A few months ago I sat down with Bart Houlihan—co-founder of B Lab and former president of AND1—during a live interview at a Hampton team retreat in Philly.
Bart had told a story or two that were founder folklore by now, but hearing him tell them live—with no pretense or notes—just hit differently.
“We should’ve failed,” he said. “Multiple times. But our customers bailed us out. Our partners bailed us out. Our employees bailed us out.” (note: if you haven’t heard or read any of the And1 stories – especially about Stephon Marbury literally breaking his ankle in his And1 debut, check out the Netflix doc).
It reminded me of another guy I got to know a lil’ bit—different style, same sort of grit.
John Mackey, the co-founder of Whole Foods, tells a story from 1981.
Less than a year after opening their first store in Austin, Texas, a 100-year flood tore through town and destroyed their inventory and equipment. No flood insurance. $400K in damages. It should’ve been the end.
But the community showed up: employees, customers, suppliers, even a local banker.
They helped get the store reopened within a month.
I first heard that story firsthand at a board meeting.
Mackey sat on the board of The Motley Fool—the company where I spent 12+ years—and I was lucky enough to spend a lot of time with him across quarterly meetings.
He stood out. Not just because he was smart or mission-driven (he was), but because he was real.
Candid. Quirky. Still processing the Whole Foods-Amazon acquisition in real time, weeks after it hit the headlines.
That kind of openess always stuck with me.
Anyway—these stories hammer home something I’ve experienced again and again: resilience isn’t just about your grit.
It’s about who’s around you when things go sideways.
Solo Acts Burn Out, but Teams Bounce Back.
Every great thing I’ve been or done was built by a team.
At The Motley Fool, it was Jeremy, Bleeker, Austin, and Brendan. We made a ton of content. Scaled marketing to crazy heights, took big swings. Laughed a lot.
At The Blueprint, it was Doug, Kevin, Adam, and Patricia—one of those rare crews where we made a beautiful product, everyone could lead, no one needed credit.
At The Hustle, it was Brad, Steph, Ethan, Ben, and Katy. That was a squad that could move fast and talk shit and have fun.
You have your people.
The ones who stay late, can push themselves and one another, and then can keep building even when the plan breaks.
It’s easy to forget that when you’re the one in charge. But the longer I do this, the clearer it gets: it’s never quite a solo act at all.
There are Three Types of People Who Will Save You
When building your team, consider these traits:
- Ride-or-Dies: Individuals who are deeply committed to your mission. They’ll go the extra mile, not because they have to, but because they want to. Doug’s worked with me at two different companies—The Blueprint and Hampton. He gets how I work, what I’m trying to build, and how to push things forward without a lot of crap. We move fast, stay aligned, and don’t need hand-holding. It just works. That kind of belief in the mission—and in how you operate—is rare. When you find someone like that, you build with them for as long as they’ll let you.
- Feelers: Team members who understand and share the feelings of others. They’ll offer support during tough times and help maintain morale. After a super tough financial situation at one company, I was exhausted. Almost depleted by it all. And it was my exec assistant who kept checking in on me… telling me I was right to feel the way I did. That she understood.
- Resilients: Those who can just problem-solve, stay with it, and keep composed under pressure. When I took over at The Hustle, churn was increasing because credit card failures were too high. It was one of those ‘oh shit, this is a fire drill’ sort of moment. And for two weeks straight, I was on the phone until midnight with Steph and a commerce consultant, trying to patch up the bucket. Just doing the work. No drama. No complaining. Just staying late and figuring it out.
Screw the Resume. Hire for Grit.
It’s easy to get wowed by credentials or people that have worked at the fancy tech companies.
But when I hire, I look for:
- Failure stories: If they’ve never screwed up, they’ve never been tested. Or they aren’t comfortable being honest, or they’re trying too hard to sound perfect. Either way, eff that noise and move on.
- Alignment: Don’t just look for “culture fit”, whatever that means to you — but do they get excited by what you’re building? Because if they’re aren’t excited, there’s no way they’re going to go the extra mile.
- EQ over IQ: Can they lead people? Read the room? Handle tension without drama? Know when to push and when to back off? My personal opinion – and this I’m sure is controversial – is that you can find smart people everywhere. IQ is easier to screen for. EQ is much more rare.
I hired someone not long ago who – on paper – was perfect.
Had all the right experience. Did the exact work we needed them to do. Got several backchannel references.
But as soon as they joined, they got insecure—surrounded by high-performers, they started questioning their own worth.
And insecurity bred paranoia, and that resulted in more time freaking out than bringing actual value.
It was a bad cycle, and I couldn’t help them out of it.
They had skills – but not the EQ to last on the team, and it was a disaster.
Summing it Up
Eventually, every founder gets punched in the mouth.
And in those moments, it’s not a pitch deck or a vision board that’ll save you.
It’s people. The ones who stay calm when things go sideways, who roll up their sleeves when the room freezes.
So, build a team like your life will depend on it.
Because you will fail.
And when that happens, you’ll be glad you built the net first.
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