Go Out on a Limb

What have been three career defining moments for you? And how have those shaped your approach to leadership?

I would say, probably the first was leaving Intuit and starting Pay Cycle. And I think the defining moment there was getting back to my roots of entrepreneurship, knowing what was in store, what was in front, the hard work. One of the conversations I’ve had with my mom— this is probably 10 years ago, so maybe a dozen years after I’d started, Pay Cycle. I’m driving home and like hey mom, and we’re talking, I was saying something about how hard it was whatever. And she said, “Yeah, if your dad and I’d ever known how hard every business was, I don’t think we ever would have started any of them.”

And I said, “Yep, but if you knew how great it was to make a difference in somebody’s life, you would have started them faster.” And she said, “Exactly.” And that’s the challenge of being an entrepreneur, because when you get started, you don’t have any of that taste of victory, so to speak, you don’t know the impact you’re going to have, all you have is the burden of slogging it out. And so I would say, starting a company and taking that risk, and finding out that it was okay. I have a magnet on the fridge downstairs that says, “Go out on the limb, it’s where the fruit is.” And I think we always forget that, you don’t get that fruit – and if you think about being in nature – you don’t get the ripe fruit unless you’re willing to go on the limb, sometimes the branch breaks, and that’s okay.

So, I think that was the first career-defining moment for me. I would say the next moment was that lesson in accountability that we talked about, it with the financial crisis in 2008. The way that we had that conversation with the company is, I did not give everybody the Sequoia deck. But I did go to the whiteboard – we had a massive whiteboard – and I drew all the charts that were up there. I talked about the economic situation, what was happening, what this meant. I talked about the data that was out there suggesting that capital was drying up. And I said, “And so we have a decision to make to keep the company alive, we’re out of cash, and we got to do something.”

So, everybody in the company got to hear my perspective before a decision was made. And then we broke up individually to talk to each individual in the company, about what the decision was and the impact for them. Everybody got a copy of the book, Who Moved My Cheese. As a way to just…

That’s a good book.

Yeah, it’s a good book, as a way to say, things change, and it’s time to embrace and see what happens next for you and for us and we’ve stayed in touch with many. And I think the learning there was, when you’re accountable, you are vulnerable and you’re human, and you lead the team with that. The team understood, the people that had to go that day, the 11 employees that left, we went from 26 down to 15. The 11 that left, it was a sad day, but it was a sad day for the other 15, but everybody understood and everybody respected the decision.