In this talk, Jason Calacanis warns that rapid advances in artificial intelligence and automation will soon eliminate large swaths of both blue‑collar and white‑collar employment, citing the replacement of top Go players, Kasparov, and poker pros as precedents and projecting that up to half of retail, driving, and other service jobs could disappear within a decade. He links this looming job loss to a broader crisis of wealth inequality, criticizing current tax policy, capital‑gains treatment, and political leadership that favor the ultra‑wealthy while neglecting basic public services. Calacanis proposes a solution: democratizing access to high‑growth startup equity. He explains that recent SEC rule changes now allow non‑accredited investors (the 96 % of Americans) to invest in early‑stage companies through platforms like Republic and SeedInvest, and he advocates for angel syndicates that allocate a portion of fundraising rounds to the public. By investing modest sums across many startups, individuals can achieve “escape velocity” if a single investment yields outsized returns, thereby providing a pathway from poverty or the middle class to wealth. He shares his personal background—a Brooklyn kid whose parents lost everything—to illustrate how he leveraged angel investing to achieve success and why he wrote a book to inspire others. Throughout, he blends a dark view of the economic future with an optimistic, actionable strategy centered on startup equity participation.
Chapters
So anyway, nobody in the room's job is harder than 5— beating the top 5 Go players. Well, guess what? Google beat them with AI, and we beat Kasparov, whatever, a decade ago, and we're beating poker players and the best poker players in the world. AI, when focused on one vertical, will win, right? Right. And it's just a matter of time before they focus on accounting, legal. I've seen 6 or 7 startups focus specifically on contracts and legal. So I think half the legal work is is gonna be done by machine learning in another 10 years. And how many people here know people who got their law degrees and couldn't find a great job? We all know somebody like that, right? Or you're that person, right? You suffered through it. But it's true. So what do we think's gonna happen in the next 10 years? Okay, now let's add to it the fact that 30 million people in this country work in retail or driving a car. McDonald's just put in Self-serve kiosks. Pizza self-serve kiosks. Panera Bread self-serve kiosks. Anybody here think that the idea that a person hitting buttons and collecting money at a register is going to be a job that exists in 10 or 15 years? Okay, so we're all fucked. This is a very dark, dark view of the world. Not only are the 30 million retail and driving jobs going to— let's say 80% of them go away, half of them go away. We're gonna have 15 million Americans, 5% of the country, and essentially 10% of adults are gonna be out of work already compared to how many people are out of work. And white-collar jobs are gonna start going. Right. Okay, so how are we all gonna survive? Where are the— where is the opportunity to move from poor to middle class? Or poor to wealthy, or middle class to wealthy, or wealthy to ultra wealthy. Well, you don't have to worry about wealthy to ultra wealthy because the entire system in America is rigged for the wealthy to become ultra wealthy. Capital gains tax, LLCs, Donald Trump as president. I mean, it's just— I mean, listen, it's the biggest disaster in the world. I was discussing it with my wife and I was like, oh my God, do you realize how little in taxes we're gonna be paying? This is horrible. Like, we're gonna save a lot of money, and then there's gonna be a lot of pain and suffering, and people can't go to the doctor, and people, we're gonna get rid of preschool. I mean, we're getting rid of so many important things. It's disgusting, it's horrible. And it's at the exact time when all of these AI jobs and automation are gonna be happening, which is a very crazy time. Mm-hmm. I believe that the hack that will get people into the ability to move from poor to rich, from middle class to rich, and to have bounty in life is to be on the cap table of high-growth startups. Right. I believe in my heart that if you had $100,000 to invest, doing it in, or some percentage of it in high-growth startups would be worth doing it. Because let's say you put 5 or 10% of your net worth into this and you lose it, or you lose half of it. If you lose all of it, you lose 5 or 10% of your worth. And if that's, let's say, $100,000, if you had $1 million in savings and you lost $100,000, 10% of it, you wouldn't be destitute. You'd be bummed, but you wouldn't be destitute. Yeah. And you will have invested in 30 companies, 25 or 30 companies, and you'll learn something and you'll have networked. If you lose half of it, you'll be networked, you'll be, you know, bummed, but not super bummed. But what if you hit Uber or Airbnb or Google or Facebook or even a 100xer? And all of a sudden, you know, you 10x your money. Right. Now you've doubled your net worth and now you're starting to have escape velocity. And one very interesting thing has happened. Non-accredited investing, which is 96% of the country, just got passed. Right. So we see Republic and SeedInvest are doing non-accredited investor fundraising. I think this is going to change the world and everybody's saying it's not and it's going to be like the worst companies and it may be the worst companies right now or maybe the companies where it's the funding of last resort. Some cases. I don't think it's all cases, but this is the same thing people told me when I started my syndicate on AngelList. Right. I moved it to Jason's Syndicate now, which is no dig to AngelList. I just wanted all the carry for myself, and I don't need that platform. We have so much reach, but I really believe in syndicating my best deal flow to everybody. So I really hope that the founders I work with will consider emailing their entire list of customers and their friends and family and saying, hey, we're going to put $1 million available to the public in the next Uber, Thumbtack, Robinhood, Desktop Metal, DataStax, or Wealthfront. Right. I would love to see those companies when they're raising their first $10 million allocate $2 million of it to the public at $100 to $500. How many people here knew in the first year of using Facebook, LinkedIn, Twitter, Uber, or Airbnb that these would be significant companies? How many people knew those would be significant companies? Raise your hand if you thought this is a pretty cool company. It's like maybe 25% of the audience knew those are going to be significant companies in year 2. How many people knew in year 2 of LinkedIn or Uber, Airbnb, or Facebook that they would be significant companies? Raise your hand nice and high. So now we're up at half. Okay, those companies went public in year 5, 6, or 7. So in the first 2 years, half the audience would have made a bet on one of those. My mom knew that Twitter and Facebook and LinkedIn were going to be great companies. She's into it, but I mean, she's not like here every day. She's in Brooklyn. Why can't Americans invest in these companies early on? Right. Well, it was because of some antiquated legislation that the SEC has now changed. And we're going to see one of these companies will be brave enough to do it. Some founder will be brave enough to do it with a high-quality company with serious revenue. And we might see, you know, 1,000 Americans put $1,000 in each. And I'm talking about teachers and garbage men and firefighters and just, you know, salt-of-the-earth blue-collar people put $1,000 into a company or $500 company and have it go 1,000x. Right. And get back $500,000 or $1 million. And be able to buy a house again. Right. And it comes full circle. That's why I wrote the book. Honestly, I think I didn't have to write the book. It was an opportunity cost for me to write it. I could have been investing in startups during that time, but I just thought, you know, I figured something out. And it's— although life is a zero-sum game in many ways, angel investing happens to be one unique place where collaboration is critical and virtuous. I have never met a startup that didn't have a dozen investors in the first couple of years. Right. And typically they have 2 or 3 dozen on the cap table by year 3. It is a collaborative sport. Even myself, Chris Sacca, Scion Bannister, we don't have the ability, nor do we want to be the entire round. We want to have multiple investors involved because multiple people bring more skills to the table. And that's what we're going for. So with the book, I'm just hoping to inspire some number of people and help them get rich, help them move from the middle class to the upper class. I'm not worried about wealthy to ultra-wealthy. That's gonna happen. I mean, if you just put your money in the stock market and you can't collect capital gains and dividends, you'll be fine. Yeah. We have a real problem in America right now of going from poor to middle class and from middle class to wealthy. It was really good for a couple of generations. But then we decided to add capital gains and a bunch of, you know, lower the tax rate for the ultra-wealthy while claiming that the ultra-wealthy are paying more in taxes. They're paying more in a total dollar amount. They're paying less than they ever had. Right. So it's all a lie. And Trump is continuing that lie to an absurd basis. I mean, he's telling everybody that his healthcare is gonna be better. It's a bold-faced lie. He's telling everybody he's gonna reduce the budget. He's gonna spend more, and he's giving people huge tax breaks who don't want or need it. Right. People who are affluent in this country are scared to death right now of a coming revolution based upon the polarization of wealth. It's too easy on the wealthy in this country. They're not doing their fair share, and that's why they're all taking the Giving Pledge, Because they're scared to death that this is gonna turn into Marie Antoinette. I mean, they're gonna be coming with the guillotines for the rich. Right. Operation Wall Street was an example, it was kinda like the dry run of how upset people are at the polarization of wealth in this country. It is completely unfair that we're fighting against a basic minimum wage while at the same time giving tax cuts. And we're so rich. This country's so rich. We have so much money, and we can't provide healthcare for everybody? It makes no sense. Tiny countries with less resources than us are doing it, and we can't? For what reason? Right. Because of some political battle? I mean, these are human beings who are suffering, and we want to take away childcare. We want to— I mean, it's unconscionable what's happening in the country right now. Right. And I feel like, listen, you know, the system is rigged. And I'm a kid from Brooklyn. Mom's a nurse. Dad was a bartender, owned a bar. They lost all their money when I was 17. I had to fend for myself since then. I figured it out. I got lucky. I hacked my way to some success. I got lucky 7 or 8 times. And I wanted to share a little bit of that story of how I did it. Right. And I hope other people read it, deploy it, and become wealthy. That is sincerely and truly my goal. I don't need to sell books. Thank you.
