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Number 5: Pavel Durov, the Founder Who Flipped Off the Kremlin
Shaan Puri sets the criteria for the list and starts the countdown with Pavel Durov, whom he calls James Bond with Wi-Fi. Durov built VK, the Russian Facebook that beat Facebook at home, then refused the government's request for user data and posted a picture of a dog in a hoodie.
- •Criteria: interesting men who are alive, not just rich or successful
- •VK was the one national Facebook clone Facebook could never beat
- •Durov refused to hand over user data and mocked the request publicly
- •He lost the company and left Russia, but kept about $300 million from the sale
- •He says he would do it all again
Telegram, Durov's Lifestyle and His San Francisco Fight
Shaan and Sam discuss how Durov's brother helped create the encrypted protocol behind Telegram. They cover its billion users, tiny 30-person team and unusual hiring, plus Durov's Dubai base, his flexing Instagram and the story of fighting off muggers in San Francisco.
- •Telegram has about a billion users, no ads and no outside equity
- •About 30 employees; Durov recruits through engineering contests
- •Telegram says it has no office, staff or servers in Russia
- •Durov says he owns no jets, yachts or mega mansions
- •He posted his bloody knuckles after being mugged near the Twitter office
How Telegram Makes Money and Why Durov Refuses Investors
After a sponsor break, Sam asks how Telegram earns money. Shaan describes donations, a billion-dollar debt bond, turned-down offers to buy 10% of the company at $30 billion and $40 billion valuations, and a crypto token that the SEC shut down.
- •Telegram has reportedly taken in over a billion dollars in donations
- •A billion-dollar bond works like a pre-IPO coupon
- •Durov turned down 10% sale offers at $30B and $40B valuations
- •The token raised over a billion dollars before the SEC objected, and he returned money
Number 4: Oleg Tinkov, the Russian Richard Branson
Sam presents Oleg Tinkov, who grew up in a mining family and started out selling Western jeans in the late Soviet Union. His next ventures were a ravioli business with a provocative ad campaign and a premium microbrewery that he sold for $200 million.
- •Tinkov began by importing and selling blue jeans and Western goods
- •He sold that business for around $7 million and started a ravioli company
- •The ravioli ad featured a bare backside and the line about not being made by your grandmother
- •Tinkoff breweries went from 1997 to a $200 million sale in 2005
- •He travels to America every five years to find ideas to bring home
Tinkoff Bank, Defying Putin and Tinkov's Pranks
Sam explains how Tinkov launched a credit-card bank after a talk with Richard Branson, and how it grew into a huge digital bank. After he spoke out against the war, the bank was delisted and he lost most of his fortune. Sam also covers his fake encyclopedia trick, his cycling team and his leukemia.
- •Tinkoff Bank was founded in 2005 with $70M of his own money, branchless and online
- •His stake was once worth about $10 billion
- •He criticized Putin and the war, the bank was delisted and he kept about $200 million
- •He faked an encyclopedia entry to get a street named after his brewery
- •He is donating what is left of his fortune to leukemia
Exporting Culture as a Business Blueprint
After a Beehiiv sponsor plug, Shaan says he had never heard of Oleg. He reflects on observing one culture and exporting it to another as a model for big businesses, and Sam adds that Tinkov studied at Berkeley. They note that both of their picks so far are Russian expats.
- •Shaan had never heard of Tinkov
- •Exporting cultural ideas from one country to another is a repeatable business model
- •Tinkov studied business at Berkeley and drew ideas from the Bay Area
- •Both hosts picked Russian expats by coincidence
Number 3: Sean Parker, the Walking Middle Finger
Shaan introduces Sean Parker, who says he is not the smooth character from The Social Network. He was tracked down by the FBI at 16 for hacking and then created Napster. Shaan uses Kevin VanTrump's idea that the train comes back around to explain Parker's later career as an investor in Facebook and Spotify.
- •Parker says he is weird and eccentric, not the movie's cool version
- •He turned down a CIA job offer after being caught hacking as a teen
- •Napster was an illegal music-sharing service that was sued out of existence
- •Parker made his fortune by recognizing the next Sean Parker, such as Zuckerberg and Daniel Ek
Parker's Wedding, Philanthropy and Facebook Stake
Shaan describes Parker's lavish Big Sur wedding, with its immersive theater and fines, and his onion-baked ring. He then covers Parker's venture-style approach to funding cancer research and how he brought Peter Thiel's money to Facebook, ending with about 4% ownership.
- •The wedding cost an estimated $5–10 million and drew millions in fines
- •He proposed with a ring baked into an onion
- •He bought a $55 million LA house from Ellen DeGeneres
- •He funds unorthodox cancer treatments like a venture capitalist
- •He connected Zuckerberg to Peter Thiel and ended up with about 4% of Facebook
Parker's Spotify Email and the Painter Who Took Facebook Stock
Shaan reads Parker's cold email to the Spotify founders and notes he led a $15 million investment. He then retells David Choe's Howard Stern interview, in which Choe says he took Facebook stock instead of $60,000 because of Parker's confidence.
- •Parker emailed Spotify's founders in 2009 praising their product and pitching a Facebook partnership
- •He led a $15 million investment in Spotify
- •Choe did not like social networks, college or Harvard
- •He took stock because he sized up Parker and thought he was going somewhere
Opportunity Zones and Parker's Political Side
Sam asks about the rest of Parker's career. Shaan lists Plaxo, Airtime and Founders Fund. Sam and Shaan then say opportunity zones were Parker's idea, which he lobbied the government to create to reduce capital gains on his tech stock fortune.
- •Parker's ventures included failures such as Plaxo and Airtime
- •He was a managing partner at Founders Fund
- •Parker lobbied for opportunity zones to incentivize investment in underserved areas
- •Sam says he may also have played a hand in Obama's election
Number 2: Tom Anderson, the Guy Who Won and Walked Away
Shaan presents Tom from MySpace, who hacked Chase Bank at 14 as Lord Flathead and set off a 40-person FBI raid. He later built MySpace, sold it for $580 million, and left rather than tackling bigger goals. He took up traveling and photography instead.
- •At 14 he got root access to Chase Bank and bragged to friends, prompting a coordinated FBI raid
- •The FBI did not charge him because he was 14
- •MySpace sold to News Corp for $580 million
- •He left because of budget reviews and process, then took up photography
- •His Instagram bio lists surfing, architecture, photography and golf
Tom's Second Act and Knowing When You Have Enough
Shaan says Tom became a famous photographer and then stopped posting after someone stole his cameras in Thailand. The hosts discuss his ability to have enough, rumors of his relaxed life in Hawaii, and how good he looks without extreme biohacking.
- •Tom's Instagram has almost 700,000 followers but his last post was about 300 weeks ago
- •He stopped after his cameras were stolen while traveling
- •Reddit sightings suggest he is relaxed and swimming in Hawaii
- •He looks young without a biohacking regimen
Number 1: Vivi Nevo, the Israeli Great Gatsby
Sam presents Vivi Nevo, who resembles Sting and appears in photos at the Allen & Co. conference. He was born in Romania, moved to Israel and Los Angeles, and vanished for years before returning with a new persona. He has celebrity friends and expensive homes, and the media reports huge stakes in major companies, though no one knows how he made his money.
- •Reportedly the largest shareholder in Time Warner and a large Goldman shareholder
- •A former boss described him as charming but doing no real work, then disappearing for years
- •He came back wealthy and well-connected, with Malibu homes, art and famous friends
- •Sam theorizes he built wealth by connecting people and taking small equity stakes
- •Some rumors say he is linked to the Mossad
Mystery Doubts, Photo Analysis and Wrapping Up the List
Shaan questions whether Nevo's story adds up, comparing the mystery to Eric Weinstein's comments on Jeffrey Epstein. The hosts joke about reading into photos of him biking beside walkers and wanting more information. They close by calling the list the most interesting billionaires you've never heard of.
- •Shaan questions how a modest inheritance became such large stakes
- •He compares the mystery to Eric Weinstein's account of meeting Epstein
- •The bike photo at Allen & Co. amuses both hosts
- •They admit they know little and invite listeners to share information
- •They conclude the list is of interesting billionaires you've never heard of
