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

KK Hart shares her unconventional path from corporate life to building and acquiring multiple businesses with no debt and no outside capital. This episode explores cash flow, wealth building, family, acquisitions, and what happens when a founder stops waiting for an exit to create freedom.

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.

3:03 - KK's Fostering Journey & Modern Family Office 

5:29 - From Corporate to Entrepreneurship 

11:58 - First Acquisition: The Dance Studio 

12:33 - How to Value & Buy Your First Business 

16:29 - Building a Portfolio of 10 Acquisitions 

17:37 - Cash Flow 2.0 Explained 

19:25 - From Dance Studio to Family Office 

21:02 - Portfolio Allocation Philosophy 

23:23 - How Much Capital Do You Need to Start

32:04 - Advice for Buyers & Sellers 

34:15 - Raising Entrepreneurial Kids 

35:22 - How Much Money Is Enough

Kaitlyn Carlson from Theory Planning Partners joins Carrie Kerpen for a powerful conversation about money, values, and preparing for the exit of your dreams.

From surviving toxic power dynamics in wealth management to building a financial planning firm rooted in honesty and advocacy, Kaitlyn breaks down what founders should be thinking about long before they sell.

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.

4:13 - Kaitlyn's Background & Ice Hockey

6:38 - Career Path into Finance

13:33 - The AUM Model Explained

23:58 - Mindset: Abundance vs. Scarcity

26:53 - Theory Planning Partners' Flat Fee Model

33:26 - When to Start Planning Your Exit

35:52 - Investment Categories & Shiny Objects

42:25 - Advice for the First-Time Founder

Gesche Haas joins The Exit Whisperer just before selling Dreamers & Doers, the women entrepreneur community she built over 12 years. She shares how she grew it without outside funding, why the right buyer mattered, how SBA financing helped shape the deal, and what founders should consider when an exit becomes personal.

This episode is sponsored by The Whisper Group, helping women founders navigate exit opportunities with clarity, strategy, and confidence.

2:01- Welcome and how Gesche and Carrie met

3:50 - The story behind Dreamers & Doers

6:58 - The first acquisition conversations

8:09 - Finding the right buyer

10:19 - How SBA financing shaped the exit deal

12:10 - Sorting through the exit decision and valuation

16:06 - Due diligence and getting to the finish line

18:41 - Life after the exit and what comes next

Marina Khidekel joins Carrie Kerpen just days after selling Hugimals to Relatable. She shares how she built a design-forward weighted plush brand from the ground up, bootstrapped it to seven figures, chose control over outside funding, and navigated the reality of selling her company while stepping into a new role with the buyer.

This episode is sponsored by The Whisper Group, helping women founders understand their exit options, prepare for the right opportunity, and turn the businesses they’ve built into life-changing assets.

2:51 - The origin story behind Hugimals
4:48 - How Marina brought the product to life
6:53 - Turning the product into a business 
10:03 - Funding the growth 
12:57 - Knowing when it was time to sell
15:48 - Manifesting the right acquirer: how Relatable entered the picture
16:48 - Inside the year-long M&A negotiation process
19:08 - The biggest lessons Marina learned from selling her company
22:37 - What it felt like when the deal officially closed
23:29 - Marina’s first day at Relatable and what comes next
24:55 - Marina’s letter to herself one year from now