#019: Zack Holland - How to Turn Failures Into $100M Startups

Good luck being a founder just because there is no path. There isn't. Even if you study at the best MBA in the world, you're going to graduate and you're going to learn as soon as you try to start a company that there is no playbook, there is no life without ridiculous curveballs. And the only way to learn is actually doing it. Like there's only one real MBA to be a founder. It's just being a founder.

Zach Holland is the founder and CEO of Select Few, a platform that brings transparency, accountability, and performance to marketing by leveraging AI and data. To date, Select Few has helped over 200 customers ranging from venture-backed startups to large enterprises. In this episode, we cover Zach's serial entrepreneurship journey, launching and scaling multiple million-dollar businesses, and how he uses failure to his advantage for company building. Today we have Zach Holland from Select Few joining us. Thanks for joining today, Zach.

Absolutely happy to be here, man.

So I'm really excited about this episode because my friend Ben, who had introduced me to Zach, had said to me, he's got one of the most interesting stories that I've heard. And I think like we've had a a wide array of guests that have come on here. And I, I was doing a little bit of digging on your, your story back from a young age, and I'm very excited to jump into it. So I think like it's probably most appropriate to just start with you from a young age of like where you started and where you are now, even just from where you were living.

Yeah, of course. So yeah, I had a little bit of a different upbringing. Grew up in a little 200-person village in the Amazon rainforest in Ecuador, a place called La Pastaza, because my, my dad was doing snakebite research and my mom was a social worker, wanted to work for free down there. And so from an early age, things were different, out of the box. There wasn't a Target or a Walmart down the street. And so everything was like a family mission to figure out. And so I think fell in love with solving problems and thinking in a slightly different way from super early.

And right away you were like, all right, I have to build Select View.

Exactly. I was like, Select View is in the line. No, but I mean, even at 7, I had a little import-export business with my cousins in the States who would send things down that Ecuadorian kids couldn't get, like Pokémon cards and things like that. Always like wanted to like start little businesses to solve problems.

Can you take us through post that? Park City, LA, New York. Give us— I know we talked about this before, but give us like the 1-minute version of each.

Yeah, definitely. Uh, 13, moved to a place near Park City, Utah. Lived right on a ski hill, like great, you know, great high school upbringing. Uh, skied 150 times my sophomore year high school. So, uh, you know, got to do that. Uh, moved out to Los Angeles, went to USC, uh, worked in, uh, in LA for about 8, 9 years, and then, uh, moved to Brooklyn, New York about 5 years ago.

Where in Brooklyn are you?

Williamsburg.

Oh, hell yeah. What part?

Uh, South 4th, Bedford. Wow.

I lived on South 4th and Driggs for 2 years.

Nice. Yeah, a block away.

I just moved up to Greenpoint. I'm retiring.

There you go. That is— that's the natural next step. You move from South Williamsburg up to Greenpoint. That's how it goes.

So you started your first business at 7?

Yeah, first business at 7, another one at 9, another one at 11, another one at 13. It's, it's been a affliction for my entire life.

Was it— is it 9 businesses and 2 exits?

Uh, 4 official businesses, uh, 2 exits. But yeah, I think like, uh, I like to say, like a lot of us founders, 4 official, 40 unofficial.

Yeah, yeah, go ahead, go ahead.

No, we're a little out of practice.

Uh, no, I think that that's an interesting point because I think a lot of times entrepreneurs don't actually consider something a business if they don't get it off the ground. Ground, but when you think about like the ideation process of how much time you spend on something— oh yeah, to validate that it's not real, you then just like move on to the next one.

The business note in my phone is definitely constantly filled, you know. But, uh, and then even just like when you're kind of like in between the next major project, you know, there's, there's normally like an approach of let me work on like 2 or 3 things, see which one picks up. And I mean, Select Few wasn't any different. I was actually working on a completely different business when I, uh, when I started Select Few. And Select Few was something I was really doing on the side as a passion, like if I can use actual data to connect two people based on actually getting to know the business that needs something and who I'm going to connect them with, uh, I just found that really rewarding when it actually worked. And so I just started taking a spreadsheet. This kind of group reaches out, this is who I connect them with. And my friends got to know that I, that I did that. And so that list got to like 450 lines long while I was working on a different company. And finally I was like, okay, this is obviously a need that isn't getting addressed in the market. So I switched and started to look for you.

What was the actual inflection point like? Was there a specific occurrence that happened where you're like, all right, this is real, I got to like go all in on this?

Yeah, definitely. I mean, like, so once I was making that decision, it was like pre— like, like right, right. Like in the start of COVID when it was, you know, couldn't leave your house COVID, you know. And so all of a sudden, I think a lot of us who had goals of starting companies that were maybe, you know, so I just exited. I had a little bit of time to think about what I wanted to start next. I think like a lot of us, once you exit your what you want to start next gets kind of almost ridiculous on like the, oh, I'm going to start a space company. I'm going to start a like, you know, some kind of like interesting deep tech. And mine was actually kind of in like a scaled model of like how to get our generation to give back, which doesn't really happen much. You know, millennials test the highest in empathy but give the least amount of their income to good causes. Yeah. And so I wanted to start like an Acorn-style, like pull change out and give it to a— give it to a cause you care about that like gamifies and builds things. Um, it was going to be expensive and like big project to build. COVID hits and you're like, okay, I need to do something that I know at my core I'm good at, I have early customers for, is a big problem. And Select Few had been something that had been in the back of my mind for 10 years.

So, so you, you just made a comment to me about the levels of empathy within millennials, which I thought was interesting. Do you have any sort of insight into how Gen Zs act relative to millennials?

Yeah, absolutely. I think it's, it's less— I mean, they test less empathetic, they test more, more focused on themselves. But the same way, like, I don't think that means that, like, the typical, like, Gen Zs are obsessed with themselves because they grew up in, like, a digital era and everything like that. I think it means that, like, their environment, like, you've, you've kind of had to be from the beginning. Like, we grew up where it was like a balance between where our parents were. It was like the corporation is the good work for the good of the company. We were kind of in between that of still like this kind of like empathetic large mindset, but starting to focus on ourselves. Gen Z's grown up in a world where like, you know, you really have to like, you are your own business from day one and your personal brand and everything like that really is the currency that you take into the world. So they test less empathetic. But at the same time, I think both, both generations will find ways to give back if given the right ecosystem for it, which I don't think we currently have. I think people trust large nonprofits, you know, and we're, you know, we're taught that, you know, any kind of dispensable income that we have at all, you know, should be invested and saved immediately. There's not really like attachment to religion like there used to be. So, you know, I think it's about like figuring out that next step. I will go back and start that company at some point. So.

Oh yeah. One thing I wanted to talk about was I think we discussed this in the past, the idea of like founders or entrepreneurs A lot of the time you don't need some big swing. You just need to be of service. And usually it's from like select few. It seems like the origins of it was just being of service to your friends, like the people immediately around you and see what they needed help with. And so tell me about those origins versus like these big ideas, taking these big swings, which again, I'm a huge proponent of, versus it seems like the paths you've gone down, which is, hey, there's this problem. I just want to help out if I can. And then over time, oh, like this is actually monetizable, can hire a team and scale from there.

Yeah, absolutely. I mean, I think that like a lot of the best businesses didn't start with some kind of like, you know, I was talking to an investor this morning. He's like, oh, I would love to be in your shoes. I'd love to be a founder, but I haven't had like that idea yet. I think that's kind of a misconception that like founders sit around and then all of a sudden, like this big light bulb idea pops on. It's like, no, most of us do it because we need to. Like this. It's like what was been in my blood since I was born. Like I would— I'm not able to go and just decide to be a VC. Like, I, I, like, you know, I live and breathe because I can start companies. And so it was just what works now, and then how do you continually evolve and grow that and change that into being something that will work long term. Um, and so I think most founders, I mean, from, you know, Airbnb to Uber to everything, it was because, like, it was what they needed to do. And then what changes a lifestyle founder from, you know, a really successful founder is the ability to take really the same origination of ideas and evolve it and grow it into something bigger. Yeah.

How is your skill set specifically about leverage, capital, time, labor improved with each business that you've run?

Yeah, I mean, I think it's just through hard lessons learned, right? I mean, you get a little less idealistic every business you get. In my, in my experience, you get more empathetic. You know so much more about what drives and motivates me now. It's also stage of life, right? I was so young and everything is just about like the, like the, the need to be successful at that stage. And now a lot more of it is like protecting my family and protecting the families of like the, the people, our team that works for me that like you care so much about, you know, now it's not like, oh, layoffs mean I can get more efficient. Now it's layoffs mean that, you know, one of my teammates, uh, aren't gonna be able to pay their rent and they just had a baby. Uh, you know, it's, I think like the motivations and the drive changes and that really only I think comes from like being in it and learning and seeing firsthand how it actually all works.

You know, where have you seen yourself level up over the years with your successful businesses and your failures?

Yeah, absolutely. I mean, I think, of course, like the typical— I like— I didn't go to business school. Like I minored in entrepreneurship, but I was a philosophy major. You know, I've always loved to think and I think I've always loved to be creative, which is why I love marketing as a, you know, as a realm. But starting businesses, like I didn't come into it with let me tear through my P&L this week and like see how we can cut off X. And it was like, let's start a cool idea, hire cool people to do it. And I'm happy that I came from that background because I think you can always learn how to get, how to become a better businessman or businesswoman. I don't think you can learn how to be a fluid and creative thinker. And I think it takes both.

Can't teach cool.

I just don't think I, you know, I don't think business school can teach you what it takes to actually run a business. And so you have a lot of people that really struggle because they have all this great technical foundation, but they haven't been through the, the ups and downs of just going out there and just absolutely doing it.

This isn't an opinion that I think I publicize a lot, but I think I've mentioned this to you, but I'm, I'm also an anti-business school person because my perspective on it is, would you rather trust the person who just reads about starting companies or the person who just like rolls their sleeves up and starts companies and iterates and fails and learns?

Yeah, I mean, it's why like on an investor side, like we, we— it's a hard line in the sand that like we only work with investors who are past founders and operators.

Um, that's how your company is?

Yeah, absolutely. I mean, it's just like, I— it's nothing against, uh, other types of investors, but I just think to understand actually how it is in the day to day. You can't have graduated from Harvard Business School, gone to Goldman Sachs, gone and become an associate at a VC fund, and then become a partner and actually understand what it's like in a founder's shoes, you know?

Yeah. I will say that to your point, a lot of my— I'm very much anti-business school, even though my dad, every time I see him, he's like, so is it still, still in the cards that you're going to go? Same. And I'm like, man, I'm telling you, I'm running a business now. It's going okay.

Yeah.

But I will say a lot of the guys I went to— I'm 27. And so this is around the age that a lot of my friends from college are in business school now.

Right.

And there are a lot of them that went down credentialed paths. So say like went to McKinsey for 2 years, then went to like private equity for 2 years. And then now some of them are in their like second year at like Wharton or something or Harvard Business School. And I will say like having those conversations before they went, they were so on paper way smarter than I am, but they were like lost in a sense. Like they didn't— they genuinely didn't know what to do. So there are, there are a subset of people where I think grad school and business school is like a great idea if you feel trapped and you don't know what the next option to go to is and you have the money. Yeah, I'm okay with it.

It's a stopgap.

I think it's a stopgap for exploration.

I agree.

Yeah. Well, I mean, I think it's a, it's a, it's a push of exploration. Like you can also do a lot of things there where like you go out and you hustle and you make something work.

There are other options.

Instead of spending $200 grand to go like extend partying for a couple of years with your buddies. I mean, and I'm not anti-MBA like by any stretch. I've actually always imagined that like, like maybe post-exit at Selectree, I'd go back and do like a— like the only one I would do is Stanford Entrepreneurship MBA because that's just like to me the only real one, you know? And but I just think that like if somebody is doing it to like delay all they're doing is like pushing. They're going to get done with that, and then they're going to have to go through the exact same experience that we all did just trying to learn anyways, right? There's only one way to learn, and it's actually doing it.

And there's always, at least from my own experience, there's this period of like the unknown where a lot of people can't withstand that, whether it's 1 month, 3 months, 6 months. We're trying to figure out that idea, and there's no like backstop for you, and people can't handle that stress or fear. And they find themselves 40 years later in like a corporate role because they weren't willing to just take like one small risk.

Yeah. And I don't think that's anything against like, Lord knows we need those types of people. But at the same time, it's, it's almost like a personality type. Somebody who like needs the path. I mean, good luck being a founder just because there's no path. There isn't. Even if you study at the best MBA in the world, you're going to graduate and you're going to learn as soon as you try to start a company that there is no playbook. There is no life without ridiculous curveballs. And the only way to learn is actually doing it. There's only one real MBA to be a founder. It's just being a founder.

What is life for Zach like away from the office?

You get away from the office?

That's a dumb question.

No, I mean, we're heads down. I think there's different perspectives on that too of like— Tell us yours. Phone stays strapped.

I think I got it, but I'm just saying.

If you're developing a lifestyle business, I have nothing against. I'm not trying to build a lifestyle business. I'm trying to build a billion-dollar business right now. And that just like the admitted sacrifices are different there. So, you know, yeah, I'm 120-hour-a-week worker. That's just like what I mean. My dad was 120-hour-a-week worker. It's like what I grew up with. I mean, it's just, it's what I know. And so I, you know, of course, like I love seeing my friends. I love, you know, going to music festivals. I love, you know, you live in Brooklyn, you love to go see music and do things. But at the same time, um, work is— work is definitely my life. Um, and I'm, I'm blessed to be able to do that because I have an incredible wife who supports me and is there and, um, and like has, you know, understands the lifestyle that we've taken on to, you know, to try and build something great, you know.

Walk us through a day in the life, what time you wake up to the time you go to sleep.

Yeah, we just talked— we talked a little bit before we got on about how much I love mornings. So I think like I'm like the normal person, 8:30 wake up. It's like, yeah, I am. I'm like, I'm like 8:30 wake up, coffee's on the bedside table, get up, you know, take the supplements in the morning. Uh, I, I don't take meetings before 11. Um, I very rarely do like anything like this before 11. So it's like, oh, it's all kind of like thought work, planning work, everything like that before, like while I'm trying to get through, like, and then I'm heavy on meetings, uh, you know, at this stage of my career. And so it's, you know, normally 11 to 5 is back-to-back 30-minute meetings every 30 minutes. Um, you, you go out, you try to be a good husband, good friend from like 5 to 7. And then almost every day from 8 to 2, I'm working, just trying to do focus work afterwards. Yeah, back in the office, just, um, you know, I think like, yeah, at this stage my day is so meeting heavy, it's impossible to do any thought or focus work from, you know, 11 to 5 or 6 PM. And so the only time that I'm actually able to sit down and like get anything done is when the world quiets down, when people stop emailing me, when you know, the wife goes to bed and like, and everything's quiet.

So from that 5 to 7 stretch, I have an oddly similar schedule to you. From that 5 to 7 stretch, one of the things that I'm confronting right now is that, you know, the 3 big things I always try to think about is take care of yourself, take care of your people, take care of your family. So close friends, relationship, family, and yourself. That's a lot to do from 5 to 7 every day. And usually one of those hours I'm working out because I'm trying to take care of myself.

Yeah.

And usually I'll have maybe 5 to 8, so an extra couple of hours. And increasingly I'm so— not all days, but sometimes I'm so fatigued after you come out of just this spin of like 12 back-to-back calls.

Oh yeah.

How do you show up for the people that like you really care about?

Yeah, that's a great question. So I've thought a lot about this year, especially mostly because my whole career I always had— I always had an external office. You know, Select Few, we're remote and my office is it's an office in our apartment, right? And so you always had, and I think almost all of human history, you had the commute home, you had the, even the walk back from the office to like decompress from a really intense day when things don't go right. And you had that separation between the family that you want to make sure that you show up for and an absolutely crappy day at work one day, right? And for me this year, it's been, you know, tough day at work, you open the door, she's so sweet, dinner's ready, you know, how was your day? And like, you just got annihilated for the entire day, you know? And so like, that, that has been like a completely different type of like mental separation to be able to build. That's like almost just like completely unnatural, but one that I, I've had to because I just refuse to bring that even on the worst days into, um, like the only reason that I work at all, which is to protect her, you know?

So Your work is not who you are.

No, it— yeah, sort of. He's like, well, I actually fully disagree with that statement.

My business is me.

You know, but it is though, you know. And like, your work isn't who you are, but I think like, uh, it, it is like just undeniably a massive part of your identity in your life. You're going to spend more time at work than you are off work in your life, right? And so, uh, while it's not who you are, I mean, I think the good parts— you don't hesitate to bring the good parts of your work into life, right? You don't hesitate to go out and celebrate at a dinner with your, with your friends when something goes right. Um, but the opposite is just, you know, unacceptable to a certain limit. Like, you have to have your support system, but, um, you have to find a way to build the mental models to leave the bad things at work. And I think that it just requires a different type.

What's driving you though to have this level of work ethic? Because it doesn't seem like money is the only thing in this picture.

Yeah, no, definitely not. I mean, I think, uh It does. Like, I mean, I think with money it's always an interesting, like, dynamic of whatever you— whatever you get, wherever you get to. It's not like you always need more, but it's that, like, there's always a different level of how much that you can protect your, your family and friends, you know, like first exit, it's like, okay, I'm going to be fine. Second is like, my family is going to be fine. The third is like, oh, my extended family and my sister's daughter is going to have her college paid for. And like, those are still things that drive you, you know, like there's still things that kind of like make you want to go next. So it's not like money is never a driver, but it's also that, yeah, once you, once you, you know, have success in one sphere, it's that push of like, can I do it in another one? Like, you know, for me, like my last exit was in a consumer brand. I knew I can run a consumer brand to exit. Can I build an AI company? That's a completely different kind of journey. And so I think it's also just like the desire to keep challenging yourself. Right.

Is it also just pure fun for you? Like, there's work-play, or is it?

Absolutely. Yeah. I mean, it's, it's my— I mean, it's my dream job. I mean, that's the thing. If I, like, if I had to exit Select Few tomorrow, I would either start a different version of it or I would start the same thing. Like, I, I show up to work every single day, like, absolutely obsessed with what we're doing and believing that we're actually building something that's unique and amazing. And so with a team that I got to, you know, craft from the ground up with people that are like, you know, that are, that are my type of people that are there to do the same types of things and change the world in the same type of way. And so it's the dream job. Like, what else motivates you, you know?

So I'd be curious to hear about your management style. Like, I'm sure it's unrealistic to expect all your employees to work the same amount of hours that you do, but I imagine there's some level of rigor that you've built in, in the environment. I'd be curious for you to go a little bit deeper on that.

Yeah, no, I mean, my management style has definitely changed a lot over the years too. Like we were talking about building empathy over the years, figuring out that everybody is not you, everybody's never gonna, I think early days, if an employee wasn't working as hard as I was, it was unacceptable. Now you realize that even if they love their jobs, and at Select Few we have 100% employee retention since launching the company, we have people get offers at Google and stay despite the fact that they make a lot less. And I think it's because we've built an environment that understands that, yes, of course, like, this is an early-stage startup. Hard work is a baseline floor, but that everybody is like living their own lives. And it's not— even, even though they own parts of it, it's not their company. It's mine. And, and realizing that nobody's ever going to care about it as much of it as, as I do. And that's okay. That's how it's supposed to be. And like learning that and kind of like allowing people to build a work system that works for them has been a big kind of evolution in the management style. I have very different types of people that work for me. I have the, like me, always on, on Slack 23 hours a day, and I have the people that do really great focus work for 6 hours a day and then are off and living their lives and with their families, and realizing that that's okay and trying to build an environment that performance is judged on clear KPIs that the entire team knows and building like a really transparent business system. Versus trying to expect the same things from very different types of people has been the main evolution for sure.

Yeah. How is your management style grown?

Uh, it's definitely, it's definitely started to go more towards like auton— like I really appreciate people who are autonomous.

Yeah.

I think like when you're thriving in an environment of chaos, micromanagement is the absolute— I think that can kill a lot of businesses. So I think for me it was about getting over this hump of trying to micromanage and recognizing that I either need to trust these people that we're bringing in or find someone else to do the job. Because I've realized that it bogs me down and it, it just— nothing is efficient. So I would say at this point it's really like, here are the guardrails for what your job is and what you need to accomplish. Like, now I'm trusting you to, to think critically about how to approach the problem. And if you need help, you can come back to me and ask me questions. But like, you're, you're driving this part of the business.

Yeah.

Yeah. And that style of management is definitely just what like this period of work in the world requires. Because I mean, how nuts are the micromanagers going in a world where like everybody works remote and you don't like— and you don't know what people are actually doing all day? And like, if you haven't— if you don't build a style that the performance is based on studiable, objectable goals, um, it's, you know, you'll drive yourself crazy as a, you know, as a manager trying to sit back being like, are they doing what I think they are? Like You know, for us, one of the, one of the values that we hire for is called an engine-on mindset. Like, I hire people that I can trust without sitting there thinking like, are they working today? Um, I know they're working on their problems. And with that kind of like barrier level of trust, I'm able to like really take a step back and never micromanage, you know? Um, which sometimes works against me. I would say I like err on the side of trusting over micromanaging, but to me that's just where I've kind of like decided to put the foot in the sand and be like, This is, uh, I would rather trust my people too much than drive them crazy by trusting them too little.

That— it happened for me, like, I think the moment is when we started hiring in different time zones.

Yeah, exactly.

So I was like, I can't, I can't sit there and like know what you're doing or when you're doing it if you're, you know, 6 hours different than I am. So at the end of the day, I'll see what work you either did or didn't do, and you have to take that and move forward.

Yeah, exactly. We have a team in LA, we have a team in Columbus, Ohio, we have engineers in Toronto. If you just try to like and know exactly what everybody's doing all the time, you'll go crazy, you know?

So how do you— I question both of you. This is something I realize sometimes I'll show up to a meeting after you just get slaughtered in back-to-back calls, like, yeah, you lose a deal, customer turns, someone— it's like, okay, great. That anxiety or like paranoia, how do you compartmentalize that and then show up to the next team meeting energized, jazzed about the vision, even though you just took 3 L's back to back.

It's a really good question and something that I really believe is the, the evolution of how to be more steady as a founder and a leader. I mean, there's a lot of like stoicism in that and like not letting the highs get too high and not letting the lows get too low. You know, I had like the hardest test of compartmentalization in my life this year. I was at South by Southwest. I was speaking in front of like 500 people at like an event that we were sponsoring. It was like all of our ICPs. It was the most important, like talk I've given in my entire life. And 10 minutes before I stepped on stage, got a call that somebody— I'm not going to talk about it here, but like somebody in my immediate family, you know, got diagnosed with cancer and got that call, you know, crying 10 minutes before I stepped on stage to go give this talk. And it opened with like 6 jokes, you know, and being able to like— I was like sobbing in a bathroom stall. They're like, Zach, we're ready for you. and I had to just like step up on stage and, you know, I'd like to think I crushed it. And it was like, that was like the— I was like, after that, I know I can compartmentalize anything. Like, after that, like, I know you have the ability to be like, this sucks, put it in its place and move on and get done what you need to do, right?

I think the problem is that it becomes distracting when you try to make other people's problems your problems, and it takes just like a level of extreme discipline not to make it happen that way. Because if I have a bad call and then I get on the next call and bring that bad energy into it with someone who has no context, it just like ruins that entire environment and then it just snowballs into a bunch of like unproductive conversations.

Yeah, it's more difficult to do too in our world where like back-to-back Zoom meetings is so different than a world 5 years ago where like you would take 2 meetings that day but it would be like this, we'd be sitting here chatting, you know. It's hard to drop what happened on a Zoom call and then 2 minutes later get on another Zoom call and, and have that like instant compartmentalization, right?

Yeah, I think what can be stressful, especially given the roles that we're in, because a lot of our job is sales and hiring or firing sometimes, um, and not in like the process or building, business building part of the day, but in the back-to-back calls, sometimes even if I've tried to compartmentalize when you realize the stakes that are on the line. Say you're closing a big deal, right? You being— you showing up with like a steady, focused, happy energy, and you being a little off-kilter, you could lose $100K, right? Maybe more.

Easy. Yeah.

I mean, how do you deal with those things?

You lose a $2 million lead check, you lose— and then the stakes as you grow just get higher and higher. And like I was kind of alluding to was, you know, for me now, the, the one of the motivators, but also the weight when things don't go well is, you know, we have such a, a close-knit, amazing team that, you know, it's no longer just I need to do what's right by my family, it's I need to do what's right by 15 families. Um, and I know a lot of their family members, I know a lot of their kids. Uh, and so, you know, the weight gets even more when like something doesn't go right. Uh, but that's what brings it to the importance of owning your own mind and flipping that back and being able to get back to a steady state gets even more important.

I think I told you this story, but I, I was never able to relate what you were just speaking about until the first time it happened in my young entrepreneur career was a couple months ago. We had an employee who almost lost a child to a genetic disease at birth, and then like 2 days later, another employee's, uh, 12-year-old got punched in the face and bullied at school. And it was like one moment after the other when you realize they're on your health insurance. And it was just like a very stressful week for my co-founders and I because we're a very intimate team. And that was like one of the moments when I was like, okay, this is one of the reasons why I'm doing this to begin with, is because it's something so much bigger than yourself and you have the opportunity to help support not only your team but the extension of them as well.

Oh, exactly. It's not just your family anymore. It's, it's, uh, you know, through extension of, of that, it's 100 people that are affected and that are, you know, on our health insurance and that you need to know that you can protect. And so, uh, it makes— to me, it's— that's what's most rewarding about the job is, is like supporting and driving, you know, all of us as a family, supporting all of our families, uh, versus it just used to be like, I gotta get rich, you know.

So we talk a lot about supporting others, but I had a mentor of mine a few months ago asked me, he goes, Ben, I know you like, you have all these employees and you're doing all these things, but like, who's looking out for Ben? Like, what are, what are the things you do in your life where you're, you're actually trying to take care of yourself, whether that's mentors, therapy, etc.?

Yeah, definitely. I mean, uh, I think that that's the weight that only the leader of the company has, right? Because everybody else the company looks to you for support. And, you know, I like to— I've always had a supportive management style versus an authoritarian management style. Like, I'm— I think that the more employees you have, the more people you have to serve. Like, that's just how it goes. Um, but at the same time, yeah, there isn't somebody that you can always lean on. And I think having advisors is great, having mentors is great, but at the end of the day, it's the evolution of what only leaders have to go through, which is at the end of the day, you're the one who has to be there for yourself. And you have to be able to build the mental models and build the habits and build the systems that keep you comfortable and, and happy even in really tough times. You know, for me, it's like finding a time every day to just do something that I love, whether that's you know, sitting down at a bar in Brooklyn and having a Miller High Life with a buddy, or whether that's like taking a walk and listening to an audiobook of, you know, some random fiction book I've always wanted to read. Like, it's just a must that has to happen every day because otherwise, if you stop taking care of yourself, no one, no one else is going to.

What are your other non-negotiables?

You know, like I said, like kind of hinted at, like one huge one is leaving work at work. You know, I'm at work so much. That I can't bring work into the 2, 3 hours that I'm with friends and family outside of it. It's just that's a non-negotiable for me. Normally not doing things in the morning is a non-negotiable for me. But I think it's, you know, outside of that, it's finding the ways to make sure that you take care of yourself first. And I think that's been a big thing you always see on Twitter and stuff like that. Like, as a founder, you have to take care of yourself first. I used to always think that was kind of selfish or kind of a joke. I've realized that a lot over this year, that when I start slipping on taking care of myself, I start slipping on how well I can take care of others, you know? And it really is a big priority.

I think the fun and play aspect is really undervalued. Some weeks I'll go by and I realize I haven't really had fun fun. Like, you can have valuable time with your spouse or with your partner or with your family, but just pure play, but you're just like laughing and enjoying yourself or cracking jokes. There's a— did you guys see the Arnold documentary? Yeah, on Netflix.

Yeah.

And I think the third one, someone was asking him why he was driving this massive truck through the wilderness. He was like, and he was smoking a cigar and he was like, what do you mean? This is play. Yeah, this is a ton of fun. It's a toy. And he was like astounded that they would even ask that question. Yeah. But for you, what is that? Not just, you know, taking a walk to breathe.

Yeah.

But like, how are you really having fun?

Yeah, absolutely. I mean, it's, you know, I think a lot of us who are in our positions that are we're not like genius-level engineers who are founders. We're marketers. We're social people. And so it is time around friends. We have to throw a dinner and get 30 friends over to the house, and I'll be up playing darts until 2:00 AM. It's like, after a night like that, I'm infinitely more energetic the next day at work versus I think how that removes and takes away from some personality types. I need it. Like, I have to see my friends. And then of course, like, I'm really close with my family. My little brother works for me. That's luck for you. Yeah.

What does he do?

He's an SDR.

I thought you were going to say CEO.

No, he's younger. He's awesome. He's a badass. He hits his quotas. He's great. And, you know, I was pretty hesitant to do it at first because, you know, he's my best friend. You know, we grew up in— like, we're kind of talking about a pretty crazy world together. Like, you know, buddies from, you know, being, you know, the only American family out of 200 in a little village in the jungle. And so we're close, we're best buds. And so, uh, he actually, he asked, he was like, look, I've done other things in my career, I've seen you build Selectry from the ground up, I care about it, I want to sell something that like I really believe in. And, um, you know, the instant answer was just like, of course. But, uh, the worry was always like, if, you know, how, how do, how do, can I blend family life and work life in a way that, you know, what will the other employees think, that he just got his job because he was my brother? How will he treat me at work? Will he treat me with the respect that other employees do? It's been an amazing experience. He's been fantastic. He's an incredibly hard worker. And I think I had good guidance on that because actually my mom's a CEO of her business. My sister works for my mom and they've had a good experience. So I've been able to see that firsthand.

How hard are you on yourself?

Um, I think I've learned to be less hard on myself. I think when I was 23 starting, you know, um, ArtLifter, which is the company at the time, uh, I was devastatingly hard on myself. You know, this is something that I've— I, I, you know, I mentioned on, on podcasts and I talked about a little bit in the past, but why being mentally healthy as a founder is so important to me. You know, after— so when I was 23, we raised venture I was building, uh, like a hyper-localized art marketplace trying to bring like up-and-coming artists to be able to sell work to young adults that wanted to stop buying the same 5 IKEA prints in a way that would get kind of like undercut the very expensive gallery world to a place where the amazing artists growing up could, uh, could, could make money. We raised venture for it. I made every mistake you could make as a 23-year-old founder. I had too expensive of an office, did a lot of too too many happy hours, hired all my friends. That business ended up like, you know, we just definitely didn't have product-market fit. Art was a really hard industry to build in. And so we folded that company up. I had to fire a lot of my friends. I had no mental frameworks for how to separate failure of the business from failure of myself as a person. And so I, um, tried to take my own life a couple times and like really struggled with like, with, with battling suicide for like a year after that. And had some really hard times that year. I, you know, I moved back in with my, with my mom, like, you know, who was also kind of having a hard time at the time. And, you know, we kind of promised ourselves like, look, this isn't us. We're going to find the ways to build the mental strength back up to be able to do it again because she's an entrepreneur too. And, uh, and, and so like, that's why things like meditation and stoicism and building the models that like work for you as an individual are so important to me. It's like, that's what dragged me out of like the depths of kind of like failure as an entrepreneur, and why now I have a lot more separation between what happens in the business isn't what is happening to me.

I think that's a pretty good segue into the name of this podcast. I, I'm assuming that's one of the moments, but we call it Turning Pro, and the idea behind it is when you think about getting up from one poker table and going to a higher stakes one, and recognizing those moments in your own life when you're taking things to the next level like, what would you say are a couple of highlights that stand out to you that really were indicative of you, like, leveling yourself up?

Yeah, I mean, I think I had the benefit of having a really early experience like that. You know, I built and sold my first company when I was 16. And so having an exit at 17 definitely was like, okay, great. Now I have a bottom barrier to entry that like what I do next can't just be a fun business I run for a couple of years and then fizzles out. Uh, which is of course exactly what happened next. But having like that first barrier to entry, that, that first— I know from a very early age that I can do this, but I think a lot of people question whether they can— was a huge moment in kind of like leveling up entrepreneurship for me. Um, you know, I think the next one is— was that first failure. Like, that first failure hit— hurt way more because I'd had a first success before that. And, uh, finding the— and now I'm so thankful for for that because, uh, there's no way that we would have been able to survive the ups and downs and challenges that we've had, even at Select Few, this, this run, if I didn't have that experience of trying to crawl out of failure first. Um, and so I think it's like just as important as like the successes teach you that you can do it, uh, the failures teach you that, uh, the worst is not that bad, you know. It's like that stoic idea of What's the worst that can happen? That's not that bad. You'll be all right. And so that the highs aren't that high and the lows aren't that low, which is that kind of like level mindset you really need to be a founder, right?

What's your, when things aren't going perfectly well, not just back-to-back calls, but maybe like you didn't sleep well the night before and you're taking Ls and you can't get through something. What is the self-talk when things are difficult or the weeks when you're a bit down? You know, because it's really easy to reschedule the next few calls.

Oh yeah.

And pass things off, take tomorrow off. When things get like that, what is your self-talk?

Yeah, that's a great question. I mean, yeah, we've definitely had experiences like that this year. We, like, we had an investor sign a term sheet and missed 3 wire dates and then end up not being able to call capital from their LPs. And so like money that we had planned for for months just like ended up being like, oh, sorry, that's not coming after like an entire diligence process and everything like that. All of a sudden it was like sitting up until 4 AM every night being like, we overhired, we're in trouble. And then that goes back to exactly what we're talking about of like, I'm going to have to kick employees' families off of health benefits. Like you go down this spiral, right? And I think there's only two avenues there. One is like falling into like a despair mindset. It's, we're in trouble, this is it. The only other mindset is like, is a fixing. Like what is the next step? What is the next solution? You know, my mom, who I've mentioned a couple times, but just, she's a real mentor of mine, successful entrepreneur and founder. And, uh, you know, she, she alludes it to that, to, to this like metaphor of, uh, as a founder, often like you're, you're the juggler on stage and you have to realize that there are certain balls you're juggling that are rubber and certain ones that are glass. The glass ones are the ones that cannot be dropped no matter what. These are ones that are your mission. Mental health and your family's ability to, uh, to be okay and to be safe. They're the core structuring and taking care of customers in the business. And then there's the rubber ones that it sucks to drop, but like every juggler is going to have to do it eventually. And I think for me this year has been a really big exercise in realizing that some things I thought were glass are actually rubber, and some things I really cared about, the business is going to be okay no matter what. But it's about like leveling yourself with those things And then just working on what's next, you know?

So who's the first person you call when you have a success?

Definitely my wife. I mean, she is like the ultimate partner for me. She's there through the ups, there through the downs. Also, it's never much of a call because she's always like right on the other side of the door.

She can hear it.

Yeah, exactly. She, she hears the wind, the— you know. And so, you know, she's, she's my partner in, in good times and bad. You know, when we sold my last business, it wasn't like a super clean and easy process selling that business. I was a co-founder with a brother and a sister, which was a unique challenge. And I didn't want to sell that business. I loved that business and wanted to keep running it. They decided that they wanted to exit and kind of get out while we were kind of in a good place and we had a good offer from a private equity firm. It put us in a place where when we started in negotiations around exiting, we we actually froze all salaries, which was— they were in a very different place than I. They were twice exited out. I had just asked Morgan to move in with me, and all of a sudden salaries were frozen while we were working for the next 3 months on negotiating this exit. And all of a sudden, I had told this, this beautiful woman, hey, move in with me, I'll take care of you, all this stuff. I'm about to sell my company. Now all of a sudden, like, I didn't have rent to to pay the next month. And I had to tell this, this beautiful person who just moved in with me, hey, like, uh, I actually can't get rent this month. And, uh, her first thing out of her mouth was, hey, I've saved up, I've got rent for the next 2 months. Whatever you do, you get back to starting something next, because I know whatever you do next is going to be even better than this one. And it's like, how could somebody who, like, supports you like that not be, like, an ultimate partner in life? And, like, the person that you get to celebrate the highs and, uh, get through the lows with.

You know. What are the characteristics you looked for in a partner? I think you've alluded there so many times in being such a big part of your life. I'm just curious to go deeper on that.

Yeah, absolutely. I mean, I think, uh, you know, I think her and I both had been, uh, I dated a lot before that in kind of like seeking the right partner. It definitely wasn't like I think somebody's gonna fall out of the sky. I think it was a process of like realizing what works for you and what doesn't. I don't think like so many people are like, I'll go on one date a year and I think I'm gonna fall in love. It's like No, no, no other thing in life works that way where like you don't have to try what doesn't work to find what works. And I think because of that, like I'd gone through it kind of, I think like with a weird founder mindset of like, okay, this didn't work and this was why. Like these are the characteristics that didn't work for me.

Like this postmortem journal.

Yeah, exactly. Like, you know, I don't have some like notes somewhere, but I do think I was like, like, you know, subconsciously building that mental model of like, okay, I knew this didn't work out of like, this is what wasn't it. Right.

And hold on, I want to, I want to flip the question because I think it's going to be a more interesting answer. What are the common traits of the dates that went terrible?

You know, I'd like to say that I never had a bad date. Like, honestly, looking back, like, I didn't have any, like, first dates that, like, were terrible. Not even first.

Yeah, just the ones where you're like, this is one.

It was just ones where it was like, this isn't going to work, you know? And I think, like, you know, I don't know. That's a, that's a good question without, like, publicly calling out some of the people I've dated in my past. But, you know, I think it's like that, you know, it's like It's that, you know, when you're thinking through ideas to start a business, you know, ones that like aren't it because of what you've tried in your past and what worked in like your limited experience. And so that when you finally find something and you're like, I think this is it, I think I'm on to something. I honestly felt the exact same way when I met Morgan. It was like the second I met her, it was like I've— what I've learned and like and struggled with in my past and like, this is it. And so it happened really fast. I mean, like 3 weeks after I'm like when I asked her to move in with me, that was 3 weeks after we met. I told her I loved her like a week after I met her. It was like very fast because it was like, I know that this is like— I've worked through other, the other options and other, other, other types of people, and like this is the one that, that I think, uh, like her and I are meant for each other.

So do you agree with me? Maybe this is a hot take. I've always said that like women don't necessarily grow on me. Like I'm very much a love at first sight type of person as well.

Yeah, I would say like I, I would feel that way in almost, almost anything that like First reactions are more right more than you probably would guess. First reactions of like, if you trust somebody, first reactions on like how somebody will be to work with. Like I really am like a strong believer in like the power of your subconscious and like trusting your intuition. And like most of the times in my career when I have been like, I have to make sure I gather enough data before making this, like I've regretted it. My intuition has been right, you know? And so I think I was the same way in my love life where, you know, like my intuition told me that this was it. And I've been, been blessed to resoundingly have that answer be yes by having an amazing partner.

So I have a Post-it note in my room right next to my desk that says, all your intuitions are true.

We—

yeah, I proposed to Ben on our first call. I said, you want to start a podcast?

There we go.

A podcast proposal.

So I'll give you how it happened. I'll give you the quick 2 seconds of how we met.

He—

I think he requested me on LinkedIn. I clicked on his profile to see who he was, and literally I was like distracting myself because what I was doing was boring me, which was actually looking to hire like a head of marketing. And trying to figure out like the salary range to do content stuff. And his company literally did that. And so the timing of him requesting me was so weird to me. So I messaged him, I was like, hey, can we get on a call? Because I was actually looking into trying to solve this problem in real time. And we got on a call and just like hit it off for 30 minutes. He's like, you want to start a podcast? I was like, yeah, fuck it, let's do it.

Love at first sight.

I love that, man. Sometimes, you know, I, I've got, you know, 3 people. It's like when I start a podcast, these are the people that are on, like that's what we're doing, you know. So yeah, I think it's I think your subconscious picks up a lot more than we give credit for. What you kind of think consciously is a very limited perspective of what you've learned in your life. And there are a lot of things that are kind of held a little bit deeper. And so yeah, I think that people undertrust gut reaction and intuition. And I think, especially in a world where I think as marketers too, we're so driven by data, everything has to be data-backed. The best marketers that I've ever met do a lot by the gut, but do a lot on the wing.

Do you have any regrets? I mean, what are your biggest regrets?

Who doesn't have at least a couple of regrets? I mean, looking back, it was— but I think those regrets are obviously necessary for how to grow. I mean, I look back at— we kind of hinted at growing and maturing and changing as you change as a manager. I was definitely an arrogant and cocky manager and leader when I was young. I think humility comes with mistakes. Uh, at least it did in my experience. Our early success meant I thought I was a god early on. And, uh, it is, you know, life loves to remind you daily that how untrue that is and how lucky, uh, you can be when you're successful. And how now, like, for me, like, success is driven by being considered, uh, a great friend, a great partner, a great manager, great team leader. I'd like to think that people really enjoy the experience of working for me, which is something that I didn't care about at all when I started. I cared about monetary success.

Tell me a bit more about designing your environment. We talked before this about LA, probably moving around LA, I'm guessing, a bit, and then moving to New York. And you mentioned you kind of like found a home here.

Yeah.

Tell me more about living in Brooklyn, why it's not your optimal lifestyle, but why it fits kind of like your current season of life.

Yeah, absolutely. I mean, it does. It fits the currencies in my life perfectly. I wouldn't rather be anywhere else in the world, in any other neighborhood in New York than me living in Brooklyn. I just absolutely love the pace of things. I love that you get the speed and the hunger of why people love New York so much. I mean, like you were talking about earlier, it's just like I couldn't be in LA because people aren't like, you know, visibly as hungry. So you kind of lose pace. Brooklyn is kind of like a nice balance between those things. Where, you know, you have a bunch of absolute savages on the sidewalk, but at the same time there's a little more calm and like neighborhood feel to things, which is like the season I am. I feel like in my life I'm hungry as I've ever been, but I am not, um, the savage 23-year-old that I was, you know. Um, and so I, I, I think it's like, yeah, it's that reflection of that. It also is, I like, I can't sit still when I work. I can't sit in a chair for 12 hours straight. My back-to-back calls, 90% of them I'm walking. And, you know, I love to be like out in Brooklyn walking around the sidewalk, walking through Domino Park, um, and, uh, and like I take all my best calls like on the move. And so, uh, you know, it's, it's kind of a nice like balance for that season, you know.

It's funny, I, uh, I was in— I didn't realize, but I was a block away from you for 2 years. And moving up to Greenpoint was great, but the one thing that I do miss is is I literally got an office in Williamsburg because I need— I just need to see people walking around all the time. Um, Greenpoint's beautiful, but it's so quiet.

Yeah.

So sometimes when I work from home, it's just so still that I'm like, I want someone like shoving me a little, like, on my way to work. You need that.

Exactly.

Yeah. Well, when you don't live with a female, you can just turn your apartment into a WeWork.

Yeah, exactly.

You can have a podcast studio in your living room, which I absolutely would never do.

We need a podcast studio. Yeah.

It's also just It's like, you know, when I'm not, when I'm not working, what's better than great restaurants? What's better than like hanging out in little dive bars with your friends? And, uh, there's just no better city in the world than that, than Brooklyn.

Yeah, this was, uh, very well spoken and articulate. Like, yeah, I think your story, your story is so— I can't wrap my head around it. Like, you grew up in the jungle.

Yeah, had a pet sloth, had a pet toucan.

Do you, do you keep— I guess one question I do have, do you keep in touch with anyone still?

Yeah, yeah. And you go back there? I haven't been back to Ecuador a long time, but some of my friends from Ecuador moved to Colombia. We go down to Colombia a good amount, spend a lot of time in Medellín. And, uh, and so still have friends from that area in my life. Yeah, absolutely.

I, I mean, I don't think many people can take lessons into their later life, life like you have from living in a jungle.

Yeah, I mean, you know, growing up in a place where, uh, people were super happy with so little teaches you a lot about you know, like I was talking about, in things are going to be okay. You lose that big deal, things are going to be all right. You, you know, you, you have a really bad string of calls, it's going to be okay. You know, when you see people who the average income is like $8,000 a year and they're some of the happiest people in the entire world, and you grow up around that, I think it gives you a nice barrier to like the lowest low. It's going to be all right, it's not that bad.

It's all perspective.

It is.

When you're exposed to something bigger, you you can never like go backwards in it, at least with like my, my recognition of it. Cuz when I have been to places that are way worse off, I guess monetarily, like you said, they're typically happier because they don't know what they don't know.

Yeah, exactly. Well, at the same time, it's that life isn't that bad in that way either. And so like, you can, you can fail in a business, lose your nice apartment, go move into a crappy one, and if you, you know, if you know yourself, you're confident that you build it back up and that you'll get back there. You know, like the worst things are not that bad. Um, as long as, you know, you, you know, to me, you become a person that you're more and more proud of, that, that, you know, you're building and becoming a part of a team that you're more and more proud of, that you find real challenge in your life. And if you can do those things, uh, the worst calls are something that you can flip off and be good on the next call, you know?

Oh yeah, love it. You want to do us a favor? Just look at the camera, let everyone know where they can find you.

Yeah, sure. Uh, Zach Holland, Select Few, uh, on Twitter, Zach, Z-A-C-K underscore Holland, H-O-L-L-A-N-D, on selectfew.co. Hell yeah.

Thanks for coming on, man.

Yeah, of course, man. This is awesome. Appreciate you guys having us. Appreciate it.