On The Brink with Castle Island - Dave Balter on Leadership, Humility and the Startup Journey (EP.97)

Episode Date: June 30, 2020

Dave Balter, the cofounder and CEO of Flipside Crypto, a business intelligence company focused on public blockchains, joins the show. In this episode we discuss: Dave's new book, The Humility Imperative, and the lessons he has learned from seven startups His POV on leadership in an emerging market like cryptoassets/blockchain Reflections on fundraising, remote working, personal relationships and more. To learn more about Flipside Crypto visit their website and follow Dave @DaveBalter

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and as a special offer, use the coupon code Castle to get 10% off. Head over to keys.casa to get peace of mind that your Bitcoin is safe. Today on the podcast, we have a recurring guest, Dave Balter. Dave is the co-founder and the CEO of Flipside Crypto, the Castle Island portfolio company. Flipside is a business intelligence company that analyzes the usage of public blockchains. So think about this as a data company that is really trying to understand what is happening on these chains and what people are using them for. Dave is also the author of a new book

called The Humility Imperative. It's a book about leadership and it's about his experiences as a seven-time serial entrepreneur. So I wanted to have Dave on the podcast today to talk about the book, talk about his personal leadership journey, and talk about the world of blockchain and where he sees the leadership journey for some of the executives and teams and projects in this space. We also spent some time discussing what's happening in the world of public blockchain, and specifically around applications. So we talk about where Dave is seeing the most potential for consumer breakouts. So this is a fun episode.

Without further ado, here's our conversation with Dave Balter. Brought down by bad mortgage investments, Lehman, which has 25,000 employees, will be liquidated. The federal government loans American International Group, AIG, $85 billion. This is a different kind of market, and the Fed is asleep. The federal government is stepping in to stabilize Fannie Mae and Freddie Mac, the two mortgage giants that have been threatened. by the housing crisis. The bank of England has pumped 75 billion pounds more into Britain's ailing economy with a new round of quantitative easing. You print a couple trillion dollars

and all of a sudden people start to worry. So out of this worry, we have something called a Bitcoin. Bitcoin. All right, so I'm very happy to have Dave Balter back on the podcast. This is your second appearance on the podcast. Are you honored? Oh, I'm incredibly honored. This is what, number two of likely a dozen. I know. We should have this be like a recurring thing where you're just occasionally on. and blustering. I don't want you to lose listeners. That'll be an easy way to lose listeners. Well, I'm excited. This is the first time I've had someone on the podcast that is promoting a book. So I feel like I'm a real podcaster now. This is it. I'm going to make you spell out

URLs. You're going to have to do all sorts of flogging of my work. A lot of people in the crypto world will know you. You're the founder and CEO of Flipside Crypto. But maybe for those in the audience who are not as familiar with you, can you just set the stage and give us your quick introduction? So yeah, currently CEO flipside crypto. This is actually startup seven for me. Even saying that maybe leads to some of the discussion we're going to get to, which is about humility and leadership and startup seven. That sounds very hubristic. Anyway, it is startup seven. I've had a couple pretty good exits over the course of time. I've been a venture capitalist with Boston Seed Capital. I'm an investor in about 60 different startups. I have

I sit on the board of the box center for the performing arts because I'm pretty into arts and music. I did not know that. It's good touch. Well, there's so much to talk about and I definitely want to get your take on what's going on in crypto, but let's talk about this book that you wrote. So the humility imperative. It's coming out on the 30th of June. So by the time folks listen to this, it'll be out. And I thought it was great. I read it last night. It was a collection of a lot of blogs that you've written over the years. What was the impetus for writing the book? It is. It's a collection of 37 essays. Some have been published on my blog, but some have appeared in Inc magazine, Forbes, startup grind,

Hackernoon, places like that. What happened here is over the last decade or so, I've been continuously sort of writing. But as I sort of started looking back at some of the writing, I realized it was really sort of a theme around leadership, around humility that sort of appeared over the decade. I would constantly write about fundraising or how to treat employees. and we're now in the crypto industry fully. And I was reflecting on some of the struggles of this industry, specifically related to leadership.

And I kept going back to my own pieces. Like, yeah, what would I tell somebody about this? And so it just felt like it made sense. Like, this is an industry that probably really needs a transformation of how leadership thinks for it to truly succeed. And so this felt like the right time to sort of put it all together into a book that people could digest. That makes sense. I mean, one of the things I really liked about the book was that it sort of is a rollercoaster.

Reading it, you can sort of tell where you were with a particular startup at the time you wrote it. And there's a lot of emotional angst in certain pieces of it. I mean, you're talking about getting divorced in one of these blog posts. You're talking about meeting your new wife and other blog posts. You're talking about firing people, hiring people. So I guess as you look back on your leadership journey, how would you describe yourself as a leader today, maybe versus where you might have been for their startups? Let's start maybe with a slightly different answer, which is really setting the stage for what is the humility imperative as it relates to sort of leadership today. So let's be clear, the imperative is not every leader needs to be humble. The imperative is as a leader, you are constantly at odds with the balance between being humble, which approach of listening

to others, knowing you don't have all the answers, respecting that you're on a learning journey all the time and confidence. The need to have your team follow you, to have VCs agree to give you capital, to have competitors fear you. And you're constantly in this arc of this tension between two sides. If I showed up at Castle Island and said, hey, you guys should fund my company, I got to tell you, I'm not really sure if I have the answers. And this, we might figure it out. You probably wouldn't put money into us. You show up at a VC and you say, hey, this is how we're going to win. That's not humble. And so that's really the arc of the book. And the truth is that tension is in every relationship you have in a company, your employees, your peers,

your bosses, you're external to the company, your loved ones. You're constantly in this battle. And so where I am today, I think in the book, you'll see some failures where we really sort of lost the thread of humility and failed. Where I'm today is like, I'm just, just in constant sort of sponge mode. I don't have the answers. I'm trying to drive forward with the vision we have. I'm trying to be strong leader, but it's still a constant tension. And how do you decide sort of who in your life and who in your company gets to see that side of you that is maybe the less confident side, the one that might be unsure of the total addressable market opportunity here, for instance? Well, I can tell you I was on a walk last night with my wife. I said, yeah, I'm going to

do a podcast tomorrow on humility with Matt. And she laughed in my face. Wait, what are you going to talk about about humility? And I'm like, no, no, no, it's about the struggle on humility. She'll call me right it out on it. Like, you can't, sometimes you're not the humblest guy out there. I got to tell you, but I am the best. No, I'm just kidding. I think it's an arc. If you go back to, if you worked with me at Buzz Agent 2005, I was horrific. I mean, I was like, everything was about, I had the answers. The company was on the cover in New York Times magazine. I thought we had to figure out every VC was begging to get into the business, et cetera. And I didn't show any of those people the true imposter syndrome that every entrepreneur

has at some point or I think most do. Today, I try to be much more clear about that. I'll say to my teammates like, look, I'm going to be strong in my conviction here, but I'm open to other ideas. Let's talk through them. That's hard to do. That's really hard. sometimes when you think, you know, the answer to let go and let someone else drive is pretty hard. Yeah, for sure. So thinking about this in the context of the crypto industry, there's a lot of things that I was thinking as I was reading the book. I mean, when you talk about humility and maybe uncertainty about the future of something, I would have to think that most entrepreneurs in this space are experiencing that. I mean, we're talking about a very small industry that we all think is going to get really large. But there are a lot of things that could go wrong, things that probably will go wrong. things that will go right as well. When you think about the book and some of the key messages in the context of this industry, sort of what comes to mind for you. I've been thinking a lot about this as the book has been coming out. I am really worried for this industry, really, really

concerned. And it's not because there aren't great humble or fantastic leaders. Brian Armstrong is a fantastic leader, Jeremy Allaire. There's great leadership in this space. But for the most part, a lot of leaders were born out of the ICO boom. A lot of the employees came aboard and a lot of the executives, that's when they came on. And because of that, they have a skewed view of what will be needed in order to create an organization that will thrive over time. So I'll give you some quick stories of things we've seen. A company nearby us in Boston gets fined by the SEC for illegally offering a security during the ICU boom. They get fine. They do all those things. Two days later, they're in a restaurant near the office

with all their swag on, with all their logos and all the rest, party. I mean, pumped that they made it through. It was like a badge of honor. And I'm like looking at them. I'm like, you guys, this is ridiculous. We're on a visit to a company in a big city, and they've got this 40th floor office space overlooks the mountains. And I'm talking to the 30-something bearded, tattooed, straw hat wearing, hipster guy who's

been there five years, was a bartender. I was there. And he says to me, they raised a couple hundred million in ICO. We've been lean. We've kept 70 employees. We haven't really figured out the business yet, but that's cool. And then I said, okay, I said, tell me about the founders. He said, oh, they're not here anymore. They got in a fight. They're not here. And I said, oh, all right, well, who's the CEO? And he literally, he like looked off almost like he was talking to the mountains. It's not even to me. And he said, CEO, we haven't had one of those in like a year. That's crazy. Crazy. Okay. We deal with a lot of exchanges. We were just dealing with an Asian exchange, an exchange out of Asia. And they basically said, hey, look, we really

want what you do. Our token isn't quite ready yet. Tell you what, why don't we create three or four press releases about us working together and release them? That'll be amazing. And then when the token is really ready, we'll do the work. Okay. So I'm like, no, no, that's like fake Advert, that doesn't, what are you talking about? But the perception is we're going to make ourselves look important. And that's justification for leading company to an outcome. That is scary stuff. Everything you're talking about right now, I obviously agree with. I mean, there's this big wave of non-dilutive capital raising going on, this ICO phenomenon. Almost all of these things look like unregistered securities offerings. So I guess what you're saying is that there's still

kind of an overhang here in this market that we haven't really washed out that crop of folks. I mean, obviously the SEC's made some interventions here, but there's still a lot going on. Yeah. And what lesson are they learning? They've got a lot of money in the bank. The technology is maybe launched, maybe not. Just working with complex technology feels like validation. They've got some proof of whatever they've created that seems really cool, and that feels like they've made it. And the real problem is there's capital in their pockets. And there's no lesson yet. But the lesson will come. Look, there's nothing that will survive without customers and revenue. And so over time, things will launch.

And I remember the, I think it was the guy from Cosmos telling, I think it was a consensus this year. He was telling Pocodot. I can't remember who. He was telling some others going, hey, it'll get really hard when you launch. Like, you think it's hard now. Wait till you launch. And like, yeah, you got to main that.

That's awesome. Try figuring out customers. Try figuring out how to like turn this into something. And you've got all these people like, no, but we're going to launch technology. Great. Build a business. And so that's not a knock on them. The knock is, it's not like I'm trying to build my tech and launch it. That's the right move. The part that's scary is that they're not saying, wait a second, I might not have the answer. And I'm going to have to sit way back and build. It's going to be hard. I'm going to have to attract customers. And to do that, I'm going to have to change how I work with my organization. I'm not going to do press before reality. I'm not going to teach my people that. We're in one meeting where a senior exec literally said to the woman who had brought us in, the work you do doesn't matter for this organization. You're building daps on our platform.

Nobody cares. Here's what's important. And I'm looking and I'm going, it's that behavior on your journey to trying to figure something out that's going to crush the people around you. And part of that is because you got too much money too early. And part of it is because the pain of the market hasn't hit you yet. we got to stop this. We need people to show up and act like adults. When's that can happen? I'm sure in your history of being an entrepreneur, you've seen a lot of these cycles where companies

are able to access cheap capital and raise a lot of money early. And my guess is that there's not a ton of success stories around companies that raised a lot of money early before they had product market fit. I mean, is there any way out of this or is this sort of going to just end badly for a bunch of these protocols? Well, there is a way out. I think there's three categories. There's a category of protocols who are building and launching, who already are designed to understand that they're going to have to stretch really hard to make this work. And I think of Stello, I think of NIR, I think of flow. They're thinking like businesses. They're really, really going to achieve something here.

The second category are those who are maybe in the same bucket as them, but they're flogging the fake. They're PRing their way to do an outcome. And that emperor will have no close eventually on that without people building on your platform. What's going to happen? The third category is the really dangerous one. There's enough money where they can survive. We literally have, since we see into these chains, we'll look into the chain and be like, this isn't even secure or immutable or even like operating.

And you're going to market with buyer token. It's about price lift and all this. Like that's going to get really messy. I predict in the next two or three years, a lot of that will wash. out. It'll be ugly and it'll be painful for many of those people. They'll probably learn a lesson and hopefully come back and build companies from that lesson. But it's going to hurt for a lot of people. I guess a number of these protocols are dealing with almost a three-front war, I guess, is how I would describe it. You have to build the technology as one front. So they need to build it

so that it actually works. A second front is that these things have a native token in them and they're ostensibly going to be worth something at the protocol layer. So how does value accrue to the protocol itself as opposed to companies, or in addition to companies, maybe? And then I guess the third one would be regulatory. Just how do you thread the needle here and make sure that you can be treated like Bitcoin and Ethereum in the sense of not being a security? So, I mean, that's a lot. And I'm sure there are other things that they're wrestling with around just employees and the typical things of running a company. Are there any best practices that you're seeing in terms of teams that are doing better than others in terms of those fronts? I think there are those who have done

really strong work to create clarity around their token in a legal environment that has tried to express what should and shouldn't happen. So block stack registered as a security. I mean, that was smart move. You have others that have done really good work to clarify the distinction between their foundation and their business. You'd be surprised or maybe not how many are like, yeah, over here's my money printing machine. No, that's not really how it's designed. What's designed, your foundation operates as its own entity and it has nothing to do with the technology or building if you're really separating those. I see some works have really constructed that effectively. This is really hard stuff. I mean, there's no playbook for it. And so maybe the humble leader,

let's go, the humble leader says there's no playbook, but there's a right thing to do here. There's a law. And there's a way to teach my employees that this isn't some piggy bank. We rob. And the ones that are struggling are the ones who are like, look, since there's no law, I'm going to sort of like flouted as long as I can and stay ahead of the regulation. That's going to come to roost at some point. So your company is building a business intelligence suite that sits on top of these chains and deeply understands what's happening and surfaces insights in terms of how people are actually using the chain.

What are you seeing in terms of just actual customer adoption on some of these platforms? I mean, are there categories that you see are breaking out or getting more attention? There's some obvious answers. Defi and stable coins are breaking out, no question. It's funny. We are seeing, if you asked that question a year ago, there's a lot of like intent at breakout applications, but it's not really justified yet. We're actually seeing a few that have massive real activities happening.

And we released a report today. This is probably going to bum a whole bunch of people out. But we released a report today about Tron. With data showing activity, they're one of the most active true participant chains out there. How they got there, whatever. But there's real DAPs doing real stuff on it. I think algorithms getting real traction, flows launching with real partners like the NBA and Warner Music, et cetera. Cello's got amazing partners, Mercy Corps, folks like that.

You're starting to see some real behaviors. That's going to pay dividends. You guys recently wrote a good piece on the gaming industry and how online games are really ticking off. What are you seeing there? The piece sort of exposed the amount of money that the gaming companies were likely making by selling their virtual goods, their kitties and their gods unchained, et cetera. And then importantly, how much the players were making. The whole arc of those companies are reselling of these goods.

And so it was less about who's doing well, who isn't. but there's like real revenue pumping through both for the organization and the player. And now that you're starting to be able to see that through tracking of what the wallets are doing and where they're going and that's a space that's growing quite well. You're seeing CryptoKitties had it think an early error that's moving over to the dapper system or the team that behind it is moved into the dapper system. The gods and chains has done quite well. I mean, I think that's such a growing market.

If you just look at that from a market size and then you look at the types of people that are engaging, in these systems versus the types of people that are knowledgeable about cryptocurrency, there's a big overlap there. So not surprising maybe to see that breaking out. So for the games, it's absolutely not surprising seeing some interesting trends like CryptoKitties, 27 million in revenue in their first year with $7 million going to the company and $20 million to the readers themselves. That's a real business growing incredibly well. God's Unchained, made $4.2 million in its first year.

My Crypto Heroes, 1.5 million in its first year. These are really positive trends you're seeing for those who are distributing social tools and gifts and virtual goods through gaming platforms. You mentioned earlier stablecoins taking off, and we're starting to call those crypto dollars, by the way. Starting to start a new thing. Is that your terminology? Should I only use that now? Nick has been really pushing it. So I think we're going to try to go to crypto dollars. Okay, what? Tell me why. It just sounds a little bit more inviting. It's sort of like a play on Eurodollar, which is already a thing. And these things really have a lot of similarities to Euro dollars in the sense that they're accessed to the U.S. dollar, but in a different context.

My motto is do whatever Nick does. Yeah, so just crypto dollars. Crypto dollars. Okay. So what I would argue with stable coins, crypto dollars, whatever you want to call them, this is really becoming the killer app for blockchains in the sense that you have the ability to move around a stable asset, a stable unit of account. And so I'm looking at, looking at this and I'm saying the obvious first use case is just moving money around. There's going to be people that want access to the U.S. banking system that otherwise couldn't have it. So you have these stories about people in Argentina and Venezuela, being able to hold dollars on a smartphone for the first time. That's super powerful. So you kind of work your way through some of those use cases and then

you start to look at the utility tokens and what these things are trying to be and they're trying to do really cool things, distributed file storage, distributed compute. All of these things, should and could exist in the context of a public blockchain. But I look at them and I wonder if there's a way to do some of these things without having another token that fluctuates wildly, if you could do some of these things with crypto dollars, I mean, why wouldn't you just do it that way? I think the answer is you should and you would. Those organizations probably are still fighting for a value to their own token because of how they've been set up. But if you play out where things go if crypto dollars continue to win. It's an obvious sort of the right use case for the

idea of cryptocurrency. Yeah, the right companies will probably start using those as their foundation for creating their utility that will work. You want to talk about humility and confidence. That's going to take a bit of real leadership to give up on my coin that I created that, wait, maybe the coin isn't the thing. Maybe for me it's the utility function. And let me lean into the other asset that will make this happen. So you bring up Tron, and that's an interesting example where you look at the Tron blockchain is actually getting a lot of adoption with Tether. I mean, Tether is being issued on top of that. Does that do anything for the value of Tron? I mean, I guess you could probably argue that, but I'd say maybe not. Yeah, so we've been analyzing quite a bit Tron's

tether's movement on Ethereum, and it's minting going to Ethereum. It's now minting heavily on Tron. You can actually, if you go to our data cooperative, there's a little plug for you, the data cooperative on our website. You can actually see Tet the movement of assets for tether. And it's significant in how much is being used on the Tron platform. And yeah, you could see in the end, will TRX exist or will it end up being really it's tether that's operating and all those utilities and the depths that are thriving within their ecosystem, really just use that tether asset as their tool.

I would love to see that. I think it would actually centralize this space to have all of the, the leadership, not fight over whose coin wins, but unite behind two or three that are really logical instruments. I'll give you an example. Many of our clients are asking us if they can pay us in the digital dollar, in the stable coin. And we're happy to do that. That's fine. That's logic. And we're reflecting the other day. We're finally eating our own dog food here. The companies themselves are using the stable coin to pay us. We're accepting it. This is really working. you're probably right. The next step is the utility folks go, well, maybe our crypto isn't the answer.

Let's just use what everyone's using for their payment infrastructure. Yeah, I think that's right. I mean, you are starting to see some of that functionality get built out just around being able to accept these type of payments. I think what circles doing is really a big deal in that regard. Huge. It'll be interesting to see how this plays out. Maybe shifting gears a little bit and talking about leadership within our industry from a different vantage point, you strike me as someone that's been really effective at raising capital over the years. You had a pretty easy time getting it from us, as I recall. So I don't know if that's your... I turned you upside down and shook you and there was money that fell out of your pockets. I loved it. It was great. Yeah. It wasn't that easy. Exactly. We're happy investors.

But you've raised traditional venture rounds before crypto existed from big name firms, the general catalysts of the world, et cetera, et cetera. What's it like to raise capital right now in this industry? and then talk a little bit about the leadership that you're seeing on the investor side of the fence. I suppose a few things. Capital raising in any time in any industry is always as much an art as it is a science. There is interpersonal dynamics that make people want to invest in companies, certainly strong confidence about what you think you can build and how you can get there. But investors, it's like anything else, momentum carries many investments. If you can get the right lead to come in and sort of circle all the wagons in the right way

and have people feel like they're missing out and all that, fundraisers can happen in any market. That's partly power. Now, the easiest way to do with fundraises to build something that has value and people can see that it's going to have value. Without that, you're probably not going to get too far. But I would say investors, I still see dollars flowing into this space. We see funds like A16Z raising more funds to put into the space.

I think investors are still open to good companies. I think they're asking more difficult questions. We're flipping from a, hey, I'll take a flyer on this thing to, okay, I'm going to really ask you, are you the leader that will know how to navigate a tough market to success? So there's still money to be had out there. I think you're just going to have to go through a slightly different raise process just because everyone's asking harder questions when markets get tough. There's kind of been a bifurcation of dedicated funds versus traditional funds. If you look at this industry, there are a bunch of dedicated funds. Castle Island, we only invest in blockchain infrastructure companies.

So we are in that category. A number of the larger traditional, quote unquote, funds have accessed this market in a slightly different way. Some of them have spun out folks to start those dedicated funds. Some of them have invested in other funds from their fund entities. But a big question, I think when we look at a lot of companies is who's going to be the downstream source of capital here? And if it's not going to be a dedicated sort of crypto fund, then is what you're doing compelling enough such that a traditional, quote unquote, real venture fund that is

writing a traditional 10, 15 million dollar series A check will get it and we'll kind of see the opportunity there. So I think there's a big financing risk to a lot of these businesses. I'm curious how you would think about that. You're answering the question about how this space survives. Now, our main investor, our lead investor, is true ventures, which is not a crypto fund by any stretch, although they believe strongly in crypto and have a number of investments there, but there's not a dedicated crypto arm. It's not a crypto fund. So we do see non-crypto only getting into the space, but I would say the end result is going to be who's building companies that is acquiring customers and driving revenue. And a VC is logical about its

investment strategy. There's the make it up. You need to be doing 150K MRR for you to have product market fit. There's clearer patterns that venture capitalists might follow. It won't matter if you're in crypto or an automotive. It doesn't matter. Are you hitting targets? Are you growing? Are you scaling? Now, the problem will be if the entrepreneurs in this space continue to think PR is going to go get the rest of the capital for them. It won't. Because as soon as the VC, peels back the covers, they're going to go, wait a second, you did some press releases, that's cool. Oh, and you got some traffic from that. That's interesting. Okay, but no one's using your product. The approach of all this is like, I want to like, wake up. Yeah, downstream will

happen, but you're going to have to build today. You're going to have to do the thing that is real customer activating. And I don't think it's that people aren't trying, but it's not that they're saying that is the most paramount thing and I will change how I behave. in order to lead my company away from false marketing or celebrating SEC fines to we are only going to be focused on real metrics that drive companies. From that, investors will follow. Partners will like you more. Employees will want to hang out in your company a lot more. And that is important. Someone just told me this crazy thing. You're selling you the exchanges, just so you know, most reorg every sort of three months or six months or so because a lot of people leave come and go.

And I'm like, why? And then I'm like, I know why because many of it is just predicated on false trumping of their horns. And of course, the reorging, because when half the talent goes out the back door to go try the other exchange, you're going to have to reorg the business to create that. That is the hardest way to build a company ever. So I'd imagine if you wrote this book five years from now, there would be a big chapter on COVID-19 and how it impacted your business and your leadership style. So how's that going? I'll start with 1995 when I first was a remote worker. I started a company and I'm like, I'm going to be remote. And I had this little office in my basement. And I spent probably five hours a day watching Oprah. Truly, I will never forget. Since then, I'm like,

this remote stuff doesn't work. I'll be honest. I didn't really trust employees would be like, I would like to be remote. I'm like, yeah, I'm not going to really buy. into that. You can't possibly be working. You're going to watch TV all day like I did. And I've had remote employees in our firms over the years, but it was very small percent. The market has been sort of slowly moving towards accepting remote practices. You'd have occasional Zoom calls, but more often than not, I would be like, oh, they want a video chat. Just tell them I'm on the road. I don't want to do that. When COVID hit, we're forced into this environment. We set up at home, we zoom all day, we do these things. I mean, I haven't been as this productive in years. You're not distracted. The amount of time

I'd be in the office and just going from ending a meeting to a new meeting, chit-chat, you pick up your papers, you laugh about something, someone's distracting you. That takes 10 minutes. You do that 10 times a day. This is a fantastic moment to accelerate into what is really productive working and changing how we work. I'm really sad about the stuff that's happening in the world, but I'm fantastically thrilled about how it's forced our business and businesses to reassess what's important. Do you think that it'll change the way you manage? Absolutely. It already has. I'm not the most emotive individual in the world. Some might say I lack deep empathy. Sounds like a psychopath. There's sociopath. Don't call me a psychopath.

Or I'm a slight narcissist, whatever. The truth is, it's easier for me to be really constructive and congratulatory via video and certainly via Slack in a way that people are like, dude, you've never said that to me. Or even like, do it this way in a very simple way, if you were my employee, which would be amazing, but you already have a job. But let's say that someday, frankly, I'll be working for you. So maybe we should go the other way. When I'm working for you, I would like the hard part used to be, okay, hey, I'm going to give Matt some feedback. Let me set a 30-minute meeting, I'll bring them in. Well, there's like some awkwardness about it. I'll have to like really have this discussion. That's hard. And there's a lot of barriers to that versus, hey, Matt, the thing you

just produced today crush me. Like, it was amazing. I'm just sitting here thinking about it. You can get more out of that quick tidbit dozens of times to you than sitting you down for 30 minutes and saying, hey, this is really good work. And so it's forced this management style that's much more empathetic, calling out the small moments, not the macro moments. And that's, and that's, already is paying dividends. I'm sorry, but employees are saying, hey, can I go on vacation today? They used to be, I'd be like, I don't know. We work. And now it's like, dude, take all, whatever. We work all the time now. Take whatever time. I don't care. Take the time. I am really in the mindset of if you get your work done. We're all going to see it. If you don't, we're all going to see it.

I don't care if you go to the beach today or not. It doesn't matter. Go do it. It's interesting. It's forced us into this paradigm. I wonder if we'll have less of a stigma around these remote first companies. I mean, used to always hear there's never been a billion dollar exit for a remote company, but I don't know if that's still true, but I'm sure if it is still true, it won't be true for long. It will not. The guy, if people want to learn remote, I just have to call him out. Nick Francis, Help Scout, go look on Help Scout site. I think look up Help Scout remote. You'll see they have all sorts of docs that will teach you how to hire remote and how to embrace culture remote. If you want to know how to do remote work, Nick Francis,

this helps scout. This guy is a genius. He's been doing it for years since past decade. He's pounding the pavement on it. And I keep going, yeah, Nick, that's not me. But I've learned a lot from him. So if you're looking to learn this stuff, he's your guy. So speaking of people that you learn a lot from, in the context of leadership, who right now are your sort of go-to mentors and who do you look to, even if they're not direct mentors? Who do you admire from a leadership perspective? Well, the first is always the same answer for me, which is Chikar Ghosh, who's a professor at HBS. He was a CEO of Open Market. I think he's the co-chair of the Rock Center for entrepreneurial activities at HBS. He's just by far the greatest dispassionate, thoughtful,

observant leader I've ever encountered and continues, even as our businesses have evolved and he's evolved. The reason I think more than anything is there's no, a lot of leaders, it's about their worldview placed into what you're doing. And with, With Shakar, it's always about just the world. It's just this may be how things work and there's not, this is what I would do. He has a line that he always uses, which I love, which is I see things differently. Now, the line that I used to use is, well, that's wrong or this is how it should be done. Think of just the slight, I see things differently. That's just a really powerful. So yeah, I'd call it Shakar. I got to give the guy credit. So one of the things that really struck me in reading the book

is that it was about an entrepreneurial journey, but it was very personal. So there's three stories in there about relationships. So talk a little bit about that and how you see relationships in the context of this leadership story. The idea of the humility imperative is your leadership is really in the eye of the beholder. And a lot of your leadership is going to come through what you're saying to your spouse or the advice from your spouse and the impact of your work on your spouse, significant other, et cetera. So there's a story in there. about my divorced. And I would largely say Buzz Agent, or my attention to Buzz Agent, killed my marriage. I was a disappointing husband, to say the least. And so there's an article in there about that

divorce and building that business what caused it. There's an article in there about almost losing my current wife due to some food issues and other stuff. You got to read it, I suppose. It's Brussels Sprouts, that's the name of the story. Look, the reality is I want people to remember and realize that this isn't about I show up at work and I become a leader. This is about your entire life is surrounded by people who are helping you adapt and evolve as a leader. And it is as much your responsibility to treat those in respectful ways as it is to build your company. And if you can balance all of them together, you can succeed. But recognizing the importance of those as you carry your journey is probably as important as anything else you're going to do every day inside your company.

I thought there were really powerful stories. Yeah, you really put yourself out there. Really well done. Thanks. So that's a good place to leave it. Dave, where can people learn more about Flipside, follow your work, and get in touch? Flipsidecrypto.com. That's the place you can see actually some live data about blockchains and crypto organizations. So go there. The Humilityimperative.com. You can read some of the stories there and that'll lead you to the book. It comes out June 30th. It's on Kindle and Paperback and Hardcover, all the fun stuff.

If you go to Amazon, I think the week of June 30th, you can get the Kindle copy for 99 cents for that week. So cheaper than a cup of coffee, maybe. Well, it's a good book. I recommend it. Thanks for coming on the podcast and talking about it. Thanks, Matt. Always a treat. Thanks for listening to another episode of On the Brink with Castle Island.

To find out more about Castle Island, visit castle island.vc. To listen to all of our podcast episodes, please go to on the brink dashpodcast.com or just click on the tab in our website. Thanks for listening.