Not Another CEO Podcast

Most founders know they need an Ideal Customer Profile. Fewer realize how much growth depends on getting it right. In this special compilation episode of Not Another CEO, David brings together lessons from seven founders, CEOs, and investors who all reached the same conclusion: growth accelerates when you're crystal clear about who you serve. The episode explores why broad ICPs slow companies down...

Most people assume starting a company is the hardest job in business. Dan O'Connell has learned that taking over one can be even harder. Dan's career has taken him from Google, where he joined when the company was 300 people, to founding TalkIQ before AI was cool, to helping scale Dialpad past $200M in revenue, and now to leading Front as CEO. Not many people have been an executive at a big tech c...

Most founders talk about building a company but very few talk about what it actually costs. Dan Teran knows both sides of that story. In this episode, Dan shares how he built Managed by Q from the ground up, scaled a team that included nearly 1,000 frontline workers, gave equity to cleaners and handymen, navigated an acquisition by WeWork, and ultimately made the transition from founder to investo...

Why does your pipeline feel broken… when the real problem is your strategy? In this episode, I sat down with my longtime mentor & friend Craig Rosenberg, Chief Platform Officer at Scale Venture Partners. Craig taught me how to build inside sales teams 20 years ago, and he’s still one of the sharpest minds in go-to-market strategy. We break down why most companies are struggling to create pipel...

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 minu...

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...

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...

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-earn...

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 tho...

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...

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 conv...

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...

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...

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:  Con...

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 ea...

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 unfo...

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 p...

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 com...

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 modern...

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...

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...

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   Ap...

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:  T...

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 lear...

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.  Tak...