YOLOing My Roth IRA

A few months ago it came out that Peter Thiel turned his initial $2000 investment in a Roth IRA into $5bn (tax free) by yoloing 1.7mm shares of Paypal back in 1999. As an analyst in banking who will surpass the $140k earnings threshold for Roth IRA contributions this year, I think this is potentially a really great strategy. I currently have 6k just sitting in QQQ, but I would much rather be a disgustingly rich 59.5 year old with the potential to lose it all, than a mediocre retiree.

My current thought is to pick 3-5 penny stock names and go all in. That way its a bit more diversification, but still highly concentrated. My question for all of you is: what names look good??? Anyone else want to try this with me??? 

Potential Picks: IDEX, NAKD, INND

27 Comments
 
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Before you go yoloing your money.

First, you should keep in mind that many great innovative tech firms are not IPOing when they are only a $20-$500 Million market cap company. They are IPOing at $10 billion-plus. This is primarily due to PE firms getting more involved with a growth arm. In addition to VCs who have raised valuations as we saw in WeWork. You probably will not find a 1997 Amazon or 1980's AAPL/INTC ever because of later rounds and later exits.

Second, Peter Thiel is a founder of Pay-Pal and even served as CEO for a while if I am not mistaken. This is what primarily differentiates him from you in addition to being a childhood chess prodigy, and Stanford Law School. He could directly control the value of the firm by managing it correctly. He was an "active investor" in the most literal sense. He owned probably 20%-30% of Pay-Pal in the early days and was making operating decisions for the company to succeed.  I doubt $6K will get you any majority ownership of any public company that would allow you to make operating decisions.

Just some things you should probably keep in mind if you are expecting your $6K to turn into anything close to a billion. 

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