In short
The episode discusses an OpenAI “agent” breach of Australia’s Medicare statistics portal, arguing about whether it’s a meaningful security failure or mostly a terms-of-service/controls issue. It also covers Google’s plan to test AI compute in space via TPUs, and then shifts to product/market talk with guests about AI tools for CRM and AI-driven marketing websites.
Guests (and backgrounds)
- Heath Paris, founder of Lightfield (AI-native CRM). Background not detailed in transcript; described as building an AI CRM that updates from email/calendar/Slack/notes.
- Brian Chow, founder and CEO of Ploy (AI marketing platform; in YC current batch). Co-founded Webflow; led engineering there ~12 years. Previously founded Vungle (and Webflow is described as a no-code web design tool).
Key claims
- Australia says an OpenAI agent accessed the Medicare Statistics Reporting Service portal (June 18), discovered Aug 11, disclosed Sept 10; no private personal data taken; OpenAI says it was an internal evaluation to gather statistics.
- Hosts argue agentic systems will repeatedly “route around” blockers unless humans enforce stronger controls and ToS compliance.
- Google’s “Project Suncatcher” will test space-based ML compute; cooling and failure points are a concern.
- Ploy’s thesis: start from the website as the brand/data nexus; agents should drive outcomes (leads/customers), not just generate ads.
Notable examples
- The hosts cite “routing around” blockers (e.g., creating accounts via a computer-embedded workflow) and suggest testing across models/services.
- Ploy example: “Deploy Site Slurper” migrates an existing site; Ploy creates a brand-locked design system for ads and landing pages to avoid “slop.”
- Lightfield example: set up in ~10 minutes by connecting email/calendar and other sources; it builds a “temporal context graph” for CRM memory.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOPersonal Health Insights
0:18 to 0:32
Hosts share personal health experiences and tech used for monitoring.
“PaperOS offers the largest library of AI-driven workflows for both founders and fund managers.”
Personal Health Insights
0:42 to 1:46
Hosts share personal health experiences and tech used for monitoring.
“You know, I woke up, Lon Harris, and my whoop was fire alarms going off.”
Plod: The New Show Note Tool
1:46 to 4:19
Discussion on how Plod simplifies the process of creating show notes.
“I say all this because we are living in a golden age when if you have this technology and you have AI, it's starting to figure things out in an amazing way ahead of time.”
OpenAI Breach Discussion
4:19 to 4:36
Hosts discuss the implications of OpenAI agents breaching Australia's Medicare system.
“And if you use the code twist, they're going to give you 10 % off on your purchase of your, your note pin or your note pin S.”
AI's Challenges in Compliance
4:36 to 7:28
Analysis of the challenges OpenAI faces with compliance and ethical concerns.
“We got to start with another OpenAI breach once more into the breach.”
Investigating the AI Incident
7:28 to 13:16
Continued exploration of the Australian incident and its implications.
“Go say, I want to make myself as a Jedi.”
Google's Space Compute Plans
13:16 to 14:00
Discussion on Google's Project Suncatcher and future of data centers in space.
“If you're a politician being concerned about AI right now is just a smart thing to do because it's - Yeah, you're in the mix.”
The Future of Space-Based Computing
14:00 to 16:28
Discussion on the potential for space data centers and the involved companies.
“So, I mean, I guess the question that always comes up when we talk about this is, is doing our compute in space data centers in space?”
Leveraging Athena for Executive Assistance
16:28 to 17:59
Jason shares insights on using Athena assistants and AI to enhance productivity.
“Well, you know, it's Athena is a full time assistant for you from the Philippines, who's in the top 0.1 % of the knowledge workers there for but$3 ,000 a month.”
Leveraging Athena for Executive Assistance
18:02 to 18:28
Jason shares insights on using Athena assistants and AI to enhance productivity.
“You can get$2 ,000 off your first executive assistant, athenawow.com slash jcal or athenawow.”
Show all 37 chapters
Introducing Brian Chow and Ploy
18:56 to 21:48
Introduction of Ploy's CEO Brian Chow and his background in AI marketing.
“It's a hard one that rolls off the tongue, but yes, you got it.”
The Evolution of No-Code Tools
21:48 to 24:25
Brian discusses the transition from no-code to vibe coding in startups.
“So, you know, we're building this super powerful AI website platform.”
Ploy's Unique Position in a Crowded Market
24:57 to 28:00
Brian explains Ploy's strategy to stand out in the competitive AI website building market.
“Where a world where agents and just the model capabilities can do so much.”
The Challenge of Effective Advertising
28:00 to 30:21
Learn how Ploy differentiates itself in creating personalized AI ads.
“So for example, like if you are, I don't know, a big, you know, AI company, base 10, together AI, like you really, really care about how your brand motifs of these shapes and colors are showing up.”
The Impact of Agentic Commerce
31:18 to 35:38
Explore how the rise of agent-driven commerce affects businesses and the web.
“what are your thoughts on how that's all going to change now?”
Fundraising Strategies for Entrepreneurs
35:39 to 40:36
Understand the tactical approaches to fundraising in a volatile market.
“How do you think about fundraising as a serial entrepreneur who's had success, made a little bit of money yourself?”
Navigating VC Conflicts of Interest
40:37 to 42:01
Discuss the complexities of VCs investing in competing companies and their implications.
“So, and how do you know in the seed series a space, which one's going to be the 80 % market share Uber or Airbnb?”
Cautionary Tales for Founders
42:01 to 44:32
Learn about the importance of focusing on your own business rather than competitors.
“And when they told another person who was a bigger investor than me, Masayoshi-san just said to him, no, DoorDash, not competitive.”
The Importance of Self-Perception
44:33 to 46:08
Discover how our perceptions of ourselves are often exaggerated and largely forgotten by others.
“Now, I remember when 100 people are looking at you like, oh, my God, are you a klutz?”
Building AI Partnerships vs. Independence
46:09 to 47:36
Explore the pros and cons of partnering with AI models versus developing your own.
“So Sam came, offered that in the spring, every YC company, this deal for like one and a half million credits and uncapped note, no MFN.”
Understanding Exchange-Traded Funds
47:37 to 49:56
Gain insights into how exchange-traded funds work and their benefits for startup founders.
“I think we have a good portion of my batch took it.”
Innovative AI Solutions with Ploy
49:57 to 53:06
Learn about Ploy's unique approach to AI-driven website and customer growth solutions.
“And in return, you get essentially exposure to an index of other tech stocks that other people have pledged or committed to the funds.”
Bay Area Real Estate Insights
53:07 to 53:38
Hear thoughts on the current state of Bay Area real estate and its market evolution.
“Now they're like, you're going to make a fortune on this thing.”
Upcoming Tech News and Trends
53:39 to 54:03
Preview upcoming tech stories and trends discussed in the episode.
“We've got a ton more news if you want to do more news.”
The Importance of Data Access in Organizations
56:00 to 58:05
Learn how data access affects decision-making in organizations.
“There's channels, there's hidden, there's private channels.”
Trends in Enterprise AI Agents
58:05 to 1:01:21
Discover the current landscape of enterprise AI agents and their future.
“Like there's one of the most crowded spaces that we talk about on This Week in AI at this point is like enterprise agents that help your team organize.”
Tesla's Optimus Robots: Production and Market Outlook
1:01:21 to 1:05:01
Explore Tesla's production plans for Optimus robots and their potential market impact.
“This morning, the information reported Tesla now builds several hundred Optimus robots a week, roughly 10x their Q2 pace.”
The Future of Basic Skills in Education
1:05:01 to 1:08:02
Discuss the relevance of basic skills like math in a technology-driven world.
“He said it doesn't matter if kids can't do basic math anymore because maybe those skills don't matter as much in the future.”
Mental Health and Physical Well-Being
1:08:02 to 1:10:00
Understand the connection between physical activity, diet, and mental health.
“But I mentioned this study, I think, on All In.”
Strategies for Improving Mental Well-being
1:10:00 to 1:11:10
Learn practical strategies to boost your mental health and social interactions.
“I say, if I'm feeling out of sorts, how did I sleep last night?”
The Impact of Social Connections
1:11:10 to 1:12:28
Understand how social interactions and pets can improve mental health.
“You get a new dog, you have no choice but to do two walks a day and somebody's going to come over and be like, oh my God, your dog's so cute.”
Nike's Branding Challenges and Opportunities
1:12:28 to 1:14:34
Explore Nike's marketing strategies and potential celebrity endorsements.
“about what does her body mean and what side of the political war is she on?”
Cultural Commentary on Marketing and Celebrity
1:14:34 to 1:16:54
Discuss the role of controversial figures in marketing and public perception.
“And then if you just put a star in there for the you and like, yeah, just do it.”
Debating the Sexualization of Female Athletes
1:16:54 to 1:19:44
Examine the implications of sexualization in sports advertising and public reactions.
“This is the ancient Greek adjective meaning naked, nude, unclothed.”
Anticipation for Tarantino's New Project
1:19:44 to 1:21:41
Get insights into Quentin Tarantino's latest film and its connections to previous works.
“Serena Williams, Venus Williams, Dwight Howard, Chris Paul, Carl Anthony Towns, everybody has done this ESPN thing.”
Reflections on Classic Cars and Personal History
1:21:41 to 1:24:00
Hear nostalgic stories related to classic cars and their significance in the past.
“And, you know, Brad Pitt and David Fincher, what a duo.”
Nostalgia for a 1970 Mustang
1:24:00 to 1:25:46
A personal story about owning and experiencing a 1970 Mustang.
“If you look at that 1970s Mustang Grande, 1970s Mustang Grande, I bought it for$600.”
Transcript
Automatic transcript. May contain errors.0:00Lon Harris:All right, everybody, welcome back to Twist for Friday, September 25th, 2026. This Week in Startups is brought to you by the Conservation Fund. For 40 years, the Conservation Fund has protected at-risk land and important wildlife habitats while actively supporting local communities. Learn more at conservationfund.org. Building an empire? PaperOS offers the largest library of AI-driven workflows for both founders and fund managers. Whether you're raising capital, launching a fund, or wading through diligence, PaperOS unlocks simplicity and scale for your ever-growing empire. Claim your$10 ,000 credit at paperos.com slash twist.
0:32Lightfield, name one person who's ever enjoyed updating a CRM. Exactly. Lightfield's AI agent does it for you. It even prospects and books your meetings. Used by thousands of startups. Free at lightfield.app.
0:42Lon Harris:You know, I woke up, Lon Harris, and my whoop was fire alarms going off. Fire alarms. My respiratory rate, my skin temperature, everything. It's like you're dying. If you have any kind of a problem, given these metrics, and it gets worse, go to the emergency room. There's a first. Wow. Yeah. Well, I, you know, I had a steak last night and it was dry aged, like a very significant dry aged steak. Delicious. And, you know, it had a little funk on it. Like when you dry age it like that, you go. So I was wondering. They cut the top layer off. You see the butchers like they slice the top layer off. Correct.
1:20Lon Harris:I see now you're getting right there, Lon, man of many talents with great knowledge. Talked to the chef. He said, I like to leave a little of that on. I like to leave a little of that on for the flavor and the fact. I said, okay, fair enough. But my stomach was kind of doing backflips last night, and I asked it, hey, what's going on here? And it's like, yeah, that would be indicative of your body fighting a bacterial infection is your respiratory rate going up heat. I say all this because we are living in a golden age when if you have this technology and you have AI, it's starting to figure things out in an amazing way ahead of time.
2:01Lon Harris:And, yeah, you're on that journey with Roe.co slash twist, losing a little weight. I'm doing that. We've got all these gadgets, the Whoop, the Aura, everything is out there. You've got function health. You've got superpower. You've got all these incredible things. You know what's incredible for me? Plod. I get this Plod pin. I love it. I just press the button. Boom. Everybody knows that it's recording because, hey, it's got a light. And this company keeps releasing new features. It was so good. We used to write show notes, right? Yes. It would take a couple of hours. It would take a long time to write show.
2:34You like to go through and be very detailed. So it's trying to collect. Here's all the references we made. Here's all the links to all the articles we talk about. Here's all the suites that we reference. It's a lot of information by the time you're done. Right. And so I said, well, wait a second. Put this human version up against the Plod version.
2:52Lon Harris:So we'll show it on the screen here. You can do multiple tabs. You can do a mind map. You can do a transcript. You can do a summary. You can do lessons learned. And now we're starting to do three or four of these each time. And for you, our dear listeners, can go into our show notes, and you'll find the link to the Plod. and boom, here it is. Transcript summary, meeting highlights, teaching note. Yeah, that's a new one. I did the teaching note, which is if you were a teacher and you were making our podcast into a lesson for your students, this has a complete guide for how you would instruct people or how you could lead discussions based on what we talked about on the podcast.
3:34It does all this automatically.
3:35Lon Harris:Incredible. And one thing we still have to do is teach it who's speaker one. I'm assuming that's me and your speaker two, but it could be the opposite. It gets to know you. It syncs automatically. They've got this beautiful, let me show it because I have it right here, beautiful cradle like this. You pop it in there. When you pop it in there, it will actually connect over, I don't know if you set this up, it will connect over your Wi-Fi and sync if you forget to sync. So charging equals syncing. Pretty dope. Unlimited. Incredible. They have one that snaps on the back of your phone if you prefer that format.
4:06Lon Harris:But where do they go to get more information? maybe even a little bit of a spiff. Are we offering a discount or anything? We are. So you want to go check it out at plaud.ai slash twist. And if you use the code twist, they're going to give you 10 % off on your purchase of your, your note pin or your note pin S. What a deal. What a deal. And you know what? You don't even need the discount. You're all rich, but please use the discount codes because that lets people know, Hey, we sent you there. You heard about it from Jason and Lon. Exactly. We got a lot in the news. Where would you like to start?
4:39We do have a lot in the news. We got to start with another OpenAI breach once more into the breach. What are we doing here, folks? Australia's prime minister now says an OpenAI agent broke into the Australian Medicare Statistics Reporting Service portal on June 18th, PM. Anthony Albanese, there he is, said the agent found a way around the blocks and did not accept no for an answer. OpenAI discovered the breach on August 11th. They waited until September 10th to email a public disclosure inbox. That's 84 days from the time of the incident to their disclosure. Australia has launched a task force and researchers at the independent AI research lab Transluce found the agents probe several other government and university websites.
5:24Jason, they're everywhere, these open AI agents.
5:28Lon Harris:You know, you have to build software that is resilient and that has controls in it. And this is powerful software because it's agentic and it's been instructed to please you because it has the entire history of hacking, you know, in a bad way, in a good way, getting things done, GSD, blowing through various blockers, as we'd say, in business. You're going to have this happen over and over again. They want to please you. They've been instructed to solve your problems. and then they have this corpus, which is like, hey, by the way, if you can't get X done, here's the route around. Now, I know this because I was using Muse and it's like, yeah, I can't set up an X account.
6:10Lon Harris:I cannot set up a Gmail account for you. Because I was like, I want to create a dedicated email account for my Muse bot and for my Muse bot's Twitter. So I can kind of do things with the rest of the world, not mine, but this. And it was like, I can't do that. I was like, okay, here's what I want you to do. Let's do it through the computer that you have embedded here. And if you get any blockers, let me know. I was like, oh, of course, let's do that. Right. So here we go, folks. It's very easy to instruct these things to break the terms of service. And then when it was like, hey, oh, I can't check things out on Amazon, you can just re-instruct it.
6:43Lon Harris:Go do that. They're going to need to put more humans in the loop. They're going to need for it to understand what is against the terms of service and what is okay with the terms of service. And the problem with that is you have five different competitors. And once one says, you know what, I'm going to make you your Jedi image, I'm going to use a celebrity or IP in my image, the other four are left with being not competitive. Once one says, I'll check your stuff out on Amazon, even if I'm breaking the rules or bending them, then all four have to do it. So if you want to test this, use Claude, which has the most rails, I believe.
7:19Lon Harris:Pull up the sidebar, put it in like a New York Times article, which they're in a lawsuit with. And they're just like, no good. We're not summarizing this story. We're not reading the page. No bueno. Go to Disney. Go say, I want to make myself as a Jedi. See which services do it, which services don't. It's going to be a lot of lawsuits. Yeah. It seems like it's, I mean, obviously OpenAI, they're out here saying like, we don't have a plan. They call it alignment. You know, like we don't have a plan on alignment. We don't really, we haven't figured out human alignment. Like we're still in a place where like morals and ethics and people are debating that every day because there's a million different variations of every scenario.
7:55It's like every curb your enthusiasm. You can have an argument about, well, was Larry David right or was the person that he was feuding with right? Perfect analogy. Because there's a billion scenarios like that that you could imagine. So how are we going to predict and imagine every scenario an agent's ever going to face? We can't. I don't know.
8:13Lon Harris:Like sampling of ice cream, that famous scene where he's like, you get two samples. And she's like, well, that's not a rule. And she's on sample number seven, sample number eight. And it's like, well, we live in a society. You really can't, if there's 12 ice cream to eat, you can't go beyond four. Like, it's obvious what you're doing is you're going to do 12 and then leave. So keep it to two. But they should put a sign out, hey, we can do two samples. That's it. But you're right. It is something where you're going to have to look at the terms of service and say, what is the terms of service that this person has told us on how they want to deal with bots?
8:50Lon Harris:and I respect that terms of service. Yeah. And then it's up to you as a hacker to build tools that route around it. And now it's on you. So when I said, hey, route around it, I'll do it. I was essentially saying, you can do some activity here that I will click the yes button. I will break the terms of service and create a Gmail account through my Muse, which I'm certain is not allowed, is the automation of email accounts. But that's where user responsibility comes in. So here we are. just going to be adjudicated one at a time. But here, I mean, going into the portals and finding, you know, uh, they're Medicaid, invading the Australian Medicare system.
9:33Who sent it to do this is what I'm trying to find. I don't, that was not in my, in the story that I read. I don't know why it was there. Like, what was it doing initially? I'll take a look and see if I can find that.
9:44Lon Harris:Hey everybody. I'm here with Heath Paris. He is the founder of Lightfield. They are an AI native CRM and it builds and it updates itself in real time based on whatever's in your email, your calendar, your Slack, your meeting notes, you know, all the most important stuff that keeps getting lost. Great to be here. How long does it take to set up Lightfield? You have Slack, you got Notion, you got all these different data sources. I'm sure you can pull in people's help desk tickets and complaint line. Plus, everybody has tons of customer interactions on their email and their mobile phones. How do you set it up and make sense of all this different noise?
10:20So you could get set up in about 10 minutes. If you don't have an existing CRM, you sign up, start on self-serve, connect your mail-in calendar, connect all of your data sources, either through MCP or the REST API, and then Lightfield will structure all of that and make sense of it for you. We'll go and build a temporal context graph. We'll index things. We'll enrich everything. And so you'll have great, workable, pliable memory within minutes.
10:50Lon Harris:All right. Everybody go check out Lightfield.ac and see what it can do for your company. Don't lose any customers and find some new ones. Lightfield.ac. I'm guessing it was a scraper. So, you know, OpenAI scrapes, you know, the open web. And perhaps they have a terms of services. Hey, you can't scrape. But it went there and it's scraped anyway. Or there was some, you know. Okay. Okay. He's saying, so here's what the PM was saying. Australia is doing a forensic investigation right now. So they're trying to figure out more about what happened. But this is a public facing statistics portal that contains non-sensitive Medicare information relating to data and statistics.
11:30So it is likely exactly what you're saying. It was doing some kind of research. It was doing some kind of scraping. It was looking for this public data. And then it got it by breaching into their system.
11:41Lon Harris:And it says, you know, OpenAI didn't know it was going to do this. So now we're having a debate. And I think this one has to do with terms of services because they could always put this behind a paywall. They could put this behind a login screen. They could have you do know your customer. It's like five levels of authentication that could be done here to protect this. So this sounds to me like Australia wants, you know, to have a certain level of protection here, but they didn't put the blockers in place. and then opening eyes going, YOLO, get me every piece of information you can. And they probably have instructed it like, hey, if there's information and data to get out there, go get it.
12:17Lon Harris:And if you have to find three or four different ways to do it, you know, be resilient, try three or four different ways and probably check the box that says, I will not scrape this. And it went and scraped it. But this one is not a hack, right? This one's not a hack. They didn't take people's individual healthcare. No, it does not. It doesn't. So Australia is saying no private personal data has been sort of taken. OpenAI says that behavior occurred during an internal evaluation in which its system was trying to answer questions and gather statistics about Australia. It did not what I didn't didn't mean for it to go anywhere.
12:51It wasn't supposed to be is what they're saying.
12:53Lon Harris:OK, this sounds like a tempest in the teapot. This might be the prime minister of Australia wants to jump into the safety discussion. And now they have a window to jump into that. Right. So never discount an individual's desire to say, I got hacked too, and I want to get in on the discussion, and here we go. If you're a politician being concerned about AI right now is just a smart thing to do because it's - Yeah, you're in the mix. You're in the mix. Maybe you get some votes here, maybe you get some votes there. It's a popular topic. You get a little airtime. Okay, let's keep going. All right, let's keep going.
13:30Google launching four TPUs into orbit next week on SpaceX's Transporter 18 rideshare mission. This is the first flight test for Project Suncatcher. That, of course, is Google's plan to run machine learning compute in space. Google says satellites in low Earth orbit can collect up to eight times more solar power than they could on Earth. The long term design, a kilometer wide array of 81 satellite clusters. Two more prototypes are due in 2027. Kevin, Google stated goal here is finding the failure points and engineers are already arguing that their cooling math does not work. So, I mean, I guess the question that always comes up when we talk about this is, is doing our compute in space data centers in space?
14:13What is your timeline on when we're actually going to start being able to realize this goal? Jason, make a prediction.
14:20Lon Harris:There are already test flights occurring, throwing things up there. There's a dozen companies who are involved in this. I suspect this is not going to be something that only SpaceX does. So SpaceX is going to give carriage on their rockets to anybody who wants to put their TPUs in space, and they'll be competing with them at the same time, which is, I think, part of what's happening with Starlink. Starlink has customers who are also, or SpaceX has customers competing with Starlink, and they're smart enough to know we shouldn't limit people's ability to get to space. Let a thousand flowers boom.
14:55Lon Harris:You don't want to get into a antitrust situation where, you know, you're not letting other people put stuff up there. And people don't know this, but Google invested$900 million in SpaceX's$1 billion round January 20th, 2015, according to a large language model. And so they owned like something in the range of 6%. And this has been incredible for them. So they have a$94 billion position. I don't know if they've ever sold it, but this is 100x bet for Google. And so congratulations to Google there. And as we say in Silicon Valley, no conflict, no interest. Everybody's going to want to see if they're...
15:39StarCloud, I was going to say. They're also, they've got, they're putting their own data centers in space, but they also have a deal with Starlink to integrate their mini laser terminals across more than 25 orbital data center satellites. So there you go.
15:51Lon Harris:Yeah. So it's one of these situations, like I talked about with Jensen, where he's making open source models. He's making a stack for robo-taxis. He's also selling compute to Tesla. Tesla's also building their own gigafactory to, or I'm not sure what they call it, giga-something, gigafab. Yeah. So they're going to be making chips. TerraFab. So they're going to be making chips. Everybody's going to do everything. That's just the nature of this. And, you know, let a thousand flowers bloom is what happens in our industry. Let's keep going. Sure. Well, you want to talk a little bit about Athena and your EAs?
16:28Lon Harris:Well, you know, it's Athena is a full time assistant for you from the Philippines, who's in the top 0.1 % of the knowledge workers there for but$3 ,000 a month. The person is incredibly diligent. They work incredibly hard. They do the hiring. They do the firing. They do the training. And you have an assistant. Now you say, hey, wait a second. Aren't we having all these digital assistants? You know what I did? A year ago, I had them on OpenClaw. I had them using Claude. I had them using Chad GPT to do their work. And I'd say, here's how I would have booked a hotel or found hotels in Singapore, whatever.
17:04Lon Harris:And then just this last week, I said, OK, here's what I want my two Athena assistants who work seven days a week. And they do all kinds of human in the loop projects. I told them, create a GrokBot that the two of you share and create a Muse account. And now what I want you to do is to create bots. And then you do the final polishing step. Talked earlier, hey, you're trying to create a Gmail account. You're trying to put up a website. A human has to click OK at some point. So now I'm making the Athena assistants basically superhuman with these tools. And what I found is Americans, we have such low unemployment in this country, the idea of being a dedicated executive assistant is not something most Americans want to do.
17:46Lon Harris:But in other regions of the world, that is an incredible job to get paid two or three times as much as everybody else in your country. Amazing job with tremendous upside. So I'm super happy to have been the first investor in Athena. You can go to athenawow.com. It'll redirect you to my URL, and they'll give you a couple of weeks, right? What are they giving you? Yes. You can get$2 ,000 off your first executive assistant, athenawow.com slash jcal or athenawow. You can take your pick, whichever one you want. I like doing athenawow.com. I'm an investor and a user of this software. You know who else uses it?
18:21Lon Harris:Shamal and David Friedberg's team. So you've got three or four besties that are deeply involved. Three out of four besties agree. That's like nine out of ten dentists. Yeah, that's pretty great. All right, let's keep going. All right, well, we got a guest. We should bring our guest up. Up next, we've got Brian Chow. He's the founder and CEO of Ploy, Jason. They're an AI marketing platform. They're in Y Combinator's current batch. He also co-founded Webflow and ran the engineering team there for around 12 years. So this is actually his third company as a technical founder before Webflow founded Vungle.
18:55That's in my bundle. Am I saying that correctly, Brian? It's a hard one that rolls off the tongue, but yes, you got it. All right. I nailed it.
19:01Lon Harris:So thanks for joining us, Brian. Welcome to the show. Yeah. Nice to see you. And now remind me Webflow. That was like a Squarespace competitor, Wix competitor, if I remember correctly. Yeah. Yeah. I think you chatted with my co-founder back in the day. I think that was maybe six years ago, seven years ago now. But yeah, we built the first no-code tool for web design. Yes. Isn't it interesting now that we're sitting here in the age of no code becoming vibe coding? Maybe you could explain like that transition and the impact it's having on the startup and business communities. Everyone's vibe coding.
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19:40In the past, no code was just really just pretty small. It was kind of niche, like relative to where we're at now in the AI cycle, right? So it's just totally different ballgame. There's still a world for no code, in my opinion. You know, you still need some really fine tuning, right? But I think it's the difference between, you know, a scissor and a scalpel, right? No code scalpel, scissors, you know, get you really quick and you can make some sharp cuts.
20:07Lon Harris:When you're building a startup, your legal paperwork is spread out all over the place. Entity formation here, fundraising over there, cap tables, contracts, it's endless. But paper finally has a solution that's going to save you so much time and so many headaches. Papers introducing smart entities. Here's how it works. You tell Paper what you need to do and their pre-built agent takes care of all of it. That's it. This is not some chatbot you need to provide with a ton of context. Nope. Paper is an AI native platform that's going to manage all of your startup's legal work. That means no more switching between disconnected tools, keeping track of hundreds of documents and way less busy work for you to stay on top of.
20:49Lon Harris:That's why paper is already the legal backbone for thousands of startups and funds. Right now, founders using my link, getpaper.ai slash twist, get their cap table free for one year. What an amazing deal. Or two years if you're switching from Carta. If you're building a venture-backed company, it's time to build your smart entity on paper. So tell us, you got a new startup. What are you working on? I started Ploy about 11, 10 months ago, and I'm continuing the journey that I started at Webflow. So the premise is starting with the website. I want to turn it into your hardest working employee. I want to make the website, help you find customers, tell you who's coming to the website, and then help you grow your business just like completely autonomously.
21:38And my central thesis here coming out of Webflow is that like the website is just this nexus for data for customer interaction. It's like the last bastion of what you, the business, can control and tell a story to the world. And I really care about that. So, you know, we're building this super powerful AI website platform. But from there, we can help you run your ads. We can help you find your customers. We can help you do everything. We can tell you what they're doing. And the premise is that one day, like, I believe that AI is just going to create more businesses. And that these businesses ultimately really could use a lot of the things that the most sophisticated marketing teams in startups are using.
22:22And I want to kind of democratize access to all that.
22:24Lon Harris:Yeah, and you did see that with Shopify, Squarespace, everybody kind of evolving. Wix, I think. Hey, we have to add e-commerce. Hey, we have to add a calendar scheduling for massage therapists or therapists or whoever, you know, has a thing. And it's just like, wow, for 20 bucks a month, 30 bucks a month, you can have everything that used to cost 20 years ago, like$100 ,000,$50 ,000. And 10 years before that, you would have to pay a consulting firm like Agency and Razorfish$500K to$1 million to do a document lawn. And then they would spend$5 million actually building your business online. So here we are.
23:03Lon Harris:What is the pricing here, Bryant? And how does it work? How do you make money? It's totally nutso. So like you said, you would have to go pay a WPP, Razorfish, AKQA, half a million dollars. If you're Audi, you used to pay them like$28 million a year just for digital. But you can actually just get started for 50 bucks a month, employee. Amazing. Well, we'll build your site. You know, we'll create something that looks better. Bring it up to modern standards. We have something that we've spent a lot of time on called Deploy Site Slurper. We'll slurp in your existing site, all the assets, and then we'll bring it to play.
23:43And then from there, we'll migrate it and make sure all the content is there so that you can get found. You could get cited by ChatGPT. And then we can do all the things to grow your top of funnel and move customers through your pipeline.
23:57Lon Harris:So$600 per customer per year. I'm sure there are some upsells in there based on something. There's some upsells. Yeah. So maybe you can get it up to$1 ,000 a person. This is a hard business to do blocking and tackling. $1 ,000 a pop per year, maybe$3 ,000 or$4 ,000. You can't have a sales team doing it like Oracle can have a sales team or Salesforce can have a sales team. So talk to me about your go-to-market function here and how do you get customers in a market that's, my lord, talk about a crowded market. You're going into like, there's dozens of startups doing AI website building, and then you have everybody else who's got, you know, millions of websites are already hosting.
24:35Lon Harris:So how do you as an entrepreneur stand out in a really crowded market? I think the benefit that I have, maybe that other founders don't, is that I am not in a rush to make money and I'm playing the long game. You know, I believe in the tens of millions of sites and businesses behind them that I could potentially power. And I'm building for like years in the future, right? Where a world where agents and just the model capabilities can do so much. And of course, we have companies that are paying us six figures and we're powering very specific workflows for them. And ultimately, I think like with the cost of inference going down, with the ability for, you know, customers to buy a product that's truly aligned with value.
25:23You know, the 50 bucks a month is just a starting point, but we have really sophisticated users running really sophisticated workloads that are paying us$10 ,000 a month. So really kind of like scales based off of the complexity of the company, complexity of their workflows, how many customers they're trying to go after, employee can scale or pricing and packaging to that.
25:45Lon Harris:So that's the secret here is you're not just putting up the website, not just optimizing the website. You really want to get customers. You're saying, hey, we'll take some responsibility for driving commerce. Outcomes. Yeah, outcomes. Exactly. And I think that is the really exciting thing because when a roofer finds out about Ploy, it's like, oh, man, I've been meaning to update my website for years. I hate it. It's got the worst form. It breaks half the time. you know there's huge opportunity for me to just take that status quo with their broken WordPress site for example bring it to ploy make sure our agents are constantly monitoring it making sure that people are filling out the forms the best way but then also making sure the site can be personalized the audience right everyone's talking about the agentic web and building websites for agents but we even haven't haven't even built the best possible website for humans yet and in my opinion that's like personalizing the site, making sure like your copy, your content and everything really speaks the right message.
26:50Lon Harris:So let's do some startup questions here. Why go back to Y Combinator if you're like a third or fourth startup and give them that incredible 7 % for 100k deal? Or do you like, I've heard that they'll negotiate special deals with alumni? How does that work? There are some advantages to being a repeat unicorn founder. There are also advantages for being a founder in your 40s as well. I think like the two things added together, you know, actually drew me back into YC even harder. So like you talk to startups and founders all the time, like the way companies are being built nowadays is totally different than 2013, 2011.
27:31So I really wanted to just get into the thick of it. I was like, what are the most AI pilled founders doing? What are the craziest things that they're coming up with for sales, go to market, harness engineering, token maxing, you know, agentic development, like all of that is happening at like warp speeds at YC. So, you know, the alternative was for me to go and kind of go figure out that. But like, once you're in the batch, you know, you feel a bit of that FOMO, right? And I think that's also for me, you know, being a bit older, I want to have that young gun energy you know i think there's no better like testosterone booster than being around a bunch of other 22 year olds that are like working super hard that have like crazy visions of what they're trying to tackle and i'm just like okay that's that's where i want to be i want to just double click on something you said because we we've talked to a lot of companies that do variations on what ploy is doing like especially in terms of ads like you tell us your product and upload a bunch of photos of it and we're going to make you AI ads.
28:37And a lot of what comes out, and I'm not saying this is true of Ploy, I'm saying in general, you get like that kind of samey, it's like a girl and she's holding the cosmetics and it's a little cartoonish and she's holding it up to camera. How do you avoid that? Like, what are you doing at Ploy to work with these businesses and really to figure out how to personalize and customize what you're outputting for that person and that business so it doesn't just look like you know slop so the the biggest differentiator with ploy and everything else out there is we start with the website and if you think about it the website is like hopefully the the prime manifestation of a company's brand and from there we create a design system that can be used not just in the website, but also for ads.
29:27So for example, like if you are, I don't know, a big, you know, AI company, base 10, together AI, like you really, really care about how your brand motifs of these shapes and colors are showing up. You can't just throw that into an image model and expect like a perfect ad unit to be created. So this is where we go the extra mile. We create this incredible production-grade design system for you. We'll understand how to use it based off of the examples that you already have. And then we'll create really, really clean, locked into the brand ad sets, ad units, and web pages and the landing pages after you click through, because that's also extremely important, to make sure all of that is super locked in and on brand.
30:11Lon Harris:A lot of people think there is a binary choice, be a capitalist who supports growth or care about the environment and the natural world. But these two ideas don't have to be in opposition. Our friends at the Conservation Fund believe that you can protect land, wildlife, and our shared access to the great outdoors while also providing important economic opportunities. For 40 years, the Conservation Fund has been acting quickly to protect at-risk land and important wildlife habitats while also actively supporting local communities and, this is key, creating new jobs. The Conservation Fund already protects over 9 million acres across all 50 states, proving that we can watch out for the environment and keep our natural surroundings in balance without endless gridlock, debate, and politics.
31:00Lon Harris:And this isn't just Elantra scooping up property and sitting on it. They're working alongside permanent stewards who will find practical uses for these important spaces without destroying them. Find out more about how the Conservation Fund is changing the playbook at conservationfund.org. SEO and Agentic Commerce, what are your thoughts on how that's all going to change now? You probably have read Amazon is trying to block people from using agents. Good luck with that. Shopify is engaging people. What does everybody having a half dozen bots doing work for them autonomously, what does that do to the open web and web-based businesses?
31:43I actually think there's going to be several large companies that just solve this problem. So if you're thinking about it, I'm sure J-Cat would want to invest. But essentially, the world that we're in is that it's getting extremely difficult to determine who's actually a real user or not. But ultimately, if you're a business, you actually care about both. So currently right now, based on the stats that I looked up, 50 % of traffic is from agents right now, which is wild. And about two years ago, it was only 14. So it's just like the proliferation of this. There's going to probably be a moment in which 90%, 95 % is all agents.
32:27So I think that's just like on the absolute scale, but there's still going to be humans that visit the site. There's going to still be a human that wants to be able to establish a brand connection to the business that they're transacting with. So I still believe in the power of a brand. And I think like agentic web and where we're going is that businesses that don't necessarily evolve to accepting the reality of, you know, JCal's agent booking a resi reservation or my agent trying to reserve a soccer tennis field. I think those are going to become, I don't think there will become issues because I actually think these agents are getting so smart at browser use that they will impersonate the user.
33:15They will use residential IP proxies to get around, you know, the IP restrictions. And then ultimately, I think it's just going to look more of the same. So I actually think there's just going to be like this big chutzpah about agentic web. But then, you know, everyone's just going to be going back to using the web.
33:32Lon Harris:The browser, you know, seems to be or having a, you know, in agent browser. I don't know what we're calling it these days. Virtual browser. Headless browser. Yeah. Headless browser. Like it does change everything if it can remain logged in. Right, Lon? You've been having this experience. The GrokBot experience versus the OpenClaw experience, it couldn't be more different. Like I log GrokBot into whatever website I want one time. It's in there forever. and I could just ask it to go look things up or do things and it's totally autonomous in a way that none of the bots working out of my sort of slack ever ever were like they yeah they've opened claw realized right it was like open claw was this incredible head fake right brent brent brian street sorry i keep saying brian but all good all good i mean but you know that's that's our central premise too which is like we want to put all the agents inside your website that's something that no one else is doing.
34:30And, you know, our belief is that all this data that is in your CRM that comes to your website, all of it is incredibly additive. So like, you know, you can just, you know, for SEO, you mentioned, you know, it's now going to be really easy for you to just write net new content. If you have Ploy hooked up to your granola or Zoom recordings, You're talking to startups. You're having in real life conversations. But that should live on your website, right? If it's valuable. So the premise is that you've got all your bots that help you do all these other things. But employee can help you take your in real life memories, conversations, and surface it in a digital way.
35:18That's going to raise your visibility.
35:20Lon Harris:Like a chief of staff or a content marketing person who works at your company full time. And they're like, oh, you said something intelligent. You had a great discussion here. We should codify that into a blog post, a short. Exactly. And then from there, it can go be used for like sales decks, sales enablement, and all these other use cases to really grease the wheels. How do you think about fundraising as a serial entrepreneur who's had success, made a little bit of money yourself? Do you even bother raising money early on or just fund it yourself so you don't have to deal with it? Do you have like a crew that you want to reward with early equity?
35:53Lon Harris:How do you think about fundraising at a crazy time like this and as a serial founder? Good question. Well, I think a big part of it is I think I wanted to be just really generous with equity from the get go. I think there's just so much hard work in the early days that, you know, early employees, I'm sort of treating as many co-founders, many of them. So like I want them to be to be extremely invested in the journey. And then on the fundraising side, I kind of skipped a pre-seed and seed and raised a$27 million round out of the gate. I think that will just give me a lot of time to play the long game.
36:38And I think that's really important because the ground is shifting beneath our feet so quickly with AI that it can help us weather any type of hiccups or huge leaps and model improvements.
36:54Lon Harris:This is so tactical and important. important. If you are a serial founder and you see a market like this, which is, let's call it what it is, it's top ticking, it's disconnected from reality often, there's a ton of FOMO. When there's sunshine and you make the hay, you put the money in the bank account because the people who don't, when there are some headwinds or platform shifts, you have time to figure it out. And you learn that as an entrepreneur. Capital as a weapon was Travis's big innovation at Uber, among many innovations. But that was a significant advantage in beating DoorDash and Lyft and just dominating everybody because he didn't have to think about profitability in a specific region, whether it was China or Las Vegas.
37:38Lon Harris:He could just use that capital as a weapon. And if you invested in his company, he could invest in the competitors. So he just took everybody's money, all companies. Do you know how he got his investors to do that? Did they have them sign something? Because that That happens all the time now, right, where VCs are investing in this company and turn around and big check in the next. I don't want to say, but, you know, he had a system. Yeah, for sure. And I don't know if I should speak for him on the mechanical nature of that. But it is a sharp elbowed kind of situation where, hey, if you're in us, you can't be in other people.
38:20Lon Harris:That has left the industry, Bryant. You and I came up at a time where if you invested in Lyft, you couldn't do Uber and vice versa. If you invested in Airbnb, you weren't doing one fine stay. It was considered uncouth. But because everybody pivots and winds up in the same four businesses, essentially, how would any VC be able to tackle this? You just have to create a firewall. In fact, didn't, Lon, you can check here as my dutiful news reader. There was a A16Z federal investigation about them being on two boards in the same vertical. Yes, I remember this. That seemed a little fugazi to me. Yeah, the DOJ probed Andreessen Horowitz over board seats.
39:03The Justice Department launched a probe regarding the firm's partners serving on the boards of competing companies. The nearly year-long investigation focused specifically on the firm's board seats at Databricks and then 5Tran, which combined with DBT Labs back in June.
39:18Lon Harris:I mean, but they own, I don't know. What's your take on that, Brian? They own 5 % in each, 6%, whatever. And they create a firewall internally. Does anybody care? Or was this like a competing venture firm? I'll be honest. One of the people at one of the firms, like a CFO who's disgruntled, tips off the DOJ. I don't understand the provenance of this. You tell me. What's your take? What I think the investor take is, and then I'll give you the entrepreneur's take. As an entrepreneur and founder, you pour everything into your company, and it is your entire life. And to see your board member, for example, go do a huge round in a company that is directly competitive to you, that would rub me the wrong way really badly.
40:05Like I think I would, you know, figure out what I could do to sever that relationship. But if I was an investor, you're a capital allocator. Are you breaking any big rules? Are you doing your fiduciary duty? I think like this is where the line between honor and, you know, DPI kind of conflict, right? There is no honor in DPI.
40:35Lon Harris:No, I mean, and the other thing is as a VC firm, I know Sequoia and the top ones who get to look at every deal, they have a massive conundrum. If you have essentially 100 % vision into what's happening and then you're limited to making one bet in a space and you bet on the number two or three, Sidecar, Lyft or Postmates or Just Eats or whatever it is versus DoorDash versus Uber Eats, like that all of a sudden you're fund is screwed. So, and how do you know in the seed series a space, which one's going to be the 80 % market share Uber or Airbnb? You just don't. That's why I think series a and series B to me get a pass.
41:18But if you're writing big checks out of a growth fund, I don't know, Jake, how do you think?
41:25Lon Harris:It's, it's dicey. It's dicey. I think what they're saying now is like, oh, our growth thing. That's like public market investing. Don't pay attention to it. But you're right. And you know who was the master of this was Masayoshi-san at SoftBank. He came famously, this is all public, we'll find a story about it, but he came to the Uber team and said, I want this much equity. I want to pay this dollar amount per share. It was like low 30s. And he went to all of us and said, I need you to sell me your shares. And if not, I'm going to put this five or 10 billion into Lyft and DoorDash. But he'd already done DoorDash.
42:02Lon Harris:so this was like a you want to talk about a gun to the head uh and i was like sure i'll sell masa yoshi son 20 of my position 10 you know before the ipo i was like i'm waiting on this anyway but a lot of us were like yeah we need to get masa on board with this because nobody had ever raised a hundred billion dollar fund like he did with the the vision fund that was some hardcore Masayoshi-san. And when they told another person who was a bigger investor than me, Masayoshi-san just said to him, no, DoorDash, not competitive. Not competitive. And they said, no, we have Uber Eats. We're literally going after them market by market.
42:38Lon Harris:We're competing with them for, you know. No, no, no, no. It's not competitive. It's not competitive. He just like literally kept saying it over again. Not competitive. That was the entire story. This is a good cautionary tale to founders, right? Because I just think like there are very few things that a founder can do. And ultimately, you just have to control what you can control and worry about just that, which is building a good product, think about distribution and all these other externalities are just, unfortunately, you have to kind of put on a stoic sort of mindset and just kind of blaze through it.
43:16Lon Harris:I mean, if your destiny is not going to be made or broken either way in all likelihood, you know, by these kind of on the margin transactions. It could be, but all likelihood, probably not. And the more time you spend sweating about your competitors and not focusing on your own customers is like, your customers do not even know your competitor's name. They don't even know six other features you want. It's just people are, and this goes for life too, Juan. Like, I remember one time, I've told this story before on the show, I was at like a public event. I was young. I was doing my Silicon Island reporter.
43:51Lon Harris:And I, you know, when you slip on a step and you kind of bah, bah, bah, bah, and you catch yourself with the rail. I literally did that going down, like, you know, into this party on Wall Street. And the whole party turns and looks at me as I'm like leaning back and caught myself right before it. And I pull myself back up. All the chatter stops. And then everybody just, when they realize I'm fine, turns around and the chatter goes back up. And this was a seminal moment in my career when I realized, as embarrassed as I was in that moment, I was like a 26, 27-year-old J-Gal in this hall of power who just basically flopped down the steps.
44:31Lon Harris:Nobody cares. Nobody's ever going to remember it. Now, I remember when 100 people are looking at you like, oh, my God, are you a klutz? Yeah, nobody remembers anything. Nobody remembers Mahalo. They remember all in. Nobody remembers these three or four investments. they remember Uber and Robinhood. And to be honest, I'm starting to forget all the things in between the projects that didn't work out. They're like, I met you doing this project. I'm like, open Angel Forum. Oh yeah, I did that. Yeah, for two years I had. Yeah, it's a weird - Angel investors get together before AngelList to see your startups.
45:03It's a weird form of self-flattery. We always imagine that other people are constantly thinking about us and mulling over what we're doing and worried about us. Nobody's thinking about you ever. Like that's just you, that's ego. Like other people, in the moment you're out of their field of vision, they're on to the next thing.
45:20Lon Harris:Hey, let me ask you a question here, Bryant. How do you think about partnerships with the frontier models versus building your own model and not giving them your intelligence? Obviously, a big discussion in the last six months, but really in the last three, I talked to Levin Labs. I talked to Figma. I talked to Lovable. They're all like, or Harvey. They're like, we got to build our own. we got to fork deep seek we got to have our own model training because we can't give this to the frontier because at some point open ai is just going to be like we have a website builder and they're just going to go scrape your website and build the website builder and copy all your innovations so how do you think about educating open ai and anthropic on your innovations do you use the frontier models or sparingly we use the frontier models right now um simply because you know we get the best performance out of them um and then also just like with where we're at in our stage of the company we only launched like two two months ago three months ago uh so it's just really hey like our our number one constraint is just our number one focus area is just like hey let's go get employee out there in the world make sure people know about it and hopefully they can derive value from it so we are not concerned at the moment of what you know open ai can do with our data um maybe eventually but you know transparently we took the opening i deal because we figured that by taking on all these credits up front and i don't think there's any like special data sharing provisions or anything like that but like tell everybody about that deal sam came and said i'll give you two million credits at a hundred million dollar valuation or something on 2 %?
47:00No, it was an uncapped note, no MFN. Oh, okay. Yeah. So Sam came, offered that in the spring, every YC company, this deal for like one and a half million credits and uncapped note, no MFN.
47:18Lon Harris:So what's the cash value of that? Oh, 2 million in tokens. Got it. Correct. So he owns, if you closed at 300 million or whatever, 400 million, he owns whatever it is, 50 basis points in the company, and then you have OpenAI as an investor. Yeah, exactly. How many people do you think are taking that deal? I think a good amount. I think a good amount. I think we have a good portion of my batch took it. And I think, as you know, J-Cal, companies at C stage is like, hey, path to default alive, right? Path to growth. and you know i think oh look there i am in the uh be careful warning uh one day could have grown starters ideas yeah that's what i said yeah fair warning but opi has so much data right i actually don't think the data that ploy has is necessarily like crazy valuable to them you know they have massive data sets with really sophisticated things um i think the the the innovation employees, how we're packaging everything.
48:25Like employees, like all batteries included, right? It's not just an AI website builder. Yes, it is. And it's a really good one at that. And it's probably like, you know, the only one that does what we do. But you know, it comes with a super base, it comes with visitor enrichment, it comes with workflows, it comes with, you know, you could go build a CRM on top of it. So it's just like so broad in terms of what we're doing with it, that it's really the entire platform. And I don't think like our traces or, you know, our prompts or whatever are actually that valuable.
49:01Lon Harris:Yeah. I mean, that's an honest way to look at it. You know, just, I remember Zuckerberg did a similar thing and I was like, do not, this is back in your day when you probably first went, I was like, be careful because he is the master at, you know, he's a mememic machine. Like he can copy something and make it better than yours because he's fucking really good at building product. And that one, I was like, hmm. But you're probably right. They probably don't have the time to even look at this. But you've got to be careful, folks. I think that the eventuality is going to be people running local models.
49:33Lon Harris:Hey, before I let you go, I saw you were explaining to folks on your socials, exchange-traded funds. If you're locked up into one stock with 99 % of your math, explain to me this and then go back in a time machine and explain this to me when my uber and robinhood shares got distributed what these are yeah i'm happy to talk a little bit about it but i'm assuming when you had webflow you did that yeah at some point uh so i mean these these are exchange for creative funds typically for public you know tickers right so if you are a exec or founder, you know, if you have a huge block of Robin Hood or Uber, you can essentially participate in these exchange traded funds to essentially put a portion of your highly appreciated stock.
50:19And in return, you get essentially exposure to an index of other tech stocks that other people have pledged or committed to the funds. And then you essentially get a, you get it, you essentially take a lot of that downside risk off the table by essentially exchanging that highly appreciated concentrated position for a broad-based index. And I think you also have to get some exposure to like 10 % of like a REIT or something like that for real estate.
50:53Lon Harris:And you don't have to pay your cap gains at that point. So if you had$100 million in anthropic shares, Lon, which I think that's kind of close to the deal you have, Lon. Yeah, right there. You could take$50 million of it, put it into an exchange-traded fund. They might charge you like a 1 % load-in fee or something. They have ways to sort of make money. But you've got to stay in it, I think, for five years. But if you weren't planning on selling it anyway, it's like a very interesting thing to do. You're building one, or you just know about it? No, Angel invested in one. My friend Shrikanth is the founder of usecash.com.
51:26There it is. Look at that. And use cash is the ability for, hey, you've got 80 mil of NVIDIA or you've got 120 million of open AI or 40 mil of Anthropic. You can essentially pledge your shares here and then you get a bunch of broad-based exposure.
51:46Lon Harris:Very cool. All right, man. I'll let you get back to it. Congratulations. You're hiring. Where can people go to find out more? Yeah. We're on ploy.ai. So you can just log in. You can pick up what website you're coming from. We'll slurp up your site. We'll rebuild your site. We'll migrate your site over. And then from there, we can turn it into a growth machine. So we'll help you find customers. We'll help you improve your SEO and AEO. We'll help you deliver revenue, leads. And it's always on, right? So it's constantly experimenting with your site. It's helping you run your ads, helping you optimize your ads.
52:22um and yeah it's it's it's been really exciting we've got over a thousand customers already that have been starting to pay us we only launched a couple couple months ago and you know we've got all these expert ploy books that are built in so beautiful you know folks like myself and other growth practitioners have kind of really imbued in the platform all these like really hard learned tactics about how to optimize your your your website but then also optimize your entire top a funnel so that ploy can be the sort of last piece of go-to-market software out there yeah
52:58Lon Harris:so if you're an enterprise startup anything in between agencies go check it out ploy.ai we'll drop you off brian thank you for taking the time to share your experiences here and startups great to see you guys ah yes our offices used to be on brian treat in san francisco yes that's right i held on to my loft like a three thousand square foot loft you know what happened it was like they They were like, you're going to lose money on this thing. I paid like$600 a square foot. Now they're like, you're going to make a fortune on this thing. It's worth$1 ,000 a square foot now. And I'm like, wow, four years and this whole thing makes a huge difference.
53:32Lon Harris:San Francisco's back, baby. That's what they're saying. Bay Area real estate. Very strange. All right, let's set. We're going to go off duty. We've got another tech story. We've got a ton more news if you want to do more news. Give me options, and I'll pick one or two. All right, we could talk about Microsoft reconsidering co-pilot. We could talk about JEV, TypeSafe, and talks for a big valuation. We could talk about Oracle's troubled data center plans. We could talk about Optimus. And then there's Ando there, the startup that's doing AI native Slack. I want to hear about that last one. Tell us and show us.
54:03Ando.
54:04Lon Harris:I mean, Saks was working on something, Get Glue or something. Glue, yeah. Glue was, that was Saks' Slack killer. So yesterday, Ando came out of stealth with$20 million from Excel, Index, and Emergence. They're taking on Slack. It's a team chat app where AI agents get their own identities, inboxes, and permissions just like their human coworkers. So agents could join channels on their own. They could speak up without being tagged. They can message people directly when something needs attention. Founder Sarah Dew calls humans relaying agent work to their teams as meat proxies and says Ando is built to eliminate all that.
54:39This morning, Microsoft gave its own autopilot agents identities and email addresses inside Teams and Outlook. So this is obviously an idea that is out there in the world. My question for you, Jason, would be, how does a startup, I mean, if you were Ando and you're taking on a giant like Slack, I mean, what is the approach? How do you even get started at picking away at that kind of advantage?
55:03Lon Harris:You make it free for the first 200 users and you just take the startup market and then you grow with them. And when you hit the first 200 accounts are free for life, and then you charge after that, that would be a quite disruptive way to do it. Or you charge based on AI usage, or you come up with a flat rate. I mean, there's all kinds of ways to be disruptive in the space. But having a better product is critically important, obviously, first and foremost. So the challenges I've had with Slack is we have to keep throwing agents into it and getting them to work. And I had to like reach out to my guy, Mark Benioff.
55:47Lon Harris:And I was like, I need the enterprise version. And it's like 50 bucks a person per month. And I want to be able to see everything, including DMs and possible group DM chats, you know. So what happens is you and I are working on a newsletter product. There's channels, there's hidden, there's private channels. And then there's the other half of Slack, which is DMs and then like group DMs. So you got four people who decide, I'm not going to create a channel for this. I'm just going to talk about this project. And that's the most important thing. And then it's blinded. Your AI Oracle, as I call it, is blinded to that.
56:24Lon Harris:So in a major organization, finance, et cetera, healthcare, any corporation, they have access to everything. So they tell you, hey, don't send memes over your DMs. This is not the place to talk smack about your boss or to ask somebody on a date. And there's like a false sense of, or there was a false sense of like, oh, this is my data in my email when I'm emailing, you know, my friends about a party invite for my corporate email. So you have to educate young people on this. But if you go work at Sony or JP Morgan, whatever it is, they explain this, like, do not use your laptop. So I had to like tell everybody in our firm, like, hey, we're moving to this vision.
57:01Lon Harris:you should never ever do anything like this and we moved the slack over we exported everything and we kind of gave everybody a mulligan and when we moved over to like hey we're monitoring every computer we know what is being done on computers so if you try to download the entire database of our lps or the documents from like you know uber's siri seed or something like it's gonna have an alarm go off and the alarm goes to compliance and i get a they come to me hey this person just, you know, was like doing this thing. So that is the key with these systems is you, you can't make decisions if you don't have access to everything.
57:41Lon Harris:And Slack is like a roach motel at times. And I explained this to their team and they were like, Hey, we're going to hook you up. So they hooked me up. They gave me like the highest level at the price I was paying. But I said, you gotta, you gotta think first principles here. Somebody else is going to create something where you have access to everything. And here we are. There's going to be a bunch of people who are doing this. Sure. I mean, yeah. Like there's one of the most crowded spaces that we talk about on This Week in AI at this point is like enterprise agents that help your team organize.
58:15I mean, it's like everybody is crowding into that area right now.
58:20Lon Harris:I mean, it is everything. And did they mention their pricing or not? That's what I'm most curious about. Did they mention their pricing? That would be an interesting thing to know. I will see if I can. Pricing is where it's disruptive. Access to data is where it's disruptive. This is not something unique to Salesforce or anyone else, but they do try to make it hard for you to get your information out so that they have you forever. I'm being told that they are not yet publishing their pricing. Their public site is still a wait list onboarding rather than self-serve plans. There's no per seat. We don't know yet.
58:56It's just a wait list for now.
58:58Lon Harris:Free is the way to go. Getting influencers is the way to go. So I would go right after startups and VC firms. And that would be the greatest way to do this. And then, man, I would be very interested in a version of this where I could build my own AI, local model, server model, open source, and not put the entirety of my data into Claude, into OpenAI, right? So we talked about this over and over again. So that's the other vector I think they should be doing. Yeah, I mean, it is. I know that it is agent agnostic. So the idea is that it's an ecosystem, and this is even on their site. We don't expect to build every agent your company uses, and it should be the place where the best agents, ours, yours, or anyone else's, can work alongside your team.
59:49So you could pull your codex in, your GrokBot in, your Muse in, or what have you, and they can all collaborate in Ando is the idea.
59:58Lon Harris:I looked at doing this as a startup myself, like doing an open source project. There is an open source version. Let's see. Open source for Slack. Matter. Mattermost? Mattermost. Mattermost. Yeah. But Mattermost still charges a lot. So it's open source, but there's like a hosted version. So it never took off. I think they should just go for it here and make it free and then figure out later, like at two, I mean, maybe, or maybe make it like $500 a year for literally make it$500 a year for up to 100 people and$5 ,000 a year for up to 1 ,000 and just make it super easy. Just undercut everything. But three tiers, super easy.
1:00:52The product is presently aimed most directly at teams of up to about 30 human users plus AI agents and coworkers. So above that, you could say 30 or below free. And then once you start moving above that, maybe that's where the tiers kick in. Looks like I have to invite you.
1:01:08Lon Harris:I'm signing up for this. Oh, let's, yeah, let's try it. Five team members. Oh, my God. What a pain in the neck. But I will, I have been looking to experiment with something like this because it's time has come. Okay, what's going on with Optimus? Tell me about that. This morning, the information reported Tesla now builds several hundred Optimus robots a week, roughly 10x their Q2 pace. Managers reportedly want an automated line making over 1 ,000 robots a week by year end and eventually getting that up to 20 ,000. The hands on the robots are the bottleneck. Over 100 screws and small parts per hand and forearm still assembled by hand.
1:01:46Tesla ended the Model S and Model X to free up this line and plans to lease early robots rather than sell them. I remember Elon talking about the hands last year at All in Summit and how complicated it was to do the hands.
1:01:58Lon Harris:I think he's going to have the best-selling product of all time. I think self-driving is, because it's taken so long, self-driving, not just by him, but by everybody, because you have a serious safety issue. I think there's going to be a lot of competitors. It's not going to be one person wins it all. I think he wins 40%. I think Uber plus 20 partners wins like 30%, 35%. I think Waymo, if they go it alone and are not part of the Uber network, I think they win 10%, 20%. They skim the most profitable cities and have a very nice business. But with this, I could see them having much, much larger market share.
1:02:40Lon Harris:And I think people will pay$5 an hour for one of these robots. So if it works 20 hours a day,$100 a day,$36 ,000 a year, if that thing lasts five years, you're talking about$150 ,000, and it'll probably cost$20 ,000,$30 ,000,$40 ,000 to start and then go down from there. So you just think about how profitable this thing could be. It's going to be nuts. What are you envisioning? Who are you envisioning as like the ideal customer for that? Like I own a warehouse. I own, or is it like, you know, like around the ranch? Yeah. No, I mean, Target, Amazon, Tesla factory, BMW factory, anything that's dirty and hard and painful, anything where a human is going to get a, you know, reoccurring injury because or their elbow, carpal tunnel injury, anything that makes you want to kill yourself when you do a double shift, you know, security.
1:03:30So the dock workers, that's who we're going at with this thing.
1:03:34Lon Harris:I mean, if you look at the docks in China, they are fully automated. In Japan, they're moving to full automation. They have a huge robotics thing because they don't have anybody to work at them in Japan. They're in population decline. In China, they do have a lot of people to work at them, but they want to have them automated because they need to get stuff out of there faster. And so docks would be really good to automate. If you pull up like a YouTube video, Jacob, of like automated ports in China. When you see some of these automated ports, it is next level. They are taking containers off of ships, putting them onto autonomous sleds.
1:04:13Lon Harris:It's bonkers. There you go, yeah. It's super bonkers. Oh, we got it now. Here we go. There we go. Yeah, so I don't know. This is China, yeah. I just was thinking of like - They have these sleds. You see the sleds? Yeah. When I was a kid, like the old guys who were always like bent over and bad backs and knees, they were always like the dock workers. That was the hardest job when I was a kid, I thought. And you think about what they're building out in China, they have to get so much stuff off that island 24 hours a day that I just don't think humans can compete with the demand they have. So humans will be supervising, human in the loop, obviously still got to supervise this stuff, But, man, they are.
1:04:51Lon Harris:Yeah, they make our ports look ridiculous. All right, let's go off duty. What do we got in an appearance this week on the Ezra Klein show? I've got to hear the doc at Jensen Huang of NVIDIA. He said it doesn't matter if kids can't do basic math anymore because maybe those skills don't matter as much in the future. And then he told Ezra Klein that he doesn't know his own address. Can we roll? Can we roll this clip? I'm trying to try to get a kid to do long division right now. You know, the multiplication table is starting to be forgotten. Doing square roots. My goodness. I mean, it's just basic math is being forgotten.
1:05:27Lon Harris:Does it matter? That's my question for you. Yeah, I don't think it does. I don't think it does. But there must be some set of skills that matter. Oh, yeah, yeah, yeah. But maybe not those. We're going to discover new ones. Just maybe not those. I actually don't know my address. and i and every i don't really believe that to be true it's it's completely true and and janine will tell you and laurie will tell you um uh one day i had to pump gas and it was a few years ago and um i they needed my my zip code and i panicked i didn't know my zip code i had this exact thing i don't know my telephone number but i had that happen i forget these things um I can live with it.
1:06:10I feel like I'm a little with Ezra Klein. You really don't know your address. You really don't know your address.
1:06:16Lon Harris:I know my address, but I literally, he may also be suffering from, you know, having four homes or three homes. But I have had times where I forgot my ski house address and I have to look it up. Or certainly if you ask me what my zip code was at the ski house, I don't know it off the top of my head. I do know at the ranch now. I don't know at my office. and I have forgotten my phone number. So I think what's happening is certain things are atrophying because you don't have hand speed anymore. The act of dialing a phone number reinforces it every time. But if you have everything, like I forgot my wife's phone number the other day, I had to look it up.
1:06:51Lon Harris:And I'm like, gosh, yeah, we had the same phone numbers, our whole relationship over 20 years. And I'm forgetting both of our phone numbers. I would look at this and the math thing as calligraphy, as handwriting, cursive? Cursive, right, yeah. Yeah, so is it necessary for us to learn handwriting and cursive? Is that going to be a skill that's critically important for my kids? I don't know. I still think we should teach it to them. I still think we should still teach them the basic math things. I think Jensen is struggling with that and doing a thought-provoking question. I don't think he's saying, get rid of all math, get rid of all, or I'm not saying get rid of all penmanship.
1:07:34Lon Harris:I like the idea of people having great penmanship. And I can tell you, young kids do not know math. They do not know penmanship. That's why I'm in love with the Montessori educational system, which really reinforces a lot of this like hands-on stuff and less screens. And you can always learn the screen stuff. So I think parents should do Montessori type things where the kids are interacting with each other, doing projects, physical stuff, get that foundation. And then, you know, for the last hour of the day, you can go online and do stuff. But I mentioned this study, I think, on All In. There was a study of brain scans for people who used AI to write their paper, people who used search engines and were cutting and pasting, and then people who were raw-dogging it with a pen and paper or typing it in a word processor, brain activity was just like zero, like 5%, 50%, and then boom.
1:08:30Lon Harris:And here it is. I guess this is the study here. And there was actually pictures of the brain scans in this thing. So if you scroll down, you might even be able to see that. There you go. And so they were looking at these and you see the LLM, you see search, you see the brain activity. Dynamic direct transfer function EEG analysis of alpha band for groups. I think that's the technology. LLM, search engine, brain only, including p-values show significance from moderately significant to highly significant. In other words, your brain is firing on all cylinders and we're just going to atrophy. By the way, we already have an analogy for this.
1:09:09Lon Harris:You sit at a table at work, click clacky, click clacky. Your vitamin D goes to shit, as we talked about. You get fat, you get a big tire around your waist and you feel depressed. Why? Because you need to go out and run and get. And then if you just work and then go home and Netflix and chill, now you're in double situation because you didn't go out. You didn't have friends. You didn't laugh. You didn't socialize. This is why so much of the country is on SSRIs and trying to solve for anxiety, depression, sadness, melancholy, whatever it happens to be, however you want to describe it. It's like, oh, I got to take a pill because I have a chemical imbalance.
1:09:49Lon Harris:Chemical imbalance is probably because you're not getting enough sun. You're not sleeping. you're not doing socialization, you're not meditating, and you're not doing physical activity. And I guarantee you, I work on this with my kids, I work on it with myself. I say, if I'm feeling out of sorts, how did I sleep last night? How's my diet? How's my exercise? How's my socialization? And how's my meditation? The fifth one maybe just might be me virtue signaling or whatever, but I've had a good experience with meditation. Just I can tell you if you're listening to me, you feel down and out and you feel melancholy, just please do all five things I've said for three days in a row.
1:10:24Yeah.
1:10:24Lon Harris:Meet with your friends for dinner or lunch. Go do a physical activity with your friends. Go play pickleball, paddle, hike, anything in the sun. Eat a salad, some protein, no fried food, no sugar. Man, you it's going to turn around in 72 hours. Yeah. I mean, I have struggled with depression and I got off all the SSRIs or whatever. But that it is it like when you're when you're inside and you're feeling blue and you're down and you're depressed, the last thing you want to do is go out for like a walk in the sun. You're just like, oh, it's not going to make me feel better. I don't want to. That's the thing.
1:10:58It's resistance. You're going to reject it at first, but then you go outside, you just see, just seeing visually other people being outside, fresh air.
1:11:08Lon Harris:I could tell the difference in you since you got your new dog. Yeah. You get a new dog, you have no choice but to do two walks a day and somebody's going to come over and be like, oh my God, your dog's so cute. And then you're going to talk to a human being. That's why I brought everybody back to the office. Not because I'm like, I want to be a tyrant and have everybody chained to a desk. Because I was getting weird. Everybody's getting weird by not going out. And I'm literally moving to get closer to our office and moving our office closer to me. Because I want to be, I'm 45 minutes from the office or an hour.
1:11:39Lon Harris:It's a little bit when you have a ranch, you're pretty far away. I want to be able to just walk to the office. That's my ultimate goal, walk for the office. That's true. Or ride a bicycle. We're going to have to be at the Salt Lick. There's not as many options out there. Well, no, no, no. I'm going to move closer to the city, I think, and then keep the ranch for the weekends. So Sydney, sweetie, of course, she's in that sports gambling. I believe it's for a sports gambling app where she's almost nude. You know, it's very provocative. She's covering herself with the sports memorabilia or whatever.
1:12:10And a lot of women athletes got a little upset where they were like, listen, she's sexualizing being a woman athlete. and we don't like that. And we're just like men competing and stop making it sexual. So it's touched off a whole other round of people condemning Sydney Sweeney and people being back and forth about what does her body mean and what side of the political war is she on? And then we saw that you had tweeted your new take on what Nike's new campaign should be featuring Ms. Sweeney.
1:12:40Lon Harris:Yeah, so we had this funny conversation about Nike. Nike is like got kicked out of the - The Fortune 500, yeah. No, 100. Oh, the 100. And Palo Alto networks went in. And I was like, you know, they need to do something and shake things up. And, you know, you got this, just do it. I think you got to like go a little counter programming. You got to get somebody who's youthful. And you got to kind of confront people and shake things up, right? Kind of like we were just talking about with, you know, if you're feeling melancholy in this generation that's terminally online, you got to fight to go outside and do something.
1:13:16Lon Harris:like challenge that group because i believe part of the issue with nike is and also with restaurants also with spirits companies is young people do not go out they stay home they believe that they've had a play date when they're young or they believe they've talked to their friends when they do it digitally so my daughters i'm like hey let's do something with your friends and they're like oh you know i i had a play date with them yesterday i'm like oh they were here or you were there and they're like, no, no, we played, you know, Minecraft for two hours. And I'm like, oh, you're on your iPads.
1:13:47Lon Harris:That doesn't count. I want you guys in the swimming pool, on the ranch, going to a hike, something out in the world. So on all in, I said like, you know, come up with something like really to challenge people, do it or don't. We don't give an F. And they were all mocking me, et cetera. But I was like, wait a second. I'm a very good brander. I think this branding, I have never heard anybody come up with a better slogan for Nike that was challenging to the audience. And then I was like, well, you know, let me see if I can create some ads. So I saw the Sydney Sweeney thing and I was like, well, what if you put, I first started by using Grok to put these ads like on trailers or like, you know, on subways or whatever.
1:14:30Lon Harris:And then I was like, put Sydney Sweeney in here. And like some tools won't do that. But Grok was like, yes, sir. Look at this. Do it or don't. We don't give a fuck. And then if you just put a star in there for the you and like, yeah, just do it. Whatever, Nike. And, you know, she's looking at you like, hey, I'm doing it. You do it. I don't care if you do it or not. I'm doing it. Right. Show the next one. It made like a video of this with what it would look like in New York on the streets of New York. Yeah. You and I could run an ad agency and get paid a million dollars per campaign because I'm good at this.
1:15:06Lon Harris:Oh, look, and then they made her like into a video. She's moving like Harry Potter. Yeah. I mean, AI is sick right now. Do it or don't. We don't give an F. So anyway, rate my, because you're very objective here. Yeah, of course. What do you think? Is it too spicy? No, I don't. I think spicy, you have to be spicy in 2026. It's the only way to break through. I mean, I feel like what we're seeing with Nike is it's less anything to do with, you know, people are always trying to diagnose like, oh, Nike did a brand deal with this person or they said this or it's that. I don't think it has anything to do with anything specific they've done.
1:15:42I think Nike used to be part of this monoculture that doesn't exist anymore. Like when I was in high school, you were either like you were into Nike or you were into Adidas. And that was like it. Maybe there were like a couple of Reebok kids or somebody had like a British Knights shoe or whatever. But there weren't there weren't that many options. You sort of had like two or three acceptable options and you picked one that just doesn't exist anymore. Now there's like so many. Everybody's in their own little niche. Everybody has their own style. I don't know what you do if you're Nike to cut through that.
1:16:11But I do think this would grab people's attention, especially the Sydney. Like you picked the exact right celebrity for this ad because she is every everybody's really fixated on her. Everybody has a take on her. And that's what I think people miss is that a divisive figure is like better. Like somebody everybody loves is great, but somebody who everybody has an opinion on, good or bad, for marketing like this, I think is almost better. Like they're going to grab everybody's. It's like putting a Kardashian in your ad. Like they have lots of fans, but they also have a lot of people that are going to see that and get like a little riled up and they're going to pay extra attention because they don't like the Kardashians.
1:16:48And I think you've got to you have to play in that game now in 2026.
1:16:52Lon Harris:By the way, and just everybody giving her a hard time, I'm Greek, gymnos, G-Y-M-N-O-S. This is the ancient Greek adjective meaning naked, nude, unclothed. It is the root of the word gymnasium or gym. In the Olympics. Because they were, yeah. They were naked in the Olympics or lightly dressed. Same thing with gladiators. And they were celebrated for the ideal beauty of their bodies. They were essentially sexualized, if you want to use that, or, you know, if you don't want to use sexualization, they were an ideal. And that was, and it conveyed that you were disciplined and that you were ready to serve in the military.
1:17:39Lon Harris:So giving like her a hard time when, I don't know who gave her a hard time, but am I crazy or does Sports Illustrated do a nude issue? A lot. This came up a lot. that Sports Illustrated, they do the swimsuit issue every year, and then they do the body issue, which is athletes, male and female, naked. That's the whole idea is, like, they shoot, come up with clever ways to obscure their naughty bits, but, you know, they shoot the athletes without their clothes on. So a lot of people were saying that, like, well, it's already pretty sexualized. And, like, look, I get when it's, like, you know, 18-year-old gymnasts and dudes are being creepy about, like, their little outfits or whatever.
1:18:16Like, I get that that's creepy and wrong. Sure. Yeah, the Sydney Sweeney ad, you know, just like her holding footballs in front of her chest and be like, go bet on this app. Like, how can you be bothered by like, who cares?
1:18:27Lon Harris:It sounds to me like what they're upset about is that she's not an athlete and she did it and took the bag and secured the bag. That idea, I think it's the whole, I mean, I'm sure that is part of it, but it is also like. They're jealous that she's getting 10. How much did she get in this company? Oh, that's a good, that's a good. I don't, I haven't seen that information, but we can certainly. Because I think she could like, honestly, she's such a force of nature right now in terms of like a zeitgeist that if I was running Nike, I would literally go to her and say, I'll give you 1 % of the equity in this company for a lifetime deal.
1:18:58Lon Harris:I'll also give you$10 million a year in cash, but I'll give you 1 % ownership. You vest it over the next 40 years of your life, like every year. I believe she is an equity partner. They're not disclosing the deal, but it does sound like she's got some some some she's got she's getting a little taste of Novig, this platform. It sounds like this is what celebrities should be doing. You're a celebrity who could. Yeah. She partnered with drive sports prediction market startup. Novig is an equity holder and strategic partner. That's what they're calling it. If you have a massive following like Kim Kardashian, like her, you should be an equity owner.
1:19:40Lon Harris:You should create your own brands or take existing brands that you don't have an interest in starting and just say, hey, I'll do this for 10 years. I want 10 % every year I do one. But this is completely hypocritical. Serena Williams, Venus Williams, Dwight Howard, Chris Paul, Carl Anthony Towns, everybody has done this ESPN thing. So I don't understand the controversy, but OK, sure, whatever. I mean, it was OK for the Greeks. I mean, we're the greatest culture in the history of humanity. Yeah, I mean, I guess I could I could sort of see the complaints, but it's also you have to know at this point, if you are going to make a complaint about a Sydney Sweeney ad, you're just feeding the beast.
1:20:23Like you're just you're just drawing more attention to it. She's now making a lot of money off of this. Like being the controversial lady in ads is like obviously paying off hugely for her. So if you're not a fan of it, it's Streisand, yeah, you know, effect at this point. Like, just stop talking about it. The more obsessed people become with her, the more she's going to make that money. Here, pull that quote back up, Jacob. You just had a good quote I want to read. Pull that article back up. Yeah, British sprinter Amy Hunt was one of the people who complained. Sydney Sweeney, this is what women in sports look like.
1:21:02Muscles, hard work, blood, sweat, and tears. That's okay. So she's saying, yeah, it's like a cheesecake version of women in sports.
1:21:13Lon Harris:I'm surprised you didn't bring up the trailer for the new Tarantino. Oh, it's actually David Fincher. Tarantino wrote it. David Fincher directed it. Cliff Booth. What do you think? Looks good? Looks great. I can't wait. I mean, I love that character. I love that world that Tarantino created. I was super excited he wanted to get back. You know, it seems like Tarantino, he does these movies and then he kind of gets tired of them and he's right on to the next thing and he's kind of like losing interest. So the fact that he wanted to come back and write another script about this character set in this world, it's in late 70s Hollywood, which is going to be a very different time and a very different vibe from the original movie.
1:21:54And, you know, Brad Pitt and David Fincher, what a duo. Seven, Fight Club, Benjamin Button. I mean, they've made some pretty strong collaborations. So, yeah.
1:22:04Lon Harris:The further adventures of Cliff Booth. I wanted you to play the trailer with the sound off, guys. Yeah, let's say we could take a look. I mean, it looks gorgeous. I mean, yeah. It looks gritty. Seeing Fincher bring to Hollywood in the 1970s to life. That's the new Beverly, by the way. My old stomping grounds. Tarantino owns it now. Which Tarantino owns. And I guess he's now, I guess they're saying Cliff Booth is now a Hollywood fixer 10 years later. Right. He comes back. He comes back to Hollywood. when he's no longer working for Rick Dalton because he says Dalton got too fat for him to stuntman for him anymore.
1:22:36That's hilarious. What a dig to Leo. A little DiCaprio dig in there. Although there is still a lot of rumors that DiCaprio showed up for a day and that we may get a little like cameo Rick Dalton appearance. I mean, this thing,
1:22:50Lon Harris:he should be building the Tarantino universe as his like legacy. Just take all 10 movies and like, let's get a Steve Buscemi 20 years after Reservoir Dogs story. I don't know if Steve Buscemi died. Yeah, Steve Buscemi does, sadly. But there is, the early ones all had a lot of connective tissue. Like they mentioned the Vega, like Vincent Vega is obviously Travolta in Pulp Fiction, but there's a Vega brother mentioned. And I think Vic Vega is in Reservoir Dogs. That's Michael Madsen. And then there were red apple cigarettes that used to show up in all the movies. So he used to kind of do that where like they were all happening in the same alternate reality.
1:23:30He kind of seemed to get tired of that over a while. But I agree. You should do a movie that pulls together all these worlds.
1:23:35Lon Harris:This is my dream interview for the all-in summit. I put some feelers out. Oh, QT? Yeah. I really want to interview QT. I think he's just tremendous. He's living in Israel now. That might make it a little - I think half the time or something. Yeah, it might make it a little tough. I mean, raising his family, good for him. I think that's going to be great. I love this because it's got a 1970s Mustang Fastback, which was my first car. I had a Mustang Grande in mustard gold. You can pull it up. 1970 Mustang Gold. Yeah. Grande. If you look at that 1970s Mustang Grande, 1970s Mustang Grande, I bought it for$600.
1:24:18Lon Harris:And it was in mustard gold. and what made it really interesting as a grande was like their fancy one that's a vinyl roof so if you click on the black one on the side i had a black vinyl roof on this thing 351 cleveland and that's the brown one you find a black one in there at some point there it is that was no that's like a not a 1970 but anyway the 1970 is like a longer front it is crazy like this thing when you would hit the gas it's the one fourth third one down on the right yeah there you go that's the Look at this thing. Wow. It is like a shark, and it is a beast. It's literally two-thirds front engine, 357 Cleveland, 351 Cleveland, I think was the designation.
1:25:03Lon Harris:And I put a four-barrel carburetor, got literally five miles to the gallon. This thing roared, and I almost died. And I was coming on the Bell Parkway. I came around a turn. I hear a crack and a grinding. I pull off the Bell Parkway in Brooklyn. I pull into a spot. I look under it. and the suspension bars and the axle for the front thing is cracked. Right as I park and I look at it, it goes bang and it just breaks in half. Oh man. The thing is on the ground. I walk home. I come back two days later. It's been stripped. Yeah. There was nothing left of it. I mean, Brooklyn. It's lawn in Brooklyn.
1:25:38Lon Harris:In the 70s, yeah. Man, I wish I had like on the ranch, like a barn doe so I could start collecting these again. All right. another amazing episode of this week in startups february 25th we'll see you next time bye bye bye buddy
From the publisher
This Week In Startups is made possible by:
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Today’s show:
An OpenAI agent breached Australia's Medicare statistics portal in June, and it took 84 days for the Frontier Lab to publicly acknowledge it. Jason and Lon dig into whether this is an important cautionary tale about alignment, or if PM Anthony Albanese looking to join the AI conversation.
Then Bryant Chou of Ploy joins to explain skipping pre-seed and seed entirely to raise $27M, and why he’s taking his time to build his all-in-one agentic solution for running businesses.
Learn why Google is launching four TPUs into orbit for Project Suncatcher. PLUS, how many robots a week is Tesla now shipping with Optimus, and Jensen Huang told Ezra Klein basic math no longer matters. Is he right? Can we forget long division, at last?
Guests:
Bryant Chou on X: https://x.com/bryantchou PloyAI: https://ploy.ai/
Relevant Links:
Ploy raises $27M seed led by First Round Capital and Y Combinator (Founderland) → https://www.founderland.ai/articles/webflow-co-founder-launches-ai-marketing-platform-with-27m-s-mqj8o952
OpenAI's $2M-in-tokens offer to every YC startup(TechCrunch via Yahoo) → https://finance.yahoo.com/sectors/technology/articles/sam-altman-makes-mic-drop-212302858.html
Original Bloomberg report on the a16z probe → https://www.bloomberg.com/news/articles/2026-08-17/andreessen-horowitz-focus-of-doj-probe-over-board-directors
Google: Project Suncatcher's first test launch on SpaceX's Transporter-18 → https://blog.google/innovation-and-ai/models-and-research/google-research/google-project-suncatcher-facts/
ABC News (Australia): full timeline, from the June 18 breach to OpenAI's Sept. 10 email → https://www.abc.net.au/news/2026-09-24/ai-agent-accessed-australian-government-site-pm-says/107189078
Ando emerges from stealth with $20M to take on Slack (TechCrunch) → https://techcrunch.com/2026/09/24/ando-eyes-slack-as-it-builds-team-messaging-platform-for-humans-and-agents-to-work-together/
Google's $900M investment in SpaceX's $1B round, January 2015 (VentureBeat) → https://venturebeat.com/technology/google-confirms-it-put-900m-into-spacexs-1b-round
Tesla ramps Optimus to several hundred robots a week; hands are the bottleneck (Electrek, summarizing The Information) → https://electrek.co/2026/09/25/tesla-optimus-production-ramp-hands-ai-generalization-problems/
Jensen Huang tells Ezra Klein forgetting basic math may not matter, and that he doesn't know his own address (Kotaku) → https://kotaku.com/nvidia-ceo-doesnt-care-that-kids-are-forgetting-basic-math-because-of-ai-i-actually-dont-know-my-address-2000737092
Sydney Sweeney's Novig "Just Sports" ad and the athlete backlash, including Amy Hunt's comment (Yahoo) → https://www.yahoo.com/entertainment/celebrity/articles/sydney-sweeney-novig-ad-controversy-172900515.html
Nike exits the S&P 100 after 18 years (Fortune) → https://fortune.com/2026/09/08/nike-stock-plummets-sp500-market-cap-index/
The Further Mis-Adventures of Cliff Booth trailer: David Fincher directs Tarantino's script; IMAX Nov. 25, Netflix Dec. 23 (Variety) → https://variety.com/2026/film/news/the-further-mis-adventures-cliff-booth-trailer-brad-pitt-1236701901/
Timestamps:
0:00 Whoop fire alarm: Jason's dry-aged steak incident
4:45 News: an OpenAI agent breached Australia's Medicare statistics portal
12:48 Scraper or hack? Australia's PM jumps into the AI safety debate
13:31 News: Google launches four TPUs into orbit for Project Suncatcher
18:27 Guest: Bryant Chou of PloyAI
20:07 AD: Paper is the legal backbone for thousands of startup founders and fund managers - including Launch. Use getpaper.ai/twist to get your cap table free for a year - or two years if you're leaving Carta.
21:11 Ploy's thesis: your website as your hardest working employee
27:05 Why a repeat unicorn founder went back to Y Combinator
38:55 The DOJ probe into a16z's Databricks and Fivetran board seats
44:57 "Nobody's thinking about you": Jason's stair story
45:17 Frontier models vs. your own model, and OpenAI's $2M YC token deal
54:04 News: Ando wants to replace Slack with agent-native chat
1:01:08 News: Tesla ramps Optimus to several hundred robots a week
1:04:48 Off-Duty: Jensen Huang tells Ezra Klein basic math may not matter
1:08:31 The MIT "Your Brain on ChatGPT" EEG study
1:09:57 Jason's five-part reset: sleep, diet, exercise, socializing, meditation
1:11:45 Off-Duty: Sydney Sweeney's Novig ad backlash
1:21:07 The Further Mis-Adventures of Cliff Booth trailer
1:23:41 Jason's first car: a 1970 Mustang GrandeSubscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com
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