THE ROTH GUY

The X’s and O’s of Buying or Selling a Business in Retirement with George Rosen and George St Pierre III
January 8, 2026

We’re excited to be back today with George Rosen and George St Pierre III of Contango Investments, Inc., to dive deeper into what it really takes to buy or sell a business as part of a retirement strategy.

In part two of this conversation, the Georges walk through the practical X’s and O’s- from self-assessment and financing realities to SBA loan requirements, due diligence, and why geography and cash flow matter more than most people realize. They also flip the script to the seller’s side, explaining how advance planning and building a strong advisory team can dramatically increase business value.

📌 Here’s some of what we discuss in this episode:

🔍 Self-assessment before buying a business

💰 SBA financing, cash flow & debt service coverage

📍 Why location and owner involvement matter

🧾 Due diligence and avoiding costly missteps

🚪 Exit planning that increases long-term value

🧠 The power of a coordinated advisory team

0:00 – Intro

0:47 – Self-assessment and financing

3:42 – Location, operations, and buyer realities

8:00 – Seller readiness and removing the owner

14:18 – Coaching and long-term strategy

15:34 – Building the right professional team

Contango Investments:

Website: https://contangoinvestments.com/

LinkedIn: https://www.linkedin.com/company/741644/admin/dashboard/

Facebook: https://www.facebook.com/Contangoinvestmentsinc

Instagram: https://www.instagram.com/contango_investmentinc/

X:  https://x.com/biz_broker

George Rosen:

LinkedIn: https://www.linkedin.com/in/floridabusinessvaluations/

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Episode Transcript

Note: This transcript was produced using AI, so please excuse any typos and inaccuracies…

Speaker 1  00:00

Back for another edition of The Roth Guy with Jude Wilson, and this week we have the Georges returning to talk with us about how to buy a business, kind of the X’s and O’s of what it looks like, especially if you’re a retiree or a pre retiree thinking about getting into a new industry when it comes to changing your life and building a future for yourself. So with that, we’ll welcome the fellas back in Jude, how you doing?

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