Source
When this applies
when you hold a massive concentrated position in an asset you built and must decide whether to diversify for pure financial optimization
The takeaway
A concentrated position can rationally be held past the point optimal portfolio theory recommends if the holder has enough wealth to absorb total loss, large embedded tax costs to selling, and values loyalty/identity over marginal expected return.
Why it works
Emotional attachment and identity-based loyalty can outweigh purely financial diversification logic when the holder doesn't need the money and faces large capital gains taxes on selling.
One level up
When you don't need the money, decisions can be driven by identity and values rather than optimization, as long as downside is survivable.
Where it stops holding
This stops working when you actually need liquidity, when the tax cost of holding is smaller than likely underperformance, or when the asset could realistically go to zero and threaten your standard of living.
Detail
situation: After leaving Microsoft as CEO, Ballmer had to decide whether to diversify out of a concentrated Microsoft position worth tens of billions, as Gates and Allen had done.
decision: He chose to hold almost all his Microsoft stock, reasoning that loyalty mattered more than optimization, that he could survive even a total loss, and that selling would trigger capital gains taxes that would only be justified if Microsoft underperformed the index by more than the tax rate.
outcome: His net worth grew from $20B in 2014 to $130B by the time of the interview, making him, per the hosts, arguably the best investor of the last 20 years despite never actively picking stocks.
lesson: Concentrated holding can be rational for a wealthy, loyal insider even when conventional advice says diversify, provided downside is survivable and tax costs are high.
In their words
I said, no, Charlie, but I'm not loyal.