My Favorite Mistake: Learning Without Blame in Business and Leadership

The Lawyer Mistake That Nearly Killed a Deal: CEO Mike Grossman

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.

Why Speaking Up Backfired Early in Her Career -- with Kate Lowry

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.

A 40-Page Business Plan Is Not a Strategy -- Eric Ries on His First Startup, Incorruptible, and What "Best Practices" Get Wrong

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.

Getting Too Close to What You Love: Joe Hennes (Tough Pigs) on Working at Sesame Workshop

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.

Stop Chasing Results, Start Pursuing Peace of Mind - with Deborah Coviello

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.

Going Gun-Shy as a New Leader: Jesse Jackson on "We Tried That, It Didn't Work"

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.

Processing Failure Without the Funk -- Dr. Melisa Buie

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.

Why Chasing Growth Over Profit Cost This Founder $800K -- with Joel Steele

At 24 years old, Joel Steele was buried in what would be roughly $800,000 of debt in today's dollars - the wreckage of a healthy fast food restaurant chain he had poured himself into since college. He had three locations, media coverage, and a fourth lease in his hand. What he didn't have was a team, a mentor, or a profit.
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In this conversation with Mark Graban on My Favorite Mistake, Joel takes apart what actually went wrong. It wasn't the concept - healthy fast food was ahead of its time. It was that he had set the wrong metric. He was measuring growth instead of profitability. He was doing every job himself. And when warning signs appeared (literally, as sewage backing up four feet high in the middle of a lunch rush), he kept going.
Joel shares the moment he finally took off the blinders, the catatonic stretch that followed, and how he rebuilt - first into a successful financial services firm, and now as the author of Life Switch: How to Experience the Power of Living On. He explains what it means to live "on" versus "off," why he designed a $1 million charitable commitment into the book itself, and what he tells high achievers - including pro athletes - who are trying to figure out what comes next.
A thoughtful conversation about founder blinders, the trap of confusing growth with success, and the psychology of coming back after a public failure.

Why Walking Away from Tech Was the Wrong Move -- with Irna Hutabarat Athans

Irna Hutabarat Athans had an MBA from MIT, connections to VCs, and a front-row seat to the startup world. But technology felt soulless to her, so she walked away -- for years. She became a tango dancer, a poet, a world traveler. Anything but tech.
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That decision cost her years of income and impact. The turning point came at a conference where she asked a room full of hotel and restaurant entrepreneurs what would happen to the families whose jobs AI would eliminate. Most couldn't answer. But one woman told her, "The fact that you asked that question is the very reason you have to lean into AI -- because AI is now driven by people who do not ask those questions."
From there, Irna started using AI not as a search engine but as a thinking partner. She applied chain of thought reasoning to surface limiting beliefs she had carried for years -- about money, about success, about whether someone who loves Greek tragedies belongs in technology. Through those conversations, she arrived at a personal mission: to be a creator, creating something she enjoys, that people will pay for, and that makes the world a better place.
We also talk about what blockchain actually is beyond crypto, why only 6.4% of blockchain VC goes to women-led companies, and why AI, blockchain, and quantum computing need more diverse voices building them.

What Bruce Springsteen's Set List Teaches Leaders About Communication -- with Andy Freed

Andy Freed has seen Bruce Springsteen perform 95 times. Somewhere along the way, he stopped just enjoying the shows and started studying them -- how Springsteen prepares a set list, reads an audience, paces energy across a four-hour performance, and makes every musician on stage feel like the most important person in the room.
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Andy is CEO of Virtual Inc. and author of Lead Like the Boss: The Bruce Springsteen Framework to Elevating Your Leadership. His favorite mistake goes back to 2006, when his team created an Uncle Sam-style "We Want You" marketing campaign for a global organization -- then got a call from their Japanese partner pointing out that American World War II propaganda doesn't exactly resonate in Tokyo. The campaign was already far along, forcing a sharp pivot and a lasting lesson about what happens when you view your audience through a single cultural lens.
From there, we dig into the ideas at the heart of his book: why communication isn't just a leadership skill but is leadership itself, the "think, feel, do" framework for making sure your message actually lands, and why a well-intentioned company cafeteria policy once drove employees to quit. Andy also shares why Tom Peters was right that leadership is a performance, how self-awareness matters more than fixing every weakness, and what it means when Springsteen shakes every band member's hand at the end of every show.