Podcast
Not Another CEO Podcast
Hosted by Not Another CEO · EN
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/
22episodes
Episodes
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Why CEO's Do It Anyway: Lessons I Learned Talking To 100 Founders - NAC - Episode #100
2w ago00:20:06Tap to summarize100 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 - Introduction02:10 - 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
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How it was game over for Guidewire until it wasn’t - Marcus Ryu - Guidewire - Episode #99
3w ago01:14:36Tap to summarizeBuilding 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, GuidewireChapters:00:00 - Trailer02:10 - The importance of strategic coherence in company building08:45 - Why startups need an enemy and a clear sense of differentiation15:20 - Discovering the broken insurance software market27:20 - Learning sales as a founder CEO31:00 - Getting the first customers & surviving long enterprise sales cycles36:20 - Building Guidewire with extreme capital efficiency43:10 - The pressure modern founders feel to grow at impossible speeds49:40 - Surviving lawsuits and competitive attacks from incumbents58:00 - Transitioning from founder CEO to investor at Battery Ventures01:06:30 - Marcus’s biggest personal reflection after two decades as CEO
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From Sticky Notes on My Door to $1.5B Logistics Disruptor - Itamar Zur - Veho - Episode #98
May 501:09:02Tap to summarizeHe 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, VehoLinks: 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
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The 10 Step Hiring Framework - April Pulse - Episode #97
Apr 2800:28:08Tap to summarizeDescription: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 CEOChapters00:00 – Why hiring is the highest-leverage decision you make06:14 – “The right people” vs. just people08:30 – The hidden cost of bad hiring decisions11:00 – Why most companies are winging interviews13:30 – The importance of preparation and alignment16:00 – The power of taking decision-grade notes18:30 – Step 1–3: Setting the tone, story, and “why” questions21:00 – Going deep: testing real experience and competence25:00 – Finding what energizes candidates29:00 – Anti-selling the role + spotting red flags in questions
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He Lost Everything Twice…But Didn’t Stop Building - Rob LoCacsio - LivePerson - Episode #96
Apr 2101:08:48Tap to summarizeWhat 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 LoCascioLinks:- 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 – Intro01:19 – From nothing: $5K, a couch, and starting over02:10 – Building LivePerson and going public05:30 – The COVID surge: $900M to $4B in 12 months09:45 – When things started to break14:20 – Losing control of the company he built18:05 – The hardest fight of his career22:40 – Watching the company decline after leaving27:15 – The emotional toll of losing everything31:50 – Identity beyond the company36:10 – Why founders can always build again41:25 – Creativity as the ultimate unfair advantage46:00 – What Rob is building next50:30 – The real meaning of success and failure
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Not Taking Money Off the Table Can Cost You Everything - Ra’anan Cohen - Bringg & MobileMax (#95)
Apr 1400:55:20Tap to summarizeWhat 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-asshole 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 & BringgLinks:Book: Confessions of a Unicorn Founder - available on AmazonLinkedIn: https://www.linkedin.com/in/raananc/Website: www.raanancohen.comChapters:00:00 – Intro: From IPO to zero to unicorn Ra'anan's full arc01:22 – The one thing that had the biggest impact: team building06:00 – The no-asshole policy and how to hire for attitude08:50 – Framing hard weeks as progress the "great week" mantra13:48 – MobileMax: the IPO, the $10M phone call, and saying no16:32 – Why Ra'anan didn't sell a single stock and what it cost him18:54 – When the iPhone reshaped mobile and MobileMax spiraled25:05 – Broke and "the guy who made it" faking it at startup meetups32:14 – The personal cost: family, presence, and the founder's obsession34:13 – How a late pizza sparked the idea for Bringg36:39 – Bringg's rise: customers, unicorn valuation, and pulling the plug38:35 – Secondary, investor philosophies, and closing the open loop45:26 – Fairness for founders: why secondary isn't just smart, it's right50:15 – Writing Confessions of a Unicorn Founder and what comes next52:02 – The one piece of advice Ra'anan would give his younger self
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Knew each other for 2 hours before We Co-Founded - Erica Jain - Healthie - Episode #94
Apr 700:42:06Tap to summarizeWhat if the reason your company isn’t growing… is because you’re spending too much time inside the company instead of with your customers?Erica Jain, Co-Founder & CEO of Healthie, breaks down how a relentless customer-first mindset shaped every part of the business from product decisions to hiring to long-term strategy.In this conversation, she shares how they got their first customers with no sales experience, why internal inefficiency is a bigger risk than doing too much, and what it really takes to maintain speed as a company scales. She also dives into rebuilding the product after early success, hiring for values, and staying in control while growing a profitable company.If you want to build faster, stay close to your customers, and avoid the trap of internal complexity slowing you down this episode is for you.Takeaways:Obsess Over Customers as Your True North Star: The single most important thing is to instill a true customer-first mindset across the entire company. Customers literally “keep our lights on” every decision, roadmap, and internal process should revolve around delivering an incredible experience for them.Simplify Your Values Ruthlessly: Erica and her team reduced their values from eight which nobody could remember to just the Three R’s: Respect, Resilience, and Reliability. Hire for values far more than skills, especially as technology changes rapidly.Profitability Equals Control: They chose to remain profitable for most of the company’s life to always stay in control of their destiny. Build a generational business and raise capital only when it serves clear long-term goals, never out of desperation.Mediocrity Is the Real Killer: Companies don’t usually die from doing too many things they die from descending into mediocrity caused by slow internal processes, too many meetings, and inefficient decision-making. Speed and execution velocity matter enormously.Hiring, Team Building, and Scaling Challenges: Hiring for values, the difficulty of identifying customer-first people in interviews, retaining talent (many team members 5–7+ years), going through a major codebase rewrite, and the constant battle against internal inefficiency as the company grows.Quote of the Show:The one thing I would do is instill… a true customer first mindset. There is something incredibly, incredibly powerful about waking up every single minute of every single day and wholeheartedly focusing on making sure our customers are taken care of.”- Erica Jane, CEO & Co-Founder of Healthie.Links:LinkedIn: https://www.linkedin.com/in/ericajain/Website: https://www.gethealthie.com/Chapters00:00 – Intro: Healthie’s growth, impact & profitability00:56 – The power of a true customer-first mindset03:11 – How to build with customers from day one06:00 – Hiring for values: the “3 R’s” framework08:53 – Evolving culture as the company scales12:54 – Operating systems & using OKRs effectively16:50 – Why inefficiency kills companies (not ambition)19:35 – Profitability, fundraising & staying in control24:08 – Starting Healthie & getting first customers30:30 – Biggest challenges: tech debt & rebuilding the product
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March Pulse - The 5 Cs to Align Your Team - Episode #93
Mar 3100:13:45Tap to summarizeHow can one simple strategy drive your company’s success? In this solo episode of Not Another CEO Podcast, host David Politis dives deep into the significance of alignment and prioritization within a company. Reflecting on a personal article shared via Substack, David emphasizes the importance of refocusing and reprioritizing company goals as new challenges and opportunities arise.Takeaways: Concentration of Efforts: Narrowing down the focus to one primary goal can unify and effectively drive a company's momentum. By concentrating efforts, every team member can contribute to company growth.Effective Communication: Regular and focused communication is key to keeping everyone aligned with the company's goals. David suggests updating the team weekly to maintain a cadence that ensures urgency and focus.Culture of Outcome-Based Work: Create a work culture that rewards achievements based on outcomes rather than just effort. It’s crucial for employees to understand their work's impact on the company's success.Celebration of Successes: Recognizing and celebrating achievements fosters a positive work environment and encourages further productivity. Celebrations can be as simple as an email recognition or a shoutout during all-hands meetings.Strategic Compensation: Implementing flexible compensation structures isn't limited to sales teams. Properly aligning compensation with company goals can motivate teams across the board to go above and beyond.Removing Distractions: Encourage leadership to stay concentrated on key goals by avoiding changes in priorities throughout the quarter. Written notes can capture evolving ideas, which can then be revisited during the next planning phase.Leadership Involvement: Leaders should actively remove barriers for their teams rather than changing priorities. This approach helps maintain focus and supports execution on high-priority initiatives.Quote of the Show:“The less you communicate about the other things, and the more you just make all the communication about that thing, people are gonna understand this is what we're focusing on." - David PolitisWays 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 Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #MarchPulseChapters:00:00 Intro00:48 Q2 Reprioritization Problem02:36 Five Cs Framework02:47 Concentrate Efforts04:32 Communicate With Cadence05:55 Outcome Driven Culture06:44 Celebrate The Wins08:13 Compensation Drives Behavior11:26 Stay Focused For A Quarter12:49 Outro
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Pivoting to Financial Clarity - Didi Gurfinkel - Datarails - Episode #92
Mar 2400:52:49Tap to summarizeWhat does it take to transform a struggling startup into a booming enterprise? In this episode of Not Another CEO Podcast, host David Politis sits down with Didi Gurfinkel, Co-Founder and CEO of Datarails. Together, they delve into Didi's decade-long journey of building a successful financial platform from scratch, discussing both the struggles and triumphs of his entrepreneurial path.From his early days at Cisco to co-founding Datarails, Didi shares invaluable lessons on startup pivoting, embracing new technologies, and harnessing AI to revolutionize financial operations.Takeaways: The Power of the Right Team: Didi highlights the importance of having the right co-founders. He credits the success of Datarails largely to the strong foundational team that shared common goals and complementary skills.Embracing the Brutal Truth: Didi emphasizes the need for leaders to be honest about their failures and to learn from them while maintaining a visionary outlook for the future.Importance of Having a Name: Drawing from past experiences, Didi advises startups to choose a product that has a recognisable name and existing budget line.Finding Your Ideal Market Fit: Datarails achieved success by narrowing their focus to finance professionals who love Excel, aligning product benefits with users’ existing skills and preferences.Strategic Use of AI: Datarails seeks to prepare organizations for AI integration, ensuring readiness for technological advancements.Balancing Work and Family: Didi points out that while entrepreneurship is all-consuming, showcasing the possibility of building something significant can offer invaluable lessons for family.Quote of the Show:“If someone ask me, I'm not sure if I have the product market fit, I'm saying, no, you don't have it. If you had it, you know." - Didi GurfinkelLinks:LinkedIn:https://www.linkedin.com/in/didigurfinkel/ Website: https://www.datarails.com/ 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 Intro01:21 Co-Founders Matter Most02:28 Finding the Right Partners05:47 Evolving Founder Roles07:28 Five Tough Early Years09:28 Building Tech Without Sales13:08 Staying Motivated to Pivot18:05 The Breakthrough Pivot20:52 Why FP&A and Mid-Market24:40 Scrappy Early Go-To-Market26:38 LinkedIn Phone Number Hack28:17 Knowing Product Market Fit30:43 Removing Buying Friction32:47 Zero to One Million ARR35:26 AI and Finance OS Vision41:38 Three Year Company Outlook43:06 Founder Origin Story46:25 Israel Startup Mindset47:50 No Work Life Balance51:02 Outro
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Burned Bridges, No Retreats - Shaun Abrahamson - Third Sphere - Episode #91
Mar 1700:54:25Tap to summarizeWhat sets apart the founders who persevere through immense challenges and come out stronger on the other side? In this episode, David sits down with Shaun Abrahamson, Co-Founder & Managing Partner at Third Sphere. Shaun shares his unique insights into the high-stakes world of venture investing, particularly in climate tech and hardware, reflecting on the kinds of founders he backs and the unforeseen hurdles they've had to overcome.Shaun delves into his philosophy on investing in early-stage companies, emphasizing the importance of resilience and adaptability in founders. He also discusses the intricacies of climate tech investment and the lessons he's learned from over two decades in the field. Takeaways:The Importance of "Burned Bridges": Shaun explains that he looks for founders who feel they have no option but to succeed, drawing a comparison to immigrants or those without a fallback, which can drive relentless focus and fortitude.Signals of Early-Stage Investment: Investing at the pre-seed stage involves identifying teams with potential through their work product rather than initial conversations. Challenges of Climate Tech Investing: The difficulty in obtaining clear customer signals within climate tech is highlighted. Shaun notes that genuine customer commitment is hard to gauge and is essential for moving beyond pilot projects.Weathering the Storms: Shaun emphasizes that founders who persist through geopolitical challenges, like supply chain disruptions and tariffs, emerge uniquely stronger. Quote of the Show:“Portfolio math is brutal because it basically says that most companies don’t matter… it’s very easy to say, it’s very hard for founders to accept they may not be that one or two companies." - Shaun AbrahamsonLinks:LinkedIn: https://www.linkedin.com/in/shaunabe/ Website: https://thirdsphere.com/ 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 Intro01:30 Burned Bridges Mindset03:47 Early Bets And Bad Logos06:20 YC Founder Signal Noise08:48 Work Product Over Pitch11:32 Climate Hardware Realities15:39 Lego Building To Revenue17:29 Tariffs And Supply Chain Chaos20:02 Founders Forged By Turmoil23:54 Why Third Sphere Went Climate26:29 Mission Driven Founder Support27:26 Belief And Reality Checks30:41 Direct Feedback As A VC35:35 Private Credit Replaces Banks39:15 Founder Updates And Trust44:29 Portfolio Math Harsh Truths49:09 Biggest Missed Deal50:46 Next Decade Climate Bets53:16 Outro
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