Bill Rasmussen got fired by the Hartford Whalers, then chased an idea almost nobody believed in: sports television around the clock. He burned through his own money, his credit cards, his son Scott's money, and money from his father, sister, and brother. Six months before launch, out of cash, he signed a deal with Getty Oil for the tens of millions ESPN needed.

Episode page with video, links, and more

Getty took most of the company. Other terms were left as loose ends to settle after the contract, and employment contracts for Bill, Scott, and the early team were among them. They never got settled. Two early leaders were pushed out almost immediately. Scott was shown the door at launch. Bill was gone a year later.

Mike Soltys was hired as ESPN's first PR intern in 1980 and stayed 43 years, the last 20 as a vice president in corporate communications. He's now the network's official historian, and he tells this story on Bill's behalf, because Bill has never called it a mistake and doesn't look back.

The lesson holds up for any founder taking outside money: financial control and employment protection are two separate negotiations, and it's easy to lose the second one while focused on the first. Scott Rasmussen says he negotiated far better after watching what happened.

Mike also shares why ESPN's first live remote failed on opening night, why the network celebrates its bloopers instead of burying them, and how he used Bill's 1978-79 business diary to settle disputes when everyone remembered the same night differently.

In fighter jet aviation, errors can be fatal -- so the systems built around learning from them have to actually work. My guest is Christian "Boo" Boucousis, a former Royal Australian Air Force fighter pilot and CEO of Afterburner, a leadership firm that has spent three decades translating combat aviation discipline into frameworks for business leaders.

Episode page with links and more

Boo's favorite mistake is really a reframe of the whole concept: in fighter pilot culture, there's no word for "mistake," only outcomes to debrief. He tells the story of his first mission as a commander, which ended in a visible, ten-second failure in front of three of the most senior leaders in the Air Force -- and how every one of them owned their own error first in the debrief that followed. That moment became the foundation for ORCA (Objective, Result, Cause, Action), the method he now teaches business leaders to replace blame with structured learning.

We also get into the difference between "perfect" and "flawless," why an estimated 86 percent of leaders may carry undiagnosed perfectionism, and how that shows up as a need for control at work. If you lead a team and want a more honest way to talk about what went wrong, this conversation is for you.

Andrea Carpenter and Elizabeth Ledoux, co-founders of The Transition Strategists, were mid-negotiation on a business succession deal -- Andrea buying into Elizabeth's business -- when Andrea found out she was pregnant. The pregnancy wasn't the mistake. The mistake, as Andrea describes it, was her own rigidity: treating the closing of the deal as a fixed event that had to happen on schedule, instead of one point in an ongoing process.

In this episode, Andrea and Elizabeth unpack what changed when they let go of that mindset, and what it taught them about succession more broadly. They talk candidly about being opposite personality types -- Andrea a planner, Elizabeth an adapter -- and how that tension shapes their partnership. They also share the two mistakes they see most often when family businesses transition ownership: starting too late, and leaving the successor out of the design process.

Episode page with video, transcript, links, and more

If you're navigating a leadership transition, planning to bring in a successor, or thinking about what comes after you step back from something you built, this conversation offers a practical framework for treating that process as a journey worth designing carefully, rather than a deadline to hit.