Not Another CEO Podcast

Not Another CEO
  • 5.0 (15)
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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. He Lost Everything Twice…But Didn’t Stop Building - Rob LoCacsio - LivePerson - Episode #96

    11H AGO

    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
  2. 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
  3. Knew each other for 2 hours before We Co-Founded - Erica Jain - Healthie - Episode #94

    APR 7

    Knew each other for 2 hours before We Co-Founded - Erica Jain - Healthie - Episode #94

    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 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/ Chapters 00:00 – Intro: Healthie’s growth, impact & profitability 00:56 – The power of a true customer-first mindset 03:11 – How to build with customers from day one 06:00 – Hiring for values: the “3 R’s” framework 08:53 – Evolving culture as the company scales 12:54 – Operating systems & using OKRs effectively 16:50 – Why inefficiency kills companies (not ambition) 19:35 – Profitability, fundraising & staying in control 24:08 – Starting Healthie & getting first customers 30:30 – Biggest challenges: tech debt & rebuilding the product

    42 min
  4. March Pulse - The 5 Cs to Align Your Team - Episode #93

    MAR 31

    March Pulse - The 5 Cs to Align Your Team - Episode #93

    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 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 Politis 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.com/  #NotAnotherCEO #BusinessSuccess #MarchPulse Chapters: 00:00 Intro 00:48 Q2 Reprioritization Problem 02:36 Five Cs Framework 02:47 Concentrate Efforts 04:32 Communicate With Cadence 05:55 Outcome Driven Culture 06:44 Celebrate The Wins 08:13 Compensation Drives Behavior 11:26 Stay Focused For A Quarter 12:49 Outro

    14 min
  5. Pivoting to Financial Clarity - Didi Gurfinkel - Datarails - Episode #92

    MAR 24

    Pivoting to Financial Clarity - Didi Gurfinkel - Datarails - Episode #92

    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, 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 Gurfinkel Links: 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 Intro 01:21 Co-Founders Matter Most 02:28 Finding the Right Partners 05:47 Evolving Founder Roles 07:28 Five Tough Early Years 09:28 Building Tech Without Sales 13:08 Staying Motivated to Pivot 18:05 The Breakthrough Pivot 20:52 Why FP&A and Mid-Market 24:40 Scrappy Early Go-To-Market 26:38 LinkedIn Phone Number Hack 28:17 Knowing Product Market Fit 30:43 Removing Buying Friction 32:47 Zero to One Million ARR 35:26 AI and Finance OS Vision 41:38 Three Year Company Outlook 43:06 Founder Origin Story 46:25 Israel Startup Mindset 47:50 No Work Life Balance 51:02 Outro

    53 min
  6. Burned Bridges, No Retreats - Shaun Abrahamson - Third Sphere - Episode #91

    MAR 17

    Burned Bridges, No Retreats - Shaun Abrahamson - Third Sphere - Episode #91

    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 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 Abrahamson Links: 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 Intro 01:30 Burned Bridges Mindset 03:47 Early Bets And Bad Logos 06:20 YC Founder Signal Noise 08:48 Work Product Over Pitch 11:32 Climate Hardware Realities 15:39 Lego Building To Revenue 17:29 Tariffs And Supply Chain Chaos 20:02 Founders Forged By Turmoil 23:54 Why Third Sphere Went Climate 26:29 Mission Driven Founder Support 27:26 Belief And Reality Checks 30:41 Direct Feedback As A VC 35:35 Private Credit Replaces Banks 39:15 Founder Updates And Trust 44:29 Portfolio Math Harsh Truths 49:09 Biggest Missed Deal 50:46 Next Decade Climate Bets 53:16 Outro

    54 min
  7. Mastering Startup Execution - Rudina Seseri - Glasswing Ventures - Episode #90

    MAR 10

    Mastering Startup Execution - Rudina Seseri - Glasswing Ventures - Episode #90

    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 of execution, understanding investor expectations, and the intricacies of navigating the startup ecosystem. Takeaways:  The Value of Execution: For Rudina, the key trait she seeks in founders is execution excellence. It's not just about having a vision but demonstrating the ability and hustle to deliver beyond expectations.The Misunderstood VC Role: Many founders and employees don't understand the source of venture capital. Knowing that VCs manage funds from institutions like endowments and pensions changes the stakes and expectations.Importance of Strategic Partnerships: Rudina advises founders to seek investment from firms and partners that align with their stage and needs, rather than solely pursuing big names which might not provide necessary support.The Art of Quick Decision-Making: Efficiency in decision-making during early meetings can shape successful partnerships. Rudina values honesty in communicating why a VC might pass on an opportunity, emphasizing that a quick, thoughtful no is better than indecision.Sustained Support Post-Investment: At Glasswing Ventures, support continues beyond just funding, emphasizing talent acquisition, customer connections, and strategic guidance, ensuring startups grow sustainably. Quote of the Show: “What have we done for them lately to deserve to expect? Yes we’ve provided capital, but that’s not enough in my book." - Rudina Seseri Links: LinkedIn:https://www.linkedin.com/in/rudinaseseri/   Website: https://glasswing.vc/   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 Intro 01:37 Ruthless Execution 02:32 Spotting Hustle Fast 05:38 Execution in the AI Boom 07:55 Retention and Switching Costs 10:08 AI Interest vs Intent 13:19 AI Hype and Human Loop 17:58 How VCs Decide Quickly 20:39 Giving Fast Honest Nos 22:54 Execution and Go To Market Gaps 24:21 How VCs Support Founders 27:14 Portfolio Review Cadence 28:27 Why Take Board Seats 33:30 Term Sheets Beyond Valuation 38:17 Choosing Firm vs Partner 41:29 Scaling Support With Team 43:01 Why She Became an Investor 45:14 Outro

    46 min
  8. Trust is the Real Capital - Ian Sigalow - Greycroft- Episode #89

    MAR 3

    Trust is the Real Capital - Ian Sigalow - Greycroft- Episode #89

    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 engage behind the scenes. Ian shares what he looks for in exceptional founders, why the explosion of startups hasn’t increased the number of true breakout winners, and why most board meetings fail to create real value. This episode is a must-listen for any CEO navigating fundraising or building their first long-term investor relationships.   Takeaways:  Master of Two Domains: Sigalow emphasizes the importance of founders who excel in both product understanding and sales, calling them "masters of two domains" who are rare and invaluable.Big Market Potentials: Ian points out the essential need for startups to target significantly large markets. In the entrepreneurial world, having the potential to scale a company to a billion-dollar business is vital.The Earned Secret: A distinctive aspect investors look for is the "earned secret."The Importance of Trust in Investor Relationships: Sigalow stresses that founders should only take money from investors they trust, highlighting the lasting nature of these partnerships. Controlling the Board Meeting: Effective CEOs maintain control over board meetings, ensuring the focus remains on strategic issues rather than getting sidetracked.  Quote of the Show: “A CEO should never take money from someone they don’t trust. It’s harder to get out of a bad investor than a bad marriage." - Ian Sigalow Links: LinkedIn: https://www.linkedin.com/in/iansigalow/ Website: https://www.greycroft.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 Intro 01:32 Founder's Qualities and Market Potential 03:01 The Importance of Earned Secrets 03:57 Challenges in Identifying Exceptional Founders 06:12 The Evolution of Venture Capital 17:42 The Role of Technology in Venture Capital 21:45 Focus on Early-Stage AI Investments 26:40 Choosing the Right Investment Partner 10:50 Onboarding Process at Greycroft 27:50 The Rule of Three in Communication 29:24 Key Metrics for Founders 31:21 The Role of Board Meetings 38:26 Understanding Venture Capital Dynamics 18:46 Ian's Journey into Venture Capital 48:04 Outro

    49 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
    97
  • Rating
    Explicit
  • Copyright
    © 2026 Not Another CEO
  • Show Website
    Not Another CEO Podcast

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