Framework
Slingshot startups: businesses set back by COVID that snap forward
Shaan relays Jason Calacanis's term for companies that were pulled backward during COVID and are now building pent-up momentum to launch forward, the way a slingshot stores energy when drawn back.
“Jason Calacanis had a good phrase where he goes slingshot startups. They had a setback. They were pulled back during COVID but it like, it's like a slingshot when you, when you, when you pull it back, it's, yes, it's gone backwards, but it's building up this momentum to slingshot forward.”
Steal thisHunt for sectors hammered by COVID (events, travel, hospitality) and back the ones poised to snap forward on pent-up demand.
Fact
Be in people's ears 45 minutes a day and deep trust forms
Shaan explains why he started a podcast despite weak direct ROI: being in someone's ears 45 minutes a day builds deep trust like the trust he felt for Bill Simmons and Calacanis. That trust is exactly why he could later raise a Rolling Fund from listeners without tapping anyone he knew in real life.
“But I just felt like if I'm in your ears for 45 minutes a day, You're gonna make a decision. You're gonna say, this guy's annoying, I don't like him, he's stupid, and you're gonna churn out. Fair decision by you. Or if you stick around, this like deep trust is gonna form.”
Steal thisBuild a podcast as a trust-compounding machine; the audience that sticks will back your future ventures.
Story
Calacanis on moving to Austin: the pandemic killed in-person deal flow
Jason Calacanis explains why he's considering leaving San Francisco for Austin after building his accelerator around in-person meetings. Once the accelerator and his podcast went remote, 2-3x more people applied and nobody wanted to come to SF, dissolving his belief that meeting founders in person was his edge.
“Then I thought I refused to have anybody on the podcast unless it was in person, because I thought my superpower, Sam, was to be able to look people in the eyes and decide if I should invest in them, or to look them in the eyes and be able to figure out what the next question was on the podcast. Now 100% of people have awesome setups, are totally accustomed to Zoom, and don't want to come to San Francisco either to be on the podcast or to come to our accelerator.”
Number
SF real estate costs 2-3x Austin per square foot
Calacanis contrasts housing prices to justify a move: San Francisco and the peninsula run $1,500-$2,500 per square foot while Austin is only $600-$1,000.
$3K
San Francisco home price per square foot (high end) · USD/sqft
“I mean, in San Francisco, everything's $1,500 to $2,500 a square foot. In Austin, it's $600 to $1,000.”
Story
Calacanis: journalism and venture investing are the same questions
Calacanis traces his path from magazines (Silicon Alley Reporter, a $12M business) through the dot-com crash and Weblogs Inc. to angel investing, arguing journalism and investing ask identical questions. He notes Michael Moritz and others made the same journalist-to-VC jump.
“And really, as a journalist and a publisher, you ask questions and you try to get to truth, or at least you used to. Now you kind of— we could talk about late-stage journalism, but back in the day, original journalism, you were supposed to be independent and just ask really honest, fair questions, get the answer, don't double-check that your facts were correct and publish a story and not put a linkbaiting headline on it.”
Take
Get your gambling rush from startups, not poker
Calacanis stopped playing high-stakes poker because the swings felt addictive and unhealthy, and because he's far better at startups than cards. He reframes angel investing as the place to channel the gambling itch since the upside dwarfs anything at the table.
“I would rather get the rush of gambling through startups and investing in them than in poker, because I feel like I'm better at startups than poker. I mean, I know I am. I'm top 5 angel investor of all time, and in poker, I'm not even in the top 5 million or whatever, you know, in all likelihood.”
Steal thisChannel your gambling impulse into the game you have edge in, not the one where you're a fish.
Story
How Calacanis got into Robinhood: a bar pitch with Elon present
Calacanis recounts meeting Robinhood's founders in a Palo Alto dive bar while having a drink with Elon Musk. Vlad's pitch was to get commitment-phobic, debt-laden millennials to trade stocks for free at a time when retail investors had vanished since 2008, and the absurdity of the pitch is exactly why Jason invested.
“He said, "Well, we're going to make it free." I said, "So your idea is to go after a group of people who are on their parents' Netflix accounts to save money, get them to trade stocks, and your business model is free?" He's like, "Yep." I was like, "I'm in." So I invested.”
Number
Calacanis's Uber stake peaked at 4,000-5,000x
Calacanis says his Uber angel investment was worth as much as 4,000x to 5,000x at peak depending on exit timing, and he still holds roughly half his position.
$5K
Peak return multiple on Uber angel investment · x (multiple)
“the Uber investment, uh, wound up being— I mean, at its peak, maybe 4,000x, 5,000x, depending on when, you know, you choose to sell it. And I still own, I think, around half my position, so I'm still long Uber.”
Fact
Why today's startups scale faster: 100x market, 10x usage, ad networks
Calacanis argues entrepreneurship is timing: when he was a founder the market was ~20-30M broadband homes, but now 2 billion people carry smartphones with stored credit cards and check them all day. Combined with sophisticated ad networks, this is why companies like Clubhouse go 0 to 10M almost overnight.
“Now you look at the market, we've got 2 billion people with high-speed smartphones in their pockets. So just do the math on that. It is 100x the desktop market that we used to address”
Steal thisRead the platform shift before picking your startup; a 100x bigger addressable market is doing half the work.
Tactic
The list as a kingmaker hack: rank a sensitive scene and they need you
Calacanis built influence in New York tech by inventing the Silicon Alley 100 in 1996 even though only 60 people worked in internet at the time, filling the rest with random picks. Ranking everyone forced PR people to lobby him, making the unknown publisher a power broker.
“I started Silicon Alley Reporter and I said, let's do our top 100 internet people. But at the time in 1996, we could only find 60 people in total who were working in the internet industry. So then I asked the 60, do you know anybody else? And they— my team said, let's just make the top 10 or top 25. I said, no, it's got to be 100.”
Steal thisPick the most prideful scene and publish a ranked list of its players; you become the kingmaker everyone has to court.
Idea
Paid communities: the top 10,000 in any niche will pay ~$100/yr
Calacanis sees paid communities as a huge opportunity, citing portfolio company SoleSavy charging $30-40/month. His thesis: the top 10,000 people in any topic will pay $20/month or $100/year to be part of a community around it.
“So I think the top 10,000 people in every topic want to be part of a community and pay $100 a year or $20 a month or something like that to be part of it.”
Steal thisBuild a paid community for the top 10,000 fans of any niche and charge ~$100/year.
Fact
Your reward for succeeding on a percentage platform is losing the customer
Calacanis argues percentage-take businesses (Substack, Patreon, ad rep firms) are structurally doomed with their best customers: once a creator gets big, the cut becomes a salary's worth of money and they leave for flat-fee tools, just as Sam Harris left Patreon for his own site.
“And so your reward for succeeding was losing your best customers. The reward for Patreon succeeding is they lose that customer to a Stripe or Ghost, or, you know, there's all these like tools that charge you a flat rate to do subscriptions.”
Steal thisIf you build a percentage-take platform, lock in value beyond billing or your winners will defect to flat-fee tools.
Idea
Microschools: two private-school tuitions equals one teacher's salary
Calacanis did the math on a microschool: teacher salaries run $45-80K while private school is $30-60K per child, so two kids' tuition covers a full-time teacher and three puts you at a profit, all at a 1:2 or 1:3 ratio. He hired a private teacher for his 11-year-old and calls it her best year ever.
“Private school is $30,000 to $60,000 depending on what city you're in. So 2 parents in private school equals a teacher because there's so much overhead. So if you just do the math, you can basically hire a teacher and have 2 students and you're at breakeven, and 3, you would be basically at a profit. So, or a cost savings, and you would have a 1 to 2 or 1 to 3 teacher ratio.”
Steal thisPool 2-3 families' private-school budgets to hire one dedicated teacher and run a microschool at breakeven.
Prediction
Miss
Calacanis: Bitcoin could go to zero or under $1,000
Calacanis says with no use case beyond speculation and storage, a better technology could trigger Reddit-style mania and drain Bitcoin, making 'Bitcoin zero or Bitcoin under $1,000 a distinct possibility' over a slow ride. He advises holders to take profit and buy a house.
“So I think people being bullish on— I still think Bitcoin zero or Bitcoin under $1,000 is a distinct possibility. Now, would that happen overnight? No, I think it would be a slow ride as people realized Ethereum or whatever the next one is, is the better one, right?”
Take
Crypto promised a new internet; exactly one app shipped: store of value
Calacanis's bear case on crypto: it was sold as the new internet that would change everything, but unlike the real internet's many killer apps, crypto has produced exactly one real use case (speculation and store of value) and dented nothing else.
“Crypto was positioned as this is the new internet, everything is going to change. And exactly one thing has changed— store of value. That is the only thing that has changed— speculation and store of value. There is nothing else crypto has put a dent in.”
Prediction
Pending
Calacanis: non-accredited investors in private markets is the next decade's revolution
Calacanis says he's short crypto and long startups, and most of all long non-accredited investors entering private markets. He predicts a sophistication test (20-40 questions) will replace pure wealth-based accreditation, unlocking the 96% of Americans currently shut out.
“I'm really long non-accredited investors participating in private markets. I think that's going to be the big revolution of the next decade.”
Framework
Narrow aperture vs. general: niche caps your audience, general can explode
Calacanis contrasts his two podcasts: This Week in Startups has a narrow aperture and a distinct endemic audience, while All In covers the top 5 topics in the world and so can reach many multiples more people if it clicks, which is how it hit #11 overall in 19 episodes.
“So, you know, if you have a narrow aperture, you know, you can get a very distinct endemic audience like you have for your podcast or I have for This Week in Startups. And then if you go general like Ben Shapiro or Joe Rogan or All In Podcast, you can get many, many, many, many, many more folks if it clicks.”
Steal thisDecide deliberately: narrow aperture for a loyal endemic audience, broad aperture for explosive reach.
Framework
Kingmaking: become the power player by deciding who the kings are
Shaan cites Jason Calacanis's Silicon Alley 100 as the playbook: by arbitrarily creating a 'most influential' list, you become the kingmaker every power player wants to court, instantly making yourself a power player.
“he basically was like, oh, this was my excuse to meet every single power player, uh, they did an interview with me, they sent me their headshots, they wanted to be on the list. I could kind of decide who's in front of who, and because I was the kingmaker of deciding who's on the list, all of a sudden I became a power player, uh, in that scene. And I just think this is like massively underrated.”
Steal thisCreate the definitive ranking list in your niche; being the kingmaker grants access to everyone on it.
Fact
Why VCs slow down in a crash: the capital call problem
Shaan relays the All-In framing: VCs don't hold the cash, LPs do. When stocks crash, a fund's venture allocation balloons past target weight, so LPs ask the VC to delay capital calls, freezing the pace of startup investing.
“what happened in 2008 according to Chamath and Jason, it was very interesting. What they said was the VCs didn't stop investing, but they definitely slowed down because what happens is when the VC commits to a startup, they do a capital call. They say, hey, LPs, we found a startup. We need, you know, that money you committed.”