Jeffery:
Igor. Welcome. We like to just keep going right at it. So I have a good little conversation going and then we jump right into it. So I’m very excited to have you here today. I’ve uh I think the reason that I’m really more excited and I love to say this, I’m excited about anybody that I get to have a conversation within the Angel-VC world. But what I really like about your background is that you come from a technical background and that’s very rare that I get to interview someone that has a technical background which is very similar to myself. So it’s kind of dear to my heart that I get to pick brain with a tech geek and that is something that’s amazing. So for me we’re gonna jump right into that part of it, but maybe the best way to start is um if you can give us a little bit on your background, kind of where you’ve come through the exits through everything you’ve done in Boston, in the, in the networks, they’re kind of where you are today and we’re going and then we’ll kind of jump into the conversation from there. And then one thing about you that nobody will know.

Igor:
That nobody will know. I’m an open book, so I don’t know if I can think of,

Jeffery:
So you can find something in there, Igor, come on, I know it

Igor
Look give me, give me a minute, I’ll think about it. But let me give you my background. So uh yeah, like you said uh tech guy, so I uh I wrote my first line of code when I was nine, I made my first money from software when I was 12.

Uh and there’s just been uh I guess uphill downhill. I don’t know what you would call it, but it went from there, so I’ve had a startup after startup, you know, my, I’m originally from Ukraine, I lived in Moscow, my dad was an entrepreneur, so it’s kind of like in my blood and uh, just started about their startup, uh, of all sorts of kinds, um, mostly failures, uh, some gloriously so. Some for all sorts of reasons, sometimes, uh, sometimes co-founder, sometimes like the typical ran out of money thing, sometimes, uh, one time a legal issue where I was told, don’t you dare launch this. Uh, and uh, eventually, you know, I, I lived in Boston other than san Francisco, came back to Boston, found a startup and uh, finally had like a big, big exit, uh, not a big, big exit, big enough exit.

And that was a couple of years ago and basically kind of pivoted my life since then, because they gave me a little bit flexibility to do some uh, well, basically anything I wanted. And what I wanted to do was help startups, uh, in all sorts of different ways. So I did some angel investing. I do consulting. I’m, uh, well, my title is mentoring residents, although there is no longer residence because of Covid, but I’m a mentor and residents at, at One Valley, which is an accelerator program, used to be called GSP Labs.

And uh, just, you know, I’m doing some angel investing on my own. I do it with a group here in Boston called Beacon Angels. Just having fun man.

Jeffery:
No, I love that. Very good, very, uh, very in sync with the world of entrepreneurship and angel investing. So I love the background and how that all ties together. So maybe well before that, I’m still gonna let you keep thinking about that one thing that you’re going to share with us and we can hold it off because we’ve got a personal segment, we’ll talk about near the end of our chat,

Igor:
But thinking between two or three things come back to me later.

Jeffery:
All right, we’ll talk about that at the end then. So what I love to do is kind of really dive more into that background experience. So, I love the fact that when you were nine, you’re writing code, when you were 12, you were diving right into it and building a little empire.

How much of that background has really defined how you’re investing. And the reason why I like to kind of play of this angle is because when you start to explore your past and how much it shapes your future is that when you start to dive into these startups, you’re coming at it from a totally different angle, you’re not coming at it from finance, you’re not coming at it from marketing, you’re really coming in from the technical standpoint and that background you’ve built over the last however many years. So how do you define how much that’s helped you today and what do you look for when you’re looking at founders? Because of your background in tech?

Igor:
It’s a good question. It’s very much a double edged sword, right? Because on one hand, you know, you invest in what, you know, what I know is that, uh, so I’m very adept at looking at a company qualifying technology, doing almost a mental technique, diligence on them very rapidly and assessing whether it has legs or not. Uh, On the other hand, write it blinds me a little bit to the, to the financial side. Um, even though I could assess that as well.

Right. I’ve had, you know, so far all of my investments knock on, you know, fake IKEA would, but all of my investments are live, I’ve had a couple that are kind of stagnating, but they’re all kind of lives so far. But for sure. One of the very first angel investments I made, uh, was in a, in a Boston company, like two-sided marketplace sort of play. I looked at the tech look great. I looked at the idea of like, this is awesome. And I didn’t look at the financial side at all.

I didn’t look at, you know, customer acquisition costs. I didn’t look at run rate. I didn’t look at anything. I was like, here you go. Here’s some money run with it. I learned my lesson. I learned my lesson for sure. Um, on the other hand, you know, I, um, I do have for the most part personally I invest in technology, I can understand, assess and believe in its longevity. However, that’s exactly why I joined an angel group, Right? Because basically, uh, I said, look, there’s, there’s opportunities out there that I can’t assess.

Uh, it would be really great to work with people that can help me, right? And so on the angel groups side, I do have, uh, companies in my, you know, investment portfolio that are life science companies. There’s one company that’s doing, you know, a post op eye gel type of thing, uh, that I know zero about.

I went to a board meeting once and I, I think I left smarter. I only understood half the words. You know, it’s two doctors, kind of ophthalmologists running it. Um, and I have some other kind of things that I don’t quite understand and I’m kind of trusting my, my peers to leave me in the right direction. But uh, you know, fundamentally angel investing is hobby, right? And that’s what, you know, I talked to a lot of kind of beginner, angel investors that were me maybe five years ago. Like, hey, I came into some money, I had an exit, What do I do with it? And the first thing I tell them is, you can’t look at this an investment, I know it’s called angel investment, but it’s non-investment, It’s an expensive hobby, right? Like you like skiing 10x. That, that’s angel investment, right? Maybe you’ll hit something. But really what you’re doing is, you’re, you’re giving back to the community and you’re letting someone have a chance. So the same way, how all of my angel investments are live, uh, none of them have been, you know, a big exit for me.

One guy actually returning the convertible note with interest and said, look I uh my company stagnated, I sold it for assets. So here’s your 20 K. Back plus 5% interest. And I said look you’re ahead of the curve, you know,

Jeffery:
winner, winner chicken dinner.

Igor:
Exactly, exactly. When I invested. I mean I I shouldn’t say when I invest in something, I kind of write it off, but like mentally I prepare myself to do that.

So when it comes back to me with 5%, I mean, yeah, I bought abolish campaign for sure. Mhm.

Jeffery:
Well and you brought, you touched on a lot of great points there and the one is that you almost in this space when you’re not doing it full time, it really is, it’s a hobby of trying to pick the winners and hopefully they’re the ones that drive forward. But you really are, you’re almost, you’ve got a set of money that you put aside that says here is really high risk dollars and I’m going to throw this money into this many companies per year and I hope that this is going to bring me some gains. But really I’m okay if it doesn’t, I’m going to keep working with the community and building out and giving back and helping people. But I really do write that dollars off and 100% that that’s a strong early stage angel VC mentality because if you did and you were stressing out, then you would probably work in 24 hours a day trying to work inside of every investment you’re with to save and make every company work and grow right.

Igor:
Exactly. Yeah. I mean there’s, there’s metrics out there and I’ve read some stuff about how many investments one must make before. Statistically you have a positive outcome, rather QVC like outcome. And it’s something only the super angels get too right. If I’m investing in a handful of companies a year, I have 10, 15, 20 investments. It’s a crapshoot, right.

If I’m a super angel, you know, if I’m investing in 100 things, then I can aim for like a VC like 12% return or something like that. But at my, at my, you know, paltry level, it’s a gamble.

Jeffery:
Well, it’s still great that you’re doing it because again, it’s a tough space and there’s not a lot of people that like to get into that gambling side and um, you know, hats off to you. I think it’s amazing that you’re doing it and the whole mentality of going in and giving back and, and being able to be part of that I think is huge. So we commend you for it and we hope more people will jump into the space, just like you do. So that’s amazing because it does help these companies get off the ground.

So there’s one thing that really kind of stands out in all of these things that you’ve done and what you said, and that was qualifying the tech. So a lot of founders and I’m going to just put a number out and say that 30% of maybe 40% of companies that are created in the tax base are created by non-technical founders.

I would say it’s a bit higher that there’s more technical founders that created, but they usually find somebody on the business side to run, uh, and manage it. And sometimes it’s just them operating and running it. But if it’s just pure businesses in the technical space that have started, it’s probably 30 – 40% where they have to hire someone to do the tech, so they’re trusting somebody else to do this.

And I’m sure you’ve come across this when you’re diving into these companies again, because you’re not talking with a technical co founder or the founder, how do you validate this code? And are they open minded to you coming in and taking a look at it? Are they? I think it’s amazing or they afraid that you’re going to beat them up and that this isn’t the right thing and they built the wrong thing. So how do you kind of coach those companies through getting their product to market in a technical or nontechnical biased way, so that when you do come in, uh there’s going to be a good review for companies and the audience listening.

Igor:
That’s a deep question. Uh So, look, there is um, I’m gonna I’m gonna answer in two different parts because there’s Igor the person and then there is my company which I created partially to address exactly the problem that you’re kind of implying, right? There’s a lot of founders out there that end up with a terrible experience, working with, you know, co-founders, freelancers, dev shops, not, not through any fault of their own and often not through any fault of the developers that they’re working with, right? It’s just, uh, you know, there’s a long road from what’s in someone’s head and what a developer actually ends up with.

Right? And so for the most part, I would say that the founders, regardless of whether their technical or not, are very open and in fact appreciative of someone like me looking at the code. Occasionally, when you end up dealing with who I would call the scammy Web shops, which is not the majority, but some right that the kind of folks that hold coach hostage before until you pay the kind of folks that you know, have vague SOWs. And then argue about what wasn’t wasn’t in them, those kind of folks very much don’t like me.

And then, um and not because you have to, you have to remember the founder wants an investment, right? So they want me to come in, have a good experience and give them some money. These guys don’t care about whether I invest in the company, right? They want to get paid for the work that they’ve done and they don’t want to show anybody the quality of that work. So I have had some resistance, but it’s almost never from the founders. Um and in fact, you know, Igor the person helps a lot of founders with kind of like, you know, let me take a look at what you’re doing there. I had a call just the other day with a, with a technical founder, but this was like the spurs go around and, and uh, he called me in the middle of the night.

He was like, anywhere. I know like it’s the middle of the night work on this react code. I just can’t get it to work. Like, can you just look at them like that’s fine. Like this hop on a google meet and we kind of debunked it together, so I’m happy to do that. Um, but uh, yeah, it’s rarely from the founders. In fact, that’s Igor the person fast CTO my company about a third of our clients are technical founders. That kind of, they know that, hey, I’m a competent developer. I’ve never done something of this scale. Let me work with someone that can help me get it to that level and prepare me for the due diligence that’s going to happen in the future, right? Because they, they’ve never been through the diligence. They don’t know what’s gonna, what, what the other guys are going to ask for the VCS are the angels or whatever, although they asked different things.

And so we go in there and we say, okay, look, you can’t story of passwords in the database, you know, you can’t do this, you can’t do that and we help them out.

Jeffery:
So in that kind of deep dive and when you’re qualifying it, this is for Igor to be coming in as an investor into this company. Have you stopped and decided not to invest in a company because you found that even though this looks like a great product, great company when you dove in, you are questioning the style of the code or the antics or what they’ve done, what they missed, what they didn’t do, right.

And just kind of looked at and we’re like, you know what, based on this, you guys are way too early for me, even though you’re raising this much and you’re doing this and your business is doing okay. But man, this platform is gonna fall apart if you hit 1000 users and I don’t want to be part of that ship. So have you ever had to kind of really dig into that and say that?

Igor:
Yes, dig in is the wrong word because it’s usually pretty obvious really quickly. But there’s definitely been, it’s not, it hasn’t been because you’re too early for me and it’s rarely because, hey, this won’t scale because, you know, I build things to scale. Like either the person builds things to scale, but you are the entrepreneur kind of believe that scaling is tomorrow’s problems, right? Like let’s get it out, let’s get revenue, then we’ll deal with scale. So what stops me dead in my tracks is code that the founder expects to be the foundation. Like they’re asking for money, they’re raising whatever to build on top of, and this thing is not a foundation, right? So a quote, I always tell every founder and everyone was actually, really, everybody is shortcuts are okay to take as long as, you know, you’re taking them, right.

And so if, you know you’re taking them, then you can plan for the future where you’re like, OK, I made the shortcut today, here’s my plan to immediate it later. What happens often is, especially with non-technical entrepreneurs, as they, they send, you know, they offshore their development or whatever, which is nothing wrong with offshore, and they basically send it out and those folks make a lot of shortcuts that the founder doesn’t know about.

The founder gets something thinks, okay, well, I’m raising $100,000 to take this from this scale to this scale, and I’m looking at you like, this is not the thing you take right? Like, you could turn a Nissan into a Ferrari with a lot of work, but you can’t turn a scooter into a Ferrari, you know, like, no matter how, how hard you work, so that’s kind of, that’s what stops me, and if they come into it with, like, the clarity that that’s the case, that’s a different story for sure.

Jeffery:
So there’s a lot of understanding there that if they have that and they can plan it, then you’re willing to kind of work with them on that investment and how they’re going to move forward. So I think that makes sense because as a startup, you have, you know, you don’t have all the money in the world. You have the means to drive out something well, but you can’t build the Ferrari right away. You’ve got to build the moped or you got to build the uh, tourismo and then you’ll work your way up right?

Igor:
Fundamentally. What comes down to is I want a founder that has clarity as to how they’re spending the investment. So if you, you know, Most decks, I look at one of the slides is like I’m asking for $500,000 and here’s how I’m gonna break it down if that looks right to me, that’s a big checkmark, right? Like I’d rather not see that slide than see that slide and it’s being blatantly wrong. So, so where that breaks down for me is if you’ve got a founder that says, okay, you know, I have this MVP, this is going to hold me over for a few months or whatever and then I’m gonna, you know, take 50K and build up the bill on top of it.

And I’m looking at this code and I’m like, it’s gonna cost you 200 K just to rewrite it, which is, it’s rarely that high. But you know, sometimes the whole deal falls apart for me because then this founder clearly has no idea what they’re holding,

Jeffery:
yep. Okay. No, and that makes a lot of sense how much of this knowledge that you gain as being a techie, how much of this has given you the forward-thinking of, I want to get into this space because this is going to be a new tech stack, where this is going to be a new way that people are going to be building X and Y.

So are you attracted to those types of things? And start ups as well? That they’re cutting edge, leading bleeding edge in the way developments being done or that’s really not part of it enough. That doesn’t really make or tweak your investment opportunities. You’re going after more of the people running the business and the opportunity than you are on the newest, craziest tech that’s coming to market.

Igor:
Uh, usually, usually I want tried and true. I don’t want a technical co-founder that’s using their startup as an excuse to like try out a new language right all the time. Like the hot new thing is Golang right and about once a month I need some founder that says, hey, you know, I, here’s my new app, it’s in golang, is this your first golang project? Yes. You know, of course, because everybody’s schooling project with the first grueling process.

And so I’m certainly not going to invest in the start up that somebody’s guinea pig, Right? That’s not to say I want them to be using like four trend, Right? But there’s there’s mature technologies with a good community that has, you know, a lot of developers when you need to hire at a good rate because, you know, you’re using my money to hire them. Right? So, you know, and you you you probably know some technologies, even though tech stacks are commodity, some tech stacks are better for certain things and some text tax organically cost more to develop it. Right? Like for some reason, I don’t know why ruby developers are more expensive than node developers.

Jeffery:
Right. That was my next question. Yeah. I don’t know, ruby developers are the hardest people to find. Yeah. They don’t want to do the code and if they do, they’re super expensive. And I always ask why did you build this in ruby? Like, well, my friend builds in this and your, like, your one friend, did you ever look about maybe if you had two friends in developing ruby, because we can’t find two people that consistently echoed in this if I’m not hitting 14 countries to find them.

Um, sure the code’s good for a really small little aspects anymore. Well, why don’t you go to a more common language? And they’re like, well, we looked at java like another one. Why do you go after these languages that your people cost hundreds of thousands dollars to work in and you’re not building NASA, you don’t need Java go and do something else. So I’m not sure where this, it’s that one technical person that maybe has been coding in Java for a decades or 20 decades or two years, whatever.

But they all seem to go to the what they know, and then they just follow it, whatever that friend is shared, but it can kind of impede the growth because like you said, cost is a big one. And if you can find the developers and they’re going off not as common platforms, you’re gonna be spending a lot of money.

Igor:
Uh, and even more common. An extreme example of this is when founders engaged with dev shops, right?

Because what a lot of founders don’t understand. And I try to tell everybody if you take your power point that like every founder was like, here’s what I want to build, you show at the three dev shops and one desktop says building in java Once this building ph d wants us building a node. It’s not because they’re saying that because that’s the best thing for you and it’s not even because they’re saying that because that’s what they specialize in. They’re saying that because the people on the bench, they have right now, that’s what they specialize in, right? You should never follow that route. You should pick what you want to build, decide how you’re going to build it and hire to that. It like flips the whole model on inside a little bit.

Jeffery:
Yeah, I agree. And that’s that’s some great advice. And I also think when you’re looking at that outsource step shop or your even in sourcing it and you’ve decided on the type of platform, just ensure that you can resource it properly that your area or where you’re going to be collaborating can find those types of resources to fill that bucket.

That’s the last thing you want to do is go to somebody that’s working three jobs trying to code for you, uh, and you’re gonna take even longer to get that production done.

Igor:
Exactly.

Jeffery:
So now that you’ve kind of utilize a lot of this back end that you’ve built up over time and this understanding of of the deep tech side, how much innovation do you bring to these startups when you make investments? Are you leading them with that tech uh, desires and pushes and kind of saying, hey guys i’m using a tool, have you ever thought of this? You bring this in or do you spend more of your time working on the business side trying to help them with lead generation, getting them in front of more investors? Like what kind of role do you play when you’re working with them? When you’re coming in as a technical, uh, investor?

Igor:
So, you know, the goal is to always be, as Mark Cuban says smart money, right? But I also realized that I’m not the smartest and there’s not every investment I make, that I’m the smart money right? To use the example of the eye gel. I don’t know, right? So they have my money for sure. And they have my full, you know, moral support behind them.

But like, don’t call me with a question, right? Again, there is no region and there’s no help I can give you. Uh, but that’s, you know, through a, through an angel group, Right? Uh, when it’s a personal investment, then 100%. Uh, you know, I I become an adviser. Uh, in fact, that’s, uh, for my personal investments, that’s, that’s part of the part of the rules that, uh, I’m on your advisory board. You know, you have an open line of communication with me. I want you to use me for what I’m good at. Uh, we scientifically a fast agreement like the founder institute, find a adviser standard template thing.

Um, and so yeah, I’m completely accessible to them because I want them to succeed Igor the company, uh, fasting too Igor the person that secure the company does exactly the same thing. Just times 100 things. Right? And so, uh, everybody we work with that. They have connections with angel investors and VCs and private equity and whatever else, uh, family offices. And we did basically, we, we, we really only work with companies we believe in because we’re not a dev shop. So it’s a little bit different, right? So you need to prove to us that you have legs. And they were like, okay, we’ll help you succeed, right?

Um and uh I mean it’s been great. Uh it’s different from investing a little bit, right? But uh, you know, we try to help.

Jeffery:
I love it. There was one thing that as myself as a technical uh coder engineer back in the day and now obviously operate and run a software company, um and we stick to what we’re good at. We don’t try to veer off into any other directions. Maybe in the past we did because we were exploratory and we wanted to learn more, but we know we’re good at, we stick to what we’re good at. So, but what I found was that when we work with developers that we work with technical people, and even throughout my career working with technical people, uh I found this and maybe I’m just biased because you spend so much time in the area, but I find that technical founders understand the mechanisms of the business from a whole different angle, they see things differently. So they have a whole different opinion of how the business should operate and function and run. And I think non technical people don’t look at it from that way. Maybe they just look at it from the top down, whereas technical people look at it from the bottom up.

So they’re seeing all the moving parts operating and moving. So their understanding what marketing is doing with sale, everybody else is doing because they’re from the bottom looking up versus down and try to figure it out. So do you find it with the business that you’ve constructed and built? Because you just mentioned that you guys are looking at companies that you feel you can fit into and work with?

So are you guys looking from the top bottom up and you guys are coming in with such a different view of a company and its way more valuable to that start up because of how you’re envisioning and seeing the product expand, how the business operates. Um, and you find that that is a real big asset to not just to you and your business, but to technical investors, that they really should find one that comes into your company, you should bring a technical investor advisor, um, into your investment, have them understand your business because they’re gonna see it a lot different than you do from a business point of view downwards?

Igor:
Yeah, I mean, it’s case by case. I would love for what you just said to be the norm, but it really is case by case. And you know, we work with a lot of technical founders that really kind of follow them all that you’re talking about, but we work with just as many technical founders that don’t understand the business side at all.

Right. Yeah. Nor do they care to understand it. Right. We work with a lot of folks for better, for worse, that kind of, not a separation of like, of roles per se, but, but kind of, uh, this is my expertise is your expertise. Of course, we’re working together, of course there’s an open channel communication, but like I’ll do my thing, you do your thing. I don’t think that’s the best approach for sure. But there are a lot of folks like that.

Jeffery:
I found that a lot of investors that I work with that are technical background. I just love how they pick a business apart. It’s just that they see it totally different than a business person and that’s why I kind of see it as being a bottom up view and then the business people just don’t understand the text, so they don’t see the business in the same direction.

So I find that they almost seem less knowledgeable about their own business and I don’t know if that’s right or wrong, but it just seems that there’s a different view in right.

Igor:
The good technical co founders extrapolate better right to like really put it simply because when they hear a business requirement, they kind of in their head, it’s like, okay, it could be this or this or this or this down the road here spades one, your space through here.

Space three. I know you’re saying just this, but really it’s all of these things and they go back and they put in the right architecture, the good ones, not everybody is the good one, but that’s where we come in and we kind of mitigated and help out

Jeffery:
I like that extrapolation. It’s kind of like, uh, they’re taking the problem. The problem has been zipped together with everything into this one folder and instead of having to unzip it so that everybody can understand it, the CTO or co founder CTO is already in that zip file, figuring out all the buckets and how it’s going to affect the business in the long run, which will then allow them to extrapolate the good, the bad and the ugly so that the rest of the team’s founders, marketers operations people can better understand what will change to the tech, which will change to how they all operate in their silos and how that’s going to affect or benefit them in the long term.

Igor:
Yeah. And then, you know, to what you said a couple of minutes ago, for sure. Technical founders get a much bigger picture, right? Because when you’re talking about all these different arms marketing advertising, all that, guess who’s integrating all of that in the main application, right?

So you might not know the details of, you know, how to set up a facebook campaign, but you know how the data flows in and how, you know, it goes into the CRM and everything else. So I will say just as kind of to shoot myself in the foot a little bit, there are some statistics. I don’t have it in front of me, but I saw a couple of months ago that I think I said something like 70% of recent unicorns. are co-founders that met in business school to that the implication of the course, that they’re not technical co-founders, right? But not always, sometimes, usually. Right. And so it’s certainly not a requirement for a company to have a technical co-founder.

Does it help only if they’re good? Right? Just like any co founder?

Jeffery:
Yeah, it’s a caveat every time. Only if they’re good, they’re good, it’ll work really well.

Igor:
But that’s why it’s hard to find co founder, like finding a co founder is, uh, is one of the hardest parts, and I, by the way, on the investment side, I dont invest because of the team, just as often as I don’t invest because of the text, right?

Like, uh, the team that independently is strong and together is stronger. That’s a team you want,

Jeffery:
yep, I agree with that. So we’re going to kind of jump a little bit, even though I’m trying to figure out, I want to ask a question like when you laid some code down at nine years old, I was gonna I was gonna avoid this, but I got to ask, so when you’re coding at nine, was it self taught, was it class just said, hey everybody gonna start coding and you were just like done, it was easy,

Igor:
now I’m gonna get you to that, I’ll tell you, I can give you the story. So uh in Russia, so I was born, I was born in Kiev, I moved to Moscow, I grew up in Moscow and in Moscow my father ran the store that basically bought computers in America and resold them in Russia.

So I had access to computers still in Communist Russia before most Americans had access to computers. Right? And so you know, I was playing, I was playing Texas and volleyball in like the late 80s and things like that. Right? Volleyball is I don’t know if anybody of your listeners remember just like a DOS game where these two bobbleheads bounce a volleyball. Anyway, it’s a really awesome game. It’s like DOS. But anyway when I was nine, my my father who was like, you know, you will be a software developer. You know, he bought me, if you remember back in the nineties, these were very popular like learn whatever in 21 days.

Remember those games, those books? So he bought me this book and it was called learned C++ Game development in 21 days. And it was a book this thing. Right?

Jeffery:
I think I had that book. Yeah.

Igor:
And so A C++is one of the most convoluted languages you can learn. Game development is one of the hardest areas to be in. Good luck 21 days. And it’s like nine year old. So that, you know, turned me off to like computers basically. I started that I’m like, okay, so pointers. Huh? And I wrote some code. I did some stuff. I actually did make, I think it was a mind sleep, not mine sweeper. What was it called? Uh Yeah, mine sweeper like game. Uh, that uh, it wasn’t exactly minesweeper. I’m trying to remember what exactly what it was

Jeffery:
Like the one where you had the squares and the boxes and the (inaudbile)

Igor:
Yeah, but uh, anyway,

Jeffery:
another one that was pretty — Tetris, pong. Those are all like, yeah…

Igor:
But nothing with movement, right? Tetris has a lot of movement. Pong has movement and tracking, collision tracking. I mean, it’s a whole thing, Right? This was simpler. Nine years old. Give me a break. All right. So, so basically that’s what I made some little game and I was just like, no, I’m done. Then we moved to the States and a couple of years ago, a couple of years later, you know, the internet was kind of becoming a thing, right?

And so when I was, when I was 12, I was, you know, I kind of said, okay, like let’s take a look at what this html thing is, Right? This was like HTML one Netscape Navigator Gold days. Right. And so I started making some simple websites. And then, you know, it turns out that most companies back then didn’t have a website. So, and everybody had one year of experience, including 12 year olds. So I was on, I was on a level playing field as like everybody else. So I actually did, I ended up making some websites for some companies in Connecticut where I lived and you know, made some money. My first check was for $120 And they paid me $10 per web page on their website and they had 12 pages.

Jeffery:
Nice.

Igor:
Yeah. So the 12 year old, I got $120 check you want from

Jeffery:
Did you charge taxes on that?

Igor:
That might have been uh, I think that’s under the table. It was under the don’t, don’t tell anyone

Jeffery:
Child labor going here, what’s going on with the.

Igor:
Exactly.

Jeffery:
That’s an awesome story. Uh So now we’re gonna fast forward all the way through to your investment period again. But I had to ask that question.

You know, it seemed exciting and it was. So with your, with all of the experience you’ve had now in investing in the companies, you’ve worked with, all the companies you’ve looked at deep dive in from the technical business side and the learnings you have, is there one company that kind of stood out to you that really blew your mind away? That you know one of those real entrepreneurial ship, entrepreneurship stories where it was like this is amazing, I couldn’t believe where they came from and how they got to hear uh almost fell off a cliff and now they’re rocking it or just something that really makes it kind of feel what it’s like to be an entrepreneur.

Igor:
Uh huh,

Jeffery:
a real positive crushing its story. You’re the gate behind, you know?

Igor:
Listen, I uh there’s a lot of positive, very uh kind of optimistic and influential and just like great startups that I’ve I’ve come across and worked with, I don’t know if anything comes to mind with that big of a dip, right? Because you’re looking for like a comeback story. Uh, listen, every company I’ve ever been part of at one point or another, we were broke right, regardless of whether we raise money or bootstrapped or whatever.

You know, we went to zero sometimes below zero. And so in a couple of times we came back out of it. So I guess, you know, you never know what’s gonna happen. Um, I should say like, because I do a lot of, I do, I worked with a lot of accelerators. I talked to a lot of first-time founders, you know, it’s just like sports, right? For every Michael Jordan, there’s a million kids that aren’t that right? And so for every really inspiring story that doesn’t mean you should always throw good money after that, right? Like there are a lot of bad ideas, wrong timed ideas, all sorts of stuff. So you can’t just always hope for a turnaround, but it does happen occasionally, right?

And and and then it’s, you know, it’s really awesome.

Jeffery:
I love it. I love it. And you’re right. And it’s a good analogy that, you know, there’s there’s a lot of Michael Jordan r sorry, there’s only a couple of Michael Jordan’s in the league, but there’s always a lot of everybody else and they all bring a good value, but you don’t know how long they’re gonna last in the league. Um, and you gotta, you want to bet on the big winner, but sometimes you’re gonna bet on everybody else and you’re hoping that they’re gonna get taken out too. But, you know, you can’t, if, you know, someone breaks a leg or snaps and ankle, or just doesn’t make it the next year, it’s part of the mix and that’s part of the investment. It’s part of the excitement.

Igor:
And by the way, you don’t need to be a Michael Jordan, right? Like a lot of folks listening to this, uh, your company is not investable, but that doesn’t mean it’s a bad company, right?

Everybody always talks about lifestyle companies as if it’s a bad thing. You know, like if you’ve got a million dollars a year and passive income coming in from your lifestyle company, you’re fine, right? Like you don’t need to be a unicorn like you’re, you’re fine. Uh, there’s plenty of companies that, that I work with and plenty of founders that are kind of whether they believe it or not, whether they wanted originally or not are in like a good spot in their company and like, no, I’m not gonna investment because I’m never going to see a return.

That doesn’t mean that you’re not gonna make a good life out of them.

Jeffery:
Exactly. And there’s nothing wrong with making money and getting paid and being sustainable and growing and hiring people and having a great lifestyle and being able to take home a couple 100,000 or a couple 100 million every year without having to be stressed on the investment side.

Igor:
But even 100,000, Right? In most places, not San Francisco perhaps not Boston you could live a good life on, right? And taking home 100,000 a year being your own boss. You know, taking a day off to play with your kids when you want to. Like, there is a part to that life that’s who could ask for anything more. You know, like It’s okay not to work 80 hours a week and hope for a unicorn.

It’s nice having a unicorn, but it’s okay. Not

Jeffery:
I like it. I like it. Very positive, very positive. All right. We’re gonna jump into the rapid-fire questions.

Igor:
Bring it.

Jeffery:
All right. And we actually didn’t talk about some of this. So this will be good to.

Igor:
Yeah, I have not heard. I have not opened the prep.

Jeffery:
Oh, even better. So whether the random questions, this is good. Okay. So why do you invest in start up companies?

Igor:
Because I did not know that was a thing in the first couple of startups that I did.

Right? Um I’ve had so many failures and there were all bootstrap. I didn’t even know that investment was on the table. I was young. You know, whatever these days, it’s more in the mainstream and you’ve got shows like shark tank and all that kind of stuff. So people know it’s out there, But really it’s to give back is to give others an opportunity. And so, you know, if I could save someone 10 years of mistakes that I made, I see it as a positive.

Jeffery:
Well it’s understandable when you’re building your first company at 12 that you might not know that there’s angel investors out there. So um okay, so how did you get started? What was the what was the impetus of getting you in the market?

What got you to say I’m going to invest in this company.

Igor:
I had more money than I knew what to do with, not in like a like a stupid way, but like I had I had a couple of $100,000 and I said, you know what can I do with this? Besides put it in, you know, some sort of account. And so I’ll tell you part of that was me being stupid because the very first investment I made, it was also my biggest and the one I regret the most, right. Since then I’ve kind of like, you know, found a good cadence and I know what to look for and all that kind of stuff. But I was, you know, uh, coming hot off and eggs and I’m like, let’s do it, let’s spend some money.

Jeffery:
We learn right. And then you find your balance. That’s good. What’s your favorite part of investing?

Igor:
Hell. It’s not the return. I haven’t seen many of those yet. Uh, it’s not the due diligence is because those are less fun than they should be. Honestly. I it’s meeting, uh, it’s meeting smart people. I I love, I love just meeting smart people, you know, and you don’t know all the time that you’re like having lunch with someone is going to change the world in 10 years and oftentimes that’s not often times, but occasionally that’s the case.

And then you can look back and be like, oh yeah, we got a burrito. You know, I, I think that part, it’s actually really awesome. If I can participate in that success, then, you know, that’s a cherry on top. But just just meeting smart people having smart conversations and not being bored.

Jeffery:
I love it. How many companies do you invest in per year?

Igor:
Ah, The first couple of, so the last couple of years has been 3-4, not a lot. The first year was five or 6 and that kind of tapered off the last year or so has been less because I’ve been focusing on fast CTO.

I’m kind of throwing that. Uh, so it’s been mostly, uh, uh, follow on investments.

Jeffery:
Okay, You’re above average. So that’s good. Um, any verticals that you focus on?

Igor:
So Igor the person invest in what he knows. Igor working with other investors is a lot more spread out. But the verticals, so I, I don’t like, uh, I decided like everything. I don’t understand. There’s no beverage. I don’t do any food, beverage. I just don’t, I don’t know. That seems to be a crap for democrats to me, right? Because you just never know. Uh, so it’s mostly some sort of tech or science, even if it’s light science, it’s like, there’s some sort of a thing there that I can wrap my head around. Not like how many whole foods can you get in the door with that? To me? I don’t think so. No. Widget, no, no, like shark tank type stuff at all.

Jeffery:
Yeah. Okay.

Igor:
I love watching Shark but I just don’t want to invest.

Jeffery:
No, that’s good. Do you have any due diligence requirements that you like to ensure that are part of when you’re making investment? To make it a commitment is that could be the team, it could be paperwork. Anything that really stands out that you say, you know what? If I’m gonna invest I need these three things.

Igor:
That was obviously the team, I need to be able to have a conversation with the team and walk away from that being, they’re not going to throw away my money. You know, they might fail, but it’s not because they’re incompetent, right? Uh, I need to look at the deck and I need to walk away from that being like they understand the domain. Um, and this part is maybe a little snooty of me, but if they’re spelling errors on your pitch deck, that’s an immediate no. Right? Because if you don’t care enough when you’re asking for half a million dollars to spell check your spelling, your deck, then you’re not gonna be careful with my money either.

And I feel like I could say that because english is not even my first language, right? So I don’t feel like I’m being, you know, uh, elitist about it, but spell checking. Yeah.

Jeffery:
Hey, I like that you come up with a little formula that works and if you catch it and you figure it out and you look back two years later, like glad I didn’t invest in them, they couldn’t even spell travel

Igor:
Entrepreneur. That’s a hard word. I, you know, I spell it wrong sometimes too. But then I right click and I take the right spelling. I don’t just leave it in the deck.

Jeffery:
I think we’re used to uh, having spell checker come on and when it doesn’t come on, we then just accept the spelling because you’re reading over it too quick and then you realize it after.

Igor:
But I do agree with you on that. I will say like for April fools if like Windows and MacOS got rid of the squiggly underline on misspelled words, you know,

Jeffery:
I think you look good.

Igor:
A lot of, a lot of emails are gonna go out that don’t look right?

Jeffery:
Yeah, I agree. Okay. Do you lead rounds?

Igor:
Do I what? Do I lead rounds? Um, I don’t feel like I have the whole kind of confidence to do it. I can do the tech side. I can do the finance these days to some degree of certainty, but you know, like I can’t do legal, I don’t know what to look for. I can’t double check your contract, you know? So I definitely need help and so no, I don’t lead rounds.

Jeffery:
Okay. Do you prefer any specific terms? Pref shares, common shares, safe? Anything you prefer?

Igor:
You know, the group on wealth doesn’t like safes. I have invested in safes and for me, so it depends on your mentality, Right? Because my mentality is I’m never getting this money back. I don’t care about cruz infrastructure, right? Because I’m never gonna call that note, right? I mean, earmuffs everyone, but I’m never gonna call that note, right?

So if you’re the type of investor that you know, calls notes, then you don’t want safes. If you’re the type of investor that cares about like, you know, a few percent here because of one capital gains start getting calculate and all that kind of stuff. When you don’t like safes. Uh you know, my mentality is, you know, of course, like at the end of the day, I want more money than less.

But if I’m walking away with, you know, 10 million or 9.5 million, it’s not that big a difference for me, right? Sounds

Jeffery:
I like it and I think it’s it’s depending on how early it is because the earlier the investment safe, so pretty common, meeting friends and family. And then as you start to expand, you kind of want to make sure that you’re protecting your investment a little bit better outside of a safe. So, and because your earlier on it probably fits okay at that beginning and then you decide from there what fits after.

Igor:
Yeah. But that also depends, it’s very geographic uh to like safes so much more popular on the West Coast and they are in New England uh Valuations are way different. Like, you know the average value, like when I look at a convertible notes, the average cap that I see between three and six million. Obviously in San Francisco, they started like eight, you know, so like you know,

Jeffery:
80? 80?.

Igor:
Yeah. Yeah. But it’s it’s yeah, it’s very different. So I do I have one safe in my portfolio which I’m neither kind of gung ho about nor whatever.

It’s not doing any worse or better than the convertible that are also not doing much.

Jeffery:
No, fair enough. Do you take board seats?

Igor:
Do I take board seats? Yeah. So for sure. Especially. So this is a smart money thing, right? I don’t demand them. Uh there’s been a couple investments that I said, look, I don’t need to be on the board board, but I want to, I want, you know, part of my equity to be advisory shares.

I have been on, on a bord or two. And, uh, I find that it’s helpful, but it depends on the type of company, right? Like I don’t want to be on the board just to be on the board. I want to be on the board where I can and bring value with my back.

Jeffery:
I love it. All right, we’re gonna, we’re now going to shift into the personal side of this and now we’re going to dive into that one or two points. The first one we will ask is what’s the one thing about you that nobody will know or two?

Igor:
All right. So I’ll give you one that most people don’t know. And I’m saying this and there’s a chronological reason here. So when I was little, I was about 6, 5 or six, I was running down the street in the park and I tripped and I fell and I hit the chin on a curb and I bit off the tip of my tongue and it was hanging by a thread.

It was like uh maybe the size of a dime, a. US Dime. I don’t know if you know what it looks like, the size of a dime and it was a pretty hefty piece. Right? And so most, you know, most american parents would take you to the hospital to get stitches. Um fortunately or unfortunately I was with my grandmother at the time who was a World War Two field surgeon. And she looked at my hanging tongue and my gushing blood from my mouth and she basically said no big deal. Just hold it against her teeth for a couple of days it’ll heal and well it did heal. I have a little bit of a scar here. Uh I can still roll my r’s like any respectable Russian. Um but I do have a little divot here and and my grandmother actually passed away last week. She was 100. But I always have this little scar to remind me of her.

Jeffery:
That’s awesome. Well sorry to hear that, but she sounds like she’s created some amazing memories.

Igor:
So it’s good. So most people don’t. Yeah, that’s a good one. You made me think that that’s one that most people don’t know.

Jeffery:
Well I like that, yep, brilliant. Okay, favorite sports team.

Igor:
Favorite sports team. I don’t have one man. So I grew up playing individual sports, I grew up doing diving. I was actually, here’s another one that most people don’t know.

I was in the junior olympics for diving. And so I was never really into like big into like team sports. And so when I moved to America, because America is way more into team sports and than Russia is And I remember, so I moved here in ‘92 and the first kind of like year we were here, I was still not really speaking english, we watched the Super Bowl. And I think it was 1993. But basically the Green Bay Packers were in the Super Bowl that year and the quarterback was Bradford. And so basically I just decided like I like Bradford, I’m gonna follow him. So for many years I was a Green Bay packer fans then I was, you know, a Vikings fan.

And then when Brett Farve retired, I was like, okay, who now? And so I picked Peyton Manning so that I was a cold stand for a couple of years. And so I picked somebody I admire and then I follow that person to whatever team, basically. Right now I’m a free agent. There’s not anyone that I’m following because Peyton retired and I don’t like his brother that much and I definitely don’t like tom brady so

Jeffery:
Well in a quick little search, it was 93 so uh there you go. So that’s awesome. Well you still have fans of sports that your fans of. So that’s good. So it just gives you a little bit of a discussion point regardless. So that’s cool.

Igor:
I like the olympic sports, like gymnastics. I like, I like the kind of stuff most americans don’t like, you know, like gymnastics and fencing and like all the esoteric things, diving,

Jeffery:
those are good sports man. It’s individual crushing. That’s good. Alright, favorite movie and what character would you play in it?

Igor:
I’m going to answer the first part as if there is no second part because with the second part it sounds silly but my favorite movie is Commando.

Jeffery:
Okay

Igor:
Because it’s just an incredible movie in all respects. But obviously like I can’t stand to be Arnold Schwarzenegger in it and but I don’t know who else —

Jeffery:
Why not? You can be Arnold!

Igor:
I guess I could be. I have carried logs but there are much smaller.

Jeffery:
It’s more about more about the character. Like how the character represents you and how you will make it through as a Commando? So if that’s the type of character that fits your your you you feel that that when he watches your like that’s how I would do it, then that’s kind of the —

Igor:
Commando is basically Taken but 15, 20 years earlier where someone kidnapped his daughter. Except in Taken, he goes after them and kills a couple of people. And in Commando he finds an island and fights in the army on the island. You know like mm Yeah, I’d like to stay too. If somebody kidnapped my daughter I would do that. But I don’t know if I have those particular set of skills but I do my best.

Jeffery:
It’s a it’s a great selection. It’s good. I like that. I’m uh I haven’t seen commando probably since I was a kid.

So I’m probably gonna have to watch this watch.

Igor:
So I think it’s an incredible movie.

Jeffery:
All right. I love it. All right. Last question, what’s your superpower?

Igor:
My superpower? The superpower I’ve always wanted was to fly but I don’t have that or do I? But I don’t uh but uh like uh you know the typical answer, I have been asked that question before. Once or twice. I think my superpower is not being disappointed with disappointment, right? Because basically, especially as a co founder, uh you know, you passed up on a lot of things and there’s an investor, you pass up in a lot of things and if I basically, uh if I got stuck on the things I passed up, um I would I would be stuck forever.

So basically, I think my superpower is just being able to say, okay, that company I passed up on just went, IPO, that’s a bummer. But you know, it is what it is. You can call it a mistake because he knows,

Jeffery:
Yeah, you can’t beat yourself up on something. They could’ve, should’ve, would’ve, right, it’s one step sideways and three forward.

Igor:
Exactly.

Jeffery:
Well, no reason to go back, so that’s good.

Igor:
Sometimes, maybe a little how bad it’s like the cha cha slide, you know?

Jeffery:
Exactly, I like it. I like it. Well, I’m gonna say that Igor, this was, this was awesome. A lot of fun. I learned a lot. We shared a lot of good things. I think you’re doing a lot of great things in the angel world and keep doing that. But the way we like to end our show is that we like to give you the last word. So if there’s anything that you want to share to a startup or to an entrepreneur or want to be entrepreneur or to an investor, the floor is yours.

But again, thank you very much for your time today, Rockstar. You’re doing awesome. I love it and thank you for sharing with us.

Igor:
Thank you. I appreciate it. Uh listen, um, I’m gonna say one thing is going to sound salesy, but it’s not, I have a company called Fast CTO, our mission is we don’t profit from startups, I’m not trying to sell you anything.

What we do is we help you avoid mistakes, the kind of mistakes I spent my lifetime making. I want to help you avoid them, so come check us out, we might not be what you need, but come check us out and if you want, you could scan this QR code and I’ll take you right there. Mhm.

Jeffery:
That’s awesome. I’m only gonna do this because we’re filming it so it makes sense to do it, but of course it’s only picking up your face right now, so I’m not sure it’s going to work.

Igor:
I don’t know.

Jeffery:
Well, it didn’t work because —

Igor:
Well, it’s fast CTO.com. You could spell it. I believe in you.

Jeffery:
I believe I can do this. Well, Igor, thank you very much for two secs. We’re going to pause but thank you again for joining us today. You’ve been awesome.

Igor:
Thank you.

Jeffery:
Okay, that was awesome. Uh Really enjoyed that conversation with Igor.

He shared lots of great little tidbits. Uh I’m gonna check out the movie Commando because I haven’t seen that in so long. But big fan love what they’re doing on the CTO side as a non for profit and just balancing everything out to help early stage companies, the FastCTO and just the whole overall qualifying tech and uh you know, Just validating things as you go forward. Lifestyle brands, lifestyle companies are good, you can make money. And then just the great ways that he looks at and invests in how he invests, so coding at 9 and 12. Fantastic. Either way he came up with some great material. So join us like us share. Thank you very much for joining us today.

Have a great day.