When to exit a business is one of the most important — and most avoided — decisions entrepreneurs face. In this episode, Tom Wheelwright sits down with entrepreneur and investor Greg Jaggers to discuss how owners recognize the right moment to transition, scale, or sell.

Greg Jaggers, co-owner of J&H Livestock, shares firsthand lessons from building and expanding multiple businesses in a capital-intensive industry. He explains how entrepreneurs move from startup survival to operational stability and eventually to strategic decision-making about ownership, leadership, and legacy.

You will learn:

• How to evaluate whether your business is still an asset or has become a job
• The financial and operational signals that indicate it may be time to exit
• How growth stages change an owner’s role and risk exposure
• Why experienced entrepreneurs plan their exit long before they need one

This episode helps business owners think like investors. The goal is not simply to run a company longer — it is to maximize value, protect equity, and deploy capital into the next opportunity at the right time.

Order Tom’s book, “The Win-Win Wealth Strategy: 7 Investments the Government Will Pay You to Make” at: https://winwinwealthstrategy.com/

00:00 – Intro. 05:13 – The Beginning: “When things were tight, expand.” 10:00 – The Challenge: Impact of covid, interest rates, etc. 15:12 – The Revelation: Catalyst for change. 20:00 – What’s Next: “Speed dating” with investor bankers. 25:20 – Balance: Juggling growth in multiple businesses. 29:15 – Advice for entrepreneurs on selling & expansion. 33:00 – Private Equity Math: What buyers are looking for.

Looking for more on Greg Jaggers?
Website: https://jandhlivestock.com/
Facebook: http://www.facebook.com/people/JH-Livestock/100091607241726/
Email: greg@jandhlivestock.com

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