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

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