Angel Investing: On-Ramps, Communities, and Maximizing Learning

First Cheque

On-Ramps, Communities and Maximizing Learning

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In this episode, Maxine Minter and Cheryl Mack discuss their journeys into angel investing and share valuable insights for aspiring investors. They highlight the importance of community and learning in the early stages of angel investing and provide guidance on different investment strategies. Maxine and Cheryl also emphasize the need for diversity in the investor landscape and discuss the changing dynamics of the startup ecosystem. They address common misconceptions about angel investing and offer practical advice for those looking to get started in the field.

Key topics discussed in this episode include the different paths to angel investing, the role of education and community in learning about investing, the significance of diversity in the investor landscape, and the challenges and rewards of angel investing.

Key Takeaways

  • Angel investing can be approached through various paths, including direct investments, syndicates, and investing in funds. Each approach offers unique benefits and learning opportunities.
  • Building a strong community of fellow investors is crucial for learning and making informed investment decisions. Angel groups and syndicates provide valuable platforms for collaboration and knowledge sharing.
  • Diversity in the investor landscape is essential for supporting underrepresented founders and driving innovation. Investors should actively seek out opportunities to invest in diverse founders and contribute to a more inclusive startup ecosystem.
  • Angel investing requires a willingness to take risks and a long-term perspective. It is important to be prepared for potential losses and understand that returns may take time to materialize.
  • Continuous learning and staying informed about the latest trends and developments in the startup ecosystem are key to becoming a successful angel investor.


  • “There is nothing more powerful than being the ‘dumbest’ person in the room. Give yourself permission to ask all the ‘stupid’ questions and learn as much as possible.” – Maxine Minter
  • “Investing in startups is a riskier asset class, and it’s important to have a stomach for potential losses. But it also offers the potential for outsized returns and the opportunity to support innovative companies.” – Cheryl Mack


  • The Council: An organisation mentioned by Maxine Minter, formed by a group of friends from a coworking space who started an angel investing group. It has scaled into a larger organisation now.
  • Zeta: The first company Maxine Minter invested in. It’s led by a founder named Aditi.
  • Aussie Angels: Mentioned as a platform for angel investing in various identity groups.
  • University Programs on Angel Investing:
    • UQ (University of Queensland) has an angel investing program.
    • UNSW (University of New South Wales) offers an angel investor course.
    • Wade Institute runs the VC Catalyst course.
    • Southern Angels in SA (South Australia) is reportedly working with the University of South Australia on a similar program.
  • First Believers and Explorers Program: Both Cheryl Mack and Maxine Minter mention participating in this program.
  • Startmate: Cheryl Mack mentions being a mentor at Startmate, which is part of Blackbird. It runs a program called First Believers for Angels.
  • Books on Angel Investing:
  • Flying Fox Ventures (formerly Eleanor Venture): Mentioned by Cheryl Mack in the context of syndicates providing insights into their investment decisions.
  • Afterworks: An organization that hosts community calls for angel investing.
  • ASX (Australian Securities Exchange): Discussed in the context of investment trends and data.


00:00:00 – Introduction to the show First Cheque.
00:01:09 – Maxine’s journey into angel investing.
00:02:53 – Cheryl’s accidental entry into angel investing.
00:05:00 – The importance of community in angel investing.
00:07:45 – The lack of diversity in angel investing.
00:08:49 – The growth of inclusive communities and educational programs.
00:09:47 – The impact of funds in promoting education and community.
00:10:33 – Final thoughts and advice for aspiring angel investors.
00:10:33 – Introduction to angel investing and different on-ramps.
00:11:38 – Different ways to invest in startups: direct, syndicates, and funds.
00:12:58 – Investing in funds with smaller minimum investments.
00:13:46 – Making a case for smaller investments in funds.
00:14:30 – Prediction of more micro funds in the future.
00:15:04 – Importance of maximizing learning in early investments.
00:16:01 – Different reasons for angel investing: future VC, impact, subject matter expertise, skill application, and making money.
00:17:11 – Diversifying and creating a higher return profile.
00:17:50 – Lack of representation of women and underrepresented groups in angel investing.
00:18:49 – Opening doors for people outside the ecosystem.
00:20:23 – Tailoring on-ramps based on investment goals.
00:20:36 – Importance of being a door opener and creating an inviting community.
00:21:42 – Maxine Minter discusses the availability of angel groups, syndicates, and niche funds for investing.
00:22:03 – Cheryl Mack highlights the value of syndicates for learning and gaining perspective on investment decisions.
00:22:18 – Maxine Minter suggests considering angel groups as a valuable way to learn and collaborate.
00:23:18 – Cheryl Mack emphasizes the collaborative nature of angel groups and the insights gained from discussions.
00:23:31 – Maxine Minter agrees and highlights the importance of expressing opinions and learning from others.
00:24:23 – Cheryl Mack reflects on the value of joining angel calls and participating in community evaluations.
00:25:19 – Maxine Minter encourages being open and vulnerable to ask questions and learn during the early stages of investing.
00:27:03 – Cheryl Mack shares her experience of expressing opinions and the positive outcomes it can lead to.
00:27:23 – Maxine Minter recalls advice from a mentor about the power of being the least experienced person in the room.
00:29:38 – Maxine Minter and Cheryl Mack discuss the need for lawyers and accountants in early-stage investing.
00:30:01 – Maxine Minter encourages learning by reviewing investment documents and seeking understanding.
00:31:23 – Cheryl Mack suggests reading “Angel” by Jason Calacanis and “Venture Deals” by Brad Feld for angel investing insights.
00:32:03 – Maxine Minter and Cheryl Mack consider the possibility of writing a new angel investing book.
00:31:48 – Cheryl and Maxine discuss writing an angel investing book.
00:32:06 – Maxine shares a story about receiving a shirt that didn’t fit.
00:33:13 – Cheryl talks about the challenges and risks of angel investing.
00:34:44 – Maxine explains the “j curve” and the psychology of investing.
00:35:29 – Cheryl discusses the decision to continue or stop angel investing.
00:37:15 – Maxine advises allocating money comfortable to never see again.
00:38:28 – Cheryl encourages exploring other asset classes if angel investing is not for you.


This transcript has been A.I. generated.

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 was like nine or 10 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? Yeah,

Cheryl Mack: 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? Why

Maxine Minter: 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 before I because I feel like this is Going to happen again 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.

Cheryl Mack: 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. Um, but one of the things that I didn’t find, I, 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.

Cheryl Mack: 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, um, 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. 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.

Cheryl Mack: 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, um, 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.

Maxine Minter: Right? There’s just like default assumed. I had no idea what I was talking about. 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. But I think, yeah, like. You and I have very different experiences. I’m so glad you got that. The cool thing I think now is that, you know, five years on from when I started, there are so many communities that are much more inclusive, much more open, and focused on education now.

Cheryl Mack: What I think is really cool in the last couple years, Three, three universities that I know of in Australia have launched their own like angel investing program. So UQ in Queensland’s got one um, UNSW has the angel investor course and um, Wade Institute has the VC catalyst course. So like we’ve gone from zero when I started to three Um, educational, education institutions, um, and I, I believe that, uh, Southern Angels in SA is working with, I think, University of, uh, South Australia to come up with one as well, so, like, there are places, and, and the fact that, like, you know, you got a lot of education from Stanford, which may or may not have been a marketing ploy, um, but, the, the fact that education, institutional education, um, is now, coming into the, in the space, I think is really cool.

Cheryl Mack: So if you’re out there and you’re looking for something like that is what happened to you.

Maxine Minter: Yeah, exactly. I mean, I also think that there’s some really exciting. Yeah. Right. The funds are starting to run their own education program. Not least of which the Explorer program, of which both you and I were the first cohort and which is how we met.

Maxine Minter: Yes. That is how we met. Even though now you’ve started this like narrative that you forced me to stay or like what big part of me staying and, but like, that, that is how we met. And I think it was a big part of me being like, wow, there’s so much cool stuff happening in this ecosystem, you know, because Cheryl is here mainly.

Maxine Minter: Right. Right. Right. Right. Right. Right. Right. Right. Right. Right. Yeah, obviously.

Cheryl Mack: Yeah, we did meet at First Believers and then the other one is we met, uh, where we continued to meet. At the Explorer

Maxine Minter: program.

Cheryl Mack: Sorry, the other way around. You and I met at Explorers and then we continued our journey, uh, as mentors at Startmate together and so I got like this double magazine exposure right from the get go and I, and so Startmate also runs a program called First Believers for Angels as well, which is Part of, you know, StarMates, part of Blackbird.

Cheryl Mack: So yeah, the funds are doing some great stuff. I’d love to see more

Maxine Minter: of that. Right. Absolutely. So I think for those folks that are listening today, that are like looking for their on ramp onto angel investing, you know, you’ve got these education programs, you’ve got these like more structured programs coming out of the funds.

Maxine Minter: Anything else that you think that they should know about? To start thinking about angel investing.

Cheryl Mack: Yeah I think one of the things that felt really confusing to me when I first started was this idea of like how do I actually write a check and Like, do I just hand the founder cash in a baggie? Like, what, how does this actually happen?

Cheryl Mack: And, like, it’s one of those things where, like, you just don’t know until you actually do it, and, and when you are doing it, you’re not sure if you’re doing it the right way, because you don’t, you never get told. So, what I wish I knew at the start was, like, there are different ways to write checks to startups.

Cheryl Mack: One is you can literally, like, just talk to a founder and decide, Hey, I’m gonna give you money, and I’m gonna wire you money to your, like, company account, and you’re gonna give me a piece of paper that says I own some shares in your company. And that’s all it is. I kind of, I’m not sure what I thought or what I was expecting, but, like, that process just, sometimes it, Like, I think at the start it felt too easy, it was like, are you sure, I just, I just send you money and you give me this piece of paper?

Cheryl Mack: But then the other way is like, you can go through syndicates and in that way, in, rather than like having that direct relationship with the founder, you kind of rely on somebody who’s done it before. And it’s. Yeah. Yeah. Rather than sending the founder directly money, you send like the syndicate lead, or whatever platform they’re using, you send them the money and they deploy it to the startup.

Cheryl Mack: So there’s a little bit more structure involved there. And then the other way is like you can just, if you really want to get into early stage investing, maybe not necessarily like be an angel investor right away, but kind of learn, um, a little bit along the way, you can just like write a check to a fund and say, all right, you distribute my money into this early stage space.

Cheryl Mack: So I kind of. think of them as like three buckets. You can go direct, you can invest through a syndicate, which is kind of this like happy medium, in my view, between the fund and direct. Um, or you can just go with a fund and have a fund invest your money.

Maxine Minter: Yeah. I actually, one of the things that I have been noticing recently, which is a myth I’d like to bust, is that I’ve noticed a lot of similar myths of like, you have to be extremely wealthy to invest in funds.

Maxine Minter: And I think that that’s not accurate. Um, you know, especially if you can be value additive to the fund, there are, I have seen, in fact, in our own fund, there are folks that have invested for as little as 10, 000. And so I think permission here for our listeners to like, also, if you meet a fund and you’re like the fund manager is really cool and I want an opportunity to like support them, like make a case for it in the same way that you would pitch a startup and like see if they will allow an investment for a smaller minimum.

Maxine Minter: Yes. That is

Cheryl Mack: such a good, like, point to make. I have a story because one of the things that I, like, was just mind blown on was I met someone named Michael Langford. He’s the head of, um, Google Cloud for startups. And he was like Last March. Yeah. He was like, I made a resume for the fund to take my money. So he, like, made a one pager of, like, here’s why you should take my money.

Cheryl Mack: And Like submitted that to them and because it was less than the minimum, obviously, uh, and I thought that was really freaking cool. I was like, that’s like, how do you, how do you get into a fund if the minimum’s 250? And I can’t remember exactly what he wrote, but it was significantly less than that. And he did it just by pitching them and saying, hey, this is why you should take my money.

Cheryl Mack: Right. In the form of a resume.

Maxine Minter: Yeah. I love that. I love that. Yeah. I mean like I have invested in some LP, sorry, in some funds in the US. For like 10k for similar reasons. I didn’t have the foresight or ingenuity as Mike did to like write a resume, but like pitching them in the same way I got into kind of early, yeah, like early startups is like telling them the story of like how I want to help.

Maxine Minter: And like, obviously following through on that as well. I think it’s a really valuable thing to think about. I also think in Australia, My hot take is over the next couple of years, we’re going to see lots more micro funds. And so, from that, you will also see, like, a greater ability to participate at the LP level.

Maxine Minter: But I do think, I mean, something that you and I have a Actually, at this point, it’s like a soapbox moment, right? Like, we’re constantly evangelizing this concept of, like, maximal learning for your early checks. Like, really optimize for learning as much as possible on those early checks. Like, you just will be a noob.

Maxine Minter: probably for your first 10 investments. And the goal is to like minimize noob status as fast as possible, which like minimize noob status, right? Small learning checks, right? Yeah, exactly. Right. Small learning checks and also put infrastructure in place to like learn. a maximal amount for those learning checks.

Maxine Minter: So thinking about like, you know, if you decide to invest in syndicates, if you decide to invest direct, if you decide to invest in funds, like, what are you learning? How are you extracting information from that experience to help you be a better investor over time? I actually think that there’s a Another thread that I’d really love to pull here, which is that people angel invest for very different reasons.

Maxine Minter: Yes. Actually spending some time thinking about why you’re angel investing so that you can construct your learning and your angel investing journey appropriately. So what I’ve observed is there’s kind of a handful of buckets that people are angel investing. To achieve, one is they want to be a VC one day.

Maxine Minter: Two is they want to see an impact in the ecosystem and kind of put their dollars behind that happening. Three is that they are a subject matter expert or they have a kind of particular interest in an area and are looking to invest to learn more. and or participate in a trend that they’re seeing and or like apply their skill.

Maxine Minter: The version of this that I actually have seen that I think is really interesting is there’s folks like actually from Notion and like operators who are investing behind companies that is like operationally interesting so that they’re constantly keeping their skills fresh, right? It’s like obvious that people do that on the design front and the product front and the engineering front, but it’s just as prevalent, I have seen in the like other functions of the business, which I think is really cool.

Cheryl Mack: Yeah. You forgot the main one though. Like

Maxine Minter: Making money? Make money! Oh, that’s great! Make money?

Cheryl Mack: Like, I think there’s also a world in which, like, if you have a large portfolio of, let’s say, safe or, like, relatively safe assets, right? You’ve got a whole bunch of ETFs and just, like, index funds and maybe you bought a house.

Cheryl Mack: And it like, where do you go from there, right? Do you then just start buying individual stocks? Super volatile, just as risky, arguably. Or do you take a look at like, how do I diversify and create a, a portfolio of assets that have the potential to create a really outsized return? Um, and I, I think that like, alone can be a good motivator, right?

Cheryl Mack: You’ve A hundred percent. Most people don’t tend to dabble in this space, but if that is something that you’re interested in, it can just be like, look, I need to, I want to create a higher return profile for some of my

Maxine Minter: investments. Right. Yeah. I mean, like, that is the reason that most people I meet want to be an angel investor.

Maxine Minter: That’s hilarious. I also, I mean, like Something I will name, yeah, is, I have met so many people who are just holding a bunch of cash. Yeah. Which in this market makes me very sad, and I will say that that group of people like trans female, and that is a real shame.

Cheryl Mack: But I think that’s because they don’t know what the options are.

Cheryl Mack: And once you, once you kind of tapped out, like, alright, well I’ve, in, I’ve put a bunch of money in, like, real estate, and I’ve put a bunch of money in, like, these safer, Investments and it’s like well now the rest of it is just either sitting in my offset account or like sitting somewhere that you know, what do we do with right?

Cheryl Mack: And, and I meet people like that all the time who haven’t, who don’t know, and if they do know that they want AngelBest, they just don’t know how to get started. Hence today’s call.

Maxine Minter: Session. Right, right. Yeah. Well, I mean, the other thing that I have seen, I looked at some data from the ASX recently to see how different demographics are investing.

Maxine Minter: And interestingly, a lot of women, they reference, well, they kind of seek out friends and family. as advice on investing. If we think of the demographics that have exposure to startups, both in terms of an operating and investing, I think that puts us at it. They trend male. They trend male. Yeah. So there’s like a clear, there is one reason I think that.

Maxine Minter: And I think that we see less of the participation in allocators as women. And I think near the last stats I saw, 2 percent of capital is deployed by women globally in startups and in venture, which is sad, you know, a real challenge. If you think about the like nature of the products that are being built and those kinds of things, like not having representation at the funding level is a real challenge.

Maxine Minter: If you are looking to fund companies that, you know, serve female demographics and the same applies to other. areas of underrepresentation in the demographics of funders, right? I don’t know what the numbers are off the top of my head, but the kind of demographic of people that come from other underrepresented backgrounds, people of color, rural backgrounds, veterans, those kinds of things.

Maxine Minter: Like we don’t have, especially in Australia, but all over the world, like we just don’t have a wide diversity of perspectives around the funding table yet. Yet.

Cheryl Mack: Yet. Is the Alfredo word. Yes. Yet. And I think that’s important, right? Like, we need to think about, uh, what our future is going to look like as a startup ecosystem.

Cheryl Mack: Yeah. And how diversity around the allocators table is going to create that. And I think for us, and like, part of the reason we’re doing this podcast is to change the stats on that. Not that that’s going to solve all the problems, but I do think that it’s one step in the right direction. A hundred percent.

Cheryl Mack: Yeah. So. If you are somebody who is, like, not from this world, right, like, you and I kind of grew up in this world. Uh, and we’re super lucky to have done so, but what are the ways that we can create better, like, open doors? We’ve talked a lot about on ramps, but, like, how can we better open the doors for people who are not in this ecosystem and make it more inviting for them to come in and have a look around and, like, join a community now that they all exist?

Cheryl Mack: Yeah, yeah.

Maxine Minter: Well, actually, I am, like, Loving this theme I’m hearing across our ecosystem of people self identifying as a door opener. Mmm. Like I just, I’m there for, for this. It’s so good to see. Because I think this is how that, how change happens. So if I, kind of with that theme, maybe bringing us back to these on ramps, for all of those reasons that one might invest, it then changes the on ramp we might want to use.

Maxine Minter: So for example, if you want to make money and be a VC in the future, you know, investing directly is really valuable because it’s showing that you have deal flow, that you can win deals, that you can kind of get to conviction, get to conviction, you’re learning about your own decision making process, et cetera.

Maxine Minter: I think it’s really valuable then to do things like invest in other funds and invest via. syndicates to watch how other fund managers are doing that. It’s an early on round to that so you can hone your skill. If you’re investing for say, impact or investing to kind of change the demographics in a particular area, you know, then you’re wanting to see as many deals as possible with a particular feature to them.

Maxine Minter: So thinking about kind of where can you find those kinds of companies? How might you meet them? There are angel groups to do that. There are syndicates to do that. Maybe there are funds. that do that. I mean, in Australia, we have a pretty homogenous fund group so far, right? There’s like, not a lot of niche funds because of the nature of our macro, but I think, like, it’s worthwhile thinking about, like, where you might find people of that group.

Maxine Minter: True. And then there is, like, the group of us that are looking to invest. I won’t say us, I don’t do this anymore, but, like, looking to invest to, like, hone your skill set on something. Again, thinking about, like, how do you build your funnel so that you can learn maximally? I actually think that, like, syndicates and fund investing is a great way to do that because you get Their perspective, but you probably also want to do some direct.

Cheryl Mack: Yeah, I think syndicates are a really great on ramp for learning in general And of course, I’m biased. I run a syndicate So there’s that but if you think about like You know, funds aren’t sharing their investment committee papers about why they’re investing in a company, but a syndicate, when they show you a deal, they’re sharing their notes on why they’re investing in this company.

Cheryl Mack: Yeah, and I’ve personally, when I started, I signed up to a couple of syndicates and reading the notes on why somebody else was investing, and I think the first couple that I got were actually from Kylie Fraser at what was at the time. Eleanor Venture now is Flying Fox. Just being able to read. And like kind of almost get in her head about like why she was investing in something was pretty freaking cool and That piece I think is something that it just is so much more available now Like there are there are so many more syndicates you can join now than when I started There’s a number on Aussie angels even some like focused ones like niche focused ones, right?

Cheryl Mack: Like if you’re looking for okay, well, I really like climate tech and we’ve got three climate tech ones on there That’s the kind of thing that, like, you just wouldn’t have had access to now. So, if you’re looking for a particular niche or to learn, like, joining a syndicate is one of the, I think, one of the most effective ways of doing that.

Maxine Minter: 100%. I also, I also think that angel groups are a really valuable way to do this as well. Yeah. That’s very collaborative. Right. It’s very collaborative and there’s a lot of stuff that you can, you can’t put in a deal note from a regs perspective that also come into a decision to invest and or like are crucial in your actual evaluation process.

Maxine Minter: And my experience is being part of angel syndicates, like you have those more unvarnished conversations with folks. Sorry, not angel syndicates, angel groups. Angel groups. Yeah.

Cheryl Mack: Yeah. Yeah. Because you can all kind of be in a room together and have those Yeah, unvarnished, I like your word there.

Maxine Minter: Yeah, like I think, like I think about some of the early calls that I had with the council and I’m pretty sure Afterworks still does this, at least they started doing this when they have their like community calls to community diligence a deal.

Maxine Minter: Yeah, they do. I sit on them every Wednesday. Yeah, I mean like it’s so valuable to have people from like different perspectives be like I’m excited about this thread for these reasons and it gets me excited to do the deal for this reason and then other people are like Well, I’m excited about this thread, a completely different part of the deal.

Maxine Minter: But

Cheryl Mack: I have concerns on this one. Yeah. And like, let’s talk about that. And like, where do we need to get pointy? Yeah, it’s those kinds of conversations that the more you get exposed to, the more you start to hone your own thinking and see where you sit on like, well, actually I’ve seen this other thing and how that comes into play.

Cheryl Mack: And then you can start to add your own to the conversation.

Maxine Minter: Yeah. One thing I’ve noticed, I never actually joined afterwards calls, but one thing I’ve noticed if I compare the calls I’ve joined in like community evaluations in Australia versus the U. S. is, I noticed a lot of people join these like angel calls and they don’t express a lot of opinions.

Maxine Minter: And so like one collective nudge I would give the Australian ecosystem is like, part of this is learning how to make decisions. It’s how to think. And so you have to do this scary thing of be like, I think this thing. about something I have very little information about. Like, help me do a better job of thinking about it, especially in those, like, early learning checks.

Maxine Minter: Like, you actually have to open up from a vulnerability perspective to say, like, I think this thing, or, like, this is what I’m, like, unsure of, or, like, I don’t understand these pieces. Because the reality, especially of, like, pre seed, seed, and, like, largely Series A businesses, is there’s an enormous amount of instinct, of intuition, that still goes into the decisions.

Maxine Minter: You know, as my coach would say, if it was possible for You’d find out on the numbers or as he calls it, like, if it was possible for the minions to like determine value here, then everyone would do it. And the minions would make the decisions, but actually there’s an enormous amount of intuition and judgment that comes into the decision.

Maxine Minter: And so thinking about like, when you’re on these calls, I think for me, it really highlighted the amount of, or the complete absence of consensus getting to excitement behind. One of these deals and conviction to one of these deals that you’re going to do it, especially at the earlier stage when there’s like very little hard data for you to

Cheryl Mack: go on.

Cheryl Mack: Yeah, it can feel so scary expressing an opinion on a call where you feel like everyone else is more experienced than you and you’re like, Hey, I don’t think it’s going to work for this reason. And the reality is that actually the, the majority of the times that I’ve expressed what I thought was probably a dumb opinion, I, I was either like, hey, I was told like, hey, actually, nobody, we didn’t think of that.

Cheryl Mack: Or somebody very kindly explained why that was a non factor and helped me understand. Like, where, where we’re at. Or, and even better, it’s agreed with, but then explained why that risk is okay. Mm. And it’s like, well, let’s identify that that is a risk, and it’s a risk we’re willing to take for this potential upside.

Cheryl Mack: And I distinctly remember the moment where I was validated in the fact that like, yes, that is a risk, and we’re gonna do this anyway. And I was like, whoa, crazy, I was right, but we’re still gonna take the risk?

Maxine Minter: I, this actually, this makes me very nostalgic, I think back to a conversation I had with one of my early mentors, a guy called Dan Friedman, who’s just amazing.

Maxine Minter: And he pointed out to me that like, there is nothing more powerful. Then being the inverted commas dumbest person in the room, right? If you just, like, give yourself permission to sound dumb, act dumb, it actually allows you to ask a lot of the obvious questions that underneath which are an enormous amount of insight and or an enormous amount of learning.

Maxine Minter: I’ve heard this in other contexts where there’s actually, like, a huge challenge for folks that get senior in their career because it starts to become harder and harder for you to be the dumb one, right? Like more and more expectation on you that you actually know the answers. You know all of the information, and like, you probably don’t.

Maxine Minter: And so, like, especially on these calls for folks that are just starting, like, relish that period of time where there is a, like, green light for you to be, you know, as, in a vertical, as dumb as you would like to ask all of the stupid questions. Like, how do you value a startup? How do you make the decision to wire?

Maxine Minter: Do you put money in a baggie? Like, you suggested, although, like, terrifying idea. But, like, also, how do you even fit money in a baggie? Anyway. By the by, I think, like, all of these dumb questions. mean? Cash? Does anybody ever have cash these days? I don’t. I genuinely haven’t carried cash for a really long period of time.

Maxine Minter: Like, maybe years? No,

Cheryl Mack: me neither. I don’t even carry a physical card anymore. Like, I went to a hotel the other day, and they were like, we need a card for the room, and I was like, you can scan my phone. And she’s like, no, I need the card. I was like, well, that’s not gonna work. I don’t have it. So what do you want

Maxine Minter: from me?

Maxine Minter: I, the US, for some reason, is really behind on fintech, like mass adoption of cutting edge fintech. It’s really bizarre. They like create the most cutting edge and then just like don’t adopt it. And so the number of times that I have been somewhere and been like, I don’t have a physical card. And they’ve, they’ve been like, well, We don’t accept any other form of payment.

Maxine Minter: Actually, even to take a further step back, the number of times I’ve been asked to pay by check. Like, when I first moved to the US, I had to pay my rent via a check, like a physical check. Like one of those paper things that comes out of a book? Yeah. Uh huh. Yeah. Weird. Not even the plastic item. Right? The, like, plastic legal tender?

Maxine Minter: Like, a paper thing that you tear from a Anyway, I could rant about this for a while. So, but my point is, is that, like Yes. Asking all of those stupid questions of like, I have used Apple Pay to pay for things for the last two years. How does one, how do I give a startup money? It’s like, it’s an open space for you to ask those questions.

Maxine Minter: Yeah. And I think the other

Cheryl Mack: one I get all the time is like, do I need a lawyer? And do I need an accountant to go over these things? And like, while I’m not going to. Give anyone advice in that sense. I can speak from experience that like when I first started No, I didn’t have an accountant or a lawyer look over anything.

Cheryl Mack: I made the decision based on the founder and Like asking friends that like hey, is this how I wire money and is this expected and they were like, yeah, that’s expected um, so yeah, i’m not gonna say yes or no on that question, but I can say that like I don’t know, did you have, no, lawyers and accountants involved in your

Maxine Minter: early stage experience?

Maxine Minter: I was lucky in that I came from a legal background, so I had just enough knowledge to be dangerous. Also, uh, you know, for a lot of these instruments that you’re investing in, they’re called safes, right? They’re just like, pieces, like, contracts. There’s, like, not, they’re a financial instrument, yes, but they’re not as robust, um, and so it was easy enough for me to kind of evaluate them.

Maxine Minter: I think it is. You know, especially if you’re writing a 2, 500 to, uh, you know, 10, 000 check, like having a lawyer review them is like untenable. Also the reality is, is for most of us that are investing a smaller amount, like there’s no negotiating leverage for you anyway. Yeah. It’s just about like you understanding the document, anchoring back on the value of learning as well.

Maxine Minter: Like, I would strongly encourage. Yeah, if

Cheryl Mack: you have a lawyer review it, then what are you learning there? If you review the document and google some of those phrases, um, like there’s some really good books actually maybe that we should mention. Um, some of the books that I read when I first started was Angel by Jason Kalkanis and Venture Deals by Brad Feldman.

Cheryl Mack: Yeah, yeah,

Maxine Minter: both really valuable. Actually, that makes me think, I mean, like the market has moved pretty significantly since they were written. Like Venture Deals was 2013. So true, actually. Angel was like 2015.

Cheryl Mack: I think they’ve done like a new edition of it. Okay. But like, would you recommend any other angel books now?

Cheryl Mack: Should we write one? Yeah.

Maxine Minter: I mean, like, let’s do it between 3 and 5am. That’s my current available slide. I’ll take it. Um, yeah, that’s interesting. I haven’t seen any of them. I know we got given venture deals by first round when they first invested in us. And I remember it was like so They gave

Cheryl Mack: you the book after they invested, right?

Cheryl Mack: So

Maxine Minter: they got the terms they wanted and then, yeah. In hindsight Smart, smart. That’s messed up, you’re right, you’re right. They also, not to, I probably shouldn’t say this on air, but they gave me a shirt that said the future is female. And it was a, like, men’s size medium. So I, like, actually Gildan size medium?

Maxine Minter: Yeah, yeah, like, actually, like, swam in the thing. So ended up just giving it to, you know, our only engineer at the time. But there was, yeah, that was a swing and a miss. That’s embarrassing. They didn’t have, like, female sizing for a shirt that said the future is female, which I was like, what? It’s

Cheryl Mack: just female?

Cheryl Mack: That’s, yeah. I actually, I get really insulted when startups give me a shirt and it’s It’s like, and it’s in a male size because in this day and age, there’s no extra cost to order different, to order women’s versus men’s in the same batch. So like, I’m like, are you serious? That just means you didn’t think about it.

Cheryl Mack: Right. Take your shirt back. In fact, I’m taking my check back. Oh wait, I already wired it.

Maxine Minter: Damn it. Yeah. Lesson. You can’t get it back once you’ve wired it. Yes. That is. It’s

Cheryl Mack: done. And not just like right away. Like. For a very long period of time so account for that being like a five to ten year horizon Oh, and the other thing that I think is really interesting dynamics is you see your losses before you see your wins Oh, so crucial.

Cheryl Mack: So like if a startup fails, they’re more likely to fail in the first like one to three years But if they’re doing really well They’re more likely to last, like, 5 to 10 years. Canva, for example, is 12 years on and still private, but, like, that’s one of the biggest success stories. So you’re gonna lose money before you see money.

Cheryl Mack: Um, in fact, my own portfolio, like, I think I’ve had 3 or 4 companies fail, and a whole bunch of companies are doing really well, but they’re doing well on paper, whereas, like, in actual profit and loss, I’ve lost money in my angel investing so far. But I’m told, and you can tell me whether this is, I don’t know if that’s accurate or not, but I’m told that I’m like on track and that like, that tracks

Maxine Minter: with what I should be seeing right about now, about four or five years in.

Maxine Minter: Right, right. I mean, the J curve, so that, that dynamic is called the J curve, named such because it is a J where the bottom of the curve sits below the zero return rate for a period of time before you come up. And I think it’s a real. Like, psychologically, it’s a real challenge for investors, because you start going backwards before you go forwards, so you start to see losses, and so you have to have the conviction of your investing to, like, really follow that through, and it’s really, it’s scary.

Maxine Minter: It’s really scary. It can be. Like, there is just a lot of investing that is scary, and I think probably why you and I love bravery in other people so much, right? Like, I know Our conversation with Elaine Stead, I just left, I already was really amazed by her and was even more amazed by her by the level of bravery that is required to kind of be an

Cheryl Mack: investor.

Cheryl Mack: Yeah, and make some of those decisions, especially when you have other people’s money, but your money as well, if you’re thinking about getting into angel investing or just early stage investing in general, like, it is a riskier asset class, you are more likely to see more losses, and you need to have the stomach for that, like, I’ve, I have, Actually, a couple of my friends, uh, have taken some of the, uh, first believers and explorers and gone to the end and said, actually, you know what?

Cheryl Mack: This isn’t for me. Hmm. Uh, and I’ve also had a couple friends who, uh, got to their first loss and said, you know what? That was actually hard psychologically and I don’t have any desire to do it again and I’m, I’m gonna stop here. And I’m like, fair enough. Like, if that’s where you sit and that’s the, like, I’m glad you explored this and Like, cool, let’s take it from here.

Cheryl Mack: Go find, you go find something that is more, more your appetite, but it is, yeah, it can be tough.

Maxine Minter: Yeah, absolutely. I actually think that there’s something to highlight here, which is that I, like, especially in today’s, well, actually not so much in today’s media cycle, right? Like a lot of the major media in Australia is pretty like off deck.

Maxine Minter: Yeah, they’re not, they’re not, uh, no, no, no, they are. They’re not as hype y on tech right now. And what is the opposite of hype? Uh, bear y?

Cheryl Mack: Yeah, they’re pretty

Maxine Minter: bear y. They’re a bit bear y? I mean, they’re definitely bear ish, but anyway. A conversation for another day. Yeah. But the, like, I think collectively the zeitgeist is like, angel investing, it’s great, everyone should do it, blah blah blah, at least in our ecosystem.

Maxine Minter: But I do think it’s like, it’s really hard to make money in this asset class. Like, rewards follow risk. You are taking a large degree of risk, and that is why the asset you know, for the top performers performs really well, but let’s be very clear, right? Like performance in angel investing and performance in funds also follows a power law curve aligned to the underlying asset.

Maxine Minter: So the top, you know, decile of funds Aware the majority of the returns are delivered. Also, with Angel investing, the top decile of Angel investors aware the majority of the returns are delivered, and then there’s kind of a long tail after that and being alive to that. For me, the way that I got comfortable with that was just my first couple of years of angel investing.

Maxine Minter: I only allocated money. I was comfortable to never see again. Yeah, because it’s also really important in the way that you make the investment decision, right? Like you seek the upside, but recognize the downside. Yeah. And being comfortable or like. at the very least engaging with, you might not get comfortable with it, but like engaging with the nature of the risk and the asset class you’re

Cheryl Mack: investing in.

Cheryl Mack: Yeah, absolutely. I think I look at it as like, well, if I end up being the worst angel investor in the world and none of my investments make money, I won’t be better off, but I, my life isn’t going to be worse. Like, I will just like stay equilibrium. Um, you know, I’m not gonna be able to buy that. 600 foot yacht that I was hoping to get or that island that, you know, I wanted to throw a big party on but I Like my life isn’t going to be worse off.

Cheryl Mack: I’m not going to be homeless I think that’s a really important piece to like recognize where you sit in terms of like your risk appetite for this asset class and What you’re willing to bet on because let’s like they’re informed Educated bets, but they’re still bets And, you know, we’re still a step above gambling at the casino, but we’re still making bets here.

Cheryl Mack: Yeah.

Maxine Minter: Yeah, absolutely. I mean, I think it’s just an important part of being a great angel investor and or, you know, largely a good investor across asset classes, right? If you are one of those people that says like, actually, I tried angel investing and either I learned about it or I actually wrote that check and that’s not for me.

Maxine Minter: And there are many other asset classes that, you know, it’s worthwhile exploring investing in, even if it is just a like, you know, listed EFT that you get minimal fees on. It makes me really sad when I meet people who just like don’t invest at all. Especially if they don’t invest from a place of like I don’t know how it works and it’s too scary

Cheryl Mack: to try.

Cheryl Mack: Yeah, that is really sad as well. I try to encourage people to see themselves as investors no matter what, especially in Australia, because we have forced super. Oh yeah, I love that perspective. So it’s like, whether you see yourself as an investor or not, you are an investor. You have savings, they are in a fund.

Cheryl Mack: That money is being invested, like you can choose to ignore that completely or you can choose to engage with that and either decide, like at the minimum you can decide where that money goes in terms of like, and even like different types of, like I know you can choose different types of funds within, like Australian Super has different ways you can, like different super funds you can put your money into.

Cheryl Mack: So like, at a very minimum, every person in Australia, he is an investor in that sense. And like once you kind of get to understand that, then you can go well, I could put more money in my super or like this next batch of savings that I’m going to make. I could allocate it to an ETF or I could put some of it towards angel investing and recognizing that like you’re kind of like super is kind of like the gateway drug here that like once you understand that you’re an investor based on super then you can start to look at other ways that you can engage.

Cheryl Mack: Like investment asset classes.

Maxine Minter: I love that thread. The, maybe even take that further is even if you, I mean, yes, if you are in Australia, you have super. And so as a result, you are investing, but also if you, for whatever reason, are not investing anywhere. You’re still making an investment decision and you’re choosing cash as your asset class.

Maxine Minter: Which, in an inflationary environment, is a loss making asset class. It’s going backwards relative to the inflationary rate. So I don’t know what inflation is in Australia at the moment. Is it like 4 or 5%? You would know better than me. I think it is four or five percent. I don’t track these things.

Cheryl Mack: I am very much optimistic, glasses overflowing optimistic, and don’t like to look at scary

Maxine Minter: numbers like inflation.

Maxine Minter: I, I mean, side note, I would strongly encourage you to look at inflationary data because it is helpful from a macro environment, but like, do you? But I, yeah, I mean, like, I think inflation at the moment is like four or five percent and If that’s true, that means your cash is losing 4 5 percent of its value every single year.

Maxine Minter: So you are making the choice just to invest in cash that is going backwards. That’s your cash rate.

Cheryl Mack: I’m on the RBA’s website, and it says It says that they aim to keep it between 2 3 percent on average over time. That doesn’t tell me what it actually is. Uh, inflation rate eases to 4. 9 percent in October.

Cheryl Mack: That was, uh, yeah, so we’re, we’re

Maxine Minter: at 5 percent right now. So your cash is going backwards in value at 5 percent a year. Yeah,

Cheryl Mack: that’s not great. So cash is just It’s like, not a great investment

Maxine Minter: considering. No, it’s, it’s actually like a really bad investment if you’re just holding cash.

Cheryl Mack: I guess as we kind of come to the end of this, like, what is one thing that you would like to tell new investors who are thinking about getting into this space?

Maxine Minter: Oh, one thing. I just get one bullet. I think my one bullet would be for people who are Like tech curious and or investing curious generally, I think investing via syndicates and or for, especially for folks in tech that feel like they understand the businesses to a greater degree or want to understand the businesses investing in small companies is a really wonderful way.

Maxine Minter: an educational way to learn about businesses generally. I think the comp that I think of here is like when you learn to sail, you learn to sail on a really small, simple sailboat, trying to remember the name of them, a laser, which is just like a hull and a mast and a sail and like some very basic rigging.

Maxine Minter: And you learn to sail there. before you, you know, go and sail these like big super yachts, if you ever kind of get to that stage, which is like very complex, lots of machinery moving around, et cetera. Understanding business isn’t their most fundamental. At the very earliest stages is so valuable no matter what investing you want to do if you’re investing in companies.

Maxine Minter: And so I think it’s a really educational place to spend time even if you’re only investing 10, 000 over five years via a syndicate platform writing a couple of checks a year. I think it can be really informative. And so taking that lens no matter what happens to the money at the very least you’ve learned

Cheryl Mack: loads.

Cheryl Mack: Yeah, I think I can’t remember who it was but somebody said like you could put 50k towards an MBA or you could put 50k towards five startups over the course of two years and probably still learn the same amount if not more. Right. I think I read that on Twitter one time and I really liked it. I’ve quoted it like six times.

Cheryl Mack: Um, on my side, I think my like one piece of guidance is if you’re looking to get started reach out to somebody. That you know who is angel investing and, and or investing in this asset class and if you don’t know somebody then ask somebody to introduce you to somebody, but I think that first step of talking to somebody else about their experience, about how they’re doing it for me was the catalyst and I just learned so much from reaching out to other people and asking them questions.

Cheryl Mack: And getting a sense of what they were doing. And most people are happy to, like, share and bring you in on what they’re doing. Myself included. Like, my, my calendar is open for angels who want to learn. And I’m happy to be that first person for you if you don’t know others in, in your own ecosystem. But that would be my first step.

Cheryl Mack: Reach out to somebody who is doing this and ask them

Maxine Minter: about it. Yeah, I love that. I mean, I think just to like underline that everyone who’s listening to this knows at least two people who are angel investors, right. But because they know us, so reach out to us. Yeah. If you don’t, hello, I’m Cheryl. I’m Maxine.

Maxine Minter: Now we know each other. Excellent. Thank you so much. Great chat as always Maxine. See you next time.


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