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Tesla, TSLA & the Investment World: the Perpetual Investors' Roundtable

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Possibly $5,000-$8,000 by end of next month if S&P reduces float like I expect it to

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TSLA has been 100% of my stock portfolio since 2013. I've been an uber-long and have held through the nastiest of TSLA drops and have never played with options.

I only have 2 regrets:

1. I should've gone in more at the beginning and stuck even harder with my conviction.
2. I shouldn't have held through the Q1 and COVID drops.

Had I chosen (1), I'd be a multi-millionaire right now.
Had I chosen (2), I'd be a multi-millionaire right now.

Instead, despite being one of Tesla's earlier customers (Model S 1653) and a die-hard long, I'm still a few hundred grand short of $1M. I really feel left out when some of you say you only bought a year ago and have now pulled in a couple million! Haha don't I get some sort of consolation prize for being an uber-long? :)

Glass half-empty:
I could have cashed out when we hit $420.

Glass completely empty:
I could have been a TSLA short.

Glass completely empty and broken:
I could be a highly public TSLA short with public pictures of me brushing my teeth on the toilet with a laptop.

The long wait for my Model 3 reservation was what got me hooked on to TMC and while here I stumbled on to the investor thread, Thanks to the wisdom from all the folk here such as yourself I started investing in TSLA mid 2017. I started buying in the 300 range and kept adding all the way down to the 180's. Like youself, my position in TSLA is a few hundred grand short of $1M but I think I am OK with it as I was not comfortable placing all my eggs in one basket regardless of my conviction level on TSLA. I think the Elon is the main reason for Tesla's success but he is also the biggest risk to Tesla as the "key person risk". This is what gives me pause from having more exposure to TSLA. Unless he can grow more leaders like Jerome under him I will stick to my current position and let it grow.
 
Do you work a day job and have withholdings deducted from your paychecks? If so, look into safe harbor rules for the IRS and your state taxes with respect to estimated tax payments and windfalls. (For example, if memory serves correctly in California you have safe harbor from quarterly estimated tax payments if you make below a certain amount per year and your withholdings are at least 100% of the prior year's withholdings. I believe IRS rules are similar.)

You may want to consult a tax advisor.
Yep, I do work a day job and I"m aware of the safe harbor rule. I don't pay a state income tax in WA which is nice. I would like ideally pay nothing as my AGI last year was under $150,000 which is one of the few stipulations of safe harbor besides working your day job and having your income withheld every paycheck.

However, I would like to ask a tax advisor to be certain. Does anyone here have any recommendations for tax advice?
 
To the many posters thinking about quitting. It is safe to quit whwn you are able to convert the winning into steady low risk investments that spills out income. When these income reaches 2x your current salary. It then makes perfect sense to quit.

For me thus transition took 3 years as you need to factor in the tax hit and think deep about the portfolio's composition.


To expand on this into a math formula. Assuming that the eventual ROI of your investment properties are 5%.

X= current income that equates to good enough lifestyle
Y= TSLA stock sale Profit after tax

Y = 2*X*100/5