Full Episode Page: Nick Berry: Multiple Exits and Using Equity-for-Advisory Partnerships to Build a HoldCo

In a unique role-reversal, Interview Connections founder Jessica Rhodes steps in as guest host to interview Nick Berry—entrepreneur, advisor, and founder of Redesigned.Business—about his own business owner’s journey. Nick opens up about building and exiting multiple companies, the difference between creating a scalable asset versus owning a glorified job, and how business design can position your company for long-term success, even if you never plan to sell. He shares how bespoke partnerships shaped his best exits, what green and red flags he looks for in operating partners, and how to build with purpose and structure. If you want to shift from founder chaos to clarity, this episode delivers actionable insight, real-world experience, and those rare “aha” moments.

Takeaways

• Know the difference between exiting well and just getting out
• Avoid building a business that traps you as the operator
• Design your business like it will one day be sold
• Create triggering events to guide equity decisions
• Look for clarity, conviction, and coachability in partners

Links

• Redesigned.Business
• Nick Berry on LinkedIn
• Nick on YouTube
• Nick on Instagram

Chapters

00:00 Nick Berry's Business Owner's Journey
05:40 Defining Successful vs. Unsuccessful Exits
08:33 Navigating Business Exits
11:04 Profit Planning
13:58 Stories of Successful Exits
16:37 The Timing of Selling a Business
19:40 Triggering Events in Business Sales
29:47 Closure in Business Decisions
31:12 Green and Red Flags in Operating Partners
33:03 Commitment and Earnestness
34:45 Run Your Business With an Investor's Mindset
36:16 Qualities of Effective Leaders
37:30 Diagnosing Business Problems
39:56 Implementing Effective Operating Cadences
42:20 Business Valuations
46:39 Coaching and Business Design Services

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The Business Owner's Journey podcast is where entrepreneurs, leaders, and innovators join host and entrepreneur Nick Berry to share their personal stories, challenges, and strategies from their journeys as business owners.

🟢 Official: NickBerry.info. tBOJ is hosted by Nick Berry, produced by Nick Berry, Kelly Berry & FCG.
🟢 Sponsors: SEOContentSurge, FR, Entrepreneur's Edge, Redesigned.Business