The Stacking Benjamins Show · Friday, October 2, 2026
The panel discusses the dilemma of a stock becoming 40% of a portfolio after a significant win. Doc G advocates for selling and diversifying to protect wealth, highlighting the risk of concentration and the impact of taxes. OG, however, suggests holding onto the winner, comparing it to potentially holding Home Depot, which yielded massive returns over decades.
“I am in for selling and diversifying.”
“So if you stay in the concentrated risk allocation, the likelihood you could lose it all or lose a big percentage of it is high.”
“I would not sell the stock. You would not sell the stock. You would keep it. Yeah. It's winning, man.”
“But the value is in the holding of the stock. So I'm saying I would have been. I don't know if I'm in or out. I probably would have gotten rid of the 40% of my portfolio as well and diversified. But if you really want to roll the dice and see if you get the big return and be on OG's team, I mean, there may be a reason to hold on to that because you could have a Home Depot on your hands and you won't know it until you've held it for 40 years.”