Ahead of RAISE Summit 2026, John Furrier caught up with the All-In Podcast co-host to talk startups, AI, investing, and what ...
What Jason Calacanis said
Written from the verified transcript and checked against it. Every figure links to the moment it was said.
Jason Calacanis argued that younger generations were sold a false bill of goods: college tuition rose from $5,000-$10,000 a year to levels leaving graduates with $250,000 in debt, while starting salaries stayed around $60,000, four times their annual pay versus 15% for his generation. He said restrictive housing policies in cities like San Francisco and New York broke the system, and that fixing education and housing, plus healthcare innovation, could reverse disillusionment with capitalism. On entrepreneurship, he said time to first customer collapsed from 18 months to 3 days using tools like Lovable and Cursor, enabling three-person companies to hit $1 million in revenue. He discussed All-In's growth: the summit doubled revenue four times, Liquidity in Napa was 4x oversubscribed with 600 allocators, and the business could reach hundreds of millions. He emphasized media consistency and designing events around the band's joy.
Key takeaways
College debt now averages $250,000 versus $60,000 starting salaries, four times annual pay, compared to 15% for his generation.
Time to first customer dropped from 18 months to 3 days using AI coding tools like Lovable and Cursor.
Three-person companies can now reach $1 million in revenue, previously requiring 10-20 people.
All-In Summit revenue doubled four times since the first Miami event, and Liquidity in Napa was 4x oversubscribed with 600 capital allocators.
All-In business could reach hundreds of millions in revenue, with tequila already doing millions annually.
Go Cube NYC Wire. We've seen so many times a person who is a nobody change the world. And if you've been around Silicon Valley or the tech industry for more than 20 years, you've seen it over and over and over again. What I love about you is not only that you're a smart entrepreneur pioneer, you work hard. And I know that you talk about a lot on Twitter. What's it like with young people these days? Are they working hard enough? How do they make money? You got a good crystal ball. Values? Yeah. A lot of things. People like to paint with a wide brush for every generation. So, every generation from the '60s and the boomers, they were a bunch of hippies and they didn't work hard and now they've got more money than anybody and they've got three homes, too many homes has caused all kinds of problems. So, these next couple of generations after our generation, Gen X, I think in some ways they were sold a false bill of goods and they have had to become very resilient. They were told, like us, if you go to college, you work hard, you'll get a job, a career. So you'll start with a job of some kind, and it will work its way into a career, and then you'll have a life.
And all of that's predicated on just doing well and don't get too many things on this permanent record. Turns out there's no permanent record, spoiler alert. But just do well enough to get into a good college and everything will be fine. What they didn't tell them was when we went to college it was 5 or $10,000 a year in tuition. So you could get out of college with 25 to 50k on the high end of debt. I graduated with I think 7 or 8,000 in debt. My first job when I was working in IT was 60,000 a year. So if you were to look at my pay as a function of that's good bank back then actually was pretty great. Yeah, I was in IT but you know it was maybe 15% of my yearly salary was my total tuition. Now people are graduating from college. They're also making 60,000 and that's 30 years later. They're making 60,000 but their debt might be 250,000. So they have four times as much debt as their yearly salaries as opposed to 15%. And that has led to them maybe not believing in entrepreneurship, not believing in capitalism even. And we've got to reverse that. And if you go to certain states in our union, just Texas, where I live now, in Austin, Florida, Nevada, they make plenty of homes. But I lived in three great cities my whole life. Brooklyn, New York, Brooklyn, Manhattan, Los Angeles, and San Francisco, the Bay Area. And those places, you can never build a new building. No,
They don't let you build new buildings. And that one simple thing has, I think, broken that generation or those two things, education and housing. And if we can fix those two things, healthcare as well, we need some innovation. But those things could all be innovated away and I believe they will be with robotics and human robotics and other tech. You and I have done a lot of Austrian ventures. We all work hard. It was a different era. So two questions. Entrepreneurship. People think I just get a degree and be an entrepreneur. Hey, I want to be an entrepreneur. I saw the social network. I want to be like Mark Zuckerberg. It's so easy. So talk about the modern entrepreneurship mindset. Two, how is PI going to change how entrepreneurs operate, how they recognize themselves? What's your thoughts on that?
Yeah, I always think about time to first customer. So, Peter Teal has zero to one. I like 0 to $1. So, how quickly can you get a customer to pay you for a product? And it used to be when we first got into the industry in the '90s, you would raise three or four or $5 million for 40% of your company and two years later you release your product. Maybe if you were fast it took you 18 months. Well then cloud computing mobile, GitHub, you know, and all this technology brought it and we work and just renting a desk to for 250k you could release an app and it would take you 6 months. Now people can while they're working at their existing job or they're at college use lovable or quad code or grock code or codeex and even not being a developer build a prototype that's functional, email 10 people, get two of them to put their credit card in and have a customer. So zero to customer went from 18 months to 6 months to 3 months to 3 days. And we're now seeing people with three or four people in their company getting to a million dollars in revenue. That was, you know, typically 10 or 20 people in your company. So the efficiency means we can try more things, but the prerequisite is you have to be just a rugged individual. You have to have self-reliance. And we don't teach grit, self-reliance. Those are things you earn. And to earn self-reliance and grit, you have to do hard things. And being an entrepreneur is one of those really hard things. I've been doing Silicon Angle the cube now seven this is my 17th year doing amazing and we've just started a new brand NYC wired which is combined second capital market explain to people why technology is the market you can get massive gains if the company is thought of from the bottom up as a technology company it's embedded in everything the same way electricity was added right you kind of added electricity to a business you added the combustion engine but now the businesses are just made like that from the
Beginning. I've been following All-In from day one. I got to say I've been watching, that's been curious. For this fun, you guys are doing pretty well. What's next? What's the vision for All-In? Because well, you have that mind, I can see.
6 more exchanges in this transcript
Sign in free to read the rest of this interview. No card required.
Calacanis, J. (2026, July 7). Jason Calacanis has built a front-row seat to the future of technology [Interview transcript]. SiliconANGLE theCUBE. CEOInterviews.AI. https://ceointerviews.ai/interview/1069590/
MLA
Jason Calacanis. "Jason Calacanis has built a front-row seat to the future of technology." SiliconANGLE theCUBE, 7 Jul. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/1069590/.
BibTeX
@misc{calacanis2026_1069590,
author = {Jason Calacanis},
title = {Jason Calacanis has built a front-row seat to the future of technology},
howpublished = {Interview transcript, SiliconANGLE theCUBE. CEOInterviews.AI},
year = {2026},
month = {jul},
url = {https://ceointerviews.ai/interview/1069590/},
note = {Speaker-attributed transcript with timestamps}
}
