In short
WWDC kickoff reactions (Apple Intelligence/Siri, privacy claims, AI expectations), plus U.S. jobs/inflation market update and viral VC “horror stories.”
Guest backgrounds
No named guests in the transcript. Mentions include John Gruber (Daring Fireball) and Mark Gurman (Bloomberg) as discussed figures, plus Eric Sufert and Jonah/Groxon/Tyler/Jordi/Jane/Sam Henry Gold as commentators.
Key claims
WWDC is software-focused; Siri/AI will improve via “best practices” from existing LLMs rather than a breakthrough. Apple will emphasize “private cloud”/secure inference, with some processing on-device; rate limits/subscriptions may apply. Apple’s AI summaries may hallucinate but won’t change usage/churn much. Separately, May jobs rose 172k, unemployment stayed 4.3%, but inflation pressures could limit rate cuts. VC stories: disrespectful pitch behavior (e.g., sleeping VC), and “Sequoia scam” claims about tranched pricing and founders misrepresenting blended valuations.
Notable examples
“All systems glow” theme; “Siri button” expectations; Google search overviews as precedent; Apple “Operation One More Thing” against Mark Gurman; “Sequoia scam” (Mercor CEO Brendan Foody); Cloudflare CEO Matthew Prince alleging Vinod Khosla conditional investing; sleeping VC anecdote; older-men sleep study (median 36.9 minutes) and “bring the air horn” advice.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOWWDC Highlights and Expectations
0:45 to 2:05
Discussion of expectations for WWDC, including software updates and Siri improvements.
“I think expectations in a weird place, like they're high.”
AI Features and User Experience
2:05 to 5:10
Exploration of AI integration in Apple products and user interface improvements.
“or the interest build organically, right?”
Open Ecosystems and Apple's Strategy
5:10 to 7:40
Debate on whether Apple will embrace open ecosystems in their software.
“And it's something that Apple is, they don't really have to respond yet.”
Privacy Concerns and AI Integration
7:40 to 10:54
Discussion on privacy implications of AI integration in Apple products.
“to being something that big tech companies, social media companies, device manufacturers have to answer to when they're in like free form podcasts, basically.”
WWDC Reactions and Key Features
11:10 to 13:49
Reactions to WWDC announcements and highlights of new features.
“Gurman who had for 16 consecutive years obtained and published accurate details about Apple's products before their announcement has been neutralized.”
Apple's Data Capacity and ESG Compliance
14:00 to 14:33
Discussion on Apple's data center capabilities and storage options.
“So they clearly have a lot of data center capacity, and they've done a lot to make that ESG compliant, but I'm very curious about where that goes over time.”
Apple's Design Changes and Market Reactions
14:49 to 15:38
Exploration of Apple's design adjustments and market dynamics.
“Wait, so they're going deeper in liquid glass or pulling back?”
US Jobs Report Insights
15:40 to 17:06
Analysis of the recent US jobs report and its implications.
“hiring gathers steam, third straight monthly increase, slight decrease from the previous month, which was slight down from the previous month, but still in adding territory in the hundreds of thousands.”
Inflation and Rate Hike Predictions
17:08 to 18:49
Discussion around inflation trends and potential rate hikes.
“We will see where things go, of course, of course.”
Speculation and Market Behavior
18:59 to 19:29
Comments on market speculation and its historical context.
“Well, yeah, once the rates spiked off of like that 3 % jump, like the end of Zerp, it was like, OK, like there will never be froth again, certainly.”
Show all 13 chapters
Venture Capital Horror Stories
19:32 to 24:17
Sharing of various VC horror stories and perceptions of behavior.
“I didn't realize that he was the one that started this whole thing and kicked the hornet's nest and everyone came out of the woodwork with their VC horror stories.”
Lessons for Founders in Pitch Meetings
24:19 to 28:01
Discussion on strategies for founders to keep VCs engaged during pitches.
“Like a customer is less likely to like be overly friendly if they're not interested in what you're selling, right?”
The Power of Presentation in VC Meetings
28:01 to 29:28
Explore the dynamics and strategies used in venture capital pitches.
“Also, Vinod didn't fall asleep, so it's all moot.”
Transcript
Automatic transcript. May contain errors.0:03John Coogan:Two WWCs ago we were talking about Apple intelligence and it's all finally coming together. The package is finally being delivered. I think the response has been really good. Some of the guys on the team have been watching WWDC already. We have a bunch of folks calling in to discuss WWDC throughout the week, but let's give you the high level first, go through some of the immediate reactions, and of course we'll be covering that throughout this week. So Apple's annual worldwide developers conference started today and it runs through Friday. Tim Cook just kicked it off with an opening keynote. The theme for this year's conference is all systems glow.
0:40John Coogan:All systems glow. A little pun. We're finally getting answers about what the next version of Siri will look like. I think expectations in a weird place, like they're high. Everyone's expecting like this next version of iOS, which is what they're demoing. that's the main thing of the software version. This isn't an iPhone event. This isn't a hardware event. This is WWDC about the software. Everyone's expecting that the software will go through an actual transformation and the next version of Apple software will be good and people will be talking about how good it is because they will deliver on a bunch of things.
1:12John Coogan:At the same time, expectations aren't so high like going into Apple Vision Pro where people are expecting a breakthrough that no other company has ever done before. All people are asking for is implement the best practices from ChatGPT, Gemini, Claude, like the stuff we know and love. Even Grok has like nicely interfaced into X where like people say, hey Grok, is this real? And it just pulls it up for you. I find myself on tweets just going, oh yeah, like I don't want to copy this text out and into another LLM app. I'm happy just asking Grok real quick for an extra detail or one more fact. Google search overuse.
1:49John Coogan:is like there's been a lot of AI diffusion into products that's been good. Even Ramp, like Ramp has like chat interface where you can just say like, hey, how much did we actually spend on Amazon last month? And it'll just pull it up for you. And it's not like this revolutionary AIG. Well, here's the thing, here's the thing. It's just like, nice tool. I think they did a good job letting the hype build or the interest build organically, right? You rewind a year or two ago, they were running billboards for Apple intelligence, for Genmoji, all this stuff. So really setting themselves up for failure.
2:18John Coogan:stuff was overhyped and I think this and they were they were a part of oh they were yeah they were of course they were hyping it themselves of course of course they were like are we coded yeah but it seems like they have the right partnerships and and the right like product strategy at this point people are familiar with these tools so just putting them in different places seems reasonable models are good now so make them available at the click of a button ideally the Siri button which has been completely nerfed for the last two years actually more than that because Siri has never really seen the adoption or love, product love that many other products have seen.
2:52John Coogan:And users will be happy. So Google AI search overviews are a good example that prove that rolling out LLMs, it can be nerve wracking, but it's not rocket science. Like you spit the text out where people expect the answer. There will be funny viral hallucinations. Like right now, even with all the crazy Google IO news, amazing 3.5 foundation models like they're doing really good stuff deep minds really good great team like you still say disregard and instead of just giving you the definition it says like okay got it i won't i won't do that anymore and it gets confused so there will be those like viral jokey wow it failed if it flopped that's going to happen to apple and that's not what apple likes to deal with not at all but i don't think any of that will show up in the user metrics i think that you know churn and usage will be unaffected from the viral moment of like, oh, Apple, like the Apple, uh, tech summaries, they're hilarious and they often hallucinate and get things wrong.
3:51You still keep them on though?
3:53John Coogan:I left them on. I don't mind them. And I think a lot of times they're sort of useful and they're always delightful because they're funny because they're so like hallucinatory, but, uh, your PR team will have many heart attacks, uh, because you're not in the world of deterministic outputs anymore. So that's going to be a big cultural shift for Apple. I think in this non-deterministic, stochastic AI era. But I think that they can get through it just by running best practices that have been established for a year or two years in the rest of the AI world. The other big questions that everyone's asking around open ecosystems.
4:24John Coogan:So will Apple lean into the open claw Mac mini boom at all? That would be interesting to see, say, you know, in the next version of the software that goes on the Mac mini, hey, we're going to embrace open claw, We're going to embrace AI agents. We're going to do things that make those tools more effective in our ecosystem. You already know and love the hardware. You're buying it nonstop. It's out of stock. But we could do more to lean into that community. Or we could do less. We could say, hey, we're going to shut it down. We're worried about privacy. These are the two tensions that they're going to have to deal with.
4:56John Coogan:Will there be a pivot around vibe coding apps in the iOS app store? You asked John Gruber from Daring Fireball this when he joined the show on May 29th. Fantastic interview. Had a ton of fun with the Gruber. But it's a big question. And it's something that Apple is, they don't really have to respond yet. They're pretty quiet when things happen. They usually go and solve the problem. Oh, they really don't want to talk about it. Yeah, but eventually they start. Like, they didn't want to talk about climate change, but then they did a bunch of things to get to like net zero and eco-friendly buildings and solar panels on the roof and stuff.
5:32John Coogan:And then once they did, they were really noisy about it because they were like, we are carbon neutral, or we will be by a certain date. And I think once they figure out how to make money on it, then they'll start. Which they should. Which, yeah, I fully, I will say, I fully support. Exactly. Will native iOS apps from other AI labs have more access to iPhone functionality? What's the pathway for ChatGPT interfacing, Claude, Gemini? If you're using those apps, how many hooks are there? Will they be able to siphon in your text messages? If you click, yeah, I want to share my text messages, my iMessage with my app of choice, or will you need to say yes every single time, which will be a huge burden to having that integration happen.
6:15John Coogan:There's a lot of social media apps that say, hey, we want access to your whole camera roll, all of it forever. And that's somewhat intimidating. You get a number of different options. You can say, I want a temporary access, just take this photo, you can't see my whole library. Now people trust, many people, and maybe they just don't know, but they feel like they trust a lot of these maps. So they just say, yeah, yeah, take the whole camera roll. Sort of a crazy thing to do that they can just download your entire camera roll if you press that button, but people have. And so what will the AI version of that be?
6:48John Coogan:And how deep will it be? And how much will it build on top of the Siri app intense functionality versus other APIs that are deeper in the iOS ecosystem? There's one last thing, which is, we talked about how Apple doesn't want to address eco stuff until it's like, okay, we got it solved. And I'm wondering if in the coming years, there's going to be pressure for some sort of response on the whole, like phones are reducing the fertility rate stats. Because I don't know if you saw, but there was another research paper that was posted, and Derek Thompson basically zoomed out and said that I wasn't convinced, and now he is convinced that it's like up to 30 % of the reason for the recent decline below two.
7:32John Coogan:And I don't know where you sit on it. Below the replacement rate? Below the replacement rate. Not good if you're a fan of humanity and having a high population. But that is something that you could see bubbling up to being something that big tech companies, social media companies, device manufacturers have to answer to when they're in like free form podcasts, basically. But you know that these companies are not going to want to address that. As opposed to the AI CEOs that are like, oh, you want to talk about killing everyone? Absolutely. I'd love to talk about that for an hour. The PM of Denmark or what country was saying it's time to return.
8:07I'd rather my kids smoke.
8:08John Coogan:No, she specifically said, I would rather let my kids smoke cigarettes than use an iPhone, which is crazy. But I don't know. Maybe there's something there. Maybe the cure for cancer is right around the corner, but the cure for brain rot is not. It's possible. Yeah, and it's such a different debate because clearly a single drag on a heater is no good, right? You're ingesting poison. Yeah, burning ash. A single look at a screen, right, is not what is reducing the fertility rate. So anyways. It's interesting. Anyway, let's go to some reactions from WWDC. But first I'm going to tell you about Console.
8:46John Coogan:Console builds AI agents that automate 70 % of IT, HR, and finance support, giving employees instant resolution for access requests and password resets. iPhone. Yeah. I'm going to update your software tonight while you sleep. Next morning, iPhone says, I couldn't do it, bro. Just didn't feel right. Vibe was off. This is something that I didn't know was so common, but I think everyone's been in this position, which is like a funny thing. I think it has to do with how much the battery is charged, but lots of low-hanging fruit, hopefully resolved in WWDC. I did see a whole bunch of stats about just little performance gains, 30 % faster opening of the lock screen, 30 % faster on opening this app, and just little optimizations that I think will go a lot further.
9:31John Coogan:When we talk to Mark Gurman, he talks about how the AI features are too abstract. People want battery life, cameras, beautiful screens, fast. They want the basics most of the time. And so I think this is time to chop wood. It would be funny if they effectively threw up a model card and they're comparing. It's like, it's actually 2%. The Bento box is the original model card. It's 2 % better on. That's sort of what they do. You know the Bento box, right? The Bento box with like how many cameras, megapixels, flops, and how powerful the GPU is, how many cores are over here, how much storage it has.
10:07John Coogan:That graphic is their model card. We were riffing on this earlier. like when a product ceases to be sold on brand and is instead sold on performance, that's usually margin compression. Usually margin compression, like you comp it to cars. Like if you're purely buying on like range and price and speed and horsepower and seating arrangements, that feels much more commoditized than you got to have a Ferrari because it's a Ferrari. Don't ask about the specs. And I think for the Luce, this is the first time that people were talking about like, oh, zero to 60 and 2.5 for that price isn't actually that good.
10:43John Coogan:It's like, that's not the conversation you should be having about Ferrari. You should just be like, it's a Ferrari. Next question. Like, do you want one or not? Hilarious post from Sam Henry Gold here, of course, in jest, but they put up a Apple press release in the newsroom. Apple announces the death of Mark Gurman. It is done. It is done. Apple today announced the completion of Operation One More thing a multi-year initiative to permanently end the unauthorized disclosure of Apple's pre-release product information by Bloomberg intelligence reporter Mark Gurman. Gurman who had for 16 consecutive years obtained and published accurate details about Apple's products before their announcement has been neutralized.
11:20John Coogan:Operation one more thing was completed on schedule on budget and without complication. They're not that aggressive towards Mark Gurman but he is probably a thorn in their side and here he is he has a live blog up live blog for WWDC go check it out at Bloomberg.com. Eric Sufert is leaning in. Why is he leaning in? Because Mark Gurman says something about WDBC. He says, in addition to the focus on AI, Siri, and major quality and performance improvements across the operating systems, I'd expect two other focal points today, privacy and safety features. I imagine Sufert is leaning in because privacy, safety features, not great for ad monetization.
11:57John Coogan:Usually you're hiding more information. Tyler, what's been your reaction generally take me through whatever yes i've been watching uh the last stream it's still going on so there's they're still releasing stuff but i would say just on that point they've been like every single time or have you been studying i was studying like everything every time they talk about a new feature with ai they always say like this is on a private cloud this is like not public this is like extremely secure so they're really pushing on that point i think what does private cloud mean i don't know they're talking about like their own foundation models i think so they're trying to emphasize that.
12:29They said the word Gemini. I don't know if they said it, but it was on screen.
12:34John Coogan:So it seems like they have the ability with their deal with Gemini to basically white label, fine tune, mid train, do whatever they need to, and then resell that with their own branding. That's great deal. My question is like, who's inferencing that? There's a billion iPhone users. And if they're all pushing the Siri button all day long, and they're anywhere near the frontier, that's a significant amount of inference. Has Apple built some sort of secret data center that can serve that? Are they saying private cloud and really it's like a corner of GCP? Is it a bunch of Mac minis wired together?
13:10John Coogan:Like what did they do to actually build that private cloud? Because even if they did it, even if they did it and didn't show up in the CapEx numbers, didn't show up in any of the SEC filings, like it would show up in the emissions data and the ESG numbers because unless they have some crazy solar nuclear-powered facility, where's that inference coming from? I imagine some of it can be done on device. That's exciting. Yeah, Jonah says on device. Can it all be done on device? Tyler. I don't know. Groxon says they brought up rate limits and a subscription plan. Huh. Did you see that? Yeah. I'll look for that.
13:48John Coogan:I mean, you don't have rate limits or subscription plan if it's on device because why would you? and then also you would never say private cloud if you're doing it on device you would just say it's on device of course it's private so private cloud cloud means not on device it's in the cloud and so i obviously apple has a lot of data centers they have a lot of cloud capacity across their productivity suite where are the where are the photos stored in ifotos like obviously those are stored in the cloud they have a lot of storage like everyone gets two terabytes when they get a phone. So they clearly have a lot of data center capacity, and they've done a lot to make that ESG compliant, but I'm very curious about where that goes over time.
14:29John Coogan:Anyway, we should move on to the news from Friday. The stocks are already back up, but first I'm going to tell you about CrowdStrike. Your business is AI. Their business is securing it. CrowdStrike secures AI and stops breaches. One more thing. Oh, sure. One more thing, eh? One more thing. We got one more take from Jordi about Apple. Jane says Apple concedes on liquid glass design compromising for usability and shares a couple screenshots here. And so. Wait, so they're going deeper in liquid glass or pulling back? Pulling back. I saw the new Apple Maps icon and it looked pretty good. It had a little feature of liquid glass in there.
15:10John Coogan:I thought it looked cool. I did hear people complaining about the new Mac operating system being like too bright or too dark or something. like some contrast issue. I haven't noticed it, but it was something I saw people complaining about. Anyway, Friday was a big day in the market. We were off, but the news kept moving. So we're covering it today. The Labor Department reported that the U.S. added a seasonally adjusted 172 ,000 jobs and that the unemployment rate remained unchanged at 4.3%. So on the cover of the Wall Street Journal, U.S. hiring gathers steam, third straight monthly increase, slight decrease from the previous month, which was slight down from the previous month, but still in adding territory in the hundreds of thousands.
15:52John Coogan:So the bubble popped. The bubble popped. Friday was the worst day for the NASDAQ in more than a year, 4.2 % down. It's over. But good news is that today we're back. We're up 1.5 % now. It's officially 2003. People ask what year it is. Re-inflating. No, no, it's not reinflating. We're building back. The bubble popped. It's 2003 now. It's not 99. It's not 2000. It's 2003. We're well past the bubble popping. Got it. Right. So, but actually, quick explanation of what happened. So, the US labor market is really picking up 172 ,000 seasonally adjusted jobs added in May. Third month in a row. Decent amount.
16:30A lot of healthcare stuff. For the World Cup.
16:32John Coogan:Yes. And a lot of travel and workers related to the World Cup stuff that's going on. Tourism. This is terrible news for all those black-pilled AI leaders that have been praying, manifesting job losses, despite their Herculean efforts. They can't get the unemployment rate to go up at all. It's crazy. They've been saying 10%, 20%, 50%, 100 % of all jobs are going away. Good luck. Yeah, you're going to have to work harder because the U.S. economy is undefeated and the American workers undefeated, as evidenced by this latest jobs report. No. The AI job apocalypse is canceled at least for the month of May.
17:10John Coogan:We will see where things go, of course, of course. But it is good news. We want hiring. We want jobs to be abundant in our society. And so in general, it's good news. I believe the jobs report. I don't think the numbers are going to be massively revised down. I think that they're generally accurate and track with the ADP numbers and a lot of other numbers. So I think the jobs are really being added. They're not in all the most critical industries. There's a lot of nuance there. How long will it go on? But in general, the economy is healthy. But inflation is rising. The closing of the Strait of Hormuz has spiked the cost of gas and overall prices have been increasing more quickly than the Fed would like.
17:49John Coogan:For some time, even before the Strait of Hormuz, inflation was running a little hot. Yeah, well above the 2 % target for basically as long as I've been an adult. Yeah. And so this makes the likelihood of a rate cut more unlikely. In fact, it looks like we might be in rate hike territory soon, which is, of course, not good for tech companies that have earning forecasts that stretch out into the next decade. So the silver lining in high rates, if you want some copium, is that at least the Fed has something useful in the tool chest in case the economy does slow down. You know, like we're running hot.
18:24John Coogan:We have high rates. At least there's room to cut to 3%, 2%, 1%, zero. If the market's selling off, if the unemployment rate's going up, you have something in the tank. Whereas during COVID, like the rates were already so low. There was a lot of unemployment all of a sudden, and it was just like stimulus, spend a bunch of money, mail everyone a check. There wasn't that much that the Fed could do. There was a time that we couldn't imagine this level of speculation in the markets at something like where rates are right now, right? People that were sort of born in the Zurb era with all the speculation right now is by itself an argument to raise rates even further.
19:08John Coogan:Totally. Well, yeah, once the rates spiked off of like that 3 % jump, like the end of Zerp, it was like, OK, like there will never be froth again, certainly. Certainly like tech stocks will never see meteorite rises. A friend of mine, Blake, made bumper stickers that just said, please, God, just one more bubble. And God delivered. OK, so the other story, VC horror stories. This was kicked off by Greg Eisenberg. I didn't realize that he was the one that started this whole thing and kicked the hornet's nest and everyone came out of the woodwork with their VC horror stories. He said he had a big discussion about founders' bad experience with venture capital and a number of high-profile firms' VCs caught strays.
19:49John Coogan:Mercor CEO Brendan Foody detailed what he calls the Sequoia scam, which is something interesting we should actually dig into. Cloudflare CEO Matthew Prince accused Vinod Khosla of offering to invest in his Series C only if he would fire a few of the people at the pitch meeting who had just left the room momentarily to go to the bathroom. See, there was a separate. So Greg Eisenberg, I was really crossing wires here because Greg Eisenberg is the one who says, he says, I was once pitching in a boardroom at a top three VC firm for a$15 million Series A. That's pretty easy to narrow down. But anyway, he says 12 people in the meeting.
20:27One of the GPs fully fell asleep because some of the top, you know, FF doesn't have 12 GPs.
20:33John Coogan:They don't really do partner meetings like this for$15 million Series A. So even if you put them in the top three, you can't catch a stray here. Anyway, one of the GPs fully fell asleep, out cold for 30 plus minutes. Nobody acknowledged it. Everyone kept going. Then separately, Matthew Prince. Okay, founder or an operator falls asleep in the office because they're so tired because they're grinding so hard and they're a hero. Yeah, this is what Paki said. When Elon falls asleep in the factory, it's no big deal. But when a VC falls asleep, it's the end of the world. We're aware of some static in the ultradome.
21:10John Coogan:Yeah, I think we got a new mic line, but I'll try not to touch it and we'll see what happens. So there's lots of chatter about the VC horror stories. certainly a discussion worth having. You know, you got to keep them in check. But Silicon Valley has always been so high growth and positive sum that relatively good behavior is usually the equilibrium. It's pretty rare that you get a really bad VC. Because even when a startup fails, investors can't write off the founder entirely because they might start the next generational company. And so they might wind up giving on a non-VC friendly sort of acquihire because they're like, or like help them land a paycheck somewhere, get a job, serve as a good reference, maybe even fund the next product in the next company, because they're just like, this is an iterated game and we don't want to have you on our bad side forever.
22:02John Coogan:Now that doesn't mean they can't pass. And so there's basically this wide gap that I'm seeing in these discussions where there's VC pitch horror stories and then VC board horror stories. And I have much less sympathy for the former. Like I don't really care about VC pitch horror stories all that much because you can just pass. Because a lot of founders will have 50 meetings for financing. You would expect at least a couple to just be terrible, right? The person didn't know who you were, didn't read the materials ahead of time, was rude. And you might want that person. didn't show up. You might want a checked out VC who's just going to let you cook.
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22:42John Coogan:And they're like, yeah, I see this purely financially. My team crunched the numbers. I'm in. But like, don't count on me to value add. Like, I'm not going to be in the weeds with you every day. And then there's a different VC who's like, I'm going to be in the office. I'm going to be your back office. The best VCs will not even tell you, oh, I'm going to be grinding for you every day. I'm going to be helping you get all your key hires. They'll just be accurate. Yeah, they'll I'll just tell you, one of my favorite VCs in the world just says like, I give you money and then I will help you raise more money.
23:10And that's the only thing I'm going to do. And that's fine. And I'm going to be your friend. We'll get dinner now and then. But that's what you can expect from me. And that's exactly what he gives founders. And so everyone is like, this guy's great.
23:21John Coogan:Yeah. And then there's other firms that say, we'll help you with go to market. And they will. There's other people that say, we will help you with marketing. And they don't. And you just want to be transparent and accurate there. And so, like, as a founder, your job is to sell equity from time to time. Your job is to find buyers for that equity. Some companies actually only do that. It's true. They don't actually get it. Stock is the product occasionally. So your job is to find investors who want to purchase that equity with cash, VCs. You need to reference, check them beforehand, make sure they're fed, think through their competitive investments, keep them entertained and awake during the pitch.
23:55John Coogan:VCs shouldn't be disrespectful. Like, literally falling asleep is. but this is far from the worst thing that regularly happens in the course of growing a business. We pitched for Figma's seed round in 2013. Most folks didn't get it but everyone I met was super nice to me. Yeah, it's so funny when you compare VCs to the other, like I said, the other kinds of calls you have. VCs are probably like generally way nicer, right? Like a customer is less likely to like be overly friendly if they're not interested in what you're selling, right? They're like, yeah, this doesn't really seem like a fit. Brendan from Mercore, former guest and friend of the show, has a bone to pick with everyone.
24:40He's coming after YC. He's coming after Sequoia. He says, in the last six months, I've seen half a dozen rounds where Sequoia invests in two tranches. Everyone pretends they only did the higher valuation. Founders misrepresent this to their employees and then shop it to angels too. Sequoia's blended price is blatantly deceptive, less than 50 % of the one projected to the market.
25:01John Coogan:So they'll invest at half a billion and a billion, two tranches, and then the founder will go out and say we raised$100 million at a billion when really Sequoia got in at the blended price, right? Now, that's not illegal. There's nothing wrong with that. And that can make sense for both sides for a variety of reasons. You don't want to misrepresent that, though. If you go and misrepresent that to another investor and you don't tell them the actual structure of the deal, that can be securities fraud. So that is a major risk. But that's not on the VC. Like the VC should not go to another investor and say, oh, yeah, we just did the full deal at a billion.
25:38John Coogan:They should give that context. But that doesn't seem like a unique thing. This is like classic, like all the crossover funds were doing this. Tons of funds have done this. I mean, also, this isn't some secret. You go back to the original Sequoia YouTube investment memo, and it's tranched and structured. They've been doing this for 25 years, and it's just like nobody read the manual or something. Because if you actually study in no ball, you would know that structured investments exist. At the same time, I don't put it on every employee who's getting stock options and thinking about the heat on a company and every journalist to understand that structure.
26:15John Coogan:So there is an impetus and a responsibility. Yeah, very aggressive and unnecessary to call this a quote Sequoia scam. Because Brendan also replied to his own tweet saying just 30 minutes ago after the post had gone viral. In fairness to Sequoia, this is common practice in the industry across all top firms. Three likes on that one. 1 ,000 likes on the other one. Brutal. Brutal. Travis Kalanick said in 2001, I intercepted a partner at a VC who was trying to escape his office before our meeting was supposed to start. I ended up pitching him in his parked Lexus from the passenger seat. At one point, he grabbed my laptop, placed it on his large belly, which was pressed against the steering wheel, and rapidly flipped through the slides himself.
26:56John Coogan:2001 fundraising hit different. I want to know how the story ended. Did he invest or not? Did he pull out his checkbook? Because maybe he was like, you got me, Travis. We actually had a plan to test this theory. Tyler, do you want to take us through it? Yeah, well, so I was just looking at this. I found a study. basically it was they took a bunch of older men 66 to 83 they put them in a room where it was kind of a slightly dim room there's not a lot of simulation going on they just sat in there they read them cloud flares as once and they basically tested to see how long would it take them to fall asleep and so the median was 36.9 minutes and here's the thing a pitch Usually an hour.
27:40Well, sometimes, I mean, if it's an early pitch, early conversation, maybe it's 30 minutes. Maybe. If it's going well, it starts to drift over. Yeah. But that's the danger zone.
27:47John Coogan:Danger zone. So this is the lesson. This is the lesson for founders. If you have a boring business, if you have a boring business and you're pitching a VC who's an older gentleman, you got to keep the pitch meeting to less than 30 minutes. You got to bring the air horn. especially i think in that story it also said the older gentleman was in a herman miller chair which we know are quite comfortable those are quite popular in silicon valley too compounds the fact okay yeah i mean that's an elite sleep spot for a nap that's an elite spot the chair was arguably designed for office naps yeah no one's getting like real work done i think so i think so so uh yeah i i this one's tough because it's easy to just jump right um in matthew Prince's camp.
28:32John Coogan:Oh, I'm in Vinod Kostla's camp. Also, Vinod didn't fall asleep, so it's all moot. But we know the secret. It's the air horn. Bring the air horn. No one's falling asleep. Problem solved. Tyler had a good story when they were building Divi. They pitched Rajiv Misra in the SoftBank Redwood City HQ. And then Masa and Tokyo soon after, it was absolute cinema. Poppin' zins, smoking a vape, loud coughing to throw us off. Wait, what? Intentional coughing? Assistance whispering in Rajiv's ear. That's a power play. That's a power move. You got to respect that for sure. See, that's a post-singularity job right there.
29:15John Coogan:Yeah, for sure. Come in, whisper into the person's ear. It's good. Yeah. Some of the most fascinating questions ever asked in Tokyo. Masa starts the meeting with, you have 10 minutes. We flew like 20 hours. See, that's just a great way to get to the - You just got a power play, Tyler. Sorry, buddy. I think that's just a great way to get, really get to the meat. I think so. I think so. Thank you for tuning in. Thank you for watching TVPN today. We'll see you tomorrow at 11 a.m. sharp. Give us five stars. It's been an honor. We love you guys. Sign up for a newsletter, TVPN.com. Goodbye.
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