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Navigating Pre-Seed Investing: A Conversation with Anabel Lippincott Paksoy

First Cheque

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Summary

Anabel Lippincott Paksoy, partner at 43, discusses the importance of building communities and their role in early-stage investing.

She shares her experience creating the council, a female-first investing group, and emphasises the need for a deep understanding of founders and their motivations.

Anabel also highlights the value of professionalising angel investing and finding founders with a strong sense of purpose and followership.

She concludes by discussing her investment preferences, focusing on niche communities and founders with a deep understanding of unsexy problems.

About The Guest

Anabel Lippincott Paksoy is a partner at 43, a pre-seed fund based in the Bay Area. She is also a partner at The Council, a female-first investing group. Anabel has a background in people operations and has a passion for building communities and supporting early-stage founders.

Key Takeaways

  • Building a community is about creating a space for like-minded individuals to connect and share deal flow.
  • Investing in early-stage startups is a high-risk asset class and should not be undertaken unless one is aware of the risks and willing to lose the money.
  • Angel investing can be treated as a learning budget, focusing on maximising learning and gaining experience rather than making immediate financial gains.
  • When evaluating founders, looking for a deep, authentic “why” behind their venture and a strong sense of purpose is essential.
  • The ability to pivot and adapt is crucial for founders, as it demonstrates a willingness to learn and iterate based on feedback and market conditions.
  • Successful founders’ ability to attract top talent and inspire followership is a crucial trait.

Quotes

  • “I think the thing that I needed, and again, it’s interesting how trends have shifted, too. Even in 2018, five years ago, it was a little new for operators. These female operators were not already super independently wealthy, to think about deploying capital as independent investors into startups.” – Anabel Lippincott Paksoy.
  • “I think the thing that I know that I look for in people is some kind of deep, deep, deep, deep why that they’re doing what they’re doing.” – Anabel Lippincott Paksoy.
  • “I want to feel that conviction, and there’s no way to vet that. That’s where it gets super personal. I want to ask, could I fall in love with this founder, and I don’t mean romantically? I mean, would I go work for them?” – Anabel Lippincott Paksoy

Resources

Timestamps

0:00:00 – Introduction to the podcast and guest.

0:01:57 – Discussion about Anabel’s first investment.

0:05:04 – Conversation about nostalgia and fashion trends.

0:06:12 – Exploring the concept of building communities.

0:09:48 – Challenges and principles of community design.

0:10:30 – Constructing a community for sharing investment deals.

0:11:55 – Creating a learning platform through a consortium of investors.

0:13:14 – Frustration with lack of conversation about deals in the peer group.

0:15:15 – Directing new angel investors to be aware of high risk.

0:17:31 – Treating angel investing as a learning budget.

0:18:48 – Normalising lower entry prices for angel investing in Australia.

0:19:24 – Contributing to the founder’s journey as an investor.

0:20:28 – Small but mighty checks with added value.

0:21:50 – Amplifying dollars by offering time and expertise.

0:21:58 – Dustin’s investment strategy at 43 is an example.

0:21:50 – Introduction to the topic of angel investing and fund structuring.

0:22:59 – Anabel discusses her current project, 43, a pre-product fund.

0:24:14 – Professionalising the angel check and capitalising angels.

0:26:18 – Raising a fund to capitalise full-time professional angel investors.

0:27:27 – The challenge of finding founders willing to take early-stage risks.

0:29:12 – The importance of early checks in supporting different types of founders.

0:30:45 – Leveraging background in people operations for founder selection.

0:31:49 – Building conviction and making investment decisions in early-stage investing.

0:33:31 – Looking for founders with a deep, personal, and authentic ‘why.’

0:34:06 – Evaluating grit, resilience, and openness to pivoting in founders.

0:34:41 – Building a rapid learning engine and the importance of followership.

0:36:05 – Evaluate founders through multiple meetings and understand their plans.

0:38:24 – Focus on founders’ backgrounds and solving problems for niche communities.

0:41:46 – Bravery in becoming a parent and writing the first check.

0:42:39 – Losing the first investment but having no regrets.

Transcript

This transcript has been A.I. generated.

Cheryl Mack: Okay. Three, two, one.

Cheryl Mack: Hey, I’m Cheryl.

Maxine Minter: I’m Maxine.

Cheryl Mack: This is First Check, part of Day One, the network dedicated to founders, operators, and investors.

Maxine Minter: If you want to be a better early-stage investor, this is the show for you.

Cheryl Mack: So TLDR, if you don’t want to suck at investing, listen up.

Maxine Minter: Welcome. Today we have Anabel Lippincott Paksoy on the pod and I am so, so excited to have her here. We’ve been friends for a very long time and I have been inspired by her from the day that I met her. I am just wowed by her as an angel investor. She was actually my on-ramp into investing through a community that she put together in SF many, many years ago, which I’m excited to dive in and talk about community with her.

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Maxine Minter: Watching her angel invest, she’s just like incredible at developing networks and communities that are super high signal, really wonderful humans as well and just kind of wonderful thought partners to help be better investors. And she’s done some really cool stuff. She is now a partner at 43 which is a really cool pre-seed fund based in the Bay Area and also a partner at the council and just a wonderful human. So, so excited to dive in today and talk to her about all things early stage investing, pre-seed and community.

Anabel Lippincott Paksoy: That’s awesome.

Cheryl Mack: I don’t know Anabel personally. I’m excited to get to know her a little bit more today, but anyone who started a community for female angels to get together and learn more is A-OK in my books. And I’m also really excited to learn more about pre-seed investing because we don’t have very many true pre-seed investors in Australia. So yeah, really excited to hear Anabel’s thoughts around pre-seed investing.

Anabel Lippincott Paksoy: So welcome, Anabel.

Maxine Minter: Welcome.

Anabel Lippincott Paksoy: Thank you so much. It’s a treat to be here with you guys. Amazing.

Cheryl Mack: So the first question that we ask everyone who comes on is what is the first thing that you invested in?

Anabel Lippincott Paksoy: I think if I really have to rack my brain, it’s going to be a couple CDs.

Maxine Minter: Incredible.

Anabel Lippincott Paksoy: Likely something like an Avril Levine CD in the early aughts, I think. And if I was smart, I would have hung on to those because I think they’re going to be a relic someday. But no, they’ve made their way into landfill at this point.

Cheryl Mack: That’s unfortunate. I heard those get auctioned off for lots of money now.

Anabel Lippincott Paksoy: Yeah, right.

Maxine Minter: If you’re anything like me though, my early CDs, my early CDs, I took them everywhere with me and I scratched them up something fierce. And so especially my favorite songs would be like really glitchy by the time I was ready to part ways and send them into landfill.

Anabel Lippincott Paksoy: Oh, yeah. Theater boy is completely unlistenable at that point. Totally. I was just going to say, I wonder if a disc man would ever have the cachet that a record player does. But I just don’t think the technology holds up the same way that vinyl does. So, unfortunately, I think CDs are in a bygone era at this point.

Maxine Minter: Yeah, sadly.

Anabel Lippincott Paksoy: Unfortunately, not a great investment.

Maxine Minter: Right? Not a great investment.

Anabel Lippincott Paksoy: Do not judge me on that.

Cheryl Mack: And let’s talk about animals investing now.

Anabel Lippincott Paksoy: I’m really good at the early stage.

Maxine Minter: I just don’t know that you could these days convince someone to wear a disc men on their belt in the way that we used to. Remember, we used to carry them around like, it was almost like a discus, like, huge chunky thing. I mean, the headphones back. You’re looking amazing with your headphones.

Anabel Lippincott Paksoy: But thank you so much.

Maxine Minter: The big handheld takes up a whole part of you. I don’t think we could do it.

Anabel Lippincott Paksoy: The whole iPod mini or whatever. The iPod, that whole thing. Just like, when you think back on one of the fun things, I think about our generation. Like the true millennial, not the Cuspy Gen Z generation, but we literally were their first smartphones in their coming of age years. And I think that journey is pretty cool. I’m happy that we’re in our golden years professionally now. Kind of entering into your mid thirty s to early fifty s is like when you can actually.

Anabel Lippincott Paksoy: You can kind of reference it, and it’s still a little bit nostalgic, but at the same time, it’s like, nope, you’re still kind of current at the same time. So I’m having a little fun, I’d have to say.

Cheryl Mack: You’re making me like, I’m right there with you.

Maxine Minter: This is great.

Anabel Lippincott Paksoy: Yeah, no, I’m ready. I’m ready for my Eileen Fisher baggy clothes moment. So that’s where.

Maxine Minter: Perfect. I’m here for it. Definitely a nostalgic moment in terms of there were colots and baggy jeans and those huge echo shoes that I used to wear that I was pretty embarrassed having been through that fashion era for a solid 20 years there. And now I’m seeing the coolest people. Like, Gen Z is wearing those outfits again. And I’m like, wow. Yes. Okay. I don’t feel as bad for those horrible fashion moments. Yeah, we’re back in it.

Anabel Lippincott Paksoy: Totally.

Maxine Minter: Yeah, I’m happy for it. I’m right here for it.

Anabel Lippincott Paksoy: Same.

Maxine Minter: So one of the things, as I mentioned in the little kind of intro, is my observation of you kind of over this part of your journey has just been. You’ve just been incredible at building community. Maybe for our audience. Anabel was the first people hire at Opendoor and went on that journey with the team and then stepped out and joined a female first co working space called the assembly, which sadly doesn’t exist anymore, rip assembly and built the community there and just did like an incredible job of building really high signal, really wonderful human group together in this physical space, and then built the council, which is a female first investing group in the Bay Area and now all over the US, right.

Maxine Minter: Got members in all four corners of the Continental US. So I’d love to just hear how you think about building communities. Why do it? What are some things that you’ve noticed about what works really well in communities? What destroys them? I’d love to just kind of hear your thoughts on community generally, and then maybe we can dive in a little bit deeper, for sure.

Anabel Lippincott Paksoy: Well, thank you so much for the kind words. And Maxine, you’ve always been a huge champion and member of the communities that I’ve been able privileged to be a part of and help build. And it’s been folks like you who’ve kind of stepped forward and highlighted what’s special about it that even gives us the chance to reflect on what is it that we are building here and what is that special sauce. Yeah. I wish that. I think we would not be suffering from a loneliness epidemic or pandemic, whatever, right? And I think we’d all be very rich if we knew how to.

Anabel Lippincott Paksoy: If we had a blueprint for building community that was repeatable and if we could monetize those two things. And I think I say that because I think that a lot of times when we talk about community, people end up wanting to know, how can I go and build a community, tell me how to do it, or I want to make a business out of a community. And I think those two things are super natural. Of course, who doesn’t love the feeling of belonging that comes from a great community?

Anabel Lippincott Paksoy: And then why shouldn’t that be something that you could turn into, like a successful business? However, I think one of the annoying, frustrating, magical parts about true community is that it’s not quantifiable. It’s kind of like cooking versus baking. I like to say it’s a little of this, it’s a little of that. Like why I like to cook and I’m not a baker. Right. It’s like you’re never going to make the same recipe twice, and you can follow the guidelines. But ultimately, what makes each community special is really about the members.

Anabel Lippincott Paksoy: And I think I’ll stop waxing philosophical for a moment and just say explicitly that, yes, some of the communities that I’ve been a part of, specifically the assembly, obviously that was a business in that it was a co working space centered around building community. The council is now a community that has a paid membership and also has a venture fund that spun out of it. So I’m not trying to suggest it can’t happen, but when we look back on some of the precious early moments, this happens in companies as well.

Anabel Lippincott Paksoy: We reminisce about the early days and et cetera. I think it’s that Genesis quo. The thing you can’t really put your finger on is something that I think is this weird unspoken social contract that happens as you’re building a community, which is really, it’s kind of nothing except for a group of people who are either implicitly or explicitly agreed to show up, be in each other’s company and presence, usually around a shared either goal or interest or purpose.

Anabel Lippincott Paksoy: And really your job as a community builder is to try to identify what that common goal is and shared purpose, and then really just hold space and design the container for that. And what I mean by container, I mean like operating principles, so to speak, of how do we talk to each other? How do you join? What are we asking of each other? And then I think the other thing in terms of holding space is that you really need to ensure that people who are a part of it are contributing in some way to the community in order to feel like truly bought in.

Anabel Lippincott Paksoy: So I’ll pause there because I can go on and on and on and on. But I think community at its core is like, it’s hard to design.

Maxine Minter: Yeah, I have so many threads. I mean, I love that baking versus cooking analogy, because it really does feel like those early communities and even huge scale thriving communities, there is almost like an organic system to them, kind of like a garden or something, that there’s like iterative and it’s kind of growing over time. And your work is that kind of curation as opposed to the construction of it and this kind of idea of creating the container for it. One of the things, especially in investing and especially in the precede seed and maybe even kind of further along, is building a community of people that are high signal, that send you interesting deals.

Maxine Minter: And so thinking about how do you construct that maybe more amorphous community that they might not share a kind of identity as a group. But how do you think about constructing that community of folks that send you really great deals? Do you thoughtfully construct it, or is it at this point something that just is your natural game?

Anabel Lippincott Paksoy: So I think the council, which is the, we used to call it like a consortium, essentially, it was a group of other women who were interested in investing as angel investors. And the goal of the council was just to get together and share deal flow. We did not invest as a group. There was no shared investment vehicle. It was not even like a formal entity. It was literally just a group of people who were sharing deal flow and talking through deals as like a learning exercise.

Maxine Minter: And it was amazing.

Anabel Lippincott Paksoy: Yeah, it was amazing. I think the reason I offered that context is because I think that, and it still exists today. Again, it’s a little bit larger in scale, but I think the reason I offer that context is because at the early days, when I was learning how to invest, I didn’t know how to invest, but I knew how to build a community, and I knew that I didn’t want to invest on my own. And so I was like, okay, let me build a community as a learning platform for myself.

Anabel Lippincott Paksoy: Now, I would say it’s a little bit building the kind of network, and you’re like, deal flow, flywheel, et cetera. That is more and more second nature to me. But it’s because of the muscle that I built through creating that more intentional group to share deal flow. The thing I want to say about that is it doesn’t mean you have to go off and create a group every time you want to cultivate your network and ignite it to be this powerful referral engine.

Anabel Lippincott Paksoy: I think the thing that I needed, and again, it’s interesting how trends have shifted, too. Even in 2018, it was like, which is five years ago at this point, it was a little bit new for operators, female operators who were not already super independently wealthy, to think about deploying capital as independent investors into startups. That’s not to say that people didn’t do it. They did. But part of the reason why I started the council was because it actually was just frustrating to me that the dudes around me were just talking about deals and sharing those deals with each other, and that that wasn’t a conversation topic in my peer group.

Anabel Lippincott Paksoy: I am here for girl talk. And again, I was like part of the assembly, which was like a women’s well being space. We were talking like, woo woO, astrology, birth control, should I be a parent? Am I going to rent the runway, which I’m a big believer in. But the point is we were having all those conversations, but for me it was like a yes. And I wanted to also talk about this other stuff that felt like I felt out of place asking my male counterparts. And so that is why the counsel, I just wanted to surround myself with those people. So I think if you find yourself in a place where you just have a little bit more confidence to talk about it with people, that’s the number one thing I would say around just putting, I’m a big believer in energy and just like putting the energy out there, like, I’m open to this.

Anabel Lippincott Paksoy: I want to talk about this. Send me your stuff. Just literally saying that in conversation and naming it is a big step towards cultivating that micro community around you 100%.

Cheryl Mack: That’s so interesting. I feel so many similarities between my experience just like a few years later that when I started angel investing, there was very few female angel investors in Australia in general. And the very few communities that existed were somewhat gated. And I really struggled to find other people that were willing to let me in and include me in the conversation when it came to angel investing. And so I started an angel group as well called three Six one angel Club.

Anabel Lippincott Paksoy: Cool.

Cheryl Mack: And that turned into a more formal community. But at the start, I really struggled. And so I hear so many similarities there and I love that. I hate that you experience the same thing, but it really resonates with me. And maybe you get this. One of the things that I get now that I’m somewhat experienced a few years down the road is that I often have new angels coming to me asking like, hey, how do I get involved in this angel thing?

Cheryl Mack: Where do I go? What do I do? And I’d love to. What’s your answer to that question? When people come to you and ask you that question, where do you direct them? What do you share with them? What are some of the first things that you make sure know?

Anabel Lippincott Paksoy: Yeah, great question. I think Maxine knows this. I’m a bit of a cynic, even though what I like to say is I like to bite the hand that feeds me in that. I often shit on startup land, even though that’s like my livelihood. But the point is that I think not dissimilar to the process. I’ve never converted to Judaism, but I know you’re supposed to be dissuaded a few times before you convert. I do like to remind people when they come to me asking, how should I angel invest that it’s inherently a very high risk asset class and should not be participated in unless you are aware of that and essentially willing to lose the money.

Anabel Lippincott Paksoy: The reason I bring that up is that I think that now as it becomes an increasingly trendier, I think people might think that it’s somehow a must or it is a way to flex professionally. And that all may be true, but it’s not the only way to do this. And so I think when people, I like helping people feel more comfortable angel investing, but I never want somebody to participate in the council or make an investment that does make them feel uncomfortable at their core. I’m okay if it’s like a little scary, but if they really are doing it for the wrong reasons. Air.

Anabel Lippincott Paksoy: Yeah. Because they feel like they must. That’s something that I think is important to vet right off the bat. So that’s definitely one of the first things I say. I know, Maxine, you and I have talked a little bit about this idea of angel investing can be treated almost like tuition, like a learning budget, right?

Maxine Minter: Yeah, absolutely.

Anabel Lippincott Paksoy: Insofar as the budget that you allocate towards investing, you can be prepared to lose it. And that’s okay if you are doing a lot of learning along the way. So I’m curious, do you still talk about that or do you guys think of it that way at all?

Maxine Minter: Oh, absolutely.

Cheryl Mack: Maxine gave them a name.

Anabel Lippincott Paksoy: Yeah, we call them learning checks. Nice.

Maxine Minter: Learning checks. Yeah, because I had this conversation two times yesterday and I’ve had it like maybe 50 plus times over the last month because so many people are, as you said, it’s getting trendy. More people are looking at angel investing as a way of building wealth, but also learning, getting access, et cetera. There’s a whole bunch of potential reasons that people are investing and I think normalizing that first probably year, maybe two, you’ve got so much learning to do to be able to actually confidently start to write those checks. And so being able to write the smallest possible check.

Maxine Minter: So maximal learning for minimal downside, I think is really crucial. I’m not sure if you’re aware, Anabel, but we actually, Cheryl started the angel list for Australia and it’s only a couple of years old. So to give you an idea of kind of ecosystem maturity in Australia, we are really new to this version. Like to having syndicates, this fractionalized access to angel investing. So it is almost universal in Australia that most of the people I meet, they think to be an angel investor, you need to deploy five hundred K per check as opposed to the 1000 $2,000 per check you can actually start angel investing in.

Maxine Minter: And so it is much more possible today to get a lot of learnings and do that kind of ten to 15 checks per year for a much lower entry price.

Anabel Lippincott Paksoy: Right.

Maxine Minter: So, yeah, it’s a very exciting time for the Australian ecosystem, but I think that’s right, like, normalizing this idea that this is a long term game you want to learn. And so thinking about what’s the best way you can learn from those early learning checks.

Anabel Lippincott Paksoy: Totally.

Maxine Minter: Yeah.

Cheryl Mack: Oh, I was going to say, to give you an example, like, Maxine’s learning check was 2500 and mine was 20K because you simply couldn’t invest less than that. When I started angel investing.

Anabel Lippincott Paksoy: Totally.

Maxine Minter: That’s a really interesting point.

Anabel Lippincott Paksoy: Yeah. I started out with a ten K check size.

Maxine Minter: Yeah. As a reflection, because at the time I started learning in the US and you started learning in Australia, and at the time in Australia, 20K would have been the absolute bare minimum, whereas I think that in the US you could get into, because of products like angel list, you could get in to deals at a much earlier stage. But I do think that that fact alone is one that not everyone knows in the US and almost no one knows in Australia. So one that’s definitely worth evangelizing a little more. So folks understand that they don’t have to be writing those huge checks to start off with and that they can be maximizing their learning.

Anabel Lippincott Paksoy: Totally. I think one other thing that we found at the council is that we had a lot of people who, one of the reasons they wanted to get involved in angel investing was actually to contribute to the founder’s journey. And that was actually something that I think was pretty universal as like a why for folks, which is that they didn’t just want to write the check, though. There were some of those folks, and we need those people too. Right.

Anabel Lippincott Paksoy: Not every founder wants all their investors to be, like, weighing in at all times. But the point is that I think, I like to remind people that your check, I used to say my checks are small but mighty. Right. Insofar as I might be deploying a small check, but it comes with me and a lot of my effort. And you can also sell yourself as an advisor who wants to put your money in alongside of their time. And I think that was something that in the early days of the council, when we were getting women comfortable with just getting involved, deploying capital and actually pitching themselves to a founder, which I think as an investor, you have to start getting good at that.

Anabel Lippincott Paksoy: I think pitching themselves as investor plus or advisor who’s going to put some money in. And I think that is a really good way to put small checks in because you could essentially say like, look, I’m putting in five K or less, right. But I’m going to give you time on my time as well. And I’ve actually even suggested and for myself asked for, hey, I’m going to give you ten K, but I want twenty K of equity. Right. Because I’m going to give you my woman power alongside of that. And so that’s a good way to kind of amplify the actual dollars, I think, in the early days as well.

Maxine Minter: Yeah, absolutely. And I’ve seen a few folks do that actually. Dustin, who is your partner at 43, was our first precede investor at Fairshake.

Anabel Lippincott Paksoy: Yes.

Maxine Minter: And he did a very similar thing, right?

Anabel Lippincott Paksoy: Yes.

Maxine Minter: He wrote the check and also negotiated advisor of equity on top of that. And like, man, did he earn that equity. He was so useful and such a wonderful partner to us as we were building the business. So I think it can be a really, really powerful model. One thing that jumps out to me here is we’re talking about this and when I think about you, you’re just always kind of the right step ahead of the curve, right? You’re not so far out ahead in trends that you build things before that you build things and then they wither on the vine. But I mean, just the angel investing example, the kind of community building example, you’re just the right amount kind of ahead. I wonder, and this is maybe purely selfish, but what cool things are you seeing in terms of innovation in the angel investing space, innovation in the fund structuring space, innovation in the investing world generally. Have you seen anything cool recently?

Anabel Lippincott Paksoy: Yeah, I mean, I think I’ll have to talk a little bit about my current project.

Maxine Minter: Yes, please.

Anabel Lippincott Paksoy: Which is 43. It’s a pre product fund. Dustin, the investor that Maxine was just referencing is my partner in the fund and Maxine was our matchmaker. So major props to that. What I mean by talking about my current project is I think that as I was kind of happily kind of bopping along as angel investor, I didn’t actually envision professionalizing. And by that I meant like I just deploying other people’s capital did not feel like it was really something that I would want. And a part of that is because I think there’s a lot of autonomy and power in making decisions on your own.

Anabel Lippincott Paksoy: And the idea of having to kind of go and join a firm with a thesis that’s not yours. And have this idea of consensus based partner decision making was just not appealing to me. That being said, it takes money to make money. And so it’s hard to imagine becoming, having this be like a real financial positive outcome when you’re deploying a total of $100,000 across years, right?

Maxine Minter: Absolutely.

Anabel Lippincott Paksoy: And so I think that one of the things that we’re doing at 43 that I do think is really impactful for the space, and I think the space needs it, is this idea of professionalizing the angel check. And what that means is staying independent, as in staying kind of as a conviction based decision maker and capitalizing angels. Now, I think that idea is not new. It’s been around for a while in the US. And this idea of things like Scout programs, which are where funds offer small budgets to well connected folks for a lot of really different reasons.

Anabel Lippincott Paksoy: And angel list itself kind of started a program around this. But I think the thing that we’re working on now is this idea of actually wanting to think about becoming a relatively, like full time angel investor. So not somebody who is doing something on the side, but actually honing it as a craft, as a professional skill set. And when I say that, I mean someone who’s really in the weeds at the individual level, in the company building work as an investor.

Anabel Lippincott Paksoy: And that is, I think what the term angel originally kind of means is this idea of somebody who’s taking a bet on you, who is out in the wilderness of social proof no one else is like, there’s not a ton of signal here. They are writing a check for you early and they are along the ride with you. And they’re not your board member, they’re the call before the board member call. Right. And so we are currently raising a fund against this thesis, this idea that we should be able to capitalize full time professional angel investors.

Anabel Lippincott Paksoy: And that idea of really giving that craft itself the time, space, and money to become a financially viable solution is kind of this idea.

Maxine Minter: Yes. I am so there for this idea of being out there in the wilderness of social proof. I hope you don’t mind. I’m just going to steal that terminology. It is just incredible, because I do think that that is what precede is supposed to be. Right. The very, very early stuff. What I think of as American style precede is kind of out there in the wilderness prior to social proof. And I meet a lot of companies in Australia where they are very much in the social proof now, and they’re still kind of being considered pre-seed companies but they have a product, they have early traction, they have early customers, et cetera. And to me, I think we are really missing in Australia that true professionalized group of people that are doing that kind of true out there in the wilderness prior to social proof, or at least we were missing that. And hopefully coventures can deliver on that promise to founders. But I shouldn’t say there’s no one there. I’m out there.

Cheryl Mack: I was going to say you’re there.

Maxine Minter: Yeah. And there’s kind of a handful of angels that are willing to do that work, and there’s a handful of people that do it.

Cheryl Mack: And I think part of it has been that we are traditionally more risk averse, but part of it is also just like most founders here, I think, are less willing to put up their hand and say, hey, I’m working on this until it gets to that social proof. So I’d be curious to see, or I guess ask, how do you go about finding them? Are you searching in the wilderness for these companies or are they just more open about it in the US?

Anabel Lippincott Paksoy: I don’t know the comparison, Maxine, you probably have to speak to that. I think that I would say, yes, there is a lot even, there’s been this natural downturn in the market. Right. I know we’ve all experienced that globally, so in the very recent past. But I would say especially, I keep referring to startup land, I think, I mean, really like the kind of Bay Area and the coastal communities of kind of tech dominated workforce and kind of millennial Gen Z folks, mostly.

Anabel Lippincott Paksoy: The idea of being a founder and working and hacking on your startup is definitely, I would say, making its way to the mainstream to the point where people are doing that, talking about that a lot. I do think that a lot of people never kind of get off the ground with those ideas, and that is not because there isn’t a lot of money available to those people right now for what we’re talking about. Right where yes, precede may be earlier in the US than it is in Australia, but even know funds and professional investing has been shifting later and later, which is why we’re talking about the white space of the early days right now.

Anabel Lippincott Paksoy: One of the things that I think is important to me, I don’t have a mandate personally to seek a certain profile founder demographically, but I find that you find a lot more different types of founders when you’re willing to write an early check, because otherwise you are only really able to invest in founders who can afford, for lack of a better term, to float themselves while they build their company or are building their companies while working full time, which is just not like the velocity that you typically want to see.

Anabel Lippincott Paksoy: And so I think that is part of why I like this stage, is that the goal of my check is to allow the founder to go full time on their idea and amass their founding team and set up their first kind of learning experiment. And that’s pretty much it. And so you really are kind of living on a prayer at that point. Like, we’re talking very early the checks that I’m writing, and I think that gives me a lot of freedom to leverage my background in people operations as my core decision making framework. I like to joke that I would not make a great professional growth investor because I’m not a finance person, but I think I make a pretty good founder oriented, founder selection investor. Which is really what you’re talking about when you’re talking about the earliest of stages.

Maxine Minter: Absolutely. I mean, I think your background in the people space, you see it being such a core strength in the wonderful investments you make and the kind of founders that you find. And I think there’s probably a thread there from your community days as well, like your ability to find amazing folks, vet them really well, and then invest at that super early stage. So could you say more about what you look for?

Maxine Minter: What are the kind of founders that you are when you meet them? You’re just like, heck, yes. I’m so excited to kind of back you to make this first step out of your full-time job or full-time into this idea.

Anabel Lippincott Paksoy: Yeah, I learned, actually, the concept of a decision diary is not new. This is this idea where you kind of proverbially journal as you make your decision. But I do have to give props to Maxine as one of the most thorough decision diaries and great frameworks that I. And you also were kind of like a notion evangelist. So it was like, in notion, which felt fancy at the time because there was like, toggles and stuff. Anyways, the point is that, of course there is.

Anabel Lippincott Paksoy: Yes, exactly. So I would say that I’ve honed the formality of this over time as I’ve professionalized. So I want to say, I think before we dive into this decision making thing, I just want to name, this is another area that we see early investors get nervous about, which is, how do I build conviction, and actually, how do I know? And I’ll talk a little bit about how there’s, like, a gut feeling and whatever.

Anabel Lippincott Paksoy: And again, I want to say angel investing is highly risky, and so there is going to be a moment where you just jump off the deep end. And so that’s a little bit why thinking why those learning checks, giving yourself permission there and stuff. At a certain point you’re never going to get to. If everyone knew what was going to be great from the beginning, there wouldn’t be such a thing as this whole space, 100%. So I just want to suggest that there is always going to be a lot of unknowns when you invest, especially early stage.

Anabel Lippincott Paksoy: But I think for me, the things that I know that I look for in people. Yeah, as you said, I wouldn’t surrounding myself with people. And the things that I look for in founders when I think about supporting them is some kind of deep, deep, deep, deep. Why that they’re doing what they’re doing. And I read a business case about how HR tech is the next big space is not what I’m talking about. Right. But like, oh, yeah, I grew up around my family business, which was this.

Anabel Lippincott Paksoy: Since the first job I had, I noticed that there was these customers that we were servicing and they were missing this big thing in their life that could really make it better. Or I’ve been validating this hypothesis from within my operational roles for a long, long time, or my child is experiencing this thing and I need to whatever, right? So I need a deeply personal and deeply authentic for. I know that’s like authenticity, but I need a deep why that really is defendable to the person.

Anabel Lippincott Paksoy: Because I think that being a founder is not that fun when a kabush comes to shove. And so they need to have a purpose driven reason that they’re solving this problem. And to that end, I think, obviously, grit and resilience are really critical. And I think what I want to see around vetting that is, are they super married to the idea of how they’re going to solve the problem, or can I see that they would pivot? Because I think the idea of pivoting is actually, I love a pivot.

Anabel Lippincott Paksoy: I think it shows that you are building a rapid learning engine. And the last thing I’d say is something that I like to call followership. I think ultimately, to be a founder, you have to be a leader in some way, shape or form. And leadership can have a lot of different flavors, but people need to follow you again into this wilderness. Right? Because startups are like that, too. And so I want to feel that conviction, and there’s no way to vet that. That’s where it gets super personal.

Anabel Lippincott Paksoy: What I like to say is, could I fall in love with this founder, and I don’t mean romantically. I mean, would I actually go work for them? Is this person going to be able to attract top talent and investors around them? And do they have that thing that you can’t really put your finger on the pulse of? That is their kind of leadership, and that’s something that I call followership. And so those are like the core kind of founder selection tools.

Anabel Lippincott Paksoy: The other thing I always say is, can I explain the business model to my husband? Depends. What does your husband do? Right? No, he’s like a pretty nerdy engineer who is relatively risk averse. So it’s helpful to me to, like, I don’t need to deeply understand the space as much as the founder does, but I do need to be able to at least explain it to somebody who’s going to ask me tough follow up questions.

Anabel Lippincott Paksoy: I want to understand it. I don’t need to go diligencing everybody I know who’s in that space. I need to at least be able to really feel confident and able to explain it. So those are some of my kind of decision diary points.

Maxine Minter: I love that.

Anabel Lippincott Paksoy: Oh, I love those.

Cheryl Mack: I’m so curious. How much time do you spend with a founder to get to that stage in order to determine whether they have the followership, have the deep ‘why’?

Anabel Lippincott Paksoy: Yeah, I would say, shockingly, not that long. So I would say always a 30 minutes meeting at the start just to be like, is this at all, like someone that I want to keep talking to? Kind of like a first drink date, so to speak. And then the second date. The second meeting is like an hour long. Tell me your life story. And I mean that literally. I’ll be like, so where were you born? Then what happened?

Anabel Lippincott Paksoy: Then what happened? Like a real deep dive into who they are. And if they have a co-founder, then I want to meet that co-founder and understand the same things and also want to understand their relationship pretty carefully. So that will often be like a follow-up conversation. And then I usually have a third conversation around the actual experiments that they’re planning on running. So obviously the traction that they might have or have not. But then what are they doing?

Anabel Lippincott Paksoy: What are they going to do with the money, essentially, what are they actually planning on doing? I’m not talking about what’s their big vision? It’s great to hear that, but what does your next three months look like? What are your next twelve months look like?

Cheryl Mack: Very cool, very interesting.

Maxine Minter: It never ceases to amaze me, because I think the way that you think about precede investing and the way that you think about kind of backing that early founder, I haven’t found anyone in Australia who speaks about it in the same way. And that was my experience living in the Bay or still living in the bay. The willingness to really go to the human level as opposed to try to manufacture some investment case on a business model that is so far from being built yet, it’s really refreshing to hear and be reminded how important that first human evaluation is. That kind of who are they as people? Where do they come from? What does their story tell you about their likely trajectory from here?

Maxine Minter: And you are obviously one of the best people in the world to make that evaluation, right? Like you come from that people background and have a wonderful instinct and a honed instinct over time of picking really wonderful people for chasing really hard problems. And it’s so obvious in the kind of way that you’ve built 43. It’s super, super cool. So when you think about where you’re excited about stage, I mean like industry wise, do you develop theses about we think there’s going to be some interesting stuff in this space, or we want to see a change in this world, or do you just totally focus on the founder?

Anabel Lippincott Paksoy: I have started to see some patterns in my own investing, but it’s almost like I was about to say chicken or egg, but that doesn’t apply because that means we don’t know which came first. But I would say that I’m starting to kind of retroactively pattern match a little bit. And so I think what I mean by that is I’m drawn towards people who are really been in the guts of companies and problems that are very unsexy and understand that they want to bring SaaS innovation to it, essentially.

Anabel Lippincott Paksoy: Right. So we’re talking real estate, freight, shipping, supply chain, acquisition of building materials. And that’s definitely one part of it. The other thing that I find myself drawn towards is people who are trying to solve problems for niche communities. So I think that’s another thing that probably fires a little bit of my background. But a couple projects that I’m excited about right now are people trying to solve problems for podcasters or trying to solve problems for micro influencers, meaning folks that have a followership naturally, and people want to transact within that group.

Anabel Lippincott Paksoy: And so helping them kind of facilitate transactions within their micro community. Folks who are a part of the freelancing community and they want to solve problems for the freelancing community, things like that. So I would say that those are all broadly different spaces. Those are going to be different approaches and different business models, but I find myself thinking about why they’re attracted to the problem and whether or not the problem itself is something that I think is how they’ve made a decision. That this is a problem is kind of what I’m saying. So, yeah, I guess that what that means is I’m not opposed to investing in Web three, which crypto and stuff. I’m not opposed to investing in AI, but I’m not going to go at my sourcing with that constraint and filter. It’s going to be potentially businesses leveraging those technologies to solve a different problem.

Maxine Minter: So cool. I mean, I just feel like I could chat to you all day, always.

Anabel Lippincott Paksoy: Yeah.

Maxine Minter: And every time we chat, I just feel like I leave. Just totally inspired.

Anabel Lippincott Paksoy: That’s so generous.

Maxine Minter: I will say I have been so inspired by your constantly inspired by your bravery and your ability to kind of see trends early and front run. So I’m super excited to ask you our standard closing question for these conversations, which is, yes. What is your biggest big cajones moment? A moment that you have done something.

Anabel Lippincott Paksoy: Really brave, probably like becoming a parent.

Maxine Minter: Fair.

Anabel Lippincott Paksoy: But I think related to what we’re talking about right now, I think writing that first check, honestly, that’s a big thing. And essentially doing that with all the conviction in the world that I want this product to exist and I’m okay if it doesn’t, meaning I’m okay if it doesn’t work out, but I want to be along for the ride. And spoiler alert, that investment has gone to zero, and I don’t regret it.

Anabel Lippincott Paksoy: That’s such a great thing to hear, thoUgh. I feel like as a first check.

Cheryl Mack: Writer as well, also, this is the first check podcast. I don’t know if Maxine mentioned, but to, to have someone come on here and say that they absolutely do not regret in any way, shape, or form their very first check that they wrote is really great.

Maxine Minter: Yeah, that’s the best.

Anabel Lippincott Paksoy: Yeah. No, and again, I lost all the money. Just to reiterate, just to be super clear, you lost the money. Got it. Duly noted. Yeah, exactly. Well, thank you so much, guys. This was really fun and exciting what you guys are doing with this space. And I giggle every time I read first check with the Q Ue. I’m always like, I love that.

Maxine Minter: That’s amazing. I love it.

Anabel Lippincott Paksoy: I’m always like, oh.

Maxine Minter: Thank you so much for joining us today. And as always, this has been such a pleasure. Thank you.

Anabel Lippincott Paksoy: Thank you, Anabel. Yeah, talk to you. Bye, guys.

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