A short segment where Sam and Shaan share their worst and best investments. Shaan’s worst: not writing a $25K angel check into an international student admissions SaaS company that became a unicorn (would have been worth ~$5M). His other worst: buying MGM put options on Robin Hood while simultaneously watching a Khan Academy video explaining what a put option is. Best: buying Bitcoin at $4,500.
Speakers: Sam Parr (host), Shaan Puri (host)
Note on This Episode
This is a short standalone segment — likely a clip or bonus episode rather than a full episode. Runtime is approximately 10 minutes. Recorded during COVID (references market volatility, PPP loans, unemployment claims).
Shaan’s Shitty Investments [00:00:00]
Shaan: Two bad investments and one good one.
Shaan: Bad investment number one: a startup I was advising. A guy building an international student admissions tool — software that helps students overseas apply to US universities. If you live in China, India, or Malaysia, getting into a US university is the life goal. Universities overcharge these students dramatically. This founder matched supply and demand: a free SaaS tool for the student, and the university pays thousands of dollars per accepted applicant. Great business.
Shaan: I’d been advising him for four or five years. I was very close to writing a $25,000 first check. I talked myself out of it: you need 25-30 bets to do startups properly, and $25K times 30 bets is $750K, and at the time that would have been most of my net worth. So I passed.
Shaan: That company just crossed a billion-dollar valuation. My $25,000 would be worth roughly $5 million today.
Sam: You’ve lost $5 million.
Shaan: I didn’t exactly lose $5 million, but I did not make $5 million that I could have made. This has happened to me twice now — two angel checks I almost wrote, both of which would have been worth millions. The excuse each time was reasonable. The excuse was also wrong.
Shaan: Bad investment number two: COVID options trading. During COVID, MGM Resorts had dropped from around $30 to $12. I figured it had further to fall. So I had Robin Hood open on one tab and a Khan Academy video explaining “What is a put option?” on the other tab — simultaneously. Just pushing buttons.
Shaan: I placed about $2,000 worth of options. After the trade confirmed, I actually read the confirmation and realized I had bet that MGM would drop 40% in the next seven days. That’s not what I thought I was doing. MGM didn’t drop. I lost the $2,000.
Sam: That is so impressively bad.
Shaan: Best investment: I bought Bitcoin at around $4,500 during the COVID dip. That one made back the option losses many times over.
Sam’s COVID Market Moment [00:07:00]
Sam: My version: I sold most of my equities near the market bottom during COVID. Unemployment numbers were horrific, and I kept thinking: there’s no way the market doesn’t keep falling. It then went up 20% in a week.
Sam: I stay away from stocks entirely now. I only do S&P 500 or a small amount of Facebook stock. I have zero ability to predict short-term market moves and I’ve stopped pretending otherwise.
The Keynesian Beauty Contest [00:09:00]
Shaan: There’s a phrase that explains this: the Keynesian beauty contest. Keynes described the stock market as a beauty contest where you’re not judging the beauty yourself — you’re guessing what the other judges think is beautiful, who are also guessing what the other judges think. It becomes a speculative loop. Nobody’s evaluating the actual business. Everyone’s guessing what everyone else will pay.
Sam: The short version I’ve heard: in the short term the stock market is a popularity contest, in the long term it’s a weighing machine. If there’s nothing real underneath the valuation, eventually it collapses. But in the near term, hype is real and matters.
Shaan: That’s also true for private company fundraising. A Series A at a crazy valuation is a popularity contest. It can hold if the hype compounds. It can’t hold forever if the fundamentals aren’t there.
Sam: I just don’t understand it well enough to play. And the more I learn how little I understand it, the more I want to stay away.