The Exit Whisperer

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