Advertise on podcast: The Exit Whisperer

Gail Becker shares how she left corporate America, invested in an idea almost no manufacturer wanted to make, and built CAULIPOWER into a major frozen food brand. Years later, her exit brought the story full circle when the manufacturer that took a chance on her at the beginning became part of the deal. This episode is sponsored by: Luminary, a global professional community where founders, investors, and professionals come together to learn, connect, and grow. Use code WHISPER10 for 10% off your first 12 months of membership at www.weareluminary.com.  The Whisper Group helps women founders get exit-ready by connecting them with experienced exited entrepreneurs for the strategy, guidance, and support they need to prepare for a successful exit. Learn more at www.wearethewhispergroup.com. 2:40 - CAULIPOWER's Origin Story 4:57 - Taking the Leap 6:44 - Funding & Scaling Frozen Food 10:24 - Raising VC & Going into Walmart 13:06 - Cauliflower as a Movement1 5:57 - Finding a Manufacturer 18:53 - The Exit Story 24:49 - Post-Deal Feelings 27:42 - Advice for Founders 30:07 - Tuning Out the Noise

Carey Peters shares the story behind building Health Coach Institute to nine figures, taking on private equity, losing control, and navigating a final sale that didn't happen the way she expected. It's a candid conversation about ownership, investor dynamics, founder knowledge, and what Carey learned when things went sideways. You can find Carey at www.CareyPeters.com ---- This episode is sponsored by Jessika Graham. Jessika Graham is an M&A attorney who works closely with female founders helping them understand the deal, protect their interests, and move through the sale process with clarity. Connect with Jessika on LinkedIn: https://www.linkedin.com/in/jgrahamesq/ ---- 2:12 - From Actress to Coach: An Unconventional Start 6:36 - Struggling as a Coach & Meeting Stacy 7:35 - Co-founding Holistic MBA 14:20 - Building Health Coach Institute (HCI) 17:14 - The Platform Play & Acquiring Schools 22:55 - Taking Private Equity: What Changed 32:24 - The Final Sale: When Things Go Sideways 38:42 - Reflections: Surrender, Growth & What's Next

M&A attorney Jessika Graham joins Carrie Kerpen to break down what founders need to know before an exit, from getting your contracts and IP in order to choosing the right attorney, understanding what you're signing, protecting your leverage, and why ChatGPT should never replace real legal counsel during a transaction. ---- This episode is sponsored by Jessika Graham. Jessika Graham is an M&A attorney who works closely with female founders on the sell side, helping them understand the deal, protect their interests, and move through the sale process with clarity. Connect with Jessika on LinkedIn: https://www.linkedin.com/in/jgrahamesq/ ---- 2:23 - Jessica's Path Into Law 3:00 - From Bankruptcy to Transactional Law 5:56 - Finding Her Place in M&A 8:14 - Championing Female Founders 11:26 - What Makes or Breaks a Deal 13:21 - Hiring the Right M&A Attorney 16:06 - EBITDA & Educating on Instagram 18:35 - ChatGPT in Lega l20:36 - Privilege, Trust & Walking Through Documents 21:50 - The Missing Link in Legal 23:13 - Transparent Pricing 24:55 - Final Advice for Female Founders

Ingrid Zapata Read joins Carrie Kerpen to share how she built Working Momkind into a community of more than 250,000 moms, stepped into a new chapter, and later realized the brand, audience, and partnerships she had built were valuable enough to sell. ---- This episode is sponsored by: Luminary, a global professional community where founders, investors, and professionals come together to learn, connect, and grow. Use code WHISPER10 for 10% off your first 12 months of membership at www.weareluminary.com.  The Whisper Group helps women founders get exit-ready by connecting them with experienced exited entrepreneurs for the strategy, guidance, and support they need to prepare for a successful exit. Learn more at www.wearethewhispergroup.com. ---- 1:17 - Meet Ingrid Zapata Reid 3:16 - Building Working Momkind 7:32 - Growing the Private Community 9:17 - Monetizing & Becoming the Queen of Pivoting 14:30 - Deciding to Sell 19:48 - Valuing the Asset 22:23 - The Deal & Partnership with Trish 25:00 - What's Next for Ingrid

Carrie Kerpen sits down with Jessica Zweig to talk about building SimplyBe., hitting burnout, and choosing an exit that gave her freedom. Jessica shares how she negotiated with buyers, protected her team, and stepped into her next chapter without apologizing for wanting more. 4:30 - Building SimplyBe 8:02 - Burnout and the Decision to Sell 11:52 - The Egypt Trip and Mindset Shift 14:48 - Negotiating the Hawk Media Deal 22:06 - Life After the Exit 25:59 - Building the Feminine Frequency Business School 29:24 - Closing Thoughts

Sharon Thony Lee sold SLT Consulting to Fiverr just two years after starting the agency and spent the next five years operating it inside the public company. Then she realized something she hadn't considered before: she could buy it back. Sharon shares what it took to become an owner again, how she's running SLTC differently this time, and why she's already building toward another potential exit. ---- This episode is sponsored by Luminary, a global professional community where founders, investors, and professionals come together to learn, connect, and grow. Use code WHISPER10 for 10% off your first 12 months of membership at www.weareluminary.com. ---- 1:09 - Welcome Back & Recap 2:12 - SLTC's Origin & Sale to Fiverr 3:14 - Realizing She Could Buy It Back 9:55 - The Back-of-the-Napkin Moment 13:20 - Running SLTC Differently 15:39 - The Future & Next Exit Plan

Cate Luzio joins Carrie Kerpen to break down how founders can use acquisitions to grow. She shares what buyers actually look for, why profit matters more than potential, and how to evaluate whether a company is truly worth acquiring. ---- This episode is sponsored by Luminary, a global professional community where founders, investors, and professionals come together to learn, connect, and grow. Use code WHISPER10 for 10% off your first 12 months of membership at www.weareluminary.com. ---- 2:32 - Leaving Corporate America 6:01 - Building the Original Business Plan 9:11 - Bootstrapping vs. Raising Funds 15:20 - Building the Partner Network & COVID Pivot 18:39 - Surviving COVID & Digital Membership 21:28 - First Acquisition: Declare 27:02 - Sourcing Acquisitions Through Luminary Members 30:40 - Deal Structuring & Lessons From Failed Deals 35:22 - Exit Planning Philosophy 38:04 - Advice for Women Entrepreneurs & Closing

Bridget Firtle joins Carrie Kerpen to share how she built Owney’s Rum, sold it, stepped away, and bought the brand back. This conversation is about identity, timing, founder instinct, and what changes when you get the chance to build again with more experience and a bigger vision. ---- This episode is sponsored by Luminary, a global professional community where founders, investors, and professionals come together to learn, connect, and grow. Use code WHISPER10 for 10% off your first 12 months of membership at www.weareluminary.com. ---- 2:20 - The Buyback Story Begins 4:36 - Untangling Identity from Owney’s 6:26 - How the Deal Came Together 12:18 - 20s vs. 40s: Building With More Wisdom 16:11 - Building Beyond Owney’s: The Bigger Vision 17:50 - Lessons Learned & What's Next

Carrie Kerpen sits down with Sharon Gillenwater to unpack how she went from a $25 million exit to trying to buy back the company she sold and deciding to rebuild from scratch. ----- This episode is sponsored by Luminary, a global professional community where founders, investors, and professionals come together to learn, connect, and grow. Use code WHISPER10 for 10% off your first 12 months of membership at www.weareluminary.com. ---- 1:05 - From TikTok Fame to Shutdown 1:58 - Trying to Buy the Company Back 7:30 - No Non-Compete, Deciding to Rebuild 9:33 - Customer Demand Forces the Decision 13:55 - Funding the Restart 18:06 - Building with AI, Then and Now 22:50 - What Winning Looks Like This Time 23:46 - Thinking About the Next Exit

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

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

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)

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

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

Paige Yomogida joins Carrie Kerpen to share how she turned a personal healing journey through strength training into Propensity Fitness — and then built the systems that allowed her to sell it. This episode explores discipline, intuition, systems, personal growth, and the courage it takes to know when a business has served its chapter.   This episode is sponsored by Dubsado. Dubsado helps service-based business owners streamline proposals, contracts, invoices, payments, and client workflows all in one place. Visit www.dubsado.com and use code WHISPER for 30% off.   2:25 - Paige's Early Relationship with Food & Fitness  5:08 - From Powerlifting Competitor to Personal Trainer  8:28 - Leaving Finance to Pursue Her Passion  9:19 - Going Online During COVID & Launching Propensity Fitness  10:57 - Building Systems & Scaling the Business  13:48 - Recognizing It Was Time to Move On  15:38 - Mentoring Other Fitness Coaches  21:07 - The Exit: Selling Propensity Fitness in 72 Hours  26:02 - Health as the Foundation of Business Success