Fact
Even Sequoia has a graveyard: social bets are nearly impossible to call early
Jack Smith's point, via Shaan: even Sequoia, who led every WhatsApp round into a ~$19-20B exit, also funded social flops like Yik Yak and Whisper. If the best investors swing and miss this much on social, predicting a social hit before it plays out is essentially impossible.
“if even the best guys who have had the home runs have a bunch of swings and misses with social, it just shows how hard it is to correctly predict social before it plays out.”
Fact
A SPAC is a unicorn mating dance
Shaan explains Ackman's framing of a SPAC: a public shell that already holds $5B in the bank looking for one elite private company to merge with and take public. The acquisition itself signals to the market, like Sequoia investing, that this is the company to buy.
“And what he says, he goes, it's like a unicorn mating dance. He goes, we're a unicorn because we raised $5 billion. We have that money in our bank. And we're just looking for a unicorn to mate with, a private company who is really special, really defensible, has awesome revenues, long-term, but everything you would want in a company”
Number
Sacca's Lowercase fund returned 225x: $100K became $22M
Shaan notes a great VC fund returns ~5x and Sequoia's top funds maybe 9-10x, but Chris Sacca's Lowercase Capital (Uber, Instagram, Twitter, Docker) returned over 225x, meaning $100K in became $22 million out.
$225
Fund return multiple (Lowercase Capital) · x
“So this one returned over 225x. So, like, you know, you put in $100K, you got $22 million out.”
Story
A startup raised $8M copying the org-chart idea from the show
After Shaan and guest Daniel Gross brainstormed a public, crowdsourced org-chart tool on the pod, a stealth startup called The Org launched doing exactly that and raised $8M from Sequoia and Founders Fund.
“There's actually a startup that came out of Stealth that is doing this after we talked about it. Clearly stole our idea. It's called The Org. They raised $8 million from Sequoia and Founders Fund, and it looks like they're doing exactly this.”
Framework
Sequoia's rule: when the industry changes, that's when you run
Bradford recalls Sequoia's number-one rule from her time there: the moment consumer behavior shifts, big regulations change, or technology turns a corner is exactly when entrepreneurs should start running, because that's where the gold rush opens.
“when things change in the industry, industry, when, you know, consumer behavior shifts or like huge regulations shift or technology changes, turn a corner, that's when, that's when you all need to start running. And that's, you know, that's why the gold rush is called the gold rush.”
Steal thisWatch for shifts in consumer behavior, regulation, or technology and move fast when one turns a corner.
Tactic
Become the #1 user of a brand-new platform
Jack's playbook if starting over at 20: spot a just-launched platform like Product Hunt early (under 200 users), post daily until you're the #1 user, automate it with a cheap script, then leverage the leaderboard visibility—Sequoia partners and startups came to him because he was prominent there.
“I saw Product Hunt. It launched, had, I think, under 200 views or something. I was like, oh, this just seems pretty interesting. And then I just started using it every single day. I just would post new products to it every single day. So, you know, a few minutes of work each day. And then quickly, I just became the number one user on the site, and they had like a ranking board.”
Steal thisFind a new platform with a leaderboard, become its #1 user through daily consistency (automate it), and convert the visibility into connections and deal flow.