I keep beating this drum, but . . . why not just borrow against the assets?
While I am not, by any means, an expert on this topic, I STRONGLY suggest that selling TSLA shares is almost always going to be the very wrong thing to do.
Everyone on this thread should be very well aware that TSLA could be at 2x or 3x in just a few years. This interview by David Lee suggests that Tesla will be the most valuable company
in the world by 2025:
Which begs the question:
Why would anyone wish to sell shares, shares that will be far, far more valuable in the years ahead, when asset-based lending exists? (And I believe/think that's how Elon was funding his lifestyle for many, many years before forced to sell shares due to expiring employment options.)
If you actually sell shares to pay taxes, that tax payment will likely be the most expensive taxes you will ever pay.
Others may chime in with more options here, but I just don't see how what you are planning to do is even remotely a good idea.
p.s. More info on asset-based lending here; others may have additional info:
A portfolio line of credit can be a great way to borrow money at a low interest rate, but there are risks too. Here’s what you should know.
www.bankrate.com