Super Angel #258: Angel Investing with Harsh Sinha, CTO of Wise and angel in more than 50 startups and multiple VC funds.
36m 38s
Harsh, a builder with over 20 years of experience at eBay, PayPal, and as CTO at Wise, shares his journey into angel investing. He started by helping friends with their startups, but these early investments failed due to emotional bias and poor execution. To become more objective, he used AngelList to join syndicates, learning about founder evaluation, deal terms, and industry dynamics. This experience helped him develop a balanced approach where he invests in founders he connects with personally, but with a critical eye on their passion and ability to solve a problem over a decade. Harsh assesses founders by asking why they dedicate their lives to a problem, preferring those with a personal stake and a history of overcoming challenges. He invests broadly across sectors, though his background naturally biases him toward payments and marketplaces. Managing time is a key challenge; he uses expert networks from venture firms to filter deals, allowing him to support founders effectively while focusing on his full-time role at Wise. Harsh emphasizes that successful scaling often comes from founders with prior hard-won experience, not just great ideas.
in a world where podcasts outnumber humans. We try at EUVC to be mildly more interesting. tune in at EU.VC to watch this episode instead of just listening. EU.VC where the extraordinary is just another Monday. Welcome everyone to the Super Angel podcast. We're delighted to have you here today and we're even more delighted to have Harsh, seen how joining us. Welcome to the podcast, Harsh. Thank you so much for having me. Sridhry? No, it's not a dream. I'm an angel. I would God send me an angel. Because God knows that everyone needs a little coaching down there. I'm loving angels. I saw an angel sing for you. Please say it's me an angel. The small hooded face. Be in it to get back the dope, hope, me an angel. It says by an angel, girl. This show is not investment advice and the hosts of this episode may be invested in the funds and companies featured. Yeah, thanks for joining us, Harsh. I mean, eBay, PayPal, Lise. What experience is there? Excited to have you on and to share more. Do you want to start by sharing a bit more about your journey and what got you into angel investing in the first place? Yeah, so in the spring back, I've been a builder all my life, including products and different experiences for customers. So started off as an intern in 2004 time frame after the dot-com verse in the Bay Area. That eBay and then quickly moved to full time. And then through my journey, spent about 10 years building products at eBay and PayPal. And that was across a wide spectrum of things and problems that we solved for customers. So I started off as core engineering looking at how we scale applications and distributed systems. So looking more as a performance engineer. At those times, it was pretty cool that if you said you were a performance engineer at a web company, there were not a lot of teams like this on the planet at that time. I think they were like eBay, eBay and PayPal. Amazon had one Yahoo Hotmail, which was, you know, MSN and Microsoft. And then, I know a few other, generally, if you looked at web scale and web scale at Google, of course, had one, but like web scale was still coming up to, you know, the number of computers and number of transactions per second was still much lower than the idea today. But in the early days, there were very few companies which had separate teams looking at performance in scale on the internet the way we were. So it was pretty fun times, small team, but that helped me understand what it means to build an amazing performance product across the world. And then I moved that into actually building experiences. So spent time building parts of eBay Motors, which I'm a car enthusiast. So a lot of things that were close to my heart. Most people don't know this, but I think at that time, we had some numbers that 2.5 billion of GMV of eBay was a $5 billion business. 2.5 billion GMV was from parts and accessories. And then for it was from selling vehicles or getting leads to dealers. And we sold a part. So if you had a hoppy car looking for a part of 1965 Chevy, where would you go? You would usually go to your local sales with GR, which would be good luck finding that specific part. Or you go to one of the biggest market places where eBay had this. So there's a pretty big product and fast-wing product. So that was fun to build. It has a lot of intricate complexities now on how you build search on this. And then we're not going to build other products, including acquiring a company where we tried our hand at doing a local delivery product, eBay now. And then end up spending time from there to building the paper, trading the PayPal product with the PayPal mobile app. And then finally around 2014, Christian Tarlick, the founders of WISE, or TranswISE at that time, found me and started talking about me potentially moving from North to sunny. San Francisco to North to sunny London for a while to try and build and scale what now has become a pretty global company twice where we help people manage their finances and spend and receive funds across the world. One thing I realized, I did a segue in the middle and did it MBA at Berkeley. I was trying to think maybe I should do careers which I had in my mind, my price is a bit early. I tried to think whether I should be consultant, whether I should be a investment banker. In my Berkeley journey, I tried to do the actual role in consulting for about a summer. We actually went to Israel and worked there with the government on a project. And then very quickly realized consulting is not my cup of tea. I liked things implemented and seemed to be end of the line and actually see how it was and it's sick. And investing back in also the more I learned about it was not my cup of tea. So I realized I was right where I started which is I liked being a builder. But through that journey and my 20 years over the last 20 years, I've met a lot of builders. One of the things that I really enjoy is the passion that people who are solving the problem during the table and how they get obsessed with solving that problem in the world. So my angel investing for it was basically from that. I have a notebook that I still keep. I have ideas that one day I would want to solve. And I met other people who be notebooks. And some of them were actually I was jealous of because they were actually working on items on the notebook where my notebook is still on my desk. So that passion drove me to start working with some of them and understanding why they were focusing the next 10 years of their life on this problem. And from there on, other ways I can help them. And that passion really actually get me excited about what they're building and also get me cut me to learn a lot about those specific problems very quickly. So that's how it basically started working with a research company. Working on problems. And that still is the number one reason why I did this is just to meet people working on different problems, different industries and just very smart people trying to solve the problem differently. Oh, what a story and what an angle. I mean, I'm going to go slightly off script and then come back just by saying that I think you've been a very unique angle to it, right? I mean, having been a very technical background and having scale technical teams, you know, would love to hear a bit more like how do you think about assessing those founders and companies without technical angle in mind? It's interesting how things have changed actually. If you asked me even 10 years ago or eight years ago, would I ever take a team without a technical founder seriously that the company, I would say, they're smoking something. I think now actually given the tools and some of the things that exist now around no code, code stuff and that you can actually get some of the stuff up and running. If you have a particular other skill that you bring to the table and you can get it to an MVP where you can actually sexually subtraction. So, 10 years ago without technical founder, I would say good luck. I mean, you should go find technical founder. How I think you still, you're having a maybe age if you have a few founder. But you could get some traction. I'll give you an example. I mean, I've invested in a company which is the core thesis is around analyzing real estate contracts. You know, the founders are amazing because I think one of them has an economics degree and the other one is loyal and actually that probably applies more to the business than just bringing the tech in. So, I invested them early on because they were passionate about the idea. They were able to explain to me how broken the commercial underwriting system is for buying buildings and move out of the gothios there and how they could actually build a much better setup. But then a lot of this was driven off training of giving a product to battery wheels and these like lawyers and these companies who do this underwriting and learning from their work how to build a smarter system and this is before like charity and stuff. And they got quite a bit of traction before COVID hit. Of course, they impacted the business because commercial real estate was tied. And now they're on the other side where they're like, you know, using a lot more AI and again, two even analysis documents. But this is a classic example of not they're technical but then they own space but they're not like pure technical founders. But then they were able to hire actually one of the people that hired. I did their final run interview for that CTO hire. I just turned out to somebody that I interviewed before too. So there are places where I've seen now that even if you don't have a pure technical team from a I can buy the code perspective. You can take a challenge in the form. Harsh, it's like we set this up but we really didn't because we're also co-investors at C-CAM in orbital witness and I know Ed and Will super well. So then completely agree. They're just their founders who can articulate the problems so clearly. I also came from a legal background prior to C-CAM. So I remember when I met them I was like, this is a problem that needs to be solved and those guys seemed an ideal fit to do it and also agree with the technical talent they've built around. It's put the company to great spots so it's great that you've been able to guide them in that way as well.
[MUSIC] Kind of changing into, or like going even further into the investment pieces and strategy and how you think through your angel investing. One bit which I'd love to get you to kind of expand on is a little bit about where you are with your angel investing now. Obviously, when you maybe started making the first investments, it was earlier in your career, was it a certain point, almost like maybe even what the trigger was to think, what wanted you to go into that. And then also how far through you are in terms of like taking off those things in your, in the book you described, the ideas would look to let's spend a little bit of time on that one. Yeah, so actually just going back up to that. I think a lot of people start off this way in angel. At least most of the people I know, they start off by just helping a few mates. And helping other builders build stuff to get excited about the idea they're working on, they get obsessed along with them, they're doing as we can call them. And suddenly you're like, "Oh, you're raising money? Of course it's going to be great." So you give them some money and you get on with it, right? So I did that around 2012, 2013. To be noted, all of them have gone bust. They were horrible. They were horrible ideas, right? I'm not horrible ideas, but like in an, or an egg is a good execution, there's so much to build a company that just ideas. So I realized, you know, I do this retro every year and the end of the year and how the year went. And one of the things outside of popping up was like, "Oh, did these really interesting small checks? What happened to these companies and how they're fun to doing?" And basically my retro was like, I was doing more charity than really interesting. So I had to take a very, very objective approach to like remove myself from this bias. I said, "Okay, this is kind of weird because now I'm, and also it might impact my friendships." So what I should do is be more objective. So how could any more objective is by being blind a little bit. So I have no association with these folks. And I'm going to look at every deal that it comes through on the face value given a deck, given presentations. But then how do you get this deal? So I actually just found Angelist and I started joining some syndicates, pitched myself and do a few syndicates. So I gave them deals for that way. And you know, like I end up investing in a furniture company. It's called Barrow. I'm not on the cap table. I'm just through an STV in there. They don't see me see now. It's fine going slowly, but it's fine, but you know, they're doing fine for what I do to see. But I learned a lot about the furniture industry, right? Now every time I showed it and walking by low thought, I'm like, "Hmm, how is this just in the Barrow?" And like, you're trying to look at the product. What those deals taught me was actually very quickly helped me learn a lot about what a founder share, what are investors ask. And some SPV is a better, like they were actually coaching us in the earlier days through this process of, you know, like I didn't know that you should be asking for prerator. What a healthy prerator. You know, I mean, obviously as a small person, you cannot be as a big, big vehicle. You can. But what does it even mean? Why do you want that? What does it mean from a dilution perspective? So it actually taught me a lot by just dipping my feet a little bit into Angelics and getting me to use vehicles going. And then through that, I got some confidence on the thesis that I was running, which my thesis is not like I should do one industry, I should do one type of company. I just kind of go pretty broad and look at what's interesting that's happening. And then from there on, I went to, that helped me basically start doing direct things. So by that time, you know, I think I did my first big direct deal in 2018, when my son was just born. So in fact, I did sizzle take Carter. The founder knows this, but I took calls in the middle of the night because he was in the early morning, because he was in Estonia, I think. And he thought I was waiting up early for his calls to take the call with him, but I was up because my son was crying and I had to get the city in the middle of the night. Two sites, it was calls to you. But it was, that's my journey, basically. So failing with a few friends, who had great ideas, and I was too emotionally invested on to going completely opposite side where I started to be too objective. And then another platform in the middle ground where most of my deals are, there's some connection to the people usually, a people connection somehow. It's how I got the deal on my inbox, think my inbox. You know, super interesting to see that kind of evolution. And as you think through you mentioned there, I've seen about like indexing on the people, but are the sectors that you'll kind of lean into more because of your experience. And obviously having worked that E-bay and such senior roles and then now of see the CTO at wise. Or are there, is it kind of that you actually stay away from some of those sectors? Because you know, angel investors who have that deep domain expertise can kind of go almost one of both ways. Yeah. So I am pretty fraud. I do think that is a selection bias is generally in their deal flow, even what deals show up on your inbox. So it's not I was just looking through the list that I maintain of all companies I've invested in for this call. And I can see like there's definitely earlier days I had a much bigger bias. Even I think there was a bias in what was showing up to me was mobile payments companies. So I can see a team, this payments or something to do with my finances. There is a SMB subscription product, that I think. And then there's other things like real estate, I've got things around trucking in India enabling to improve the efficiency and tracking of trucks. It's a very big industry in India, but such an integrated technology and trucks, talking to still that we're using. So how do you improve efficiency for truck owners? It's a very kind of out there problem, and a different problem. So I think earlier on years there was a bias for payments and marketplaces. Now I think I've produced a list. Just jumping in with one more question, which is usually a conundrum we see as angel investors, right, which is capacity and time. Portfolio theory tells you diversify, the more institutionalized and you get to know about Paratha, you get to know also about the statistics of it. So how do you think about that trade-off between portfolio diversification versus having capacity to support those founders? Yeah, it's a tough one. I struggle with this a lot. So I get, I fall in love with ideas, I fall in love with people, that's what I want to invest in. And then very quickly I have to be conscious, can I spend time with them? And that bar has gone higher and higher because now as I've got more people, and more people in the list who have already invested in the company. So maybe my bar should have been higher than the audience. And I think you should have a higher bar in the early days because you just get kind of like very quickly caught up into like I want to be part of these amazing ideas, amazing problems that you've been solving. One trick that I have learned, I think I was a new Anthony world. So I've been able to luckily work with some more, how they can see from, big from early stage firms in Europe, in the US, where I've become part of the expert network too. So what they'll do is they'll kind of send me some deals, you know, to more from an intro from a perspective of, hey, we think hardshmabee helpful for you at this stage of the company, you should talk. And they know that I will look at all deals, not just payments, but that's helped me kind of have a little bit of a filter and allows me to spend my time more wisely versus just spending a lot of times with God's particular people. I'm sure I'm missing some folks that I would like to spend time with, but I just have to, you know, building wise is more than a full time job. So I'm still doing this on the side. So I have to kind of prioritize that. It's so fascinating, you know, your story, how I've seen some of the companies you've worked at and particularly now with this, with such a key leadership role at wise. It's almost like scale. You've seen such scale and the companies you've been part of and now wise is, you know, it's pushing through so much money on a monthly basis. When you look now at these super early stage opportunities, how do you assess whether those kind of founders and those companies can go on that journey? How do you see, because you've actually seen scale? It's so rare to have someone, even on this podcast, and we're really privileged to speak to some amazing angel investors, but to really see scale in a technology company like you have. And when you sit down with these founders, I'd love to see if there's any insights you can give to maybe me and Anthony or anyone listening about how you assess whether they can go on that journey. I think that's a tough one. I think generally I'm not assessing whether you will be able to scale the level where wise is reached up, hey, pound reached up, you've reached. It's kind of, when you look at early stage, you have to look at the personality and the person. Like, so I like to ask the question like, okay, why would you spend the next decade of your life building this and working on this problem? And that's really interesting how founders answer that, right? You know, some founders are, I think it's a good business problem. I think nobody's attacked this space. Okay, you can be very smart. I think generally that onset, the fire and the belly goes out quickly. I think people who had a personal journey on that with the problem, they usually tend to have a bigger fire in the belly to solve the problem, right? Okay, this is very cliche and very like high level. No, it's perfect. But I think it does come true and ring true so far. I also look at what have they done before. Like, how do we have Scott issue? It's like what I would say. And Scott issue comes by doing. So I'm not saying that I'm on
like amazing young founders coming out from college and building amazing companies. But if you look at a success rate, a lot of people who have been able to do sustained performance and sustained scaling, they've done something which has been previously hard to. And I think that helps again build that. So there's something inspiring and very because of the reason why you're chasing the problem or you've got some scale because you've done something hard before, right? But I think those things are the things you look for. Afterwards, scalers can be hired. It's not the hardest formality. If you are in the lucky position that you have a great business, people will be like bending your backwards to come help you build. Any of the problems is like how do you pick the right scalers to help you build, right? Let's go a bit more and talk a bit about your core learnings from angel investing. [MUSIC PLAYING] Got your learning more about the angels, right? [MUSIC PLAYING] So if you had to share three core learnings maybe you've already touched on some already, what would those be? Number one, early stage, it's all about the team. And the way I look at it, still there's the team have a trustler and a hacker. So usually I think two people teams are great because everybody knows like any relationship you'll have your good and bad days and things are hard. So you want somebody beside you building with you. So for a tech company, if it's a tech solution or anything you do with scaling and large numbers and is powered by tech, you need to have a hustler. As in somebody who can paint the vision, maybe sales, maybe marketing, something that they can really get out there and get the early customers will be passionate about being in front of people and selling. Even if it comes to business, how do you get this first? 10,000, 200,000 customers. And then the hacker is obviously needed to just build the product, right? So that's one thing I look at. But it's all about the team. And then you check the thing I check for is, do they have the ability to work through first principles? So there's a lot of topic ideas, especially back in the day in Europe, I think Europe's not my better, but back in the day, there's a lot of topic ideas. I'm Uber for blah. And actually I'm just Uber for you for Europe. And some of the companies have done well, but generally I think you have to work through first principles of why this problem in this market, why is this the right time and can they articulate that? And then the final bit on this one is, still the first one, by the way, is why will they spend the next decade of their lives? So that's the team. So the hustler and the hacker can detect on first principles and they will they spend the next 10 years building this. The second insight for me was be careful of your own bias. I think you got to work this. I was getting a lot of payments companies in the beginning. It's kind of funny. Founders, I think, need to be naive and bold. Sometimes the biggest problem solvers are not from their own industries. So they kind of naive to let go. We can do this differently. But as an angel, you're seeked out for expertise a lot of times. But you should also try to be a little naive. And I'll give you an example on this one. So I probably missed out the biggest return on an angel investment a few years ago, where I met this founder working on improving check payments and enabling businesses to get paid by checks and move them down line in the US. Amazing, fun, amazing story, amazing hustle. But I was so obsessed with ACH chargebacks. If you've ever worked with the US payment system, ACH chargebacks is a big problem. And my entire journey of the last 20 years of building eBay, PayPal, and Ys, I was like, what about ACH chargebacks? Have you talked about this? And I just wrote him up thinking he has not thought about this. This is going to be a car crash. It's 4 billion valuation today. I would have been in the early months. So that tells you, you should be thinking about the industry, but you have to be a little naive. Because you have to believe in the person going back to the first stage. For another, the team, think about first principles. And don't try to apply your all-year learnings on them. They go, then you're becoming the industry pair, right? And at the third one, I actually think this is a very bad business to be in. If you're just doing it for returns. I think Angel Inversus actually predicts or returns overall. Like you can get massive returns. But I think if you look at everybody who says they're Angel Inversus in the world, given the deal flow that you can get and how you get access to it. And there's so much competition. And now, we see firms also going like super early. I think it's actually-- if you just dare to maximize in terms, it's probably going to be an update. I think what you need to have is another reason why you should be in this business. For me, it's the first principles that I had, which is I love meeting people who are passionate about an idea, learn about the industry, why is this idea worth while solving. And along the way, if I can help them, that's great. And then if I make some returns, that's good. But I would elected my spec sheet. There's a clear chance that a lot of these will go to zero. In fact, some of them have started going to zero now, right? So I just had one company that they got acquired but it was basically a tie-on acquisition. And I got to return back after the whole deal, 42 cents on my entire investment, which came back to my account. So very often, up and up, would I invest in the fund where I get? Yes. But the outcomes are not as great all the time, because we only talk about success stories. So you have to be in it, I think, for more than just returns, because you're taking very early bets. And making some of them the bets I've taken will be fine. I cannot pay that entire portfolio out. But it's just-- you can't be in this, I think, for just choosing for returns. I think that's my piece. I should be doing it for something else too. Along with returns. Even beyond that, if you're there only for the returns, I'm taking it back to us, seed investors or angel investors in different microphones. There's so many ways to make scaled returns that are much more efficient. I think most seed investors are slightly rational in doing it about the passion of the craft first. Of course, if you're doing it professionally, hopefully at the top 1%, you'll do extremely well. That's the industry we're in. But definitely, can I identify with that? And I could actually very much identify with a second, because I'm increasingly doing more fintech, which is what I've done. And I always obsess about making sure I'm proven constantly wrong in a first-principles thinker. And doing it at a pretty seed, it's all about meeting the next great person that's going to prove me 100% wrong. On the first bit, the one thing that I've increasingly spending time on with either senior operators about to start a new business or founders about to do their next thing, especially on the former category. On the one hand, it's obvious the reason why you should have a co-founder for many reasons. On the other hand, sometimes it's quite hard. And also, brute forcing such a partnership can be tough, and a lot of the failure in the early days comes from founder fights. I mean, what are your views on that? You have a solo founder in front of you versus brute forcing such relationships, or is it not just the trade-off at all? Anything in life, you can't have an absolute role. So you will have exceptions. And yes, I have seen my fair share of founder fights like way too many. I still think that this is the composition that comes naturally because the company is very, very hard. So you want-- even on the founder fights, actually, when things come to the end or the end, there still is a lot of respect in that relationship because they've gone through some of the journey together. So even though you might have fallen out, there will be a mutual respect. And you see them investing in those companies over time because there's a lot of professions in there. But yeah, I agree. That is an amazing idea and an amazing founder, and I find this, or her belly, to go at it, then I would still fund, and I would work with them. But it's definitely a reason for me to look at going deeper as to this is a great idea. How come there's not another person in the world who we can convince to join you? Because if you can't, then how do you convince the next 100,000 people as customers to join you for the business of consumers? So I think that's a question that I always ask. Doesn't necessarily mean that I'm still as obvious that there will be two people. I should look to ask you a little bit about the learnings you might have had of being, so you're seeing your operator on both sides of the Atlantic. And whether you find now that you're investing, whether it's in European startups, whether any of that learning that you've seen through those companies which have gone on that hyper-group journey in the US, and now obviously being at an international company like Wise, which is Hfordon London, whether anything there, or the EC is in impacts or provides you with the kind of insights that helps with your angel investing. I've got about 50 investments across the ecosystem. This is just direct deals, some or even your list deals. And then this is besides my investments, our own L.P. in other deals, like in other venture funds and stuff, so that's separate. And if I look at my portfolio, yeah, you're right, a large portion of that is US in Europe. I would say the NATO last few years more in Europe, because I've been spending more time there. Of course, a lot of people I've invested in come to my network, some of them XYZels who've gone onto both companies. I know them, I know what they can build. So obviously that is a bias in our funding people, you know, a little bit. And then there's a few in Asia. Living in Europe has made me a better investor and a better global thinker. Because in the US, so I, you know, previous before I spend time with Verizon Europe.
all my time was in the barrier. And actually, it was of the, you know, believes that if you're going to build a company, you just have to move to sales system. Right? And so I believe in that mean. And now, obviously, I disband even it because it's built a company which is not based on it. I don't have one employee, it's not. And it's, you know, it's the nine billion dollar business now. So yeah, so I think it's made me a more well-rounded investment. And also, I'll give you an example. And so one of the founders that I've invested in is Martin Sock and Mikael Amir, the building Lightyear. So it's an investment app in Europe and the XYZ. So I work with Mikael and I work closely building some of the engineering of tech and wise and Martin was in the product side and we work very closely together. We're very good friends. But initially, when Martin pitched me the idea, I thought it was done. So the idea was, hey, we're going to help, we're going to build a Robin Hood clone basically in Europe. And I was like, why that's easy to build. Why would you spend your soul smart? You should stop doing this stuff. Like you should be doing something else. Like I was trying to put him out of it. And I also had my own belief, which is, so I was really earlier well-trained and betterment as an investor. So I believe in this diversified approach, setting up for getting a dollar cost averaging. And those portfolios over the last 10, 12 years have become decent size and I don't know anything. And they are very efficient portfolios. I was obviously, it happens. It's fine. It's on setting for getting. And my thing, Martin was, if you want people to create wealth, don't help them pick stocks. Just help them figure out how to save and put that money in the market. And that's it. And so I said no in the beginning. He said, I would love to maybe recall you and just have fun ideas of you. And I realized, so you're a patent problem, which I was not seeing because I had in my US bias because most of my business, in the US, given that pay taxes and anything in the US, which was, there is no way to access the US market in a cheap way. If you do try to buy Tesla stock in Europe today, the stock is in dollars. You have to buy, for example, buying in euros. You have to pay FX margin on the conversion to buy. And then when you sell, you have to get FX again. And brokerage fees are insane. Still, insane. Right. If you are able to access the market in the first place. And most of these products are run by big bags. They're very poor products. So then I was like, oh wow, the problem is not even like, forget about getting to a place where you're doing index investing. It's further up the chain. So that understanding and that I saw that then when I was in Europe and understood the problems that people were having. And the access issue is a big problem. So that changed my mind. And I think if I was sitting only in the US with my US lens, this would have been something I would just like, yeah, sounds like an idiotic idea. And the other bit was pretty interesting, which tells you how old I am. I was like, for me, financially stable. I'm longer done thinking. And Martin's point was, you need to get people excited about what they're doing. Like getting to fall in love with these companies, why would we simply spend the time thinking about returns that they don't even know? Index fund is not exciting. You don't talk about index funds at a pub. I'm like, I do. Because you're different. So I think that was your proposition. Right. I was like, if you want to, you know, the mind of young people, you need to get them excited about. But that actually it harks back to my first investment. My first investment was Apple when I was in college. And I saw everybody's Christmas list, Christmas list, shopping list, I bought on it. And this was going to kick me like, I was there, right. And I was like, every kid wants it. The kids who cannot get it, they are deemed to be not cool. We should buy this company. So that was a thesis, right. So it was not wrong. So anyways, I think being across, being in Europe, being a bit outside the US bubble has also helped me understand the geographical nuances of why would you not have a Robin Hood? This is a problem in Eastern Europe, for example. And what is challenges of building that? I love that. That international lens, you know, is investors who who sit in Europe, competing often with US investors. I think that's music to definitely to mine on Anthony's years. Is there the end of an episode? We love to end episodes with a bit of a quick fire round. So quick answers, 30 to 60 seconds each. How does that sound? I'm very nervous. Don't be nervous. Don't be nervous. Okay, right. What is the most counterintuitive thing you've learned since you started to angel in this? Being an expert is actually sometimes a liability. Perfect. Stowe's the point. The next one, I think we've actually touched upon a little bit, but I'll ask anyway, maybe we can do in a 30, 60 seconds version. But what would be your top tips to angels wanting to do more international investments? Every market is a bit different. So try to understand from the founders why they are building a product which potentially exists in the other market. But what is the local insight? I think most products, even at vies, we build with a global lens, but there's a percentage of it that is cool and that local nuance is what drives the high alpha if you get it right. So the last one, what advice would you give your 10 year younger self if you only had 30 seconds? Maybe fall in love less once you do go all in. The, I mean your experience is inspiring to so many new founders and ecosystem as a whole. It's like to be happy harsh. Thank you for joining the show and for sharing your insights. Thanks so much for having me guys. Thank you, Harsh. Sitry? I'm an angel. Because God knows that everyone needs a little coaching now. I saw an angel. He said it's me an angel. The small office. Being it to get that the top of me, John. Being sliced by an angel.
Podcast Summary
Key Points:
Harsh began angel investing after a career building products at eBay, PayPal, and later as CTO at Wise, with a focus on scaling and performance engineering.
His early angel investments were driven by emotional connections to friends' ideas, but most failed, leading him to adopt a more objective approach through platforms like AngelList.
He now evaluates founders based on their personal passion for the problem, their ability to articulate it clearly, and their track record of overcoming challenges, rather than just technical backgrounds.
Harsh maintains a broad investment thesis across sectors, though his deal flow is naturally biased by his experience in payments and marketplaces.
He struggles with balancing portfolio diversification and time to support founders, using expert networks from venture firms to filter opportunities.
Summary:
Harsh, a builder with over 20 years of experience at eBay, PayPal, and as CTO at Wise, shares his journey into angel investing. He started by helping friends with their startups, but these early investments failed due to emotional bias and poor execution. To become more objective, he used AngelList to join syndicates, learning about founder evaluation, deal terms, and industry dynamics.
This experience helped him develop a balanced approach where he invests in founders he connects with personally, but with a critical eye on their passion and ability to solve a problem over a decade. Harsh assesses founders by asking why they dedicate their lives to a problem, preferring those with a personal stake and a history of overcoming challenges. He invests broadly across sectors, though his background naturally biases him toward payments and marketplaces.
Managing time is a key challenge; he uses expert networks from venture firms to filter deals, allowing him to support founders effectively while focusing on his full-time role at Wise. Harsh emphasizes that successful scaling often comes from founders with prior hard-won experience, not just great ideas.
FAQs
Harsh was inspired by meeting founders who were solving problems from his own notebook of ideas, which sparked a passion to help them and learn about diverse industries.
He now considers non-technical founders viable if they have passion, domain expertise, and can build an MVP using no-code tools, often hiring technical talent later, as seen in his investment in a real estate contract analysis company.
He started by investing in friends' companies, but those failed, leading him to adopt a more objective approach through platforms like AngelList to avoid emotional bias.
He struggles with this trade-off, raising his bar for time commitment, and uses expert networks from early-stage firms to filter deals and focus on the most impactful opportunities.
He looks for a deep personal connection to the problem and previous experience overcoming hard challenges, as these traits indicate sustained performance and scaling ability.
He invests broadly across sectors, though early on there was a bias toward payments and marketplaces; his portfolio now includes real estate, trucking in India, and SMB subscription products.
Chat with AI
Loading...
Pro features
Go deeper with this episode
Unlock creator-grade tools that turn any transcript into show notes and subtitle files.