Chamath on why young people need more agency, risk, and adventure

This Week In Startups is made possible by: Plaud https://Plaud.ai/twist Shopify https://shopify.com/twist LinkedIn Jobs https://LinkedIn.com/twist Northwest Registered Agent https://northwestregisteredagent.com/twist Today's show: *It's another All Star Summer, as we welcome back some of our favorite guests from throughout "This Week in Startups" history. Chamath Palihapitiya's development platform 8090 just raised $135 million, and he's using it to go after a $4 trillion market: the software maintenance, migration, and middleware spending that's currently "pure waste" for enterprises. Find out why the All-In Podcast bestie says every company should use AI to build custom software the way that Google, Facebook, and Meta already do, then go inside Software Factory, the "system on a chip" organizational model, and why Chamath believes AI will allow every human on Earth to start their own company. Guest: Chamath on X: https://x.com/chamath 8090: https://www.8090.ai/ Learn With Me on Substack: https://chamath.substack.com/p/learn-with-me Drink With Me: https://www.drinkwithme.com/age-verify.html All-In Podcast: https://allin.com/ Social Capital: https://www.socialcapital.com/ Relevant Links: 8090 Series A announcement: https://x.com/chamath/status/2071571183665881515 Salesforce Ventures: https://salesforceventures.com/ Craft Ventures: https://www.craftventures.com/ The Production Board: https://www.tpb.co/ WNDR: https://www.wndr.vc/ LAUNCH: https://www.launch.co Coatue Management: https://www.coatue.com/ Jack Dorsey: "From Hierarchy to Intelligence": https://block.xyz/inside/from-hierarchy-to-intelligence Thomas Keller's The French Laundry: https://thomaskeller.com/tfl/ Timestamps: 0:00 It's TWiST All-Star Summer! 1:22 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off! 3:21 Chamath's origin story 7:54 Tom Sawyer entrepreneurship 11:29 Shopify - Turn those What If's into sales with the ecommerce platform powering millions of businesses. Sign up for your $1-per-month trial today at https://shopify.com/twist 16:25 The $5 trillion software market 21:06 LinkedIn Jobs - Hire right, the first time. Post your first job and get $100 off towards your job post at https://LinkedIn.com/twist 25:00 Building "a co-founder for every human" 31:51 Northwest Registered Agent - Get more when you start your business with Northwest. In 10 clicks and 10 minutes, you can form your company and walk away with a real business identity — Learn more at https://northwestregisteredagent.com/twist 35:00 How product development lost its way 45:00 Regulated industries are the beachhead 50:00 Raising the $135M Series A 55:00 8090's "System on a Chip" model 1:04:44 What to tell your kids about AI Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com Check out the TWIST500: https://www.twist500.com Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp Follow Lon: X: https://x.com/lons Follow Alex: X: https://x.com/alex LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis Check out all our partner offers: https://partners.launch.co/ Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland Check out Jason's suite of newsletters: https://substack.com/@calacanis Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups Substack: https://twistartups.substack.com

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  I think you have to have a prepared mind. There are many forms of capital. If you're lucky enough, you can be in a position to allocate time, reputation, influence, human capital.

• 0:10Jason Calacanis?

  If you can productize your passion, you're going to have such great joy in your life. And somebody had put into the waiting that the founders were coachable. All of our money is made with the uncoachable ones.

• 0:19Speaker 00

  Exactly.

• 0:19Jason Calacanis?

  They're supposed to be sharp. They're [bleep] diamonds, folks.

• 0:22Speaker 00

  You can be as successful as you want, but then there's just a lot of people that stop. And then there's a certain core group of maniacs that never stop. You got one trip around the sun, just never stop. Do all the things you want to do, just never stop.

• 0:41Jason Calacanis?

  All right, everybody, welcome back to This Week in Startups. It's the summer. And what do we do in the summer? We do the next unicorns. We think about who are those next companies? And we do the Twist All Stars. Why do we do the Twist All Stars? Because there are some people that share three qualities. One, deep, deep knowledge, experience. They got nuggets of gold. Number two, they're willing to share them. They're iconoclastic. They're outspoken. They will tell you everything. And then number three, they vibe with your boy Jay Cow. They got a vibe. So you're going to get 10 of those this summer. And the first one is my guy, Chamath Palihapitiya.

• 1:21Jason Calacanis?

  I don't want to lose a single gem, a diamond he's going to drop today. So what do I do? I got my plod pin on. Look, it's on my T-shirt, no problem. Press the button, I get the haptic, it's recording, organized in my plod using AI. And I'm just going to give it an instruction of top. Hey, make sure I take these into action items and analyze them against my three businesses. The Syndicate, my fund and programs like Launch Festival and the Launch Accelerator, and against my media business, This Week in Startups, This Week in AI. Take Chamath's knowledge and analyze my businesses with every drop of knowledge he does. Now that's in my pen. I just had this idea, take Chamath's knowledge and put it against my businesses.

• 2:06Jason Calacanis?

  Huh? It's like getting Chamath as a consultant. And that's all enabled by Plod. You have to applaud Plod for making such a world-class device. There's some folks who you just love as the twist audience, as founders. They typically have three things in common. One, deep expertise. Two, willingness to share it candidly. And third, a vibe with the host. We got, you know, the vibes are immaculate. Top of that list is my bestie Chamath Poliopetia, who's making his fourth or fifth appearance here on This Week in Startups. And my Lord, we've done 260 episodes of All In as well. It's crazy, huh?

• 2:42Speaker 00

  What's up, bestie?

• 2:43Speaker 02

  This Week in Startups is brought to you by Northwest Registered Agent. Get more when you start your business with Northwest. In 10 clicks in 10 minutes, you can form your company and walk away with a real business identity. Learn more at northwestregisteredagent.com/twist. LinkedIn, thanks to our partners at LinkedIn. Post your job for free at LinkedIn.com/twist, then promote it to get access to LinkedIn Jobs' new AI assistant. And Shopify, turn those what-ifs into sales with the e-commerce platform powering millions of businesses. Sign up for your $1 per month trial today at Shopify.com/twist.

• 3:21Jason Calacanis?

  So to kick us off, one of the great jokes I would have to tweak Chamath, one of the few things I could tweak him about. No, not his fashion, no, not his shopless selfies.

• 3:33Speaker 00

  Not my swell body and rock hard abs.

• 3:35Jason Calacanis?

  None of that. It was the fact that, hey, a decade ago, he was one of the few of us who hadn't started a company. Well, now that's changed dramatically.

• 3:44Speaker 00

  What do you consider social capital? That was a company.

• 3:46Jason Calacanis?

  I mean, starting a firm is all very close to starting a company, but slightly different. A firm is slightly different than a company because you don't have exactly customers, products in the same way. You're managing assets, right? I consider it adjacent, right? I don't know how you feel.

• 4:03Speaker 00

  Founder adjacent. How is founder adjacent?

• 4:04Jason Calacanis?

  It's founder adjacent. I mean, you could be the founder of a fund, but really, making a product or service is hard. Since that time, I was just thinking about it before I got on air here and I was walking down the road at the ranch. You've been in a flurry. People don't know, but you have two wonderful products that I love the branding on. Drink with me, or us, it's drink with me, and then learn with me. What I love about those two products is your passion, learning and wine. And number two, the branding. I've never heard anybody do blank with me. Where did that come from?

• 4:37Speaker 00

  There are things that are omnipresent in my life. I just thought that there was a clever way to make a business out of it. And maybe you would say, why? Like, what is Learn With Me? Learn With Me is just a research community. So, you know, part of my job at Social Capital, and part of my job in general, is to be a very thoughtful allocator of capital. And, you know, we'll talk about this when we get to 80, 90, but there are many forms of capital that if you're lucky enough, you can be in a position to allocate. One is time, another is reputation, another is social capital, so influence, another is human capital, you

• 5:21Speaker 00

  know, influencing what other people work on. And then the last is capital capital, just money, right? But in order to do that job, and I think it's an important job to be a capital allocator, I think you have to have a prepared mind. In the late teens and early 2020s, I was introduced by a friend of mine who was a senior partner at McKinsey, at the time, now he works for Google, to this service that they had for certain people. And at the time, how he sold it to me was, this is the team that teaches Bill Gates about things when Bill Gates wants to learn about something. And so I hired them and I said, okay, teach me all things energy. Because I wanted to understand climate change, but I really just wanted to understand energy production. And that was, you know, year

• 6:06Speaker 00

  five of Grok. So, you know, I could kind of see the forest from the trees on AI silicon and what was happening in power. And I just felt like I didn't know anything about it. They did an incredible job, but they also charged me $4 million for three months, or $2 million, $3 million, I don't know, something. It was a lot of money. It was many millions.

• 6:29Jason Calacanis?

  Right.

• 6:30Speaker 00

  And so I just created a team for myself. And I said, you know, I want you guys to create a calendar and create first principles materials that I can use to learn about what I need to know about in the current moment. While they were able to do it, the biggest thing that I struggled with was what if their content is wrong and or not good?

• 6:52Jason Calacanis?

  Right.

• 6:52Speaker 00

  And the solution that we both came up with was, okay, let's make it a subscription service and let's make the cost meaningful enough that it's a real signal. So, you know, there's a community now of many thousands of people. The cost is about a thousand bucks a year, but it's all the content that my research team produces that I use to frame my point of view. One day it'll be, you know, lab grown meat. The next day it'll be about China. The next day it's about religion. The next day it's about semiconductors. The next day it's about AI models. The next day it's about attention mechanisms. The next day it's about mining. But if you start to consume it on a regular basis, you, you really do start to develop a prayer mind. And because there are so many thousands of people now that consume the service, the single biggest indicator of value is churn.

• 7:36Jason Calacanis?

  Yes.

• 7:37Speaker 00

  When people are churning, it just means the content sucks. And so I know that something's wrong. And when the service is growing, it's the most simple way of me being able to judge whether the content is timely and accurate.

• 7:49Jason Calacanis?

  Right.

• 7:50Speaker 00

  That was, that's learned with me and that's, you know, available to anybody who wants to sign up.

• 7:54Jason Calacanis?

  I tell you what's so brilliant about it is you, you learned a really great, um, what I call like a Tom Sawyer version of entrepreneurship, which is, you know, he had to paint the fence or was it Huck Finn? It was one of the two. And he said, hey, painting the fence is a lot of fun. If you guys give me an apple, I'll let you paint the fence. And people would come and paint the fence with him. You took something that was a cost center. Yeah, it was Tom Sawyer. You took something that was a cost sensor. You then brought a community into it so they act in two ways. They validate it. They make sure the information's correct, but you took something that's a $4 million, you know, money pit. And now you own this, you get to direct it, you get to have those employees and it makes a couple of million or who knows what the break even point is based on the number of people are working on it.

• 8:38Speaker 00

  And the team actually makes profit from it. So, meaning, you know, it's not where I'm going to sort of define my upside, but it's great that the team has the ability to actually build a, a business and a community around something that I really value. And it seems like many thousands of other people also value. How big could it be? I don't know. It's probably, you know, in the grand scheme of things, probably a reasonable thing for tens of thousands of people to sign up for, maybe 100,000 people.

• 9:08Jason Calacanis?

  I mean, tens of thousands of people signing up for a data product would put you in the most elite circles of data products. Like the information broke 10,000 at some point, right? It's a third of the price and it's more journalists than analysis, but you know, there are corollaries to that. And if you can take something you're doing anyway, and Tom Sawyer it, I did that with podcasting. I was going and having lunch with you and having a great conversation for two or three hours. And it was like, hey, turn the cameras on. Why don't we share this with people? That's what drew me to podcasting. And then all of a sudden it was profitable. Oh my God, this opens up so many doors and you get that correcting mechanism. You're bringing a bunch of folks. We'll get to 80, 90 in just a minute. Big announcement coming up.

• 9:46Speaker 00

  Yeah, then, and then drink with me is completely different. So, you know, look, I, I guess you can read all the health stuff you want and, you know, I just think at the end of the day, people have to decide what quality of life do they want? And, you know, the years that I have on this earth, I want them to be enjoyable in a way that matters to me. You know, I could sleep separated from my wife in a bed at 68 degrees and maybe live an extra six months, but I'm not sure it's worth it for me. And that's just my own personal trade off. Similarly, you know, I could live calorie restricted and probably be a little bit fitter,

• 10:26Speaker 00

  but then I would have to say no, or disappoint my children when they say, let's go to the ice cream parlor. Let's walk down the street. Hey dad, try this. I just made this. I know. So similarly, wine for me, you know, I drink it once a week, but it's a very special, social

• 10:47Speaker 00

  thing in many people's lives.

• 10:49Jason Calacanis?

  And it's rich culturally. You get it.

• 10:51Speaker 00

  Culturally super rich.

• 10:52Jason Calacanis?

  And also socially, right? Like I know when I've opened bottles with you, it's like so much fun to learn about the wine together.

• 10:58Speaker 00

  I've gotten you to drink white burgundy.

• 11:01Jason Calacanis?

  Yeah, love it.

• 11:02Speaker 00

  You know, where you've never drank alcohol basically in your life.

• 11:05Jason Calacanis?

  Yeah, I was never a big alcohol guy, but I love having a couple of ounces with you. Yeah, it's fun.

• 11:09Speaker 00

  So what I, what I noticed about the alcohol business is that wine is incredibly marked up. And the reason is from the winery. So you know, wineries, by the way, there are two properties of wineries that everybody should know. The first is that they are incredible artisans. These are farmers and scientists.

• 11:28Jason Calacanis?

  Did you know you can set up your own drop shipping business easily with Shopify? Imagine running an online store, selling whatever you like without having to worry about inventory, shipping, or, you know, paying for space in a warehouse, which means, yes, all you need to do to get started is pick a product category, find a supplier, and set up your Shopify store. All the infrastructure you need, from third-party apps to Shopify's seamless checkout process is already in place. So you can just start moving units in just hours, not weeks. That's why we're creating a This Week in Startups merch store, and we're going to use Shopify. Shopify is the e-commerce platform behind millions of businesses around the world.

• 12:12Jason Calacanis?

  In fact, they're powering 10% of all e-commerce in the US, from household names like Kynes and Mattel, to companies that are just getting started like yours and mine. It's time to turn your what-ifs into... Sign up for your $1 per month trial today at Shopify.com/twist. That's Shopify.com/twist.

• 12:31Speaker 00

  They slave away, quite honestly, to make something by hand. You can't automate it. You can't AI this. And I think that that's beautiful, that that property is beautiful. And the second is, you will never find a winery in an ugly part of the world. They are in the most beautiful parts of the world. So you have these people that get the benefit of working in these incredible places, making something with their hands. But the minute that that product is done, it enters this middleman renter economy that marks things up. And so by the time it gets to you, it's typically twice the price. And there's a lot of gatekeeping that happens.

• 13:14Speaker 00

  And that gatekeeping creates artificial scarcity when it shouldn't. And it allows, you know, certain people with certain kinds of wines um to make a killing. And that annoys me because I don't, I don't, I'm, I'm happy to stand in line. Um, but I don't like being part of like some rigged game.

• 13:32Jason Calacanis?

  I hate it. It's the worst feeling ever. When I tried to buy, when I first saw Weblogs Inc. AOL, when we were at AOL, I wanted to go buy a Ferrari. And the amount of torture they wanted to put me through. You gotta buy a used one for a hundred K off a sticker. You gotta buy the one you don't like, and that's a dog. You buy two of those, then you can buy the one you want. It's just annoying. And I just ran into the same thing with the watches, you know, just looking at watches. They're like, oh, boy, here you go. You gotta find a middleman. And there are these three watches that sell direct, but most don't. So you find this annoying, irritating sand in the oyster. And then the pearl comes out. Yeah.

• 14:05Speaker 00

  I think so. I just think the people that make the wine get a bit of a raw deal. And at the end of it, there's a lot of generational transition that's happening where most winemakers are hitting the end of the road where their children do not really want to take over these things. And so what happens is they sell to a corporation and then the product goes to complete and total shit. So I said, I can do one of two things, which is I can go and just get my own liquor license. So I can collapse the middleman renter economics of the business. And I can create a community so that other people who would like to buy it can also buy, using the same discount that I can now get, which is, you know, upwards of 40% sometimes.

• 14:45Speaker 00

  But the real goal is that to build enough relationships and trust with these winemakers so that when they sell, they don't just sell to some nameless, faceless organization. But they could theoretically go to us and a community of people that love what they do, sell a portion to us, be able to do some estate planning. You know, find great other people who are young and up and coming to help take over their winery and keep these things going. And look, again, like Learn With Me, neither of these were meant to be billion dollar businesses. They're just meant to be parts of my life that give me tremendous ROI.

• 15:26Speaker 00

  And I think that there's probably many other people for whom that is the same, where, you know, you can. Kind of create a perpetual kind of flywheel out of it and see things going. So that again, it's, it's not just all corporations that, that just kind of treat everything like a number and a cell in a spreadsheet.

• 15:49Jason Calacanis?

  Yeah. I mean, this is one of the great lessons. If you can productize your passion is what I tell founders. You're going to have such great joy in your life because you're going to look at something that was a cost center. And you had to go make money doing something you hated to fund the passion. But if you can align that and you've productized your passion in some way. And then you get this ROI. Okay, sure. Maybe it makes a little money on the side. It's not comparable to what we do in day jobs, but it's nice. And the same thing with the podcast. All in has a nice events business now. We'll talk about that in a minute because that's the third business that you famously started. Give you a lot of credit for that. You called me after coming out of CNBC one time and you're like, one, I miss you COVID. Two, I can't do these three minute hits and not get my point across. Why don't the two of us just chew the fat and I'll come on this week and start.

• 16:34Jason Calacanis?

  She says, no, I want to do something different. And that was the origin story. And then we of course, got the two Davids in there and got those two nerds nerding it out to, to counterbalance our.

• 16:42Speaker 00

  And we made, and we made, I made this key decision, no ads ever.

• 16:45Jason Calacanis?

  No ads ever. Another great one. Yeah.

• 16:47Speaker 00

  Which, which was very smart because it, it pulled us into other businesses. But yeah, so look, there was a period after COVID. If I look back on it, I'm quite proud of the three businesses that I've helped co-found. And it was a moment in my life in my late 40s. Where I was honing in on, you know, what am I, you know, what am I?

• 17:08Jason Calacanis?

  Yeah. Who am I? What am I? The big question when you're successful, right? Yeah.

• 17:11Speaker 00

  Yeah. And, and it's like, you know, like I, I know like what drives me. It's like I have, you know, relative mistrust of institutions. I have a relative mistrust of experts. I really like to do my own diligence. I think from first principles. I'm not afraid to be wrong. And that's when I honed in on, I'm, I'm this allocator of capital. But the thing that I had never done. In all of this journey, since Facebook was really allocate my time to one thing. I'd allocated money, I'd allocate reputation, you know, I'd allocate social capital and influence. I'd convince people to go and work at companies on behalf of my friends or on behalf of

• 17:51Speaker 00

  the things that I was an investor in, but I've never put all of that together into one thing.

• 17:57Jason Calacanis?

  Yes.

• 17:58Speaker 00

  And that's sort of where eighty ninety came from. Because, you know, I would always like, I kind of felt at the tail end of COVID, like, okay, this AI thing, you know, I would tell my friends and my family, it's like, I'm out there waiting to ride a wave. And I've been lucky in that I've ridden two huge waves in my career. Wave one was the beginning of the internet. You know, you rode it with me, we were, you know, I was at Wynn Amp and then I was at AOL. And, you know, I had the luck of learning about network effects at AOL. And then I accidentally swam into a second huge wave, which was mobile and social.

• 18:39Jason Calacanis?

  And social, yeah.

• 18:41Speaker 00

  And, you know, my real chops were made creating growth as a craft and then, you know, just automating and instrumenting and machine learning the shit out of it. That was a huge success for Facebook, but then I kind of sat out the SaaS wave.

• 18:56Jason Calacanis?

  Extremely tactical, extremely strategic. And this is, I think, what really made you dangerous is that you added that tactical, strategic and team building philosophy and skill set to your skill stack.

• 19:12Speaker 00

  You know, the thing, the thing that I'm the most proud of at Facebook is I recruited a team of seven people. It was called Growth Circle. Three of those people are still there and they're CXOs of the business. They're the COO, the CMO, you know, I did a good job of managing people and recruiting them and mentoring them, but I'd never had the itch to do it since then.

• 19:35Speaker 00

  And part of it was, I think, my intuition that the waves weren't big enough. And then this AI wave started to build and I was like, this is it. I just got to paddle out, get on the board and just rip it.

• 19:46Jason Calacanis?

  Yep, figure it out. And that's 80, 90. What was the origin story there? Because I think most people know what you're doing if they're fans of All In and they've heard us chit chat about on the side. But let's start from basics. What does the company do? How does it make money? And what's the origin story here?

• 20:03Speaker 00

  I like to write things down because I think it's like, it keeps everybody honest.

• 20:07Jason Calacanis?

  Writing is clarity of thought. Like, that's what writing is. It just clarifies your thought perfectly.

• 20:13Speaker 00

  I wrote a product spec for something that I called Co-Founder. And the idea is, why can't everybody in the world have an incredibly capable co-founder? And why couldn't there be as many or more companies as there are people? Now, bear with me for a second. If you go all the way back to, let's just say, the 15 or 1600s, there was hundreds of companies. And I'm sure if you go back many hundreds of years before that, there was probably the one moment where the first company in the entire world was created.

• 20:55Speaker 00

  But from that one, ultimately grew to hundreds, which ultimately now, I'm going to assume there are tens of millions of companies in the world. Maybe hundreds of millions of companies.

• 21:05Jason Calacanis?

  Yeah, it's definitely tens of millions, for sure. Adding a new member to your team is a crucial decision. And you don't want to rush into a hiring situation that you will regret. But if you're a busy founder, you also don't want to spend a ton of time in the trenches looking for that perfect candidate. Instead, you need a partner and you need a trusted partner. And LinkedIn Hiring Pro is that partner. How do I know this? Because I use LinkedIn Hiring Pro. You want a real-world testimony? All right, here you go. We recently hired a new customer success manager. They handle all the advertising accounts here on This Week in Startups. And they ensure that we're keeping all of our wonderful partners happy. LinkedIn helped us connect with an amazing candidate. Right here in Austin. And he had exactly the combination of experience we were looking for.

• 21:50Jason Calacanis?

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• 22:05Speaker 00

  So the trend is inexorably in one direction. But in order for you to go from 100 million companies to say 10 billion companies, what you needed and what you will need is something that helps you fill in for all the weaknesses that you have. And I called that co-founder. And so the idea was, what if your co-founder could, you know, when you said, I'll just use a very simple example. I want to open a flower shop, very legitimate business. And your co-founder says, great, I'm going to spawn these 19 different processes. One is going to do a market analysis of where in our city is the best traffic patterns for demand.

• 22:47Speaker 00

  Another agent will then ping all the commercial real estate agents and ask it, what are the available spots in all of these different geographic corridors that the first agent identified? The third will go and do a crawl of the internet and give me back a market summary of the kinds of flowers that one would need. The fourth will go and ping Stripe and activate a Stripe merchant account. The fifth will go and, you know, work with SpotOn to get a terminal delivered to my storefront. The sixth will engage a construction crew to do the kit out of my store. The seventh will be a supply chain agent, right? So you can go on and on down the line. And then you can imagine if instead of saying that, instead you said, I want to build an airplane company.

• 23:32Speaker 00

  Maybe it's not 10 agents, maybe it's 10,000. But the point is that there can be a conductor, an orchestrator at the absolute top level, who can help you execute on all of those things. That's where I originally started and the spec that I wrote. The problem was that the market was not ready for something like that. And my best guess, when I read it over and over again, is that's a 30 year or 40 year journey. So then I had to wind it all the way back and say, what is a logical starting point today? That over time can earn our way into being that omnipotent co-founder for every human on earth. And, you know, maybe just to double click on that, why that?

• 24:15Speaker 00

  Because I think for me, this idea of enabling economic mobility, giving every single human on earth the ability to be economically independent, self-sufficient, take care of themselves, take care of their family, have money to spend on the things that they want. That to me is a very powerful idea. It's an extremely decentralized view of capitalism and democracy at scale.

• 24:38Jason Calacanis?

  Yes.

• 24:38Speaker 00

  So to seem like, you know,

• 24:41Jason Calacanis?

  Big audacious mission, right? Yeah. And if you look at what's wrong with America today, in our great journey as a capitalist society, is self-reliance has been replaced in some ways with, you know, victimization and handouts have replaced pulling you up by your bootstraps and agency. And what you're talking about is, you know, basically reconnecting people with that.

• 25:05Speaker 00

  Yeah.

• 25:05Jason Calacanis?

  What the pioneer spirit of this country and as an immigrant to the country and somebody who had to fight for tooth and nail for everything you got, which, you know, people take for granted when they meet you in the circa 2020s. You know, I know the story. You had to fight every inch. So if you have to fight for everything, you really want to see other people have that opportunity. It's the clearest path to fixing this K-shaped recovery, the issues we have that we talk about on All In Every Week is just to empower people to start their own companies.

• 25:33Speaker 00

  Yeah. Then I had to kind of say, okay, if that's where I want to be, where do we start? And, you know, I learned two really incredible facts. The first is that if you look at the world's GDP, call it, you know, for the purposes of this conversation, $130 trillion, I would say 90% of it requires some sort of technology to make it come to life. Some sort of software of some kind. There's a certain percentage of the GDP that does not require that.

• 26:05Jason Calacanis?

  Yeah, increasingly smaller and smaller.

• 26:09Speaker 00

  Yeah, increasingly smaller and smaller. So it's kind of what Marc Andreessen said. Software really is eating the world. So that was one interesting factoid. And the second is when you look at software, what I learned was software can be bucketed into two categories. It costs around $5 trillion a year. So think about as $5 trillion enables, call it $100 trillion. Okay, so there's a 5% take rate. That software extracts to enable most of the GDP of the world. And that 5 trillion can be further subcategorized into a trillion dollars of licensing revenue.

• 26:46Speaker 00

  So this is what you would pay Workday or ServiceNow or Jira or Linear, GitHub, whatever, right?

• 26:56Jason Calacanis?

  Yeah.

• 26:57Speaker 00

  A trillion dollars of those licenses. And then $4 trillion of maintenance, migration and services. So meaning, once you implement Workday, you typically bring in a suite of consultants to just help you make sure it doesn't break all the time.

• 27:15Jason Calacanis?

  Yeah, and that you get your value from it because somebody has got to make sure the the distance between this huge contract that was signed by management, some CTO somewhere, actually gets implemented and it's worth the money you've spent on it. Or else somebody loses their job eventually. It might take five years, but I remember when I was in IT, this was an acute thing, like some top down person was like, hey, we're going with Lotus Notes. And then it was up to us to make sure Lotus Notes actually delivered the value, not Lotus Corporation.

• 27:43Speaker 00

  So, but, but it occurred to me when I looked at that, because I'd not really looked at that very carefully. I had this kind of like light bulb moment, which is I contrasted that to what we had done and a lot of what my team had built at Facebook. And I thought to myself, well, hold on a second.

• 28:01Speaker 00

  Why is it that Facebook, which is an exceptional business, only uses an extremely small amount of that $5 trillion? And most of it was built internally. And then I remember what I had learned from my friends at Google, and it was the same thing inside of Google. And then I remember what Elon had taught me about Tesla, same thing at Tesla. You had all these examples where, at the extreme end of success, all the best companies

• 28:31Speaker 00

  almost had an allergic reaction to that traditional software stack. They refused to use it. And so the light bulb moment for me was, oh, I understand. Like, imagine, Jason, you and I both want to start a restaurant. And we're given ingredients. We both get sesame seed buns. We both get three burger patties. We both get tartar sauce. We both get the same pickles. At some point, you're going to start to wonder to yourself, how do I differentiate myself from Chamath's Burger Company?

• 29:03Jason Calacanis?

  Yeah, source better meat.

• 29:04Speaker 00

  And you're going to say, I'm going to source my own ingredients. I'm going to make these things myself. And I'm going to take the risk because I think there's better margins and better success in doing it my way. But for most companies, even though they say that on the surface, underneath, with respect to the software that they use to run themselves, it is exactly the same. That is why companies like SAP and Oracle can be as big as they are. They've structured and standardized this idea that at a certain level of scale, the only solution is their solution. But I had seen firsthand, and I had enough friends and examples

• 29:48Speaker 00

  of other great companies that took a different route. Now, normally, you would say, okay, but that means nothing. Nobody's going to, you know, how do you go to a defense contractor and all of a sudden convince them to make custom software? They can't do that.

• 30:02Jason Calacanis?

  No. They've got other things on their plate.

• 30:05Speaker 00

  Yeah, I would have agreed with you until AI.

• 30:08Jason Calacanis?

  Right.

• 30:08Speaker 00

  And the reason is, you saw, I saw this cost curve where the unit cost of production.

• 30:15Speaker 00

  Was going to approach zero. So there was no task that was either too menial, too manual, too repetitive, or too difficult. So both ends of the spectrum that couldn't be accomplished at some point by these models based on how fast they were accelerating their learning.

• 30:31Jason Calacanis?

  Right, that was what you saw just around the corner was, hey, this vibe coding stuff, which people are dismissing, hey, this is bullshit, it's just stupid. It actually was, if you tracked it and you used it every month, you could see every two or three months that it made some significant leap forward.

• 30:49Speaker 00

  I, my thought was that vibe coding was going to be a great way to realize what the art of the possible was, but end up with a bunch of trash.

• 30:57Jason Calacanis?

  Like prototypes, basically.

• 30:59Speaker 00

  At best, but probably not even that.

• 31:01Jason Calacanis?

  Proof of concept, yeah.

• 31:02Speaker 00

  And so in the first instantiation of 8090, I said, we have two goals. Goal number one is let's help companies get the margin benefits and the upside of the kinds of custom software that companies like Facebook and Tesla and Google benefit from, number one. And number two, along the way, how do you create a mechanism of learning? The kind of data that can be collected by that process, by the unbundling of that process? So that incremental runs of software become safer and faster and simpler to build. So first is do a job.

• 31:45Speaker 00

  Second is try to orient and create a network effect and a flywheel inside of doing the job.

• 31:51Jason Calacanis?

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• 32:31Jason Calacanis?

  So get all the advantages of a Delaware C corp, independent, regardless of where in the U.S. You're operating from. Visit NorthwestRegisteredAgent.com/Twist for more details and the links are in the show notes.

• 32:44Speaker 00

  What we did was we created a product and we called it Software Factory. Because we felt like that was a very honest representation of what this V1 goal is. It's just to create a factory that makes software. And we thought it could give value in both of those ways to people. So let me explain. So Software Factory is exactly what you think of if you went to a Tesla Gigafactory. Raw material comes in the front, finished Teslas come out the back. And in between, there are all these very logical stations and different tasks are done at these stations.

• 33:25Speaker 00

  In our case, what comes in at the front is just pure raw intention.

• 33:32Speaker 00

  And that can be for the kinds of business people and senior leadership of a company. That, you know, deals in high level business requirements, you know, McKinsey decks.

• 33:45Jason Calacanis?

  Whatever your business is, that whatever your business goals are.

• 33:47Speaker 00

  Regulations, you know, new laws get passed, you know, maybe say it in a, in a different way. A consent decree that you get from the U.S. Government, whatever. The point is that at the senior level, you know, you're managing risk and you're allocating capital towards ideas. You want to give a shape to that and then you want to be able to put that in the part, in the front part of the factory. And have your colleagues and your teammates and the people that work for you. Extract from it a, a pretty detailed PRD, right? A product requirement stock.

• 34:18Speaker 00

  And what's great is it's not just the humans that collaborate on that. Now you can have agents working behind the scenes to make that PRD incredibly high fidelity.

• 34:28Jason Calacanis?

  And those PRDs at AOL was where you learned it. Yeah, like they were big on these PRD docs. They were huge.

• 34:35Speaker 00

  By the way, you're bringing up a very good point. Like when I talk about the software factory, what it is, is an embodiment of what people call the product development lifecycle or the software development lifecycle. They're interchangeable terms. The reality is that PDLC and SDLC lost its way. It gave way to a lot of what we created at Facebook in terms of an engineering driven dev culture, which is move fast, break things, build first, poor documentation. And you know, when we did that, we did that in a very specific moment in time, not because we cared about those words, but we were the, you know, 35th social network on the scene.

• 35:16Jason Calacanis?

  People forget, yeah, there were like many before MySpace, etc.

• 35:20Speaker 00

  We had all these giants above us, including Friendster, including MySpace. You know, we didn't have money. And so we had to move fast.

• 35:28Jason Calacanis?

  Right, that was your advantage.

• 35:30Speaker 00

  But now engineering organizations start up with this idiotic idea that you shouldn't document, you should just wing it, you should just grip and rip this stuff.

• 35:39Jason Calacanis?

  And don't write anything down and then what happens?

• 35:41Speaker 00

  You get a lot of crap that gets into prod. You have an enormous amount of tribal knowledge. It's unfortunately trapped in many humans' heads. It's not well documented. You have no SOPs. So when things break, things get really bad. Why not have a system where intent comes in the front? You can shape it, humans, AI, agents. And then when you lock that down, Jason, the next most important step is to extract from it a very detailed, what we call an engineering plan or a blueprint, right? Like when you sketch out a house, the next step is you give it to the architect and say, "Give me the buildable blueprints."

• 36:20Speaker 00

  Which give you all of the little technical details so that the house can stand on its own. The foundation is strong, all the wiring makes sense. And so our module, that step in our software factory, you know, allows you to do everything from right, you can upload, you know, Mermaid diagrams, you can do anything that you need to represent the system. And then when you lock that, only then can you do what most people go right to doing right now. Now, look, you can skip these steps, but we don't recommend it. The third step is you extract work orders. And this is where now, you know, vibe coding failed. If you could direct an agent

• 37:03Speaker 00

  to code with relatively strict guardrails, the agents are excellent. You've experienced this in some of the projects that you're doing. But the reason, I suspect, is because you specked it cleanly and precisely.

• 37:17Jason Calacanis?

  Yeah. And the more you give it, the more precise it becomes. It's a very counterintuitive thing. You would think that a stream of consciousness and rambling and throwing everything at it would create chaos. These machines are very good at taking a large set of feedback and actually making sense of it and making a plan out of it. It's kind of actually its strongest, its strongest ability right now. And so this is why I have the foot pedal, because I just, when I do a prompt now, I hit the foot pedal and I just keep talking and talking and talking and talking, let it go. And then it makes sense of everything I said. And then it asks follow up questions, because I ask at the end, ask me any follow up questions, but what's not clear or things I'm

• 38:02Jason Calacanis?

  missing and, you know, blind spots I might have. When you do that pedal to the metal strategy, boom, everything changes, which I think is your refinery thing, which is, hey, we're just going to pull in all of your stuff.

• 38:13Speaker 00

  Yeah, refinery, like, again, exactly, right at the front, our thing is, you just dump everything, Zoom meetings, whatever, we'll sort through it for you and we'll give you a spec of a PRD. And now you can be there collaboratively in multiplayer mode, in one dock.

• 38:30Speaker 00

  Debating, questioning, asking, approving, denying. And then you go to an engineering plan. And then you go to work orders. This is the same as a GitHub issue. And then you can send it to a coding agent. And we support all of them via MCP. So you can use cognition, you could use Codex, you can use Claude.

• 38:48Jason Calacanis?

  Cursor, whatever.

• 38:49Speaker 00

  You can use cursor, you can use whatever you want. And by the way, the reason we support those is our view is all of those vertical tools are going to converge. That's not where the skill is.

• 39:01Jason Calacanis?

  It's all going to reach parity is what you're saying.

• 39:03Speaker 00

  Yeah, they're all going to be the same.

• 39:04Jason Calacanis?

  Plus or minus, whatever.

• 39:06Speaker 00

  The real skill is being able to keep this whole system in sync. Right? Because then when you make the code, how do you generate evals? How do you generate unit tests? How do you wrap those together? And then how do you get it into prod and then maintain it as a system? So for example, you build a product. I'll give you an example of one of our customers, regulated healthcare company. And with the triple B, a law changed. They just feed that into refinery. We understand the diff between that PRD and what needs to happen to respect the law. And once that's approved, it gets auto propagated into the engineering plan, auto propagated into a set of work orders. Humans review and approve them.

• 39:51Speaker 00

  And then put into the code because an agent goes and writes it. And now the system is completely in sync.

• 39:58Jason Calacanis?

  Yes.

• 39:59Speaker 00

  The biggest problem that companies have is the drift that happens, right? Everything gets out of sync. By the way, it also works in reverse. So we built the factory so that it can work in forward or reverse. So for example, an engineer gets a pager duty, wakes up at 3:00 AM in the morning. They all of a sudden have to like, you know, fix a bug or patch something and they put production code in. We detect that. And now we auto propagate the work order, we auto make the change in the engineering plan, and then we make the change in the PRD. So now, everything is, everything is linked together. We call that binding. Everything is binded together, so that everything is in sync.

• 40:42Speaker 00

  Now, that may seem like overkill for a small product, but when you go to the big guys, and you talk about what they're dealing with, they're not here to fuck around with some stupid vibe coding tool. Like, this is the, this is the level of governance and auditability that they need. Why? Because if you think about the kinds of products that many of our customers make, they're in highly regulated markets, they have, you know, huge upside for doing it, but they have huge risk as well, Jace.

• 41:09Jason Calacanis?

  Yes, you have to mitigate, like, as a finance, healthcare, education, any of these verticals.

• 41:15Speaker 00

  Pharma.

• 41:16Jason Calacanis?

  Pharma. You make a mistake.

• 41:17Speaker 00

  Defense.

• 41:18Jason Calacanis?

  The blast radius can be large.

• 41:21Speaker 00

  Yeah.

• 41:22Jason Calacanis?

  And can take years. Look at, I mean, your time at Facebook, I don't think you were there for all of it, but they've, they're under three, they've been under three or four consent degrees for mistakes made, speed errors, whether it's fair or not, whether it's political or not, put it all aside. It all speaks to, you know, having a tight plan, having this harness, people are calling it, having the software factory allows you to trust the AI more, and it allows you to feel less chaotic. Control plane, yeah.

• 41:49Speaker 00

  The reason we call it a control plane is like, it's a plane that sits, you know, above all the fray, all the chaos. You know, models will come, models will go. We work with all of them. We allow ourselves to be able to take advantage of the best-in-class model for the best in task, for the best task at that time.

• 42:08Jason Calacanis?

  Yeah.

• 42:09Speaker 00

  But it mostly is a product that's about multi-user, collaboration, control, governance. And then, what I told you is, this emergent property where...

• 42:21Speaker 00

  Whenever you're building these products, we sit it on top of a knowledge graph. And what that is, is this is very similar to sort of the architecture that I had in mind at Facebook. And the architecture, when we led the series A in Slack, you know, I wrote this memo for Stuart, which was called intercompany edge effects. You know, like, I don't think I'm like head and shoulders better than anybody at most things, which I'll be told, but there is one thing where I've just been in it for a lot longer than most people, and I see these patterns, and that is around network effects. And so this third time around, I wrote the PRD for this network effects, and how to build it and architect it.

• 43:06Jason Calacanis?

  At Slack specifically?

• 43:07Speaker 00

  No, no, here at 8090, yeah. But I'm saying it's built on the experience of Slack and it's built on the experience of Facebook. And what I see is this ability to use the nature of these models to help improve the N plus first piece of software based on its experience building the N pieces before it. I don't want to give too much of that away, but that's working too. So basically what we have, Jason, I guess in a nutshell, is we've created a factory. It gives companies a lot of control. It allows them to document things. It allows them to take out of tribal knowledge, what is in humans' heads, and document it for the first time in a long time.

• 43:49Speaker 00

  It allows these systems to stay complete and in sync. It allows them to unbundle a lot of that $5 trillion they're spending, and slowly but surely, kind of, you know, how do you eat the elephant? One bite at a time? It's like, okay, I'm going to take a shot at this specific workload. Oh, great. So, you know, for example, like today, there was a guy that tweeted, you know, that this is a third party. And he said, we've, you know, used Software Factory now to unbundle $5 billion of ISV licenses. $5 billion.

• 44:27Speaker 00

  And I saw that and I was like, man, this product works. This is great.

• 44:31Jason Calacanis?

  Yeah, I mean, you have product, you've got the signs of early product market fit, which means you'll get to pull eventually where people will just be like, I need this. And what people don't realize is in those large companies, there's a long list of projects they would like to work on. They have two choices generally. They can hire IBM, they can hire a software company, then they have the implementers they can hire alongside the McKinsey or Ernst & Young, whoever it is. And now you're giving them a third way, which is, hey, are you smart enough to use these new tools to control your destiny? And then take those middlemen, we're talking about the middlemen in wine, and those folks, like, are they actually adding value or are they damaging the core brand? And you would, you could argue, and you know, for every time one of these implementations

• 45:15Jason Calacanis?

  happens, and we saw it off close and personal, it was a waste of money and didn't get used and gets thrown away, or it's just years of frustration and you lose anyway. Here, at least, you're getting closer to the craft, yeah?

• 45:26Speaker 00

  Well, look, you know, here's, here's what I'll say about that. I mean, I think that there are some phenomenal organizations that I think have the potential to really thrive. I think the big consulting firms, so take, I'll take two specifically that I'm relatively close to, Ernst & Young, and then Deloitte as an example.

• 45:44Jason Calacanis?

  Yeah.

• 45:44Speaker 00

  I think that these guys can thrive in the world of AI. Then you look at companies like, you know, PWC or Accenture, and it's like, it's like very critical to me, but it's like they picked a model provider. And it's like, how can you pick one of Anthropic and OpenAI? Not because they're not good, these models are incredible, but two reasons. One is, you're then tying yourself to only one technological roadmap, and you, you see the leapfrogging that's happening.

• 46:10Jason Calacanis?

  You have no optionality. Yeah.

• 46:12Speaker 00

  And then two is, I think Anthropic and OpenAI have realized what we've realized, which is the, the end boss of tokens. So if you want to generate ROI, you must be able to sell ROI, meaning return on investment, on token spend, to corporate Fortune 2000, Fortune 5000 CEOs.

• 46:36Speaker 00

  CEOs who can see a line of sight to making more money than they're spending. The thing that we all can see is that they are the most important customer. Why do you think Anthropic and OpenAI have started consulting JVs?

• 46:52Jason Calacanis?

  Yeah.

• 46:53Speaker 00

  So, you know, for Earth and Young and Deloitte, what I've told them is like, wow, you guys have made the best decision. Now, obviously, I'm biased because they picked us, but when you have a control plane, you can now be model agnostic, you can solve your clients' problems, you can actually work together. We work together really closely with them, they're incredible partners. It's incredible because now we get the benefit of decades of relationships, right? And trust that they've built and independence and auditability. And now we can work together to actually like solve people's problems.

• 47:23Jason Calacanis?

  Yeah, it's great.

• 47:24Speaker 00

  So, step one for like the next few years, we're going to be doing a lot of this, which is selling these big transformations into large corporate enterprises and then doing the methodical work of implementing it and making it successful. I think if we can do that, Jason, in three or four years from now, we move into phase two, which is how do you take software factory and then slowly submerge it under the water line? And that's the setup for phase three, which is how then do you have this just little, you know, maybe it's a voice pedal called Cofounder that exists. But what will Cofounder sit on top of? Cofounder will sit on top of an extremely robust software factory, right?

• 48:08Speaker 00

  Ultimately, and the understanding of how to get work done and how do you tie it to actual GDP and outcomes?

• 48:15Jason Calacanis?

  And if you think about it in terms of infrastructure, we turn a faucet on, water comes out. We don't even see all of that underpinning and we take it for granted, right? And we're kind of moving towards that with the solutions you're building and intelligence as a service in just in general. But there's a lot of things that happen before that water comes out of your spigot. And what we saw with Uber and some other folks were you give people unlimited water, they're just going to let it run and they're just going to be like a golf course. It'd be like making almonds and.

• 48:49Speaker 00

  In the bathtub because there's a valve where the water just runs out.

• 48:52Jason Calacanis?

  Yeah, let it run. Who cares? Like I forgot I put the bath on and this is what happened with token maxing, I think. And also it's got like slot machine type.

• 49:02Jason Calacanis?

  Addiction to it, which is you give it a job, it comes back, oh, the job's almost correct. And you're like, oh, I almost hit my flush. You know, if you're playing cards, let me see another flop. Let me see another flop. Give me two flops. And you get this like incredible rush, but more often than not, it's 60 or 70% of the way there. So you got to pull the slot machine again, which means you got to put another $100 bill in for tokens, right? It's pretty, pretty funny. Big announcement today. You've done your, is it the series A? And the other one's considered seed or series B?

• 49:33Speaker 00

  Series A. I mean, you technically are the seed, although we're calling you the preferred A1.

• 49:39Jason Calacanis?

  Okay, I'll take it.

• 49:40Speaker 00

  But yeah, you're the, you guys, so yeah, we raised $20 million when we started two years ago, literally almost two years ago to the day.

• 49:49Jason Calacanis?

  Yeah.

• 49:49Speaker 00

  Um, and it was great. It was, you know, all the besties, you and

• 49:53Jason Calacanis?

  Fun.

• 49:54Speaker 00

  Uh, Freeberg and Sax, uh, and then some incredible angels. Um, Nikesh Arora is the CEO of, chairman and CEO of Palo Alto Networks, Adam D'Angelo, who I worked with, he was a CTO at Meta and founder of Quora on the board of OpenAI.

• 50:08Jason Calacanis?

  He is podcast shy. I tried to get him on this podcast for a decade. It's, he's just so podcast shy. He just loves his work. What's Andrew like?

• 50:14Speaker 00

  He's great.

• 50:15Jason Calacanis?

  He seems very smart, very thoughtful.

• 50:16Speaker 00

  And then, you know, like a bunch of our friends from the, from the group chat, like Andrew Bogut, David Lee.

• 50:21Jason Calacanis?

  Love it.

• 50:21Speaker 00

  Sky Dayton, Diego Bertic, and it was, so it's, it's wonderful.

• 50:25Jason Calacanis?

  Isn't it nice to pass the hat with your friends for that first round? It's just, it's a really great feeling. And we've seen it now with, um, uh, our friend Sunny Madra passed the hat twice, uh, for us. We had, you know, two nice outcomes there. It's just a nice feeling if you can, uh, get there with your friends.

• 50:41Speaker 00

  So we raised, we raised 20 million in the seed two years ago. And then, um, yeah, I'm very excited. Uh, we, uh, raised, um, about a hundred, uh, in the A, um, uh, which is great. And we had an incredible lead, um, Mark Benioff and Salesforce Ventures.

• 51:03Jason Calacanis?

  Amazing.

• 51:03Speaker 00

  And then we had an incredible new group of folks also join, um, uh, Thomas LaFonte co two.

• 51:13Speaker 00

  Yuri Milner, Xander Lurie.

• 51:15Jason Calacanis?

  Oh, wow.

• 51:16Speaker 00

  Just great people.

• 51:17Jason Calacanis?

  Great humans. Now, this is the largest you've raised for a startup, obviously. What's it like? What are you learning as a CEO versus a capital allocator? Because I went to see the office and sometimes I call you like, hey, let's get lunch. Or can you come to this event or do something? You're like, I have a sales call, which by the way, I will.

• 51:38Speaker 00

  I tell everybody that's I do. It's I sell the enterprise software now. That's what I do.

• 51:41Jason Calacanis?

  You're an entrepreneur, doing the founder-led sales.

• 51:45Speaker 00

  No.

• 51:45Jason Calacanis?

  Which is always the best way to do it because then there's nothing between you and the truth. And you can then have this clarity of vision. That's why founder-led sales for the first couple of years is so important. Cause your sales team will massage you, massage the client. The truth gets kind of obscured 20% on either side. And now you're living in a house of mirrors. Like your sales team's making you feel 12 feet tall. They're doing the same thing to the client and like, reality is just distorted. But, but talk a little bit about what you're learning being a CEO versus a capital allocator? Or, or, you know, being somebody's top lieutenant.

• 52:21Speaker 00

  I think it's the same job. I mean, the difference between being an investor is I was only investing one of those five units. But being a founder CEO, you are allocating all five of those units. Now, you know, I, we benefit, I benefit definitely from having, you know, distribution that most founders don't start with. Right? You know, large Twitter following, obviously being able to do the podcast with you. That definitely has helped me and it's given me an advantage.

• 52:51Jason Calacanis?

  It gets you to, what I tell people is it gets you the meeting. It doesn't close the deal, right?

• 52:57Speaker 00

  Doesn't close the deal.

• 52:57Jason Calacanis?

  It will get you the meeting. People ask you for a selfie in the lobby. But you're not closing the LP unless your returns are there. You're not closing the client unless the value is there. So you can't overestimate it. Yeah.

• 53:09Speaker 00

  You know, where do I spend my time now? It's like, you know, it's, it's this, it's this constant state of worry, to be honest. Like it's.

• 53:17Jason Calacanis?

  Existential dread.

• 53:18Speaker 00

  I don't want to let my friends down. I don't want to let my investors down. I don't want to let my employees down.

• 53:27Speaker 00

  In terms of the actual, you know, so that creates this kind of like omnipresent anxiety that I think I'm actually pretty good at absorbing, like, you know, in many ways, Jason, like, I grew up in a pretty complicated household. I've been pretty open about that.

• 53:43Jason Calacanis?

  Sure.

• 53:44Speaker 00

  That was incredible training for this moment specifically. You know, my dad was an alcoholic. My dad, you know, didn't really think twice at times just to, you know, beat the shit out of me. Which it was what it was. Like, I don't, I have no grudge. But it's really made me able to absorb chaos, I guess.

• 54:05Jason Calacanis?

  I mean, if you look at all the great founders, you're going to find this like dysfunctional childhood on the margins or at the core of it. And, uh, you know, it's the pressure that makes the diamond, right? And then you get into a business situation and you're like, this is nothing compared to getting the shit beat out of me or living in terror or, you know, whatever it is.

• 54:24Speaker 00

  I just want to do right by the people that have taken, that put their faith in me. And so where do I spend my time maybe? So, you know, I spend a bunch of time, obviously, kind of like in the machinery of getting more business, because I think that that's very crucial. I spend a bunch of my time as a product manager of our network effects business. So, you know, there's, uh, the principal engineer and I, he sits side by side and, uh, you know, we're like, uh, little buddies pairing on this thing. Um, I spend a bunch of time there. And I've been spending a lot of time right now in the organizational design of 80/90. So, meaning, we don't have an org chart and we don't have a hierarchy.

• 55:09Speaker 00

  And so you may say, well, how does a company, you know, and look, we, like last year, we did seventeen and a half million of bookings. This year, if we execute, maybe we get, you know, we should have a decent chance getting to a hundred. Next year, I've already told them what the plan is, which is 500. I have no idea whether they're going to get there or not. But my point is, I wanted to take all the, all the drama off the table. And we're making a lot of progress, but the default, Jason, was to create an org chart. People would ask to hire people, then it's like, who should report to whom?

• 55:43Jason Calacanis?

  Yeah, then you get Game of Thrones starting, Fifthams. It's not the way to succeed.

• 55:47Speaker 00

  This is not how it should work in a world of AI. And so instead, I came with a framework. And, you know, I call it system on a chip. And so what does that mean? When you look at the iPhone, the iPhone's an incredibly beautiful product. It clearly works. It's incredibly successful.

• 56:04Jason Calacanis?

  I would, some would say the most successful product of all time in terms of profits and distribution. Yeah.

• 56:09Speaker 00

  Let's take two examples inside the iPhone. Let's take the camera chip and the power mammer, power management chip. What's so interesting to me is if you break open the iPhone, what you see is a circuit board. And what you see are a bunch of chips with a bunch of interconnects. So in the case of power management and the camera, the camera has no idea what the power management function does, except that it gets a signal. That signal is very specific. You know exactly what it is and it can act on it. And I tried to take that analogy and I said, you know, why aren't we organized like a circuit board? Why aren't we a set of chips and a set of interconnects? And what that does is it reduces each function into understanding what are the inputs and outputs of that function? I'll give you one example.

• 56:55Speaker 00

  So I went to marketing and I said, okay, don't ask me who reports to who, none of this stuff. You have two inputs. One is money. And the second is all the content that you may need. And the only output that you can generate are leads. Now those leads can be enterprise leads. They could be leads for people who want to buy subscriptions to Software Factory. The leads could be job applicants. But your chip takes in these two inputs, generates one output. Now draw your internals for me and let's go debate the internals.

• 57:26Jason Calacanis?

  That's where you start to get into tactics and strategies and how the and loops, yes. Processes.

• 57:33Speaker 00

  And so, and so what you start to see are like people designing cores, right? To use chip architecture language, cores and chiplets. And we debate the interconnects. And then, you know, the leads now feed into sales. Right? And then I go to sales and I'm like, all right, let's design your chip.

• 57:49Jason Calacanis?

  Hmm.

• 57:50Speaker 00

  Uh, and then I go to finance. You know, they, they get leads and they get, you know.

• 57:55Jason Calacanis?

  And a, and a customer client comes out the end. Yeah.

• 57:57Speaker 00

  No, they get just TCV is only allowed to come out the end. That's, that's all they're allowed to exude. T uh, uh, uh, to, to, their exhaust is TCV. And so then TCV goes into the 80, 90 enterprise team to then build the stuff. It goes into finance to account. And so my point is we've been playing this game essentially of reimagining the company as a circuit board and reimagining everything as a chip. And, you know, the chip is comprised of these cores and chiplets and everything has interconnects. And now you get to like a place, Jason, in a world of AI where agents can sit at these boundaries, measure everything. And I'm not saying that we've eliminated politics at all, but I'm saying it could be a path to it.

• 58:39Speaker 00

  So I've spent a lot of time trying to structure the, the mechanism of our company so that we can scale without the typical failure modes.

• 58:48Jason Calacanis?

  It's the, I mean, I think your customers are also going to go through this kind of change. We're seeing it when we debate, oh, these job losses, these layoffs, is it AI window dressing? Or is it actual reality? And then we debate it in a very granular way. It's obviously both, which makes the debate great. But the interesting thing about this moment in time, those middle managers who are responsible for massaging this chip and getting things in and out. And then what happens between the chips, there were humans there and those humans would bring their biases.

• 59:20Speaker 00

  This is a great example. This is a great example. So, so let's just say that marketing generates leads.

• 59:26Jason Calacanis?

  Yeah.

• 59:26Speaker 00

  Well, what happens at scale is they'll generate a lead and sales will say the lead sucks.

• 59:31Jason Calacanis?

  Yeah, the lead is weak.

• 59:32Speaker 00

  And instead, and instead, what should happen is at the boundary of those chips, there should be a DSP, right? Something that qualifies a signal as high or low or it scores it on a spectrum. And now we know what the leads are. We know how they convert. And to your point, there's nobody debating and arguing. It's not about personalities and emotions. It's about what does the numbers say?

• 59:53Jason Calacanis?

  A much simpler process and you know, it's, um, it's so great to hear you doing this because I'm also learning, learning with you and. Did a similar process where I took all the applications we have and we started scoring the applications for year zero, year one startups. And then we just have this great Socratic debate, the humans are in the loop. Hey, what should we weight the scores? And somebody had put into the weighting that the founders were coachable. And I was like, wait a second, how did that get in here? And they're like, well, you know, like we have these problems with these people who are hard to deal with as founders. And then we have these ones who are coachable. By the way, all of our money is made with the uncoachable ones.

• 1:00:31Speaker 00

  Yeah.

• 1:00:32Jason Calacanis?

  So you just put into the system, something that takes the diamonds and throws them in the refuse pile because they're a little sharp.

• 1:00:42Speaker 00

  Right.

• 1:00:43Jason Calacanis?

  They're supposed to be sharp. They're fucking diamonds, folks. Go back into the garbage and find me the diamonds you threw away. I want the uncoachable, difficult people. Those are the ones we make the money off of. It is one of the great aspects of systems thinking. And I kind of feel like the future is people who can think in systems, whether it's first principles, second order effects, and just understand the, I guess some people call it the IDMA's in business thinking, but the more you can understand the entire playing field, each of the chips, the more you can make that incredible brand product, right?

• 1:01:15Speaker 00

  I want to, I want to give credit to two people.

• 1:01:17Jason Calacanis?

  Yeah.

• 1:01:18Speaker 00

  This system on a chip org model for me was the output of reading Jack Dorsey's memo. And to be honest, I couldn't understand it and I thought I was dumb. And I was like, you know, Jack was talking about building a world model and a sales model. And I really couldn't get to the level of detail to understand what he meant and what he was doing. And so I was just kind of churning in my head, churning in my head, churning in my head. And I had a important meeting internally where I was talking to my co-founder, Sina, and it kind of out popped this idea. It's like, Sina, I just want a bunch of socks. I want to just be able to see I/O. And then I want to debate the pinout and the interconnects. And then he and I kind of sketched it together.

• 1:01:59Speaker 00

  And the second was Elon. I don't know if you remember, Jason, when Elon opened Tesla's first Giga factory, when we went to that party.

• 1:02:07Jason Calacanis?

  Nevada, we went there, yeah.

• 1:02:08Speaker 00

  Nevada.

• 1:02:08Jason Calacanis?

  Yeah.

• 1:02:09Speaker 00

  He showed me the layout of the factory and I said, oh, what is this? Is this a chip? And he was like, no, dummy. This is the machine that makes the machine. This is the factory. And that has stuck with me to this day. And the reason is because to your point about abstracting one level up, it's not about making the machine. It's about designing the system that then enables the machine to be made. So, you know, when I'm sitting there designing the org, I'm trying to think through like, what is the repeatable system that makes it like an iPhone and less like a brittle org chart, right? Or when we're designing software factory, what is the network effect that allows this thing to just spin faster and faster every single piece of software

• 1:02:51Speaker 00

  that we see? And I think if we get these things right, we have the chance to build something quite interesting.

• 1:02:57Jason Calacanis?

  Yeah. And it's, it's great. You're in the arena, trying things, running a company.

• 1:03:02Speaker 00

  All of those things.

• 1:03:02Jason Calacanis?

  All of those things.

• 1:03:03Speaker 00

  The heaters are gonna be so mad, Jason.

• 1:03:05Jason Calacanis?

  I mean, you're gonna pull it off too. And they're gonna be like, oh, he can actually build a company too, in addition to a podcast. I took a couple of pictures when I was there. Uh, cause I got to visit. Yeah, yeah. Here's the first picture. This is you, uh, working in the factory.

• 1:03:22Jason Calacanis?

  Oh, no, this is you on the sales. There's Chamath. And there you are. Look at that.

• 1:03:27Speaker 00

  Wow, you did arm day.

• 1:03:27Jason Calacanis?

  In the factory, yes. Getting dirty, getting, rolling up your sleeves, getting dirty, sweating. So you really can do both. You can do both. We have photographic evidence. You're able to hit the road in that. Let me see that suit again you're wearing. Oof. This is the J.C. Penney suit. Yeah. Rugged. Look at that with the blue.

• 1:03:45Speaker 00

  Burn that suit.

• 1:03:46Jason Calacanis?

  I mean, listen, you gotta go knock on some doors. Uh, you know, the young folks love to hear from you. Uh, love to hear from, oh, there. And there you are in the, uh, drink with me. And that one looks actually, the way these Chinese, these are Chinese models, by the way, that we've been playing with internally. Oh, there, you didn't like that one. Oh. That one, that that's a that bottle one, Ben. This is what the idiots who work for me and I do. We're like producing a podcast and they just make images to try to get me to break up on hair. So they're showing me these as we don't we're we're image maxing. We're image maxing. We're meme maxing. It's it's pretty funny, but um, let's um, look back um, and young people coming out of school now.

• 1:04:28Jason Calacanis?

  Whether they've, let's put aside like how in debt they are. We all agree you shouldn't go in debt. It's kind of a settled issue. We understand the future is AI. So for our kids, we have kids of similar ages. We have teenagers and and some younger kids. You know, over the next decade or two, they're going to be going through college. They're going to be into the workforce. What are you raising them? How are you raising them in terms of skills, hard skills, soft skills? Whatever in between, but how are you thinking about getting them ready to take on the world? And be productive in it. And then which revised to people who are in college. You got a lot of your Waterloo alumni. What are you thinking now? And just dream of consciousness, because this is a dynamic field here.

• 1:05:11Speaker 00

  I don't have a good answer. I I have not tried to answer this for my kids because I feel like I I ask this question more than I answer it. Um, and I don't really know. And the only thing that I've concluded is that I think it's very important for my kids to have their own adventure. I want them to, you know, do something interesting and have some wins, have some losses.

• 1:05:38Speaker 00

  But beyond that, I don't really have much of a, I don't, I don't have a plan. Um, I just hope that they find an adventure. And if I can be a part of helping them find that, that I think is going to be the whole challenge. Cause like, and why do I say adventure? Cause I think it's kind of like all encapsulating. Like if you think that the food, the shelter, you know, your basic necessities are essentially covered for you in a in this next iteration where most things are abundant.

• 1:06:04Jason Calacanis?

  Yeah, modern society, uh, a society.

• 1:06:07Speaker 00

  Society evolves.

• 1:06:08Jason Calacanis?

  Abundance, yeah.

• 1:06:09Speaker 00

  It's still not going to change. Millions of years of hardwired physiology. So how your brain has evolved, that's not going to change in one generation.

• 1:06:19Jason Calacanis?

  No.

• 1:06:20Speaker 00

  And so I think if you, if you understand that, you know, the human's desire for agency and for risk.

• 1:06:27Jason Calacanis?

  Problem solving, socialization, there's some core things that are just inherent in who we are. We're going to want to play games, we're going to solve problems, we're going to want to socialize. And if you don't do those things, by the way, you're going to all of a sudden have people telling you, you've got to put your kids on SSRIs or speed to get them to have those things. And it's like.

• 1:06:45Speaker 00

  Yeah, the best, that's why, that's why I think the best word that I have come up with is adventure.

• 1:06:50Jason Calacanis?

  Hmm, I like it.

• 1:06:52Speaker 00

  And I would like my kids to have a chance to have an adventure. I mean, I've had a, I've had a great adventure, you know, and it's still, it's still only half done.

• 1:07:02Jason Calacanis?

  Yeah.

• 1:07:02Speaker 00

  And, you know, you've had a great adventure, like, it's like, this is what you want for your kids.

• 1:07:05Jason Calacanis?

  Kid from Tor- I mean, you were Toronto originally?

• 1:07:08Speaker 00

  Ottawa.

• 1:07:08Jason Calacanis?

  Ottawa, kid from Ottawa, kid from Brooklyn and now look like, and we still have 20.

• 1:07:14Speaker 00

  Great.

• 1:07:14Jason Calacanis?

  30 great years, who knows if they're going to solve some life extension, God forbid, we'll be doing episode 2000 of All In somewhere. But yeah, I've been, I've been thinking about it a lot too. I don't have the easy answers, but the one I came up with is very similar to your adventure, which is exposure, exposing them to possibilities, exposing them to, you know, high agency people. And I think if you can expose them to these things, then it's enough because young people have that energy, they'll find something that will pull them to it. But I wish somebody had exposed me earlier to entrepreneurship, a little earlier to risk taking. I had to find that myself, right? You had to find it yourself eventually.

• 1:07:58Jason Calacanis?

  And that's like, I'm taking them to Tokyo with me for Founder University, and I'm going to let them sit in on it. And it's like, I just thought to myself, man, if I, if a 10 or 16 year old J Cal had experienced Tokyo, you know, my first, my first time on an airplane was when I was 15, 16 years old. I went to Florida, we didn't have the money for airline tickets, that was out of the question. Our vacation was, how far can we drive the van before it reasonably breaks down?

• 1:08:24Speaker 00

  Were you upset when your dad had only bought you a one-way ticket?

• 1:08:28Jason Calacanis?

  It was just like, good luck getting back, son. It's always great to catch up. Congratulations, 80, 90. I think I gotta talk to you about branding. You're getting very good at branding. I love the with me branding. Great on that job. On 80, 90 and Software Factory, both of them are interesting names. 80, 90, hey, 80% of the cost for 90 or 80% of the features for 90% less.

• 1:08:55Speaker 00

  90% less is how it started. I'm not sure if we'll deliver that, but that's.

• 1:08:58Jason Calacanis?

  Well, still great as an idea, but Software Factory is iconic. So I think we could retire 80, 90 at summer and just call it TSF. Like there's TFL, the French Laundry we went to. This is like TSF and people will start referring to it. Hey, did you talk to TSF? Hey, what did TSF say? Or have you tried TSF to solve that problem and just, you know, TSF or whatever? Cause when we were up at the French Laundry, which how great of an experience was two days at French Laundry?

• 1:09:32Speaker 00

  Yeah, that's amazing.

• 1:09:33Jason Calacanis?

  Give people a little sample of how crazy our lives are now. And just getting to go hang out with TK out there.

• 1:09:40Speaker 00

  I mean, I think, I think being around these kinds of people are very inspiring for me. It's like, you know, you can be as successful as you want, but then there's just a lot of people that stop. And then there's a certain core group of maniacs that never stop. And I admire that, you know, Buffett, Thomas Keller. These guys could have stopped a long time ago. They keep going and I just find it deeply impressive.

• 1:10:06Jason Calacanis?

  And the intentionality.

• 1:10:07Speaker 00

  Why is that? I think, I think it's because they're playing their own internal game. They, you know, the, the problem with like defining your life in terms of external measure is at some point you'll hit it.

• 1:10:17Jason Calacanis?

  Yep, then what?

• 1:10:18Speaker 00

  And then, and then you'll think, oh, I guess that's it. And then you kind of stop. And instead, I think you have to be deeply selfish about this, which is you got one trip around the sun, just never stop.

• 1:10:28Jason Calacanis?

  Yeah, just keep, why not keep?

• 1:10:30Speaker 00

  All the things you want to do, just never stop.

• 1:10:32Jason Calacanis?

  Yeah, be relentless. That's another thing for these kids. I'm, I'm big on the role, the. You know how some things take like four days or five days to get good at? Some take, you know, five hours. So if you look at skiing, right? Like, gosh, when you started skiing, man, it was like watching Big Bird coming down the hill blindfolded. And now you're like, whoa, cut an S-turns. You could do a diamond, but you stay on the blues. Like you, you could ski, you could ski. Five years later, you can actually ski. Ish, you're like the Sri Lankan skier. It's like unbelievable. You could be on the Sri Lankan Olympic team. I don't know if there's any others.

• 1:11:09Speaker 00

  The only person more awkward than me is Free Bird, which gives me some solace.

• 1:11:13Jason Calacanis?

  I mean, Free Bird coming diamond. Every time he comes down, it's a knee injury. He's, I'm like, are you coming out tomorrow? He's like, no, my knee, my hip, my this, my that, poor guy. He's not built for it. But what I did with my daughter, my 16-year-old specifically, was I was like, what are things we can do together, daddy-daughter date? That take like that third or fourth time to have the unlock where you go, ooh, I like this. So pickleball, skiing, anything like that that takes like three or four times to get good at? It just builds that resiliency. And once they've done the third or fourth one, they're like, what's next? What's next? What skill can I learn that's kind of hard? There's your hour plus with my bestie, Jamal.

• 1:11:51Speaker 00

  Poly Hoppy. Love you, bro. I really appreciate you, Jason.

• 1:11:53Jason Calacanis?

  I appreciate you too, bro. Yeah. Oh, thanks for coming back on the show as one of the Twist All-Stars for summer of 2026. Nine more to go, folks. It's going to be a great summer. Keep tuned in to the podcast feed. Bye-bye.