Advice for Investors
The Deep Dive Jan 28, 2026
Summary
Selling part of a winning position into strength locks in gains and sets cash aside for taxes and personal use.
Dot-com investors who rode gains back down still owed tax on the profits they had made, the guest recalls.
Keeping half a position after taking profits preserves upside to a possible 50-bagger without risking the original stake.
Traders' classic regret — never short enough in declines, never long enough in rallies — argues for a plan over emotion.
Todd Bubba Horwitz's takeaways
- Top takeaway The guest urges investors to take some profits off the table — if you own 1,000 shares, keep 500 and let the rest ride, accepting you may miss a bigger gain.
- He recalls internet-bubble investors who made large gains, then lost it all while still owing tax on the money they had made.
- He argues greed is acceptable only if the risk that comes with it is controlled, so gains should be banked for taxes and for yourself instead of staying fully exposed.
- He describes trader psychology: in a falling market traders are never short enough, in a rising market never long enough, and after any big move they say they should have been long.