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

Natalie built a wildly recognizable beauty brand, raised $13 million, got it into major retail, and still came away with the same uncomfortable realization a lot of founders quietly have: the number in the headline and the money you actually feel are not the same thing.

This isn’t a Cinderella story. It’s what happens when a smart founder tells the truth about money, control, and what an exit actually feels like after the applause stops.

01:09 Meet Natalie Mackey

02:44 The Pivot That Changed Everything

05:15 Why Beauty Breaks E-Commerce Rules

07:25 The Product That Took Off Overnight

08:09 Fundraising Is Timing, Not Talent

13:06 The Decision to Sell Instead

18:22 The Truth About “Winning” an Exit

19:07 Why the Second Time Feels Different

20:38 AI Is Giving New Founders an Edge

21:30 Losing the “Founder” Identity

24:45 The Pressure to Do It Again

26:33 Why You Just Have to Start

28:00 Money, Risk, and Never Feeling Safe

30:18 The Traits That Actually Matter

In this episode of The Exit Whisperer, Carrie sits down with Andrea Johnston, founder of Pure Communications, to unpack what most founders never say out loud: sometimes the business is thriving, the numbers are strong, the offers are real, and you still know it’s time to sell.

They get into building with intention, why niche agencies scale faster than scattered ones, what private equity actually wants, and how to know whether you’re growing a business… or just feeding a machine that no longer fits your life. Andrea also opens up about what she would do differently, why succession planning matters more than founders think, and the hard truth that reacting emotionally will cost you more than almost any bad strategy.

00:54 Meet Andrea Johnston

02:48 Why She Left Corporate to Start Her Agency

04:51 The Gap Between “Starting” and Building a Real Business

05:23 How She Scaled Using Only Her Network

07:27 The Decision to Niche Down

10:31 The Real Growth Engine: Existing Clients

12:15 How Private Equity Entered the Picture

17:38 Inside the Sale Process

18:14 What Actually Changes After You Sell

19:28 How Acquisitions Create Opportunities for Your Team

20:15 The Second Exit: Moving Fast in Private Equity

21:35 Burnout at the Top

25:22 Taking 2 Years Off

28:41 Building “Fuel for Female Founders”

32:24 Final Lessons on Exits, Growth, and Letting Go

In this episode of The Exit Whisperer, Carrie sits down with Lana Powers (founder of Powers PR) to unpack a truth most founders ignore until it’s too late: success can still be the wrong path if it’s killing you to sustain it.

They get into rebuilding a company just to make it sellable, why hitting a peak can be more dangerous than failing, and how founders confuse “being needed” with “being healthy.” Lana also opens up about the aftermath of selling, the second-guessing, the “what if I kept going,” and redefining success beyond revenue, status, or control.

00:56 Meet Lana Powers

02:57 Hitting Rock Bottom As A Founder

03:57 Starting Powers PR From Scratch

05:17 Growing Slowly Into Real Momentum

06:15 Scaling While Pregnant With Twins

10:53 The Reality Of Running A PR Agency

14:58 Burnout In The Wellness Industry

15:54 Rebuilding The Business The Right Way

17:10 The Client That Changed Everything

18:50 Learning To Detach As A Leader

19:37 When Your Body Starts Breaking Down

22:35 How She Chose The Right Buyer

23:58 Life After Selling The Business

27:00 What Success Looks Like Now