Episode
Too Much of One Stock? How to Diversify Without Blowing Up Your Tax Bill (SB1843)
- Podcast
- The Stacking Benjamins Show
- Published
- May 18, 2026
- Duration seconds
- 3927
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Summary
You wake up, check your portfolio, and realize one stock has quietly become your entire retirement plan. Maybe it came from an employee stock purchase plan. Maybe Grandma left you a pile of Apple shares. Maybe you bought NVIDIA in 2012 because you liked the graphics card and forgot about it. However you got here, the problem is the same: one company now owns you. Joe and OG walk through exactly how to unwind it -- slowly, tax-efficiently, and without making the emotional decisions that cost people the most money. What You'll Walk Away With The four ways people end up with concentrated stock -- and which one has the easiest fix that most people skip entirely Why inheriting stock is actually the best time to diversify -- and the step-up in basis rule that eliminates most of the tax bill The conveyor belt strategy for employee stock purchase plans that keeps you collecting the discount without piling up company risk Why "I'll just grow around it" almost never works -- and the math behind why your stock tends to outpace your ability to diversify around it The question Joe asked every client in this situation: which outcome would upset you least -- and why that's the right starting point RSUs as a paycheck, not a loyalty pledge -- and the mental reframe that makes it easier to sell What the Merck/Vioxx story teaches about why the tax bill is almost never the real reason to hold concentrated stock When a slow systematic sell makes sense versus ripping the Band-Aid -- and how to decide which one you can actually live with The estate planning mistake that turns a free inheritance into a massive capital gains bill -- and why the $1 trick backfires every time The insurance planning framework OG and Anna walk through: life, disability, long-term care, and property/casualty -- inc…