Shaan is buying Google stock while recording, triggered by the backlash around Google’s Gemini AI chatbot. Sam investigates whether Pelosi stock trades actually move the market, which they do. The episode covers the philosophy of individual stock trading, whether to follow Pelosi’s trades, the Harbor baby monitor product, and an interesting deep dive on Penske Media Corporation — the under-the-radar media empire that owns Rolling Stone, Variety, the Hollywood Reporter, South by Southwest, and dozens more.
Speakers: Sam Parr (host), Shaan Puri (host)
Pelosi’s Trade Moves the Market [00:00:00]
Sam: All right, you ready to do this?
Shaan: Hold on, I’m just executing a stock trade right now. I am The Wolf of Wall Street right now, Sam. I’m not here talking to you — I’m on the stock market floor shaking my money maker. Take my money.
Sam: I don’t think The Wolf of Wall Street used Robinhood, but that’s okay. Here’s what we’re going to do: if you want to find out how to lose money like I do, stick around.
Shaan: All right, so what is it? You’ve been on a stock kick, which is just bad news for me. Anytime I get on a stock kick, bad things happen. I don’t realize till three years later.
Shaan: Let me show you these two charts. First: Palo Alto Networks. I’m guessing you’re not following them that closely?
Sam: I’m not following right now, but I know it’s one of the Silicon Valley OGs, been around a long time.
Shaan: Good enough. Look at the stock — last five days, down about 14-15%. Pretty bad. And look at today: up 10%. You might ask yourself — did they just have an earnings call? A new product? A big AI breakthrough? No. Our girlfriend of the pod, Nancy Pelosi, just made a trade. She just bought a million dollars’ worth of Palo Alto Networks stock. Immediately people start following her and buying blind, because they don’t know what she knows, but they know she knows something.
Sam: That’s so funny that’s what’s happening nowadays. I follow this account — the Pelosi tracker. It said: “Breaking. The queen is back at it again. She just bought $1.25 million of Palo Alto Networks calls.” And a sub-headline: “Palo Alto Networks is one of the leading cybersecurity companies in the nation.” In case you need to know. But here’s the reality — you don’t need to know. You just need to know Nancy Pelosi bought it.
Shaan: Are you actually buying it?
Sam: No, I’m not. But I was curious. I saw this tweet and I was like — I’ve seen her track record and it’s really impressive. Better than most hedge funds. So I was wondering: does the stock actually move when Pelosi makes a trade? And our girl moves weight.
The Trade Shaan Is Actually Making [00:08:00]
Sam: What’s the trade you just did?
Shaan: Disclaimer: not financial advice. I’m very bad at stock trading but I persist.
Shaan: I noticed there’s been a ton of negative sentiment around Google over the weekend, because their AI product Gemini is — how do I say this — super woke. They released Gemini, which is their answer to ChatGPT, formerly known as Bard. And by the way, there’s this great tweet that goes around every time Google releases a product or renames something. It’s like: “Cool, should I check this out on Meet — formerly known as Google Meet, formerly known as Google Hangouts, formerly known as Google Hangouts Plus, formerly known as Google Duo?” They rename constantly.
Shaan: So they renamed Bard to Gemini. Better name. And basically, people were asking it to generate images. It would generate a great image of spaghetti. Fine. They’d ask for a Viking — it generated a black Viking. People said, “Huh, that’s weird. Can you generate a white Viking?” It would generate a Mexican Viking. “Can you generate an image of a white person?” “Nah, I can’t do that.” It was basically either saying no or generating non-white images. “What ethnicity was George Washington?” “Well, it’s highly debated — he might be Black.” Things like that.
Shaan: People were sharing this everywhere. There are two tribes: the anti-big-tech tribe and the anti-woke tribe. Both got riled up simultaneously. Sundhar the founder of Mixpanel said “Google has lost its way.” Elon Musk said the bureaucratic blob inside Google won’t let them fix it. The All-In podcast was like, “This is a freedom of speech issue.” Everybody’s anti-Google.
Shaan: And I woke up this morning and thought: Google still owns Gmail. Google still owns YouTube. Google still owns Search. Chrome. Android. Wayo. So I bought Google stock today, because Google’s on a dip from the negative PR, and I think it’s just the old quote: the stock market is a popularity contest in the short term and a weighing machine in the long term. YouTube alone does $32 billion a year in revenue — more than Snapchat, Pinterest, Twitter, and TikTok combined. That’s just YouTube. Google Cloud does $36 billion. Android. The Play Store. They have too many assets.
Sam: I don’t think you’re wrong. But I subscribe to the subreddit r/money and I see so many posts from 20-year-olds who are $20K in the hole from options trading on Robinhood. I am so against individual stock trading, even though I think you’re right about Google. It’s a slippery slope. You’ve won a few times recently —
Shaan: I’ll tell you every time I win, don’t worry.
Sam: — but you’ve lost a bunch too.
Shaan: Of course. You can’t trade without bad trades. But it’s also an excuse to learn. I pay this guy $500 an hour once a week to teach me about AI. I wanted to understand the tools, the limitations, the bottlenecks. Some people need to learn by getting electrocuted — Andrew Wilkinson said he likes to walk around with a fork finding sockets to put it in. That’s how I learn too. And maybe the real lesson from trading is just: don’t trade individual stocks.
Analyzing Your Own Investing History [00:20:00]
Sam: My partner Joe did the same thing — looked at all his investments, compared to what he’d have had just indexing, and the index was way higher. He’s switching to indexing.
Shaan: I did the same calculation. I went through every single trade and asked, “What story does this tell?” I thought I’d find you’re not as smart as you think, but I was surprised. Actually, almost all my losses weren’t from buying the wrong thing — they were from selling too early. I sold a bunch of things when market sentiment was down or I was feeling fearful, and I moved to cash. All of my actual losses relative to the market were in the sell, not the buy.
Shaan: The two times I actually bought and lost: first, during COVID I bought some momentum trades — I bought Zoom early and it was working, so I bought more. That was stupid. Second: random tips from smart friends. Those were my actual losers.
Nancy Pelosi’s Track Record [00:25:00]
Sam: Let me just tell you — the last big trade I know of from Pelosi was July 2022. She and her husband Paul bought 25,000 shares of Nvidia at $165. It’s currently trading at $800.
Shaan: A little 4.8x for our girl Nancy. Pretty impressive.
Sam: When I first moved to San Francisco I lived in this warehouse with four other guys. One of them worked at Nvidia from 2009 to 2014. If he had $150,000 of equity given to him over four years — which seems reasonable — and didn’t sell it, his net worth would be around $35 million. And he wasn’t an early employee. He was one of thousands. Isn’t that insane?
Shaan: Nvidia has been insane. The S&P 500 was up 24% last year. Nancy Pelosi was up 65% — triple the S&P’s performance. As her side hustle. While she’s Speaker of the House.
Sam: What’s the right policy here? I’m an idiot about politics, but what I would say is: pay these people a huge sum — $2-3 million a year. There are only about 535 people in Congress. Pay them enough that they can’t speak elsewhere, can’t consult, and all their money has to be in a political ETF or blind trust so we know every trade they’re doing. It’s kind of ridiculous that she’s able to do this.
Shaan: I mean, it’s technically her husband’s trades. He’s in PE — this is his job.
Sam: That’s kind of the whole issue.
The Harbor Baby Monitor Product [00:32:00]
Shaan: Let me show you a company that launched this week — Harbor. Harbor.co. You remember Deep Sentinel?
Sam: The camera company where someone monitors your cameras live?
Shaan: Exactly. Ring is a great way to watch your stuff get stolen. Deep Sentinel is different — there’s someone on the other end watching live and they’ll call the police. I’ve had a drunk Airbnb guest think my house was theirs, knock on the door at 2 AM, and they called the police and took care of it.
Shaan: Harbor is basically the same concept but for baby monitors. There’s someone monitoring the baby monitor. When your kid’s been crying for 9 or 10 minutes, they ping you and tell you: now you actually need to get up.
Sam: What do you think?
Shaan: I have a few thoughts. First — you basically described the whole baby monitor market to me like I’ve never had children. “Have you ever heard of sleep training?” Dude, I’m a father of two. Second: this whole class of products is supposed to be anxiety reduction, but it’s actually somewhat anxiety inducing. There’s already Owlet — the ankle monitor for babies measuring oxygen levels. If the baby stops breathing, you get notified. SIDS is the biggest nightmare for parents. That actually makes sense to me.
Shaan: This Harbor thing, though — let me know if my baby’s crying? I know if my baby’s crying. My house is not that big. I’m not super into this idea.
Sam: The guy who started it founded Misen and Maine, that clothing brand — it’s massive, like $100 million-plus. He’s doing something here. I invested a tiny amount — a thousand bucks — just as a play. I like these monitoring businesses. But I’m not sure about this one specifically.
Shaan: It’s like a similar concept to that My Body Tutor service — someone holding you accountable, checking in on you, making you accountable. The number one thing for diet isn’t having the perfect plan. It’s awareness. Bringing your attention to what you’re eating regularly, morning check-ins. You just need to look at it consistently. That’s what these monitoring businesses are doing.
Penske Media Corporation — The Hidden Media Empire [00:45:00]
Sam: Have you heard of Penske Media?
Shaan: No.
Sam: Okay, so most people haven’t. That’s why I wanted to bring it up. There’s this guy named Jay Penske. His father is Roger Penske — you know those yellow trucks? Penske moving trucks? Roger Penske was also a race car driver and self-made billionaire. He owns a chain of auto dealerships, owns the IndyCar Raceway, the Indy 500. And then he has this son named Jay.
Sam: When I Googled Jay Penske, I wanted to hate this guy. Immediately tell me what you see.
Shaan: He’s too handsome and too rich for you.
Sam: Too handsome! Too rich. I think his wife is a Victoria’s Secret model. So he’s doing great. I googled him shirtless in order to see if he had that too. He does. But I looked him up and I completely love him.
Shaan: Okay, what does his company do?
Sam: You’ve never heard of Penske Media, but let me tell you what they own. They own South by Southwest. They own the Golden Globes. Rolling Stone. The Hollywood Reporter. A large chunk of Vox. Variety. Billboard. Women’s Wear Daily. New York Magazine. Eater. The Verge. Art News. Art Forum. Art in America. The Robb Report.
Shaan: This guy owns South by Southwest and Rolling Stone?
Sam: Yes. He’s been called the Rupert Murdoch of entertainment. He’s really under the radar. Between all the properties, something like 1 in 2 Americans visits one of their websites every month. They get hundreds of millions of monthly uniques. And they’re one of the few large media companies that has been consistently profitable for years.
Sam: He originally got into digital by buying mail.com and trying to create a new email service. It didn’t work. He sold the domain for a profit and then started an ad network in the 2000s. Slowly bought publications to put ads on. That became a flywheel. Over the last 20 years they’ve just kept buying.
Sam: They raised $200 million at a billion dollar valuation a couple years ago and used that for more acquisitions. They have 2,000 employees now. The guy still owns 60% of the company.
Shaan: And he took no money from his dad?
Sam: That’s what he says. He allegedly bootstrapped it for a long time. He says he started with his own small sum and slowly rolled it — one acquisition leading to another. The people who’ve worked with him say: “He has a chip on his shoulder, wants to prove himself, not to the world but to his family.” Another person said: “When he hires, he interviews every single person. When he buys a company, he wants to interview everyone who works there.” And he’s known for being incredibly kind — winning over difficult personalities through just being polite and having their back.
Sam: The only thing I found on him that was a knock was he got arrested for urinating outside when he was drunk on Nantucket. That’s literally the only time people have disliked him.
Shaan: Would you want to do this? It seems really hard — rolling up media properties, a dangerous space.
Sam: Absolutely not. Vice just shut down. BuzzFeed has a horrible market cap. Media is not the most profitable industry. Having 2,000 employees and operating 15 things is just a hard way to live. But someone is doing it — and actually doing it successfully. The way he does it is by being a good operator: he balances letting people do their thing with being pretty strict about operations and profitability.
Sam: But Jay Penske is one of the biggest names in media that almost nobody is talking about. That’s why I brought it up.
Shaan: Also hilarious that he named the company Penske Media Group. He’s like, “I want to make a name for myself” and then slaps his own last name on everything.
Sam: Right? “I’m going to prove myself separate from my dad.” Then: Penske Media Corporation. Very on-brand.
Sam: All right. That’s the pod. I’ve got my stock pick in. We’re going to check on that Google trade in five years.