Not Another CEO Podcast

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/

Not Another CEO Podcast is a business podcast hosted by Not Another CEO, with 112 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Not Another CEO hosts Not Another CEO Podcast, a business show with 112 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #111

  The Loneliness Every Leader Feels| Loneliness Compilation - Episode#111

  Aug 11, 202618 min

  Most founders assume the loneliness fades once the company succeeds. It doesn't. If anything, it gets quieter and harder to name. In this special compilation episode of Not Another CEO, David brings together lessons from nine founders, CEOs, and investors who have built, scaled, sold, and advised some of the most recognizable companies in tech. The conversation moves through why the seat is lonely in the first place, the false belief that you are the only one carrying it, and what the best CEOs actually build around themselves once they stop trying to carry it alone. Key Takeaways: Loneliness at the top isn't a personal failing, it's baked into the structure of the job: unpopular decisions, imperfect information, and a team that only ever sees half the picture. The belief that you are uniquely alone in your struggles is common and almost always wrong. Even the most people-first, culture-driven CEOs cannot fully escape the isolation of being the one who stays in the seat while everyone else eventually moves on. Founder loneliness is a default, not a fixed destiny. A co-founder, a coach, or a peer group can change the default entirely. The most effective support comes from someone with independent context on your business and your team. Support systems show up in real outcomes, not just in how someone feels. The founders who say they never felt the loneliness usually point to the same thing: a spouse, a family member, or a peer they could call and be fully honest with. Quote of the Episode "Your team has no conception of how lonely it is to be the CEO." — Adam Dell, Founder & CEO, Domain Money Guests Featured in This Episode: Marcus Ryu, Co-Founder & Former CEO, Guidewire — LinkedIn Adam Dell, Founder & CEO, Domain Money — LinkedIn Chieh Huang, Co-Founder & Former CEO, Boxed — LinkedIn Nick Mehta, Co-Founder & Former CEO, Gainsight — LinkedIn Nadia Boujarwah, Co-Founder & Former CEO, Dia&Co — LinkedIn Chip Hazard, General Partner & Co-Founder, Flybridge — LinkedIn Kathryn Minshew, Co-Founder & Former CEO, The Muse — LinkedIn Mike Grossman, CEO (6x) & Author, Failure Is an Option — LinkedIn Kyle Porter, Founder & Board Chair, Salesloft — LinkedIn Chapters: 00:00 – Trailer 00:48 – Intro 02:20 – Marcus Ryu 03:34 – Adam Dell 04:57 – Chieh Huang 05:59 – Nick Mehta 07:26 – Nadia Boujarwah 08:43 – Chip Hazard 10:10 – Kathryn Minshew 12:34 – Mike Grossman 15:38 – Kyle Porter 16:38 – Closing Thoughts

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  Episode #110

  Lessons From The Coach of Silicon Valley - Mike Grossman - EP#110

  Aug 4, 20261 hour

  Everything you think you know about why startups succeed might be wrong In this episode, Mike Grossman, six-time CEO and mentor to first-time founders across Silicon Valley, breaks down what thirty years of running companies actually taught him. From the $200 million counteroffer that blew up his first company, to why he believes luck accounts for 80 to 90 percent of every outcome, Mike pulls back the curtain on what nobody tells you before you take the job. If you think success is mostly about hard work and good decisions, this conversation will make you rethink how you handle risk, pivots, and your own sense of control. Key Takeaways: Build a System to Find the Truth: Your direct reports won't always tell you what's really happening, whether they're afraid to or simply don't know themselves. Cut through the management chain and find the people who will tell you the truth. Hold Your Plans Loosely: A plan is obsolete the moment you make it. The goal isn't a perfect plan, it's a planning mindset flexible enough to adjust without losing the team. Stop Whiplashing Your Team: What feels like velocity to a founder can feel like chaos to everyone else. Pivot too often and even your own board will stop trusting your judgment. Beware Your Own Kool-Aid: Believing your company is destined for outsized value can cost you the deal in front of you. Mike turned down a $40 million offer and countered at $200 million. He got neither. Luck Runs the Table: Mike believes 80 to 90 percent of a company's outcome comes down to luck, not execution. Focus on what you can control and let go of the rest. Watch Out for the Debilitating Win: Founders who succeed once often can't understand why the second company isn't working the same way. It usually wasn't the formula. It was luck. Nobody Talks About the Loneliness: Nearly every first-time CEO Mike coaches struggles with anxiety and isolation, and most feel they can't show it to their own investors. Quote of the Show: Plans are useless because whatever plan you make is immediately out of date and you have to make adjustments to it. But if you don't make any plan and you just do it on a seat of the pants basis, everything is kind of ad hoc, you end up jerking the company around and people get frustrated.- Mike Grossman, Entrepreneur and Author Connect with Mike: LinkedIn: https://www.linkedin.com/in/migrossman/ Book Failure is an Option: https://share.google/9DUEHB6596Eb1uXAa Chapters: 00:00 — Intro 02:21 — The One Thing Mike Would Do Again At Every Company 08:39 — Bill Campbell's Rule 20:13 — Plans Are Useless, Planning Is Indispensable 25:19 — The Pivot His Board Rejected 26:58 — All Of Them Struggle With Their Mental Health 30:47 — The $200 Million Deal He Blew Up 38:58 — Luck Accounts For 80 To 90 Percent 44:17 — The Debilitating Win 54:16 — Remembering The Coach Of Silicon Valley

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  Episode #109

  How to get your first 10 customers - July Pulse Episode - EP#109

  Jul 28, 202616 min

  "You cannot outsource acquiring those first ten customers. You can't do it." In this episode of Not Another CEO, David breaks down the six tactical ways he's used, three separate times now, to land his first customers from zero. From holding a pizza party for international students to handing out fliers at the Atlanta airport taxi stand to asking his own uncle to buy a phone system, David gets specific about what actually works when you're starting from nothing. What's covered: -Why getting your first customers is harder now than ever, even though building product has never been easier -Reconnecting with former employers and coworkers who already trust you -How to actually use your investor network, even at the angel stage -Why showing up in person at trade shows and meetups still beats almost everything else -Building in public on social media, even when almost nobody engages at first -The one BCC email that got David a customer and an important hire at the same time -How to do cold outreach that people actually respond to -Why none of these six tactics scale, and why that's exactly the point If you're a founder still chasing your first ten customers, this one's for you. We cover more topics like this in full playbooks on our Substack. Subscribe to get the tactical deep dives, not just the highlights: notanotherceo.substack.com Chapters: 00:00 - Trailer 00:44 - Why Finding Your First Customers Is Harder Than Ever 05:20 - Tactic 1: Reconnect with Former Employers & Coworkers 06:28 - Tactic 2: Tap Into Your Investor Network 08:14 - Tactic 3: Show Up in Person (Trade Shows & Meetups) 09:42 - Tactic 4: Build in Public on Social Media 11:02 - Tactic 5: Tell Your Friends and Family 12:02 - Tactic 6: Cold Outreach Done Right 13:53 - Why Doing Things That Don't Scale Is the Entire Point

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  Episode #108

  Backing Maniacs at Inception - What Investors Actually Look For | Jeff Becker - Antler - Episode#108

  Jul 21, 202655 min

  Everything you think you know about venture capital might be wrong. In this episode, Jeff Becker, General Partner at Antler New York, breaks down the brutal, hidden realities of the startup world. From why investors care more about your childhood psychology than your pitch deck, to why a $500 million exit can actually be a massive disappointment to a fund, Jeff pulls back the curtain on how venture capitalists actually math out risk. If you are operating with a broken mental model of how fundraising works, this conversation will completely reshape how you build, pitch, and scale your business. Key Takeaways: Pitch Yourself, Not the Product: Early-stage investors bet on the person first. Master your personal story of resilience before you even open your slide deck. Understand Fund Math: A $500 million exit does not return a large fund. You must build toward a multi-billion-dollar scale to make your investor's job a success. Expect the Volume Game: Firms like Antler build "engineered serendipity" by backing 200 early-stage founders at once, relying on massive diversification to find a breakout winner. Take Money Off the Table: Luck and market shifts rule the startup graveyard. When liquidity windows open, secure your personal financial safety. Storytellers Win the Cash: Being a great operator is not enough. You must be able to compress the gap between reality and future potential to get funded. Give Investors Specific Homework: Investors want to work for you, but vague asks get vague results. Give them transparent, direct tasks so they can help you win. Quote of the Show : "If I'm not working as hard as the founders, none of them are going to want me on their cap table." - Jeff Becker, General Partner, Antler Guest Featured in This Episode : Jeff Becker, General Partner, Antler (New York) LinkedIn: https://www.linkedin.com/in/jeffreylbecker/ Antler: https://www.antler.co/ We also break this episode down into a full write-up on Substack, with the exact playbook Scott used to fix the culture and rebuild the strategy from scratch, we're building out a full library of playbooks and lessons from every episode on Substack. Chapters 00:00 — Intro 02:00 — The Maniac Framework 09:00 — Why Childhood Matters 15:00 — Jeff's Origin Story 20:00 — Angel Investing Days 26:00 — The Role of Luck 33:00 — AI & One-Person Companies 41:00 — Fund Math & Dilution 46:00 — Storytellers vs. Operators 51:00 — "I Work For You"

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  Episode #107

  Backing the outsiders most VCs ignore | Nick Moran - New Stack Ventures - Episode#107

  Jul 14, 202649 min

  Majority founders only start thinking seriously about their next round when they’re already running low on cash. By then, you’re not really raising; you’re begging. On this week’s episode of Not Another CEO , we sit down with Nick Moran, Co-Founder and General Partner at New Stack Ventures. Founded in 2015, New Stack manages close to $100 million and leads pre-seed and seed rounds with a unique mission: backing "The Outsiders," who are ambitious founders building category-defining companies outside the Bay Area and outside the obvious networks. Nick also hosts Full Ratchet, one of the first venture capital podcasts ever made, now closing in on 1,000 episodes. I know how hard it is to stay consistent with a podcast. Doing it for over a decade is a different level. Nick shares his brutal honesty on what it actually takes to build a venture-backed business, why he tells founders to build their next pitch deck the day they close their current round, and how he evaluates the intangibles that traditional VCs completely miss. Key Takeaways: The Next Round Plan (NRP): Why fundraising is a continuous narrative, not a sporadic event. Nick breaks down how to align on business models, track leading indicators over lagging revenue, and build a highly targeted investor list early. Desire Beats Talent: Most VCs look for the "Peyton Mannings" of tech, meaning those who are obvious, expensive, and pedigreed. Nick hunts for the "Tom Bradys," founders with a chip on their shoulder, undeniable ambition, and the drive to beat long odds. Bad News Travels Fast: The ultimate trust-builder between a founder and a VC. Going dark creates anxiety; transparency during a brutal quarter is exactly what inspires an investor to throw you a lifeline. The Power of Being an "Outsider": Building in cities like Charlotte, Nashville, Dallas, or Chicago isn't a disadvantage. When the herd concentrates in the Bay Area, the best, most capital-efficient opportunities are often found where others aren't looking. Where the Smart Money is in AI: The shift from infrastructure to proprietary data. Nick explains why the next massive wave of AI value belongs to domain experts who control the data locked behind enterprise firewalls. Quote of the Show: “Do you want to be great or do you want to be happy?… You better be ready for the big game here because this is not an easy path. We're not going to be happy for the next ten years.” — Nick Moran Connect with Nick: LinkedIn: https://www.linkedin.com/in/nick-moran-a738503/ New Stack Ventures: https://www.newstack.com/ The Full Ratchet: https://www.youtube.com/@nicholasmoran3095/featured Chapters : 00:00 Trailer 01:30 Welcome Nick Moran, New Stack Ventures 03:54 Why desire is the ultimate founder trait 10:02 First impressions and the dating phase of investing 15:34 Founder-VC fit is like marriage 20:56 The Outsiders thesis and building a national network 27:48 Inside the Next Round Plan (NRP) 32:20 Communication, bad news should travel fast 39:00 What founders misunderstand about the VC side of the table 42:10 Where the smart money is moving in AI & Closing thoughts

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