Recovering From Failure

"They gave me another shot to do a V2 of it and I got the impression it wasn't like my last shot, but I certainly was feeling a little dejected from going from a hot shot, new PM to a new thing. So, we spent a lot of time thinking about how can you make something that's just much more compelling and not just a digital version of the Yellow Pages and not just so similar to some of the other products out there."

"And the product was fine, it worked, but it really wasn't differentiated. And in many ways, I think, again, I think I've had these reflections more sense than at the time, that I had some of the time, but why use this instead of Yahoo Yellow Pages? But more than anything else, why use this instead of the Yellow Pages? It was a digital version of something that had come before."

"Usually a successful pivot gets warmer instead of colder from what you're an expert at and somehow builds on what you learned on the prior idea. Right? And so in the case of Brex, it was they had worked on a FinTech company in Brazil when they were younger, and so I'm like, 'You need to work more on the thing all about and not the thing nothing about.'"

"I said, we need to become a wartime company. If we don't fight for this, we are dead. I jumped hard on AI, but I also restarted the culture. I rewrote the values designed to be a sharp knife to cut out the parts of the company that I just knew wouldn't be effective."

"People act like having a startup fail is the worst thing that can happen to you. And man, that's not even in the top 10. It's bad, I've done it, it's awful. It's really bad, but far worse is to be in a company that won't die, a zombie, undead company that you hate, but you can't leave."

"And then we realize because it's so new, it's just so unstable. It don't know where the bug come from. It's from your source code or from the underlying libraries? Then we have to restart the company, rebuild the whole thing."

"I basically say, 'How much conviction do you have in the solution you're building?' I know in the beginning, before you knew all you know now, you had tons of conviction. Now knowing all you know, do you have more or less conviction in the problem and the solution you're building?"

"You've got the persona, the problem, the promise, and the product. Lattice kept the first one but changed the others. Vanta changed all four."

"We started that as a B2C and then we realized that this is way harder than we think it is, and we ended up with converting that into B2B, which turns out to be very successful for us. And so occasionally there are companies that you start your journey with one perception and you change that and that will happen multiple times."

"Obviously that's a very big moment because that was a bet the company moment in the sense that we basically said, told our investors, 'Hey, we're making money on this.' We had already raised 28 million of capital and we were just like, 'Hey, we're just going to pivot entirely from this.' And we did that overnight."