Entrepreneurial Minds introduces its next journey in Costa Rica with its fifth episode, where we speak with Donald DeSantis, who is an entrepreneur, mentor, and an author. He shares with us the common mistakes that come with building a team and also digs into thinking about company culture and values. Join us for conversations about choosing your journey, mental health, and sharing stories from around the world.
Entrepreneurial Minds introduces its next journey in Costa Rica with its fifth episode, where we speak with Donald DeSantis, who is an entrepreneur, mentor, and an author. He shares with us the common mistakes that come with building a team and also digs into thinking about company culture and values. Join us for conversations about choosing your journey, mental health, and sharing stories from around the world.
spk_0: 0:03
welcome to entrepreneurial mines. I'm Valerie Donahue and on this podcast will travel around the world to learn everything that we can about individuals which used to greet businesses from scratch. We'll dive into what drives them. What stops them and wouldn't buy or sell in order to identify are their common factors that unite us as entrepreneurs across continents. Here's your next episode. I'm hearing a sorry Costa Rica with Donald is Santis. Donald is a Brooklynite, and it's real serendipity for us to meet here in this remote town. Donald is a serial entrepreneur tech mentor, and his latest endeavor is writing a book. He's the co founder of E. T s, a real estate technology company, which Crane's New York named best places to work in 2015. He's an expert in building high performance Team's on. It's such a treat for me to be able to pick your brain today. Um, Donald, you've transitioned from so many different things in your career. You were doing product development on, and now you're writing a book about team building, obviously co founders and entrepreneurs where a lot of different hats, what drew you to the to the human capital aspect of building a start up for your
spk_1: 1:26
book. Yeah. Good question. The human, the human capital aspect. Um, you know, I think is I was reflecting, So I I left BTS a couple of years ago. I'm still really close with everybody there. I love the team. I try to go back and visit when I'm in the city on when they have events. And there's free food and beer. I'm unemployed right now so you can get new three slices of pizza. Um, but, you know, when I reflected on my time at VTS, there were lots. You know, there are lots of highs and lows, of course. But when I thought about the highs, one of the biggest, you know, one of kind of like the biggest area is just thematically was all around people and creating a, um, a great place for people that kind of work and dedicate their efforts in time. We asked people to show up here, you know, five days a week for 10 hours a day, sometimes longer, you know, and and to create a space where people, you know believe in what they're doing, They believe in the vision of the company, the competence of the executive team to actually execute on that vision, and they're feeling really challenged but also supported. That's just one of those. I think it's one of the coolest gifts that you can that you can kind of provide the cool since you could. D'oh!
spk_0: 2:43
Sure. So one question. When it comes for two young startups, young companies When should they start thinking about building their company
spk_1: 2:54
culture? Um, it's good. It's a good question. I think I'll take. I'll take kind of like two shots at answering that. So I am as part of kind of doing research for this book. I've been speaking with a lot of people who who I look up to and a friend of mine. His name's James, and he started a company called Fire Based. Actually grew the company. It was developer Tools sold the company to Google. They had this great outcome. But ask James James, when did you start thinking about company culture within your co founder and he? Actually, it was almost a year before they had made their first hire. They had written out, you know, their values and their mission and kind of what kind of company it was gonna be. So, you know, on one hand, like maybe nine months to a year before I don't I don't think that's crazy. But you know what I really think about, um, when everything about kind of like the cultural values that I tried to instill in the company, I think that's where those really came from. I mean, they came from kind of like my own, forming his own formative experiences as an employee, and I've had great experiences as an employee, and I had some really, really bad ones, but a lot of it, you know, a lot of it is just kind of like pulling from our own history. And, you know, I had the opportunity to work for great leaders who who who are able to create great spaces for us, you know? I mean, it's meant start a decade before, you know, you actually end up starting your uncle. Just It's funny how these things kind of carry with you in ways you don't necessarily like, plan for or really sort of design. But then but then you start. Oh, here it is. Actually, have this thing has been important for almost a decade because I recognize what being on the other side of that, you know, like something like just transparency or just like a culture of accountability or ownership. Ownership from the executive team. You know, uh, that yeah, that's it could start a concert a long, long time before
spk_0: 4:57
so four companies and as you mentioned, sometimes start ups. They're just like they're running at 1000 miles an hour. And this just seems to be something that falls off, and you don't start thinking about it until later. What would you say to entrepreneurs that are just in the beginning of launching their business? If if they're thinking I really don't have time to think about company culture, what are the What is the thing that they really must do? At the very least,
spk_1: 5:26
yeah. I mean, you're you're kind of you're building, You know, you're kind of always building a culture in one way or another. So you just I think the thing is like building culture isn't isn't something people actually put off. We talk about this like oh, you know, should be put off building culture. Can you? How can you afford to put off building culture was actually no such thing as putting off building culture. You're either you're always doing it. So you're just doing it intentionally where you're doing it unintentionally and everything unintentionally. The culture that you're building is one that reflects on what does that actually communicate? And it might communicate the kind of idea that culture isn't culture quote unquote amusing, like air quotes here with people about like, you know, culture isn't something important at this place. Values like what we kind of value isn't actually important here. This is a place where we show up, we get a paycheck, we leave everyone. So we work really, really hard. And then, yeah, maybe have a happy aren't everybody kind of gets drunk, but like that's that's what this place is and about like, um so you don't like That's kind of like building culture bye. You know, default rather than intentionally and in general, deeper in any of that. But like in general, like, that's not gonna leave very good outcome, because when things like when things are going well, you can kind of get by on that. And things were kind of mostly work, but things aren't gonna go well. Um, And when things start to unravel, if you don't have, um if you don't have, like, a really strong cultural foundation and if you don't have really strong values and sort of like a shared sense of purpose, a shared sense of operating, um, like that all of the hard things are gonna be much, much harder than they otherwise would be.
spk_0: 7:21
I really love that. And I think that it's It's such an important thing to point out because again young entrepreneurs orange entrepreneurs in the beginning of their journey, they might see it in this way is that it's something they're putting off. But it's actually something that they like. They're just building. And like you said, it's it's going to happen one way or another, it's by default. So there is also I think it's Ah eh, These are cautionary words, right? Just to think about. If either way, your actions are going to have an impact on your organization, they might as well have the impact that you intended, Thio. So I think that was a really interesting way of putting it. What would you say are the most common mistakes that founders make when it comes Thio trying to build a high performing team.
spk_1: 8:08
Yeah, um, I mean, I'm I think first of all, I'm just sort of sympathetic Thio. The situation that founders are in right now, especially the technology space, is universally true, but especially in the technology space when what you're trying to hire software engineers were great designers, a great product. Managers like it's a It's kind of a tight market, you know, people with experience. I think there's a lot of folks in and it's a good thing. There's a lot of folks entering the market right now, sort of more the entry level dude like boot camp and stuff like that. You know, people with 3 to 6 years or more of experience, like it's a it's much, much more competitive. So, um, so I understand kind of, you know how and why people put this stuff off or they look for kind of look for kind of hacks, but probably the number the number one mistake that I see companies make when it comes to building culture is just kind of copying. It's following best practices and you know it's like what's wrong with best practices, like best practices, you're good, you should fall best practices. But it actually looked like, you know, what are one of the best practices today in terms of like culture and recruiting an HR, like usually it's, Yeah, it's kind of like the sort of, like the latest fads and opinions that are coming from HR consultants and, like the press and people who are sort of like, paid to be pundits all of this stuff and where they're going to look for all that, like where they're going to look for all of that is just like, what is the kind of like latest, you know, start up the juror like, which is which is the cool kind of interesting company today. And so they just like Okay, cool. I mean, if you rewind, I know you have to go back. I have to go back a little ways for you on Facebook was considered a cool, interesting company. Now they're kind of everybody's punching bag for better or somewhere they deserved or not deserved. Right? Is there a lot of ways? But yeah, let's go back to like 2011 2012 when, like, Facebook was like the hot shit. It's like, Okay, well, what? It you know, if we think Facebook is great, you know, the press and consultants HR hundreds, they go. Okay, cool. Let's look at all of, like, the the cultural Touchstones like, Oh, they've got these bigger feeding euros and oh, they've got, you know, the culture of, like, move fast and break things. And it's like, Oh, they've got It's like whatever the hell it is, that sort of like from the outside looking in and people just trying to copy that and try to copy it like whole hog and they expect, like, Okay, cool. If we copy, It's almost like if someone has a great, uh, you know, fashionable clothing is like Okay, like in high school Was like, OK, yeah, you wanna be cool. I'm going to call, gets addressing the cool kids and you go by all the clothes and then you just show up like shit. I'm still not cool, like I don't understand what happened. Companies do the exact same thing, and it's and I I understand, especially for first time found, because he doesn't know any better. And there and even their veces their investors will be like, Well, you know what we're really saying. You know, they have somebody who works at the VC firm and have all these recommendations on what it is that you're supposed to be doing based on the latest trends. And you can't copy your way to great culture. You can't copy your way to having something like interesting and meaningful and different, like like the way the way that you create that for your own organization is I mean, the sounds like it sounds like a Hallmark card. That's really true is you have to embrace what is like what is like, authentic and different about your organization, which oftentimes in the early days is a reflection of founders, right? So and it's it's hard to do because it takes people get self conscious and you might have to evaluate kind of yourself in a way that you might not necessarily be comfortable with. But like every life like if you because you're starting a company like you, value something you know beyond, of course, like okay, I want to be successful entrepreneur, which everybody has a little bit of that. But It's like maybe there are certain ways that, like you really believe in terms like how you work, right? So we're, like, very design driven or were very like engineering driven also perfectly fine. You know, we're very flat, like no manager is very little higher Buffer was a company that, like, played around in that space. Or you could say command and control like we are like we're hierarchical. And that's like, these things aren't necessarily good or bad. We're just different, and they're gonna be more or less successful in different contexts. But But the mistake that people make is trying to copy whatever like the latest thing is, you know, versus going actually like, legitimately honestly, who are we and and having kind of like the courage to embrace that toe own it, to telegraph it to your employees, to the market, even to your customers. And like, when you do when you do that, like that's gonna lead to like a strong, durable, authentic culture that's gonna attract the type of people who are actually gonna, you know, show up and be able to kind of like, row together, you
spk_0: 13:06
know, um, so if there are really, If there are entrepreneurs that are listening again later in the early stages and this is something that just brings them immense dread, they don't know where to start. What would you say to ease their mind? And what kind of a time commitment is it? Is it something that you know, two For them to be able to know that it's something that they can do it The onset?
spk_1: 13:30
Yeah. I mean, it's one of these things where it's gonna be a little bit, uh, like, I don't necessarily think you can just like, you know, go into an afternoon workshop and figure out what these things are like. There's it's a little bit of, of, of, kind of finding out, you know, discovered, like thinking about like Okay, what's important to me in terms of like how this company operates with this company's about, But, you know, you probably have co founders of well, too. So where did these things kind of meet? And where do we have a lineman as co founders in terms of what is actually important to us? What were our values? Overlap? And I kind of like the way that I talked about this. A lot of times it's like obsessions like, What is it that you're because it's like values coming values? Sounds like it's like it zapping, put on a wall. And that's how we're talking about here. Like we're talking about something that, like you, you will truly you know, like you're willing to step in front of a train for, You know, it's like we will not be a company that, um, you know, that's that. That's, uh, we're we're a company that, you know, involves our customers in our design and product about the process. Like this was kind of truth my last company, for instance, and we're not just going to go into a room and, like, do are kind of like Steve Jobs thing of like, It isn't exactly how they work, but this is like this stereotype, you know, like we just like we're going to go into a dark room and we know it's best for our customers. So we're like, you know, and I was like, Look, I don't want to build a company like I am obsessed with, like doing a customer centric, design driven product development process and thankfully, Mike cofounders agreed with that. But like that wasn't like a value isn't something was important to us. It was an obsession. Like we obsessed over it. We talked about it constantly. We spent time and money on it. Not because it was like, you know, we're trying to, like, be calculated about, like, what is the right thing for the company and like and like, what kind of culture right about it was like a sincere reflection of an obsession that was our own and that was shared. And then as we talked about that telegraph that that ended up attracting people who liked that message and like shit, I've wanted to work in a place that really valued this in the way that you are obsessed with it. Basically. And there are other people who are kind of like, Yeah, that's I That's not kind of my bag, you know, And and I don't really three designers, for instance. You're like, you know what? Actually, I think a lot of designers I've had I've hired a shift on the designers. They don't like talking to customers, like a lot of them really just want open, sketchy photo shop and go nuts on, like having the coolest, sexiest, like design interface and, like dual animations, the buttons and also the crap. That's perfectly fine, right? There's like a place for that. But like that wasn't less. And I met people like bouncing. There's not gonna be happy here, you know, this is a place where your level of it in terms like a different type of design of the mark, customer centric and its spectrum. And we did value like great design, a great your face. But that was just like it was. Like I said, You know, we're concerned with the cake. Um, so again, it's It's It's like that was a thing that we had some self awareness. So we know we knew that this was important to us, but I think that, like every week, every person like, if you really think about like, what do I get worked up about? Like, when was last time I got in a fight like an argument was last time I got an argument, whether it's on the Internet or with a co worker like and this could be around process specifically like Howard buildings not like you were so your background as a software engineer. When was the last time you got, like, an argument in terms of like with another co worker, Like shouting in a conference room about how you were supposed to build something? You know, um and you have the engineering injuring process itself was being run or whether it was like, specific design engineering, like like software design concerns and how it was being architected like people have strong opinions on these things, right? When was last thing that I got a beer with some friends and they got You're talking about something kind of work It's related or how you work that you just kind of wouldn't shut up about, You know, like, these are these are the plate, like, these kind of point at I'm not saying they're exactly what you're obsessed are. But these point at what you're obsessed that about, and if you kind of step back, Oh, shit. Actually turns out like these things are like, really important to me, and I do have strong opinions here. I would just say, like, embrace those things because that's what's gonna make you different and unique and weird, like in a good way.
spk_0: 17:56
Yeah, and it also bring down conflict, right, Because if you're in alignment edited total, it'll help you hiring. And it'll help you in terms of the people that are within your organization. Are are aligned in terms of in terms of something, right that that there's something outside of like you said, like just getting a paycheck that unify summons and being there. Um, so once you come up with with your values, how do you communicate that to your existing team and when you're doing the hiring?
spk_1: 18:28
Yeah, um, that's a good question, I think, in terms of, I'll start with like, I'll start with communicating them to your team. I mean, obviously you can you can write them down. You can put them in an on board on deck for your employees and talk about them in your company on hands and remind people out there like and all those things you you should d'oh. But that's not That's not really how these things kind of get betted in. Um, I think like like people like like an organization values what it rewards, basically, and so you know, when it comes to how do you communicate your values. It's like, Well, what are the behaviors that you are rewarding, rewarding your employees for in a way that's like public? You know, there's the kind of old trope like Preysing public criticized in private. So to the extent, like when you think about like, what are you praising in public? You know, be thoughtful about that, like Okay, cool. Like if these air, The thing is that, like, if these are obsessions and kind of falling out of those, like here's some values in terms like what we're gonna come up with and call our values everyone has this mental model for company does. That's perfectly finally write these things down in the form of values. How, um, like I mean, we, you know, we would have, you know, every every quarter every month. We were constantly on the lookout for people who were emulating our values, and we would praise, and it could just be, like, informally and good people like you. This was, like, really awesome thing you did, or sometimes, you know, at like, monthly all hands to do it. We would kind of this weed like recognize people in front of the whole company and I think even quarterly we do this thing. Where were the rest of the like employees with nominate other employees for like living up to something like we didnt event in this if we just borrowed it. But like you just like simple stuff, you just have to do it and sometimes it sounds cheesy, and it might be better ways to do it, too. But like what? I what I can say there is, like the like, the Maur You just like praise people and reinforce like, bring these values toe life through like, you know, like And then, like Jane did this specific thing, like one of our guys of transparency and like Jane, did this when it came to like this thing interaction of the customer and that, like, really, that was like, not the easiest thing to do. But it was like, the right thing to dio, um, people like, Oh, cool. That's what transparency means. That this guy was that transparency when it's hard, not transparency. When it's easy, you know and like and people start thio, it gives them permission to kind of act that way on their own. And when they run into, like, some situation. They're like, Okay, cool. Like, this is this is what we value. This is what it looks like. And therefore, this is kind of how I'm gonna act. And then on the flip side, of course, is like when somebody doesn't like, Not that, then, you know, just take them to have a conversation. But of course, like, don't do that privately.
spk_0: 21:27
I just wanted to, um, change topics just a little bit and learn more about your writing. Um, So, your first time author, What are the challenges that you're finding and writing? Your first book?
spk_1: 21:41
Yeah. I mean, where do you want to start? There's a There's a lot
spk_0: 21:44
of your choice.
spk_1: 21:45
My choice. Okay. Um, so I think, um I mean, like, the first thing is is like, I've never I've never written a book before. So I had one kind of misconception, which was which was okay. Cool. I'm gonna go off into the woods. Very, you know, solitude and, like, be really productive. Sounds like a good idea. Think of, like, throw and Waldon or whatever. This kind of romantic idea that so did that in a friend of mine owns a Buffalo ranch in the Canadian Rockies, and I spent some time up there before, so I went, and this is actually seem like March of this year spent, like, a month or so up there, and it's beautiful and it's lovely, and I thank him for letting you stay there, but, um, I realized, like, writing is a very solitary process, you know? Um, and I spent about the 1st 2 weeks really productive. But then, like my productivity started the fall, and I thought it was because I was being unfocused on discipline or whatever on guy spent. The next two weeks was kind of like grinding. It was just super hard and and what I eventually would eventually realized Waas that's actually being around other people, is like, really important. It re energizes meaning, and it re calibrates me in a way on def. I am not around people for enough time. Um, I you know, I just like I kind of like I get depleted, you know? Um and so I think so. Part of this is sort of just been like some misconceptions in terms of like the process, it turns out like the best situation for me is actually, uh, probably like being in Brooklyn in my apartment is just like a routine structured routine. I have got the bodega down the street with, like all the food that I need. I've got Thai place that I can order from seamless. I've got, like, my desk, which looks out the window and like everything is just like right there, actually having that routine. And then if I need to see friends just like Tex somebody and it's like Merrick City seeking out pretty much any night of the week, you know? So counterintuitively actually going nowhere is probably actually the best set up for me in terms introvert. And there's a lot of things. But that's just one example a long time to really kind of understand
spk_0: 24:02
and what has been the most. What has been the most surprising thing that you learn so far through this process?
spk_1: 24:12
Um, through the writing process, The most surprising thing? Um, that's a that's a good question. I think the thing that I've probably been most surprised by Waas you know, I thought that I wasn't like reading a book is like kind of too distinct phases. There's like reading the manuscript, which is just kind of like getting it's it's It's like it's just getting all the raw material together. And then there's like editing the manuscript, which is kind of like taking all that stuff. It's kind of a lump of clay, like taking that lump of clay and turning it into a pot, you know? But getting the manuscript done is is pretty is pretty difficult because a lot of time I made my goal was 40,000 words, which is about 200 pages and then edit it down. I'm like, Okay, we edited out about, like, 30,000 words, maybe 150 pages. 25,000. But you just assume they're gonna be taking a lot of it away as you get that at any process. Uh, getting getting to 40,000 just some days was, like, so incredibly slow. And it wasn't. And I thought that I wasn't like self editing as I was writing, but I kind of had this epiphany one day where a lot of times in the morning I'll wake up and I just you have free right? Mr. Journal, I was told, was fear and and a journal. And all of a sudden I look up in like, half an hour's gone by. I've written, like 1000 words or more in a free right. And then I tried to, like, start writing of this book, which I have a lot to say about, Uh and it's been hours and I would and I don't get like, 200 words out. And I was like, God, this is like, you know, it's like squeezing water from a stone. And it wasn't until one of those after one of those rewrites when morning was like I was like, Oh, my God, like I I need to approach this manuscript almost like but just with the same mindset that I'm bringing to the free ride and if I can do and I was like, I just try to do that It was like, actually like, think after I click yourself into like the right head space. But when I started thinking about it like the free right then it just came so much easier for me. It just it just flowed and it was a small thing, like a lycan, but it was it was it was. The stick of very is like the subtle shift in terms of like the mental. And the mental framing is like more than just like the mental framing that brought to like sitting down already. So that was one of the biggest things that, just, like, surprised me like struggling, struggling, struggling, struggling, struggling slightly reframe. What isn't going to dio, and it's like kind of blocked everything.
spk_0: 26:51
So do you feel like it's getting easier now? Do you see the light of the end
spk_1: 26:54
of it? So now it's so I so that so that reframing, hoping to get the manuscript on? Um, and I'm editing, I have no idea. It's like I am struggling right now, and by the time I'm done editing, I'm sure I'll have some other like inside or like, thing that helps me. I have some light bulb moment that makes everything much easier, but I have not had that yet, So now it's, it's brutal, and I'm editing us. I'm trying to turn the lump of clay into a pot and um,
spk_0: 27:21
suggests every center you then, in terms of what, what is going to be the biggest takeaway for readers once you're done and this is live.
spk_1: 27:32
Yeah. Yeah, totally. Um, that's that's a good question. So I think like the big the big things, of course, are like, you know, if you're not already aware, it's not manure like hiring is the hardest thing in the tech business. And what it might not always be the case. It's probably always gonna be top three and hiring. It's hard because we're trying to optimize for three things, and getting all three of those is actually really, really difficult to dio. Most companies end up settling for one of those to which leads them to thrash about and actually usually make exacerbate. Those problems makes it work. Make it worse. But most companies trying to do to solve that problem is copy what other companies are doing. But that doesn't actually work. Then they just end up with, like all of these, like weird trapping is of, like other companies, cultures and their art if, like other company artifacts and cultural norms that don't really actually represent them at all. But the companies that are able to attract talent like consistently and tell it that lance their values are companies that do something completely different, which is instead of trying to be like other companies, they actually take a look inward and say, Like, Who are we? And like, what are we authentically sincerely obsessed about? And they embrace those obsessions and the telegraph then thio their existing employees. They telegraphed him to the market and obsessions air. There's like three traits are aspirational. So they're about something bigger than the company itself in this, you know, the company mission might be that. But also just be how we were like, how we work is actually more important than, like, is this gonna be a good business? You know, 37 signals may be an example of this. You make base camp. They would rather they would rather blow up that business than work like a normal company, Like a no meetings company. I'll tell her stuff, right? So it's aspirational spirit in the company itself. Its directive. So it tells you how it is that you know, this obsession points that like how we actually act on dhe. Frankly, three things. It's polarizing, you know, like not everybody is going to be into it. And the more you dial it up, the more you polarize the market. So a lot of people are gonna be kind of pushed away from just perfectly fine, not closing like we're going to be jerks. But it's like they're like, No, that's not my bag at all. But other people are gonna be ridiculously attracted to it. And those people that you want, because they're going to stick with you when things get really hard and they're gonna be lined in terms of like how it is that we actually work through hard things together. And so we actually do that. You sort of invert this whole thing where you end up creating a bunch of value for yourself. As a company, we become much more values driven as a result of embrace its obsessions. You're differentiated in the market, and instead of having to go out and, like, beg people to join your company, people actually are coming to you and saying, Hey, like you guys like I'm picking up what you're thrown down and like, Are you hiring?
spk_0: 30:16
Um, when can we get our hands on this?
spk_1: 30:19
Um so my target shift. It is like mid February right now, so it's coming up. Pretty soon I've got, like, writing. I've got like, I've got to turn this editor damn script in about a month and yeah, so yeah, I think it'll be Q on its February is the target. But I'm very dead, like I'm a very deadline motivated person. So I think I think I think it'll it'll happen. But you wanted the outside.
spk_0: 30:47
Donna, Thank you so much. It was so interesting to learn from you. Uh, can't we thio for your book to launch and to read it and, you know, wishing you the best of luck in the in the rest of this journey. Thank you so much.