WWDC Kicks Off, Jobs Up, Tech Down, VC Horror Stories Go Viral | Diet TBPN

Summary

TBPN Podcast Episode Summary
Episode: “WWDC Kicks Off, Jobs Up, Tech Down, VC Horror Stories Go Viral | Diet TBPN”
Date: June 8, 2026
Hosts: John Coogan & Jordi Hays
Special Guest/Commentators: Tyler

---

Episode Overview

This fast-paced “Diet TBPN” episode unpacks Apple’s big moves at WWDC 2026, the latest jobs report and what it signals for tech, and a wave of viral venture capital (VC) horror stories sweeping social media. The hosts mix sharp analysis and irreverent commentary, covering what Apple’s “All Systems Glow” theme actually means, the hype and realities of Apple’s approach to AI, economic signals from a hot U.S. labor market, and frank founder stories revealing VC culture behind closed doors.

---

WWDC 2026: Apple's AI Era & “All Systems Glow”

[00:03 - 15:03]

Key Discussion Points

• WWDC as a Software Event: The episode kicks off with an emphasis that WWDC is about software, not hardware—this year, centering on “Apple Intelligence,” new Siri capabilities, and system-wide AI integration.
• Apple’s AI Adoption: The team reflects on Apple’s more measured approach—delivering solid, well-integrated AI features rather than “never-seen-before” breakthroughs.
• Raised but Realistic Expectations: While previous years were hyped, hosts say Apple appropriately let anticipation grow organically this year.

  “They did a good job letting the hype build or the interest build organically... They were really setting themselves up for that.” – Host [02:04]

• Siri’s Makeover & the ‘Stochastic AI Era’: Apple’s challenge is adapting to the unpredictable nature of large language models (LLMs) in a user-experience-obsessed culture:

  “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.” – Tyler [03:53]

• Embracing Openness?: Big open questions persist—will Apple leverage the open-source community more (e.g., around “open claw Mac mini” and AI agents) or double down on privacy and control?

  “Will Apple lean into the open claw Mac mini boom at all?... Or we could do less. We can say, hey, we’re going to shut it down.” – Tyler [04:16]

• Privacy, Safety, and AI Integration: Apple’s “private cloud” narrative drew skepticism—what does it actually mean, and whose infrastructure is really powering it?

  “What does private cloud mean?... If it’s on device, you don’t need rate limits or a subscription plan.” – Tyler [12:22 & 13:44]

Memorable Moments & Quotes

• Siri Comedy:

  “IPhone, 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.” – Host [08:54]

• Specs Wars: Hosts riff on Apple’s “bento box” technical spec graphics as the new “model card”—when product value shifts to specs, it often signals margin pressure and commoditization.

  “When a product ceases to be sold on brand and is instead sold on performance, that’s usually margin compression.” – Tyler [10:00]

• Mark Gurman Satire:

  “Apple today announced the completion of Operation One More Thing, a multi year initiative to permanently end the unauthorized disclosure of Apple’s prerelease product information by Bloomberg Intelligence reporter Mark Gurman. Gurman... has been neutralized.” – Tyler, reading a joke post [11:00]

Timestamps

• 00:03 – WWDC framing, Apple Intelligence
• 02:04 – Reflecting on AI hype and product strategy
• 03:53 – LLM unpredictability, Apple’s cultural adjustment
• 04:16 – Open ecosystem vs. privacy tension
• 09:04 – Software performance improvements
• 10:00 – Apple as specs-driven vs. brand-driven company
• 11:00 – Satirical Mark Gurman “obituary”

---

Tech, Economy & Markets: Jobs Up, Tech Down

[15:03 - 19:35]

Key Discussion Points

• Labor Market Signals: The hot jobs report—172,000 jobs added, unemployment unmoved—contrasts with tech industry pessimism about AI-driven job losses.

  “The AI job apocalypse is canceled, at least for the month of May. The US economy is undefeated and the American worker is undefeated, as evidenced by this latest jobs report.” – Tyler [16:19]

• Market Volatility: Despite bullish labor data, Friday was “the worst day for the NASDAQ in more than a year.” The hosts joke the cycle has “reset to 2003.”
• Inflation & Fed Policy: With inflation above target, rate cuts are unlikely; rate hikes could follow—tough news for growth tech stocks.

  “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 not good for tech companies.” – Tyler [17:59]

Timestamps

• 15:03 – Market update: Jobs, NASDAQ drop, “back to 2003”
• 16:19 – Labor data and the myth of the “AI job apocalypse”
• 17:59 – Inflation, interest rates, and implications for tech

---

VC Horror Stories Go Viral: Inside Silicon Valley Pitch Rooms

[19:35 - End]

Key Discussion Points

• Viral Founders’ Stories: Recent social buzz spotlights infamous VC misbehavior—sleeping in pitch meetings, bizarre demands, and boardroom power plays.

  “One of the GP’s fully fell asleep—out cold for 3:30 plus minutes. Nobody acknowledged it. Everyone kept going.” – Quoting Greg Eisenberg [20:46] “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.” – Quoting Packy [20:58]

• Sequoia ‘Tranche’ Tactics: Criticism of Sequoia’s two-tranche investments gets labeled “the Sequoia scam,” fueling debate—but hosts note it’s industry standard.

  “Very aggressive and unnecessary to call this the, quote, Sequoia scam, because... this is common practice in the industry.” – Host [26:18]

• Pitch Room Realities: Humor & Advice:

  “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.” – Tyler [27:47]

• Power Moves & Legends: Power dynamics play out—Travis Kalanick’s story about pitching a partner in his car; Softbank pitch room stories involving coughing, vapes, and “10 minute” time limits.

Notable Quotes & Stories

• Classic Power Play:

  “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... and rapidly flipped through the slides himself.” – Quoting Travis Kalanick [26:31]

• Furniture as Strategy:

  “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.” [27:47] “The older gentleman was in a Herman Miller chair, which we know are quite comfortable.” – Guest [28:05] “That’s an elite sleep spot for a nap. The chair was arguably designed for office naps.” – Host [28:14]

Timestamps

• 19:35 – Greg Eisenberg’s viral VC story
• 20:58 – The “Elon can nap, VC can’t” double standard
• 25:01 – Sequoia “blended price” debate
• 26:31 – Founders’ war stories (Travis Kalanick, Softbank)
• 27:47 – Pitch meeting science (“danger zone”: 30-minute naps in comfy chairs)

---

Additional Highlights

• Mainstream Tech Self-Examination: Brief but sharp references to broader cultural debates—like technology’s impact on fertility, and extreme reactions from world leaders.

  “She specifically said, I would rather let my kids smoke cigarettes than use an iPhone. Which is crazy.” – Host [08:07]

---

In Short

• Apple’s WWDC centers on AI and privacy, with pragmatic rollouts—not moonshots—raising the bar for system-wide integration.
• Spec-wars and market forces point to a brand-versus-performance identity crisis for Apple and tech at large.
• Strong labor market data and persistently high inflation reshape expectations for tech’s economic environment.
• Viral ‘VC horror stories’ reveal Silicon Valley’s underbelly, but the hosts argue most founder-VC interactions are pragmatic and generally positive.

---

Episode Standout Quote:

“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.” – Tyler [03:53]

---

For more, catch the episode in full on Spotify or tap into their newsletter for future show rundowns.

Transcript

[Tyler]

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 WWC already. We have a bunch of folks calling in to discuss WWC 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. All Systems Glow.

[Host]

Interesting.

[Tyler]

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. 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. 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 stock stuff we know and love. Even Grok has like nicely interfaced into X where like people say, hey, Grok, is this real? And 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. 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. Well, here's the thing. I think it's. I think they did a nice tool.

[Host]

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 gen emoji, all this stuff. So really setting themselves up for that

[Tyler]

stuff was overhyped and I think this.

[Host]

And they were, they were a part of. They were, they were. Of course they were hyping it themselves. Of course, of course they were like, are we goated?

[Tyler]

Yeah. But it seems like they have the right partnerships and the right 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 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 5.3.5 foundation models, like they're doing really good stuff. DeepMind's 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. It flopped. That's going to happen to Apple and that's not what Apple likes to deal with.

[Host]

Not at all.

[Tyler]

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 tech summaries. They're hilarious and they often hallucinate and get things wrong.

[Host]

You still keep them on.

[Tyler]

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 hallucinatory. But your PR team will have many heart attacks 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. So will Apple lean into the open claw Mac mini boom at all? That would be interesting to see. Say you know, in, 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 can 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. Will there be a pivot around Vibe coding apps in the iOS app store? You asked Jon Gruber from Daring Fireball this when he joined the show on May 29th. Fantastic interview. Had a ton of fun with the Gruber data. 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.

[Host]

Oh, they really don't want to talk about it.

[Tyler]

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. 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.

[Host]

And I think once they figure out how to make money on it. Yeah, then they'll start.

[Tyler]

They should.

[Host]

Which, which, yeah, I fully. I will say I fully support.

[Tyler]

Exactly. Will native iOS apps from other AI labs have more access to iPhone functionality? What's the pathway? 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? 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 temporary access. Just take this photo. You can't see my whole library. Now. People trust many people. 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, what will the AI version of that be and how deep will it be and how much will it build on top of the Siri algorithm app intense functionality versus other APIs that are deeper in the iOS ecosystem. There's one last thing, which is, I mean, 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 2. And I don't know where you sit on.

[Host]

Below the replacement rate.

[Tyler]

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 freeform podcasts, basically. But you know that these companies are not going to want to address as opposed to the AI CEOs. They're like, oh, you want to talk about killing everyone? Absolutely.

[Host]

I'd love to talk about that for an hour. The PM of Denmark or what country was saying, yeah, it's time to return. I'd rather.

[Tyler]

No, she specifically said, I would I 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.

[Guest]

Yeah.

[Host]

And it's such a different debate because clearly a single drag on a heater is no good. Right? You're ingesting poison.

[Tyler]

Yeah.

[Host]

Burning out a single look at a screen. Right. Is not what is, you know, reducing the fertility rate. So anyways, it's interesting.

[Tyler]

Anyway, let's go to some reactions from wwdc. But first I'm going to tell you about console. Console builds AI agents that automate 70% of it. HR and finance support giving employees instant resolution for access requests and password resets.

[Host]

IPhone, 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.

[Tyler]

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 wwc. 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. When we talk to Mark Gurman he talks about how the AI features are too abstract. People want battery life, cameras beautiful screens, fast like they want the basics most of the time. And so I think this is time to chop away.

[Host]

It would be funny if they, they effectively threw up a model card and they're comparing.

[Tyler]

It's like they actually the bento box

[Host]

is the original model card, 2% better on.

[Tyler]

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 stor it has like 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. Then you got to have a Ferrari because it's a Ferrari. Don't ask about the specs. And I think for, for the lucha, this is the first time that people were talking about like oh, 0 to 60 and 2.5 for that price isn't actually that. 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 ingest. But they put up a Apple press release in the newsroom. Apple announces the death of Mark Gurman.

[Host]

It is done.

[Tyler]

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 prerelease 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. 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 on their side. And here he Is he has a live blog up? Live blog for WWDC. Go check it [e-mail] Eric Soofer is leaning in. Why is he leaning in? Because Mark Gurman says something about wwc 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 Suefert is leaning in because privacy safety features not great for ad monetization. Usually you're hiding more information. Tyler, what's been your reaction? Generally take me through whatever.

[Guest]

I've been watching the live stream, it's still going on. So they're still releasing stuff but I would say just on that point they've been like have you been watching or

[Tyler]

have you been studying?

[Guest]

I was studying. Every time they talk about a new feature with AI, they always say this is on a private cloud. This is not public, this is extremely secure. So they're really pushing on that point, I think.

[Tyler]

What does private cloud mean?

[Host]

I don't know.

[Guest]

They're talking about their own foundation models, I think. So they're trying to emphasize that they

[Host]

said the word Gemini.

[Guest]

I don't know if they said it, but it was on screen.

[Tyler]

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 a great deal. My question is 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? 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 the, in the, any of the SEC filings, like it would show up in the emissions data and the, 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 devices. That's exciting.

[Host]

Jonah says on device.

[Tyler]

Can it all be done on device, Tyler? I don't know.

[Host]

Groxen says rate limits and a subscription plan.

[Tyler]

Huh. Did you see that? Yeah, I'll look for that. 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 obviously Apple has a lot of data centers. They have a lot of cloud capacity across their productivity suite. Where are the photos stored in iphotos? 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. 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.

[Host]

So one more thing.

[Tyler]

Oh, sure. Apparently one more thing, eh?

[Host]

One more thing.

[Tyler]

We got one more take from Jordy about Apple.

[Host]

Jane says Apple concedes on Liquid Glass design, compromising for usability and shares A couple screenshots here.

[Tyler]

And so wait, so they're going deeper in liquid glass or pulling back?

[Host]

Pulling back.

[Tyler]

I saw the new Apple Maps icon and it looked pretty good. It had a little feature of Liquid Glass in there. I thought it looked cool. I did hear people complaining about the new Mac operating system being like too, 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 COVID of the Wall Street Journal, U.S. hiring gather 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. 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 re inflating. 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.

[Host]

Got it.

[Tyler]

Right. So, but actually, quick explanation, what happened. So the U.S. labor market is really picking up. 172,000 seasonally adjusted jobs added in May 3rd month in a row. Decent amount. A lot of healthcare for the World Cup. Yes. And a lot of travel and, 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 gonna have to work harder. Because the US economy is undefeated and the American worker is undefeated, as evidenced by this latest jobs report. The AI job apocalypse is canceled, at least for the month of May. 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 straight for Hormuz has spiked, the cost of gas and overall prices have been increasing more quickly than the Fed would like for some time. Even before the Strait of Hormuz, inflation was running a little hot.

[Host]

Yeah. Well above the 2% target.

[Tyler]

Yes.

[Host]

For basically as long as I've been an adult.

[Tyler]

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. We have high rates. At least there's room to cut to 3%, 2%, 1%, 0 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, you know, mail everyone a check. There wasn't that much that the Fed could dip.

[Host]

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.

[Tyler]

Totally. Well, yeah. Once the rates spiked off of that 3% jump, like the end of ZIRP, it was like, okay, there will never be froth again. Certainly, certainly tech stocks will never. A friend of mine rise.

[Host]

A friend of mine, Blake made bumper stickers that just said, please God, just

[Tyler]

one more bubble and God delivered. Okay, so the other story, VC horror stories. This, this was kicked off by Greg Eisenberg. I didn't realize that he was the one that started this whole thing. He 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. Mercour 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, one of the GPS fully fell asleep because some of the top, you know, FF doesn't have 12 GPS. They don't really do partner meetings like this. So for $15 million Series A. So even if you put them in the top three, you got. Can't catch a string here. Anyway, one of the GPS fully fell asleep, out cold for 3:30 plus minutes. Nobody acknowledged it. Everyone kept going. Then separately, Matthew Prince, okay, founder or

[Host]

an operator, falls asleep in the office because they're so tired, because they're grinding so hard and they're a hero.

[Tyler]

Yeah, this is what Packy 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.

[Host]

We're aware of some static in the ultradam.

[Tyler]

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, 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 aqua hire because they're like, and help, 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. Now that doesn't mean don't like they can't pass. And so there's basically this wide gap that I'm seeing in these discussions where, 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.

[Host]

Yeah, because a lot of founders will have 50 meetings for financing. You would expect at least a couple to just be terrible.

[Tyler]

Right.

[Host]

The person didn't know who you were, didn't read the materials ahead of time, was rude.

[Tyler]

And you might want that person show up. You might want a checked out VC who's just going to let you cook. And they're like, yeah, I see this purely financially. My, my, 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, there's a different VC who's like, I'm going to be in the office, I'm going to

[Host]

be your 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.

[Tyler]

They'll just be accurate.

[Host]

They'll, they'll just tell you one of my favorite VCs in the world just Says, like, I give you money.

[Tyler]

Yep.

[Host]

And then I will help you raise more money.

[Tyler]

Yep.

[Host]

And that's the only thing I'm going to do.

[Tyler]

And that's fine.

[Host]

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.

[Tyler]

Yeah. And then there's other. 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's to find buyers for that equity. And that's.

[Host]

Some companies actually only do that.

[Tyler]

That's true. The 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. 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.

[Host]

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, when you compare. When you compare VCs to the other. Like I said, the other kinds of calls you have.

[Tyler]

Yeah.

[Host]

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, like, doesn't really seem like a, you know, doesn't really seem like a fit.

[Tyler]

Yeah.

[Host]

Brandon from her core, former guest and friend of the show is, has a bone to pick with everyone. Yeah, he's coming after yc. He's coming after Sequoia.

[Tyler]

Yes.

[Host]

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 1 projected to the market.

[Tyler]

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. They should give that context. But that doesn't seem like it's on

[Host]

the founder in the same way.

[Tyler]

This is, like, classic. Like, all the crossover funds were doing this. Tons of funds have done this. This. I mean, also, this isn't some secret. Like, you go back to the original Sequoia YouTube investment memo, and it's tranched and structured. Like, they've been doing this for 25 years. And it's just like, nobody read. Nobody read the manual or something, because, like, if you actually study and no ball, like, 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. So there is. There is an impetus and a responsibility.

[Host]

Yeah. Very aggressive and unnecessary to call this the, 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.

[Tyler]

Three likes on that one, 1000, brutal on the other one, brutal. Travis Kalanick said, In 2001, I intercepted a partner at a VC 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. 2001 fundraising hit different.

[Host]

I want to know how the story ended.

[Tyler]

Did he invest or not?

[Host]

Did he pull out his checkbook?

[Tyler]

Because maybe he was like, you got me, Travis. You know, we actually had a plan to test this theory. Tyler, do you want to take us through it? Yeah.

[Guest]

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.

[Tyler]

This is actually.

[Guest]

They put them in a room where it was Kind of a slightly dim room. There's not a lot of, like, a

[Tyler]

lot of VC offices. They're very shady.

[Guest]

And they just sat there and they

[Host]

read them Cloudflare's S1, and they basically

[Guest]

tested to see how long would it take them to fall asleep. And so the median was 36.9 minutes.

[Tyler]

I feel like. Okay, so.

[Guest]

So if you.

[Host]

And here's the thing. A pitch. A pitch.

[Tyler]

Usually an hour.

[Host]

Well, 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, that's the danger zone.

[Tyler]

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

[Guest]

in that story. It also said the older gentleman was in a Herman Miller chair, which we know are quite comfortable.

[Tyler]

Those are quite popular in Silicon Valley, too.

[Guest]

Compounds the fact.

[Tyler]

Okay, yeah.

[Host]

I mean, that's an elite sleep spot for a nap.

[Tyler]

That's an elite spot for a nap.

[Host]

The chair was arguably designed for office naps. No one's getting, like, real work done

[Tyler]

in a Herman Miller. I think so. So, yeah, this one's tough because it's easy to just jump. Right. I'm in Matthew Prince's camp. I'm in Vinod Khosla'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 fallen asleep. Problem solved.

[Host]

Tyler had a good story. When they were building Divi, they pitched Rajiv Mistra in the softbank Redwood City hq and then Masa in Tokyo soon after. It was absolute cinema. Popping zins, smoking a vape, loud coughing to throw us off.

[Tyler]

Wait, why? Intentional coughing.

[Host]

Insistence. Whispering in Rajeev's ear.

[Tyler]

That's a power.

[Host]

That's a power move.

[Tyler]

You gotta respect that for sure.

[Host]

See, that's a post singularity job there, for sure.

[Tyler]

Come in. Whisper into the person's ear. It's good.

[Host]

Yep.

[Tyler]

Some of the most asinine questions ever asked in Tokyo. Masa starts the meeting with. You have 10 minutes. We flew, like, 20 hours.

[Host]

See, that's just a great way to get.

[Tyler]

He's got power play. Tyler. Sorry, buddy. You think that's. I think you just.

[Host]

I think that's just a great way to get. Really get to the meat right quickly?

[Tyler]

I think so. Thank you for tuning in. Thank you for watching TVPN today. We'll see you tomorrow at 11am sharp. Give us five stars. Spotify. Sign up for newsletter CBPN.com goodbye.