I am the guy that doesn’t move the goalposts—I can promise you that.

Like any founder, I have goals for Outseta—both personal goals and team goals. And I'll work more diligently, over an extended period of time, than almost anyone to meet them. But when I do, I’m on to a different game—I can promise you that.

I see so many tech founders make $20M, only to focus on making $100M. They’re rats on a treadmill, whether they realize it or not. They tell us it’s all in the name of loving to build technology start-ups.


Take away the financial rewards, and 90% would rather be doing something else. But it's what they're good at, so they can't get away from it. They get too much validation, too much of their self worth from their financial success— whether they realize that or not.

It’s not that I don’t love building Outseta— I thoroughly enjoy it. I fell in love with building start-ups long ago. I've already devoted the entirety of my career to it, and I intend to devote at least another decade to doing so. But devoting 25+ years of my life to anything is enough. Very few people actually benefit from devoting their whole life to anything in my opinion. That would certainly be a very one dimensional approach to me.

I think we’re sitting on a big opportunity at Outseta. What Shopify did for e-commerce, Outseta has the opportunity to do for SaaS and membership businesses. Especially as the number of non-technical founders grows, the opportunity is right in front of us. We don’t need to build a billion dollar company like Shopify, but I think we have the opportunity to make a major impact on a large number of founders. That motivates me every day.

But when the day comes that I reach my goalpost—for myself, for the impact we’ve had on the lives of our team members, and for the impact we’ve had on our customers—I’m out of here. On to something new.

I’ll write. I’ll travel. I’ll have that many more lazy days hanging out with my wife. I’ll try to leave the world better than I found it. I’ll open a restaurant on an island and cook the best damn meal I can for 12 guests sitting with their feet in the sand two days per week.

But it won’t be another tech start-up. It won’t be endless angel investing. I won’t be moving the goalposts in a pointless pursuit of more

It will be an entirely new chapter of me. Watch and see.