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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 Paul@hickey.com LinkedIn: / paulchickey Connect with Matt Uhler / Amped Success: Instagram: @ampedsuccess Website: Ampedsuccess.com Email: admin@ampedsuccess.com LinkedIn: / 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: admin@ampedsuccess.com 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.