Podcast · 25 episodes
Founder Failures: Post-Mortems
About this show
Two founders dissect a business decision that went badly wrong, with the kind of brutal honesty you normally only hear behind closed doors.
All 25 episodes
Latest 3 September 2026
Dead on Arrival: The Launches That Force a Founder’s Hand
Episode 28 · 13 min · 3 September 2026
Two founders dissect the business decisions nobody admits to—failures that teach more than any win ever could.
In this candid podcast episode, two founders dissect failed business launches, offering an unfiltered look at what went wrong and the lessons learned. Their honest conversations reveal the often unseen challenges of decision-making under pressure and emphasize the importance of resilience and adaptability. Listeners will gain practical insights into avoiding similar pitfalls and refining their own entrepreneurial strategies.
Crash Course: The Brutal Truth Behind Startup Pivots Gone Wrong
Episode 27 · 14 min · 27 August 2026
Two founders dissect their biggest business missteps—unfiltered, confessional, and painfully useful.
In this candid episode, two startup founders openly analyze a recent business pivot that didn't go as planned, sharing behind-the-scenes insights and hard lessons learned. Their honest discussion offers valuable takeaways for entrepreneurs navigating tough decisions, highlighting the importance of resilience, adaptability, and learning from failure. Listeners will gain practical wisdom to better handle setbacks and refine their strategic approach.
Founders' Confessional: The Brutal Truths Behind Startup Fails
Episode 26 · 12 min · 20 August 2026
Unfiltered weekly post-mortems on business blunders—insider lessons too useful to keep secret
Join two founders as they pull back the curtain on their biggest blunders, dissecting a different failed business decision each week with raw honesty. This isn't just a post-mortem; it's an unfiltered conversation revealing the painful lessons learned, offering invaluable insights into the common pitfalls that can derail even the most promising ventures. Tune in to gain practical wisdom, avoid costly mistakes, and understand the true grit required to build a successful startup.
Founders' Confessional: The Unfiltered Truth Behind Business Blunders
Episode 25 · 14 min · 13 August 2026
Raw, behind-closed-doors post mortems on startup decisions gone wrong—lessons you can’t afford to miss.
In this candid podcast, two founders openly dissect their most challenging business decisions and the lessons learned from failures. Through honest, behind-the-scenes conversations, they reveal the pitfalls, missteps, and insights that shaped their entrepreneurial journeys. Listeners will gain valuable perspectives on overcoming setbacks, making smarter choices, and embracing transparency in the pursuit of success.
Startup Confessions: The $1.2M Mistake Behind Beacon's 37 Customers
Episode 24 · 12 min · 6 August 2026
Two founders reveal the raw, unfiltered lessons from business decisions gone wrong—no holds barred.
In this candid episode, two founders openly dissect a costly mistake that led to losing $1.2 million and 37 customers for Beacon. Through honest, behind-the-scenes conversations, they reveal the lessons learned, mistakes made, and insights gained from their challenging experience. Listeners will gain valuable strategies for avoiding similar pitfalls, understanding the importance of transparency, and embracing failure as a vital part of entrepreneurial growth.
Brutal Truths: The Real Reasons Nearly Half of New Hires Fail
Episode 23 · 12 min · 30 July 2026
Founders dissect the hidden pitfalls of hiring gone wrong in a raw, no-holds-barred conversation
In this candid episode, two founders delve into the often overlooked reasons why nearly half of new hires fail within organizations. Through honest, behind-the-scenes conversations, they reveal the common pitfalls, missteps, and misalignments that lead to onboarding challenges. Listeners will gain practical insights on improving hiring strategies, fostering better integration, and building stronger teams to boost overall business success.
Founders’ Confessional: The Brutal Truth Behind Failed Business Decisions
Episode 22 · 10 min · 23 July 2026
Unfiltered weekly post-mortems where two founders dissect what really went wrong—so you don’t repeat their mistakes.
In this candid podcast episode, two seasoned founders openly dissect a recent business decision that didn't go as planned. Their raw, unfiltered conversation reveals the lessons learned, mistakes made, and insights gained, offering invaluable guidance for entrepreneurs facing similar challenges. Listeners will gain a deeper understanding of how honest reflection can drive growth and resilience in the startup journey.
Brutally Honest: Founders Unpack Their Biggest Business Blunders
Episode 21 · 12 min · 16 July 2026
Behind closed doors, two founders dissect the missteps that nearly ended their startup dreams in 2026.
In this candid podcast, two founders engage in an unfiltered, no-holds-barred discussion about their most significant business mistakes. By dissecting what went wrong and exploring their lessons learned, they offer invaluable insights for entrepreneurs and business leaders alike. Listeners will gain practical takeaways on avoiding similar pitfalls and embracing transparency to foster growth and resilience.
Brutally Honest: Startup Blunders Unpacked Behind Closed Doors
Episode 20 · 11 min · 9 July 2026
Two founders dissect real business missteps—raw, unfiltered, and too insightful not to share.
In this candid podcast series, two startup founders openly dissect their most costly mistakes and missteps, sharing behind-the-scenes insights that are rarely discussed publicly. Each episode offers valuable lessons on navigating entrepreneurial challenges, emphasizing transparency and learning from failure. Listeners will gain practical takeaways to improve their own decision-making and understand that setbacks are an inevitable part of the startup journey.
Brutally Honest Business Blunders: Founders’ Post-Mortem Sessions
Episode 19 · 10 min · 2 July 2026
Two founders dissect their biggest business missteps—raw, unfiltered, and too insightful to keep secret.
Dive into the raw, unfiltered conversations of two founders as they dissect their most catastrophic business decisions. This series offers a rare, behind-the-scenes look at real-world failures, revealing the critical lessons learned when things go spectacularly wrong. Tune in to gain invaluable insights into common pitfalls and strategic missteps, equipping you to navigate your own entrepreneurial journey with greater foresight and resilience.
Startup Autopsies: Founders Unpack Their Biggest Business Blunders
Episode 16 · 14 min · 11 June 2026
Candid, behind-closed-doors conversations dissecting costly mistakes and what every entrepreneur can learn from them.
Dive into the raw, unvarnished truth of startup failures with 'Startup Autopsies.' Each week, two seasoned founders dissect a business decision that went horribly wrong, offering candid insights as if you're a fly on the wall. This podcast provides invaluable lessons from the trenches, equipping you with the wisdom to navigate your own entrepreneurial journey and avoid common pitfalls.
Brutally Honest: The Post-Mortem Podcast for Startup Stumbles
Episode 15 · 10 min · 4 June 2026
Founders dissect their worst business decisions—raw, unfiltered, and too insightful to stay behind closed doors.
Dive into the unvarnished truth of startup failures with 'Brutally Honest.' Each week, two founders dissect a business decision that went spectacularly wrong, offering raw, unfiltered insights usually reserved for private conversations. This podcast is your essential guide to understanding the real challenges of entrepreneurship, helping you learn from costly mistakes and navigate your own ventures with greater wisdom.
Brutal Boardroom: Startup Post-Mortems That Pull No Punches
Episode 13 · 11 min · 21 May 2026
Two founders dissect their biggest business blunders—raw, unfiltered, and too insightful to keep secret.
Two founders dissect their biggest business blunders—raw, unfiltered, and too insightful to keep secret.
Founders Unfiltered: The Brutal Truth Behind Business Blunders
Episode 12 · 10 min · 14 May 2026
Candid weekly post mortems on epic business decisions gone wrong—insights you were never meant to hear.
Candid weekly post mortems on epic business decisions gone wrong—insights you were never meant to hear.
Brutal Business Blunders: Founders Unfiltered Post-Mortems
Episode 11 · 8 min · 7 May 2026
Candid weekly deep-dives into real startup decisions gone wrong—honest lessons you were never meant to hear.
Candid weekly deep-dives into real startup decisions gone wrong—honest lessons you were never meant to hear.
Brutal Business Blunders: Behind Closed Doors with Founders
Episode 10 · 9 min · 30 April 2026
Candid, no-holds-barred post mortems on startup missteps—lessons from failures you were never meant to hear.
Candid, no-holds-barred post mortems on startup missteps—lessons from failures you were never meant to hear.
Brutal Boardroom: Founders Unfiltered on Business Blunders
Episode 9 · 9 min · 23 April 2026
Behind closed doors, two founders dissect their biggest missteps—raw, honest, and painfully instructive.
Dive into the unfiltered reality of entrepreneurship with 'Brutal Boardroom.' Each week, two founders lay bare a business decision that went spectacularly wrong, offering raw, honest insights typically reserved for private conversations. This podcast strips away the success stories to reveal the hard-won lessons from failure, providing invaluable takeaways for anyone navigating the complex world of business.
Founders' Confessional: The Costly Fallout of One Bad Hire
Episode 8 · 9 min · 16 April 2026
Unfiltered conversations on startup missteps—this week, the inside story of a disastrous product manager hire.
Unfiltered conversations on startup missteps—this week, the inside story of a disastrous product manager hire.
Brutal Boardroom: The Unfiltered Post-Mortem on Business Blunders
Episode 7 · 8 min · 9 April 2026
Two founders dissect the business decisions they wish they could take back—no sugarcoating, just hard-earned lessons.
A boardroom post-mortem argues that failed hires often reflect attitude and motivation more than technical skill, and that interview impressions can hide the person who arrives under pressure.
Startup Confessions: The True Cost of Seventeen Customers
Episode 6 · 7 min · 7 April 2026
Founders dissect their biggest business blunders in candid, behind-closed-doors conversations you need to hear.
A startup post-mortem about Archivist, a B2B SaaS product that shut down after finding only seventeen paying customers. The founders examine acquisition cost, product belief, and the gap between elegance and demand.
Founders' Confessional: The Brutal Truth Behind Startup Missteps
Episode 5 · 3 min · 2 April 2026
Candid weekly post-mortems on business blunders—raw conversations too valuable to keep behind closed doors.
A founder post-mortem about Briefly, an AI legal-document summarizer that launched with a polished product and zero customers. The conversation examines why quality and effort did not create demand.
Unfiltered Failures: Founders' Candid Post-Mortems on Business Blunders
Episode 4 · 3 min · 2 April 2026
Two founders dissect their worst decisions—raw, honest, and full of hard-earned lessons you won't hear elsewhere.
A founder conversation about a failed hire, an overloaded roadmap, and the desperation behind a scaling decision. The post-mortem stays with the uncomfortable reasons the team made the wrong call.
Brutal Business Blunders: The Candid Founders' Post-Mortem
Episode 3 · 4 min · 2 April 2026
Unfiltered conversations dissecting real startup mistakes—what went wrong, why, and what they'd do differently.
A founder post-mortem on a high-profile hire who disrupted a team, contributed to departures, and exposed gaps in interviewing and reference checks. The conversation focuses on conflict, character, and rebuilding trust after a damaging decision.
Brutal Post-Mortems: Startup Decisions Gone Wrong
Episode 2 · 3 min · 2 April 2026
Two founders dissect their biggest business missteps in candid, behind-closed-doors conversations.
A startup post-mortem about building a mandatory Daily Focus feature despite evidence that users wanted the problem solved differently. The founders unpack attachment to vision, market need, and refusal to listen.
Brutally Honest Startup Post Mortems
Episode 1 · 3 min · 2 April 2026
Founders dissect their biggest business blunders in raw, revealing conversations you were never meant to hear.
A startup post-mortem about Prism’s lost users, a spent seed round and the gap between launch excitement and durable traction. The episode follows how a promising beginning turned into a costly lesson in chasing the wrong signal.
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