Not Another CEO Podcast

Not Another CEO
  • 5.0 (18)
  • 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. 3d ago

    Why He Left a Decade at Forbes to Build Upstarts From Scratch - Alex Konrad - Upstarts - EP#116

    Most founders think the best story wins. Alex Konrad has spent 15 years watching what happens when the story is all there is. In this episode, Alex Konrad, Founder of Upstarts Media, joins me to share what he's learned from covering the biggest names in tech. He spent more than a decade at Forbes writing cover stories on people like Marc Benioff and the Collison brothers, ran the Midas List for ten years, and co-created the Cloud 100. In February 2025, he left to build Upstarts Media on his own. From the one trait he sees in the most successful founders to why great storytelling can make or break a company, Alex unpacks what he's learned from watching thousands of founders and investors up close. We also get into the loneliness of being a solo founder, the customer stories that stay with you, and what it takes to build a bootstrapped media company. If you're building a company, raising capital, or wondering whether you're built for the founder journey, this conversation will change how you think about obsession, storytelling, and what actually lasts. Key Takeaways: - The Obsession Is the Real Qualifier: The most successful founders Alex has interviewed aren't building for wealth or Twitter popularity. They're almost sick in the head about the work, and they couldn't live with themselves doing anything else. Alex explains why the founders chasing the lifestyle, the YC badge, or the title tend to burn out faster. - Find Your One Superpower: Early on, a founder should be able to do one thing better than anyone they could hire. For Alex, it's storytelling. For me, it turned out to be motivating people. - Storytelling Should Accelerate the Story, Not Be the Story: If you're a great salesperson selling magic beans, it catches up to you eventually. - What Great Investors Actually Do: After a decade on the Midas List, Alex says the number one thing CEOs want is an investor who feels like part of the team. - Great Founders Find Great Markets: Silicon Valley says a great founder can't fix a bad market. Alex isn't so sure. With how many companies pivot in the AI era, he believes a great founder will evolve into the market, or prove everyone wrong about how big it was. - Online Can Build a Brand or Eat Your Day: Alex recently wrote about CEOs and investors who are highly online to terminally online. We talk about the real advantage of a public brand, the risk of the doom scroll, and why he suggests putting your time on social media on the calendar. Quote of the Show: "Storytelling should accelerate your story, for good and bad. It shouldn't be the entire story." – Alex Konrad, Founder, Upstarts Media Guest Featured in This Episode: Alex Konrad, Founder, Upstarts Media LinkedIn: https://www.linkedin.com/in/alexrkonrad/ Upstarts Media: https://www.linkedin.com/company/upstarts-media/ We also break this episode down into a full write-up on Substack, where we turn every conversation into a practical playbook with the biggest lessons, frameworks, and strategies discussed in each episode. Chapters: 00:00 - Intro 02:01 - How Alex decides who to cover 11:37 - Why Alex left Forbes to build Upstarts 17:52 - The number one trait of successful founders 19:56 - Founder cycles and finding your one superpower 27:05 - The Midas List and what makes a great investor 34:35 - Storytelling and the trillion-dollar outcome 40:23 - Building Upstarts solo and bootstrapped 42:14 - The loneliness of being a solo founder 44:26 - Crazy customer stories and "Elon-level" security 49:16 - Terminally online founders 54:59 - Where Upstarts is in three years

    Why He Left a Decade at Forbes to Build Upstarts From Scratch - Alex Konrad - Upstarts - EP#116

  2. Sep 29

    He Blew Up His Own Winning Product Before AI Could - Eoin Hinchy - Tines - EP#115

    Eoin Hinchy spent 15 years living the exact problem he'd eventually build a company to solve. First at Deloitte, then eBay, then as Director of Information Security at DocuSign, he watched security teams burn hours gluing broken tools together by hand. So in 2018, he and his co-founder Thomas left to build the product they wished they'd had, out of a small office in Dublin. That company is Tines. Today it's 450 people across Dublin, Boston, San Francisco and Sydney, has raised over $270 million from Goldman Sachs, SoftBank, Accel and others, is valued at over a billion dollars, and is approaching $100 million in ARR. In this episode, we talk about the moment Tines decided to blow up its own winning product to get ahead of AI, why he's never built a pitch deck in his life, and the piece of advice he'd give himself before his very first job. Key Takeaways: Why founders beat sales teams from $60B companies: Eoin explains the difference between a missionary and a mercenary, and why buyers can feel it immediately. Refounding the company at its best quarter ever: The "falling off a building" analogy Eoin uses for why Tines rebuilt its core product around AI before the market forced their hand, and how he broke the news to his team and board. Why no customer was ever forced to migrate: The promise Eoin made to protect the people who got Tines to where it is today. Raising $270M without a single pitch deck: How Tines picked investors the way you'd pick a co-founder, and why Eoin never went looking for capital. "Nobody cares" : The reframe that Eoin says makes the hardest parts of the job easier, not harder. The Wizard of Oz moment: What happened the first time Eoin worked inside a company he used to think was run by geniuses. Quote of the Show: "The failures aren't going to be these dramatic explosions. They're going to be this kind of like quiet, unrequited effort where you put in all this hard work and like, everybody's kind of like, yeah, cool and moves on." — Eoin Hinchy, Co-Founder & CEO, Tines Guest Featured in This Episode: Eoin Hinchy, Co-Founder & CEO, Tines LinkedIn: https://www.linkedin.com/in/eoinhinchy/ Tines: https://www.tines.com/ We also break this episode down into a full write-up on Substack, where we turn every conversation into a practical playbook with the biggest lessons, frameworks, and strategies discussed in each episode. Chapters: 00:00:00 - Introduction 00:02:35 - Best Decision at Tines: Picking a Problem He Lived 00:06:26 - Why Founders Beat Sales Teams 00:11:18 - Spending 30–50% of His Week With Customers 00:12:58 - The Refounding Moment Begins 00:17:22 - The "Falling Off a Building" Analogy 00:21:13 - Telling the Team and the Board 00:24:38 - No Existing Customer Was Ever Forced to Migrate 00:33:13 - Bootstrapping and the First Raise 00:33:33 - Blossom Capital Shows Up at Their Office 00:36:33 - How He Actually Picked Investors 00:38:27 - Board as an Extension of the Team 00:41:27 - Building a Fully Remote, Global Team 00:43:18 - Biggest Challenge: "Nobody Cares" 00:55:48 - The Wizard of Oz Moment 00:58:38 - What Actually Drives Him 00:59:48 - Advice to His Younger Self

    He Blew Up His Own Winning Product Before AI Could - Eoin Hinchy - Tines - EP#115

  3. Sep 22

    How Paw Patrol saved Spin Master - Ronnen Harary - Spin Master - EP#114

    Most people think experience is your greatest advantage. Ronnen Harary believes it can become your biggest blind spot. In this episode, Ronnen Harary, Co-Founder of Spin Master, shares the lessons behind building one of the world's most successful toy and entertainment companies, the creator of global brands like Paw Patrol, Bakugan, Air Hogs, Rubik's Cube, and Etch A Sketch. From turning down a $100 million Hollywood deal he now regrets, to explaining why it's riskier not to bet on yourself, Ronnen unpacks the mindset that helped Spin Master grow from three friends with an idea into a multi-billion-dollar public company. Key Takeaways: 1. The Power of Not Knowing: Sometimes experience becomes a limitation. Ronnen explains why the lack of conventional wisdom helped Spin Master create products that industry veterans had already dismissed, and why trusting your instincts matters more than following what everyone else believes. 2. Bet on Yourself Early: Your 20s are a unique window to take meaningful risks. As responsibilities grow, so does the cost of leaving a stable career. Ronnen argues that waiting until you feel "ready" often means you never start at all. 3. Create Your Own Luck: Luck isn't something that happens to you. It's something you earn by staying in motion, building relationships, and consistently putting yourself in situations where unexpected opportunities can find you. 4. Trust Your Instincts: The same experience that helps you build a successful company can eventually cause you to overthink. Ronnen shares why he believes your intuition is often a better guide than your intellect when making the biggest decisions. 5. Build a Culture of Ideas: Some of Spin Master's best ideas came from meetings that everyone else wanted to cancel. Ronnen explains why protecting time for open discussion and pulling the right people into the room fuels creativity and better decision-making. Quote of the Show: "The power isn't in not knowing. It's in not letting your intellect override what you know internally." – Ronnen Harary, Co-Founder, Spin Master Guest Featured in This Episode: Ronnen Harary, Co-Founder, Spin Master LinkedIn: https://www.linkedin.com/in/ronnen-harary-99b13370/ Spin Master: https://www.spinmaster.com/en-US/ No Experience Necessary: https://www.penguinrandomhouse.com/books/789812/no-experience-necessary-by-ronnen-harary/ Chapters: 00:00:00 — Trailer & Introduction 00:02:05 — The 32-Year Tri-Founder Partnership 00:05:34 — "The Power of Not Knowing" & The Air Hogs Story 00:09:00 — The $100M Bakugan Regret 00:10:26 — Betting on Yourself in Your 20s & Inverse Risk 00:16:44 — Early Parent Support 00:18:47 — Becoming a "Grinder" 00:22:46 — Operational Discipline 00:27:14 — Making Your Own Luck: The Flick Tricks Story 00:33:40 — "Tethered Freedom" & Owning Your Culture 00:35:20 — Seeking Micro-Mentors & Writing "No Experience Required" 00:38:46 — The Decision to Take Spin Master Public 00:41:28 — The Origin Story of Paw Patrol 00:47:08 — Evolution of the Toy Industry 00:49:45 — Future Outlook for Spin Master 00:50:37 — Ronen’s Background 00:53:39 — Early Hustles 00:58:03 — Core Drive 00:59:13 — Workaholism, Burnout, and Health Sacrifices 01:04:03 — Advice to Younger Self

    How Paw Patrol saved Spin Master - Ronnen Harary - Spin Master - EP#114

  4. Sep 15

    The Provocative Statement That Built Knox - Irina Denisenko - Knox Systems - #EP113

    Most companies that start the FedRAMP process never finish it. Irina Denisenko built a business on getting you through it in 90 days, and said so, loudly, when everyone told her not to. Irina is the founder and CEO of Knox Systems, a company that gets software companies FedRAMP certified — the federal government's exhaustive cybersecurity authorization required to sell to agencies like the Pentagon — in 90 days instead of the usual multi-year process. Two years in, Knox has raised over $30 million, crossed 100 customers, and counts Adobe among them. Before this, Irina was COO of Class Technologies, where she had to get her own company FedRAMP certified and ended up acquiring an already, authorized company just to get through the process. She later spun that capability out as Knox. Here were my biggest takeaways: 1. Trust that you know your market better than the room does: When advisors pushed Irina to soften her tagline, she refused. "I know my market. I've lived this problem," she told me. 2. Turn a cost center into a revenue unlock: Irina assumed her first customers would come through CISOs. Instead, her first ten came from calling friends who ran companies. The real unlock was reframing FedRAMP: it's not a compliance expense, it's access to a market a company was previously shut out of entirely. 3. Make your investors work for you, even when you're not raising: Irina stays close to her investor network specifically because boardrooms are where FedRAMP tends to get dismissed as too slow to bother with. She's built a habit of asking investors to correct that in the room on her behalf. 4. Kill a bad bet before you defend it: Knox made an early bet on a specific AI approach to auto-remediate security vulnerabilities. The technology wasn't ready yet, and by the time that was undeniable, they'd already sunk real time and money into it. 5. Never underpay your best people: Irina calls her hiring approach "Delta Force" — senior only, nobody walking in without years of reps elsewhere. Her rule on comp: she's never once regretted overpaying for the right person, and calls the opposite mindset "pennywise, pound foolish." Quote of the Show: "If you know your market, you should know how to talk to them. And if you don't know your market, you go figure out your market first.” - Irina Denisenko, Founder & CEO, Knox Systems Guest Featured in this Episode: Irina Denisenko: https://www.linkedin.com/in/irinadenisenko/ Knox Systems: https://knoxsystems.com/ If you enjoy the episode, please like and subscribe on your favourite platforms and share with your network. We also break this episode down into a full write-up on Substack, with the exact playbook Irina used to build a go-to-market motion around a tagline everyone told her to drop, we're building out a full library of playbooks and lessons from every episode on Substack. Chapters: 00:00:00 — Intro: Irina Denisenko & Knox Systems 00:02:13 — The "FedRAMP in 90 Days" Tagline 00:06:34 — Building In-Person Across 3 Cities 00:08:52 — Hiring Only "Delta Force" Talent 00:11:41 — Revenue Per Employee in the Age of AI 00:17:10 — How She Vets a Delta Force Hire 00:25:57 — Never Regretting Overpaying for Talent 00:31:26 — Landing the First 10 Customers 00:42:41 — Investors as Her Best Referral Channel 00:47:43 — "Who Cares About This Market" 00:52:31 — The Valuation Hangover 01:02:16 — Scrapping a Year of AI Work 01:05:29 — From the Soviet Union to Founder 01:16:41 — Closing Advice: Integrity Above All

    The Provocative Statement That Built Knox - Irina Denisenko - Knox Systems - #EP113

  5. Sep 8

    Back to School Special with Sammy & Noah Politis #EP112

    I've interviewed over 100 founders and CEOs on Not Another CEO. I've asked them about their hardest days, their biggest regrets, and the sacrifices they made to build what they built. I never thought I'd be the one in that seat. This week, my own kids flipped the mic on me. Sammy and Noah wrote their own questions and interviewed me for the show, and I had no idea what was coming. We covered the worst week of my career, firing people I actually liked, the sacrifices I made that I'd still make again, and the moment my son stumped two successful CEOs on a live stage with a single question. Here's what we got into: Where it started: My father, their grandfather, built companies my whole life, and he put me on the BCC of every email he ever sent so I could learn the business before I had a job in it. My actual first paycheck came from a summer carrying furniture up four story walk ups for a moving company in New York. The worst week of my career: one week in 2019 where we lost our biggest customer, our incoming CRO backed out the day before he was supposed to start, I found out I wasn't winning an award I really wanted, I tore my Achilles, and I missed a family trip to Israel, all in the span of five days. Firing people I liked: I've fired hundreds of people over 20 years, including good friends. My kids asked how I could do that, and we talked about why it's actually the kinder move when it's done right. The sacrifice question: I missed my son's first steps building BetterCloud, and I left the hospital right after my younger son was born to go straight to a VC meeting. My kids wanted to know if I'd still make that call today. Comparing myself to other CEOs: yes, I still get jealous scrolling LinkedIn. It was worse when I was actually running BetterCloud and too deep in the weeds to see anything but my own world. How I define success: the same answer my son got out of me at our first ever live show, the one that stumped Kass and Mike Lazarow in front of a packed room. This is a different kind of episode for the show, and it might be one of my favorites. Thanks for listening, and thanks to Sammy and Noah for the toughest interview I've ever done. Quote of the Show: "The way that I define success is being able to meaningfully impact other people's lives while significantly benefiting your own life." — David Politis, Host, Not Another CEO Podcast Chapters: 00:00:00 - Trailer 00:02:22 - BetterCloud's Biggest Lesson 00:04:52 - What Inspired Me to Want to Be a CEO 00:07:12 - My First Job 00:10:14 - Pitching BetterCloud to My Own Kids 00:15:21 - What 100+ Interviews Taught Me About Building a Company 00:20:31 - AI and the Skills That Won't Get Replaced 00:23:37 - The Hardest Days 00:29:35 - Still Bad At It, Jealous of Other CEOs 00:33:13 - How I Define Success 00:41:29 - The Sacrifice Question 00:46:47 - Trust Your Gut

    Back to School Special with Sammy & Noah Politis #EP112

  6. Aug 11

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

    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 — LinkedInAdam Dell, Founder & CEO, Domain Money — LinkedInChieh Huang, Co-Founder & Former CEO, Boxed — LinkedInNick Mehta, Co-Founder & Former CEO, Gainsight — LinkedInNadia Boujarwah, Co-Founder & Former CEO, Dia&Co — LinkedInChip Hazard, General Partner & Co-Founder, Flybridge — LinkedInKathryn Minshew, Co-Founder & Former CEO, The Muse — LinkedInMike Grossman, CEO (6x) & Author, Failure Is an Option — LinkedInKyle Porter, Founder & Board Chair, Salesloft — LinkedIn Chapters: 00:00 – Trailer00:48 – 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

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

  7. Aug 4

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

    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

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

  8. Jul 28

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

    "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

    How to get your first 10 customers - July Pulse Episode - EP#109
See All (117)

Trailer

5
out of 5
18 Ratings

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
    117
  • Rating
    Explicit
  • Copyright
    © 2026 Not Another CEO
  • Show Website
    Not Another CEO Podcast

You Might Also Like