Founder of LAUNCH, LAUNCH
E753: LAUNCH Angel Summit: Esther Dyson on angel investing, jobs, health, AR, VR & self-driving cars
Filmed live on stage at the 2017 LAUNCH Angel Summit in Napa Valley, Jason interviews Esther Dyson, journalist and technology investor turned wellness enthusiast, who is on a mission to better health by rethinking and recreating the environment in which it can thrive. In this special episode of TWiST, Jason and Esther discuss the progression of angel investing over the years, the complexities around U.S. and Russia relations, predictions of AR, VR, & self-driving cars, real-world issues including diabetes and income volatility, and more.
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About Jason Calacanis
Jason Calacanis, co-host of the All-In podcast and founder of LAUNCH, has been active on his podcast and at events discussing investment strategy, the technology industry, and political dynamics. In October 2024, he outlined his investing philosophy, emphasizing backing a team's vision over hype and dollar-cost averaging into companies one believes in. He described Elon Musk as having a gift for pursuing multiple visions concurrently and argued that criticism of valuation hand-wringing stems from an inability to tolerate ambiguity across multiple business lines. In mid-2026, Calacanis moderated the All-In Liquidity Summit in Napa Valley, describing it as an event for the "top 0.1%" of the podcast's audience, with 550 capital allocators representing $7 trillion in capital present. He stated that the event was part of a broader community-building effort and that his philosophy for events is that attendees return if they make a great contact, have a great experience, or learn something. Calacanis has also commented on the current tech boom, which he attributed to AI, noting that companies like xAI, OpenAI, and Anthropic are going public. He described seeing "a Cambrian explosion in startups" and said he personally invests in roughly 100 new companies per year through his fund LAUNCH and a program called Founder University. In a May 2026 appearance on the Bulwark Podcast, Calacanis discussed why some in Silicon Valley have been reluctant to criticize President Trump, arguing that access to the administration to shape policy is preferable to not having one's phone calls returned. He also described former President Trump's handling of Iran as "an unmitigated disaster" and said he believed it would "kill his presidency." Additionally, Calacanis has been publicly critical of Mark Zuckerberg, stating that the Meta CEO has "damaged the reputation of the industry" by repeatedly prioritizing self-interest over what Calacanis described as the right thing for humanity, including in matters of privacy and content moderation.
Transcript (34 segments)
✨ AI-enhanced transcript with speaker attribution
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Narrator0:00
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Jason Calacanis0:35
So my first speaker is Esther Dyson. Come on up, Esther. I'll do a quick big round of applause. Yes, big applause here. So 22 years ago, I was coming into the industry. I was a little rambunctious kid from Brooklyn, and I was studying, trying to figure out how people became important and powerful. This was my obsession as a kid from Brooklyn. When you get into Manhattan, you're like, how do you become somebody? I studied the landscape and I saw Esther Dyson. Everybody kept talking about Esther Dyson. She had a newsletter, a conference, and she was an angel investor. I was like, wow. Everybody who was important and had a question about the future would come talk to Esther. So then I proceeded to make a newsletter, a conference, and now I'm angel investing. I haven't figured out the fourth one. Important people don't come to me for my opinion yet, but they did for you. How did you get started in angel investing? What was it like back then? What was the first angel investment you did?
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Esther Dyson1:48
These are hard questions to answer. I did indeed have a newsletter and a conference. I had started a second newsletter. The first was called Release 1.0, the second was called Rel East about Eastern Europe, and that was in the '90s. Precisely because I had a newsletter and a conference and was kind of old-fashioned, I specifically did not invest because I felt it would be a conflict. The reason I had my newsletter was because I bought it from a guy called Ben Rosen in 1983. He was chairman of Compaq and Lotus at the time, so he could not honorably write a newsletter about the industry. So here I was, it was early to mid '90s, and a friend of mine came to me and said, 'You keep talking about people should invest in Eastern Europe. Suppose I give you a million dollars, would you invest it for me?' I said, 'Oh no, no, I can't. I'm a journalist.' But how much money? Back then, a million dollars in Eastern Europe was like 10 or 20 million. That was not an insignificant sum. So I took the money, shut down the East European newsletter to avoid the conflict, because I discovered one way to get people to talk to you is if you're writing about them, another is if you give them money. And if you give them money, not only do they talk to you, sometimes they take your advice. So that's how I got started. It was called Adventure Ventures. One of the companies was a real winner. Some of them all kind of morphed into different things. It was typical VC/angel. Three of them just kind of disappeared without a trace, but two of them turned into something that keeps returning odd bits of money. How quaint is it to think about how we looked at the media 20, 30 years ago in terms of conflict, given today when it seems like the whole goal of media is to see how conflicted and integrated you can make these stacks. It's true. There's what I like to say: there's the church of media, and then there's the religion of transparency and journalism. I'm still an altar boy for journalism, still hoping that something comes out of that. Some things about Russia that we all don't... Having spent a ton of time there, and I don't want to have a whole conversation about Russia, but it's kind of like Trump. It just invades everything.
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Jason Calacanis4:34
Exactly. We both spent a lot of time in New York during the time when Trump was also infecting the city. The metaphor is going to have to stop. What is your take on Russia's influence? If you had to bet, is this standard operating procedure what they're doing with the Trump family and these revelations of meetings and quid pro quo and getting compromising information? What have you learned working over there? How many people have been to Russia? That's actually a surprising number, looks like about 15%. How many speak Russian? Only four or five. This is a pretty amazing room. Tell us about what your take on all this is. You must be watching it with some kind of insight.
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Esther Dyson5:27
I'm still active there. I'm on the board of Yandex, which just did a very interesting deal with Uber yesterday around the ride-hailing business in the former Soviet Union. It's complicated. I think the purpose, let me word this very carefully, the purpose of whoever is doing this was not to elect Trump. It was more simply to create confusion, distrust, and cynicism. There's a big difference there. The US itself goes around the world and does stuff. They usually focus on trying to get somebody elected. I was on the National Endowment for Democracy board. We would go out and train people to write constitutions and create rule of law and do really positive stuff like that. We all know the US government has also done things that are less visible, but they usually are not focused on creating chaos. They're trying to create cohesion. So they're trying to create chaos, distrust in our system, or distract us. It's more distrust. Why? I guess it makes them feel more powerful. Fascinating. So if they can push our buttons, if they can mess up our system, it shows they can get to us in a way that someone like Kim Jong-un likes to launch a rocket now and again to make us pay attention. Fundamentally, Russia feels aggrieved that the rest of the world doesn't give it due respect. Honestly, very much like the white male in our society, many of whom have lost their jobs, lost their position. Those people who want to vote for Trump and get their power back, it's kind of a perfect match. They like the message.
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Jason Calacanis7:45
How do you think this all ends? I know this is an impossible question, but you've seen a pretty good arc of history now.
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Esther Dyson7:52
It doesn't end well. People keep thinking, when are we going to come to the end so we can relax? Fukuyama's 'End of History' was probably one of the most misguided book titles ever. It doesn't end. The only way to end it and eliminate evil from the world would be to kill all the people, which is probably not the solution we want, although it feels like we're halfway there. It feels like we're trending towards that.
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Jason Calacanis8:21
What is it like doing business in Russia? You were there so early.
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Esther Dyson8:27
I don't want this to be too Russia-focused, but Yandex is a great company. It is focused on finding knowledge and transparency. There's a big difference: censorship in China is 'we're going to stop you from publishing this.' Russia is much more comfortable with arguing rather than silencing.
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Jason Calacanis8:57
It feels like there's a spectrum there. When you look at how angel investing has changed over the years and how the technology industry has changed, what do you think of today's crop of companies and the opportunity for angel investing?
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Esther Dyson9:13
It's so much easier to start a company and so much harder to keep it growing because there's more competition. Unless you're in the rocket business or energy with physical things, you can start with a computer or two and a dorm room mate or two and get started. But the move from being a product with some people and a team to being a company that can reproduce itself, that's the real challenge now.
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Jason Calacanis9:53
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Esther Dyson11:55
I think those are technologies. It's like talking about electricity. It's going to be ubiquitous. The challenge is figuring out how to use it effectively to do something in particular. AI to me honestly is not that useful of a distinction. Everybody's going to be using AI, but until they use it for something in particular, it's... There are AI development kits, a lot of stuff down there. But the first time AI was around, it was very different from what it is today. It was mostly expert systems, logic models. Now much more focus on neural nets and pattern recognition. But there are other things you can do. You can intelligently model stuff. Natural language understanding, again there are different versions of it. There's building an entire ontology of the world so that you actually understand something, or there's now some natural language translation tools where you're just using strings of words and the software does not understand anything at all. It's almost the wrong lens to look at the industry, even though that's what the industry is doing. The technology continues to advance. The applications have been... we haven't had a company built around it, I guess, is what people are waiting for.
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Jason Calacanis13:29
What's going to be the AI company? Do you think that that's a false model, that there's not going to be an AI company that broke out because of AI?
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Esther Dyson13:38
You could say Netscape was the original internet company, but then you could say Yahoo was, or maybe Google. I think it's going to be the same with AI. An autonomous car is very AI intensive, but again, there's no end of history and there's no end of AI.
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Jason Calacanis13:59
How close do you think we are with the self-driving car phenomenon? You have people who think this is 15, 25 years. You have another group of people who think we've kind of got this solved, it's just a matter of regulation in the next 3 or 4 years. Where do you sit? How many of you here do not drive regularly? You mean like don't have a driver's license? I don't have a driver's license. I'm a New Yorker. Have you ever attempted one? Have you ever had one? I've driven a golf cart. How was it? It's a lot of fun. I also drove a Tesla around a parking lot once.
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Esther Dyson14:40
When people think about driverless cars, most of them think of a driverless car versus themselves, and they of course are perfect drivers. So for them, the notion of a car that doesn't have a driver like themselves at the wheel is kind of scary. When I think of a driverless car, I compare it to the people I've sat next to who were texting or talking to me or getting excited, and I'd much rather have a driverless car. The biggest challenge is going to be standardization of behavioral norms so that driverless car B going behind driverless car A can predict accurately what driverless car A will do, even if they come from different vendors. Because then you can in theory pretty much predict everything, including if somebody runs into the street. Driverless car B knows what driverless car A is going to do, how they're going to react. So it's that standardization and then of course regulatory recognition of it that's going to be the most important.
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Jason Calacanis15:49
How do you think that shakes out? Do you think we're going to just see these towns in China or somewhere, or Pittsburgh? The argument is, is it going to be some mayor in Pittsburgh who says, 'Hey, we're going to do this to get attention,' or is it just going to be somebody in China who says, 'By the way, the whole city is going driverless by this date. You can't drive in the city'?
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Esther Dyson16:08
I think you overestimate how fast things respond to the government, even in China. I suspect it's going to be mayors in a bunch of cities, and then it will spread. 10, 20, 30 years?
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Jason Calacanis16:22
Where do you put it in decades? 1, 2, 3?
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Esther Dyson16:25
It's 10% or 40%? I think 10% in 5 years. That may be over-optimistic because I'm optimistic.
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Jason Calacanis16:37
I always like the way I do the betting line: when will the majority of rides in a major American city be autonomous? Because you might have three people in each car, you might have buses, mini buses. There'll be all kinds of configurations. Whenever it is, I think it's going to tip rapidly. Hey everybody, let me tell you about one of our new partners here at This Week in Startups. It's ShipStation. ShipStation.com. It's the number one choice of online sellers. If you're selling online, you know that getting orders out the door quickly is hard. That's why you need ShipStation. It's fast and easy to manage and ship your orders all from one place. You want to keep those customers happy. Whether you're using Shopify, Squarespace, Etsy, BigCommerce, WooCommerce, or any of the other popular selling channels, you should be using ShipStation. It brings all of your orders into one simple interface. It's easy to manage from any device, including your mobile phone when you're on the go. It brings all of those orders into one interface so that you can use shipping labels from all the top carriers: UPS, FedEx, the US Postal Service. They do a nice job over there as well. You can ship more in less time at the best rates available. So let's get to the call to action. This is important for all of you in commerce land. I want you to try ShipStation for free for 30 days, and know that you're going to get that second month free if you use the promo code twist. So go to ShipStation.com before you do anything else, click on that microphone at the top of the homepage, and type in twist. ShipStation, make ship happen. Thanks again for joining the This Week in Startups family. It's great to have a new partner here. ShipStation.com does a great job. Remember to use that promo code twist and give them a little bit of love. Go ahead and try the product. You're going to love it, especially all you e-commerce people out there who have these packages to ship. Commerce is becoming such a huge business, and all these great companies are coming along to support it, including ShipStation.com. All right, let's get back to this amazing episode. I wrote a piece for LinkedIn dated 2024 about these two kids who were teenagers, of course, went and kind of hacked their parents' car so that they could drive it manually, and they went onto the highway with people at the wheel, breaking all the safety regulations. Of course, they immediately got arrested. Was there a career that you wanted to have outside of the one you've had? When you look back, did you want to ever be a science fiction writer or a TV writer? I could see that. It's the most excited part of our conversation. I have this great story. It could be the start of the next Blade Runner. Let's talk a little bit about what you're working on now. I remember last time we talked, you were getting very interested in health and you were interested in cities. You're always kind of pulling different threads to see where they go. What thread are you pulling now?
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Esther Dyson20:13
What I'm doing right now as a journalist, I asked the question, having gotten more and more interested in healthcare. I'm on the board of 23andMe. Why are we spending so much money fixing people when it's too late? As in, car crashes versus why don't we invest in keeping people healthy or in good driverless technology? The reason, of course, is our government systems and our investment systems are all incredibly short-term. But if you do the math and think clearly, if you prevent diabetes for say $5,000 a year, 10 years later you'll be saving $20,000 or $30,000 or $40,000 a year per person. It's just crazy what we're doing. Of course, it's not that easy. You need to change the food supply, change early childhood education, people need to exercise more, without becoming a total nanny state. What we're trying to do, I started a nonprofit called The Way to Wellville. We're working in five small communities, including Lake County which is just north of here and where I'll be going on Monday. We're just kind of simulating long-term policies around early childhood education, parent counseling, changing the food supply, double-up food bucks, mental health support, that kind of stuff. It's a 10-year project to show what it looks like if you do that. It's not a gamble, it's a controlled... but it's not guaranteed to succeed. These are normal communities that want to become healthy, so we're trying to help them do that. They've opted in. They've said, 'Hey, make us healthier.' Then you can try these policies and maybe they'll go to Washington or something. No, they've said, 'We want to be healthier. Come help us do it ourselves.' It is completely not a nice white lady from New York telling you how to live. It's much more, 'We want to do this, but we need help developing capacity.' Nobody from all these great diabetes prevention companies comes and calls on the people in Lake County. These are the neglected parts of the country. The big foundations are giving money to Detroit or to Oakland, not to Lake County. We're trying to, there's five of us on our team, use our connections, our familiarity with things like accountability and management for impact, and help the communities build it for themselves. You've heard, 'Don't give people fish, teach them to fish.' We're helping them build their own fishing schools.
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Jason Calacanis23:22
If this succeeds, what happens? You take the lessons learned, the best practices, and open source them?
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Esther Dyson23:30
They're open source now. We are not doing anything someone couldn't do themselves right now. In fact, Scranton is kind of Wellville number six. It's not so much they're copying us, but we're both doing the right thing. Bill Gates has probably fostered more entrepreneurs than anybody because they looked at him and said, 'He might have gone to Harvard, but he's kind of geeky. I could do that too.' We need women and people of color likewise to create more role models. When I bought my newsletter, I looked at Ben Rosen and thought, 'He's handsome, he's rich, he came from Morgan Stanley, he's a guy, but he's a human being. I could run this thing too.' That's what inspired me to do it. Seeing that other communities have done it, if those jokers in Lake County did that, we could too. So that's one, the community itself. And second, yes, it is government policies on paying for diabetes prevention. My long-run hope, as someone who in theory studied economics, is we can price the cost of sugar, the costs in terms of health and long-term disease, into food products, so some things cost more. We can also price the benefits of education and health. There's a lot of issues around people not having jobs, but football coaches, diabetes coaches, gym teachers, teachers in general, kindergarten people, they should all be paid double or triple what they're getting if you look at the long-term impact of what they're doing on people's overall health. We would recoup it if we hired and paid them better, and trained them better. We need to start investing in people. We're investing in machines, we're investing in all this other stuff. But employers typically now look for experienced people rather than having apprenticeship programs. Society needs to invest in children so that the adults are more capable of taking care of themselves and of not being manipulated by all this stuff that you guys are developing.
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Jason Calacanis25:58
Yeah, come online, it's addictive. It seems like that got away from us, didn't it? It is amazing how much effort is put into getting another 10 basis points of people to click the next ad versus solving obesity. How much of healthcare in this crisis that we're in is directly related to obesity, sugar, diabetes? Is that our biggest one?
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Esther Dyson26:28
There was a really interesting piece in the New York Times which referenced a study. It basically said people typically don't die of diabetes or obesity, but people who have those conditions die sooner of something else. So it's like an accelerator for all these other causes of death. Everybody dies eventually, so to say something as a cause of death is a weird thing. But diabetes and obesity and the related inflammation, heart conditions, and hypertension accelerate death. They are the causes of prematurity of death in a big, big way. They're just trying to figure out those numbers. I've now started studying neuroscience, and I came up with this formulation: addiction is short-term desire, and purpose is long-term desire. The challenge is moving all those dopamine cycles and learning gratification that focuses more on the long term in a society that focuses on the short term. We'll have cookies out in a minute, so just sit tight.
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Jason Calacanis27:51
Thanks for these scrambled eggs. They were great.
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Esther Dyson27:55
We really focus on having protein and vegetables and starting there, then having the other stuff. It is definitely something we all have to take action for. Also, we eliminated plastics. Someone was pushing me on that, so now we do water filters at all of our events and give out glass bottles. We're probably saving tens of thousands of plastic bottles a year between three or four events.
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Jason Calacanis28:21
Let me end on jobs, because it seems like jobs was how Trump got in there, or the fear of jobs or the concern about jobs is a big part of it. We continue to see good employment, wages don't raise. The employment statistics seem massively manipulated by both parties over a long period of time. Wages don't increase, but taxes have gotten lower, we're going to make them even lower, and automation seems very real this time. It seems to me that the 30 million people working in our country in retail and driving people around, those jobs are going to go away, or a very significant majority of them will go away. Are you worried about our society and jobs, or do you think it's like Mark Andreessen was kind of saying, everybody worries about this and it always gets worked out? But that's not always the case.
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Esther Dyson29:16
It can get worked out if we work it out. That's what I'm trying to say. I want to see more people employed with purpose, helping other people to fulfill their purpose. I want more people to be paid more for doing things that only human beings can do, which are fundamentally teaching, caring, supporting, communicating. Separately from that, but not entirely, one of the issues is it's not just about income, it's about income volatility. The unpredictability of earnings creates huge amounts of stress. The unpredictability of work shifts, that's one reason people go to Uber. They can control their time, but they can't control their income. That creates stress, creates inability to plan. If you look at my book list, those three books kind of inform everything I'm thinking about now. One is called 'Scarcity: Why Having So Little Means So Much.' It explains fundamentally what it talks about: poor people and why they seem to do stupid things. It explains that by saying, 'Hey, you person reading this book, you're probably a rich person and you're probably really short of time. Think about the stupid things you do because you're short of time. You double book, you miss your girlfriend's birthday, you juggle appointments. You have a meeting and you have to run out the last 15 minutes. You're thinking, I need to get to this other meeting, how can I politely tell this guy goodbye?' Suddenly it clicks: if I spend 10 minutes here, I can't spend 10 minutes with that person. How many of you, when you buy your latte, think, 'Well, then I can't buy the socks'? For a lot of people, if they pay for the car to be fixed, they can't buy the sneakers for their kid. The kid maybe can survive without the sneakers, but the stress of making those decisions all the time adds up.
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Jason Calacanis31:46
What are the other two books?
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Esther Dyson31:49
I think it's 'The Biology of Desire,' which talks about how addiction is a learned disorder. It's not a learning disorder, but you learn to be short-term. You should read the book. And then the third one is Daniel Kahneman's 'Thinking, Fast and Slow.' For a long time, what's he like? Brilliant, just brilliant. Everything that the book sort of... the books are really, really smart. But if you want to know about the guy, there's another book called 'The Undoing Project' by Michael Lewis. It's pretty great. As opposed to Marc Lewis, who wrote 'The Biology of Desire,' who actually lives in the Netherlands.
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Jason Calacanis32:47
Awesome. Let's hear it for Esther Dyson. Thank you so much.