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CEO’s Unscripted

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by Jane Gentry

5.0(4 reviews)

36 episodes

Updated Daily

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Podcast Overview

Real Talk. Real Growth. Real Results in the Mid-Market Jane Gentry consulted in enterprise for 20 years. And, after being a CEO in a mid-sized company, she realized why they say it is loneliest at the top. Mid-market CEOs learn their craft through trial and error or by reaching outside their organization for help. She launched CEOs Unscripted as a bi-weekly podcast by mid-market CEOs for mid-market CEOs. Our purpose is to provide insight into the unscripted, unfiltered journeys of CEOs and Founders as they talk about their wins, losses, lessons and playbooks for growing and scaling their organizations. There is no better forum than learning from your peers.

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3/18/2025

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Recent Episodes

July 28, 2026

He Sold Company After Company — This Is What He'd Tell You

Most business owners wait until they're tired to think about selling. By then, it's too late — and it costs them millions. In this episode of CEOs Unscripted, host Jane Gentry sits down with Ryan Frederick, principal of Transform Labs — a serial entrepreneur who has started and sold company after company, and whose latest venture was just acquired (fresh off the deal). Ryan and Jane pull back the curtain on what buyers actually want, why a full calendar is a red flag, and the uncomfortable truth about being the bottleneck in your own business. If you're a mid-market CEO who ever plans to sell — or just wants to build a business that could run without you — this is the conversation to hear. 🔑 WHAT YOU'LL LEARN: ✅ Why you should plan your exit the day you open the doors — not the day you're tired ✅ The "full calendar" trap: how being busy signals you're the bottleneck ✅ Why you can't sell a business you're still working IN ✅ How to get honest feedback (and why your team will never give it to you) ✅ The "mock transaction" test to see if your business is truly sellable ✅ How to prep your people and leadership for a successful integration ✅ Why culture and values quietly kill more deals than valuation ✅ How long you really have to stay on after a sale (it's shorter than the contract) ✅ The 30% haircut that hits unprepared businesses at the negotiating table ✅ The emotional side of selling: who are you after the business is gone? 💬 A FEW LINES THAT STUCK WITH US: "You're climbing the ladder, doing activity — but how do you know it's leaning against the right wall?" — Jane Gentry "You're not selling the past. The story you're selling is the future." — Jane Gentry "We get what we earn. Not what we deserve, but what we earn." — Ryan Frederick 📌 TIMESTAMPS: 00:00 — "You Need a Mirror": Cold Open 00:53 — Welcome to CEOs Unscripted 02:29 — Meet Ryan Frederick: A Serial Entrepreneur's Story 04:38 — The High-Risk Reality of Going Out on Your Own 05:37 — Job Security Is Dead & the Rise of the Influencer Career 08:35 — Get an Exit Plan the Day You Open the Doors 11:22 — The Full Calendar Trap: Working IN vs. ON the Business 14:04 — Ego, Identity & Why Founders Can't Let Go 17:28 — Surround Yourself With People Who'll Tell You the Truth 21:36 — Is Your Ladder Leaning Against the Right Wall? 22:07 — BREAKING: Transform Labs Has Been Acquired 23:49 — Sell the Future, Not the Past 24:33 — The "Mock Transaction" Test & Integration Readiness 25:33 — Prepping Your People & Leadership Succession 28:30 — How Long You Really Stay After the Sale 31:15 — Why Deals Die: Culture, Gut & Buyer's Remorse 35:36 — When Values Kill a Deal (The Company Car Story) 37:56 — The Emotional Side of Selling: Who Are You After? 40:52 — Succession Planning: Why Owners Wait Too Long 45:22 — Breaking the Owner's Delusion & the 30% Haircut 48:11 — What's Next for Ryan + The Truth About Retirement 51:43 — Closing Thoughts 👤 ABOUT RYAN FREDERICK: Ryan Frederick is the principal of Transform Labs (recently acquired) and a serial entrepreneur with multiple exits under his belt. He now spends much of his time traveling the country speaking on AI, and is staying on with the acquiring company to lead integration and growth. 🎙️ ABOUT CEOS UNSCRIPTED: Real talk that drives real growth for mid-market leaders. Host Jane Gentry brings unfiltered conversations with CEOs, founders, and executives scaling $10M–$500M businesses. No fluff, no jargon — just honest lessons from leaders who've been where you are. 👉 Subscribe so you never miss a candid conversation with a trailblazing leader. #Exit #MergersAndAcquisitions #CEO #MidMarket #BusinessValuation #SuccessionPlanning #Entrepreneurship #Leadership #ScalingUp #SellingYourBusiness

July 16, 2026

This Industrial CEO Using AI in Ways Most Tech Companies Have Not Figured Out Yet

Most CEOs talk about innovation. Drew Allen lives it. From taking his first trip to China at 13, to speaking Mandarin and Portuguese, to attending an AI hackathon hosted by the PayPal Mafia before most CEOs even knew what a large language model was, Drew Allen is not your average CEO. As the leader of Grace Technologies, Drew has quietly built one of the most experimentally driven, AI forward, high performance cultures in the industrial electronics space. And in this episode of CEOs Unscripted, he pulls back the curtain on exactly how he did it and what every CEO can learn from his approach. This is a conversation about curiosity, experimentation, reinvention and why the CEO who transforms themselves first is always the one who transforms their business. In this episode, you'll learn: ✅ Why being present in the market is the single most underrated competitive advantage in sales ✅ The Jim Collins flywheel that has driven Grace Technologies from day one ✅ How to build a culture of small scale experimentation so you never have to risk the farm ✅ Why Drew runs 50 to 200 experiments at any given time and what he is looking for ✅ The AI hackathon that sped up Grace Technologies' AI journey by 12 months ✅ How Drew used Claude to build a sales forecasting ensemble model in an afternoon that would have taken a data scientist six months ✅ Why you cannot coach drive and what to look for when hiring instead ✅ How to find the real bottleneck in your business using the five whys exercise ✅ Why transforming your business always starts with transforming yourself first 💡 Key Insight: "One successful experiment pays for a lot of small failures. If you are having to risk the farm, you are probably not thinking about the problem in the right way." 🎙️ CEOs Unscripted is a bi-weekly podcast for mid-market CEOs, no fluff, no jargon, just real conversations from leaders who have been in the trenches. 📌 SUBSCRIBE so you never miss an episode. #Leadership #CEOsUnscripted #ArtificialIntelligence #Innovation #Entrepreneurship #BusinessGrowth #MidMarket #HighPerformance #Manufacturing #AIForBusiness ⏱️ TIMESTAMPS: 00:00 Cold open: The management insight most CEOs overlook 00:59 Welcome to CEOs Unscripted 02:33 Meet Drew Allen, CEO of Grace Technologies 03:44 Drew's backstory and family entrepreneurial legacy 06:35 What 3M in Asia taught him about business 08:34 The Toyota Way and being present in the market 11:24 Why Grace Technologies needed to reinvent itself 13:27 Building an engineering team from scratch 14:52 The Jim Collins flywheel and how Drew applied it 16:40 Balancing instinct with strategy 17:48 Fire bullets not cannonballs 19:21 Decision making under pressure 20:20 Building a culture of experimentation 22:42 How SpaceX thinks about time vs cost 23:09 What failing the right way looks like 25:19 High performance culture and what it really means 26:40 Removing toxic high performers 27:33 Why you cannot coach drive 30:02 Hiring for curiosity over credentials 31:37 How Drew became an AI forward CEO 33:29 The AI hackathon that changed everything 35:48 How Claude sparked a wildfire inside the company 36:26 Transform yourself before you transform your business 39:42 Deciding which AI experiments are worth scaling 42:02 Building a sales forecasting model in one afternoon 44:31 What the data changed about how he leads 46:14 Why Drew believes entrepreneurship beats philanthropy 48:57 Advising and investing in early stage founders 49:39 Advice Drew gives entrepreneurs at every stage 51:46 How to find the real bottleneck using five whys 54:48 Drew's closing thoughts 55:42 Jane's closing thoughts

June 30, 2026

The Inner Journey Every CEO Hides From the World

Everyone talks about the strategy of being a CEO. Almost no one talks about the inner toll it takes. Charbel Zreik went from collecting cans on the street as a refugee from civil war to running companies, then spent years as a full time yoga and meditation teacher after his first CEO seat nearly broke him. Today he teaches at Wharton and works with CEOs on something most leadership conversations completely ignore, the inner journey behind the title. In this raw, deeply personal episode of CEOs Unscripted, Charbel sits down with Jane Gentry to unpack the five internal shifts every CEO needs to make to thrive under pressure, without sacrificing who they are to get there. In this episode, you'll learn: ✅ The five shifts every CEO must make to thrive instead of just survive ✅ Why risk is not just intellectual, it lives in your body, and how to manage it ✅ The nervous system tools Charbel uses including cold plunging, breath work and meditation ✅ How to recognize when your ego has been triggered before it takes control ✅ The difference between being nice and being kind as a leader ✅ Why dropping your attachment to outcomes makes you more effective, not less ✅ How to lead with low ego and a clear mission without losing yourself ✅ Why nearly 90 percent of founders are unhappy a year after exiting, and how to avoid becoming one of them 💡 Key Insight: "There is anxiety, but I am not anxiety. There is fear, but I have a choice in how I respond to it." 🎙️ CEOs Unscripted is a bi-weekly podcast for mid-market CEOs, no fluff, no jargon, just real conversations from leaders who have been in the trenches. 📌 SUBSCRIBE so you never miss an episode. #Leadership #CEOsUnscripted #MentalHealth #ExecutiveCoaching #Mindfulness #SelfAwareness #CEOMindset #PersonalGrowth #MidMarket #InnerWork ⏱️ TIMESTAMPS: 00:00 Cold open: The hidden weight every CEO carries on their shoulders 01:05 Welcome to CEOs Unscripted 02:40 Meet Charbel Zreik, CEO and founder of DHA Laboratory 02:58 The story behind his name and his namesake saint 03:53 From civil war refugee to food stamps to Cornell, Charbel's backstory 05:33 The people who believed in him before he believed in himself 07:14 Becoming an observer of CEOs and the inner journey nobody talks about 08:44 The breaking point that started it all, his first CEO seat in 2014 10:33 The five shifts to inner mastery as a CEO 12:34 Why all five shifts happen concurrently, not in order 12:51 Shift one, leading from a safe body 14:55 Becoming a master of your own nervous system 15:32 The practices Charbel uses daily, meditation, breath work, cold plunging 17:04 The special forces technique of naming what you feel 18:49 Why young leaders catastrophize and how to break it down step by step 20:20 What to do when you feel completely frozen 21:13 Shift two, leading with an open courageous heart 22:29 Why high performers become critical of others without realising it 23:57 How your nervous system silently affects everyone in the room 25:37 Shame, change and why being the change agent makes you a target 26:59 The difference between being nice and being kind as a leader 27:26 Shift three, a present and centered mind 28:30 Why the mind never stops solving problems, even at 4am 28:55 Dropping attachment to outcomes and committing to the process instead 30:43 How heavy planning actually creates more presence, not less 31:45 Jane's calendar confession and the cost of moving too fast 33:29 Jane's nighttime notebook trick for quieting a racing mind 34:24 Shiny object syndrome and constant mental movement 36:35 Charbel's nightly checkout ritual to tell his mind it is done for the day 37:57 Why you have to experiment to find what actually works for you 38:35 Shift four, leading with low ego and mission orientation 39:23 The 90 percent statistic on founders who regret how they exited 39:58 Knowing your personal ego triggers and catching them in real time 41:32 Jane's story of one-upping a network president and catching hersel

36 total episodes available

Recent guests on CEO’s Unscripted

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Colleen Japuntich

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John Kett

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Brad Stevens

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Raj Choudhury

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Thomas Grealish

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Brandt Hanley

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Letizia Latino

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Pat Alacqua

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Chris Happ

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Steve Hedricks

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Troy Place

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Stacey Tank

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Frequently asked questions

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What is CEO’s Unscripted?: Real Talk. Real Growth. Real Results in the Mid-Market

Jane Gentry consulted in enterprise for 20 years. And, after being a CEO in a mid-sized company, she realized why they say it is loneliest at the top. Mid-market CEOs learn their craft through trial and error or by reaching outside their organization for help.

She launched CEOs Unscripted as a bi-weekly podcast by mid-market CEOs for mid-market CEOs. Our purpose is to provide insight into the unscripted, unfiltered journeys of CEOs and Founders as they talk about their wins, losses, lessons and playbooks for growing and scaling their organizations. There is no better forum than learning from your peers.
How often does this podcast release new episodes?: This podcast updates daily.
Where can I listen to this podcast?: This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
Does this podcast accept guests?: Yes, this podcast regularly features guests.

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