A Savvy DIY Investor Seeks Advice

Jun 26, 2024

Jacob, a savvy DIY investor, seeks advice from Kathleen, a Morgan Stanley Financial Advisor. They discuss managing company stock, planning for a million-dollar payday, buying a home in a hot market, and transitioning to passive income. The episode highlights the importance of seeking financial guidance and creating dynamic financial plans.

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ANECDOTE

Childhood Savings Match Shaped Habits

Jacob's parents matched his savings and locked the funds until age 18, turning saving into a game.
That habit plus compound interest grew his teenage savings to $10,000–$15,000, shaping lifelong financial behavior.

ANECDOTE

Startup Equity Became Major Windfall

Jacob joined an early-stage company and received equity that has appreciated in private-market value to about $1.5M.
He expects an IPO could convert that into a multimillion-dollar liquidity event for him and other shareholders.

ADVICE

Model Before You Liquidate Stock

Model risk and reward to decide how much company stock to keep versus liquidate around an IPO event.
Consider strategies that let you access equity value without fully selling the entire position early on.

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Jacob's upbringing instilled a strong savings ethic which led to substantial assets, including investments he’s been comfortable managing on his own. But Jacob’s life is about to get more complicated as his company eyes an IPO, which could lead to a million-dollar payday. Eager to know what his next move should be, Jacob sits down with Kathleen, a Morgan Stanley Financial Advisor, who plots out a plan to help him reach short- and long-term goals, including buying a home in a hot housing market and planning a transition to passive income.

What Should I Do With My Money? is also available on Apple Podcasts, Spotify, Google Podcasts and other major podcast platforms.

Visit our episode website for a deeper dive on topics covered in this episode like creating a financial plan and managing your company stock or to find a Morgan Stanley Financial Advisor to fit your needs. Also find important disclosures here.

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