Not Another CEO Podcast

Not Another CEO
  • 5.0 (16)
  • Entrepreneurship
  • Updated Weekly

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. Why Fast-Growing Companies Slow Down | Dan O’Connell - Front - Episode#105

    2d ago

    Why Fast-Growing Companies Slow Down | Dan O’Connell - Front - Episode#105

    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 company, a founder, a high growth operator, and a hired CEO. Dan has done all four. Front is a customer operations platform used by more than 9,000 companies to manage customer conversations across support, customer success, account management, and sales. When Dan joined, the company had strong talent, a strong product, and strong customers. But growth had slowed. This episode is about what he did next and what he learned along the way. Takeaways: Focus reaccelerates growth: When Dan joined Front, his first move wasn't a product change or a new hire. It was getting brutally clear on who they serve, where they win, and explicitly what they were not going to do. That intentionality alone reaccelerated growth. Speed is a competitive advantage: Dan introduced speed as a formal company value at Front and it remains polarizing two and a half years later. It doesn't mean reckless. It means faster decision-making, strong opinionated leaders, and fighting friction when it shows up. Any decision is better than no decision. Taking over is harder than starting: You're inheriting history, culture, and legacy inertia and you can't take six months to build trust before making changes. You have to do both at the same time. As Dan puts it, you're flying the plane while rebuilding it. Great leaders stay close to customers: In his first week as CEO, Dan got on customer calls, visited every office, and jumped in the support queue to answer tickets. The same thing he now requires of every executive he hires. The team is always judging you and nothing builds credibility faster than showing you're willing to do the work. Platforms will outlast pure agents: After attending OpenAI's Frontiers Conference, Dan's contrarian take is that pure agent companies solving one workflow may get commoditized by OpenAI and Anthropic over time. His bet is on platforms and Front's position as the entry point for all customer conversations across channels, regardless of how the AI landscape evolves. If you are a founder, operator, or CEO this episode is worth your time. Quote of the Show: "Taking over has been much harder than I thought. And it's usually from the behaviors and people side." — Dan O'Connell, CEO, Front Links: LinkedIn: https://www.linkedin.com/in/danoconnell/ Front: https://front.com Chapters: 00:00 Trailer 01:15 Introduction 02:15 The One Thing That Had the Biggest Impact: Focus 05:00 Narrowing the ICP 07:30 The Operating Machinery That Keeps a Company Focused 13:00 Taking Over as a Non-Founder CEO 17:15 Flying the Plane While Rebuilding It 22:30 Platform vs. AI Agents 29:00 Building the Executive Team 42:00 The Biggest Challenge 47:30 Where Front Is in Three Years 49:00 Origin Story: From Southampton to Google to Founding TalkIQ 56:00 Two Career-Defining Moments & Advice to His Younger Self

    1h 1m
  2. The Best Deals Aren't the Hottest Deals | Dan Teran - Gutter Capital | Episode #104

    Jun 16

    The Best Deals Aren't the Hottest Deals | Dan Teran - Gutter Capital | Episode #104

    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 investor. We talk about the systems behind great culture, why the best founders are usually obsessed with a problem long before they start a company, what most VCs get wrong when evaluating startups, and how AI is changing the economics of company building. Dan is one of the most thoughtful operators and investors I've met, and this conversation is packed with practical lessons for founders at every stage. Takeaways: 1. Great cultures are built through systems, not slogans: The strongest company cultures don't come from posters on the wall. They come from who gets hired, who gets promoted, what behaviors get recognized, and what standards leaders reinforce every day. 2. The best founders are deeply connected to the problem they're solving: Dan believes the most resilient founders aren't chasing trends; they're solving problems they've experienced firsthand. That personal connection helps them stay committed when things get difficult. 3. Success is usually the result of hundreds of small decisions: Managed by Q wasn't built through one breakthrough moment. It was years of learning, adapting, fixing mistakes, and making better decisions over time. 4. AI is changing how companies get built: Founders can now test ideas, build products, and reach customers faster than ever before. What once took teams of engineers and millions of dollars can often be done by a handful of people. 5. Building something meaningful still requires hard work: Technology may change, but the reality of company building hasn't. Every successful founder eventually faces uncertainty, setbacks, and difficult decisions. Persistence is still the only way through them. Quote of the Show: ”If you're lucky enough to find a problem worth working on, that's where the fulfillment comes from.” - Dan Teran, Co-Founder & Managing Partner, Gutter Capital Links: LinkedIn: https://www.linkedin.com/in/danteran/ Website: https://www.gutter.cc/ Chapters: 00:00: Trailer 01:18: Meet Dan Teran: Founder, Operator, Investor 04:45: Building a Culture That Actually Scales 11:55: Why Every Employee Received Equity 18:15: The Story Behind the WeWork Acquisition 25:10: Life After Selling the Company 29:00: Starting Gutter Capital 39:00: How Dan Evaluates Founders 52:20: The Operating Blueprint for Startups

    56 min
  3. Your Pipeline Isn’t Broken, Your Strategy Is - Craig Rosenberg - Scale Venture Partners -Episode#103

    Jun 9

    Your Pipeline Isn’t Broken, Your Strategy Is - Craig Rosenberg - Scale Venture Partners -Episode#103

    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 pipeline, the power of ruthless micro-segmentation, why the old outbound “spam cannon” is dead, and what actually works right now including smart AI plays and unmistakably human experiences. If you’re a founder or leader frustrated with pipeline, this is the conversation you need. Takeaways: Your Pipeline Isn’t Broken Your Strategy Is: Most companies are going too broad instead of micro-segmenting their ICP on the other hand the winners are ruthlessly micro-segmenting their ICP around homogeneous use cases.Micro-Segmentation Is the New Superpower: Stop fearing you’ll miss pipeline by going narrow. Focus the entire GTM team on a tight subset of accounts with similar needs this unlocks consistent messaging, better win rates, and faster learning cycles.Talk to 10 People a Week in Your ICP: Whether you’re at seed or scaling, executives must get in the weeds. Have real conversations, pitch them, and ask for next steps. Gong calls and outsourced interviews aren’t enough. This is how you validate and refine your story fast.Use AI as a Multiplier, Not a Crutch: Leverage AI for custom market reports, personalised demos at scale, deep account research, and proprietary signals. But the real advantage comes from pairing AI with unmistakably human interactions in a market flooded with AI noise.High-Touch Human Experiences Are Back: Curated dinners, thoughtful direct mail, and once-in-a-lifetime events (like World Cup experiences) outperform digital spam. Buyers can feel when real care and intention went into the interaction. Quote of the Show: ”Because now AI is about to flood the market, is what are those unmistakably human interactions you can have.” - Craig Rosenberg, Chief Platform Office, Scale Venture Partners Links: LinkedIn: https://www.linkedin.com/in/craigrosenberg/ Scale Venture Partners: https://www.scalevp.com/team/craig-rosenberg Chapters: 00:00: Intro 02:45: Why Pipeline Feels Harder Than Ever 06:10: The Power of Ruthless ICP Micro-Segmentation 10:25: Special Forces Teams for New Market Expansion 14:40: What’s Changed in B2B Buying (2026 Reality) 19:15: Why the Old Outbound Playbook Is Dead 24:50: AI Tactics That Are Actually Working 29:40: The Unmistakably Human Differentiator 35:20: High-Impact Events & Experiences 42:15: Final Advice + How to Stay Ahead

    50 min
  4. Better to Be Fast than to be Right - Jessica Lin - Work-Bench - Episode #102

    Jun 2

    Better to Be Fast than to be Right - Jessica Lin - Work-Bench - Episode #102

    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 minutes, why product-market fit has become harder than ever, and what most startups misunderstand about growth, fundraising, and becoming truly mission critical. The conversation also explores the emotional side of venture capital, imposter syndrome, building a venture firm, and the realities founders face between Seed and Series A. From founder obsession and investor psychology to career risk and company building, this episode is a candid look into how elite investors think and what founders need to understand to build enduring companies. Takeaways:Investors Often Decide Faster Than Founders Realise: Jess explains that initial conviction about a founder is usually formed within minutes. The rest of the process is often about validating or disproving that instinct.Growth Alone Is No Longer Enough: Fast revenue growth has become table stakes. The real question investors ask now is: Would customers genuinely care if this product disappeared tomorrow?Founder Obsession Matters: The best founders are deeply obsessed with the problem they’re solving. They see something others don’t and cannot stop thinking about it.Venture Capital Is Emotionally Uncertain: Jess shares how difficult it is to know whether you’re actually “good” at investing because feedback loops in venture can take 10+ years.Building a VC Firm Is Like Building a Startup: From branding and hiring to differentiation and operations, venture firms face many of the same challenges founders do when building companies.Quote of the Show:It's better to be fast than to be right. Because if you're fast, if you just have more at bats, you will least be able to course correct. - Jessica Lin, Co-Founder & General Partner at Work-Bench. Links: LinkedIn: https://www.linkedin.com/in/jessicalin8 Work-Bench: https://www.work-bench.com/ Chapters:00:00: Trailer 04:12: How investors evaluate founders in the first five minutes 09:35: The founder traits that create investor conviction 15:08: Why Series A has become much harder 20:44: What “mission critical” really means in startups 27:10: Product-market fit vs fast growth 33:26: Imposter syndrome in venture capital 39:41: Career advice, risk & serendipity 46:03: Why building a VC firm feels like building a startup 53:18: Final lessons for founders and investors

    1h 4m
  5. The Seven Deadly Sins of Founders - Michael Loeb - Loeb.Nyc - Episode #101

    May 26

    The Seven Deadly Sins of Founders - Michael Loeb - Loeb.Nyc - Episode #101

    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-earned lessons from 35 years of building: the character flaws that destroy founders before the market ever gets the chance, what separates real entrepreneurial DNA from people who just like the idea of it, why sociopaths concentrate in startups, and why the entrepreneurial class should be funding itself instead of depending on traditional venture capital. Takeaways: 1. The character flaws that kill founders are predictable: Michael maps pride, sloth, delusion, and the refusal to listen onto real founder failure stories. 2. Entrepreneurship is innate, not learned: Real founders show up early the lemonade stand, the paper route, the video game rental business in college. 3. Surrender being an option is a dealbreaker: The moment a founder puts quitting on the table, Michael says the relationship is over. 4. Charm is a feature and a warning sign: Sociopaths concentrate in startups because magnetic charm and the ability to make fiction feel real are exactly the qualities that attract early capital. 5. The entrepreneurial class is rich enough to fund itself: Michael's Uncharted model is built on a simple premise: founders who have had exits, understand the journey, and can write a $10,000 check should be backing each other not waiting on institutional capital that is fundamentally optimising for something different. Quote of the Show: "When anybody uses those words I'm just going to give up if that is an option, you have no choice. Surrender is not an option. Quitting is not an option. So as soon as that goes on the table, they're done." - Michael Loeb, Founder & CEO, Loeb Enterprises Links: LinkedIn: https://www.linkedin.com/in/michaelloeb1/ Website: https://loeb.nyc/ 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 - Trailer 03:45 - The seven deadly sins of founders and the pride that bankrupted a $100M business 06:36 - Sloth, the founder who quit, and why surrender can never be an option 13:35 - How Michael spots real entrepreneurial DNA before writing a check 15:43 - The video game rental kid and what genuine founder instinct looks like in college 20:00 - Envy and why rent-a-CEOs create a different kind of danger 22:00 - The thin line between necessary optimism and dangerous delusion 24:53 - Why charm is both a feature and a warning sign 26:16 - The founder who refuses to listen 31:19 - Why being numeric is a non-negotiable founder requirement 34:58 - Founders Backing Founders

    1h 15m
  6. Why CEO's Do It Anyway: Lessons I Learned Talking To 100 Founders - NAC - Episode #100

    May 19

    Why CEO's Do It Anyway: Lessons I Learned Talking To 100 Founders - NAC - Episode #100

    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 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 - Introduction 02:10 - 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

    20 min
  7. How it was game over for Guidewire until it wasn’t - Marcus Ryu - Guidewire - Episode #99

    May 12

    How it was game over for Guidewire until it wasn’t - Marcus Ryu - Guidewire - Episode #99

    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 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, Guidewire Chapters:00:00 - Trailer 02:10 - The importance of strategic coherence in company building 08:45 - Why startups need an enemy and a clear sense of differentiation 15:20 - Discovering the broken insurance software market 27:20 - Learning sales as a founder CEO 31:00 - Getting the first customers & surviving long enterprise sales cycles 36:20 - Building Guidewire with extreme capital efficiency 43:10 - The pressure modern founders feel to grow at impossible speeds 49:40 - Surviving lawsuits and competitive attacks from incumbents 58:00 - Transitioning from founder CEO to investor at Battery Ventures 01:06:30 - Marcus’s biggest personal reflection after two decades as CEO

    1h 15m
  8. From Sticky Notes on My Door to $1.5B Logistics Disruptor - Itamar Zur - Veho - Episode #98

    May 5

    From Sticky Notes on My Door to $1.5B Logistics Disruptor - Itamar Zur - Veho - Episode #98

    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. 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, Veho Links: 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

    1h 9m
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5
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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
    106
  • Rating
    Explicit
  • Copyright
    © 2026 Not Another CEO
  • Show Website
    Not Another CEO Podcast

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