What Happens After the Exit? - Paul Hickey
What's Your Deal? | Buying Businesses, Business Acquisitions, Investing & Exit Strategies
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Show Notes
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:
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/
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