What Happens After the Exit? - Paul Hickey

What happens after you sell your business? In this episode of What's Your Deal?, Matt Uhler sits down with Paul Hickey, CEO of Legacy Wealth Management, to talk about one of the most overlooked parts of business ownership: what comes next after the exit. Paul shares insights from decades of experience in global finance, investment banking, IPOs, mergers and acquisitions, and entrepreneurship. Together, Matt and Paul unpack why so many business owners focus on getting out of the business but fail to prepare for life after the sale. They discuss the emotional side of exit planning, the identity shift many owners face, how to avoid blowing through hard-earned wealth, and why creating a life plan is just as important as creating a financial plan. Paul also explains the value of starting early, building a team before the sale, and using strategic planning to reduce taxes and generate sustainable income after an exit. This is a valuable conversation for business owners who want to sell wisely, protect their future, and build a true legacy for the next generation.     Timestamps     0:16 – Matt introduces Paul Hickey and his background   2:01 – Paul's journey from tech entrepreneur to IPO to investment banking   4:10 – What Legacy Wealth Management and Legacy Exits actually do   5:30 – Why exit readiness is only part of the equation   6:42 – The emotional side of selling a business   8:02 – What business owners often do wrong after a successful exit   9:50 – Paul's advice: protect a baseline income before taking new risks   12:17 – When owners should begin exit planning   13:58 – Why selling a business is more like an Ironman than a 5K   15:26 – Reducing taxes and increasing income after a sale   18:43 – The difference between average returns and intentional wealth strategy   19:16 – What "non-correlated investments" means   22:25 – Who qualifies as an accredited investor   24:02 – What legacy really means   25:30 – The danger of generational wealth without structure   28:56 – Family bank concepts and distributing wealth responsibly   30:02 – How deep legacy planning can go   30:40 – Helping business owners who have everything tied up in the business   32:17 – Lessons from The Millionaire Next Door   34:38 – Dreamscaping and defining what financial freedom actually looks like   37:11 – The surprising mentor who helped Paul most   40:33 – Where to find Paul Hickey     Connect with Paul Hickey:   Legacywealthmg.com   [email protected]   LinkedIn: https://www.linkedin.com/in/paulchickey/     Connect with Matt Uhler / Amped Success:   Instagram: @ampedsuccess   Website: Ampedsuccess.com   Email: [email protected]   LinkedIn: https://www.linkedin.com/in/matt-uhler-a9896612/   Want to be a guest or sponsor an episode?   If you'd like to be a guest on What's Your Deal? or are interested in sponsoring an episode, reach out to: [email protected]   Listen & Subscribe:   Be sure to subscribe on Apple Podcasts, Spotify, or wherever you listen to podcasts. If you enjoyed this episode, please leave a review. It helps more people discover the show.