Not Another CEO Podcast

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 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

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-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

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/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

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 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

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 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