Not Another CEO Podcast

Not Another CEO
  • 5.0 (16)
  • Entrepreneurship
  • Updated Weekly

Our mission is to bend the curve for Founders and CEOs. At Not Another CEO, we know there’s no formula for running a business. Leadership is forged through unique journeys, real challenges, and hard lessons. Our exclusive content showcases unfiltered stories and practical guidance from those who’ve crawled through the trenches. Our platform offers the largest library of CEO insights and how-to guides, sourced directly from a diverse community of leaders. Find our full video library, detailed playbooks, deep dives, and lessons learned on our Substack here ➡️ https://notanotherceo.substack.com/

  1. Better to Be Fast than to be Right - Jessica Lin - Work-Bench - Episode #102

    1d ago

    Better to Be Fast than to be Right - Jessica Lin - Work-Bench - Episode #102

    Most founders think investors decide after the pitch but this investor says the decision is usually made in the first five minutes. In this episode of Not Another CEO, I sat down with Jess Lin, Co-Founder & General Partner at Work-Bench, for a deep conversation on what actually separates great founders from everyone else. Jess breaks down how investors build conviction in founders within minutes, why product-market fit has become harder than ever, and what most startups misunderstand about growth, fundraising, and becoming truly mission critical. The conversation also explores the emotional side of venture capital, imposter syndrome, building a venture firm, and the realities founders face between Seed and Series A. From founder obsession and investor psychology to career risk and company building, this episode is a candid look into how elite investors think and what founders need to understand to build enduring companies. Takeaways:Investors Often Decide Faster Than Founders Realise: Jess explains that initial conviction about a founder is usually formed within minutes. The rest of the process is often about validating or disproving that instinct.Growth Alone Is No Longer Enough: Fast revenue growth has become table stakes. The real question investors ask now is: Would customers genuinely care if this product disappeared tomorrow?Founder Obsession Matters: The best founders are deeply obsessed with the problem they’re solving. They see something others don’t and cannot stop thinking about it.Venture Capital Is Emotionally Uncertain: Jess shares how difficult it is to know whether you’re actually “good” at investing because feedback loops in venture can take 10+ years.Building a VC Firm Is Like Building a Startup: From branding and hiring to differentiation and operations, venture firms face many of the same challenges founders do when building companies.Quote of the Show:It's better to be fast than to be right. Because if you're fast, if you just have more at bats, you will least be able to course correct. - Jessica Lin, Co-Founder & General Partner at Work-Bench. Links: LinkedIn: https://www.linkedin.com/in/jessicalin8 Work-Bench: https://www.work-bench.com/ Chapters:00:00: Trailer 04:12: How investors evaluate founders in the first five minutes 09:35: The founder traits that create investor conviction 15:08: Why Series A has become much harder 20:44: What “mission critical” really means in startups 27:10: Product-market fit vs fast growth 33:26: Imposter syndrome in venture capital 39:41: Career advice, risk & serendipity 46:03: Why building a VC firm feels like building a startup 53:18: Final lessons for founders and investors

    1h 4m
  2. The Seven Deadly Sins of Founders - Michael Loeb - Loeb.Nyc - Episode #101

    May 26

    The Seven Deadly Sins of Founders - Michael Loeb - Loeb.Nyc - Episode #101

    Most founders fail before the market ever gets the chance to beat them the enemy is inside the building. In this episode of Not Another CEO Podcast, David sits down with Michael Loeb, Co-Founder of Synapse Group and founder of Loeb Enterprises, a startup studio and venture collective that has invested in, incubated, and scaled more than 50 companies including five unicorns. Michael shares the hard-earned lessons from 35 years of building: the character flaws that destroy founders before the market ever gets the chance, what separates real entrepreneurial DNA from people who just like the idea of it, why sociopaths concentrate in startups, and why the entrepreneurial class should be funding itself instead of depending on traditional venture capital. Takeaways: 1. The character flaws that kill founders are predictable: Michael maps pride, sloth, delusion, and the refusal to listen onto real founder failure stories. 2. Entrepreneurship is innate, not learned: Real founders show up early the lemonade stand, the paper route, the video game rental business in college. 3. Surrender being an option is a dealbreaker: The moment a founder puts quitting on the table, Michael says the relationship is over. 4. Charm is a feature and a warning sign: Sociopaths concentrate in startups because magnetic charm and the ability to make fiction feel real are exactly the qualities that attract early capital. 5. The entrepreneurial class is rich enough to fund itself: Michael's Uncharted model is built on a simple premise: founders who have had exits, understand the journey, and can write a $10,000 check should be backing each other not waiting on institutional capital that is fundamentally optimising for something different. Quote of the Show: "When anybody uses those words I'm just going to give up if that is an option, you have no choice. Surrender is not an option. Quitting is not an option. So as soon as that goes on the table, they're done." - Michael Loeb, Founder & CEO, Loeb Enterprises Links: LinkedIn: https://www.linkedin.com/in/michaelloeb1/ Website: https://loeb.nyc/ Ways to Tune In: Substack: https://notanotherceo.substack.com/ Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Chapters: 00:00 - Trailer 03:45 - The seven deadly sins of founders and the pride that bankrupted a $100M business 06:36 - Sloth, the founder who quit, and why surrender can never be an option 13:35 - How Michael spots real entrepreneurial DNA before writing a check 15:43 - The video game rental kid and what genuine founder instinct looks like in college 20:00 - Envy and why rent-a-CEOs create a different kind of danger 22:00 - The thin line between necessary optimism and dangerous delusion 24:53 - Why charm is both a feature and a warning sign 26:16 - The founder who refuses to listen 31:19 - Why being numeric is a non-negotiable founder requirement 34:58 - Founders Backing Founders

    1h 15m
  3. Why CEO's Do It Anyway: Lessons I Learned Talking To 100 Founders - NAC - Episode #100

    May 19

    Why CEO's Do It Anyway: Lessons I Learned Talking To 100 Founders - NAC - Episode #100

    100 episodes. Over a thousand years of combined CEO experience. Every guest showed up for one reason: to pay it forward. Two years ago I was recording in the corner of my son's bedroom. Everyone said I'd quit after ten episodes. I didn't. And in this episode I went back and pulled the moments that stopped me cold the lessons I keep referencing, the stories that hold up no matter what stage you're at. If you're deep in it right now, this one's for you. Links in the comments. If you enjoy the episode, please like and subscribe on your favorite platforms and share with your network. If you enjoy the episode, please like and subscribe on your favourite platforms and share with your network. TAKEAWAYS1. The best founders are just built different and they know what they signed up for. Chieh Huang's description of entrepreneurship as a broken glass eating competition is the most accurate thing I've heard in 100 episodes. 2. The minute you lose hope, it's over. Ryan Simonetti watched Convene go from $220M in revenue and a pre-IPO round in process to zero revenue in less than three weeks. His lesson: optimism isn't soft. It's the one thing that kept Convene alive long enough to become what it is today. 3. Layoffs cost more than headcount and founders feel it in ways they don't talk about. Alina Vandenberghe described being hospitalized after Chili Piper had to do layoffs. That vulnerability is exactly what I built this show to surface. 4. Every company that wants to survive the AI era will have to refound itself. Shensi Ding walked me through a moment at Merge where a major deal collapsed, morale cratered, and people quit. The refounding wasn't a failure it was the only path to becoming a category leader. 5. Most companies don't die of starvation. They die of indigestion. Amish Jani's line is the one I share most with founders I advise. Tight sequencing and disciplined focus are what separate great companies from the ones that almost made it. 6. Fish in a pond, not an ocean. Tom Buiocchi's ICP framework is the most actionable thing I've pulled from the show. When you know the names of all the fish in your pond, your entire go-to-market changes. 7. The chip on your shoulder is fuel don't waste it. Flint Lane told me he's still trying to prove something to the kids he grew up with. That drive didn't diminish after selling Billtrust for $1.7B it followed him into his next company. 8. AI is fast, but it's not without precedent. Donna Dubinsky has lived through desktop computing, handheld computing, the internet, and now AI. Her perspective that the current shift is significant but not categorically unlike what she's seen before is one of the most grounding things I've heard on the show. 9. Being second can be a strategic advantage. Max Junestrand watched the first movers in legal AI burn money on fine tuned models and approaches that didn't pan out. By moving second, Legora could see which paths led nowhere. 10. Real conviction is unmistakable. Jess Lin described meeting April Co, founder of Spring Health, years before the company became what it is. The way she said it made clear: she was doing this with or without any investor. TIMESTAMPS00:00 - Introduction 02:10 - What this show was always meant to be 03:45 - The broken glass eating competition 05:30 - The cost of layoffs no one talks about 08:00 - The chip on the shoulder that never leaves 09:30 - $220M to zero and keeping hope alive 13:00 - What it means to refound from scratch 15:30 - Most companies don't die of starvation 17:00 - Fish in a pond, not an ocean 19:30 - AI through the eyes of someone who's seen everything 22:00 - The second-mover advantage 24:30 - What real founder conviction sounds like 26:30 - Closing

    20 min
  4. How it was game over for Guidewire until it wasn’t - Marcus Ryu - Guidewire - Episode #99

    May 12

    How it was game over for Guidewire until it wasn’t - Marcus Ryu - Guidewire - Episode #99

    Building software is hard but building a category-defining enterprise company for 20 years is a different game entirely. In this episode of Not Another CEO Podcast, David sits down with Marcus Ryu, Co-Founder and former CEO of Guidewire, the software platform that transformed the insurance industry and grew into a public company generating over $1.5 billion in revenue. Marcus shares the hard-earned lessons from building Guidewire from zero: developing strategic clarity, surviving years-long sales cycles, learning how to sell as a founder, navigating investor pressure, handling lawsuits from incumbents, and sustaining the emotional intensity of being a founder CEO for nearly 20 years. This conversation is a masterclass on company building, resilience, leadership, and the psychological realities behind building enduring businesses. Takeaways:1. Strategic coherence matters more than speed:Marcus explains how Guidewire constantly revisited its assumptions whenever new information appeared maintaining ruthless intellectual honesty around strategy instead of blindly executing. 2. Every founder must learn how to sell:Despite not coming from sales, Marcus says learning sales became one of the most valuable skills of his entire career. Great CEOs are constantly persuading customers, employees, investors, and markets. 3. Enduring companies require patience:Guidewire’s early sales cycles lasted 1–2 years, and implementations could take another 1–2 years. Marcus shares why building meaningful companies often demands long-term thinking and delayed gratification. 4. Capital efficiency creates resilience:Guidewire raised only $29 million throughout its journey to IPO. Marcus discusses how treating every dollar like it could be the last shaped the company’s discipline and culture. 5. Intensity without serenity can become dangerous:Looking back, Marcus says he spent years carrying catastrophic pressure and anxiety as a founder. His biggest reflection is learning that great CEOs can be both intensely driven and internally calm at the same time. Quote of the Show:“If you can be intense and serene at the same time, then you really have a superpower.” - Marcus Ryu, Founder & Former CEO, Guidewire Chapters:00:00 - Trailer 02:10 - The importance of strategic coherence in company building 08:45 - Why startups need an enemy and a clear sense of differentiation 15:20 - Discovering the broken insurance software market 27:20 - Learning sales as a founder CEO 31:00 - Getting the first customers & surviving long enterprise sales cycles 36:20 - Building Guidewire with extreme capital efficiency 43:10 - The pressure modern founders feel to grow at impossible speeds 49:40 - Surviving lawsuits and competitive attacks from incumbents 58:00 - Transitioning from founder CEO to investor at Battery Ventures 01:06:30 - Marcus’s biggest personal reflection after two decades as CEO

    1h 15m
  5. From Sticky Notes on My Door to $1.5B Logistics Disruptor - Itamar Zur - Veho - Episode #98

    May 5

    From Sticky Notes on My Door to $1.5B Logistics Disruptor - Itamar Zur - Veho - Episode #98

    He walked back to his apartment and found 50 sticky notes on the door. "Sorry we missed your package." That problem became a $1.5 billion company competing directly with UPS and FedEx. Itamar Zur, Co-Founder and CEO of Veho, shares the full story of building one of the most disruptive logistics companies in America from a business school dorm room to 65 markets, nearly 1,000 employees, tens of thousands of drivers, and over $300 million raised from General Catalyst, SoftBank, and Tiger Global. In this conversation, Itamar opens up about what it really took: obsessing over the Day One customer experience in a way most founders never do, rebuilding the company's values from scratch after 2022 nearly broke everything, and creating a deliberate program to identify and invest in top performers before someone else does. If you're building a company and want to understand what championship-level execution actually looks like from the inside, this episode is worth your time. Takeaways: Obsess Over the Day One Experience: Itamar would send detailed end-of-day reports not just to his buyer but to the CEO, CMO, and CFO of every new customer anyone whose email he could find. By the next call, those buyers weren't asking how things were going. They were asking what other markets Veho could go to. First impressions compound.Values Must Evolve as the Company Evolves: Veho launched with human-first, idealistic values. When the market turned in 2022 and performance management became non-negotiable, those values created internal friction. Itamar rebuilt them from scratch around a championship team mentality. The wrong people left. The right people finally had language for what they had been doing all along.Your 10X People Know They Are 10X Invest in Them Before Someone Else Does: High performers don't complain, don't ask silly questions at all-hands, and quietly deliver results every single day.The Co-Founder Decision Is the Most Important One You Will Make: Two original co-founders left over a fundamental strategic disagreement. Itamar refused to compromise on the vision, finding Fred one person he had met once at a conference changed the entire trajectory of the company.This Is a Marathon Protect the Runner: When the market shifted, the mental and physical toll hit all at once. He now meditates, exercises, sleeps 7–8 hours, and treats it the same way a professional athlete treats training. Everything else depends on it. Quote of the Show: "The way you do anything is the way you do everything." - Itamar Zur, Co-Founder & CEO, Veho Links: LinkedIn: https://www.linkedin.com/in/itamarzur/ Veho Website: https://www.shipveho.com/ Chapters: 00:00 – Intro: From a sticky note to a $1.5B logistics company 01:19 – The one thing: obsessing over the Day One customer experience 05:30 – Sending reports to the CEO, CMO, and CFO why it worked 09:45 – The moment of truth: lessons from Procter & Gamble 14:20 – Veho's original values and why they had to change 18:05 – Championship team mentality: rebuilding culture mid-flight 22:40 – How top performers act and why they never speak up 27:15 – The Force Multipliers program: investing in your all-stars 31:50 – Finding Fred: the co-founder story 38:30 – 2022: the year that almost broke everything 46:00 – The coach conversation that changed how he leads 52:00 – Taking care of your body and mind as a founder 58:10 – Advice to his younger self: give yourself time to learn

    1h 9m
  6. The 10 Step Hiring Framework - April Pulse - Episode #97

    Apr 28

    The 10 Step Hiring Framework - April Pulse - Episode #97

    Description: Most companies don’t fail because of bad strategy they fail because of bad hires. In this solo episode, David Politis breaks down a battle-tested 10-step interview framework built from 20+ years of experience, hundreds of CEO conversations, and real-world hiring mistakes. From uncovering the real motivations behind a candidate’s story to spotting red flags most interviewers miss, this episode is a masterclass in hiring with intention. David challenges the common belief that “people are your greatest asset” and reframes it: the right people are everything. Because the cost of getting it wrong isn’t just time it can be millions in lost value, broken teams, and missed opportunities. Takeaways : 1. “The right people” > just “people”: Hiring isn’t a volume game. One wrong hire especially at leadership level can cost millions in enterprise value and derail entire teams.2. Most companies are “winging” interviews: Very few leaders are formally trained in hiring. Lack of structure leads to poor candidate experience, wasted leadership time, and bad hires.3. Depth beats polish in interviews: Great candidates can go into the details. If someone can’t get into the weeds metrics, decisions, outcomes that’s a major red flag.4. The power of “why” questions: Asking layered “why” questions helps you move past rehearsed answers and uncover true motivations, decision-making, and character.5. Hiring is about alignment, not just capability: Understanding what energizes a candidate and where they want to go is critical. Even great talent fails when there’s misalignment with the role. Quote of the Show : "The reality is that we're winging it. And the cost of winging it is very, very high. The cost of hiring the wrong person there could be literally millions, if not tens of millions of dollars of enterprise value lost." - David Politis, Host of Not Another CEO Chapters 00:00 – Why hiring is the highest-leverage decision you make 06:14 – “The right people” vs. just people 08:30 – The hidden cost of bad hiring decisions 11:00 – Why most companies are winging interviews 13:30 – The importance of preparation and alignment 16:00 – The power of taking decision-grade notes 18:30 – Step 1–3: Setting the tone, story, and “why” questions 21:00 – Going deep: testing real experience and competence 25:00 – Finding what energizes candidates 29:00 – Anti-selling the role + spotting red flags in questions

    28 min
  7. He Lost Everything Twice…But Didn’t Stop Building - Rob LoCacsio - LivePerson - Episode #96

    Apr 21

    He Lost Everything Twice…But Didn’t Stop Building - Rob LoCacsio - LivePerson - Episode #96

    What happens when the company you built… is no longer yours? Rob LoCascio, Founder of LivePerson, shares the full, unfiltered reality of building, scaling, losing, and rebuilding as a founder. From starting with almost nothing to taking his company public, scaling it from $900M to $4B in just 12 months during COVID and then facing the brutal reality of losing control of what he built. In this conversation, Rob opens up about the hardest chapter of his career: fighting to hold onto his company, the emotional toll of watching it decline after his departure, and the moment he realized that everything he created was at risk. He also dives into what separates founders who come back from those who don’t, why creativity is the one asset no one can ever take from you, and how to rebuild your identity when the company you built is no longer yours. This isn’t just a story about success or failure it’s about ownership, resilience, and what it really means to be a builder. If you’re building something or afraid of losing it this episode will hit hard. Takeaways: They Can Take the Company, Not the Builder: Rob’s biggest realization came after losing control everything external can be stripped away, but your ability to create, build, and execute is untouchable. That’s the real edge founders have. Scaling Fast Comes With Hidden Risk: Going from $900M to $4B in 12 months sounds like a dream but hypergrowth brings pressure, expectations, and fragility that most people don’t see until it’s too late. Founder Identity Is the Real Battle: Losing a company isn’t just financial it’s deeply personal. Rob breaks down what it feels like to lose something you poured your life into, and how to rebuild from that. Fighting for What You Built Isn’t Optional: When things started slipping, Rob didn’t walk away he fought. And he explains why that fight was the hardest thing he’s ever faced as a leader. Your Gift Is the Only Constant: Markets change, companies rise and fall but your creativity, vision, and ability to build are the only things that stay with you for life. Quote of the Show: "They can take your company. They can take your money. But they can’t take your creativity, the ability to build again." - Rob LoCascio Links: - LinkedIn: https://www.linkedin.com/in/rlocascio/ - LivePerson: https://www.liveperson.com - KID Company: https://www.kidco.ai/ - Uare.ai: https://www.uare.ai/ Chapters: 00:00 – Intro 01:19 – From nothing: $5K, a couch, and starting over 02:10 – Building LivePerson and going public 05:30 – The COVID surge: $900M to $4B in 12 months 09:45 – When things started to break 14:20 – Losing control of the company he built 18:05 – The hardest fight of his career 22:40 – Watching the company decline after leaving 27:15 – The emotional toll of losing everything 31:50 – Identity beyond the company 36:10 – Why founders can always build again 41:25 – Creativity as the ultimate unfair advantage 46:00 – What Rob is building next 50:30 – The real meaning of success and failure

    1h 9m
  8. Not Taking Money Off the Table Can Cost You Everything - Ra’anan Cohen - Bringg & MobileMax (#95)

    Apr 14

    Not Taking Money Off the Table Can Cost You Everything - Ra’anan Cohen - Bringg & MobileMax (#95)

    What really happens when you bet it all on your company & end up with nothing? Ra'anan Cohen, Author & Founder of MobileMax and Bringg, pulls back the curtain on what most founders never talk about going from IPO to broke, rebuilding from zero, and finally selling at a $1 billion unicorn valuation with the scars to prove it. In this conversation, he shares why he turned down $10M in stock at a public company and lived to regret it, how he secretly rebuilt himself while the whole industry thought he was already rich, and what changed at Bringg that made him finally know when to pull the plug. If you're building something and trying to figure out when to hold and when to fold, this episode is for you. Takeaways: Build the Team First, Everything Else Second: The single biggest factor in both MobileMax and Bringg was team. Ra'anan implemented a strict no-a*****e policy at Bringg not just hiring for talent, but for personality, attitude, and the ability to endure a long, grinding journey.Know When to Take the Money: Turning down $10M in stock from institutional investors during MobileMax's IPO when the company was worth $100M cost Ra'anan everything. He walked away from Bringg at $1B because the 8-year scar from MobileMax kicked in.Fake It Till You Make It Has a Dark Side: After MobileMax collapsed, Ra'anan went to startup meetups while secretly broke and struggling watching everyone else perform success. He later learned everyone was doing the same thing. His book, Confessions of a Unicorn Founder, exists specifically to break this culture open.Secondary Is a Founder's Right, Not a Weakness: Old-school investors want founders "hungry." Ra'anan disagrees. Taking secondary closes the open loops in your brain the daily stress about going to zero and actually frees founders to dream bigger and swing harder, not less. Quote of the Show: "People like to say startup is like a roller coaster. I think this is very misleading. In the startup life as a founder, 90, 95% of the time I'm in crisis mode. It's not a roller coaster it's a marathon." - Ra'anan Cohen, Author & Founder of MobileMax & Bringg Links: Book: Confessions of a Unicorn Founder - available on AmazonLinkedIn: https://www.linkedin.com/in/raananc/Website: www.raanancohen.com Chapters: 00:00 – Intro: From IPO to zero to unicorn Ra'anan's full arc 01:22 – The one thing that had the biggest impact: team building 06:00 – The no-a*****e policy and how to hire for attitude 08:50 – Framing hard weeks as progress the "great week" mantra 13:48 – MobileMax: the IPO, the $10M phone call, and saying no 16:32 – Why Ra'anan didn't sell a single stock and what it cost him 18:54 – When the iPhone reshaped mobile and MobileMax spiraled 25:05 – Broke and "the guy who made it" faking it at startup meetups 32:14 – The personal cost: family, presence, and the founder's obsession 34:13 – How a late pizza sparked the idea for Bringg 36:39 – Bringg's rise: customers, unicorn valuation, and pulling the plug 38:35 – Secondary, investor philosophies, and closing the open loop 45:26 – Fairness for founders: why secondary isn't just smart, it's right 50:15 – Writing Confessions of a Unicorn Founder and what comes next 52:02 – The one piece of advice Ra'anan would give his younger self

    55 min
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About

Our mission is to bend the curve for Founders and CEOs. At Not Another CEO, we know there’s no formula for running a business. Leadership is forged through unique journeys, real challenges, and hard lessons. Our exclusive content showcases unfiltered stories and practical guidance from those who’ve crawled through the trenches. Our platform offers the largest library of CEO insights and how-to guides, sourced directly from a diverse community of leaders. Find our full video library, detailed playbooks, deep dives, and lessons learned on our Substack here ➡️ https://notanotherceo.substack.com/

Information

  • Creator
    Not Another CEO
  • Years Active
    2024 - 2026
  • Episodes
    103
  • Rating
    Explicit
  • Copyright
    © 2026 Not Another CEO
  • Show Website
    Not Another CEO Podcast

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