Serial founder Daniel Petkevich on selling Fair Square Medicare and his Tesla Roadster flying car prediction

Daniel Petkevich on Fair Square Medicare, Cars, and the Tesla Roadster

Daniel Petkevich built three companies across fintech and healthcare before landing on Fair Square Medicare, a platform that helped seniors navigate Medicare plan selection. The problem he identified was straightforward: Americans turning 65 face around 50 health insurance plans they can't meaningfully distinguish, with real consequences if they choose wrong. Fair Square helped 25,000 seniors find the right coverage before Petkevich sold the company after six years.

“My last company was Fair Square Medicare — sold it after six years. We ended up helping 25,000 American seniors find the right health insurance... Before that, did a fintech app called Trim, and way before that started a lender for the power sports space called Octane Lending.”

The earlier bets

Fair Square wasn't his first swing at consumer advocacy. Trim, his personal finance app, was among the first products to show users a list of recurring subscriptions pulled from their credit cards, and was one of Plaid's earliest significant customers. Truebill copied the subscription feature early on but ultimately out-executed, selling to Rocket for roughly $1 billion. Petkevich is direct about this: they got there first, Truebill got there bigger. Before Trim, he founded Octane Lending, a lender focused on the power sports market.

Tesla Roadster prediction

With Tesla's Roadster reveal set for October 1, and the FAA having cleared airspace to 10,000 feet, Petkevich's call is that the car won't leave the ground. His read is that the thrusters generate downforce rather than lift, enabling an extreme zero-to-60 time but no actual flight. He says the airspace closure is a PR move.

That said, he acknowledges the trade case: put down the $5,000 deposit, wait ten days, and watch the reveal. If the car is impressive, the reservation converts or flips at a premium. If it isn't, the deposit is refundable. The asymmetry is the point. He's less interested in owning a Roadster than in having the option.

Robo-dog side project

With time freed up post-exit, Petkevich has been building an open-source quadruped robot. His engineering critique of the form factor is that actuators, which generate radial motion, are a poor fit for the kind of linear torque that biological limbs produce naturally. He sees the mismatch as a fundamental constraint that most humanoid robot companies are working around rather than solving. For now, the quadruped is a party novelty — he brought it out for Rosh Hashanah and says guests went nuts for it.

His current show, Cars and Capitalists, features investors and operators riding in his old 911 around Marin. Guests have included Sam Lesson, Paul Goo, and Sam Damico. He runs it lean with a GoPro, no b-roll, no production crew.