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.

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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.

Larry Kasanoff has produced more than 200 films, including Terminator 2, True Lies, and the Mortal Kombat franchise. So it's fitting that one of the most useful lessons of his career came from a kid on a set tour.

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Larry had decided to redesign the Mortal Kombat character Kano, dropping his metallic eye because it felt too close to the Terminator's exoskeleton. A junior-high student touring the set saw the new design and had a full-blown panic attack over the change. As Larry puts it, "My mistake hit me. My audience point-blank told me what to do." He had been designing for himself, not for the people who loved the character. He changed Kano back that day, and the character is still going strong decades later.

That tension between an artist's instinct and what the audience actually wants runs through the whole conversation. Larry and Mark get into the bet-your-job decision behind Platoon, why an idea everyone instantly loves should make you nervous, and the 3D network that folded in six months because it chased technology with no real idea underneath it -- and what all of that says about the rush to make decisions by algorithm.

A candid, funny, and useful conversation about creativity, risk, and the discipline of knowing when to trust your gut and when to listen.

Publishing strategist Wiebke Tasch had built a bestselling book and a comfortable full-time income on Amazon -- enough to quit her PR job. Then one morning an automated email told her she had violated Amazon's terms, and both of her accounts and all of her books were deleted. No warning, no explanation, no human to appeal to. Her mistake: she had opened two accounts, one for a pen name and one under her real name, not knowing Amazon allows only one per person.

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That is Wiebke's favorite mistake, and losing everything turned out to be the start of her company, Digital Authors. In this episode, she shares how she rebuilt and what the experience taught her about never building a livelihood on a platform you do not control.

We also get practical about publishing as a system: why book structure should start with market demand rather than your own wish list, why the first five days after launch shape an Amazon book's entire future, and how to spot the predatory "buy reviews" emails that prey on anxious authors. Wiebke is candid about AI, too -- a useful tool for proofreading and getting unstuck, but a fast track to forgettable, same-sounding books when it replaces your own voice.

If you are an expert thinking about writing a book, or you just want a sharp reminder to own your audience instead of renting it, this one is worth your time.

To save a few thousand dollars in legal fees, six-time Silicon Valley CEO Mike Grossman decided to act as his own lawyer on a routine distribution contract. Years later, when Dun & Bradstreet moved to acquire his company, he reread that contract and realized a single ambiguous sentence could be read to block any sale without his competitor's permission. His board told him not to worry. His mentor, Bill Campbell -- the "trillion-dollar coach" -- told him the board was wrong and that he had to fix it fast.

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That story is Mike's favorite mistake, and it opens a candid conversation about what running a startup actually feels like when the cameras are off. Mike is the author of the new book Failure Is an Option: Reflections of a Silicon Valley CEO, and he doesn't filter out the hard parts.

We get into why the most common layoff mistake is cutting too little rather than too much, how staged cuts become a "death by a thousand cuts" that erodes a leader's credibility, and why luck and timing often matter more than the Silicon Valley meritocracy myth admits. Mike also makes a practical case for radical transparency -- about finances, lost deals, and failures -- as the way leaders earn the trust they'll need when things get hard.

If you lead a team and want an honest look at decision-making, psychological safety, and learning from mistakes, this one's for you.

Kate Lowry was fresh out of college and working at McKinsey when she saw a colleague do something she believed was seriously wrong -- something that could constitute blackmail, with another employee's ability to stay in the country hanging in the balance. Her instinct was immediate and absolute: this is wrong, and I'm going to tell everyone. She reported it and criticized the person sharply in reviews.

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It backfired. She got marked down for not being a "team player" and carried that mark on her record for the rest of her time at the firm.

The lesson Kate draws isn't that she should have stayed silent. It's that good intentions and zeal are not the same as effective action. The best ways to help people, she found, are often more sophisticated -- and when you're up against sophisticated actors who hold power over you, you need to bring equal sophistication.

Kate is a CEO coach, venture capitalist, and author of Unbreakable: How to Thrive Under Fear-Based Leaders. In this episode, she and host Mark Graban get into the difference between high standards and fear-based leadership, why psychological safety is about mutual trust rather than comfort, and how the quiet, "West Coast nice" version of fear-based leadership is harder to spot than the cartoonish yelling kind. Kate also explains her concept of reading a leader's "emotional age" to predict their behavior, and offers practical tactics for anyone stuck under a leader who rules through fear.

Eric Ries had a 40-page business plan. An Excel model so complicated it would crash Excel. A team of elite students, real investors, and a working product. What he didn't have was a strategy -- and he didn't realize it until after the startup collapsed.

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The moment of clarity came in a Boston job interview. A panel of consultants asked what he'd learned. He gave them practical tips. They told him that wasn't strategy. Sitting there, he realized he didn't actually know what the word meant. That category error -- mistaking a polished plan for a strategy -- is the mistake that eventually became The Lean Startup.

In this episode, Eric traces the line from that dorm-room failure to his new book, Incorruptible: Why Good Companies Go Bad and How Great Companies Stay Great. He argues that many of the so-called best practices founders are trained to follow aren't pillars of capitalism at all -- they're modern inventions with a poor track record. We get into the Whole Foods unraveling and why John Mackey couldn't simply cut prices, the prehistory of Costco through Sol Price's fiduciary duty to the customer, and what Jim Sinegal built into Costco's governance that has held for four CEOs and forty years. We also look at Novo Nordisk's industrial foundation structure -- a hundred-year-old design that makes companies six times more likely to survive fifty years -- and why most founders have never heard of it.

A conversation about strategy, structure, and the quiet ways good companies go bad.

Joe Hennes runs Tough Pigs, the premier Muppet fan site, and for years he also worked at Sesame Workshop -- the dream company he had been writing about since 2006. In this conversation, Joe is unusually candid about what it actually costs to merge fandom and profession.

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He explains why he kept his Sesame job quiet, what changed when he saw "how the sausage is made," and how being laid off from the place he had always wanted to be reshaped his relationship with the work. He also walks through how Tough Pigs broke the Steve Whitmire/Kermit performer story in 2017, why he resists the rah-rah instinct most fan sites default to, and why he thinks the new 50th anniversary Muppet Show special worked when so many recent reinventions did not.

Along the way, Joe and Mark get into the marketing miscalculations behind Muppets Most Wanted, the case for more Muppet specials instead of full seasons, and the genuine joy you can see on a celebrity's face when they get to share a chair with Kermit. For leaders, it's a thoughtful look at the cost of fusing identity with employer -- and what it takes to keep enough distance from the things you love to think clearly about them.

Deborah Coviello has spent her career walking into businesses with quality crises and operational pressure, and walking out with stronger leaders behind her. In this conversation with Mark Graban, she shares the favorite mistake that taught her one of her most lasting lessons.

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At a global leadership meeting, Deb presented her plan to turn around the worst-performing region in her company by leading differently rather than firefighting harder. Her peers loved it. Her boss told her she had spent too much time on her leadership style and not enough on tactics. She left the room deflated. Eighteen months later, her region had moved from fourth out of four to second - by focusing on her people's confidence, capability, and capacity instead of working them harder.

The deeper mistake, she tells Mark, wasn't the presentation itself. It was skipping the change management step of running her new thinking past her boss first - and later, staying in a role longer than she should have because the title felt like security. The conversation also covers her lift-light-lead framework, why "you shouldn't have said that" is the wrong response to an employee speaking up, and the argument behind her new book: peace of mind is a leadership outcome worth more than the next quarter's results.

Jesse Jackson, contact center leader and host of Set Lusting Bruce, joins Mark Graban to share his favorite mistake: going gun-shy as a new leader when veterans push back with "we tried that, it didn't work." Jesse explains why that deference cost him his best ideas, and how a Harry Chapin story about "two kinds of tired" reshaped the way he leads.

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We get into the real cost of staying quiet when you're new, the difference between listening to your team and being silenced by them, and the Aaron Sorkin line about surrounding yourself with smart people who disagree with you. Jesse also shares a cautionary tale about volunteering for a role he wasn't ready for, and what he changed about how he chooses opportunities now.

The conversation moves into what psychological safety actually looks like day to day - treating new ideas as honest experiments rather than ego defense, and making sure team members feel heard even when their advice isn't taken. We close with a stretch of podcasting craft (forgetting to hit record, scheduling buffers, the value of embracing tangents) plus tangents of our own on Bruce Springsteen, the misunderstood patriotism of "Born in the U.S.A.," and Spinal Tap.

If you've ever walked into a new role with ideas and quietly let them die in the face of "that won't work here," this episode will give you a sharper way to think about when to push and when to listen.

Dr. Melisa Buie is an operational excellence leader and co-author of Faceplant: FREE Yourself from Failure's Funk. She has a PhD in nuclear engineering from the University of Michigan, taught graduate engineering courses at San Jose State University, and has worked at semiconductor and photonics companies including Lam Research, Coherent, and Applied Materials. She is also the author of Problem Solving for New Engineers.

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Melisa's favorite mistake is one she didn't recognize until ten years after the fact. After publishing her first book while juggling a full-time job, teaching, and raising her son as a single parent, she was exhausted -- so she did nothing to market or promote it. She told herself she had earned the rest. What she actually did, she now sees, was choose invisibility. The lesson wasn't that rest is bad. It was that she had mis-timed it, treating rest as the finish line instead of part of the cycle.

In this conversation, Mark and Melisa get into why platitudes like "fail fast" and "fail forward" tend to fall flat, why pre-mortems can prevent faceplants that postmortems can't, and the four autopilot reactions Melisa calls the Conspirators -- the machine, the magician, the statue, and the satellite. They also explore how separating the facts of a failure from the story we tell ourselves about it is often the difference between getting stuck and getting free, what happens when organizations inadvertently create cultures where failure isn't safe, and how AI can be a thinking partner in problem solving rather than a replacement.