfall is more than anyone needs, and it’s a wonderful gift we’ve been able to share.

I have regrets. So many of them. But they come from this unlikely journey. Is regratitude a word? That’s how I feel.

So, why share this story? Why now?
Three reasons. 

First, my non-compete and some of the other legal clauses I’d signed to close Moz’s sale are no longer in force. I’m still not allowed to reveal the sale amount, which is the only reason I haven’t. 

Second, not enough people talk about the complicated ends of startups, and when they do, they usually aren’t transparent, because it doesn’t make them look good or serve their future interests. I hate that survivorship bias, and I want more public stories that tell the truth, warts and all.

And third, stories stick with us even when data doesn’t. You can hear that 95% of VC-backed founders fail to earn even a 1X return. Or that 1% of founders build unicorn-valuation companies. But those stats rarely stick. What sticks in our memories and informs our future beliefs is almost always based in stories. It’s how human beings are wired. And I want people to know that even with that lottery-sized transaction, I’ve made less than many of my “got a good job at Google/Microsoft/Amazon/Meta” friends. Building a $50M/year startup does not guarantee wealth. It was just as likely (as we saw in 2019) that the company could have been sold for parts or folded, or simply not cleared the liquidation preference (investor terms are tricky and always rigged in their favor).

This story was, initially, going to be one I told at SparkTogether, our story-focused event for marketers on Nov. 16. But, Amanda and I realized that it’s not really a marketing story, and that unlike the speakers at the event (which we don’t record to enable authentic, transparent storytelling that wouldn’t be otherwise possible), I wanted this one recorded and preserved.

“So this whole post was just to sell me a SparkTogether ticket?!”

No. This story is here because I wanted to tell it. I’ve been wanting to tell it for years. SparkTogether gave the excuse I needed; the kick-in-the-pants to finally write it down, get it off my chest, and publish the final chapter I’d always felt was missing from any discussion about “what happened with Moz/Rand?”

But, if you made it this far, and want more of the power that stories have to illuminate the dark corners of the business world, we’d love to have you join us for SparkTogether (tickets are here).