Maxine Minter: Okay, three, two, one. Hey, I'm Cheryl. I'm Maxine. This is First Check, part

Cheryl Mack: of Day One, the network dedicated to founders, operators,

Maxine Minter: and investors. If you want to be a better early stage investor, this is the show for you. So TLDR, if you don't

Cheryl Mack: want to suck at investing, listen up.

Cheryl Mack: So Maxine, how did you get started angel

Maxine Minter: investing? Yeah, I, I mean, I have a, what I actually thought at the time was a really like unusual story, but the more time I spent in the space, the more I realized it's actually like not that uncommon. So my journey was actually like so many things in my life. It was being around people who showed me a way of doing it and then just kind of starting and learning from there.

Maxine Minter: So angel investing in particular, I first learned about the concept of venture capital at college. At Stanford, they have a bunch of folks come in to talk to you about, you know, being an investor and how do you start angel investing? How do you start investing at funds? What kind of companies, you know, do they look for, et cetera?

Maxine Minter: In hindsight, I realize it's their marketing, but at the time I was like, this is really informative. Excellent. And so that was my first kind of introduction to the concept of being a venture capital investor and investing in startups. My first actual experience, excluding some like, early checks that I wrote that were more like charity than I thought of them more like charity and not as an investment, but my first like thoughtful investment.

Maxine Minter: Um, I did because of a group of friends from my co-working space who were starting an angel investing group and they were just investing alongside each other. Uh, it's now scaled into a really awesome organization called the council. Actually, of the first founding members, I think there were like nine or ten of us.

Maxine Minter: And, like, 80 percent of us now have funds or are partners at funds, so that's kind of a wild progression. It's pretty cool. So we just started diligencing deals together. It actually, like, it was extremely informative for me on how important like a community to get started is, and also kind of how much it builds community by doing it.

Maxine Minter: But yeah, so we just put diligence deals together. And then the first company I invested in was a company called Zeta. A DTE is incredible. Um, I started angel investing largely because, number one, I wanted to learn about it. And number two, I really was infuriated by the fact that I couldn't find any non, you know, middle-aged white guys for my cap table.

Maxine Minter: And so, I really wanted to change that. And so, my first check was a 2,500 check into a company called Zedart and Aditi. She's still doing an excellent job. Just an incredible founder to watch. That was pure luck though, right? That first check was like, um, I like it. I invest. Uh, but that was my first one.

Maxine Minter: What about you? What was your first angel check?

Cheryl Mack: Yeah, I, I guess like, I wasn't so purposeful about my first check. I definitely fell into it more by accident. I was actually, I already knew about the concept of angel investing and venture for years. And I had always said, like, I'm going to be the person that helps founders connect with capital and helps investors deploy capital, but I'm not going to be the one that deploys it.

Cheryl Mack: And I think that was more of just like, I didn't think that I could. And so, rather than, uh, yeah, we talk a lot about permission, um, you and I, and this is one of those things where like, I, I just, yeah, why?

Maxine Minter: Why didn't think you, you didn't think you could?

Cheryl Mack: Well, first of all, there's a number of things. So like, basically what happened was, I was working with a number of startups and, right, right.

Cheryl Mack: I was like, I was, um, working for equity with a number of start for equity for a number of startups. And one of them, we were out for drinks one day and he's just like, yeah, I'm just like raising, I'm finishing trying to close out my round. And I was like, oh, cool. How much do you have left? And he was like, oh, 20 grand.

Cheryl Mack: I was like, really? But just 20 grand? Like I thought. I thought in order to angel invest, you had to write like 100,000 checks. Like, you're saying you're just looking for the last 20 grand? I was like, I could do that if that helps you get back to running the company. And so that was kind of that moment where I was like, oh, actually, like, I guess you can do this for less.

Cheryl Mack: Um, but I still didn't really think of myself as an angel investor because I just thought like, oh, I just, you know, invested that one amount for that one founder so that we could continue running the company. And yeah, you know, we could be done with that whole capital raising thing. But then it happened again.

Cheryl Mack: Where I was talking to another founder and similar thing. He was like, yeah, just trying to close out the round got like 25k left and I was like, oh I could do that and it was at that point after I was like the second one that I did. I was like, oh, hmm, maybe actually this is what angel investing is and maybe I should learn more about it because I feel like this is going to happen again.

Cheryl Mack: And so that's why I was like I'm gonna call up all the investors that I know and they happen to be VCs because I wanted to help connect founders with VCs. That was a lot of what I did at the time and I was like, hey team, uh, I think I started angel investing. Tell me everything I need to know, go. Um, and I got a really, I got a lot of really good advice.

Cheryl Mack: Um, but one of the things that I didn't find, which I'm so glad that you did, but I'm a little, a little bit jealous is that I didn't really find a community of angel investors when I first started five years ago. When I went out to look for that community, I found that there it was pretty much non-existent. Like, there was no community available, and the ones, well, there was no community available that I felt I could be included in, because the ones that did exist felt very exclusive five years ago.

Cheryl Mack: Uh, and a bit of, like, boys club, kind of, um, rules in place that I didn't necessarily meet, and, and so I struggled to to find a community of investors to learn from and work alongside and nobody would do diligence deals with me. I had to like pester people being like, hey, what are you investing in? How do I get on that? Like, tell me why are you investing

Maxine Minter: in that? Yeah, it's actually, um, I have realized in hindsight just how lucky I was to start angel investing with a community of people I identified with. Almost no one I know learned to invest alongside, like in my case, a bunch of other women.

Maxine Minter: Yeah, and like, women from that's super rare. A wide range of socioeconomic backgrounds, cultural backgrounds. Like, the Annabelle, Courtney, and Amber, the folks that kind of put it together to start off with, it was really important to them that they had capital allocators from diverse perspectives around the table.

Maxine Minter: And so I had like, it was almost, it wasn't normal for me because I'd experienced the broader capital market, but actually just like the learning journey, my initial instincts and my initial development was all about like thinking about diversity. In your funnel, like thinking about how to spot opportunity in different types of people, which I'm just like so grateful for.

Maxine Minter: I also think it reflects that I was lucky enough to learn in an ecosystem that was more developed, right? Like I learned in the Bay Area. I didn't learn here. Yeah. Because of that. Like, it's super hard, but the good news is, is a lot of that is changing, right? Like, now, for today, as people are thinking about on ramps, there's so many different identity groups that angel invest together on platforms like Aussie Angels and in other angel groups.

Maxine Minter: So excited to kind of dive in what's possible today, but yeah, it's just like, I have a distinct, distinct visceral memory of trying to talk about businesses with people in my network before I moved to the U.S. At the time, like, there was just like, at least in my world, startups and business building, like, wasn't really big in the communities that I was in.

Maxine Minter: And there was like a handful of people that were entrepreneurial in my world. And I have this like distinct memory of trying to like corner them at parties and like talk about the businesses they were investing in and like talk about how they drive value and like consistently just flubbed me off. Right? There's just like default assumed. I had no idea what I was talking about.

Maxine Minter: And like there was definitely a moment of joy when they would like start to reach out to me when I was back in the Australian ecosystem and be like, hey, I like got this deal. I'm interested in investing. And I'm like, oh, now, now you want to chat.

Cheryl Mack: Now you want to chat. Oh yeah. Okay.

Maxine Minter: Cool. Yeah. But I totally get it. You take it all in

Cheryl Mack: stride though. You're like, yeah, yeah, yeah.

Maxine Minter: And so on...