Your Warm Intro to First Cheque with Cheryl Mack & Maxine Minter

First Cheque

Cheryl and Maxine give your a warm intro to the First Cheque_First Cheque_01

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Maxine and Cheryl kick off the First Cheque podcast, a show dedicated to helping early-stage investors become better at their craft. They aim to open source conversations and insights from experienced investors to provide valuable information and education for emerging investors. The podcast focuses on the Australian ecosystem but also explores international perspectives on investing. They discuss the importance of understanding risk, the distinction between betting and investing, and the need for better decision-making processes. They also touch on the current state of the market, noting some green shoots and increased deal flow, but also expressing concerns about the sluggishness in the series C to E stages.

Key Takeaways

  • Open-sourcing conversations and insights from experienced investors can help emerging investors become better at their craft.
  • Understanding risk and making intelligent risk-taking decisions is crucial for successful investing.
  • The distinction between betting and investing lies in the ability to control risk factors and make informed decisions.
  • The current market shows some green shoots and increased deal flow, but there are concerns about sluggishness in the series C to E stages.
  • This is a great time to be investing, especially in early-stage companies that demonstrate resilience and have the potential to thrive in the future.


  • “If you want to be a better early-stage investor, this is the show for you.” – Maxine Minter
  • “Being compensated for risk is the variable of return profiles in different asset classes.” – Maxine Minter
  • “Investing in startups is risky, but there are factors you can control and levers you can pull.” – Cheryl Mack
  • “Great investing is good decision process plus great information.” – Maxine Minter
  • “This is a great time to be greedy and invest in early-stage companies.” – Maxine Minter


This transcript has been A.I. generated.

0:00:00 – (Maxine Minter): So I think just working out and open sourcing a lot of those conversations that are happening in Silos or behind closed doors or over coffee or over dinner, that we get to be part of sitting around that table. But we want that stuff to be open sourced. About what? Have the best investors here in Australia and internationally worked out about being great investors?

0:00:19 – (Cheryl Mack): Okay.

0:00:20 – (Maxine Minter): Three, two, one.

0:00:23 – (Cheryl Mack): Hey, I’m Cheryl.


0:00:24 – (Maxine Minter): I’m Maxine.

0:00:25 – (Cheryl Mack): This is First Check part of Day One, the network dedicated to founders, operators and investors.

0:00:29 – (Maxine Minter): If you want to be a better early stage investor, this is the show for you.

0:00:32 – (Cheryl Mack): So TLDR, if you don’t want to suck at investing, listen up.

0:00:39 – (Maxine Minter): Hello. How you doing?

0:00:42 – (Cheryl Mack): I’m good.

0:00:44 – (Maxine Minter): I’m excited to start recording this. Obviously we have talked about this for a while and excited to kick off the First Check podcast, episode zero.

0:00:53 – (Cheryl Mack): The first check podcast.

0:00:55 – (Maxine Minter): The first one. First ever.

0:00:58 – (Cheryl Mack): First ever.

0:00:58 – (Maxine Minter): We’re recording this. Yeah. From our lounge rooms when we have our best chats. Really just to kick off. I think what I’m hoping will be a fun journey together, exploring and cross training across various investment styles to become better investors.

0:01:15 – (Cheryl Mack): Anytime I get to talk to you about investing is a good time. I get to learn a lot and really fun topics come up.

0:01:22 – (Maxine Minter): So, yeah, we are kicking off the podcast to really talk about investing, especially for first checks because we wanted the right we do and place that we come together and just open source some of those conversations that we were getting access to and those conversations that we get to be part of on a day to day basis, especially in the Australian ecosystem, but all over the world.

0:01:48 – (Cheryl Mack): 100%. I feel so lucky sometimes when I’m sitting at the table with Rick Baker and Craig Blair and Raynong and Matt Brown and you and Izzy, and I’m just like, these people have so much to share and I get to sit here and listen to it and just soak it all in. So we’re going to bring that to you, all of you viewers who are out there. Viewers.

0:02:08 – (Maxine Minter): Listeners.

0:02:09 – (Cheryl Mack): I think it’s listeners on podcasts. Are you guys live? Is anyone there?

0:02:12 – (Maxine Minter): Right. Yeah, I think that’s true. Just hang on. Actually, at the moment and I shit talking in our lounge rooms, literally no one is listening.

0:02:19 – (Cheryl Mack): But hopefully, hopefully watch, no one shows up to the first one. I promise we’ll make it good, guys.

0:02:26 – (Maxine Minter): Yeah, I mean, the goal is really open source some of those conversations that we’re getting to be a fly on the wall for. So, as you said, it’s such a privilege to be around the table for some of these conversations. More people could be for know. The goal being that we have conversations with some of those investors that vested across stage, even in different asset classes. I actually think that this is something that to be a great investor anywhere in the world, but especially in Australia and the broader capital ecosystem that you’re part of, to understand the kind of broader business ecosystem that you’re part of. And I don’t just mean the one that stops at Australia’s national borders, right? Like, capital flows internationally, ideas flow internationally, entrepreneurs move internationally. And so being a great investor, which is what we aimed be, to really understand who internationally has worked this stuff out, who nationally has worked this stuff out, who locally has this stuff out, and to have those conversations.

0:03:21 – (Cheryl Mack): Absolutely. I remember you mentioned something about how I was really concerned about the rental market in New York City and actually I told you that the rental market in New York City for office space had completely collapsed. And you’re like, that’s really concerning for us. And I was like, what do you mean? No, it’s not, that has nothing to do with us. And there was this tangent of these good things could happen. And so I think as investors, it actually is important to keep track of some of those extra things that are happening outside of our little sphere. And bringing some of those conversation into what we’re talking about, I think is going to be one of the more interesting things that we’ll touch on during this podcast, hopefully.

0:03:58 – (Maxine Minter): Yeah, I can’t wait. And we have some amazing guests lined up as well. One thing I do want to align on and maybe chat about first is how you even got into this. I know we’ve had lots of chats about those first checks that we wrote, why we started angel investing in particular, because obviously both of us do early, early stage stuff like precede. I just do precede at coventures and you do precede through to Series A, I think is the latest deal I’ve seen you do. But how did you kick it off? How did you get the cajones to write those first dollars?

0:04:27 – (Cheryl Mack): Cajones. I like that not because I feel like I have cajones, but because it reminds me that this is something that you do have to be a bit brave on, which hopefully we’ll touch on with our next topic. But yeah, I fell into angel investing completely by accident. I started a company called Sarkon a little while ago and I was just really close to a lot of founders during that time. And we brought investors and founders together, one of the largest startup events in Australia’s history.

0:04:54 – (Cheryl Mack): And it turns out that you can’t just throw a thousand people in a room together and hope that the investors and founders will find each other. So we actually got really interested in.

0:05:01 – (Maxine Minter): How do I help?

0:05:02 – (Cheryl Mack): I know, right? Like, put them in a room. Fine. I really got really interested in how do founders find capital and how do investors find the founders that they want to invest in. And then because I was just really involved in that space I was working with a couple of startups, one of the founders who said, hey, we’d love to have you come work for us, do a bit of marketing. We can’t pay you in cash, but we can pay you in equity. How does that sound? I was like, all right, cool.

0:05:26 – (Cheryl Mack): Yeah, that’s not like deploying checks. That’s not investing. It’s just investing my time. I’ve got plenty of that. That’s not super valuable or anything. And so I was working for a couple of founders, just doing stuff like that. And then I was up having drinks one day and one of them were like, oh, we’re just trying to close our round. And I was like, oh, cool. How much do you have left? He’s like, 20 grand. Oh, really?

0:05:48 – (Cheryl Mack): I thought in order to be angel investor, you had to invest like hundreds of thousands of dollars, like 20 grand. And I could invest. I could do that. He was like, all right, sweet. Helps you get back to running the company. Awesome. And then that happened again and two checks in, I was, I wonder if maybe this is what angel investing is. Maybe I should find out what I’m doing. And so I called up some of the investors that I knew in my life and funny enough, I didn’t know very many angels. I mostly knew in VC investors. So I called up John Henderson and Kylie Fraser, who was she was running angel syndicate at the time, but I was like, hey, I think I might have started angel investing.

0:06:24 – (Cheryl Mack): Not sure. Tell me what I need to know. Go. And the best part of what they said was that they were like, you’ve only written two checks, you’re probably going to lose that money. And I was like, oh, is there an option B? And they’re like, yeah, if you keep investing, you’re probably still going to lose that money, but you might have a chance of making it all back on the next sum. And I was like, I choose that.

0:06:44 – (Cheryl Mack): So here I am, 26 checks later.

0:06:46 – (Maxine Minter): My first learning check, writing those dollars. I get this question all the time from folks about the distinction between betting and investing, like early stage investing. And the reason I say that is that, oh, if you just keep betting, you’ll win back your losses. Has a similarity to betting, but I don’t think they have to the casino, it is a phrase that you hear a lot with problem gamblers and I just kick it out.

0:07:17 – (Maxine Minter): I actually have spent a lot of time thinking about this when I first started investing. Are there controllable risks here or are you just like playing with luck? I think that’s the distinction, right? The difference between really high quality investing at a very early stage when there’s a high level of risk is are there risk factors that you can control versus not betting you can’t control any of them and you are just playing with Lady Luck every time.

0:07:40 – (Maxine Minter): Investing with a high risk profile I think is where you can control some of those factors. And actually the topic that I’m super excited to chat to all of the amazing guests we have coming on is about how they think about risk, how they think about intelligent risk taking in their asset classes and at those stages. Because being compensated for risk is in theory the variable of the return profiles you see, say between precede and series C or between options investing and value investing for large Fortune 500 companies.

0:08:23 – (Maxine Minter): The way that those investors think about risk I think can be really informative for us at the earlier stages to get more sophisticated in the way that we think about risk.

0:08:31 – (Cheryl Mack): Absolutely. I actually think that the betting analogy is a really poor one. I often hear that argument of why people can’t get involved in early stage investing because they’re not sophisticated investors and they’re like, yeah but I can go down to the casino and blow 50 grand. I’m like that’s really not a great analogy. Investing in startups, yes, is risky, but there are a lot of factors that come into play that you can pull threads on and pull levers with. It’s not the same as the casino machine pokey lever that you just pull over and over again.

0:09:01 – (Maxine Minter): These levers are the best analogy.

0:09:03 – (Cheryl Mack): It really is not actually in a pokey machine.

0:09:06 – (Maxine Minter): Don’t use that analogy.

0:09:11 – (Cheryl Mack): It is actually a very different activity than just walking down to the casino and putting your money in and pulling that lever over and over again hoping that there will be a different outcome. So we need to move away from that analogy, right?

0:09:24 – (Maxine Minter): For sure. But I do think that a conversation I hear a lot of is like how VCs talk about risk and are open about the nature of the risks that they are taking. I think there is a lot of attempts and I know I’ve seen it in my own decision making behavior and attempts like false accuracy or false certainty to construct certainty around decision making that doesn’t exist. Just like being aware of and comfortable with the nature of the risk that you’re taking and trying to get more and more sophisticated in terms of understanding that risk. That’s actually one of the things that I’m really excited to profile here in this podcast, which is just that in theory, better information leads to better decision making and the goal here is to open source. In theory.

0:10:08 – (Maxine Minter): And the goal here is to open source why all of those additional information feeds that hopefully will help folks become better investors and be more thoughtful about the way that they’re investing. Learning more about liquidity, learning more about how it moves through different markets, why that matters at early stage, why that might matter for the exit profile of the businesses that you’re investing in.

0:10:30 – (Maxine Minter): There’s so many bits I’m so excited to dive into. I wish I could just sit here for the next four months and just have conversations with people, but unfortunately we have full time jobs.

0:10:38 – (Cheryl Mack): Wait, but that is what we’re doing. We will be having those conversations for the next however many months with whoever we want, hopefully with people who are come and chat with us about early stage investing. I think the key here is we’re targeting this not at founders, because I think there’s a lot of content out there for founders who want to learn about how VCs and investors think in general. And I’m sure you have as well. But I’ve done so many podcasts where the audience is founders and I’m talking about why I invest in what I invest, what I look for, the type of founders I’m profiling, the DD that I go through, like all of those things. And that’s super helpful for founders. But our goal here, I think there’s not a ton of content out there actually I can’t really think of much, particularly that’s focused in the Australian landscape. But our goal here is really to talk to those emerging investors, both emerging fund managers and early state angels and new angels who are thinking about investing.

0:11:30 – (Cheryl Mack): Because when I started there was a couple of people I could go talk to, but there weren’t programs out there. And there are some amazing programs out there now, particularly for Australian investors, but overseas as well, there’s lots of education, but there isn’t really an Australian focused voice around providing content for those emerging investors. And I think that’s who we want to talk to and open it up. So I think we want to be super clear about that, that this isn’t necessarily for founders this time around. This is for people who want to learn and become angel investors or write their first checks or become fund managers.

0:12:02 – (Maxine Minter): Yeah, 100%. I will also say that this content is valuable as a founder. Right. I think what we’re talking about as investors and what you need to be excellent at as a founder is allocating capital, be they dollars or your hours or the other resources in your organization. We are talking about and exploring with different folks how best to make those decisions and how best to make those allocations so true. It’s not going to be like how to think about an effective go to market motion or how to work out what color the button should be.

0:12:38 – (Cheryl Mack): But I do how to get investor attention.

0:12:41 – (Maxine Minter): Yeah, exactly. I guess indirectly understanding your market is super important to be able to talk to investors I do think that they’re like. So I wouldn’t say that it’s not relevant for founders and also not relevant for more seasoned investors. Like, my goal is that we have conversations that are interesting across the board. But you’re right, I think we want to open source the conversation mostly for those folks that are, let’s say, the first five years of their investing journey in early stage. Because I think that as you said, there’s not a lot of folks having the public discussions about how to be excellent with the dynamics in the Australian market. Like, there’s so much content about strategies that are really effective and principles and heuristics that are really valuable in the US market. But there’s so many elements of the US macro market that don’t map to Australia, right? Like size of market, liquidity of market, where the pools of capital come from, the decision makers that control like, even just the realities of supply chain logistics to Australia. Right? Like the profile of an investment in ecom in Australia is so different than the profile of an investment in ecom in, say, Europe or in US.

0:13:53 – (Maxine Minter): I think being thoughtful about the distinctions and you’re right, there’s not those places in the Australian ecosystem that I’ve found where people are having these conversations in public, so excited to open source them. So the last point I made was just that I’m excited to open source those conversations. So I might start here with another question. So as we think about open sourcing these conversations and looking at the landscape as it is today, we’re recording this on the 5 August in 2023.

0:14:23 – (Maxine Minter): I feel like I’m starting to see some super exciting green shoots in the market, both in the US. So for context, I invest across the US and Australia, actually globally, but heavily focused in the US and Australia just at Precede. And I think that I’m seeing some really exciting green shoots in the US. And I am hopeful we’ll start to see them in the Australian market. But does that start to feel like things are picking back up again?

0:14:46 – (Maxine Minter): Would love to hear what are you seeing out there? What does the market look like?

0:14:49 – (Cheryl Mack): Yeah, that’s interesting. I’d say every time. So over probably the last one. Yeah, probably one year I’ve routinely asked the question hey, what’s your quantity of deal flow? Like, what’s it look like? How quickly are you deploying? And last night so I run an event called Three Six One Angel Club and we just bring together founders and angels once a quarter in City and Melbourne. Last night I asked the question to a number of investors and for the first time in probably a year, three of the ones that I asked said something along the lines of our deal places picked up. We’ve done more this quarter than we’ve done in the last twelve months.

0:15:24 – (Maxine Minter): Hey.

0:15:24 – (Cheryl Mack): And we’re seeing we’ve deployed a lot of capital and we’ve done a lot of deals in the last couple of months. I’m like awesome. I wasn’t expecting that because over the last twelve months I’ve consistently gotten the answer of it’s slow. We’re not seeing a lot, we haven’t deployed a ton. And that also factored in the so I’m an LP in a number of funds. And I’d say over the last maybe, I don’t know, 18 months, like 15% of the capital that I’d committed has been called.

0:15:50 – (Cheryl Mack): In the last probably month, I’ve had capital calls from nearly all of the funds. So to me that tells me that there is green shoots, as you call them, that are starting to crop up and pace is increasing. I guess my question is, does that mean that we are on the up? Are we in recovery mode? Are we heading up? Obviously it’s going to take longer even if we are, but thoughts?

0:16:12 – (Maxine Minter): Yeah, I think I hope it is. I am an eternal optimist and I have learned via my decision diaries that I can get see positive data and extrapolate positive trend where they are just aberrations. So I hope that’s what that is exciting data that is suggesting at least a kind of bottoming out as opposed to we’re kind of falling and then we’re going to see an uptick. But it’s so hard to know. A lot of the data I get to see is retrospective. So it looks back on like previous quarter or previous half.

0:16:45 – (Maxine Minter): But I do I will say anecdotally I’m feeling it. We’ve done nine investments in we’ve done six investments in six months. And we did three investments we warehouse three investments in. So we’ve done nine in like we’ve got a portfolio of nine companies and there’s probably three I’m looking at this week that I’m excited about investing in and that’s no. Okay.

0:17:08 – (Cheryl Mack): So we’re open definitely not for deal flow.

0:17:11 – (Maxine Minter): Got it. Absolutely.

0:17:14 – (Cheryl Mack): Portfolio companies last night, go Tradie.

0:17:17 – (Maxine Minter): Yeah, they’re amazing. I actually think you met two of them last night.

0:17:22 – (Cheryl Mack): Who’s the other one?

0:17:23 – (Maxine Minter): Tapestry. Chris from tapestry.

0:17:25 – (Cheryl Mack): Yes, I did meet Chris from Tapestry as well. Yeah.

0:17:29 – (Maxine Minter): Both amazing. That’s excellent.

0:17:30 – (Cheryl Mack): Me and Go Tradie basically just went off on a rant about how amazing you are and I was like, she’s not even here. We should have her here for this.

0:17:39 – (Maxine Minter): That’s so kind. I will actually say in the last 48 hours since that event, I have bumped into or chatted to eight people who were at that event. Like, that event sounds like an incredible I’m so sad that I missed it. It was just consistently bring the best people in the ecosystem together. But I do think that they are green shoots that are exciting to see, especially at this early stage. Now on the counter to that, I had a conversation with some folks in the US. This morning and series C to E still sounds like a graveyard.

0:18:10 – (Maxine Minter): The feedback I’m continuing to hear is that that is a really tough stage. Still slower deployment, price depression, all of the things that we don’t want to hear and which you need to see a thriving progression from stage to stage for each of the stages to continue thriving. Right. If series C to E or C to through to IPO continues to be sluggish. It’s not going to be great for the early stage for us, because precede, in a year and a half, they become if they do well, they become A, and then a year and a half after that, they become B and et cetera. So I’m still a little bit concerned that we’re seeing the sluggishness there. We’re not seeing the activity at IPO. We need to see for the kind of pipes to clear out.

0:18:52 – (Maxine Minter): But I’m, as I said, eternal optimist excited about some of those green shoots. And I do think that this vintage of companies are going to be incredible because I think that this vintage of companies, if they succeed and they survive through this stage, then they will get to the growth stage and be in a much better place. Yeah, exactly. Highly resilient. I think they get through to that growth stage, and there will be very few competitive companies at that stage because most of them won’t survive at this stage. So I think from an investing perspective, I am extremely bullish that now is a great time to be greedy. They do say when the markets are down, be greedy. I think now is a great time to be greedy because I think that the ecosystem that these companies like Early Stage, Precede and Seed will be growing into and selling into is going to be back in the middle of the cycle.

0:19:46 – (Cheryl Mack): Yeah. Oh, it’s a great time to be investing. I think most investors are on our side with that. It’s probably a little dangerous to have two eternal optimists running a podcast together, but we’ll temper that with some pessimistic guests along the way. One of the things you mentioned actually a little bit earlier is you said this word decision diary, and I actually think you’re one of the most unique investors that I get to talk to on a regular basis.

0:20:09 – (Cheryl Mack): And I would love to jump into a bit more maybe on another episode. Like, what is your decision diary and how does it work and how do you have the mental effort and diligence to do that? But I’m assuming you didn’t do that right from the beginning. So one of the things we didn’t touch on, I’d love to understand. How did you start angel investing and what did your first couple of learning checks look like?

0:20:28 – (Maxine Minter): Yeah, my first learning check was $2,500 backing a DT at Zeta. And I’m not going to pretend I knew what I’m doing, I was doing at the time. Like, I got lucky. She is just building an amazing company and she’s an amazing founder. But I wouldn’t say that was insight. Right. That was pure luck. Just right place, right time, being wowed by a founder. And I think that I really like this term of learning check. I think it’s really important to recognize that as you are learning to invest, a lot of it is instinct, and you need to earn the right to have that instinct by doing quite a few reps.

0:21:02 – (Maxine Minter): I do think what’s really exciting, though, is that there are now platforms like Aussie Angels that allow you to do those learning checks at a much smaller clip than you might have had to in 2012 or whatever.

0:21:12 – (Cheryl Mack): My first one a lot smaller than mine.

0:21:15 – (Maxine Minter): Yeah, kudos to you. You’re writing 20K learning checks. That was like literally half my take home salary at the time.

0:21:23 – (Cheryl Mack): If I could have written smaller learning checks, I would have.

0:21:26 – (Maxine Minter): Yeah. So that was the first check I wrote. And what I learned from that is I had no idea to make that decision. I just was like pure instinct. Adidi and the team are incredible. Really interesting space, really impressed with execution pace. I will invest and invested through a syndicate over time. I can’t remember who taught me about Decision Diaries. It’s definitely received wisdom. I didn’t divine my way there from first principles, but I can’t remember who did that. So whoever did that, thank you so much. You changed my life.

0:21:59 – (Maxine Minter): But so a decision diary just on like, how your decision diary on Decision Diaries in case someone else wants to.

0:22:05 – (Cheryl Mack): Copy you and divine that from you, right?

0:22:08 – (Maxine Minter): Yeah. Happy to share. I am the biggest advocate for Decision Diaries. I think that exists. But essentially a decision diary is where you record how you made a decision, what information you relied on when you made that decision and what your decision was so that you can review it at some kind of hindsight, set off and have quality information to make that assessment. And the reason you do that is because it’s actually really hard.

0:22:31 – (Maxine Minter): Without some record of what the decision is that you made and how you made it and the facts that you had at the time, it’s really hard to assess the quality of your decision making over time. And I am all bought in on the school of thought that great investing is good decision process plus great information. So have been poning my decision making process ever since.

0:22:52 – (Cheryl Mack): I think it pulls a really interesting thread that investing is a very brutal feedback cycle. You’re looking at five to ten years on getting any feedback as to whether your investment decision was a good one or not. And so anything that you can do in the shorter term to try to either shorten that feedback cycle or get better confidence that you’re utilizing the best information possible to make those decisions so that you’re not just waiting five to ten years to get that information back, I think is super key.

0:23:25 – (Cheryl Mack): So hopefully we’ll be able to surface some of that for everyone listening as well.

0:23:29 – (Maxine Minter): Absolutely. With that, I am so jazzed to be on this journey with you and can’t wait to shit talk for half an hour to 45 minutes at a time over the next many years of podcasting together and excited to be on the journey with all of you listening as well. I hope you enjoy the journey and we hope this is a conversation with you. So reach out, tell us what you think. What do you want to learn about? What information?

0:23:54 – (Maxine Minter): Do you want to know? What stupid acronyms are people using that you don’t understand that we can demystify? Yeah. So excited to be on the journey with you. And great to catch up.

0:24:06 – (Cheryl Mack): Absolutely.

0:24:07 – (Maxine Minter): I cannot wait.

0:24:07 – (Cheryl Mack): Maxine, it’s going to be great.

0:24:09 – (Maxine Minter): Thanks, everyone.


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