Chris Sacca

Rehearse your stories like a comedian who's never told the joke before

Shaan recounts watching investor Chris Sacca deliver the same offhand 'I didn't realize at the time' lines identically in person and on CNBC. The lesson: craft your best stories once, then perform them repeatedly as if it's the first time, like a comedian or a Broadway actor.

“I saw him on CNBC one day and he said the same fucking thing the exact same fucking way, like a comedian does in their sets. Where a comedian, if you go up there and it feels like a comedian has said this joke a million times and they're bored of it, then it's not funny. But a comedian has to sort of like it's almost like they're realizing or telling this story for the first time. That's when it really hits.”

Steal thisBank your best stories and lines, then deliver them every time as if it's the first time you've ever said them.

Chris Sacca went all-in on Twitter before it was even his company

Shaan recounts Chris Sacca's playbook: after a small early check into what became Twitter, Sacca saw it was a winner and went all-in, showing up at the office, fundraising for a company he wasn't part of, and buying billions in stock pre-IPO to become a top shareholder.

“He quit his job, basically started showing up at the office every day being like, how are we going to make this thing grow? I want this thing to grow. He went and personally was fundraising for the company, even though he wasn't even a part of the company. But he was out there pitching investors to invest in Twitter, and then he ended up buying billions of dollars of Twitter stock before it went IPO”

Steal thisPlace small bets early, but when one clearly works, follow on hard and go all-in.

How Chris Sacca turned a $25K Twitter bet into billions

Shaan recounts Chris Sacca angel-investing $25K into Ev Williams' startup that became Twitter, then aggressively buying employee shares whenever someone needed cash (e.g. to pay for a wedding), accumulating 10-15% of the company by IPO and becoming a billionaire.

“Anytime there was an opportunity to get shares in Twitter, he took it. Some employee is leaving the company, he's like, hey, I'll buy your shares. Somebody needed to pay for a wedding, he's like, cool, let me buy some of your shares and then you get some money for your wedding. And he over time accumulated this huge position in Twitter, like I think 10-15% of the company by the time it IPO'd, and it made him a billionaire because of how big of a position he had accumulated.”

Chris Sacca day-traded $20K to $1M, then crashed to owing $4M

Shaan tells the Chris Sacca origin story: as a law student skipping class, he day-traded ~$20,000 up to about $1M during the dot-com boom, levered up with family money, then swung to owing $4 million when the market crashed. He refused bankruptcy, negotiated the debt down to $2M, and hustled to pay it off.

“Starts day trading, runs up like a small amount of money, like let's call it $20,000 into basically like a million bucks. And he's, you know, so he's making these— he's doing day trading. He took some money from family and friends to kind of lever up even more. And so stock market crashes and he swings from, you know, up a million or $2 million to down $4 million. He owes $4 million and he's a law school student who's like got zero to his name”

Chris Sacca raised SPVs to buy secondary Twitter stock, ended up the top holder

Shaan describes how Sacca, believing the market had mispriced Twitter, raised single-deal special purpose vehicles to buy secondary stock from employees cashing out. By IPO he held roughly 8-10% of Twitter, a billion-dollar-plus stake, anchoring what Shaan calls the greatest early-stage fund ever.

“So he starts creating these SPVs, special purpose vehicles, which really just means it's a fund just for one deal. It's not like an ongoing investment fund where we trust you, Chris Sacca, to invest in 25 companies. It's like, "Hey, I have access to this Twitter deal. Let's buy some Twitter stock. I need to raise money to buy Twitter stock." He was just buying secondary.”

Steal thisSpot a mispriced winner, then raise single-deal SPVs to buy as much secondary stock as you can.

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.

“So this one returned over 225x. So, like, you know, you put in $100K, you got $22 million out.”

Fast Grants: YC-style science funding decided in under 48 hours

Shaan describes Fast Grants (created by Stripe's Patrick/John Collison), which fixes the slow science-grant system by making a $10K-$500K funding decision in under 48 hours, wired immediately. Backers include Paul Graham, Reid Hoffman, Chris Sacca, and Elon Musk, with over $15M committed.

“So Fast Grant is basically a $10,000 to $500,000 decision made in under 48 hours. If you approve the grant, if the grant is approved, you receive the payment as quickly as can be wired to your account. Now, and so they have the Carlson brothers behind it. They have Paul Graham, Reid Hoffman, Chris Sacca, Elon Musk, a whole bunch of different people. So they have— they've committed over $15 million already in fast grants.”

Chris Sacca: 'I've never felt richer than when I had $0 net worth'

Shaan recounts how Chris Sacca levered his way up to a paper $12 million, swung down to negative $4 million in a week, and clawed back — saying he never felt richer than when he climbed out of debt back to zero. He's now a billionaire with Uber, Instagram, and Kickstarter in his portfolio.

“And he has this great line, which you remind me of, which was, I've never felt richer than when I had $0 of net worth. Like when he got out of the debt and got back to zero, he's like, I've never felt richer.”

Travis Kalanick was ranked #2 in the world at Wii Tennis while running Uber

Chris Sacca tells how, while CEO of Uber, Travis Kalanick hustled Sacca's dad at Wii Tennis — playing left-handed, then switching hands ('I'm not actually right-handed') — and was ranked #2 globally. Sam uses it to show competition is Kalanick's fuel.

“And later in that story, Chris actually says that he did the same thing with Angry Birds. He was ranked really high with that. But this is just how he's always been.”