Peter Thiel

Peter Thiel's decade-long revenge that bankrupted Gawker

Sam recounts how Peter Thiel, outed as gay by Gawker, plotted for ~10 years with two staffers sniffing for an infraction, then funded Hulk Hogan's sex-tape lawsuit to put Gawker out of business. The lesson: this is litigation finance in action.

“So Peter Thiel is like Powerful VC. He's gay. He didn't want anyone to know he's gay. Gawker wrote an article saying he's gay. And so he plotted for 10, 15 years, probably 10 years. He goes, whenever I see these guys slip, I'm pouncing.”

The strategy too stupid to sell: just buy FANG and hold

Shaan relays Peter Thiel's point that simply buying FANG (Facebook, Amazon, Netflix, Google) in 2013 and holding would have 6x'd your money and beaten almost any money manager — but advisors can't recommend it because it's too simple to justify their 1% fee.

“if you had just put your money into FANG, which were obviously great companies that were technology companies that were growing, and you didn't even need to know how fast they were growing, but if you just said, these are solid companies that, you know, seems like everybody in America is using their products, you would have made 6 times your money in the last 8 years. And he goes, that would beat the performance of almost any money manager or hedge fund or investment banker that you're thinking of working with.”

Steal thisDefault to the embarrassingly simple buy-and-hold strategy; complexity in investing usually underperforms.

Peter Thiel's one-line advice after investing in Airbnb: don't fuck up the culture

Shaan recounts that when Peter Thiel put roughly $100 million into Airbnb in 2012, the founders asked his single most important piece of advice. Thiel replied with a one-line email: 'don't fuck up the culture.'

“That's like when Peter Thiel invested in Airbnb, I think he put like $100 million in or something like that. And this was back in 2012 where Airbnb wasn't super proven out. We're so glad to have you on board. You know, you invested in Facebook early on. You know, what's the single most important piece of advice you could give us? He just wrote back a one-line email that just said, don't fuck up the culture.”

Peter Thiel's $500K Facebook bet grew tax-deferred in a retirement account

Sam recounts that Thiel invested his early $500K Facebook stake through a retirement account (later clarified as a self-directed IRA), so the enormous gains grew tax-deferred. Erb explains assets inside a retirement plan aren't taxed until withdrawn, and people now do this with crypto, gold, art, and real estate.

“He was the former founder of PayPal. And that his investment— he put $500K into Facebook and he put it in through like an IRA or something like that. Like he's been investing out of a retirement account so that his gains in Facebook were tax-free, essentially.”

Steal thisHold rapidly appreciating assets inside a self-directed IRA so growth compounds tax-deferred until withdrawal.

Know what business you're really in (Thiel: Harvard sells credentials, not education)

Shaan uses Thiel's point that universities are in the credentialing/insurance business, not education (a better curriculum won't beat Harvard). He learned this firsthand: his dating app failed because dating apps are really in the business of local customer acquisition within a 20-mile radius, not UX.

“Why? Because what business are they really in? They're in the credentialing business. They're in the insurance business of, hey, this insurance policy for your kid. If you get a degree, you're going to have a job.”

Steal thisBefore competing, identify the real business you're in (acquisition, credentialing, real estate) and win there.

Buddy Media: seed at $4M, sold to Salesforce for ~$700-800M

Altucher was an early investor in Buddy Media alongside Peter Thiel, with Mark Pincus also in the seed round at a $4M valuation. Salesforce later acquired it for roughly $700-800M.

“we all were the seed investors at a $4 million valuation that sold to Salesforce for about $700 or $800 million.”

Be the dumbest investor: only co-invest with people smarter than you

Altucher's most successful investing rule is to only put money into deals where someone far smarter (like Peter Thiel in Buddy Media) is investing on the same terms, outsourcing all due diligence to them. The corollary: if a founder ever calls him for advice, he marks the investment as zero.

“than me says, hey, I'm investing in this company, I don't even have to do any more work. I just send the check. 'Cause I assume, and I'm always correct when I assume this, he's done or she's done all the due diligence. All the hard work.”

Steal thisCo-invest only when a far-smarter lead is in on the same terms; treat an advice request from the founder as a sell signal.