❝Story04:30
Working for the Indonesian coal baron who couldn't read or write
Out of Duke, Shaan took a $120,000 job in Indonesia working for a man he calls Kokos, a second-grade dropout who spoke almost no English and could neither read nor type. Four assistants sat in his office with giant screens displaying his inbox, reading emails aloud while he paced and dictated replies. His business was a deliberate arbitrage: US majors like ExxonMobil, BP and ConocoPhillips wanted Indonesian coal rights, but the auction process was captured locally, so he bribed officials to secure the leases himself. He bought roughly $2 million of coal rights and sold the pieces at around $20 million each, amassing about $500 million in three years. Shaan's job was to be the English speaker who ran the presentations. Kokos was later jailed and died in prison of cancer.
- Kokos amassed roughly $500 million in three years from a $2 million position in coal leases.
- He was functionally illiterate and ran his entire inbox through four assistants reading aloud.
- He refused to test the coal himself, reasoning that the buyers would test it and testing only added risk.
- He held everything through 72 shell companies tracked in one woman's filing cabinet.
- Shaan's read: he was bold and willing to cheat, but playing by the unspoken street rules of that market.
“He bought up for $2 million total this huge amount of coal and then he sold each piece for 20 million. And he amassed $500…”
“He was just bold and willing to cheat and lie and steal. And he wasn't cheating, he was just playing a game. That's how business…”
#arbitrage#founder-story#emerging-markets#risk
❝Story11:30
The WordPress blog that did nothing for the sushi business and changed everything else
While running the sushi cloud kitchen, Shaan and his friends kept a WordPress blog they wrote largely for their own amusement, nominally to help the sushi business. It did not help the sushi business at all. What it did was convert anyone who found it into a supporter who decided these guys were good hustlers. Shaan's father mentioned it in passing to an Australian entrepreneur, Nathan Mitchell, who had just sold his family drilling company for around $450 million and was under a non-compete looking for his next thing. Mitchell read the blog, flew them to Australia, and hired them into a biotech venture on the explicit reasoning that his smart engineers would be too academic without hustlers alongside them.
- The blog produced zero measurable benefit for the business it was supposedly serving.
- Its actual function was signalling: readers concluded they were entertaining hustlers worth backing.
- A $450 million exited founder read it and offered them jobs on that basis.
- Mitchell's stated logic was that engineers alone would make the venture too academic.
- This is the second time a billionaire effectively handed Shaan a playground to run.
“It didn't help the sushi thing at all, but what it did do was anybody who found that really got behind us. They kind of…”
“I got a bunch of like smart engineers, but this will be so academic unless we get some hustlers. You guys are hustlers. Join me…”
#content#personal-brand#serendipity#founder-story
❝Story13:30
The Stripe job he blew, and the $10-20 million it probably cost
Moving from Australia to Silicon Valley in early 2012, Shaan applied to exactly two places: Stripe, then around 30 employees, and Monkey Inferno. He believed Stripe would win because he was deep in Paul Graham essays and Y Combinator founder interviews and considered himself a bet-on-the-person investor. He never spoke to the founders. He had one interview, with a man named Ben, backed by the strongest possible warm introduction through a shared mentor, and he blew it. Running the numbers later, he estimates a biz dev manager seat at that stage would have vested out to roughly $10 to $20 million. Sam thinks Shaan specifically would have fit well there, contrary to the common response that he would have been fired.
- Shaan applied to only two companies on arriving in Silicon Valley: Stripe and Monkey Inferno.
- Stripe was roughly 30 people in early 2012.
- He estimates the foregone equity at $10-20 million, with caveats about vesting and promotion.
- His conviction came from Paul Graham essays and watching YC founder interviews, not from talking to the founders.
- His counterfactual: less money, but a position from which he could do more.
“So if I joined even as just like a biz dev manager or something like that I probably would have made like 10 or 20…”
“I only applied to Stripe cuz I thought that was going to be a winner, but it still would have been lucky that it got…”
#career-bets#equity#counterfactual#silicon-valley
❝Story35:30
The high school Fortnite league that became the Twitch acquisition
After pivot upon pivot, Monkey Inferno landed on youth e-sports. The observation was that youth sports leagues are a large, well-established market with league dues, but there was no youth e-sports equivalent: only pros, no amateurs, despite more people playing Fortnite worldwide than played basketball. Reusing streaming and gaming technology they had already built, they shipped an app where any high schooler could sign up, form a team, invite friends, compete against other teams, get ranked and play tournaments, with everything streamed so it became a spectator sport. Six to nine months into that version it had roughly 10,000 to 25,000 active players and was the biggest e-sports league, though small in absolute terms. Amazon bought the company via Twitch and Shaan stayed two years.
- The gap: youth sports leagues exist everywhere, youth e-sports did not.
- More people played Fortnite worldwide than played basketball, yet only pro competition existed.
- They reused existing streaming and gaming tech rather than building from scratch.
- 10,000-25,000 active players within six to nine months, the biggest e-sports league at the time.
- Streaming every match turned the product into a spectator sport.
“There were more people that played Fortnite in the world than played basketball. And so we were like, that's crazy. This has more players, but…”
“It was the biggest e-sports league, but it was small overall. It maybe had 10 to 25,000 players, active players at the time.”
#esports#product-market-fit#pivot#acquisition
❝Story1:09:30
Blab hit 4 million users and died of leaky retention
Four years into Monkey Inferno, Blab looked like the win. It was essentially what Clubhouse later became, it felt new and fresh rather than another Snapchat clone, it grew to 200,000 users quickly, then a million, and Founders Fund wanted to invest. Then growth flattened at around four million. Signups were still climbing, but retention had started merely okay and was getting worse and worse, so the product was leaking users as fast as it acquired them. Shaan's framing is that retention is the thing worth anything in a business and also the hardest thing to fix, because acquisition is cosmetic and coachable, like getting someone's number, while retention is fundamental, like whether they will marry you. They tried many fixes and nothing moved, because the real question was whether this was something people wanted to do all the time.
- Blab reached 200,000 users quickly, then a million, then stalled around four million.
- Founders Fund wanted to invest at the peak.
- Signups kept rising while retention degraded, making the product structurally leaky.
- Acquisition problems are cosmetic and fixable; retention problems are fundamental.
- Notification spam cannot manufacture retention for a product people don't want habitually.
“Retention is the thing that's worth anything in business. And retention is the thing that's also the hardest to solve.”
“You can go get their number. But you can't make them date you. You can't make them marry you and that's what retention is. It's…”
#retention#growth#product-failure#metrics
❝Story1:11:30
Sam's biggest mistake: selling The Hustle before he believed his own maths
Sam started The Hustle intending to hit $100 million in revenue before year ten, and sold it in year four or five at around $20 million in annual sales, roughly on track. He could show the arithmetic to anyone: take a 10,000-person email list to five million, note that each advertising seller closes about $1.5 million a year, hire a hundred of them, and the numbers reach $100 million. People dismissed email as a hobby and Shaan himself told him to do Facebook video, Snapchat and Instagram instead. Sam's diagnosis is that he could convince everyone else but never entirely convinced himself, so when a decent offer arrived he took it to secure the bag. Morning Brew, a year older, is now around $80 million in sales, and its founder Austin has told Sam that The Hustle would have got there too, and would have been better positioned because it had subscription revenue.
- Sam's original goal was $100 million in revenue before year ten; he sold at year four or five.
- The Hustle was doing roughly $20 million in sales in the year it sold.
- His model: grow the list to 5 million, each ad seller closes $1.5 million, hire 100 of them.
- Morning Brew, a year older, is now around $80 million in sales.
- Austin told Sam The Hustle would have got there, and better, because of subscription revenue.
“I didn't truly believe my own prediction even though I knew this list lines up. I could tell everybody else but telling yourself in your…”
“I sold right when I got a pretty decent offer because I wanted to secure the bag but in reality I could have achieved my…”
#exit-regret#newsletters#conviction#media