Founder F**K ups

Ben Bagg
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  • Entrepreneurship

Behind every glossy founder story is a graveyard of mistakes, missteps and meltdowns. Founder F**k Ups digs them up. Every week I sit down with a Founder who'll tell you what actually went wrong - the hire they kept too long, the co-founder they gave half the company to, the pivot they made two years late. No humble bragging. No highlight reel. Just the decisions that cost real money and what they'd do differently. Most of my guests are building in Southeast Asia, and most are early enough that the scars are still fresh. Episodes run 25–35 minutes, because you're busy and the lesson doesn't need an hour. If you're making these mistakes in a vacuum, stop. Come and hear how someone else already made them. Hosted by Ben Bagg - Founder coach, 100+ Founders coached one-on-one. www.founderfuckups.co

  1. Sep 11

    Their meeting room is an ice bath, and they're married | Lyv & Paul, The Contrast Club

    One in five startups dies of co-founder fallout. Most co-founders at least go home to different houses. Lyv and Paul go home to the same house, and the same dog. They met through a work enquiry that produced no business whatsoever. Seven years later they were married, and three months ago they opened The Contrast Club, an ice bath and sauna studio in Kuala Lumpur. So for this episode we did the whole thing inside their own protocol. Coffee at the bar, questions in the sauna, rapid fire in the plunge, and the honest stuff in the magnesium bath. Ten weeks after opening they had to shut the doors for four days and strip out work they'd already paid for. The part Paul admits in the ice bath is the part that makes it a Founder F**k ups episode: they could see it coming and kept going anyway. This one gets into: Why a second yes matters more than the first one, and how Lyv knew Paul was finally inWhat actually happens when two people who work at different speeds run one businessSelling a habit instead of a treat, and why that's a business model problem rather than a marketing oneThe packages that didn't sell, and what they changedWhy people who come with a friend buy again more oftenClosing a three-month-old business for four days on purposeWhether a couple's session ever stays a couple's session Lyv and Paul are the rare pair who answer the co-founder question honestly rather than sweetly. If you're thinking about starting something with your partner, watch the last five minutes before you do. CHAPTERS 00:00 A work enquiry that led to no business 01:00 The dinner table, and Paul's hesitation 02:10 The second yes, and how Lyv knew 03:45 The walkthrough: what they took from onsens, bathhouses and New York 05:30 What contrast therapy actually does 07:00 Why founders in particular need somewhere to put it 08:20 The paint job, and closing four days in month three 10:10 Habit, not treat: the retention problem 13:00 What didn't sell, and the fix 14:20 Two speeds: the event that went sideways 15:30 Does it stay out of the house? 17:00 Rapid fire, three degrees 19:25 The magnesium bath: it always turns into a meeting 21:30 Advice to a couple thinking about it GUEST Lyv & Paul, co-founders, The Contrast Club, Kuala Lumpur FOUNDER F**K UPS The podcast where Founders talk about the thing that actually went wrong. www.founderfuckups.co youtube.com/@founderfuckups #founderfuckups #startups #cofounders #kualalumpur #contrasttherapy #icebath #smallbusiness #foundersjourney #malaysia #entrepreneurship

    Their meeting room is an ice bath, and they're married | Lyv & Paul, The Contrast Club

  2. Sep 4

    15 Years In Private Equity, One Year Lost To A Dev House | Wes Barnes, Associum

    In 2022, Wes Barnes had everything a Founder is supposed to need. He just had no way to build it. Wes spent 15 years in private equity. He built and sold a fund platform he had been quietly trying to make smarter with AI back in 2018, years before anyone was calling that a category. When he started again he knew the customer, because he had been the customer. He had a network that opened doors to VCs and buyers. And the smartest people around him agreed the idea was good. He is not technical. People told him to go and find a technical co-founder. He heard them and decided it could wait, because he had managed dev teams before and figured he could manage some more. So he went to dev houses instead. A dev house delivers the scope and nothing else. Every change is an expansion and another quotation. And 2022 was the year the whole industry moved from machine learning to generative AI, so the product kept changing underneath him while he was paying by the scope. He ended up faking demos in CustomGPT just to have something on a screen. In every meeting, once everyone had agreed the opportunity was real, came the same line: okay, but can you show me the product? That cost him the best part of a year. This one gets into what that year actually bought him. Why the dev shop model is built for companies that already have technical people to manage it, and breaks at startup speed. The pivots he paid for twice. The long dating period with the co-founder who eventually reached out to him, and the values conversation that convinced them both. What happened in the first ninety days: a team he could never have recruited on his own, an MVP in six months, a commercial product six months after that. How they split equity when one of them had already spent the money, and why "until you have something, you have nothing" was the only way he could look at it. And the poker question he now asks before he spends a single cent. Wes is a Founder who did everything right except the one thing everyone told him to do. If you are about to sign with a dev house, or you have convinced yourself that Cursor and Lovable mean you can skip the technical co-founder, watch the last ten minutes twice. CHAPTERS 00:00 "Can you show me the product?" 00:15 Selling venture one and starting again 04:21 The advice he heard and parked for later 06:33 Why a dev house instead of a co-founder 09:50 "That model is not designed for startups" 11:03 Faking demos with CustomGPT 13:47 The meetings where the idea was never the problem 17:39 The long dating period with Vishal 21:29 What changed in the first ninety days 23:36 "Until you have something, you have nothing" 26:51 Could Replit and Lovable have saved him? 30:05 The poker question before you spend a cent GUEST Wes Barnes, Founder, Associum LinkedIn: /in/wesleybarnes2 FOUNDER F**K UPS The podcast where Founders talk about the thing that actually went wrong. Website: https://www.founderfuckups.co YouTube: /@founderfuckups #FounderFuckUps #Startups #Founders #CoFounder #PrivateEquity #AI #DevShop

    15 Years In Private Equity, One Year Lost To A Dev House | Wes Barnes, Associum

  3. Aug 28

    Worth €67 Million On Paper, Firing Staff The Same Week | Chris J Reed, Black Marketing

    In 2016, Chris J Reed was worth 67 million euros. He couldn't touch a single one of them. Chris had built Black Marketing from nothing in Singapore. Three profitable years in, one of the founders of a roll-up called The Marketing Group approached him with a plan: buy four agencies, list on the Nasdaq in Sweden, scale everybody. Chris said yes. He owned 25% of a company that hit a quarter of a billion euros in market cap inside two months. Then he tried to borrow against it. Ten banks said no. Not one of them thought it was a substantial company. While the share price was climbing, the actual business wasn't. The promised synergies didn't exist, because the other agencies were B2C and he was B2B. He was flying to Sweden, drinking champagne and ringing the bell, and firing his own staff in a Singapore co-working space at the same time. His team thought he was a millionaire and had stopped trying. Then his divorce lawyers found the Nasdaq listing. The first draft of the settlement had him paying his ex-wife ten million dollars against money that did not exist. He renegotiated when the share price collapsed, but it started from an artificial number, and he is still paying against it ten years later. This one goes deep on what a roll-up actually costs a Founder. The deals announced on the Nasdaq before they were signed. The Sydney hotel meeting where Chris congratulated two agency founders on joining the group and they had no idea what he was talking about. The 19 missed calls and the threat to report him to the police. Three CFOs in a single year. And how he got out: closing the Singapore entity they had bought, moving every client into the Hong Kong entity they hadn't, and rebuilding leaner with teams in the Philippines and South Africa. Chris is a Founder who ended up worth less than he sold for, spent what was left on lawyers, and had to explain to every new prospect why his company still existed. He built the brand back anyway. If you have a term sheet, an earn out or a lovely paper valuation sat in your inbox right now, watch the last ten minutes twice. CHAPTERS 00:00 67 million euros he could never touch 01:35 "There's a Nasdaq in Sweden?" 06:47 25% of a quarter of a billion 08:01 Ten banks said no, and he ignored it 10:21 Ringing the bell while firing staff 11:52 The synergies that never existed 12:41 When your divorce lawyer finds the share price 14:56 Sydney: the deals that hadn't actually happened 17:33 19 missed calls and a threat to call the police 20:11 Founders out, bean counters in, shares under one euro 22:18 They bought Singapore. They didn't buy Hong Kong. 24:19 "You're fired, you're fired, you're fired" 26:10 When Google becomes your biggest objection 27:48 The question to ask before you sign anything 32:15 What he'd do differently GUEST Chris J Reed, Founder & Global CEO, Black Marketing LinkedIn: https://www.linkedin.com/in/theonlyceowithamohawk/ Black Marketing: https://blackmarketing.com FOUNDER F**K UPS The podcast where Founders talk about the thing that actually went wrong. Website: https://www.founderfuckups.co YouTube: https://youtube.com/@founderfuckups #FounderFuckUps #Startups #Founders #Singapore #Nasdaq #Acquisition #LinkedIn

    Worth €67 Million On Paper, Firing Staff The Same Week | Chris J Reed, Black Marketing

  4. Aug 21

    My CTO quit with no runeway left with Glenn Tan

    Glenn Tan is co-founder and CEO of Zavior, the Singapore RegTech using AI to get teams compliance-ready on PDPA, ISO and everything buyers ask for. He is a sales and partnerships founder. So he did what almost every non-technical founder does: he left the building to the person who builds. Then the product ran badly behind, the money ran out, and his technical co-founder left. Two options. Ship fast or shut it down. Glenn took over the tech himself while still running sales, delivery and partnerships, and inside a year they built every feature they had wanted since day one. This one is about what it costs to outsource the thing your company is made of, and what you find out about yourself when the floor goes. Takeaways "Almost there" is the warning sign. Every almost there hid two more things to do, and they piled up while he kept selling what was still in progress.His co-founder leaving was not dramatic and not personal. It was money plus a gap too expensive to close.Talking to more people can be a way of delaying the call. At some point it is your decision and nobody else's.The blocker was never the tech. It was fear of starting things that used to take too long.Domain expertise is the new advantage in building. If you know what the client wants, you can now build it yourself.Build the functionality of the city first, then the piping.Chapters 00:00 Losing a CTO with no runway left01:12 Clients on the books, product way behind03:43 What the delay did to the money04:33 Climb Everest, or take the helicopter05:40 He builds, I sell, and the first cracks06:33 The "almost there" trap07:49 Did you see the quit coming?08:58 Money or product: the real breaking point09:35 The first ten seconds after "I'm out"10:43 Ship fast or shut it down12:49 The conversation with his wife15:13 Why he picked up the tech himself17:05 Cursor, and fear as the actual blocker18:10 Three to six months of hammering20:47 "I lost a limb, but I'm on a rocket ship"21:08 Why domain experts are the best builders now25:57 For the founder one resignation away

    My CTO quit with no runeway left with Glenn Tan

  5. Aug 14

    Right Partnership, Wrong Timing with Dan Gericke

    Dan Gericke, co-founder of Shift Control and former CTO at Express VPN, shares his experience with AWS partnership, compliance challenges, and the impact on sales. The conversation explores the partnership mirage, compliance issues, and the importance of early sales cycles. The conversation delves into the challenges and insights of partnering with AWS and the impact on a startup's growth. It explores the ROI, time investment, and considerations for founders when entering a partnership program. Takeaways Partnership MirageCompliance Challenges Partnership programs like AWS require significant time investment and may not yield immediate ROI.Founders should focus on direct sales and partnerships, avoiding distractions from ecosystem partnerships. Chapters 00:00 The AWS Partnership Mirage03:03 The Compliance Challenge12:50 Navigating the Sales Cycle17:52 The ROI of Partnership18:21 Navigating the AWS Ecosystem19:06 Challenges of Startup Partnerships26:01 The Impact on Product Development30:32 Considerations for Founders

    Right Partnership, Wrong Timing with Dan Gericke

  6. Aug 3

    Lowering Recruitment Standards with Sugasini Kandiah

    The conversation delves into the challenges of bad hiring choices, the impact of bad hires on business growth, the consequences of lowering the hiring bar, the cost of bad hires and self-doubt, overcoming hiring mistakes, rebuilding the recruitment process, assessing critical thinking and problem-solving, the importance of methodical hiring, and lessons learned for moving forward. Takeaways The importance of owning the recruitment process as a founder of a small teamThe need for methodical hiring and assessment of critical thinking and problem-solving skills Chapters 00:00 The Pitfalls of Bad Hiring Choices03:01 The Impact of Bad Hires on Business Growth05:58 Lowering the Bar and Its Consequences09:02 The Cost of Bad Hires and Self-Doubt12:01 Overcoming Hiring Mistakes and Building Confidence15:04 Rebuilding the Recruitment Process18:05 Assessing Critical Thinking and Problem Solving20:53 The Importance of Methodical Hiring24:02 Lessons Learned and Moving Forward

    Lowering Recruitment Standards with Sugasini Kandiah

  7. Jul 7

    The Founder Commitment Gap with Lizzie Tan

    Lizzy Tan, co-founder of Cleve AI, shares her experience with the co-founder commitment gap and the challenges of early stage recruiting. She discusses the impact of juggling multiple responsibilities and the importance of effective communication in building successful business relationships. Takeaways Co-founder commitment gapEffective communication is key Chapters 00:00 Introduction and Co-founder Commitment Gap06:06 Recruiting a Technical Co-founder12:00 Challenges of Juggling Responsibilities and Communication

    The Founder Commitment Gap with Lizzie Tan

  8. Apr 2

    The Hidden Cost of Shiny Object Syndrome with Adam Chambers

    Are you a founder constantly looking for the "next big thing"? You might be suffering from Shiny Object Syndrome. In this episode of Founder F**k Ups, Ben Bagg sits down with Adam Chambers, serial entrepreneur and founder of Nurse Recruitment Experts, to discuss the dangerous trap of chasing new ideas instead of focusing on what actually works. Adam shares his costly $7,500 mistake of investing in a new job board that yielded zero results, and how it distracted him from his core business engine. We dive deep into the opportunity cost of lost focus, the importance of doubling down on proven strategies, and why the most boring advice in business is often the most profitable. If you're a founder struggling with focus, hiring mistakes, or knowing when to kill a failing experiment, this episode is packed with actionable insights to help you stay on track. Key Takeaways: •Why doubling down on your core engine beats chasing new channels. •The real cost of Shiny Object Syndrome isn't just money—it's lost time and focus. •How to know when to pull the plug on a failing experiment or bad hire. •The importance of matching your offer to market demand (and the Mexican Fish & Chips analogy!). •A practical framework for calculating ROI and the cost of inaction before starting new projects. Chapters 0:00 - Introduction: The Trap of Shiny Object Syndrome 0:37 - Adam's $7,500 Mistake: Investing in the Wrong Job Board 2:29 - Why Doubling Down Beats Chasing New Platforms 4:13 - The Role of Emotion vs. Logic in Sales and Investments 5:21 - Recognizing Vanity Metrics and Failing Experiments 7:11 - Hiring Mistakes: The Cost of Distracting Your Team 9:06 - The Real Tragedy: Lost Time and Compound Effects 11:25 - The $5 vs. $500 Task Framework for Founders 12:23 - How to Know When to Pull the Plug on a Bad Hire 15:16 - Interviewing for Culture and Behaviors 17:48 - The Most Important Thing: Supply, Demand, and Your Offer 19:50 - The Mexican Fish & Chips Analogy: Market Misalignment 21:44 - Why Founders Avoid Speaking to Customers 23:49 - A Framework for Calculating ROI on New Initiatives 26:34 - Valuing Your Time and the Cost of Inaction 30:14 - Final Advice for Founders: Protect Your Profits and Do the Math #ShinyObjectSyndrome #FounderMistakes #BusinessGrowth #Entrepreneurship #StartupAdvice #Focus #ROI #HiringMistakes #FounderFuckups #BusinessStrategy #AdamChambers #BenBagg

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About

Behind every glossy founder story is a graveyard of mistakes, missteps and meltdowns. Founder F**k Ups digs them up. Every week I sit down with a Founder who'll tell you what actually went wrong - the hire they kept too long, the co-founder they gave half the company to, the pivot they made two years late. No humble bragging. No highlight reel. Just the decisions that cost real money and what they'd do differently. Most of my guests are building in Southeast Asia, and most are early enough that the scars are still fresh. Episodes run 25–35 minutes, because you're busy and the lesson doesn't need an hour. If you're making these mistakes in a vacuum, stop. Come and hear how someone else already made them. Hosted by Ben Bagg - Founder coach, 100+ Founders coached one-on-one. www.founderfuckups.co

Information

  • Creator
    Ben Bagg
  • Years Active
    2025 - 2026
  • Episodes
    30
  • Rating
    Explicit
  • Copyright
    © 2025 Ben Bagg