The Exchanges

Q So in terms of your portfolio, what types of companies are you investing in? I know you mentioned software. You're leaning into that. You're looking at early stage. What do you, what's your target zone?

A So ultimately I'm investing in anything I wish I had when I was building my business, right? I started Nasty Gal and The end of 2006. Like I had to have a CTO to have a, you know, but just a shopping website. Right. And so there was no gusto or just works or, I mean, integrations like project management software, creative tools. It was Photoshop, but everything kind of required you to be an expert to cobble it together. And now anybody can start a business. There's all the software that makes being a creative or collaboration or invoicing All of these things so much easier, and I've just, I've watched very enviously as a former founder, these products emerge, and having not had them, I understand what the people, what, why a particular software or product might be needed, and so that's the filter I look at my investments through, um, because you can say that somebody needs something, but if they don't Really needed. It might just sound like a good product, and I don't, you know, I think, ah, investors who don't have operating experience or haven't been founders, I can't really imagine how they would evaluate that opportunity in the same way, because I have it just kind of like, it's like in my DNA to understand that. Um, and it's, you know, it ranges from, you know, agree.com is connecting contracts with payments, so As soon as somebody signs an agreement, they're taken through…

AI assessment note: “I'm investing in anything I wish I had when I was building my business”

Q you know, they have a billboard up about it. Like, and they don't need to have a billboard, but they do because they're creating a vibe. And like, there's a lot of vibe building for all of these companies. That's Becoming like essential for customers. It's for investors, for everything. How do you, how do you think about how important that is for these companies and where should they start?

A What I found is that just getting your first customers is the most important. So that's, you don't have to have the perfect website. You have to have, you just have to stand up a product and see what people think and if they're using it and how they're using it and talk to them. Um, and beyond that, then it's like, okay, You know, even if you're not putting out huge press releases, you know, companies like Plot, and Nectar, My Portfolio, and Agree.com, two of those companies just raised their seed rounds, um, are hosting events at Shop Talk, where there are CMOs and CEOs who would be their customers, um, they're hosting dinners in New York, Agree's out there doing guerrilla marketing like they're at, I think, Saster, and all of the people in the parking lots are, like, standing in the sun, you know, Directing vehicles. Collecting. They just gave them all agree.com hats, you know, and so like anybody who enters, you know, via the parking lot or is, you know, getting their ticket checked is seeing something for great, you know, it's like they're in front of the entire audience at this event, which is just really brilliant. And they're like, you know, they're a company that's going to replace DocuSign. DocuSign would never do anything like that. Um, and so, these are super early stage companies that are doing this stuff, um, you know, you know, very early on. Actually have, um, th…

AI assessment note: “What I found is that just getting your first customers is the most important.”

Q have almost a million followers across all your social channels. You had a Netflix series, you had a book, you founded Nasty Gal, Girlboss, and also business class. So I'd love to get into that and understand, okay, going into the next chapter of your life, you've founded Trust Fund. How did your early innings of building out brands and, and communications and strategies lead you to this venture fund?

A Yeah. I mean, the communications piece Kind of came after the decision to start a fund. And, you know, I started a fund because I had raised venture capital. I raised fifty million dollars back in 2012. You know, the company was valued very highly and ended up establishing really great relationships with people who have now become my LPs. And when I, you know, thought about branding, I don't know why I'm just, I enjoy naming things. It is so fun. And I thought Trust Fund would be a very funny name. What's funny here now, Is that there is more of a cult, like a proper culture of kind of trust, like people can laugh, I feel like people can laugh at it a little bit more in the states, and like kids with trust funds or whatever will wear the trust fund bucket hat because it's kind of ironic, and then people who don't have trust funds will wear a trust fund bucket hat because it's also funny. I think it's like kind of ironic for everybody.

AI assessment note: “ended up establishing really great relationships with people who have now become my LPs.”

Q really high price, but it does shoot you in the foot, uh, to, to live up to that and then have to meet all of the metrics and expectations that come with it. Like there are definitely strings attached. Is there any way to rationalize this For those in, those young, younger founders, or do you think that it's just, that's gonna be a bucket that will always be around?

A You know, when you raise at the highest possible valuation, you might not be thinking about the things that are most important, and, you know, as a founder who really did go on a victory lap and do, you know, the, you know, the huge press thing, It didn't make a huge impact on the business. It ended up putting me front and center, which is an amazing asset and something that, you know, I utilize with everything that I do, but it didn't build the business. And when you're, you know, flaunting numbers, your customers don't care. They care about who your clients might be because they want to know that AG one or, you know, whatever is A customer, and that brings you credibility, but the people who would be your customers aren't looking at how much that you've, you've fundraised and making decisions about whether they want to use your product or not. So it's really kind of like a circle jerk. It's not, Any indication of success, and it really is an indication of, I think, the wrong, you know, having just maybe misaligned priorities because, you know, fundraising is just something that you do to, you know, further your business, be able to move faster in a category where other people are going to, you know, move fast next to you, and you want to take up a significant market share, and you're building something that's Extremely scalable, which software can be, but it's no indication o…

AI assessment note: “when you raise at the highest possible valuation, you might not be thinking”