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?