I sat down with Constantin Kogan last week after we randomly met in Salt Lake City. We both live near New York. Sometimes the universe has a sense of humor.

Konstantin is the founder of Holistic Capital, a multi strategy investment firm focused on digital assets. He also runs a podcast called Holistic Investments. Over 100 episodes. More than 600,000 followers across platforms. Not bad for something he started during COVID while stuck at home.

But the interesting part of his story is not crypto. It is not Bitcoin in 2012. It is not Ethereum in 2016. It is not being early to hedge funds or registering with the SEC.

It is this: social capital is capital.

During COVID he found himself in a tough place. Like most of us. No travel. No meetings. No momentum. He asked a simple question. What can I do that I actually enjoy? His answer was long conversations. Honest conversations. The kind you have in a kitchen at midnight over wine.

So he started a podcast.

No monetization plan. No big strategy. Just curiosity and discipline. For five years he made nothing from it. Most podcasters quit before episode thirty. He kept going past one hundred.

Why?

Because he was not optimizing for money. He was optimizing for relationships and learning.

That changes everything.

We talked about failure. I asked him about bad trades. Crypto winters. Market crashes. He surprised me. The real failures were not financial. They were relational.

Picking the wrong partners.

He described business like a marriage. You can survive small disagreements. But when a real crisis hits, that is when character shows up. Do you share a vision. Do you share values. When it gets ugly, does your partner protect the mission or protect their ego.

You cannot really test that in advance. There is no checklist. No personality quiz that guarantees success. At some point you rely on judgment and instinct. And you accept risk.

That is uncomfortable. But it is honest.

We also talked about investing. Early in his career he focused on technology and timing. Now he looks at people first. Ideas are abundant. Execution is rare. Motivation varies wildly. Some founders want status. Some want money. Some want to prove themselves. Some want to change the world.

Only one of those types will survive when things get hard.

If you are building something, remember this. Investors are not just evaluating your deck. They are evaluating your stamina. Your alignment with your team. Your ability to handle conflict without blowing up the room.

And if you are thinking about starting a podcast or some other media project, understand what you are signing up for. It is a business. It consumes time. It demands consistency. It does not pay right away. Maybe not for years.

But it builds something else. Reputation. Network. Intellectual capital. A record of your thinking.

That can compound.

Konstantin does not even call himself a VC anymore. He trades liquid markets now. Algorithmic strategies. Volatility. But the podcast still runs. The network still grows. Yesterday he met the co founder of Venmo and invited him on the show on the spot.

That is how opportunity works. Quiet compounding. Relationship by relationship.

You cannot fake that. You have to show up. You have to publish. You have to keep going when the numbers are small and the monetization is zero.

There is a lesson here.

Build things that create optionality. Build things that connect you to other capable people. Build things that make you better at thinking and listening.

Money follows. Sometimes slowly. Sometimes indirectly. But it follows.

In the meantime, protect your partnerships. Choose carefully. Align early. Agree on how you will handle conflict before it arrives.

Because markets rise and fall. Technologies shift. Cycles repeat.

Character does not.

TRANSCRIPT

Welcome back to keep going. A podcast about success and failure. I’m John Biggs today on the show. We have Constantin Kogan. He’s the, uh, GP at holistic capital. And you also have a, really cool podcast, which I’m going to be on eventually. So I get to actually,

Constantin Kogan (01:18.537)

Mmm.

John Biggs (01:37.954)

meet your audience. But we met just a week ago and you have a really, cool story. So tell us what you’re up to, Constantin.

Constantin Kogan (01:47.235)

Hi, John. First of all, an honor to be here. Yes, we met in Salt Lake City out of all the places, ironically, live in close by in New York. I don’t know where to begin the story. guess maybe just a little bit of background. I’m originally from Ukraine. was born and raised there, 11 years in the United States. I started my career as a...

John Biggs (01:56.236)

Yeah.

Constantin Kogan (02:12.651)

I’m a modernism future trader. Chicago Bota Trader was my first venue where I started to explore financial markets. From there, went through a hole and bought my first 5 Bitcoin in 2012. 2016, I a conscious choice to go all in when Ethereum got out and...

thought that programmable money is definitely going to be the future of tokenization of all the assets. 2017, I became a partner in the first crypto fund of hedge funds in the world. We’re the first SEC registered firm. And from there, you know, I had a wild journey co-founding three companies, you know, investing in 80 plus venture startups and running my own.

you know, my own hedge fund, working for hedge funds and now focusing on holistic capital, which is basically a multi-asset, multi-strategy investment firm, mostly focused on digital assets, but eventually we will work with different assets on blockchain as well, which I think that’s where the future is going to. And also, as you mentioned, I...

also run Holistic Investments, which is the podcast which I started during COVID time. My first guest was Dan Moritz from Pantera Capital because we invested in Pantera so we good relationships with them. Since then, I 100 plus guests on my show and enjoy learning from incredible individuals.

John Biggs (03:49.278)

And you’ve got you got like 600 plus thousand followers across your across all your platforms. What do you think led to that level of success? And what is what does that give you as a VC? Like I know what this gives me as a I don’t know, just a putz on the internet. But what does that give you as a VC?

Constantin Kogan (03:55.957)

Yes.

Constantin Kogan (04:10.313)

Well, to be completely transparent, I don’t consider myself as a VC anymore. Like I used to be. Right now I’m...

mostly with trading more liquid assets, right? So you can think about it as algorithmic trading firm, high frequency trading, right? Closer than, so I used to be at VCN. I thought that was incredible opportunity in emerging markets, right? But regardless, what it gives me, it gives me network. I think...

Social capital is another form of capital, right? Not necessarily like people who invest in you is your, you know, main business partners in life. You know, some people like stay with you regardless of whether you succeed or you fail. And I think the more value you bring to other individuals, like what look what we’re doing today, right? You’re the first

who allowed me to be on your podcast, which I’m very grateful for, and then you’re gonna be on mine, and that’s hopefully gonna inspire others to do the same and share thoughts, you know, learn from each other. I would say intellectual capital and social capital, that’s what’s the primary goal for me, and that’s how I’m giving back to the world by educating the future generations.

John Biggs (05:28.396)

Mm-hmm. So tell us about the growth of this media empire, I guess you could say. So you started out just deciding to do this. What was the impetus? Why did you want to do it?

Constantin Kogan (05:40.105)

Well, media empire, it’s a big word. love how you frame it. Future media empire, yes. Yes, I appreciate it. Look, I, again...

John Biggs (05:47.03)

Yeah, we gotta tuck each other up, yeah.

Constantin Kogan (05:54.363)

Wholeheartedly, was in a very tough spot during COVID. I think it was a very challenging time for everyone. And I thought to myself, what can I do? I mean, we’re sitting at home. There’s not much to do. you know, everything is digital anyway. You cannot go out. And I started to ask myself, it was more of a soul searching exercise. Like, what can I do to at least do something what I love to, you know, have a cohesive discussion and also somehow impact

others to inspire them or to help them in some way and that podcast format was the most relevant for me. I’ve listened to a lot, I’m a big fan of know like Joe Rogan, Alex Hermosy, know and Alex Friedman and many other like greats know people who went bold and started to invite other individuals, have long discussions with them so my

My format is about 60 minutes, right? So it’s enough time to learn about a person, about their journey, about where they’re coming from, and also how they achieve this success. And also ask them uncomfortable questions, which allows to bring less controversy, but more about what were the failures? What are the learning lessons? Something that you would not talk on your board meeting or somewhere in the traditional media, right? So more like honest, friendly conversations,

you will have when you’re drinking wine with your friend in the kitchen.

John Biggs (07:30.606)

So tell me about some of those failures. think you, I mean, right now we’re looking at a crypto winter. So that sounds like, it sounds like you might have some issues right now, but tell me about the failures as you move through and try to enter this space.

Constantin Kogan (07:44.255)

Yeah, as a matter of fact, we’re doing great. maybe we like when you’re trading.

the market is a strategy, you’re not like long like any asset like we’re making money even shorting right now. So for us, the volatility and big spikes is where we make most of our money. And that’s the exciting part. Like, and that’s when I finally understood after three cycles in the industry that how to navigate the markets. So that’s number one. The failures mostly, ironically, I wouldn’t call them financial decisions. It’s mostly

who you’re going with. So I would say how to pick your partners. Like, and I think that’s one of the most challenging parts because if you think about a business, it’s like as a form of marriage, so to speak, like a very big connection you spend with your business partners a lot of time, you’re building something, it’s your venture is like your baby, right? And when there is, I would say, not clear

understanding of what is the vision, how do you work together, like you know what’s gonna happen next, like when the actual challenges come into play, that’s when you learn the character of a person, that’s how you learn how they react, that’s how you learn if they’re gonna be supportive or they’re gonna put you down or maybe even like publicly humiliate you, like there’s a lot of things that are completely unknown besides the business challenges, we’re also talking about like

basic human to human relationship. And I would say that the biggest learning experience for me as a failure is how to choose the right partners and how to make sure that these people not only share your vision, but also there will be for you when it’s going to be the hardest, when nobody will want to support you, when the market is against you. And in these moments, it’s incredibly important to have a person who

Constantin Kogan (09:46.024)

is basically you’re person that you consciously decided that no matter what you go till the end and you make it a success.

John Biggs (09:53.582)

I mean, have you ever was give me an example of someone who who didn’t fulfill that for you.

Constantin Kogan (10:00.043)

Well, I don’t want to put names, right? But I would say, I should say if you read statistics in traditional VC companies that are well-funded, let’s imagine even they found product market fit and everything, one of the third aspects why companies fail is because of the pure misunderstanding and quarrels between the teams, right? And the founding team. So it’s an ego issue, right?

John Biggs (10:03.918)

We’ll just kick. Yeah, sure sure sure

Constantin Kogan (10:29.578)

There are people who are money driven, there are people who are purpose driven. When you are purpose driven, like you’re always trying to ways how to mitigate certain conflicts, how to find a way to harmonize a relationship, even though you might disagree on very particular topics, right? Very tactical, pragmatic business decisions, but still respect.

another person who might disagree with you. And then you find out that some people besides can be brilliant, analytical, and very active in business. They might not have, let’s say, what we call in a common sense, like high emotional intelligence. And that equals to...

bigger misunderstanding, right? When you like, again, marriage is probably one of the most like relevant examples when two people, let’s say they’re not on the same page, it creates like an environment where you might be successful in other aspects of life. But when you come back home, let’s say, and you were not like feeling.

that it’s the most supportive environment, then everything else becomes challenging. It becomes, I wouldn’t call it obsolete, but I would say it becomes irrelevant. that’s, would say, the most important example. whenever you’re picking people who you want to go with, and by the way, that’s also...

relevant for the partnerships, right? People who will be, let’s say, your investors or people who will be your customers, who one of the biggest ones. That’s one of the most important aspects. Are you in the same page? Do you have the same values? Is it like, are you going to be able to work long term together?

John Biggs (12:21.326)

Okay, yeah, fascinating. So what do you do to test people before you trust them?

Constantin Kogan (12:30.121)

You know, it might sound funny, but I don’t think there’s a way to test it. I really don’t. think it’s some... somehow it’s a gut feeling, you know, like it’s when you pick a partner you see immediately, like whether there’s gonna be potential conflict and whether you’re gonna be able to navigate this conflict so that you come out...

the same as you started your relationship. And yeah, sometimes it’s more about the examples of life, the practical issues that help you. For example, my current business partner, know each other for 17 years. So we’ve been through a lot of hardships. We know how would each one of us react.

And sometimes you know a person from an industry or somebody referred this person to you and you meet for the first time, you think, oh, wow, it’s a great idea. We can make a lot of money together. But eventually, when a serious conflict situation arrives, like maybe small things you can dodge or you can raise above those issues, but then the big one destroys everything. And it’s impossible to know in advance. That’s the irony of life.

So you have to just have, mean, some people do psychometric analysis, like astrological analysis, right? I don’t believe it works. It’s just a matter of that you agree from the get-go. What are you going to do? Not if, but when the issue is going to arrive.

John Biggs (14:13.43)

OK, very interesting.

How do you make decisions on what to invest in, what to buy, that sort of thing? Like, let’s say we’re talking to an entrepreneur right now. What would you be looking at when you beat them?

Constantin Kogan (14:29.961)

Well, as I mentioned, right now we’re mostly focusing on liquid market, right?

John Biggs (14:34.382)

Well, yeah, but yeah, but like before or just in general, because I mean, we have fairly.

Constantin Kogan (14:40.677)

Before as a startup, same, I look at the people a lot. Before I looked at technology and the scalability, whether it can be 10x, 100x idea, whether it’s a good timing, whether the market is ready, when they have a product market fit and they have some traction, whether they have some revenue or some goods, I don’t know.

downloads or like you know any like monthly average users like daily average users like you know that’s sorry active users right so but nowadays I actually look at the people more mostly like after investing in 80 projects and realizing that most of the startups are just statistically like they will fail like so the only question now remains in my head is like whether this is the right team to execute the vision

The idea can be incredible. The vision can be also like, you know, right on time, like on point. You have like backing, like, you know, of the top VCs or like angel investors. But then you look at the people and you think, okay, well, are they are in a good place, like in their life? Do they have enough experience? Are they motivated enough? Because motivation of founders can be also very different.

One founder can have, I don’t know, two previous exits and for him it’s like more of a like he really wants to change the world while other can it can be his first startup and he’s gonna grind to make it happen no matter what just because like he wants to you know prove himself like and there is other scenarios where people already just do it

John Biggs (16:12.398)

Mm-hmm.

Constantin Kogan (16:18.372)

for reasons because they need to do it, because there was a merger or because somebody told them that’s going to be a great opportunity. So that’s the most important, think, right now. You look at the people, you have multiple meetings, and you try to analyze whether they’re going to be the right fit for this particular idea to execute it.

John Biggs (16:40.47)

And for folks in your boat, they start up? Should they start a podcast or would you recommend it? Or is it a is it too is it a pain?

Constantin Kogan (16:44.169)

You know, starting a podcast is first of all, you have to think about a starting a business. I mean, you know, better than anyone else, it’s a very challenging endeavor. It requires a lot of time.

John Biggs (16:53.39)

Mm-hmm.

Constantin Kogan (17:00.173)

not always I will pay out immediately for five years. I haven’t been able to monetize it. I was just doing it for my own passion, right? You know, because I truly believe that learning from other great minds was something that I wanted to. And if at least like a few hundred people will be inspired by that, that was my motivation. But then you realize, okay, well, like you spend your own time, you spend resources, right?

you we’re spending right now, you allocate half an hour of your valuable time in life, right? Then you’re going to spend time on editing, right? Then you’re going to spend time on distribution. And then you ask yourself, is this going to be monetizable because you spend all this resources and you hope at some point it will be. And if you don’t have a clear answer when and how it’s going to happen, then the question is like, how long you’re going to last. Statistically, most of the podcasters who

go into this journey, they don’t last more than 30 episodes. So if you’re over 30 episodes and let’s say you get into 50 to 100, that’s already, that means you’re a survivor. The question is how big you want to go. That’s all.

John Biggs (18:14.74)

Mm-hmm. Yeah. mean, think I’ve got 260 or something like that. So I feel like I’m a survivor, but I’m in the same boat where it’s in terms of monetization is kind of silly. so where can people find what you’re working on?

Constantin Kogan (18:27.784)

Holistic investments you can Google my name Konstantin Kogan and holistic investments. I am an Apple podcast Spotify. I have seven other platforms There’s also a YouTube version of it right there. I put her telegram Instagram the short version of it YouTube obviously the full

So I’m doing right now in studio in New York. if any of your listeners think that you’re a great potential guest or you want to refer someone, feel free to go to my website, constantnikogon.com and there’s a form you can submit someone and I’m like my team would be happy to review it and come back to you. And yeah, it’s mostly relationship based nowadays. for example, yesterday I met co-founder of Venmo.

honestly was not planning to do that, right? And then I was very inspired, he’s building a new project and I was so excited about his vision that I want to support him. So I invited him immediately, the first moment we met. There are others who takes time, it’s a publicly traded company, so it takes me three months to book them, right? So I’m very open-minded to talk to anyone here, constructive feedback about the format, about the questions.

Sound, light.

John Biggs (19:50.478)

All right, very cool. Constantin, thank you for joining us.

Constantin Kogan (19:52.786)

Thank you so much.

John Biggs (19:54.382)

All right, this has been Keep Going. I’m John Biggs. We’ll see you next episode.