Can Elon Musk Use The Same Mark Cuban Playbook 🧵 👇

I had dinner with some Asian VCs. They talked about the possibility of Elon using the same stunt as Mark.
I told them it is not possible, but they insist it is possible. No need to argue with them. I put it on X to share with all. You decide.
Here are 20 pointers:
1/ Can an insider like Elon Musk short the market using locked-up shares?
2/ The short answer is no. Brokers can’t lend out locked shares to short sellers.
3/ But Wall Street has always found a back door through financial engineering.
4/ In 1999, Mark Cuban pulled off the ultimate hedge using this exact dilemma.
5/ He sold Broadcast to Yahoo! for $5.7 billion in stock.
6/ The catch? All of his Yahoo! shares were strictly locked up.
7/ He knew the dot-com bubble was going to burst and needed a way out.
8/ He couldn't sell or short Yahoo! directly without breaking SEC laws.
9/ So, Cuban found a massive loophole in the regulatory rulebook.
10/ He couldn't short Yahoo!, but he could short an internet index.
11/ As long as Yahoo! made up less than 5% of that index, it was legal.
12/ He spent millions shorting the index to hedge his downside risk.
13/ Once his lock-up expired, he executed his famous "Zero-Cost Collar."
14/ He bought put options to guarantee a floor price if the stock crashed.
15/ He sold call options to fund those puts, costing him $0 out of pocket.
16/ When the dot-com bubble burst, Yahoo! cratered, but Cuban was protected.
17/ Fast forward to today: Could Elon Musk run the exact same play?
18/ Not quite—modern SEC laws and corporate governance are way stricter.
19/ Tesla's strict anti-hedging policies explicitly ban insiders from buying puts.
20/ Today, Elon’s only legal move is "macro shorting" the broader Nasdaq index.
If I am Elon, I will do this:
The Clean Workaround: Macro Shorting
If Elon wanted to hedge against a broader market crash or an EV sector downturn while his shares were locked, he could legally short unrelated assets or macro indices (such as shorting the Nasdaq-100 or buying puts on the S&P 500).
Because his net worth is tied up in highly volatile equity, buying broad-market puts or shorting a macro index serves as a synthetic insurance policy. If the macro economy tanks, his tech stocks drop, but his index shorts offset the bleeding, exactly like Cuban’s initial index play.