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Re:The Boring Company raises $112M from Musk, early employees by tc313 on Monday April 16, 2018 @10:08PM (#16854843)
You’re talking about buying puts, which is different from shorting the stock. If you short a stock that stays flat, you’re out your borrowing costs but nothing more.
Re:The Boring Company raises $112M from Musk, early employees by prklmn on Monday April 16, 2018 @10:18PM (#16854907)
Also you could have sold long dated call spreads for most of the year - effectively shorting the stock with some profit to show for it.

Edit: you’re also more likely to have lost money buying Tesla over the past year vs shorting it, so it really hasn’t been “expensive” to short it.