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 epis...
May 19, 2026•20 min•Ep. 100
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 sal...
May 12, 2026•1 hr 15 min•Ep. 99
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. I...
May 05, 2026•1 hr 9 min•Ep. 98
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 ...
Apr 28, 2026•28 min•Ep. 97
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, t...
Apr 21, 2026•1 hr 9 min•Ep. 96
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...
Apr 14, 2026•55 min•Ep. 95
What 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 rea...
Apr 07, 2026•42 min•Ep. 94
How 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...
Mar 31, 2026•14 min•Ep. 93
What 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, embr...
Mar 24, 2026•53 min•Ep. 92
What 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...
Mar 17, 2026•54 min•Ep. 91
What makes a startup truly successful in the eyes of venture capitalists? In this episode of Not Another CEO Podcast, host David Politis sits down with Rudina Seseri, Founder and Managing Partner at Glasswing Ventures, to dive into the realm of venture capital and discuss how startup founders can better position themselves for success. From her experience with early-stage companies to her unique perspective on the dynamics of venture capital, Rudina shares invaluable lessons about the importance...
Mar 10, 2026•46 min•Ep. 90
How do you choose an investor you’ll still trust when things inevitably get hard? In this episode, Ian Sigalow offers a candid, unfiltered look at early-stage investing and the founder–investor relationship, including one of the most sobering truths first-time founders often learn too late: it’s far harder to unwind a bad investor than a bad marriage. Drawing from decades of experience backing companies and founders at Greycroft, Ian breaks down how great investors actually think, decide, and en...
Mar 03, 2026•49 min•Ep. 89
How do you lead at scale when the role constantly asks you to stretch past what feels possible? In this episode, Irina Novoselsky shares the honest, vulnerable truth behind leading at the highest levels: the job isn’t about having every answer, it’s about choosing to step into roles, decisions, and moments that stretch you and reveal what you’re capable of. Irina brings deep experience from modernizing CareerBuilder and now leading Hootsuite, the world’s most widely used social media management ...
Feb 24, 2026•1 hr•Ep. 88
Can experience truly make a difference in the startup world? In this episode of Not Another CEO Podcast, David Politis speaks with Vanja Josifovski, Co-Founder and CEO of Kumo, to explore the journey of leading a cutting-edge AI enterprise. From his prestigious roles at Pinterest and Airbnb to founding Kumo, Vanja shares the lessons learned, the dilemmas faced, and the excitement of turning vast amounts of relational business data into actionable predictions. Takeaways: The Importance of Co-foun...
Feb 17, 2026•54 min•Ep. 87
How do founders navigate the intricacies of investor relationships to scale iconic companies? In this episode of Not Another CEO Podcast, David Politis speaks with Amish Jani, co-founder and partner at FirstMark Capital, about key considerations for both investors and founders in the venture ecosystem. Amish discusses his criteria for investment, the importance of understanding the 'why' behind a founder's journey, and the strategic approach to board meetings. He also sheds light on the dynamics...
Feb 10, 2026•45 min•Ep. 86
Can imposter syndrome drive you to succeed? In this solo episode of Not Another CEO Podcast, David explores his personal experiences with imposter syndrome and shares valuable insights gathered from countless conversations with leaders who have faced similar challenges. 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: http...
Feb 05, 2026•15 min•Ep. 85
Have you ever wondered how leaders manage to scale their organizations without being involved in every intricate detail? In this week’s episode, David Politis welcomes David Karandish, Founder and CEO of Capacity. Together, they delve into the art of building compound startups, scaling intricately interconnected businesses, and the profound role AI plays in today's market dynamics. Takeaways: The Compound Startup Strategy: David Karandish introduces the concept of a "compound startup," a term co...
Feb 03, 2026•49 min•Ep. 84
How do you know if a company is actually building momentum, or just looking polished on the surface? In this episode of Not Another CEO Podcast, David sits down with Jeff Morris Jr., Founder and General Partner at Chapter One, to break down what truly matters at the earliest stages of building a company. Jeff invests at pre-seed and seed, where ambiguity is high, data is limited, and speed of learning is often the only real signal. Before becoming an investor, Jeff was an early product leader at...
Jan 27, 2026•46 min•Ep. 83
How do you create a work culture that stands out and inspires team loyalty across multiple companies? In this episode, we gain valuable insights on this and more from the illustrious career of Donna Dubinsky. Known for her pivotal roles at Palm Computing and Handspring, Donna offers a rare long-term perspective on leadership, culture, and the technological landscape that has spanned decades. Takeaways: The Importance of Building a Strong Culture: Donna emphasizes that a great company starts with...
Jan 20, 2026•1 hr 10 min•Ep. 82
How do great founders use their best moments, not their hardest ones, to build the future of their company? In this episode, Jules Maltz shares the mindset that has guided him through decades of backing generational companies like Slack, Dropbox, Grammarly, MuleSoft, G2, and Buddy Media. For Jules, the brightest periods in a company’s journey are the moments to build aggressively: to hire exceptional executives, deepen product moats, and prepare for act two and act three long before the market f...
Jan 13, 2026•55 min•Ep. 81
How can you get the most out of your year-end? In this solo episode of Not Another CEO Podcast, David explores how leaders can leverage the end of the year for reflection, rallying their troops, and recharging for what lies ahead. 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/@NotAnotherCEOPodcas...
Dec 18, 2025•15 min•Ep. 80
How do you keep building when every month your company is almost out of money, and quitting would be the logical choice? In this episode, Artem Rodichev shares the gritty, unfiltered story of Ex Human’s near-death year. Instead of shutting the company down, that year hardened the team, shaped the culture, and created a level of resilience that became Ex Human’s defining advantage. Now Ex Human is profitable and building empathetic AI characters capable of multimodal emotional intelligence, techn...
Dec 16, 2025•1 hr•Ep. 79
How do you scale a company from zero to $100 million in 18 months without losing quality, clarity, or control? In this episode, Matt Price shares the remarkable story of building Crescendo, one of the fastest-growing companies ever featured on the show, by reimagining customer experience through advanced AI and deeply trained specialists. Matt’s journey has come full circle: from a technical support rep early in his career, to scaling Zendesk, to now creating an entirely new model for enterprise...
Dec 09, 2025•1 hr 1 min•Ep. 78
Have you ever wondered what it takes to build a company from your garage to a public entity? In this episode, Chieh Huang shares the raw, unfiltered story of building Boxed from a garage into a national e-commerce brand serving tens of millions of customers, and the emotional toll, unlikely breakthroughs, and market forces that shaped every chapter of the journey. He reflects on the lonely months of almost no orders, the overnight surge that changed everything, the pressure of becoming a public ...
Dec 02, 2025•1 hr 7 min•Ep. 77
When was the last time you paused long enough to thank the people who quietly helped you build? In this special compilation episode, we highlight moments from eleven CEOs who reflected on the investors that shaped their companies’ trajectories, not just through capital, but through conviction, guidance, and belief. These clips reveal how the right investors help founders stay grounded in their mission, navigate uncertainty, and make better decisions during pivotal moments of growth. Across these...
Nov 25, 2025•55 min•Ep. 76
How can you motivate your team to embrace AI in their daily work? In this solo episode of Not Another CEO Podcast, David discusses strategies to drive an AI-first mindset in your company. 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 Transistor: https://podcast.notanotherceo...
Nov 20, 2025•15 min•Ep. 75
How do you build one of the fastest-growing integration platforms in tech, while keeping culture, momentum, and innovation in sync? In this episode, Shensi Ding, Co-Founder and CEO of Merge, shares her journey from investment banking to leading one of the most successful integration infrastructure companies in the market. She opens up about the company’s evolution, from a small startup in San Francisco to a category leader powering technology products and AI agents for companies like Ramp and Op...
Nov 18, 2025•52 min•Ep. 74
How do the best founders learn faster, think deeper, and turn that mindset into companies that endure for decades? In this episode, host David Politis sits down with Nikhil Basu Trivedi, Co-Founder of Footwork, one of Silicon Valley’s most respected early-stage investors. Nikhil’s career spans both sides of the table, from co-founding Artsy, the groundbreaking online art platform, to investing in category-defining companies like Canva, Lattice, Frame.io, and The Farmer’s Dog. Nikhil shares how h...
Nov 11, 2025•39 min•Ep. 73
How do you build something meaningful without losing yourself in the process? In this episode, David talks with Betsy Fore, Co-Founder and former CEO of Tiny Organics and Founding Partner of Velveteen Ventures. Betsy shares her remarkable journey from toy inventor to serial entrepreneur and impact investor, becoming the first Native American woman to raise a Series A along the way. She opens up about co-creating Tiny Organics alongside 100 founding families, facing setbacks like her unaired Shar...
Nov 04, 2025•51 min•Ep. 72
How do you scale exceptional customer support without losing the human touch? In this episode, David sits down with Ryan Wang, Co-Founder and CEO of Assembled, to explore this very challenge. What started as a simple scheduling tool has evolved into an AI-powered customer support platform trusted by leading companies like DoorDash and Salesforce. Ryan opens up about the realities of scaling a fast-growing company, balancing innovation with culture, leading through learning, and keeping mission a...
Oct 28, 2025•56 min•Ep. 71
