If you ever played Super Smash Bros, you know “Sudden Death” mode:
- Everyone starts at 300% damage
- One clean hit and you’re gone
- The whole game is hanging by a thread
I played a lot of Smash growing up (even made it to the semifinals of a college tournament).
Here’s the thing:
If you’re up two stocks on someone — already winning comfortably — you don’t keep playing like it’s sudden death.
You stop doing stupid high-risk moves.
You control the stage.
You close the game out.
A lot of engineers and founders manage their money like the exact opposite.
I see:
- Net worth in the mid-7 to low-8 figures
- Concentrated stock exposure everywhere
- Leverage, options, and private deals stacked on top
- No real tax or withdrawal plan
They’ve already won the game financially…
…but their portfolio is still playing sudden death at 300% damage.
Then they ask me:
“If I pay you $X, how many dollars will you make me?”
On the surface, it’s a fair question. What’s the ROI on the engagement?
But the more aggressively someone frames it that way, the more honest I have to be:
If you want me to maximize the projected ROI, I can do that easily — max out leverage, load up on private equity, forget diversification, and hope nothing goes wrong.
That’s just not the optimal approach for anyone.
Most people who come to me already have:
- Concentrated stock
- High income
- Large future liquidity tied to one company or sector
For them, the game isn’t:
“How do I shoot the lights out from here?”
The game is:
- Reducing concentration, not adding more
- Lowering path-dependence and single-company risk
- Cutting tax drag so you keep more of what you already have
- Building a portfolio that’s hard to kill, not just fun to talk about
Risk is invisible right up until it isn’t.
And you don’t get do-overs after a 60–80% drawdown in net worth.
You can still grow.
You just don’t need to live at 300% damage for another round.