Ask What Could Go Right: Jason Calacanis on Robinhood, Loyalty, and Two Checks for Tesla

Lex Fridman opens on WallStreetBets and GameStop as a historic stress test of power, greed, and who gets to participate in markets. Calacanis answers with a disclosure and a story. He was an angel in Robinhood before launch. He met the founder, Vlad, and his partner at Antonio’s Nut House in Palo Alto, after giving a talk at Founder Institute and being dragged there because Elon Musk was coming for a drink. It is, he says, the worst bar on the peninsula: garbage on the floor, cheap warm beer, lipstick on the glass that is not yours.

Vlad recognized him, which Calacanis took as proof the man had a startup. Vlad said he was a quant. Calacanis’s first jab was the obvious one: if the algorithm printed money, why sell it? That was not the business. The business was an app to get millennials to trade stocks. Calacanis listed the objections in a heap. Retail investors had been wiped out by the dot-com crash and 2008. These were the same people living in their parents’ basements, taking Uber, carrying $250,000 of school debt, and showing no interest in their financial future. And the business model was free.

Vlad’s reply, each time, was that the objections were the opportunity. Calacanis said amen. The crazy ideas nobody believes in, he argues, are the ones with the greatest returns. He had introduced Uber to about 25 investors; three said yes, a 12 percent hit rate. The useful question is not the chance of success. It is what the world looks like if the thing actually works. Tesla, when Musk was trying to save it, was “almost positively not going to work,” and Musk knew that. The bet was the other half of the sentence.

Robinhood, in that frame, asked what a generation would look like if it became fluent in puts, calls, shorts, and research. What arrived was a subreddit and a Discord server acting in unison against insiders with more access and more capital. Most such things fail, Calacanis says, the way Wikipedia was supposed to fail: you are not paying anybody, so how do you build the largest encyclopedia in history? It worked anyway. Then the system around it got stress-tested, and the edge cases showed up.

Calacanis puts GameStop next to Trump’s four years and calls both of them stress tests. Constitutions, higher education, and financial plumbing all look fine until someone finds the edge case. In the market, that case was mathematical: there were more shares short than shares outstanding. He still does not know how that is allowed to exist.

He went looking for a list of who had shorted the stock. There isn’t one. At best you get a lagged report every week or two, with totals and no names. Call a desk to borrow shares and the conversation sounds, he says, like hunting a 1973 Mustang: let me see, I might know a guy who has some to loan. That process, he argues, should live on a public ledger. In a vacuum of information, minds invent conspiracies. Sometimes the conspiracy is real. Sometimes it is the mind filling in.

Robinhood’s actual goal, as he tells it, is to get more people trading. During the squeeze the firm was on the brink as an entity if it could not cover the trades, and it raised something like three and a half billion dollars in a week. Fridman hears Wikipedia in that: a distributed system that should not have worked, then did, and handed a generation the tools to take on centralized players. Calacanis agrees, and adds a warning about velocity. Startups now reach a global footprint in a few years, which means the stress tests arrive before anyone has written the manual.

Airbnb, Calacanis says, should not work in practice: rent your spare room to a stranger, or sleep in a stranger’s house. It did not destroy hotels. It added trips. The pattern he cares about is that the best startups induce a market to exist. Uber was not, in the end, competing with taxis. It was competing with car ownership, public transit, walking, and staying home. People sold their cars. Kyoto is the Airbnb version of the same claim: a $75 room with great reviews for three weeks is why some people take the trip at all.

Robinhood did a version of that for financial literacy. You cannot learn options from videos the way you cannot learn poker, guitar, tennis, or skiing from videos. At some point you get on the mountain and put chips in the pot, and it will be painful. Play the small tables first. The people who threw money at GameStop last, into a company that might be worth a couple of billion and not tens of billions, were going to lose. Everybody knew it was a momentum play against the hedge funds. The education was still, in his view, worth having, if you understand risk of ruin.

For a young person, ruin might be $5,000 and a slow rebuild. What worries him is the subset who cannot stop, the way some people cannot stop at two glasses of wine. You do not design a society around the person who drinks twenty. Fridman asks whether WallStreetBets is a moral uprising against elites or a new chaos engine. Calacanis reaches for *The Dark Knight*: some people just want to see the world burn, and those people live on the forums. The longer arc he expects is mass education, the same appetite for risk he saw when failed founders came back with ICO white papers full of spelling errors and a plan to put apartments on an immutable ledger.

ICO mania, for Calacanis, was proof of a global hunger to try new things, which he files under the human spirit and under capitalism. What concerns him is the opposite mood: entrepreneurship is bad, technology is bad, getting rich is bad. He is 50, a Gen Xer, and he thinks his cohort may have idolized Bill Gates too much, but they at least treated capitalism as a force for good. When a product gets globally distributed — Tesla, SpaceX, Google, Airbnb, Uber, Robinhood — everyone benefits from the competition. Places without competition, he says, including public education and accredited degrees, tend to get “a little weird,” and the people inside them get protected.

That is not an argument against a safety net or health coverage. It is an argument for keeping capitalism vibrant, because China has built a hybrid: communism plus capitalism. “We still want to keep communism so we can take any of your gains at any time,” he says, “but we’d like you to be entrepreneurial.” Jack Ma disappears for a couple of weeks, comes back sorry, disappears again. If China wins capitalism, he calls it an existential threat for humanity. Fridman notes that the surveillance state seems to work in the short term. Calacanis agrees the short-term gains are real, and still wants the American story to make the entrepreneur the hero — the kid with the dream, not a tax debate.

The pernicious group, as he paints it, is not the poor. It is a loud, small slice of privileged urban liberals who claim to protect poor people while not believing those people can change their lot. He tweets that every course from MIT, Harvard, and Stanford sits on edX and Coursera, and the replies arrive on cue: they don’t have internet, they don’t have phones. He posts penetration charts and a $12 or $15 monthly high-speed plan and dares anyone to find the downtrodden person with no smartphone. The average American, he adds, still watches four or five hours of television a day.

Then there is the founder who needs a technical co-founder and a million dollars and has no skill — not design, not product, not code, not sales. “I have an idea.” Sam Harris’s line, which Calacanis repeats, is that everybody spews a million ideas an hour, including while asleep. Ideas get zero credit. Execution is the whole game, and the individual still gets to be the core of that execution. WallStreetBets, in that telling, is evidence that a person can still change a system from the outside.

Advice to young people, from Calacanis, collapses to one meta-skill: get good at learning a new skill. Tim Ferriss is the exhibit. On a group vacation in Italy there was a basketball court. Calacanis has played since Brooklyn; Ferriss, he says, is fabulously uncoordinated, a layup with a blindfold on. Ferriss watched, took notes, checked his form, and in a couple of hours could do it. That, Calacanis claims, is now the path for almost any skill. If you burned 400 hours on *Game of Thrones* and *Breaking Bad*, you could have spent them on graphic design or code.

He did a version of this himself: night school out of Brooklyn, racing to about 50 percent of the knowledge in design, writing, sales, even development. Fifty percent is enough that hired people cannot snow you. Fridman, running a podcast without a big team, is the same pattern. Hours are not the unit that matters. After *The Queen’s Gambit*, Calacanis jumped back into chess, played a lot, and did not improve, because he never reviewed losses. Chess.com’s analysis of blunders changed that. Push it further and you stop playing games at all: endgames, openings, puzzles, $100 a year, opponents matched to your rating 24 hours a day. That, he says, is capitalism and competition creating surplus for a society.

Michael Jordan in *The Last Dance* is the human version of the same thesis, taking everything personally to manufacture motive. Musk took a decade of laughter at electric cars and forced every legacy maker to announce a 2035 electric future. Calacanis wants more of that, including in a pandemic: mRNA had been sitting around, challenge trials in the UK struck him as more reasonable than the rituals we already celebrate — skydiving, free soloing, welding at 200 feet — and a thousand young volunteers at a million dollars each would have been a rounding error next to trillions in stimulus. Crony capitalism and slow regulators, not a failure of the scientific idea, are where he puts the testing kits that other countries had been using since spring.

Fridman asks him to steelman what Robinhood got wrong, given that Calacanis is both a cheerleader for retail power and an early investor. Communication, he says, is always the number one issue in these companies: get ahead of the problem and put the bad news out. The public record, as he reads it, is a liquidity crisis. So many people were trying to buy five shares of a meme stock that the system broke, and the clearinghouses demanded a billion, then two, then three, overnight. You cannot conjure that collateral from the couch.

The bind is that going on television to say you have a liquidity crisis looks like a bank run. Everyone logs in at once to sell every share they own. So Vlad had to be vague, and the vacuum filled with the story that hedge funds had forced the buy button off. Calacanis does not buy that story. He also admits that from the outside, the appearance of impropriety and the real thing are hard to tell apart. Fridman pushes on why some CEOs sound like they are hiding something. Musk on Twitter does not. Zuckerberg often does. Jack Dorsey less so. Nondisclosure agreements, nerves, and being the most hated person on earth for a news cycle can all produce the same tell.

The media script, in his telling, is stable. Uber, Facebook, Tesla Autopilot: new technology fails, and we blame the technology, not the operator. Someone stands on a motorcycle at 60 miles an hour and nobody sues Yamaha. Someone sleeps in a Tesla against every Autopilot rule and Tesla owns it. Airbnb always knew a guest would trash a home. Then a drug party wrecked a woman’s apartment, ripped up her photos, and led every newscast. Hotel rooms in Los Angeles get the same treatment from rock bands throwing televisions out windows, and that is not news, because it is a hotel. Airbnb banned party rentals and learned. The learning curve is now compressed into two, three, four years instead of decades, because the App Store, stored cards, and a supercomputer in every pocket moved the whole market from 60 million broadband homes onto the phone.

The surreal week, as Fridman lists it, included Musk interviewing Vlad on Clubhouse, seven movies sold in two weeks, three and a half billion raised in days, a new president, and, a month earlier, an attack on the Capitol plus Trump banned from the major networks. What still troubles Fridman is Parler coming off AWS. Calacanis says the paranoia is earned. These companies are beholden to the mob; lose the audience, the customers, and the employees, and the person gets canceled. The stack then dropped from the social layer to the infrastructure layer, even to a CDN, which is plumbing. His predicted response is peer-to-peer social and a distributed cloud built from spare hard drives, because closed networks will keep kicking people off and open standards will not.

Will something replace Twitter and Facebook? There will be ten Clubhouses, he says. Friendster was unbeatable, then MySpace hit 100 million users and 100 million in revenue, then Facebook, LinkedIn, Snapchat, FriendFeed. A category usually has twenty winners and the top two or three take 80 percent, and the names change. Facebook without Instagram, he argues, would already be a company in decline; WhatsApp and Instagram saved it. Instagram had just raised $50 million from Sequoia at a $500 million valuation and did not need to sell. Standing alone, he thinks it would be worth hundreds of billions. Zuckerberg, in this portrait, is a marauder with no moral compass, a man who copied Snapchat until the WhatsApp and Instagram founders left, took their billions, backed Telegram, and still said terrible things about him on the way out. “These are the people he made billionaires and they really don’t like him.”

The playbook under that growth is deleting friction. Uber took the credit card out of the car so you get in and get out. Amazon started with one-click. Clubhouse: one click to listen, two clicks to speak; the only faster version is the microphone already on. Unintended consequences arrive at that speed. Facebook’s Groups let friends add you without permission. Someone built a fake NAMBLA group, dropped Zuckerberg, Michael Arrington, Calacanis, and twenty other Valley names into it, and screenshotted the proof. Worse: a college gay men’s choir was added in bulk, the join posted to the wall for engagement, and 18- and 19-year-olds were outed to their families. Growth versus what is right for the person is the crack he wants Silicon Valley to look at, and it is the vision he thinks Zuckerberg does not have.

Great leaders, Calacanis says, are trying to do something that looks like an Olympic sport or a Navy SEAL mission. We do not pity Michael Phelps for 4 a.m. swims and ice baths. He wanted to be the greatest and knew the bill. At work, people conflate “I showed up to pay my bills” with Phelps, Jordan, Musk, or Bezos. The *New York Times* Amazon story interviewed 200 people and described a culture of brutality never seen before. You can also find people who joined out of an MBA, stayed 24 years, and are ride or die. The mismatch is the point. Some people should pick rice, put grain in a basket, and go home. That is valid work. Some people carry a sword. “You cannot conflate the two. You cannot compare the two.” If you are not serious about taking the beach, do not go work for Bezos or Musk.

Work-life balance in a startup, he says, is a ridiculous concept. If you want it, do not go. There are plenty of jobs where you put the round peg in the round hole and take your rice home. What he sees instead is a country that has gotten soft: no Vietnam for Gen X, drone wars, and Americans now dying of suicide, obesity, heart attacks, and anxiety — killing themselves or eating themselves to death, as he puts it. Leadership, when he finally answers Fridman’s earlier question, is setting the bar and living it. Musk, a friend of twenty years, is indefatigable; the stamina infects the team. Bezos likes sharp debate. Jobs bridged gaps in design. Your time as a leader is over when you can no longer set the standard. Bezos at 57, richest on the planet depending on the week, handing off Amazon rather than grinding another 25 years, is the healthy version of that.

If America loses capitalism to China, he says the human species loses. Steven Pinker’s charts look great on poverty, lifespan, science, and growth. One line is flat: the share of people living in democracies peaked around 53 or 54 percent and is now under 50, because democratic countries are not matching authoritarian population growth. The battlefield is science, technology, and finance. He then states his view of Xinjiang in the harshest terms the interview contains — prison camps, cotton, genocide — and says every Jewish person he has asked treats that case as the exception to the rule against Holocaust metaphors. Meanwhile America, in his account, is busy vilifying the entrepreneurs, scientists, educators, and financiers who would have to win the contest. He tells founders to turn Twitter off. It is not a healthy sport.

Calacanis teaches angel investing six times a year, wrote the book *Angel*, and runs what he calls the world’s largest syndicate, 6,500 members. The first deal they ever did was Calm, the meditation app: $378,000 into a $5 million company, six or seven percent, now worth $2 billion. He did it because he asked Sam Harris how meditation worked, Harris pointed him at UCLA’s mindfulness work and Diana Winston, and UCLA people told him Phil Jackson, Kobe Bryant, and Shaquille O’Neal had used it on the way to championships. If UCLA was in and Harris said it was real, he wrote the check. It is the second-biggest outcome of his career after Uber, and may pass it. Nobody else wanted the round.

What you cannot fake, he tells students, is a product built with craft — Calm, Robinhood, Uber, Tesla, Amazon — and customers who are actually delighted. Team, product, customer: three vectors, all required. Plenty of smart teams exist; plenty of them ship something mediocre. The scarce event is the product lighting up a user, which you read as time spent, the industry word being engagement. Snapchat had a fraction of the users and a top third opening the app every hour, a hundred days in a row, which nobody had seen; streaks and ephemeral messages were the hook. Clubhouse raised at a wild valuation on the same signal: hours per month that did not look real. Reverse-chronological feeds used to feel fresh. Then Facebook, with Dave Morin in the story as Calacanis tells it, learned to surface whatever had already earned likes and comments. Outrage, cancellation, and Trump’s Howard Stern instincts became the ranking function, and the human mind was asked to process more suffering than it was built for.

Should a startup take venture money? Sub-one percent of American firms get it, maybe ten basis points. It is jet fuel. You take it only if you want to build something big, fast, and you accept that rockets explode. Seven of ten companies he backs go to zero. Grow 10 percent a year on customer revenue and you are on a bicycle: you will not die, and you will not go that fast. A $300 million fund writes thirty $10 million checks and needs one or two names to return three times the fund, which means a 30x on a single company just to get whole, 60x to double it, against a 25 percent annualized target that is supposed to triple cash in a decade. The founder is trying to keep one child alive. The VC is trying to get two of thirty to the Olympics.

Calm is the bicycle he keeps citing. Invested at $5 million, next round at $250 million, no money in between, $10,000 a month in revenue to millions, a feat of capital efficiency he has seen three or four times, and only in high-margin software with extreme product-market fit. Hardware usually cannot do it. Young VCs, scared, also collide with the J-curve: bad news arrives first, two or three of ten bets are dead in year two, performance goes down, and only in years four through six does the line turn up. People who started when he did, in 2009, after the crash, all look like geniuses because the market went up. It takes a decade to know if you are good, and a founder who takes the money has just walked into that casino.

Calacanis, Chamath Palihapitiya, David Sacks, and David Friedberg record *All-In* every Friday; they are poker buddies, and GameStop week they swung swords at each other on tape. Chamath’s view, as Calacanis steelmans it, was that Robinhood turned off buying because hedge funds told it to. Calacanis says that is not true. In a vacuum, conspiracy theories bloom, and sometimes there is a conspiracy; here, he says, Robinhood needed billions to stay solvent, was not allowed to say so, and had to raise or shut down. After the show they had a private conversation he had not described in public until this interview. They love each other. What happened, on his side, is loyalty.

He is, in his own word, a bulldog for his founders — Uber’s Travis, Robinhood, Sacks, whoever is on the list. Uber made plenty of mistakes; he still went on CNBC and said the intent was good and they would fix it, and he was hated for it. Robinhood week was the same blowback. He thinks he was eventually right both times. If you are on the team, you fight, you go silent, or you throw them under the bus. He has watched investors dump the people who made them rich. Unacceptable. Silence is also unacceptable. He asks the founder first: do you want me to defend you in public? If yes, he does. Brooklyn in the 1970s and 1980s, and a father who owned a bar, drilled the same lesson: you do not want to be a ronin in a fight with ten people. Chamath called his guys scumbags who should go to jail. Calacanis was skiing with his daughter on the first vacation of the pandemic, came off the mountain into a global story, and did not have complete information with which to answer.

They talked it out. Chamath said he got hot defending the everyman; Calacanis said that was what Robinhood was built to do. Friends will fight. This one happened to be the number one story in the world, which he suspects would not have been true if Trump still had a Twitter handle and could swallow the news cycle. Nuance and intent, he argues, have been lost. When someone attacks him he looks for the intent, and it is almost never the movie he wrote in his head. Last summer a fan of a *New York Times* journalist reverse-image-searched a sky and a tree line, found an old listing, and posted Calacanis’s home address and its value. The man was 42, in Boston private equity, a baby six months old, seven people in common on LinkedIn. Calacanis asked him to take it down, threatened to call the boss, then got on the phone instead. The man called it the biggest mistake of his life. His wife called him a moron. Calacanis let it go. Calling the boss would have fired a new father. “Life’s hard enough.”

Fridman asks what love, family, and friendship are for on a path this brutal. Calacanis tells a story he usually avoids because Musk is so famous now, and only because Musk has told it publicly. During the financial crisis they went for steak in Los Angeles, Roadster and a McLaren at the valet. Calacanis had read that Tesla had five weeks of cash. Musk said two. SpaceX’s third launch was coming; the first two had blown up, and a third failure would end the company. Calacanis offered to loan a couple of million he did not really have. Musk said their friend Bob had already loaned him money. He was, in Calacanis’s phrase, functionally bankrupt, with equity racing toward zero, trying to decide whether there would be a Christmas vacation.

Calacanis asked for some good news. Musk pulled out a BlackBerry — there were no iPhones yet — swiped to a full-size clay Model S, and said not to tell anyone. Range, maybe 250 miles. Price, maybe $50,000 or $60,000. Calacanis told him that if he made that car he would change the world: the Roadster was for a couple of thousand people in eight states, and this one was for the country. At home he asked his wife Jade for the checkbook, wrote two $50,000 checks, scrawled that he loved the new car and would take two, kissed them, and FedExed them for Monday. He told her the $100,000 would vanish in 48 hours, one or two days of payroll, turning two weeks of runway into twelve days. The checks did not cash. Musk closed money in the next week or two. Months later they cleared.

Three years later two emails arrived: reservation 0000001, then five seconds later 0000073. Calacanis forwarded number one back and said he could not take it. Musk said he already had five, and Calacanis had been first to order. Calacanis says Musk got a bit teary. It was, for both of them, a beautiful moment in what Musk has described as the darkest period of his life. The Roadster now sits under a cover in Calacanis’s garage with about 20,000 miles, number 16 beside it, and he gets a warm feeling walking past them because the impossible thing happened. Friendship, he says, is you get what you give. Kindness builds a bond that is very hard to break. At the end we are a series of memories with the people we love. He quotes Roy Batty in *Blade Runner*: those memories go like tears in the rain. They are here now, which is why you show up.

Bitterness, disappointment, sitting at home angry: those use the same energy as loyalty and kindness, Calacanis says. The water is going to flow; you choose the direction. The most important moment in his friendship with Sam Harris arrived when he was struggling. Harris told him to picture sitting by a river of thoughts. You are not a slave to any of them. They whip by like waves. You can pick one up, look at it, keep it, or put it back. In that sentence he parked a lifetime of insecurities and imposter syndrome. He did not go to MIT. He is not, in his telling, the smartest person in the room. He wrote little $50,000 checks, then $3 million checks, worked as a journalist, ran a small podcast, and at 50 he is proud of the pile.

Mega-funds have invited him in and called him an idiot for putting $30 million a year to work across 60 companies at $500,000 a ticket. Come write $150 million checks, go to Aspen and Cabo, stop working. He does not want to be an ATM for companies that are already huge. He wants to meet the two people with the idea in year one, in a basement, and write check one, two, or three. Check three thousand is boring. The feeling he is chasing is the email from Calm: sleep features, streaks, 10x in three months, we are not going to die. Most of them die. He likens the rest to baby turtles sprinting for the ocean while seagulls shred them and sharks wait. Two or three become hundred-year-old turtles. You remember the morning their siblings were torn up, and that they made the deep water.

Nobody gets there alone, he says, and anyone who thinks they did is kidding themselves. A Christmas card he almost missed in the second week of January was a long letter from someone he had helped 25 years earlier. It hit him like a ton of bricks. Martin Seligman’s work on happiness, as he cites it, finds that thanking someone who changed your life is one of the strongest amplifiers of joy, and it costs nothing. If you are listening, there are probably ten such people. Call, email, or send a letter. Lex closes the episode by quoting him: the number one reason a startup shuts down is not running out of money. The number one reason is that the founder gives up. In Calacanis’s frame, what keeps a founder from giving up is a reason they cannot not do the work, and the people who did not walk away in month nine.