Why success feels empty without purpose
Alex Bean sold Divvy for $2.5 billion in June 2021. By October of that same year, he was lying in bed telling his wife something he couldn't say to anyone else: "I'm jealous of my friends in the rat race." He knew how it sounded. He said it anyway, because it was true.
The feeling wasn't ingratitude. It was the absence of purpose. Every day at Divvy had been a grind with a reason behind it. After the sale, the grind was gone and so was the reason. His identity, his motivation, his daily dopamine hits, all of it had been tied to building something. When the building stopped, the emptiness moved in. This episode is the honest account of what that felt like and what he did about it.
The Divvy origin story and what actually drove the exit
Alex grew up in Seattle in a family of entrepreneurs stretching back to his great-grandfather. He was a geography major who, by his own admission, wasn't very good at college. The decade after graduation was spent jumping into other people's cars, working for people he respected, watching how they operated, and accumulating what he calls dangerous enough knowledge to eventually go out on his own.
In February 2016, his partner Blake came to his house with an idea: a credit card with software on it, essentially bringing the Venmo and Apple Pay experience to business spend management. They quit their jobs a few months later. They went to market in 2018. They sold in 2021. "It was a wild ride. We made a lot of mistakes. We had a lot of down days, but we had some awesome up days. And at the end, it ended well."
What the entrepreneur magazine articles left out: the Thursday email from US Bank shutting them down with no warning, the two weeks during COVID when their $100 million tranche from investors went unanswered while the bank could have pulled every customer's credit line at any moment. "My body didn't function," Alex says of that period. "I remember going into one of our meetings and my friend Blakeley, who was our CFO, just said, 'Do you need a hug?' And we literally started crying."
The Car Theory for hiring elite talent
Around 2019, with Divvy at roughly $1 million in ARR and a goal of reaching $100 million, Alex and Blake sat down and asked a simple question: which companies have already done what we want to do, in a way we respect? They wrote eight names on a whiteboard. Then they went to LinkedIn, not to recruit the head of revenue at those companies, but to find the number two, three, or four.
The logic is straightforward. The number one has already been paid and isn't hungry. The number two has been in the car. They know the road, they've seen the playbook work, but they weren't driving. Give them the keys and they'll run. "Some of our best hires came utilizing that theory," Alex says. He also applies it to career advice for young people: get in the car of someone great, do the work, go to lunch with them, and you'll find yourself in a position you couldn't have engineered any other way.
The Billboard Theory and finding real product-market fit
Before Alex left his well-paying job at Serge to start Divvy, he was cold-calling heads of finance at companies with 50 to 500 employees. These were friends of friends who were annoyed to be on the phone. That was the point. When he walked them through the mock-up of what Divvy would be, the responses were visceral: "When is it available? How do I get my hands on it? Wait, go back and tell me that again." That reaction was product-market fit.
He now calls the test the Billboard Theory. If you can't put your offer on a freeway billboard and have someone driving at 80 miles an hour know instantly whether they're your customer or not, you haven't found it yet. The Plum Tree Jewelry disaster from his college years, buying $1,000 of pearl necklaces to sell at an apartment complex community center, was the inverse lesson. Great margins, zero product-market fit, no business.
The unexpected downside of wealth and the curse of convenience
Alex is careful not to play the world's smallest violin. He knows his problems are not the worst problems in the world. But he's also committed to being transparent, because he's watched the same pattern destroy families and he thinks the silence around it does real damage.
When the money hit the bank account, he and his wife Megan weren't aligned. He wanted to move and change things. She didn't want anything to change, because she didn't want their four kids to become entitled. "She said to me, 'Alex, everyone in your life says yes to you. The only person in the world that says no is me.'" He sat with that and realized she was right.
He calls the broader pattern the curse of convenience. When everything is easy and everyone says yes, the friction of a spouse who holds the line starts to feel like opposition. That's where he's watched marriages end. The money didn't cause the problem. The ego that grew alongside the money did. Coming back to base camp, as he puts it, requires shaving a lot of that off.
Purpose, relationships, and the three pillars after the exit
Alex spent about a year after the sale doing what he calls hobby hill, piano lessons with his daughters, magic card tricks, golf. Things to stay busy. Not things to build toward. The turning point came when he could name what was actually missing: purpose, and the identity that came with it. A neighbor called him "the Divvy guy" and he felt the ground shift under him. That was who he had been. He wasn't that anymore.
His book organizes the lessons into three pillars. Purpose: without something to strive toward, the daily routine hollows out regardless of the balance sheet. Relationships: "The people that are rich have money. The people that are wealthy have relationships." And a third that runs underneath both, the willingness to ask honestly whether the number you're chasing will actually change anything about how you live, because in his experience, the difference between $20 million and $50 million changes nothing about the day-to-day. The mountaintop is real. So is the descent. Plan for both.
