The Exit Whisperer

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

Sherrell Dorsey joins Carrie Kerpen to share her journey of transforming a newsletter into a data-driven media company that highlights Black innovation, underrepresented founders, and the business stories that traditional media overlooked.

This episode explores founder burnout, media entrepreneurship, data as a business asset, market timing, team leadership, and the emotional complexity of selling a company.

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.

3:35 - How The Plug Got Started

8:38 - Deciding to Build Something Bigger 

12:46 - Bootstrapping & Building the Data Product

17:08 - Founder to CEO: Leading a Team

21:12 - Recognizing It Was Time to Exit

29:20 - Finding a Buyer & Shopping the Deal

29:59 - Communicating the Sale to the Team

33:36 - Life After the Exit

38:19 - Knowing You're a Zero-to-One Founder

41:27 - What's Next: Climate Tech

Becca Berg, co-founder of Dubsado, shares how a chaotic moment in her photography business became the spark for building one of the most beloved systems for service providers. Carrie and Becca talk about client experience, scaling with your spouse, the sacrifices behind fast growth, and what it really takes to build a business that feels both beautiful and functional.

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.

2:47 - How Dubsado Got Started

7:00 - Working with Your Spouse

7:39 - The Blessings & Challenges of Building a Business with Your Spouse

13:48 - Bootstrapping a Tech Business

19:13 - Planning for Exit

23:14 - Navigating the AI & Tech Landscape

24:37 - Burnout & Year Nine

Alex Schinasi, founder of Hulken, joins Carrie Kerpen to unpack the real entrepreneurial journey behind raising venture capital, pivoting under pressure, selling companies, and building again.

From Ivy to Hulken, Alex shares why billion-dollar valuations do not always mean founder freedom, how pivots create momentum, and what it means to be truly “acquired, not retired.”

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.

2:22 - Introducing Hulken

4:45 - Company #1: Ivy — The Origin Story

9:58 - Racing to Exit: Finding Product Market Fit

12:21 - The Ivy Exit — From Unlock to Deal

12:45 - How the Acquirer Found Them (LinkedIn!)

16:36 - Why Build Again? The Zero-to-One Mindset

16:45 - Company #2: Clay — Healthcare to EdTech

19:55 - The Clay Exit — Three Term Sheets

24:41 - Hulken Origin Story 

28:18 - VC vs. Bootstrap — How to Choose

29:58 - What's Next for Hulken?

Carrie Kerpen kicks off Season 7 of The Exit Whisperer with a raw behind-the-scenes look at building The Whisper Group after selling her first company.  From crossing the seven-figure mark to managing cash flow, Carrie opens up about what it really feels like to start again, scale again, and build another business after an exit.

This season is supported by Dubsado, Theory Planning Partners, Wealthrive, and The Luckey Capital Group — partners helping founders streamline their businesses, plan their wealth, protect more of what they earn, and access capital when they need it.

0:49 - Building The Whisper Group

1:37 - Crossing the 7-Figure Milestone

4:17 - The Whisper Group & Advisor Model

4:51 - Renaming the Community: Acquired Not Retired

6:43 - Podcast Updates & Why She Added Sponsors

8:58 - Sponsor #1: Wealthrive

10:21 - Sponsor #2: Theory Planning Partners

12:07 - Sponsor #3: Dubsado

14:00 - Life on the Road & Speaking Tour

16:02 - On Conviction & Pushing Through Hard Days

In the first live recording of The Exit Whisperer at Luminary, Suneera Madhani shares how she turned a rejected idea into one of Florida’s biggest startup success stories. At 25, she pitched a subscription-based payment processing model to her employer. They passed—so she quit, moved back home, teamed up with her brother, and built Stax from scratch.

Suneera breaks down what it really took to scale, raise capital later than most fintech companies, survive investor rejection, and navigate multiple exits—including Stax’s $1B valuation as Florida’s first unicorn.

00:01 How Suneera Madhani Got Started

04:46 The Reality of Being a Founder Mom

08:29 Learning to Become a CEO

11:45 The Rejected Business Idea

14:07 Pitching Her Boss

16:14 "You Can't Go Back To The Same Job"

17:28 Quitting to Start the Company

18:02 Explosive Early Growth

18:41 Breaking Down the Exits

20:17 What Investors Actually Fund

21:43 Rejection, Bias & Scaling Challenges

23:57 Knowing When You’re Ready

26:30 Founder vs CEO Mindset

29:36 The Playbook for Scaling

33:15 Why Cool Doesn’t Equal Business

36:08 Acquired, Not Retired