Navigating Early-Stage Investing and Scaling with Tim from Turo

0:02 Cheryl Mack: Founders scale faster on Deel. Set up payroll for any country in minutes. Hire anyone anywhere. Get visas handled fast and get back to building. Visit deel.com/dayone. That's d-e-e-l.com/dayone. Okay, 3, 2, 1.

0:26 Maxine Minter: Hey, I'm Cheryl.

0:27 Cheryl Mack: I'm Maxine.

0:28 Maxine Minter: This is First Check, part of Day One, the network dedicated to founders, operators, and investors.

0:32 Cheryl Mack: Investors. If you want to be a better early-stage investor, this is the show for you.

0:35 Maxine Minter: So TL;DR, if you don't want to suck at investing, listen up. All right, so we have a fun guest coming up. I am so excited about this guest because they have a wealth of experience. They're one of my first investors and, uh, and backers, and they've done some really fun stuff. Maxine, what do you love about Tim?

1:00 Cheryl Mack: Ah, I'm so excited to chat to Tim. You actually were the intro between the two of us. You invited us both to an event with UNSW, so we were on a panel together, and that was my first intro to him. And he was actually one of the first operator angels in the Australian ecosystem that I met. And as far as I can tell, you know, pretty early to that scene in the Australian ecosystem. So I'm just so excited to chat to him, all things like mobility, how do you think about being an operator angel, Is there a kind of bleed between one to the other? Do you bring the insights you learn from operating into investing and vice versa, or are they completely different activities, kind of side hustles?

1:38 Maxine Minter: I'm gonna go yes, he definitely brings them between, mostly 'cause I've seen him do it. So, I mean, he was at Uber, now he's at Turo, and absolutely love Turo, by the way. If anyone has any car needs, please check them out. Such a fan. And now he runs this like micro fund, which I know they've gone into a few funds as well. So it's almost like a micro fund of funds model, which I think is also becoming more popular in Australia.

2:02 Cheryl Mack: Right, absolutely. This like blended model I think is super interesting, the one that they've been running. So, so excited to dive in. Can't wait to chat to him.

2:09 Maxine Minter: Let's get into it. Okay, we've got Tim. Tim, welcome to the podcast.

2:18 Tim Rossanis: Hey, great to be here. Thanks, guys.

2:20 Cheryl Mack: Thank you so much for coming on.

2:22 Maxine Minter: Yes. One of the first questions that we love to ask our guests, and we have had some very interesting answers so far, so curious to hear what yours is, but we love to ask, what is the very first thing you ever invested in?

2:35 Tim Rossanis: Wow. Okay. It's a tricky question. And it's not literally invested in, it could be like a thing rather than an asset, right?

2:44 Maxine Minter: A thing in your education? I think we heard somebody invest in like a toaster. Yeah, whatever.

2:53 Tim Rossanis: A toaster, okay. Yeah, I was thinking a little bit the other day about like my high school to university experience. And I really wasn't super motivated in high school. Like I just didn't care much. I tried a little bit, but I didn't try super hard. I ended up starting my first year of uni in like pre-med. Thinking that I would go into medicine. And after about a year, I realized I don't want to be studying science for the next decade and a half. And I made the transition to, you know, business, economics, and international relations. And I think, I think that change, like investing in myself and my interests— I wasn't genuinely interested in medicine. I just think that there was, there's so much, you know, positive association with it. It was almost like a status thing. And I realized that that's just not really that important. You know, what's much more important is pursuing your interest areas and your passions. And so, I made the change after a year of uni to study something that I thought was actually aligned with what I wanted to do with my life. I think that investment gave me a lot more confidence. And I've also always been a really, I guess, you know, driven person outside of education, like driven to be successful. And so, Transitioning into something that really was genuine and interesting to me allowed me to develop my own confidence and back myself to take risks, which I've done over and over again in my career. And, you know, I wouldn't be where I am today if I wasn't willing to take those big risks. So I think, I think it's that, you know, like investing in making a difficult change. You invest a year of your life at 18 in a course and, you know, you have to change direction altogether. It wasn't an easy thing to do, but I'm really glad that I did it.

4:38 Cheryl Mack: It's amazing how big of a change it feels when you're 18, right? Like, I feel like at this point—

4:44 Maxine Minter: But looking back—

4:46 Cheryl Mack: Yeah, but like, talk to a lot of folks who are early in their career, like in university, and the prospect of like wasting a year— like, they're in such a rush. And maybe this just makes me feel really old just talking about this, but like, people being like, oh, but what if I've wasted a whole year doing a year of a course and now I'm gonna have to like redo it all again? I'm like, my friend, you are going to be like— life long, you have got lots ahead of you. Like, I think it's a great investment for you to make, but it's material, right? Like, at that— in that moment, deciding to be like, I'm going to make a major shift, especially away from something like medicine.

5:19 Tim Rossanis: Yeah, I mean, at the time, a year of your life at 18 is like, you know—

5:23 Maxine Minter: One-eighteen.

5:24 Cheryl Mack: Yeah, exactly.

5:25 Tim Rossanis: It's like 5% of your life or whatever, and, and that, and that feels really significant. I think that, that, you know, as you go on though, that, that that insight still applies. Like, even in your— like, I'm in my mid-30s now. Taking a year or two to work out, like, what should be next and how to get the best outcome, you know, moving slowly—

5:45 Maxine Minter: Never a waste.

5:46 Tim Rossanis: It's never a waste. And moving slowly towards the things that you're really passionate about, I think, is always worth it at any stage.

5:53 Cheryl Mack: 100%, hard agree. Someone said to me recently, the combination of being smart or intelligent, hardworking and patient is so rare. And the patient piece there is the big unlock, right? If you can truly be patient and like truly predict where the market is gonna be going or where career trajectories are gonna be going or what you might want in 10 years' time and then like build your way into it, it fundamentally changes the opportunity that you have as opposed to constantly. needing like short-term validation or short-term returns on the investment of that. And I think what I'm, something I'm really excited to dive in with you today here is I think you saw line of sight to operator angels in the Australian ecosystem way before most folks in the Australian ecosystem got to see that. I mean, you are, you've been investing in the Australian ecosystem for a really long time. And so that kind of operator angel angle, I'm super interested to dive in with you here today. But maybe to kind of start off with, can you talk to us about your journey into angel investing? Like what got you off the bench?

7:00 Tim Rossanis: Yeah, it's a, I don't know, like a somewhat convoluted story. I started angel investing with two of my best mates, Ariel and Mike, and we'd been friends for a long time, like me and Michael since we were kids. And, you know, Ariel, Michael and I went away after school together for a gap year. We just like were part of the same group of friends for a long time and talked about tech all the time. But we all lived in different cities and in 2020, we decided that we wanted to make some angel investments. And so we formed a structure called Nullarbor Ventures as a kind of nod to the fact that I'm in Sydney, Ariel's in Melbourne, and Mike is in Perth. And we just, we have got really complementary but fairly different backgrounds. You know, Ariel's from management consulting and then has been in strategy at Seek. Mike is a Big Four kind of accounting background by trade and then has a lot of experience in logistically complicated businesses. And I spent quite a while in the travel sector, uh, and then a bit of time in supply chain and procurement when I worked for American Express. And then I did my MBA in New York, and that was kind of the, the moment where I got really inspired that I wanted to work in technology. When I was doing my MBA, uh, we had this guest speaker from First Round Capital, which was, I think, now one of the most famous, you know, venture firms of all time.

8:23 Cheryl Mack: Yeah, cool.

8:23 Tim Rossanis: Who did you have? Howard Morgan.

8:26 Maxine Minter: You didn't know that at the time. You were like, who is this guy?

8:29 Tim Rossanis: No idea. Yeah. I'm like, who's this random old bloke? And he told us the story. This is 2016 or '17. And he told us the story of how he invested in Uber. He was actually the first institutional investor in Uber, I assume, like after J. Cal and that round of angels. And it just like, and even talking about it now, like it makes me feel, I don't know, I've got like goosebumps thinking about it. And at the time it had this really distinct impact on me because he was talking about how quickly they moved. And I was living in New York at the time and using Uber all the time. And so, I could see the real-world effect of this incredibly innovative business that I thought was changing the world and had changed the way that I traveled in cities. And then he was telling us all the stories about, you know, TK and the negotiation with municipalities and not being regulated and how quick they expanded and the like operator model that they implemented to expand really like their playbook really quickly. And something just like this, this switch flipped. And I realized like, I have to work in technology, even though I'd spent the better part of a decade at that point working in primarily in travel. And so from there, like if I fast forward 3 or 4 years, I was working at Uber in Australia and had, you know, made a bit of money, sold our apartment when we lived in New York, and had like equity in Uber that I'd accumulated over time and had this opportunity to invest in Superhero. Before I started at Uber, I helped John a very little bit in the kind of very early days of Superhero before they even launched. And so when he was raising some funding, he came to me and said like, do you want to write a check? And I told Michael and Ariel, and we decided that we'd write a check together. We raised some money from family and friends and created Nullarbor. And then, you know, along the way we've made a bunch of really cool angel investments into companies directly. We've also made quite a few investments into funds. I don't know if this is true, but I don't know of any other funder funds like us that has invested in Airtree, Blackbird, and Square Peg. And then, you know, some of our direct deals, we obviously invested in Aussie Angels, Cheryl, which we are thrilled about because, you know, angel The angel syndicates in Australia are coming a long way. And then we invest in other funds like EVP and Afterwork, and of course now co-ventures as well, Maxine. So very thrilled to be an investor for both of you and what you're doing.

10:57 Maxine Minter: Yeah, we just set this all up.

10:59 Cheryl Mack: Right, right. Yeah. We keep it in the family. Why not?

11:03 Maxine Minter: We really do.

11:04 Cheryl Mack: Why not? I'd love to double-click actually on, you know, that journey, especially as you started to, especially the directs, obviously the fund investments. I think that's super interesting that you guys are the only founder funds that have got positions in all three that isn't like a large institutional. But on the direct investments, you know, especially given that you three are from such different contexts and you have a lot of experience in travel and a lot of experience now in, you know, mobility or, and cars, does it factor into the way that you make decisions? Like how does your operator hat influence your investor hat and vice versa?

11:44 Tim Rossanis: Yeah, it's a great question. I think it does have an impact. You know, in some ways it has an impact because some of our LPs in our little angel fund are people that we've interacted with in our operator roles. And so they've written checks and they wanted to get exposure into, you know, venture-style investing and they trusted us to do that on their behalf. So to a degree, I think that's a bit of an impact. I also think that, you know, the nature of the work that we've done means that we had enough credibility to get meetings with founders doing interesting things. We didn't always have enough credibility to successfully write a check that they accepted. We had a couple of rejections in the early days, especially some of which I'm actually now kind of happy about, to be honest. And it definitely didn't mean that we only made good investment decisions.

12:30 Maxine Minter: I was going to say, any that you're not happy about?

12:32 Tim Rossanis: Yeah, like a few. Maybe we'll talk about that offline.

12:38 Cheryl Mack: The old anti-portfolio.

12:40 Maxine Minter: Yeah, exactly.

12:43 Tim Rossanis: I think, you know, having exposure to a business like Uber that's scaling rapidly means that you have a really clear understanding of what good looks like from a talent scale perspective, like seeing risks, being able to see around corners. I think all of that is beneficial, but then, you know, we've got people who invested in Nullarbor who also like have backgrounds at Amazon or management consulting and, and you just get a diversity of thought and perspective that I think allows you to make better decisions. And then, you know, for me, like the, the ex-Uber mafia, if you want to call it that, not quite PayPal, but, um, in Australia at least, like a lot of super strong people that have gone on to do really interesting things has been a great form of deal flow and a great form of just general networking. You know, one of the companies that After Work invested in, Clickert, is being run by Chris Withers, who's a phenomenal ex-Uber founder doing doing amazing things in Southeast Asia in the, you know, food space. And I think there's just so much that you get from spending a long time like deep in the problems that allows you to make better investing decisions.

13:51 Maxine Minter: I think that view of like getting a front row seat on what good looks like is just one of the most important things that any new angel can do.

13:59 Cheryl Mack: 100%. I think the same, the high watermark of execution, like the high watermark of operating a company is Like, it's almost like magic when you see it for the first time. And it's hard to imagine that it's possible if you've never seen it. And so I think like, if you've never seen what that kind of level of execution looks like, Uber in particular, right? It was such a, like, so much of the Uber alumni have gone on to run these like, sometimes very operationally complex, but just like excellent execution. Like, if any place coached just like, move fast, be a savage, take, like, no is never an answer. Just incredible, incredible coaching environment for those folks on like excellent operational skills. It's very, very cool to see.

14:44 Tim Rossanis: Yeah, yeah, for sure. I mean, like, you know, some of the values were big bold bets and just get shit done. And I think to your point, Maxine, like you see the kind of best operators operating in a super challenging environment. It makes a huge difference of, you know, understanding That because at the end of the day, like, you don't want to invest in average companies. You don't actually want to invest in above average companies either. Like the way power law works, you actually only want to invest in companies that are like top 1% in their field. And most of that comes from talent that themselves are top 1% in their field. And I feel super privileged that I've like seen that in action time and time again in some of the amazing, brilliant people that I've worked with. It's had a huge impact on me and my ability to grow and learn and develop as an individual, but also now as an investor. I have an idea of what, like, when you interact as an investor with people who are at that level, it's very clear that they're super strong. It's actually the inverse of that that I think is really valuable. It's like when you meet someone who might have a great idea, but they themselves just aren't up to scratch, it's a very easy no. And we made a lot of investment decisions where we decided not to write a check, primarily because at the early stage where we tend to get access, most of what you're investing in is the talent and their ability to scale the business and to like prove maybe not even product market fit, just, well, probably just product market fit, let alone, you know, scaling. And so I think that's really what one of the big lessons that I got from working at Uber.

16:23 Maxine Minter: I did that too much in the early days where I didn't invest enough in the people and got excited about the idea. And now I'm like, oh, that is, that is, I wish I could go back in time.

16:34 Tim Rossanis: I know, right?

16:36 Cheryl Mack: Such a valuable learning. Yeah.

16:38 Tim Rossanis: You just start again every year and you're kind of going back in time, right?

16:43 Cheryl Mack: Yeah. Right. Everyone is a new decision. Yeah. You definitely shouldn't be chasing your losses from previously, but I think it's important to learn. I mean, along as you go along that journey.

16:53 Tim Rossanis: Yeah, for sure.

16:54 Cheryl Mack: And so as you're thinking about like taking some of these learnings that you previously got from Uber and then now what you kind of see play out both in the kind of ecosystem from your vantage point at Turo, like how do you bake that into sourcing, to evaluating, to picking, and maybe even supporting on the other side? Do you leverage, like, are these, is operating and investing two completely separate tracks or is there actually cross-pollination so you get strategic benefit across both?

17:23 Tim Rossanis: I think there's a little bit of cross-pollination, but I probably see them as fairly distinct. You know, like, I think that the overlap is in the network that we individually have and then being able to give that network to founders or kind of portfolio companies when that's relevant. But we tend to take more of a, like, pull model with founders. We don't want to be those tiny little investors who are asking annoying questions or undermining the founder or second-guessing them. Instead, it's like, we're here, we're available, but, and come to us if there's something that we can do to help you. But otherwise, you know, we'll happily kind of exist in the background and only weigh in when we think there's something that we can do that's genuinely helpful. The other day, an investment that we made into EverLab, like I had a fairly interesting point of view on some of what they were doing and some of what they're competition are doing. And so I wrote like a long email to the team and said like, hey, take it or leave it. This is my perspective. That kind of thing. Or I've got talent. I see you're hiring for a role or you need an introduction to this company. I can help you with that. But most of the, like, I don't know if you guys disagree with this, but I think this concept that angels can be deeply supportive to their portfolio companies at my level, where we're writing like $10,000 checks max, I think we wrote a $25K check once to one company. We're not. We're not like making or breaking their round. And I think it's a bit of a fallacy to expect that we're making or breaking their business. We're helpful if we can be helpful. But otherwise, I think like angels who are super strategic, I see that as a little bit of an exception rather than the rule. Now, it can be an exception to such a degree that you go and like start a business and become, shift from like angel part-time to a professional, like kind of you both have done. But I see you guys as both also like exceptional and the exception compared to most angels who do what I do and like operate in the background and help out if we can. But otherwise, you know, we've got day jobs and that takes up 99% of our energy and attention.

19:32 Maxine Minter: Yeah, angel investing can be a day job all on its own.

19:35 Cheryl Mack: That's very nice of you. Heart hands for folks that can't.

19:37 Maxine Minter: Yes, heart.

19:38 Cheryl Mack: Yeah, I mean, I think that's so true to normalize because I think I, as you exactly as you said, if you try too hard as an angel to be helpful in a vertical commerce, you actually, and we've talked about this a lot on this podcast, like you actually just end up smothering the company and it's less, you're like detrimental as opposed to helpful. And so I think that pull model, like being really clear about where you add value and communicating that to the company and then them letting, letting them pull either through the ask sections of their investor update or directly to you, I think is definitely the go-to move.

20:13 Tim Rossanis: I think so. I think the difficulty is like information asymmetry. And so if you're a founder that has quite a few angels, unless you're really good at sending structured updates, uh, where you're requesting help, which, you know, some people are, and honestly, a lot of, a lot of founders aren't, then you've got this network of angels that it's like latent potential that you're not activating. So I also think that there's a, it's like a bidirectional thing. It's not up to the angel to be the one that's adding the value. I think it's often up to the founder to be the one that's self-aware enough to know when to ask for help. And I think there's a high correlation between founders who ask for help and founders that succeed because they know who to go to. They know specifically where their weaknesses are, how to fill, and they don't have the, like, this bullshit pride, like, I can't ask for help. I need to show strength. I think we all know that that's just a load of crap. And I think the best founders are like—

21:05 Maxine Minter: What's the point of taking angel money if you're like, I don't need any help? Well, then, like—

21:11 Cheryl Mack: I don't need you anyway. Yeah.

21:15 Maxine Minter: Then you may as well go get a bank loan.

21:18 Tim Rossanis: Exactly.

21:20 Cheryl Mack: Morgan, do you have— I guess a tip that I've seen that I really like and baked into the way that I angel invested early on was be clear about the places that you think you can be value add to each of the port— like the companies that you invest in and like on close of your investment, send them an email and be like, hey, I'm here for anything that you need. Like, feel free to ping me with anything you need. But recognizing like, that's probably not context you're going to keep in your mind. Here is a like menu of things that might be helpful for you. Like the way that I support in these ways, the intros to these kinds of people. And then the hope is that when they're thinking about how do I solve that, that email pings. And I've got some feedback from a bunch of companies that I invested in as an angel.

22:03 Maxine Minter: I do that.

22:03 Cheryl Mack: It's so helpful. They're like, great. I know exactly then how to use you. Like I know what tool you are. My toolkit as opposed to being like amorphous blob, which I don't know what to do with.

22:13 Maxine Minter: Yeah, I think I told you that, or I was like, I send an email with like a bunch of stuff including here's how I'm helpful, here's my LinkedIn, like direct link to my like connections if you wanna go through it. And I also like put my t-shirt size and address for any swag. And so like everything's there.

22:28 Tim Rossanis: All the important things.

22:31 Cheryl Mack: Not that I'm asking, but would like a t-shirt from you. If you haven't already got swag, now would feel like the right time. To send swag my way.

22:39 Maxine Minter: Right? I was like, well, I just invested that, like, if you have any swag, just ship it on over here because part of my value is I wear your shirt, you know?

22:49 Tim Rossanis: Yeah.

22:50 Cheryl Mack: Yeah. I'm a walking billboard.

22:51 Tim Rossanis: My wife said that to me yesterday. She was wearing a Turo t-shirt and she was like, do I get paid for this? I'm like, no, you get clothed for this.

22:59 Maxine Minter: You're welcome.

23:02 Cheryl Mack: I love that. Yeah, I get that.

23:04 Tim Rossanis: Do you have more t-shirts than Rainn at this point, or is there like a battle, or is—

23:08 Maxine Minter: I do not. No, no, I don't think I could ever win against Rainn, so I like, I'm, I'm not aiming to try, but I think I'm gonna go for quality over quantity at this stage because obviously, like, have you seen his, his— he got, he literally got one of those like the, the things you see on like little commercials on Facebook where it's like slot your t-shirt into here. He got those and, and then ordered them all in like color differentials and has those like that IKEA Kallax thing that's like 5 squares by 5 squares. It's nuts. No, I'm going to go for quality. So, you know, in 5 years' time when somebody exits, I'll be like, look at my original this company shirt.

23:47 Tim Rossanis: I love that. Yeah, we should actually— it shouldn't be about the quantity of the t-shirts. It should be about the value of the businesses. And maybe, maybe on that basis you'll, you'll take them out.

23:56 Maxine Minter: 100%. Right.

23:57 Tim Rossanis: I'm also an investor in Archangel, so I'm not necessarily rooting for that.

24:00 Maxine Minter: I am also an investor in Archangel, so Yeah.

24:07 Cheryl Mack: Let's hope everyone wins. Can everyone win? I'm hoping for an everyone situation here.

24:12 Tim Rossanis: Isn't that so like the Australian ecosystem as well? Like it's such a friendly ecosystem. Mostly people are like often rooting for each other to be successful. So I think that's a nice thing.

24:23 Maxine Minter: Yeah, we already punch above our weight when it comes to number of unicorns. So I don't see why that can't continue.

24:27 Tim Rossanis: Agreed.

24:28 Cheryl Mack: Yeah. And liquidity. We are punching way above our weight, which is awesome to see. Actually, that's probably an interesting jumping off point. You obviously, especially your role at Turo, you get to see across a bunch of ecosystems. Now, you spend time in the US. Would love to know kind of what you see are the major differences from your vantage point with the kind of operator angel hat on across ecosystems. Do you just deploy in Australia? Do you deploy elsewhere? How do you think about that?

24:54 Tim Rossanis: Yeah, we have really only deployed in Australia, mostly because we live here and the majority of our deal flow came, you know, to us via Australian operators. I do think there are some really distinct differences though, although more of what I see is the operator lens to that rather than the investor lens to that. I mean, it's quite clear despite the liquidity from, you know, Canva rounds of exits and, you know, other big businesses that are in the process of either, you know, selling secondaries or exiting completely. I think we're seeing an increase in the number of angels in the ecosystem, but not necessarily the commensurate increase in the amount of technical talent in the ecosystem. And so what's going to happen if you take the longer view? Are we going to be able to sustain with the amount of funding, not just from angels, but also the hundreds of millions or billions of dollars being raised that's supported a lot by institutional funding. Are we going to have enough technical talent to develop a sufficient number of really strong businesses in the next like 5 to 10 years in this ecosystem? That, that's something that I'm a little worried about, that I think markets like the US, much bigger population, even like India where they have hundreds of thousands of engineering graduates a year, it's, it's kind of hard to compare us to that even though the, the like relative funding on a per capita basis in Australia is super strong. So, I think there's a lot that actually needs to be done, like, at an infrastructure level to attract more talent back to Australia. I don't have any really good solutions, but it's very clear, like, I talk to friends who are trying to hire, you know, engineers or even sometimes in product, and you're, I don't want to say you're scraping the bottom of the barrel, but the big businesses that, you know, like the Canvas and Atlassians that pay really great salaries that are a lower risk opportunity for someone unless they want to specifically take high risk and get that significant upside, which some people do, thankfully. I think that that's actually a bit of an existential threat. Like, if I'm, I'm an above-average engineer, am I going to go take a $400,000 job at Canva with a couple million bucks of equity, or am I going to take a $150,000 job at this pre-seed business X with much more equity but also a huge amount more risk? I think that's a really big threat to our ecosystem. And I think we need to talk about it because otherwise we're not going to solve that problem.

27:24 Cheryl Mack: I mean, I think it is a, it is a continuing risk in the US ecosystem, right? Like you have this, but on steroids. Well, sorry, you have that element where you can go and work at OpenAI for $2 million a year plus equity, like cash out and then plus equity. Or you can go and work at like name pre-seed company starting, you know, at the very, either as like a founder or a founding engineer or a founding operator. And so it just lifts the bar. I think it's one of those things in the ecosystem that I think is a— it's hard and it's a forcing function for quality that I think is really productive. I totally agree with you though, that I think a perverse impact of the ESB CLP infrastructure in Australia is you have a direct incentive for capital to be deployed only into Australia. And actually the folks at Pitchbook I was talking to them when they were doing research on the Australian ecosystem. They flagged this. They were like, why do all of the Australian funds obsess over Australian companies only? Like, why are they not allocating outside of Australia? Like, why is it in all their messaging? Like, why are they so referential, you know, self-referential? Because in America, that's not the case, right? There's very few that have been like, America only, like the American dream. It's a very patriotic place. I was like, oh, I think it is a structure, right? Because of the ESG CLP and 80% of your capital has to be allocated to that. So I think like, it's well-meaning policy and I think was excellent to get us to here, but I do question whether it gets us to the next stage without creating this like overinflated internal bubble focused, like Australian capital focused in on itself.

29:00 Maxine Minter: That must actually be super odd from the outside to see that. I can only imagine, like we've been in that bubble, so to me it's totally normal, but you're right. That must like coming from the outside, you'd be like, that is Right.

29:12 Cheryl Mack: Yeah. Like, literally, they were like, why, why?

29:16 Maxine Minter: Why? Why?

29:17 Tim Rossanis: The other related problem is like, you've got companies that have had a lot of success in Australia kind of shifting their listings to other, other kind of indexes, and they're shifting their headquarters to other markets because of, you know, more favorable taxation schemes. And so I think it exists in a couple of different dimensions and we really need like strong policy leadership to help solve some of these problems because otherwise we're just going to see companies get to a certain level of scale and then they've got these incentives to shift elsewhere. That would be a really problematic thing for our ecosystem if we continue to grow in a positive direction and then you don't reap the rewards as businesses get to scale because they end up leaving the ecosystem altogether. I think there's a little bit of risk of that too.

30:04 Cheryl Mack: Totally. Yeah. I do also think that maybe the optimist in me is these are excellent. They're the kind of problems you earn the right to have once you get to a certain level of maturity of an ecosystem, right? Before, the problem we were solving was like, get the ecosystem going. Now I think, you know, the call to action is like, hey, especially policy leads, like you wouldn't mind just popping your head out of the sand a little bit and realizing like the tech ecosystem has an enormous amount of value to bring to Australians, right? You could probably, I know I've ranted and raved about this a lot, but definitely like the combination of Canva, Atlassian, Culture Amp, Misty Yum, or now me and you, Linktree. If you collated all of them together, you would be able to see them on GDP, probably on the FDI alone, the foreign direct investment alone. And like there's way more coming down the pipe. For that. I don't know why policy, like politicians and policymakers still have their head in the sand about it, but that seems like something that's worth accelerating. And so, you know, having policy that now matures and a, you know, a stock exchange and an investing, like growth stage investing and listed investors that mature into that ecosystem and they're allocating, recognizing that this is coming down the pipe and like building the rails before that steam train comes, I think would be excellent in the same kind of foresight that they showed kicking off the ESB CLP and tax incentives to kind of catalyze the kind of Gen 2 of venture in Australia post-Atlassian. So I'm hopeful that they'll read the writing on the wall and start making those changes. I know the Tech Council and folks are doing some work there, but it would be great to see a maturing of our infrastructure around the maturing of our ecosystem because it's coming in. thick and fast.

31:51 Tim Rossanis: For sure. Couldn't agree more.

31:54 Maxine Minter: So I guess speaking of what good looks like and achieving scale, maybe take us back a little bit to like, you know, the inspiration and founding story behind Turo and maybe how it's made its way to Australia and how you got involved.

32:07 Tim Rossanis: Yeah, for sure. I mean, Turo is like a fairly old overnight success in many ways. It was founded in 2010 in Boston as a business called RelayRides. And the founder had this insight, like walking down the street, it was snowy, he needed a car, and the closest traditional car rental depot was a long way away. And he thought, well, why am I not just booking a car that's right next door to me? You know, there's the car on the street, the house next door, my neighbors, why not start this thing called car sharing? And really pioneered the idea of peer-to-peer car sharing. And then we, when I say we, Turo, um, scaled the business pretty significantly in the early days on a model that was much more focused on, uh, hourly and daily bookings. And then in about 2015, had this insight at the same time as the business rebranded to Turo, that, uh, there's a lot more success if you pursue a longer duration strategy that's more anchored to travel. Not necessarily luxury, although building unique selection that includes types of vehicles that are a bit more aspirational make it a little easier to market the business and, and attract people's attention. And so really shifted towards that travel use case, uh, as they rebranded to, to Turo. Anyway, grew, um, very fi— very quickly got to a point of, uh, expanding to Canada in 2016 and then the UK in 2018. And then in 2022, acquired a business in France and then decided to launch the business in Australia. Australia was obviously an interesting market with Car Next Door and, you know, the car sharing wasn't necessarily new to the Australian ecosystem, unlike some other opportunities that we had to expand into markets where we would have had to build, you know, not just the business from the ground up, but actually make the market as well. And so I, I got a phone call from a recruiter in mid-2022. I was at Uber. I was actually on holiday at the time, and they said, like, we've got this opportunity to run a really interesting business in the mobility space. You'd be the local boss running the strategy, owning the P&L. Are you interested? And I'd spent 5 years at Uber kind of always reporting into the GM, and I felt ready to take that step up and kind of be the GM myself. So obviously, I said yes. And In August, I joined Turo and we built the plan to launch the business at the end of that year, which we did. It was like an incredibly successful launch. We built a lot of hype. One thing that you learn investing actually is the benefits that, you know, some of the founders who are really good at building hype get a lot of press attention. They get a lot of investor attention. I'd seen that playbook play out time and time again. Not always correlation between businesses that have a lot of hype and businesses that are actually fundamentally good investments. In fact, sometimes that correlation is kind of inverse, but Nonetheless, we wanted to have like a big bang launch. It was funny though, because around the same time that we were launching Car Next Door, Uber decided they bought Car Next Door and then they decided to rebrand it to Uber Car Share and do a whole bunch of like marketing activity on the same week that we launched, which was kind of funny.

35:27 Maxine Minter: Do you think somebody leaked that to them and it was strategic or just?

35:31 Tim Rossanis: No, no, they knew when we were launching because we had to, you know, you've got to build the marketplace and a big part of building marketplace is acquiring supply. So, we had this period of 6 to 8 weeks before we launched the business where we were trying to build the supply side of the marketplace to solve the cold start problem, which is a great book, by the way, by Andrew Chen, if you haven't, if you haven't read it. Also, it's a great book.

35:51 Cheryl Mack: It's so good. Yeah.

35:52 Tim Rossanis: Yeah. 16Z, I think. Anyway.

35:55 Cheryl Mack: Yeah. He's, yeah, he's 16Z.

35:57 Tim Rossanis: Brilliant. Anyway, so I'd like read that book multiple times and knew that we had to build the supply side aggressively before actually launching the business. So that's why Uber knew when exactly we were launching and they decided to put their activities at the same time. I was kind of proud that they like hung a disco ball, like a disco ball themed VW Beetle from the Opera House, from the Harbour Bridge. And it got very little press attention and we had this big launch event and got much more press attention. So at the time I thought that was a—

36:26 Cheryl Mack: Well done.

36:27 Tim Rossanis: A good little achievement. But it was cool, you know, we had We had Vance Joy perform at our launch party. I forget, were you at the launch party, Cheryl? I can't remember.

36:36 Maxine Minter: I wasn't. You invited me and I tried to convince my family to change our flights. I was literally willing to spend like hundreds of dollars to change my flight just to be at that party.

36:46 Tim Rossanis: It was a lot of fun. But it was cool because Vance Joy, like this was written up by Nick when he was still working at the SMH, that he told this story of when he was writing Saturday Sun. He was living in Los Angeles and he would rent a car on Turo and drive up into the mountains just to get inspiration for the music that he was writing. And around that time, you know, ostensibly while using Turo to get around, he wrote one of like definitely my favorite Vance Joy song. So that was really cool. And I think it just created this buzz around the brand, like, wow, this is like quite an inspiring business that's really doing a lot to shake up their industry. Yeah. And then things have been growing very rapidly since. We're now like 25 people in Australia and have learned a huge amount and had a lot of fun along the way.

37:31 Cheryl Mack: Love that. That sounds like an incredible journey, right? I think it's amazing the slow burn overnight successes and the businesses they build. And like kudos to you for building buzz around the brand as it launched. That's amazing. I like just the fact that Advanced Story was using a Turo to kind of get around. It's super cool. So maybe the kind of last one I'd love to pull here is how do you integrate those two things, right? Like you're getting learnings, you're getting insights, you're getting networks from angel investing, and how do you integrate those back into Turo?

38:05 Tim Rossanis: Yeah, I mean, for me, I think a lot of it is just about like being open to opportunities, being present, being interested, and like taking a big bet when the opportunity presents itself. Like, I remember before actually launching Turo, not long after I started, Afterwork was hosting this masterclass in growth marketing and SEO. And I very often like sign up for these things and don't turn up. That's kind of a bit of a dumb thing that I tend to do. Like, I don't want to miss out, but then something else will come up and I just won't always go along. But in this case, it was this marketer who was also involved in Afterwork, Anna Chang, who I'd seen a bunch of her material and I thought like, wow, she's a great operator. Like I want to learn from this person. So I joined the masterclass and she was phenomenal. And so after like a month, I listened to the masterclass. After about a month, I like sent her a message and said, you know, we're about to hire marketing roles to launch Turo. She was at HealthMatch at the time. I don't know how things exactly were going at HealthMatch, but I think the timing was great and she was interested to— potentially take on a new opportunity. And she ended up joining as our head of growth marketing, is on my leadership team. And, you know, we've been working together for 2 years now on the back of me just accidentally deciding, you know, I'm going to go to this masterclass that Afterwork put on. So I think that kind of thing is really cool. And you just meet some phenomenal people through angel investing. A lot of them, you know, whether they're founders or investors, are people who are just willing to like push the boundaries and do that extra thing, like go harder than anyone else. You know, a lot of it is before work or after work and and you have to make sacrifices to be good. And so I like to surround myself with people who kind of fall into that category. You know, like even just the two of you. I remember in preparation for this, I was trying to think like how—

39:53 Maxine Minter: I was at that.

39:54 Tim Rossanis: You were at that masterclass? Oh, cool.

39:56 Maxine Minter: I was at that masterclass. Yeah, I remember. And I think you were like, oh, like Anna Chang's awesome. Like, yes, 100%. If you can get her, do that.

40:04 Tim Rossanis: For sure. And he did it. I was looking back at when we met because it's good to tell the good side of the story, but then the less good side of the story is also interesting for people. So the good thing—

40:14 Maxine Minter: When we met?

40:15 Tim Rossanis: Oh, wait a second.

40:17 Cheryl Mack: I'm so interested to see how this plays out.

40:20 Tim Rossanis: The good thing is we met and have now known each other for 3 or 4 years and worked together a bunch and obviously love you and you're amazing. But we met on Clubhouse, which did not succeed, like billions of dollars.

40:35 Maxine Minter: We did meet on Clubhouse. I have actually met several people that I've gotten great value out of on there, and then it went down, like it was so high quality and then it went downhill so quickly. That's hilarious that you remember that.

40:47 Tim Rossanis: Isn't that insane? Well, I didn't remember. I went back into my emails before this podcast. I was like, when did I meet Cheryl? Because I remember when I met you, Maxine, it was through Cheryl when we did that panel at like the UNSW Founders. Yeah, yeah, yeah. And then we went and got lunch. And anyway, I just think it's funny, the people that you meet in the ecosystem and the relationships that you build. And then it's like years and years of, you know, brilliant relationships, and it's fruitful. And so I think it's funny, the like good side of that, which is the relationships. And then like, it's on a platform like Clubhouse that completely shat the bed.

41:21 Cheryl Mack: RIP Clubhouse.

41:23 Maxine Minter: RIP Clubhouse.

41:26 Cheryl Mack: Oh, thank you, Clubhouse.

41:28 Maxine Minter: Thank you. We can thank it for its joy. Thank you for your Thank you for the joy.

41:33 Cheryl Mack: Marie Kondo Clubhouse.

41:35 Maxine Minter: Yeah, exactly. I'm Marie Kondo Clubhouse. Thank you for your service.

41:39 Tim Rossanis: Now you put it in a box and put it in a shelf and don't think about it again for a few years.

41:44 Cheryl Mack: I wonder if the investors in Clubhouse did that. Okay, it's not going well. Just gonna put it in a box, compartmentalize the disaster and just put it up on a shelf. Oh dear. Well, that was, it was an incredible product for a short period of time. It's a very, I think, educational on like network businesses and probably something quite close to your heart, the Uber side. Gosh, I feel like we could just continue chatting, riffing for hours and hours. I'm conscious we have already taken a load of your extremely valuable time. So we always ask the same question at the end of each of these sessions. What is the biggest big cajones moment you've had? A moment where you felt super brave.

42:23 Tim Rossanis: Oof. I mean, there have definitely been a few, like transitioning out of Uber, which I loved. I loved the people, I loved my role. I was making impact and had a great team. And so that transition to Turo was definitely, excuse me, a big honeys moment. But I'd say probably the biggest one, I don't wanna get too political, but you know, last year, there was, you know, towards the end of the year when the October 7th kind of massacre happened in Israel. I, you know, I'm Jewish and I'm very proud of my my Jewish heritage and my dad is Israeli and I was deeply affected by that. My sister lives in Israel and in the months after that, there was a real resurgence, sadly, in kind of hatred towards, I mean, not only Jews, I have to say, like hatred towards quite a few marginalized groups in this country and underrepresented kind of minority groups. And I just, I couldn't sit by and do nothing about it. I remember I was on a flight, I think to Perth actually, like a 5-hour flight. And I was like on the window and sometimes I'll sit on the window on a flight and just like think for hours at a time and do nothing. And I had this idea, which we ended up executing upon, to write an open letter from business leaders in Australia to the Jewish community in Australia to say, we stand up against antisemitism and we reject anything that tears the moral fabric of this beautiful country apart. Multiculturalism and acceptance and just being kind to people is a big part of Australian culture. And me and a lot of my friends at that time felt not necessarily not supported, but I think it was very hard for people who operate in business to know what to say and how to say it and not to offend anyone. And so, we set up this campaign. There was a group of us who used our networks to get hundreds of CEOs across some of the biggest businesses in the country to sign this letter to say, we stand up against antisemitism. It was in all of the major newspapers. It was, you know, front cover of The Australian and the AFR. We took out an ad in, in all of the kind of Australian kind of, yeah, News Corp newspapers and in the Nine newspapers. And it was really successful. I'd say in a moment of difficulty in making, I think, the Jewish community feel like we are accepted in this country and we have a place here, and that the antisemitism that had reared its ugly head was really just the vocal minority, and that the majority of Australians, certainly the ones that we interact with, supported us and love us and don't want us to feel in any way rejected by Australian society. So I think that was— it was risky. It in many ways to, you know, like stick your head above the parapet in that way. You know, I had to go on ABC and get interviewed by PK, and she's asking all these intense questions about the political situation. This wasn't— it wasn't a political thing. It's like a human thing that people deserve, especially in a country like Australia that has such a big emphasis on multiculturalism. People deserve to live their life the way that they choose to. So, I was very proud of that, to kind of lead that effort on the back of of a random flight idea that I had. I got to interact with some amazing people that I still have great relationships with now that are at the kind of top of their fields in business and politics and share those values. And, you know, I think it's important to, when you see something that's problematic and it kind of affects you and affects others who you care about, I think it's important to try and do something about it. So I was glad that I took that risk.

45:56 Cheryl Mack: Wow. It's so brave. I honestly, I had no idea you were behind that. I saw that happen and I thought it was just such a like love-filled communication in a moment which I think really needed it, and it was beautifully executed. And that kind of like shining ray of light out in a moment of fair darkness, you know, and political darkness. So super brave. That's a great one. You should be really proud.

46:22 Tim Rossanis: Thank you. Appreciate it.

46:24 Maxine Minter: Well, thanks so much for coming on.

46:26 Cheryl Mack: This has been the best. I feel like we could just do this forever.

46:28 Tim Rossanis: Thank you guys. This is a lot of fun. Always great to catch up with both of you. Hopefully we'll do it in person at some point soon.

46:34 Maxine Minter: Yes, can we please?

46:35 Tim Rossanis: Please, we have to. Cocktails.

46:38 Cheryl Mack: Cocktails.

46:38 Maxine Minter: Not enough Tim in my life, but maybe bring Vance Joy.

46:41 Tim Rossanis: Okay, yeah, I'll send him a message and see if he's available.

46:44 Cheryl Mack: Thanks, Tim.

46:46 Maxine Minter: Thanks, Tim.

46:47 Cheryl Mack: Bye.

46:48 Tim Rossanis: Cheers, bye.