Mike Dudas has lived a storied career in the fintech industry. From Disney to Google to Venmo to founding ecommerce company Button, to building his own crypto-focused media company with The Block, Dudas has been there every step of the way along the fintech revolution. As an early investor in Bitcoin, he has also become a strong proponent of crypto and decentralized currencies.

But despite that impressive resume, Dudas retains a sense of humility when talking about his accomplishments, often prefacing each win he's had in his career with the phrase "I've been fortunate." But whether it was privilege that got him where he is or not, Dudas has become an authoritative — if at times controversial — figure in the world of fintech, cryptocurrencies and more. Gregory Ugwi, the co-founder of Thinknum Alternative Data and a personal friend of Dudas', sat down to interview about his story and his predictions on Bitcoin for one of Thinknum's Fireside Chats.

Ugwi: So you've been in payments for over a decade now. And today, it seems like a sexy space with Stripe and Venmo and all these big exits. But for me, it fundamentally seems like a boring tech thing. So why did you get into it?

Dudas: It was actually an evolution of what I had been doing for the decade prior. I became interested in fintech and payments in 2010 while I was at Google. Up to that point, I'd primarily been in media and advertising. So I spent three years at Disney, and then had worked at a startup here in New York that was an ad network. Then I moved to Google and worked on YouTube advertising. So that entire experience had exposed me to the top of the funnel of marketing and demand generation and what advertising is.

At the time, Google made Google Wallet to try to “close the loop.” Say Tide has this real world advert, purchased with advertising spend. And imagine that in their search ad or their display ad, they can attach a coupon. The idea with Google Wallet is that if you had a mobile wallet on your phone, and you tap to pay at Walgreens, and  basically transmit a Tide coupon, that I could then see that that ad had actually led to a purchase. 

To your point, is that the sexiest thing in the world? No. But is it interesting? And does it actually drive so much of the consumption economy? Yes. That product, Google Wallet, was pretty interesting to me in that it pulled together so many different things. Now, subsequent to that, I worked in even less sexy parts of the payment stack. [I worked at] Braintree, a predecessor to Stripe, which did developer APIs to allow for ecommerce payment acceptance. That in and of itself isn't super exciting and thrilling, but what it enables is for many more people to start businesses than were previously able to, and it created sort of the building blocks to things which have come since like Shopify. I think it gets more exciting when you look at it as foundational technology to enable other really interesting things to be built on top. And there still are parts of payments that are exciting; Venmo was the first payment app to have a social feed where you could kind of do funny stuff and pay somebody back for a drink. And I thought that was really interesting. I was excited to work on that.

Were you scared to leave Google? I know many people that work in big successful companies, and when they leave to join a startup, whether it's real or perceived, they think of there's a lot of risk. What was your mindset leaving Google?

I guess I consider myself very fortunate. I call it being born on second base or third base, right? I'm a white guy named Mike who grew up affluent in Connecticut, went to private high school, and because of that got a great education and was able to get into Stanford. It was this sort of self-reinforcing thing, where ultimately it wasn't as much of a risk for somebody like me who had those brands like Disney already on the resume to go out to Braintree. In fact, they had a term for it — the yo yo. People would go out and leave Google and then come back. It was almost encouraged. But again, I had a particular advantage being based in New York with a lot of brands already on my resume. It was less risky for me to do that.

Did you feel like it was a similar situation when you had to start your own company and actually leave like that startup? Did you feel like you could take the risk?

Yeah. Absolutely. There's opportunity costs, and I left a lot of guaranteed money on the table when Braintree-Venmo was acquired by PayPal, which had a really nice turn out. But it was definitely a calculated risk. The people I was able to start Button with had phenomenal pedigree and basically were already in the process of raising money when I joined up with them. So I would say everything that I'd done to that point was de-risked. Then frankly, by the time I left Button and solo started The Block, I had been able to build up kind of a public reputation through Twitter and just all the people I'd met over the 15 years of my career, to where, again, it wasn't as risky and I was able to raise money. [I was able to] go out and raise $2 million before we had a single customer.

You sort of hinted at this, but you're not an engineer by training. So do you think learning to code is important to be a founder, or not really?

So it really depends. It hasn't been for me. But at the same time, I haven't created a unicorn, right? Button is very successful and is worth hundreds of millions of dollars, and at some point, it will exit by IPO or M&A at a nice number. Hey, you know, if I was a multi-talented engineer with good business and sales skills, maybe I would have made better choices along the way, and the companies would be bigger. But I feel like I've been able to have success without personally understanding code. I was a terrible programmer. I'd be sitting next to my friends in Stamford and they'd be done with a program for a class, and I'd be like, “Well heck, that'd be another 10 hours for me.” It was just not something that I felt particularly great at. I have other skills, and they are valued. So anyway, because I've been able to partner with folks, it hasn’t been necessary for me to have that particular skill. I've stopped and started on the journey to learn to code probably five times over the last 15 years. And it's not been something that’s hindered me.

One thing I'll say is that you're one of the more charismatic people I know. In my opinion, it seems like you're naturally good at sales. Do you agree with that? And is there any way for people who are not naturally good at it to learn it? Or were you just always like that.

Yeah. I always had — call it the “raw material.” It’s hard to know if you’re good at sales. I was fortunate in that I went and got an MBA, which took two years and a lot of money and opportunity costs. And I wouldn't necessarily recommend that; I wouldn't do it again, particularly because I had business experience and some business education prior. But I was lucky that a CEO of a startup here in New York gave me the opportunity to be a “business development guy,” which often means sales. And yeah, I found that I was good at it.

"I think if you get outside folks trying to “add value” too early in the company's history, that's probably the most dangerous time. Because you're just trying to find product market fit. You don't need really strong, strong, strong opinions." — Dudas

A lot of it depends on what you're selling. There's different types of salespeople for different types of products and stages and roles. Sometimes you have to be a storyteller. Sometimes you have to be a listener or a consultative salesperson. I wouldn't say I'm good at all types of sales. I certainly like to talk more than I like to listen. So often I can be paired well with somebody like a solutions engineer — somebody who loves to listen to the client's problems and challenges and asks questions. But to your point, so much of sales is being able to be the friend and earn the trust of folks that you want to work with. And it's why I've been better with interpersonal enterprise sales, long cycle stuff, relationship-oriented sales, versus like transactional short cycle things.

Why did you decide to go to business school? You mentioned that you went into debt, and it wasn't as valuable [to you]. Why did you decide to do it? What were you expecting versus what did you get?

I didn't know what I wanted to do. I had kind of followed the traditional education path and ended up taking a hybrid job at Disney that touched on all my areas of study. I spent three years at Disney, but some people spent two and then went and did two years in private equity or two years as a VC associate. They just knew they wanted to be X, Y or Z, and I didn't. So getting another degree and another stamp of approval, particularly at that time when I think the MBA was still more valued perhaps than it is today, felt again like the low-risk thing to do.

So anyway, I came out of it and had no idea what I wanted to do. I took a job doing strategy at Kaplan in Chicago. So I was living in a city I didn't love, working for a for-profit education company that I didn't love. I was kind of lost. And, and had sort of a come to Jesus moment a year or so after graduating that I needed to go back to New York. I needed to move into tech, and I needed to switch from the strategy and finance type roles into something that's very different. So I just sort of did that sequentially.

Let's say I'm a young person, and I'm trying to figure out how to get ahead, trying to get skills that are valued in the market. What should I do? Should I be going to community colleges? Is online education better? What do you think?

There's no one-size-fits-all. What I will say is that there's a lot more great options for folks than there were years ago. I guess it depends on what students want to do. And it’s something I'm still interested in and passionate about, just not as my primary career. There are things like coding boot camps that are really interesting and innovative. Things like financing structures for students, income share agreements for once you get a job — stuff like that. I'm in favor of those things at a high level, and they have their peculiar particular implementations that can be better or worse. So what I would say is I'm really bullish on finding mentors to the extent that you can. I would highly recommend that people look at what qualities of an individual are important to success and in particular careers.

When you're hiring people, what do you look for? How do you decide, let's say, I want to get a job, and I want you to hire me in your next company? Do you have any special questions you ask in an interview? Or are there things you're looking for?

I would say the biggest thing is a deep curiosity and passion. With The Block it's very specific. If I'm going to speak in generic terms, no matter what the role is at The Block, you have to have an interest in or a passion for digital assets. Regardless of whether you're a journalist, researcher, technologist, designer, engineer, salesperson, if you can't get excited about the product, then you're not going to be good at the job.

By the way, nobody has a perfect hiring record. We certainly don’t at The Block. I’ve gone through editors who just weren't particularly passionate about crypto, so they weren't having fun with the jobs and weren't particularly productive at it. So that's one — and I’m speaking here as if everyone has the luxury to do what they love. Two is that I think your references are more important than ever. I couldn't tell you, for example, where most of the folks that we've hired at The Block went to college — even ones who are two years out. [That’s because] references and the portfolio that you've built up is the most important thing these days. In fact, I'm not doing a lot of hiring right now since I'm the chairman at The Block, but when I'm referring somebody to our CEO it's typically coming through a reference. 

So your reputation and the relationships that you build over time are increasingly one of the most critical parts of your career. Now that being said, that doesn't mean that you have to go out and you know, be friendly and have glowing references from every single person.I think if you're not evoking some sort of passion from people one way or the other, maybe you're not like really pushing limits and doing interesting work.

You've had a lot of success fundraising; It seems like it comes naturally to you. I don't know if people know this, actually, but when we were raising our Series A, I’d say you were the most helpful person for generating VC interest in us.

I appreciate it.

You’ve raised tens of millions with Button and with The Block. So do you have any fundraising advice?

The biggest thing is to be very decisive about what you're doing — your objectives. Why, in other words, are you raising the money? Why are you raising that amount? Why are you going to these specific investors and persuading them that this is unique? I think the biggest thing is just creating the perception that there is scarcity and urgency. Like, “Hey, this is a time-boxed opportunity. It's a hot moment deal. There's a grand vision here and we need X money to do Y and Z. And that's going to get us to this next milestone.”

You have to create that urgency and born out of confidence, certainty and vision. The other piece is you have to have access to the people who have money. I’m fortunate  — I'm 20 years into my career, so I've met a lot of folks by working in startups. I had a bit of a built in network and access, so that benefited me. But like you said, I've worked with people who didn't have the same level of access, and many of the most successful ones are people who have been hungry and scrappy and persistent and aren’t shy about saying why people should support them and help them and why what they’re doing is wonderful.

I get in trouble for saying this sometimes, but I think there is an obsession that VCs feel the need to argue that they add value [to a startup]. I mean, being a VC must be very hard. But access to capital, for me, is the main way they add value. But for some reason, they're just obsessed with saying, “Oh, we will help you with your business.” That's just not practical. Do you agree with that, or what do you think?

I think if you get folks trying to, to your point, “add value” too early in the company's history, that's probably the most dangerous time. Because, like, you're just trying to find product market fit. You don't need really strong, strong, strong opinions. With The Block, for example, we raised smaller amounts of money from a lot of folks, and basically dictated the terms of when we needed help. I think you have to be strong as a founder and say, “Hey, I need XYZ,” or “Here’s how you can be helpful,” and dictate those terms versus having people sort of distract you with things that aren't useful. I've been fortunate to have good experiences with VCs, for the most part. I think it's up to you to control that as the entrepreneur.

So now I'm going to ask about Bitcoin. I think everyone is trying to get rich off Bitcoin. You're the person that I know, personally, that probably knows the most about Bitcoin. So how did you first get into it?

It was 2013. I was at Braintree. We processed payments for Uber and Airbnb and a bunch of other companies and began a conversation with Coinbase about if we should add Bitcoin to the available payment options. PayPal ended up buying Braintree before that deal ever ended up going live. And it turns out now that Bitcoin really hasn't been used for that type of ecommerce payment. Because it’s appreciated so much and it's been volatile, people want to hold it and speculate on it versus use it for payments. But anyway, that conversation was the original way that I became aware and interested in it.

"On the crypto spectrum I'm viewed as really liberal. If I look at my more techie friends, they would probably view me as more centrist. And then the New York media people who follow me, because I was CEO of a media company, probably think I'm conservative." — Dudas

Around that time Chamath Palihapitiya wrote a piece that described Bitcoin as what he called “schmuck insurance.” So if the world went to hell, then you've got this scarce asset with a fixed supply cap which is censorship resistant. The money of the internet. And that appealed to me. And I think he said people should put 3% of your net worth into it. I guess I was early, but not as early as many folks that I know. I jumped into the space full time at the peak. I believed in it then and believe in it now. There's some really interesting things happening. I believe very, very strongly that  having non-state controlled, non-fiat money alternatives is important, and will continue to be important. Today it's on the fringes, but I think over time, it will become much more central to many people's lives. There will be booms and busts and bubbles, and that's a natural part of how money is created. So we're in another one of those booms. And I think this particular one has a pretty good long way to run from where it is today.

At some point, didn’t you put all your liquid net worth into Bitcoin?

So for opsec purposes, I don't like to talk about it. I lost my Bitcoin in a boating accident years ago (laughs). You know, putting all your liquid net worth into Bitcoin for the average person is probably too risky. But I do know many folks who have what they would call irresponsibly long positions in cryptocurrencies. And those people have done tremendously well even through booms and busts. And, yeah, I don't think these things are going to zero. So I think people who maybe put more of an allocation than then the common wisdom might recommend are going to do really well over the next decade.

So now I think we're gonna move on to sort of more social views. I think we'll start with Coinbase. As you said, you had some interaction with Coinbase. I actually think you raised from them and you returned like $25K. So how do you feel? Do you have any thoughts or any strong views on when Brian, CEO of Coinbase, came out and said he wants his company to be apolitical?

I sort of regret giving that money back. I think that was me sort of responding to these Bitcoin  mobs that I've subsequently lost more respect for as I've seen them espouse their views over time. I think they are more closed-minded and cultish than I think is healthy and have respect for. Anyway, yeah, I don’t think I should have returned that money. Coinbase’s political stance — I’m not gonna use my words to describe their mission — but hey, is it something I personally agree with? Is it how I would run a company? No. I encourage people to discuss social issues that are critically important to them. At The Block, people are free and encouraged to discuss matters that are either work related or social. Coinbase isn't a place that I would work. But I still have wonderful friends who do work there, who just have different philosophies. 

How do you feel about Twitter booting off Trump? Do you think tech companies have to get involved? Where do you draw the line in terms of free speech?

So I'm not an expert. But here's what I would say: We're in the midst of what I would call a still-raging emergency. Call it what you want — you can try to minimize it, but it was pretty clear to anybody who watched that there was an attempted assault on the Congress of the United States of America. Five people died. That's criminal behavior that I would argue was encouraged by the President who obviously knew that something of that nature was going to happen. So I would say I'm comfortable, personally, with people in an emergency acting when someone violates their terms, and then saying “We'll figure out some of this other stuff later.” I don't like that most of these tech platforms don't have consistently enforced, well-regulated policies, and that it's sort of come to this where they've basically opened themselves up to be a bigger story than the actual malicious activity that's happening. 

I think that it's sad that you have effectively a fascist president that the military would support in a minute who's able to sort of twist and manipulate these platforms to such a point that now they look like they can sort of be attacked for inconsistency. Long term they have a reckoning to do in terms of how they're going to deal with this. But, you know, I don't believe it's a violation of Trump's freedom of speech to turn his account off when people are dying because of activity that he's inciting.

You're an active Twitter user. So when you were starting The Block, would you agree that you used to be more controversial? You used to get into beef all the time.

Yeah, probably too much. And it was exhausting. And frankly it just kind of fell into this pattern of almost getting addicted to the drama. It was to some extent intentional and useful to draw attention to what we were doing. But then you get into pettiness and you know, it just got to be too much. It burnt me out, candidly. I'm not proud of some of the things that happened, but some of it I am. I've started to just delete my tweets regularly. But they get seen. I know, because I get feedback from people and people generally know what my political, social views are. On the crypto spectrum I'm on sort of the liberal side — like, I'm viewed as really liberal. If I look at my more techie friends, they would probably view me as more centrist. And then the New York media people who follow me, because I was CEO of a media company, probably think I'm conservative. Like, it's big, and all these people are fighting with each other constantly. And I'm like, sympathetic to all of them at different times for different arguments. So it's a, it's a tough thing. I use Twitter more ephemerally to comment on things of the moment. That's where I think it's most useful.

You mentioned you moved from Chicago to New York. And as long as I've known you, you’ve called yourself a New Yorker. It seems like New York is important to you. Could you see yourself moving to Florida, for example?

No chance. It's a big part of who I am now. I can see myself moving with my family to the suburbs, but you know, I think a lot depends on how the city recovers. But I love the city, New York City is the absolute single best place on Earth. You know, just the incredible diversity of every type. And particularly the business diversity is just wonderful. Every industry — tech banking, you name it — I love that I can take a call and be in front of the New York Stock Exchange chatting with somebody in a 15 minute walk. I think it'll be more livable. It's gonna be tough couple years, and I think after that, it's going to get back to being more diverse, more livable. Already in Tribeca, which is where we live, the median income has dropped dramatically. You have a bunch of families and individuals earning, you know, under $200,000 a year who have moved in, so it's gonna make for a much more eclectic and fun, I think, city moving forward.

As a final question, I just want to know: Is there anything you've watched or read recently that was inspiring?

So one thing that made me more comfortable about our global future was a book by a guy named Peter Zeihan called “DisUnited Nations.” It talks about a sort of a post-global order world whereAmerica and its allies aren't necessarily fully dominant. It made me very confident in America's position relative to China. It might be, by the way, contrarian, but it was a really well-written book. 

I've also spent a lot of time really trying to learn about the history of banking and money. I’ve been listening to an Alexander Hamilton audiobook by Ron Chernow, which is phenomenal. I just finished a book called “Lords of Finance” about the four central bankers, US, UK, Germany and France, in the period from 1915, to 1935. The period before the First World War leading through the roaring 20s, to the Great Depression, I think it's really relevant to what we may be going through now — Maybe the “roaring” part. I think there's gonna be hell to pay at some point in the next three to five years.