The Exit Whisperer

Women-owned businesses capture just 0.8% of the total exit value in the US. Carrie Kerpen is here to change that, through sharing the stories of women who have broken through and sold their businesses. Having sold her own business for 8-figures in 2021, Carrie knows what it takes to build a sellable brand. She also knows that the experience can be different for women than it is for men because she has personally interviewed hundreds of exited female founders. New Episode Every Tuesday!

The Exit Whisperer is a business podcast hosted by Carrie Kerpen, with 93 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.

Carrie Kerpen hosts The Exit Whisperer, a business show with 93 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 #91

  #91 - Lauren Luckey (The Luckey Capital Group)

  Aug 18, 202636 minS7

  Lauren Luckey shares how she went from military service and a near-CIA career to building and acquiring 16 businesses. This episode demystifies buying a business, challenges the online fantasy of “easy” acquisition entrepreneurship, and shows what it really takes to build wealth through grit, timing, and smart capital deployment. This episode is sponsored by The Luckey Capital Group. The Luckey Capital Group helps small business owners access smart, practical capital when they need it most. Learn more at www.theluckeycapitalgroup.com . 2:24 - Lauren's Military Career 9:45 - Leaving the Army & CIA Rejection 17:05 - First Business: Buying a Dry Cleaner for $1 15:27 – Going All In: Selling Everything & Living in the Store 17:43 – Scaling to 16 Businesses 24:14 - The Fire: Losing $2.7 Million 28:22 - Being a Woman Is a Strategic Advantage 32:27 - The Luckey Capital Group: Filling the Gap for Small Businesses

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  Episode #89

  #89 - Sam Gardner (HappyPillar)

  Aug 11, 202634 minS7

  Sam Gardner joins Carrie Kerpen for one of the most honest conversations about venture capital, motherhood, burnout, and selling under pressure. Through the story of HappyPillar, Sam reveals what happens when a mission-driven AI company has traction, funding, and heart — but not enough runway to keep playing the VC game. This episode is sponsored by Wealthrive. Wealthrive helps business owners keep more of what they earn through proactive tax strategy and planning before, during, and after an exit. Learn more at www.wealthrive.com . 31:28 - Lessons from The Exit Whisperer Community 3:57 - HappyPillar Origin Story 7:59 - Raising Venture Capital 8:47 - The VC Model & Running Out of Runway 13:20 - Learning from The Raise 14:43 - Working From The Delivery Room 15:21 - The Board Says It's Time to Sell1 5:40 - Working With The Whisper Group 16:39 - The Sales Process & Asset Deal 17:57 - Liquid Preference & What Founders Actually Take Home 21:12 - Finding HappyPillar a Home 22:37 - The Emotional Reality of "Worthless Shares" 21:46 - Reconciling the "Exited Founder" Narrative 27:10 - The Birth of The Continuity Company 28:43 - VC Partners Paying for Founder Maternity Coverage

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  Episode #88

  #88 - Jenna Kozodoy (Wealthrive)

  Aug 4, 202636 minS7

  Jenna Kozodoy from Wealthrive joins Carrie Kerpen to explain how entrepreneurs can use proactive tax strategy to protect their wealth before, during, and after an exit. From her background at Bridgewater and Goldman Sachs to helping entrepreneurs keep more of what they earn, Jenna breaks down why tax planning is not just something you do when you sell — it is something you build into the business early. This episode is sponsored by Wealthrive. Wealthrive helps business owners keep more of what they earn through proactive tax strategy and planning before, during, and after an exit. Learn more at www.wealthrive.com . 2:01 - Jenna's Figure Skating Background 3:21 - Bridgewater: Radical Truth & Radical Transparency 5:25 - From Bridgewater to Goldman Sachs 8:49 - The Birth of Wealthrive 14:22 - The 3 Ds: Discover, Design, Deploy 16:07 - Case Study: $5M Tax Bill Reduced to Zero 19:07 - When Should You Start Tax Planning? 23:00 - Is It Too Late to Call Before You Sell? 24:58 - Should You Be Worried About Audits? 32:53 - How to Reach Wealthrive 33:48 - Why Jenna Lives in Puerto Rico (Act 60 Tax Benefits)

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  Episode #90

  #90 - Rachel Glass (GLOSSLAB)

  Jul 28, 202628 minS7

  Rachel Glass joins Carrie Kerpen to share the real story behind building and selling GlossLab, a branded, hygiene-focused nail salon concept that grew from two bootstrapped locations into a venture-backed business. This episode dives into raising more than $20 million, scaling too quickly, investor conversations, identity after a difficult outcome, and Rachel’s next chapter as she builds a new skincare brand with the lessons of GlossLab behind her. This episode is sponsored by Theory Planning Partners. Theory Planning Partners helps founders and business owners make smarter decisions around wealth, financial planning, and life after exit. Learn more at www.theoryplanning.com . 2:18 - Rachel's Background in Finance 4:01 - Building the First Model (Hiring TaskRabbits to Count Salon Traffic) 4:41 - Bootstrapping the First Two Locations 7:13 - COVID Hits Right Before the Fundraise 8:16 - Scaling to 20 Locations Across 4 Cities 8:56 - Pressure to Grow Too Fast 10:22 - Pivoting to a Franchise Model 12:34 - Having Hard Conversations with Investors 16:56 - The Sale: An Investor Acquires the GlossLab IP 18:47 - Rebuilding Her Identity After the Exit 20:46 - What's Next: Launching Le Balm 21:12 - Introducing Le Balm (Petroleum Jelly, Reinvented) 26:10 - Advice for Women Founders: It's a Grind

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  Episode #87

  #87 - Caitlyn Wells (Upwell Strategies)

  Jul 21, 202631 minS7

  Carrie Kerpen’s first acquisition started as an acquihire—but quickly became something much bigger. Once Caitlyn Wells and Upwell Strategies joined The Whisper Group, their operations work became a key part of helping founders prepare for exit. In this episode, Carrie and Caitlyn share how the deal came together, why the partnership created immediate value, and the bigger lesson: you are not only buying what exists today but investing in the people and shared future you can build together. This episode is sponsored by The Whisper Group , helping women founders navigate exit opportunities with clarity, strategy, and confidence. Learn more at www.wearethewhispergroup.com 2:40 - Caitlyn’s Background and the Start of Upwell Strategies 4:39 - How Caitlyn and Carrie Met 6:13 - Building Their Working Relationship 9:04 - Planning Systems for Maternity Leave 11:01 - Caitlyn’s Operations Advice for Founders 14:16 - How the Acquisition Came Together 17:13 - Navigating the Negotiation and Legal Process 18:56 - Scaling Operations at The Whisper Group 23:00 - What Caitlyn Wanted From the Deal 25:09 - Equity, Timing, and the Mental Load 28:36 - The Five-Year Vision for The Whisper Group

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