Preserve the Win: Risk-Smart Wealth Moves Before (and After) Your Exit with Tim Smith

In this Scale to Exit episode, Alejandra Santos delves into a conversation with certified financial advisor and entrepreneur Tim Smith on how to preserve the big win well before a sale and long after the close. Tim unpacks the money misconceptions many owners bring from the boardroom to Wall Street, why liquidity beats “asset-rich but cash-poor,” and how to right-size risk without picking five “favorite” stocks.

You’ll hear practical pre-exit moves (tax/estate structures, trust strategies, and due diligence readiness) and post-exit frameworks for diversification, income needs, and avoiding decision paralysis. They also riff on AI hype vs. reality, crypto speculation vs. adoption, and the investor book Tim gives clients.

What you’ll learn

• When to start funneling cash out of the business—and why illiquid real estate isn’t always first

• A simple liquidity cushion framework + marketable, conservative instruments

• Diversification that actually reduces risk (funds/ETFs > five stock bets)

• Teaming up: the “quarterback” model across tax, legal, and wealth

• Post-exit mindset: preserve the win, don’t chase 20% every year

Resources
• Extraordinary Popular Delusions & the Madness of Crowds
• Tim’s channel: “The Financial Dad” (YouTube)

Connect
Guest—Tim Smith https://www.linkedin.com/in/timothy-l-smith-cfp-r-b1293443/
Host—Alejandra Santos | IntoTheNext.com | Scale to Exit Podcast www.thealejandrasantos.com https://www.linkedin.com/in/aalejandrasantos

 

Chapters
00:00 Why Tim does this work
02:00 Owners’ biggest money misconceptions
04:30 When to start personal wealth planning
08:30 Liquidity > illiquid assets
12:45 Pre-exit tax & trust strategies
15:10 Due diligence that speeds a sale
17:10 Portfolio strategy after a transaction
22:30 AI & crypto: speculation vs. adoption
37:45 Identity shifts post-exit
44:00 Practical risk management (diversify)
49:15 “Preserve the win” mindset