Molly O'Shea on venture funds as F1 teams, family office investing, and the TikTok deal

deleting this app moment uh by anyway, I think we got Molly. Let's bring her back into the studio. We'll ask her if she's had coffee or if she is raw dogging reality today. Let's see. Molly, are you there? I'm here. Are you raw dogging reality or are you caffeinated today? I've had about five matchas and two espressos.

Wow. Getting up potentially into that 500 milligram range, which is that's that's junkyard dogging reality. That's just consuming everything. Maxing cons uh maxing. Did you have a rough time uh like with you know going to the East Coast last week?

I think for for me personally, given my caffeine intake, when I go when I when I go through a time change like that, just everything gets messed up. How how did you do? Horrible. I've been up since 4:00 a. m. every morning. That's a good thing. That's a good thing, though. That's good. Just cranking content. Yeah.

Just Ashton Hall mode. Ashton Hall max thing. Yeah. Get up. No, I think it's time. You have to do one of the it I think you need to do the the Ashton Hall for tech video. I think you should basically start tomorrow morning when you wake up at four. Y and just do it. Yeah. Anyway, I'll I'll try my best.

It's great to have you on the show finally. Long overdue. Um there's a bunch of stuff to run through. We have limited time unfortunately, but uh maybe we'll maybe we'll make Augustus wait, you know, a couple minutes extra and just hang out. We we already covering your F1 uh firms as uh or sorry F. What inspired it?

What was the reaction? What do you think you got right? What do you think you got wrong? and then we'll go into the other less iconic F1 teams. Take some shots. Well, uh, so all of this started because I got a nice tip from someone who might be on the inside.

I can't share much more than that, but I was given a tip because I've done these before where I've compared the VC funds to something like the Coachella stage. I did this for sorcery like years ago and it went so well, but this was at like ZERP funding and like Zerp environment.

So, it was like SoftBank was in it and Tiger and like it was just so much more clear who the stages would be and now now we're dealing with F1 because there's only a couple contenders and we just have to we've got to see who's going to win. Uh, going back to the Coachella, which fund was the D lab? I got to ask.

It's the D lab. Oh my god, that's a good one. I forget. I've never been to Coachella. You've never been to That's extremely bullish. That's extremely bullish that you've never been to be honest. I've never been to Coachella. Sweet child. Sweet. Your sweet child. It doesn't know what the D lab is.

Um but but who do you have as a DOLAB? I got to know. And then Sahara and then then we'll move on to F1. Okay. I mean, let me let me pull this up. Well, uh while you're pulling that up, uh there are some midfield teams that someone broke down. Uh Williams is Greylock, the fifth most winning team in history.

didn't keep the top talent uh or scale so fell behind. Alpine is BCV capital venture storied brand across racing categories. PE consulting strong veteran lineup couple wins and podiums in recent years. Decagon Craya younger guys largely untested no clear succession.

I love Alfatari as as YC battleground for young talent produces some of the best drivers but sees limited return for Stapen Sains. Gastley plays an important role in the startup driver ecosystem and Aston Martin is SoftBank. One mind, one man behind it all. Lawrence Stroll, Masayoshi Sone. Tons of money and big deals.

Uh, no significant results to speak of. Brutal. Brutal. It's great. Anyway, uh yeah, break us down the uh the uh uh the the Coachella uh landscape and then uh I thought I'd put in terms that uh folks that are more familiar with bodybuilding could uh could key off of.

Okay, so for DLAB, okay, yeah, this this one was just scrappy bootstrapped companies or people in stealth for the main stage we had is Tiger Edition, CO2, A16Z, and crossovers. Oh, so it's basically the lineup crossing over. Okay, I got it. It's uh the big show headliners, hard to compete, expensive rounds. Got it.

And then for for outdoor theater, which is just as experienced, arguably more fun, artist friendly, we had first round benchmark, pair and index. Okay. Yeah, that track sound Sahara. Sahara, which is also like amazing, very large, loud, and a little bit more out there.

Founders Fund, Soft Bank, General Catalyst, Lust, Lux, Craft. Mhm. Um, let's see. Go. Delian playing uh the Sahara stage right around like 6:00 just really, you know, peaking basically. Peeking. Um um well, yeah, I mean I never been to Coachella. I barely get to watch F1.

I'm I really only follow the only sport I follow is bodybuilding. So I did my own kind of version of this mapping the top venture capital firms to professional bodybuilders. So, I'll I'll give you a rundown and I'm sure you're familiar with bodybuilding, so you'll be able to give some feedback and tell me how I did.

So, for Sequoia Capital, I have Arnold Schwarzenegger. They I mean, this one obviously it should be obviously sports uh the industry's gold standard early. Sequoia, Apple to Airbnb hit list and Arnold's seventime Mr. Olympias. It became the blueprint that everyone studies, right?

Uh Andrea and Horowitz, this one should be obvious. Dorian Yates, of course, each burst in with radical mass, you know, software eats the world media blitz, six straight Olympias. They kind of reset what scale and intensity could look like. Uh, for founders fun, I mean, this is a no-brainer.

Phil Heath, uh, precision obsessed moonshotters, Teal's Contrarian Bats, Heath's near flawless symmetry, both racked up seven crowns while defi dividing the crowd. Little controversial, Heath, uh, Kleiner Perkins, Ronnie Coleman. Obviously, I mean, everyone's going to guess that one course.

Um, course, you know, they're 1990s Titans that went maximalist. KP's do era supremacy, Mirs Coleman's eight title. Yeah, buddy. Yeah, buddy. That per that pushed sheer size and later paid for it in surgery and turnover. Uh, Excel, you got Lou Farero. Lux Capital, you got Jay Cutler, course probably makes sense.

You know, he's a he's a methodical grinder just like Lux. They've been at it for a long time. Lux's deep tech persistence and Cutler's dogged prep. Finally dethrone the champ uh showing steady focus beats flash. Lastly, we got Natt Freriedman. He's the upandcomer. He's the Sam Sulk of Sam.

People have been saying that for a long time. Many people have been saying that. Yep. So I I think that will put, you know, the venture funds in terms that really anyone could understand because a lot of the F1 analogies, they just don't really land with like our audience at least.

Bodybuilding is very American whereas F1 is very European, right? Um, what what else is on your mind, Molly? How how was uh what was your reaction to last week? We obviously uh were uh in DC as well. Did you have any major takeaways? Any anything you know that you're following uh after the event?

You got some Palunteer merch. I got some Palunteer merch. Um became friends with Iliano there. Got introduced to Sham. Got a private tour of the office on Friday or the next day. Um some amazing work they got there.

But I think like the biggest takeaways and I'm still seeing this, but the the biggest theme from the event was the US vers China and we're seeing that because Delian's still posting about it. He's posting through it for sure. He is. He is. Um, yeah. An interesting one.

I I we'd heard some light chatter about uh the Tik Tok deal potentially getting closer to a resolution, but there being uh general uh unhappiness with how it was getting sort of resolved. So, not sure how much we can share, but that was one takeaway for me.

It's like in the midst of this like massive trade war y uh and and all this talk about USChina uh one of the sort of key issues that should be completely bipartisan and and uh we should be acting uh extremely intensely around it seems like we're going to miss the mark on.

So I think consensus is that there will be a group of financial investors that come into the company and own a stake and then Oracle will do the data management and kind of the the cloud infrastructure but it won't fully leave control of the CCP which is maybe not the best outcome.

I've been advocating for just giving all of Tik Tok to Truth Social. Um I think that would be something that everyone could really rally around. Yeah. Might destroy it. Might but. is definitely going to get approval from the from the top dog in Washington. He'll be happy to have an asset. Yeah.

Um what what else what what what can you tell us about uh working at a family office? How it differs from working at a VC firm? You've obviously worked at in in both places. Um what's different and and how how are family offices like positioning themselves these days in venture?

Is it just like tagalong rounds or are they trying to lead rounds? Like what are you seeing in the family office landscape? Good questions. many questions. Um I think the biggest difference is the time horizon on deals and the thinking. So instead of capital. Yeah, it's permanent capital. You're thinking evergreen.

It's not you're not confined to four years um for investing. It's not like you have to stop investing after two and a half years and start raising and going out to fund raise. Instead, you're thinking long term.

You can actually like be like a little bit more thoughtful instead of playing the rat race of competitive rounds. you can pick companies and go deeper with them, have longerterm relationships. It's it's just like it's a much different game because it seems much more rational.

You I think my biggest um my biggest thought and reflection after leaving institutional VC was just like how much it's thwarted by fast decision making.

If if you have to consistently confine to, oh, I've got to do this many deals a year, you have to do this many per fund and allocate x amount of capital, then it really constrains like your judgment and how you think about what you want to do. So, the Yeah. I mean, it's great because like you can operate with clarity.

You don't have to waste your time with tons and tons of meetings. You can actually just focus on the power law winners. Yeah. Yeah.

And that that means, you know, effectively, you know, identifying a company early, not necessarily being able to invest in that moment for some particular reason, but just saying like, hey, it doesn't really matter. We want to get in at some point. Let's, you know, continue to build a relationship.

Whereas, I think oftentimes VCs, you know, have a specific window unless you're a big platform fund. You have a window where you can make uh an investment work, but then you can't even do an SPV into the company necessarily if you weren't in the, you know, in one of the earlier rounds.

And so having that timeline flexibility to be like, okay, you know, we can have 10 plus billion dollar outcomes now. It really doesn't matter if we get in at $und00 million or we get in at $500 million, you know, post. So it's also just it's much more flexible capital.

It's not like you're confined to an X amount of percentage that you need in equity or check size. Like you can get in whenever and whatever makes sense. And then you can also put in your own capital and then raise the rest through SPVS and make a larger round. So there's many different dynamics.

It's it's much more friendly. Uh you you dropped an interview with Bucky Moore. He's going over to Lightseed. We're having him on the show later. Uh what was the question that you know you were too afraid to ask because it doesn't meet Sorcery's brand standard, but you know, it's anything goes here when we're live.

So we can put him on the spot. What did he ask you to like edit out and then we'll ask him that live. I will say I I passed all compliance. My biggest question that I wanted to ask him was what was the deal? Like did you get your carry bought out? I asked this. You got to listen to the interview so you get the answer.

I'm telling you. I'm prepping my show. Yeah. But I asked him like how does it work transitioning um large partner from another fund going to another, right? Like there's a lot of tied up carry. There's board positions. It's very complex. Like what was that process like? And we walked through it. I mean he was very open.

I was quite surprised. It was an awesome interview. That's very cool. Um, what what else did you talk to him about? Um, uh, that we could maybe dig in deeper when he hops on the stream in an hour. Um, ask him about his view on ASI. Ask him about pricing dynamics for tier ones and tier twos.

He doesn't like that branding, but um, you think more as like tier three. He wants that he wants to be labeled as a tier three so he can have that dog. Yeah, that dog inspiration to grind harder. As soon as you're labeled a tier one, you just you're like I have reached I've peaked.

Anyway, um and then I would I would also I would ask about global pools of funding. He was open about that. Um and he's big on raising money from Pyongyang, right? North Korean money is is usually in his funds, right?

He does a lot of SPVS with uh somebody out there is not gonna not gonna understand with the North Korean sovereign wealth fund. Yeah, we'll have some fun with him. Uh last question before you go. What should they do with Alcatraz? Everyone's been debating it in tech. We I want to get everyone's take on it today.

Should they become Y Combinator? Put a monument on it. Put it bring back the jail. Keep it as a tourist destination. What's your pick? I want to keep it. Uh, no. I want to bring it back as a jail, but I want to keep it open for tours. Okay. So, you can tour the prisoners. Crazy. Crazy. That would be very chaotic.

That would be extremely chaotic. Somebody was running for it. I forgot who it was.

I think it was Shiel was saying that like the reason that it was shut down initially was that uh uh there there you could only have like 300 prisoners and like due to being on an island that was like extremely expensive, 3x the cost to actually house them. So, it was just like doesn't really actually make sense.

Um, but uh I liked it. If I was in jail, I'd probably choose the island jail, right? I mean, that that doesn't seem like a bad place to be. I don't know. Have you been Have you done actually bleak? It's so bleak. It's always super kind of see everything, but I don't know. Yeah, pretty terrifying.

Anyway, we'll see what happens with it. We'll be tracking it. I'm I'm in favor of putting, you know, letting Y Combinator set up shop strategy. It's PMF or die 2. 0. Yeah. Yeah. Yeah. Y cominator is the Y cominator of Y cominator as many people have said but put it on an island. That's a great place to be.

Thanks so much for stopping by Molly. Well yeah this was great Molly have you back on soon. Congrats on all the progress. Bye guys. Back to you. Let's bring in Augustus to Rico from Rain Maker. I got the gong ready. Got the gong ready. I think we got some breaking news from Augustus. go.

Um, yeah, we we we we had a chance to sit down with Augustus in DC, get the update from him. I loved that, you know, his business is cloud seeding, making it rain, and he somehow tied it into the AI race to develop more data centers and it