Not Another CEO Podcast

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 PartnersLinks:LinkedIn: https://www.linkedin.com/in/craigrosenberg/ Scale Venture Partners: https://www.scalevp.com/team/craig-rosenbergChapters:00:00: Intro02:45: Why Pipeline Feels Harder Than Ever06:10: The Power of Ruthless ICP Micro-Segmentation10:25: Special Forces Teams for New Market Expansion14:40: What’s Changed in B2B Buying (2026 Reality)19:15: Why the Old Outbound Playbook Is Dead24:50: AI Tactics That Are Actually Working29:40: The Unmistakably Human Differentiator35:20: High-Impact Events & Experiences42:15: Final Advice + How to Stay Ahead

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/jessicalin8Work-Bench: https://www.work-bench.com/Chapters:00:00: Trailer04:12: How investors evaluate founders in the first five minutes09:35: The founder traits that create investor conviction15:08: Why Series A has become much harder20:44: What “mission critical” really means in startups27:10: Product-market fit vs fast growth33:26: Imposter syndrome in venture capital39:41: Career advice, risk & serendipity46:03: Why building a VC firm feels like building a startup53:18: Final lessons for founders and investors

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 EnterprisesLinks: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/1NQ9oAB2XKlgWeL8iEQXg0Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707YouTube: https://www.youtube.com/@NotAnotherCEOPodcastChapters:00:00 - Trailer03:45 - The seven deadly sins of founders and the pride that bankrupted a $100M business06:36 - Sloth, the founder who quit, and why surrender can never be an option13:35 - How Michael spots real entrepreneurial DNA before writing a check15:43 - The video game rental kid and what genuine founder instinct looks like in college20:00 - Envy and why rent-a-CEOs create a different kind of danger22:00 - The thin line between necessary optimism and dangerous delusion24:53 - Why charm is both a feature and a warning sign26:16 - The founder who refuses to listen31:19 - Why being numeric is a non-negotiable founder requirement34:58 - Founders Backing Founders

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 - Introduction02:10 - 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

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, GuidewireChapters:00:00 - Trailer02:10 - The importance of strategic coherence in company building08:45 - Why startups need an enemy and a clear sense of differentiation15:20 - Discovering the broken insurance software market27:20 - Learning sales as a founder CEO31:00 - Getting the first customers & surviving long enterprise sales cycles36:20 - Building Guidewire with extreme capital efficiency43:10 - The pressure modern founders feel to grow at impossible speeds49:40 - Surviving lawsuits and competitive attacks from incumbents58:00 - Transitioning from founder CEO to investor at Battery Ventures01:06:30 - Marcus’s biggest personal reflection after two decades as CEO