Gopi Sara initially came to Australia at the turn of the century as a refugee from Sri Lanka. After studying engineering, Gopi spent 8 years at McKinsey as he began his angel investing journey. With 30 startups in a portfolio that focusses on B2B SaaS, Gopi has joined Series B scale up OfferFit, after angel investing during one of their earliest rounds.
🔑 Came to Australia as a refugee from Sri Lanka in 2000, studied engineering as pathway to citizenship.
🔑 Worked at McKinsey where he was exposed to startups, tried his own rental marketplace startup idea in 2013-2014.
🔑 Started angel investing in 2020, now has portfolio of around 30 companies.
🔑 Now focuses specifically on B2B SaaS startups, where he can leverage his experience and interests to add value.
🔑 Initially invested in OfferFit, before joining full time as a Director, as the company has completed it's Series B round from Menlo Ventures.
🔑 Views founder qualities as most important criteria in DD, looking for missionaries solving genuine pain points they've experienced.
How long have you been angel investing and what’s in your portfolio?
So I started about 2020. So the past four years. I've got about 30 angel investments now.
We're going to delve deeper into that, but let's just start broadly with your background. Who's Gopi? Where did it all start
Look I came to Australia as a refugee. I came here in 2000, as a refugee from Sri Lanka.
I studied engineering because that was the easiest path to become Australian. I think after graduating and working as an engineer for four months, I like left engineering and went into a different career path and strategy. I worked for a Swiss firm for a bit and then I joined McKinsey for a long time.
And I was like there six years the first time. And I think two years, the second time. And while at McKinsey is where I really got exposed to venture. We used to have startup labs where we used to have a lot of startups who used to come in and we used to do problem-solving sessions and try to help them out with various things.
Matt Pauls and a couple others came through. That program and then yeah, I tried a couple of startup ideas and got exposure that way too, like back in 2014, 2015.
I'd like to double-click on the McKinsey thing. What do you see as transferable skills from being a consultant to bring into your angel world?
I think you just get pretty cut through in terms of what matters. So you can ask the question of what are you trying to do? What's the problem you're trying to solve? Why now? Why you what does the competitors look like?
You get to the nitty gritty of I guess what the what the company is trying to do. And you try to get an evaluation of whether you think that there is something there worth going after.
And then there's a few things you probably haven't touched on there. You tried your hand at being a founder.
Yeah. Like a buddy and I, we tried to do this rental marketplace back in, I think, 2013, 2014 what turned out to be a terrible idea. That was the first time I actually got exposure to the VC network as well. By random chance, I was selling a pair of headphones on Gumtree. And this guy emailed me and was like, “Hey, I'll try to buy the headphones off you”, et cetera.
I held on price a little bit and he accidentally emailed me from his work email and it was Gary Visontay from Right Pick capital. And so I like looked him up and I was like, “Hey Gary, I'll give you the headphones for free if you just have lunch with me”. And he obviously looked me up and he is like, “Hey, do you wanna meet at the bottom of the McKinsey office?”
Yeah. And so my buddy and I went and had lunch with him and yeah, that was the kind of the first time I got exposure to the VC world. I got captivated by it and always yeah, that's a path that I always wanted to try to pursue, but I just didn't know when and I didn't know the path or anything like that.
So everything, where I'm today, et cetera, was all through just, I reckon, luck and osmosis and just, being at the right place at the right time.
There's certainly a lot the startup ecosystem where you've just got to expand your network and just, you know, spread the load and see what sort of double down and delivers for you, right?
Yeah, exactly. Cause even so then from that I attended a few startup comps and things like that. A few friends and I, we won a startup weekend where Tony Abbott came in to the River City Labs. And, Tony then put us in front of Courier Mail for our particular startup.
And that's how I met Steve. And then I did a bit of pro bono work with Steve (Baxter) while I was at McKinsey. We had a bit of time that we could use. From certain organisations. So I use it for River City Labs. And yeah, then from there, things just added and compounded.
Some of the early investments into your 30-odd portfolio, did you have a strategy about how you were picking them in the early days?
I think the early days I had a basic idea. I read, Peter Thiel's Zero to One. So I had a basic idea of like power laws and how to spread the bets.
And, Steve Baxter always talked about, stories of many people going all in on one and then losing it and things like that. So I had a basic idea of from a process point of view of, How many investments I wanted to make, how I wanted to double down, et cetera, but I didn't really have a strategy in terms of a specific area or a how to source deals or how to even evaluate deals.
So my first investment was Chipper Cash. So yeah, I signed up to the TEN13 platform at the end of 2019 and then Yeah. In 2020, I think Chipper Cash came through the platform and I jumped on a call with An, and I was like, oh, this sounds like a great opportunity.
And that was like, yeah, my first investment.
All right. That's been a wild ride and suddenly getting in at the early days into that one.
Yeah. I'm not even sure if that classifies as an angel investment cause it wasn't a direct investment, but it was my first venture investment anyway.
No, that definitely counts. And what are some of the other resources you lent on in the early days as you were forming a strategy?
I did a bunch of programs. I did Jason Calacanis's Angel University. I went through the Antler program myself.
Then I went through the Antler University. I did the first believers program. I did Brendan Hill's program down in Sydney, I think it was like UNSW. So I did a lot of angel courses and it was less around the content and it was more around the networks. I think that's one of the things I learned very early on was like angel investing or venture investing is all about the networks.
The more access you get, the more people you're connected with the better probability of deal flow that you get.
And so it's did a bunch of things to get into a bunch of different networks.
So is that sort of your deal sourcing strategy now? How are you finding deals outside of the TEN13 sort of syndicate platform?
My strategy has changed a lot, right? So when I first started, I had a basic idea in terms of like numbers and processes, like in terms of what I needed to have in my portfolio from a number perspective or the number of investments, but I really didn't have a strategy around the type of investment.
So then I invested in a bunch of different companies from. Chipper cash to AI startups to Fable Food, to a bunch of different things, a bunch of different industries. And then about three, two years ago, I started to realize you need that, like when you get spread really thin across multiple different industries, et cetera, you just have one zero chance to add any value because you, you can't be jack of all trades.
Cause you know, these founders know a lot and they're like cutting edge in the industry. If you want to add value, it's pretty hard if you're not deep into a certain thing. The second one is it's hard to do a DD on a investment as well. So a couple of years ago, I really honed into B2B SaaS.
And just especially in like marketing, AI-driven compliance, like that kind of space. And that's like where I've spent a lot of my time the last couple of years. And so that's where I get a lot of deal flow now, where people I'd know who are investing in that space will say, Hey, check this one out or have a chat with this founder.
I think they could, use some help thinking about their B2B sales strategy, et cetera. Yeah.
So why did you hone in on B2B SaaS?
I just enjoyed it. It was, yeah, it was like I think I made a few investments in that space.
And then as I was chatting with the founders and we were strategising and, I was helping them with introductions to the networks I had. I realised it's a space that I enjoy a lot and it's a space that I wanted to learn more about. And so it just made sense to overlap the personal interest with the investment as well.
Going back to that early portfolio, you said you had an idea about number of investments you wanted to have. You'd read some books and had some resources that suggested it makes sense to diversify and build a portfolio. What was the right number you were trying to get to in your portfolio?
At the time I think it was like Making 20 to 30 first round bets, and then doubling down on maybe 10, the difference though, was, the reality of how it all played out was in 2021, every company came back for a follow on round within a year. Eight to 10, 12 months. So what was supposed to be, was first round bets, 50 percent were supposed to not play out.
And then maybe, another 25 percent might come for like bridging rounds of the 25 percent might come for follow up around that's like growth. So you went, Oh, I'll allocate a bit of capital on the side to do that. But then what happened was when everyone's coming back, you're like, Oh, like, how do you not differentiate between who's winning and who's not the noise versus the signal?
So that became quite challenging and trying to work out, yeah. Where do you actually truly double down and where the winners are going to come from? Wasn't as easy. The other thing I changed to as well is that I went from having 100 percent of my capital allocated towards say direct investments to splitting it up a few ways.
I think about eight months in, I switched to having, so 33 percent direct 33 percent directly to funds. So I invested in Our Innovation Fund (OIF) and Second Quarter Ventures, and then 33 percent through syndicates like TEN13, et cetera. So that means that. I only had a I only needed to focus on a few investments direct.
I think trying to deploy the whole capital myself as well. It was just unrealistic. I just didn't have that kind of time to go out there and source deals. Whereas if I said, Hey, look, if a really good opportunity comes across comes my way, I would double down or I would invest. If not, I'm still getting venture exposure through other avenues.
And so the ones where you are going direct, you touched on it briefly with regards to mirroring your interest in B2B SaaS and probably your recent career experience in marketing, et cetera. You, what are those relationships you're having with the founders and the portfolios in those direct investments?
Yeah, it's interesting. They vary, that there are some investments where, the founder and I chat regularly, I would say like on a fortnightly basis, we're thinking through, opportunities, how to go after certain markets, how to position the product, et cetera, to ones where I just message them maybe once every three months, just saying, Hey, I hope you guys are going all right.
Or I saw this thing the other day, I thought you might be interested and then we might get on a call and chat. I think it's interesting as like an angel investor trying to find your spot in the founder's ecosystem, right? Cause you gotta imagine the founder has an advisory board, they've got employees, they've got other people that, you know that they're close with that kind of advise them as well.
So it's like sometimes that relationship comeback comes through organically. Other times it just doesn't right. Like they've just got other things that work through.
So I think when I make an investment upfront, I would just be like, Hey, this is what I can offer. This is what I can help. I would say for the. First couple of months, I would proactively send them things that I think would be helpful for them. If they engage, then I also we then work together on it.
Whereas if they don't, I'm also conscious, they're, working with a bunch of other people. So I try not to be annoying. I just try to make sure that I get an update on how they're going. And a lot of the founders these days are pretty amazing with their monthly updates and things like that. So you end up getting a pretty good idea of how the business is going.
And you mentioned earlier that you were looking at AI like many years ago. How, what's your current view on AI as a category or an industry to invest in?
I think traveling back from, back and forth from San Francisco as well, you just see there is feature type AI solutions that like could be obsolete, like within a month, a year, et cetera.
And then there's like people. Who are genuinely leveraging a lot of AI capabilities to solve, hundreds of millions of dollars of problems. Like I met a founder the other day she got a call from Coinbase. They've just heard about her and they were just like, Hey, we really need you to come in.
And then they had a couple of conversations and before she know it, they're like, Hey, look, we'll pay you a couple of million dollars to solve this problem because. The cost of that problem to them was like 200 million and she, as a founder got access to open AI two years ago, GPT 4, and she built a compliance solution.
And yeah, you see like this world where people are just building features versus people building true companies and having just flooded with inbound of all these people that want them to solve their problem. Yeah, it's a pretty interesting space. I think people underestimate how long it does take to solve problems through AI.
So people pitch that we can come in, solve it in a few weeks, et cetera. And then, three months later, people are still building a workable solution.
Obviously we're well and truly on the new AI wave. And I know we're thinking really deeply about how you back sustainable companies when it's just moving so quickly in that space.
Yeah, that's right. And I think it's like one of those things where, yeah, you just got to be open to make some wild bets because you just don't know how it's going to play out.
If we talk to the diversification within your portfolio that you've built, like that wild bets is a really interesting point you've brought up.
How do you have exploratory money or are you really disciplined in, valuations and other metrics you're looking for when you're going in early?
Yeah. It's interesting I think I'm pretty loose on the valuation side. I usually like where I'm really disciplined is around founder quiality. I've been fortunate to work with some great people throughout my career.
And so I have I back myself to know when someone is truly exceptional. And so that's literally my thesis. It's never, over the last sort of three years, I've never gone in and try to look at the industry and try to understand it and try to, make a judgment call, whether, this is something that's worth going after or not.
I usually spend time with the founder and hear their story. And if it's very obvious, they're an exceptional person that can go off to anything they want in life. But they've chosen this and you can hear the passion and you can hear why they have a unique perspective and they, why they believe now is the right time.
That's pretty much the DD I do. And usually you can get that in a couple of conversations. OfferFit was one of those companies that was very similar. George, the founder was on par with McKinsey. He could have quite easily done anything else in his life. And he chose, solving AI driven personalisation as it's a problem. And he talked about why they believe that’s a competitive edge. And, they just had a pitch taken an idea at the time I invested. And I was like, these are the type of people I really want to back. And I want to be in conversation with, and I want to be like a fly on the wall and the journey.
Yeah, brilliant. It's a fair bit of conviction as an investor if you then join the team, right?
Exactly. That's right. Yeah. And I think that's the best thing about venture investing is like, because of how the rounds and everything work is that what you're doing is you're really buying a call option.
You put in a bit of money to see, Hey, this sounds really interesting. This is a person I really want to back. You put in a bit of money in over 12 months, you realise like who that person really is and is there a real opportunity? And then you get to double down. And I think that's what makes it I think a viable path as well.
So would you call OfferFit a scale up?
Yeah, now we're like a series B company. It's a pretty cool journey. Like it went from, when I invested in 20. Yeah, late 2020. It was a yeah two guys with the pitch deck they landed their first customer. I introduced them to Foxtel in Australia, which then became one of their major customers as well.
And so any learnings you've gleaned from being behind the hood in one of these sort of hyper growth companies, on the execution side or on the go to market side that might be helpful for an investor?
Again, it's a bit different to early stage to late stage because early stage there's usually five people, 10 people, a pitch deck, maybe they might have a prototype stuck together with sticky tape.
I remember when I introduced George to one of the marketing executives from Foxtel and I was fortunate enough to sit in a call and George was pitching this idea of automated experimentation for life cycle marketing. And the marketing executive interrupted him like seven minutes in and was like, Hey, George, can I show you the slide?
And he had a slide where it was like manual AB testing here and AI driven experimentation here. And it was like a seven year journey. And he's Hey, if you can cut the seven years down to like tomorrow, like I'm super keen to do something with you. And that's when it clicked there is, yeah, sometimes there's a burning platform for the problem.
And some founders have really honed in on it. They know now is the time, they have the first early mover advantage, et cetera. And yeah, so I think working from the inside, there's one thing that I've realised is it really a painkiller versus vitamin? Because when you see a painkiller, it's really obvious. And when you see people playing around with like vitamins and stuff like that, you go yep, this is, yeah, this is going to be hard work.t
That's a good analogy. I like that. So if we talked a bit about your operator scale up experience, so it would just rewind a bit to the founder one you had how important was that journey, albeit potentially brief in giving you exposure and I guess empathy when supporting early stage companies and founders.
Yeah. Look it wasn't a, it wasn't a long time. I had to cut a few cracks at different things and even going through the antler program. Yeah. It helps you to empathise with the founder in terms of when they're trying something and it doesn't work out. Or, this idea of getting punched in the face, but then having to pick up all the pieces and have another, have another go.
It also just made me realise that as much as I'd love to, have a as much as I love to be a founder, like it just wasn't me, like I'm. I'm a great operator. I'm a great, my skill sets is great from taking things from say the first million to like the next 10 million, but going from zero to the first million, that just didn't suit my personality.
It was pretty funny. I went to one of the first All In summits and we were at the poker table and playing poker and I was chatting with this guy. At the time he was at DoorDash. He was pretty senior there, but before that he was at Box. And before that he was, I'm pretty sure at Airbnb.
And I was like, dude you've been to all these like blue chip, companies and startups, I was like, why don't you have, why haven't you done your own thing? And that's when he was talking about how yeah, he just realised he's just not a founder, right? He just he is a great, he's a great person to be in this startup ecosystem to help race, grow and build amazing companies, but it's just the founder thing is just not him.
And he talked about a few things and that really resonated with me. And so that was a good thing as well, which was like how going through that experience was just learning that. Yeah. Like the. Founder journey was something that at this point in life, or at this point, it's just, doesn't resonate with me.
Good on you for giving it a crack though. I love that. On you've spent more time than most of the investors we get to speak to in the US what are some of the things the Aussie ecosystem or Aussie angel investors can learn from what you've seen in your experience dealing in the US?
The market is just so huge there. If you think about the inbound opportunities the networks, the capital that's available, it's just insane. And I think sometimes it's um, raising yeah, what I've really seen is I've seen companies that I've invested in Australia, raising far rounds, and then I've seen similar companies in the U S how they raise rounds.
And it's sometimes it's like taking water pistol to a gunfight. It's with the behemoth of the capital they've got, but also they don't. Sometimes if they're in the bay, they don't really need to even leave the bay. They can hit 50 customers, over a three year period just from the bay.
And the capital that those customers have to spend their appetite to take on risk it's yeah it's just a completely different world. And so it's always amazing to see companies like Canva go one, et cetera, operate Alassian operating from an Australian world, from Australia to the world and really crushing it.
Because they, they're obviously really up against it.
You've obviously been on the journey here in Australia the past few years as well. Like, where do you see the Aussie VC and angel investing landscape going?
Honestly, I'm not too sure. I think there's a few things that Australia has going for it.
One is we have a very, like a highly educated ecosystem of folks coming out of universities and things like that, whether it's in the tech world or not we, we have three major cities where everyone congregates again. So the ecosystem is quite small it's quite concentrated.
And also we're also fortunate now where we're in a world where folks who are in Canva, in Atlassian and et cetera, leaving, starting their own company. So we're on the third, second or third generation of folks who are exposed to startups who are now forming their own thing.
So I think a lot of. Ideas, a lot of opportunities, et cetera, will come. And the whole thing, I guess now it's with the keyboard and mouse, you could oh, sorry, with the laptop anyway, you could yeah, you could found a company anywhere. And with the solutions that are available, like at a much lower cost as well.
Can you see the risk appetite in Australia sort of, further fuel, like changing and, people getting happy to lean into, high potential, potentially high risk investment opportunities?
I think so. I think if you look at like the funding from the super funds, if you look at the cohorts that Airtree and Startmate a putting through like the first believer programs, et cetera.
I don't think it's getting any smaller.
We'd love your sort of summary or like top three tips for anyone aspiring to get into angel investing.
I think it'd be very clear about your why. Like, why are you doing it? Is it investment return? Is it play money? Is it an opportunity to get closer to something that you're super passionate about? For me, it was definitely the latter. It was like something I really wanted to do. And I thought, Hey, I could yeah, take some of, the excess capital I've got and I could have, this is a way to get closer to that ecosystem.
Definitely your why being practical about how you're going to get deal flow. And yeah. And in that aspect as well, just realising how much time you might have to invest. Like you might have to go to the lunches, the dinners coffees with people. And then last one is being clear about what your value proposition is is as well.
I think it's yeah, it's like a two way street, right? You have to contribute as well. And so working out what you can contribute and having that align with the founder's need as well goes a long way.
That's some excellent advice. What do you think makes a really good angel investor?
Great question.
Honestly, I think it's just someone who, yeah, like I think it goes back to your point, right? Like I think so. Someone who really empathises with the founder. It's not like someone who's giving you a call every day, asking for an update. It's not someone who sends a introduction to a potential customer and then gets frustrated that it never gets picked up or something like that.
Someone who gives advice and then gets frustrated that the advice wasn't followed through. I think the founders go through so much, they've got a ton on that plate. Making the best decisions with information they have at hand, I think just being empathetic to that and yeah, at the end of the day, it's the founders journey and just giving them the breathing space to go through their journey.
Love that. And then, so who are some of the angel investors that you follow or admire or whose playbooks you've leveraged?
Yeah, there, I've been pretty fortunate, I think, even with the limited connectivity I had in the, Venture space starting off. That's what I love about the Australian sort of venture ecosystem is everyone's really keen to chat.
Everyone's really keen to share notes. Everyone's willing to mentor and spend time. So rain's been amazing over the many years to spend time, have a chat. Brendan Hill's been the same as well. I remember Brendan and I having a chat about. Chipper before I made an investment, there was a couple other ones where we've always traded notes.
Yeah, I think those two guys have just been yeah, like people I'll look up to. And I try to learn from when I think about venture investing.
So should we get Brendan on this next?
A hundred percent. Yeah. Yeah, definitely. I think, yeah, I think he's just done an amazing job over the last, I think, what, I Eight years for him or something like that.
And he's taken like, difficult bets. It's one of those things where, like when you're deploying randomly here and there, it's a bit different to someone who has made, like his full time job and almost deploying capital, personal capital as well. He's taking some hefty bets.
Yeah, he's really leaning into it, which is good. Curious of what your current view on the venture market is.
Honestly, I don't. I have a pretty neutral view. I think it's no different to any other last four years. There are some great opportunities coming out. There are some great companies being built and yeah, for those who are lucky enough to be in that deal flow, they see it.
And there's some great people building some great companies as well.
Now that's pretty promising. And then just to end it off, what are you working on at the moment that excites you?
I think for me, it's like, what's exciting for me was the journey that I've had, so I rewind. Eight, nine years ago, I was frustrated at work one day. So I called into the McKinsey HR team and managed to land an interview and then was there for a long time. And then I left and then I one of the angel investments was OfferFit.
And we were having a chat about, growth plans in Australia. And I helped them put a plan together. And I looked at the plan and I was like, Oh, this is super exciting. I want to do it. Year one was just, will I like B2B sales? Cause I'd never did it. And I was, when I was 19, I got told I should get into sales.
I was 34 at the time and I always thought sales was a dirty word. And yeah, after year one, I was like, this is amazing. Like I really enjoy this profession. And so year two was about how can I learn to become an elite, top 1 percent seller. And so for me now it's really around leverage.
Like how can I learn to close. Bigger deals. How can I learn to build, strong relationships with my customers and help them achieve their ambitions and help them get up there, all curves as well. And yeah, that's what I'm trying to learn at the moment. That's what I'm working on is like really learning everything I can under the sun about B2B sales.
You've been at it a few years and you've built a great portfolio and it's been really nice to have you as part of the TEN13 community as well. So thank you.
I've got so much out of the community. I think it's like one of the best things that happened to my life for the last sort of, yeah, five, six years.
It's been amazing.