From Yext to Roam: Howard Lerman’s Second Act

A founder has so many things that are flying at them from all directions, and they just don't have time for social stuff. When people ask me if they should start a company, I don't say no because you don't want to discourage them. You just want to make sure they fully understand that it is a complete lifestyle. Not like a monk, but you have to commit to a certain way of living where you are shutting out many things that normal human people do.

Sam Altman says it's hard to have more than one thing outside of work.

I think a lot of founders make the mistake of, I want to be a founder. Let me look at all these different potential markets and I'm going to figure out which one I can serve. I think that basically never works. I think you have to be bottom up. I think you have to feel the problem yourself and solve a problem for yourself, because then at least you've satisfied a market of one and you know you have product market fit with at least you.

Welcome to Grit. I'm Juvin, partner at Kleiner Perkins, a show where we go beyond the highlight reel and explore the personal and professional challenges of building history-making companies. Today on the show, we have Howard Lerman, founder and CEO of Roam, and previously founder of Yext, which he took public. Howard is the epitome of what I explore in this show, which is the intersection of how he manages his life both personally and professionally very uniquely.

Enjoy.

The cool thing about this show is every week I get to sit down with like somebody that I look up to and somebody that I admire, someone that I think highly of. Now we're whatever, 260 of those, okay? And almost always they like, you know, are very human to me after. They're not like this mythical creature. They, uh, usually if I have an inflated expectation of who they are Generally, nobody can live up to that. Angela was not that. She blew me away. She just blew me away.

I love Angela. I would go visit her when she— my last company was New York, so I'd go visit Angela. I mean, I would go to UPenn. It's one of the few reasons to actually go to Philadelphia is to go see Angela Duckworth and her partner, Adam Grant, too, obviously, is super well known.

Yeah, I've never had Adam on the show.

He's gonna charge you money.

Dang.

Yeah, I mean, I don't know, but that's— Angela's not cheap either if you want her to do like a—

Like a speaking gig?

Like a speaking gig.

Yeah, I've never paid— I've never paid anything.

No, no, I know, I know, but she's, she's 100%.

I mean, as she should be.

She's Angela Duckworth. I agree. And she needs to have some mechanism to, you know, fund the, you know, compensate the work that she's doing.

For sure.

In a way that's proportionate to the value that she's delivering.

For sure. Yeah. Cool. Well, um, thank you for doing this.

Yes.

I'm really looking forward to it. Uh, I don't have like a prepared set of we have to talk about this. I don't have like a ready, set, go. Usually I just start talking. Um, I, um, I was excited to do this, uh, for a few reasons. One, I have known who you are for a while. And I think that you live in this part of my brain of like, had success, acts like he's never had success, and is willing to speak his mind on basically anything. And I like those types of people because they're honest and real. So that was like one reason. The second is the things that you say and the way that you live your life are very unique. And a lot of how you describe your day-to-day is it talks about the intersection of company building and how you run your life. And I am like fascinated by that intersection. That's like most of what I talk about on the show.

Yep.

And I think, um, I have a feeling that in private— you tell me if I'm wrong— when CEOs talk to you, I bet you A lot of what they're talking to you about is how do you fit in the personal stuff into how hard you actually build and work.

It's not just— I mean, Jordana and I were just talking about it.

Yeah. So anyway, I'm thrilled to do it. Um, can I, um, can I start with a post that you, that you articulated? Yes. About your day? I just want to start with your day.

Yes, let's do it. All right.

Can I just read it? I love this post.

All right, this is a—

tell me, uh, this is your morning routine. Wake up, weigh myself. I'm 6'1. I aim to be under 175 each day. My body fat's currently about 12%. I try to cut to 10% for my birthday each year. Put on gym clothes. This is a psychological cue-based trigger. It's easy to put gym clothes on whether or not I'm feeling motivated. Espresso. I fast until 2 PM each day. Set timer for 30 minutes and read something hard. I try to challenge myself with something intellectual. Weight training for 60 minutes right after reading. You do this 6 days a week, and then you lift with a, with a trainer, and then on the 7th day you do a longer run. Work like hell. Very few meetings are scheduled every day. It's mostly IC work. You don't believe in one-on-ones. Generally, you're just jamming back and forth with people all day. Around 2 is your first meal, usually all protein. The ideal is a salmon filet and a bit of steak. Then work more like hell as an IC. 5:30, second workout, cardio. You have an Assault Bike, Concept2 rower, and a treadmill, and you rotate between the 3 of those. Is that right?

Correct.

Uh, back to working like hell until 7:30. Uh, dinner and family time. You have kids?

Yes.

Um, 9:30 back to work until usually midnight or so, and you repeat this 6 days a week. You say no to most things— hugely liberating. I expect everyone to work extremely hard, but not as hard as me. You get 7 hours of sleep per night, total blackout, cool room. You don't track your sleep. As you say, you just, uh, you leave it to God to make it happen. Uh, and I actually thought what was Even more interesting is you found that some of your best ideas come when I'm sleep deprived. If you're stuck on something, you go for a walk or read. Your kids come home at 3, which is when you see them. As you note, 90% of your time will be over by the time your kids are teens. So working remotely allows you to enjoy that part of your life. Alcohol, you've cut. You just don't have time for it. No Netflix. You keep a daily journal where you write a short to-do list. Of any thoughts and insights throughout the day. Uh, you wear the same thing every day. I assume that's the thing that I'm looking at right now.

Correct.

Very Steve Jobsian.

I don't wear jeans.

Still the black turtleneck every day. You have 50 of the same shirt, that shirt.

Correct.

And 20 of the same pants and a bunch of the same socks.

You definitely want to have the same socks because you can Put them all in a giant box and you don't have to worry about matching them up.

Everything is interchangeable. Eliminates decision fatigue when I get dressed. I robotically get dressed. My mind is free to wander on other things. You have 8 pairs of the exact same shoe. Are you wearing the shoes?

Yep. Here they are. When I travel, I can't obviously bring 8 pairs. I rotate around Monday, Tuesday, Wednesday, Thursday, Friday, Saturday, one for each. The 8th is a swap rotation that I kind of use sometimes. I bring 2 when I travel, 2 different pairs, as to not interfere with the wear and tear in the first set. So, this is— I've got R1, which is coded right here for the rotation 1. I have brought with me also R2. I'll swap those every day while I'm traveling, while I'm here. When I'm back, I'll go put them away and then go back to 1 through 8.

8 pairs of shoes.

I also, by the way, I put a Sharpie inside here and then I also Sharpie inside here because it wears off of here. So, I'll put the same coat on. And, by the way, these On Clouds are spectacular.

You love them?

I love them. David Allemann is the founder of On Cloud. He's a Swiss guy. He's got the Swiss engineering. Got to have this little flag right here. But, these shoes are transformative. They're spectacular for sure. That's why I have about 15 pairs of them.

And so you code them differently. Well, let me, let me finish this and then I have— this could take the entire conversation going through this schedule because I'm fascinated. You do this because it keeps them fresher with a week-long recovery period. The 8th pair is for your weekly run.

Correct.

Dining out takes a lot of time and gets old, so I imagine you're not dining out too much.

I don't like when I sit down in a restaurant and then you're there being You're basically beholden to how fast the waiter operates.

Yeah, I feel that.

Yeah. First time dining here, I'm like, okay.

Yeah, exactly. Yeah. Used to have an EA to schedule. Now you just try not to do meetings, and if you do, you schedule them yourself.

I had an EA that would, you know, their job was to schedule meetings and manage my time. And you couldn't really, you know, get on the calendar without going through the EA. And, you know, my calendar, her job, she was awesome, was to manage all the people coming and make sure they got time. And then it turned out that now that I don't have an EA, my calendar is free. If I don't have someone whose job it is to fill up my calendar, I'm not going to have my calendar filled up. And I will schedule meetings, it's just I'm going to do it myself. It's a higher standard.

I respond to everything instantly or never. Inbox zero is irrelevant, but calendar zero is the ultimate ideal. Everyone sings the praises of creatine, but it just makes me hold 2 extra pounds of water. I don't feel any benefit.

Do you take creatine?

No, uh, but I will say it is very trendy. All of my friends are all trying to talk me into it, and I have yet to take anything other than LMNT in the morning. And that's the only thing that I do is have some—

I mean, I can look at you and tell that you're obviously very fitness-focused and, you know, you're— you've got— you look pretty jacked and your skin's really good. I mean, what are— intentionally so.

Yeah. Um, what do I do, you're saying?

Yeah.

Actually, like, not— I don't define it as clearly as you do, but I work out every day. I find— I think I read this somewhere. Was it from Atomic Habits? Basically, it's easier to work out every day than to choose when not to work out. So I just work out every day. Doesn't matter how I'm feeling. I will run. Today's Wednesday, so I ran this morning with my cousin. Every Wednesday.

How far do you run?

To the bridge and back is 7.

And what's your speed in that?

I don't run for speed. I refuse to run for speed. And the reason I refuse to run for speed is because it sucks the joy out of it for me. And running is one of the few things— actually, exercising more broadly is one of the few things that I actually get to enjoy. And so I try not to— I don't measure it. The minute I measure it is the minute I ruin it for myself. And the minute I ruin it for myself is the minute that I start dreading it. And the minute I start dreading it is the minute that I stop doing it. I really try and resist the temptation to measure this one thing. And then Monday mornings I bike Hawk Hill. So I bike over the bridge, up and back.

Yeah.

And then I'll lift. I'll lift twice a week, full body. Everything is compounded. I don't think about what I lift. I just walk in and I just do whatever. If it's back, and then I'll do chest and I'll just make sure I don't stop for an hour. I don't think— I don't want to think about what I'm doing. in terms of weights when I'm there or when I'm going there. I just wanna go and do it.

Yeah.

All I worry about is can I be calorically ahead of the amount of time that I was there? What I mean by that is if I work out for 60 minutes, can I have burned in a HIIT, on the HIIT motion of my Apple Watch, more than 600 calories? And that's my measure for am I moving fast enough? And then I'll do berries one day a week, which is, and then I'll do like lower body. I'll usually play a sport one day a week, basketball. So that's what I do physically. And then no breakfast either. Coffee first thing in the morning. Salad for lunch, like a ritual. Like I haven't not had a salad for lunch in like 7 years. It's like psychotic.

Do you put meat in the salad? Any type of protein?

Yeah, double. Double meat. Good. Double meat. And then I, and then I, I do that.

So that's really like some meat with some lettuce. Exactly. Okay, exactly right. Sometimes when people say salad, they're vegetarian and they're— No, no.

Meat with some lettuce. Well said. And avocado. Um, and then dinner, I eat whatever I want.

Yep.

And I sleep no less than 7 hours a night, similar to you. Um, I do measure it. I have an Eight Sleep. I'd rather— I would give up— I would give up my iPhone for an Android before I gave up my Eight Sleep. I love it.

Um, fortunately, you do not have to do that.

No. I don't have the trade-off, but I would. I would. I love it. Yeah. Does that answer it? No, it does.

I mean, I can immediately look at you and tell that you care about that. And frankly, I think how you present yourself and the first impression that you present yourself makes an incredible impression on the aura of who you are. And it's immediately apparent that you have that. And you can tell Anybody that has that, and anybody can get good at this. And when you think about history, and I love to read about going back, the ancient Greeks and the ancient Romans, the cradle of civilization, places where we had democracy start, places where oration was incredibly important and the ability to speak was how people got started in their careers in front of everybody, and they studied that constantly. Also, there was an emphasis on physical education and not PE in the traditional sense, but being in good shape and being able to move things physically as a champion. And it's actually interesting if you look at some of the shift that we've seen from even founders. I mean, Zuck's walking around with UFC fighter, the fighting. There's a trend towards this. When I started Yext in 2006, in New York, there was not this trend of health and wellness for founders that you see today.

It was frowned upon.

It was frowned upon. It was.

Because you're not dedicating everything to the business.

I would say that it was absolutely frowned upon and you're expected to go get drinks with customers. And so think back to Don Draper in the '60s, the 3-martini lunch was how you closed IBM. Or how you close the big account, you know, the Mad Men style. And Yext was founded in New York, and so there was definitely kind of a lot of that. And fast forward to today, and half the founders I know don't drink anymore. They just don't have time for it, and they don't like the way it makes them feel. But also, it's not the expected outcome anymore. And you see even events today, corporate events focused on health and wellness. You see companies throwing sauna parties to do lead generation instead of doing, you know, long winding dinners that still exist. But there's a new generation of founders, I think, that are absolutely taking this health-focused productivity approach. And, uh, it's, it's a stark contrast to what we saw even as recently as 10 years ago.

Yeah. I mean, look, like there's only so many balls that you can have in the air. And so the N is fixed. of time that you have. And so, uh, you know, I think one of the things that you articulate well is like you're trading exercise for something, whether that's drinking or time with your friends, or it's just like, like, I think, I think Sam Altman says it. I think he said it like basically it's hard to have more than one thing outside of work.

Yeah.

Right. When you're a founder.

Right.

That really matters.

Right.

Now, working out is like, if you do an hour a day, like, that's maybe like 3/4 of a thing, you know, half a thing. Then your family is a thing.

Yep.

Yeah, not that much. Yeah.

That's all you need though. I, I really think you can have one thing. Look, I don't play golf.

What about your friends?

Well, I don't have friends.

No friends.

And so that's the thing you have to cut. You have to cut Friends. Again, I'm not talking about for everybody. I'm talking specifically about for a founder. A founder has so many things that are flying at them from all directions, and they just don't have time for football on Sundays and for social stuff. And I'm not suggesting that that life is for everyone. In fact, when people ask me if they should start a company, I generally say— I don't say no because you don't want to discourage them. You just want to make sure they fully understand that it is a— a complete lifestyle, almost not like a monk, but you have to commit to a certain way of living where you are shutting out many things that normal human people do. And normal human people enjoy going to sporting events and having fun and going out to dinners and barbecuing in the backyard with a bunch of people coming around. And for some reason, none of that ever appealed to me. So it was quite easy for me to cut all those normal things.

Mm-hmm.

And to focus completely on building a company Now, the flip side is, what is the point of a friend? A friend provides you support, they provide you emotional support, or they want to—

And an outlet.

An outlet and social connection. And human connection is the point, is one of the meanings of life. So it's not like when you start a company you have to give that up. You just end up being friends with the people that you're working with. I mean, starting a company and succeeding with people in the trenches is like winning a war together. And you will have a deeper connection with those people that did the impossible task with you over and over and over again against impossible barriers in a way that is the ultimate adventure. And so, you know, if you think of like Star Wars, like it's like they're, they're in the Death Star, they're trying to save the princess and things go pretty badly and everything's going terribly and they're stuck, they're holed up. Luke is there. And Han is there, and they end up in the trash compactor room with the princess. I mean, that was just like a side quest disaster that even getting out of that one little room, you're just right back to where you started with everyone shooting at you. But at the end, that sweet feeling of satisfaction when you've won what you're trying to do brings you that same social connection that you would otherwise get from friends.

So yeah.

cut friends and cut social stuff.

Do you need the second workout? Like the second, the second, the cardio at 5 o'clock?

So a couple things about this. You said you do kind of HIIT for 60 minutes basically, and you keep moving and you're looking at your calorie burn per, per time, 600 per, per hour, which is pretty strong by the way.

Thanks.

Um, what I prefer to do when I do the weight training in the morning is prefer to—

Heavy lifting.

Heavy lifting. That's right. And again, I'm not some crazy heavy lifter guy at all, but I do try to move some actual weight as opposed to focus on moving. And I'm not too worried about, am I sweating a lot during this hour? And I definitely am, but I'm not trying to get that adrenaline pump.

Yep.

Around 5 o'clock every day, I've been sitting, I've been working, I've been at my desk, and I've been, you know, not super mobile. I'm not like running around and walking. I mean, we humans were designed to work the earth, not to sit at a desk, and we tend to end up sitting at a desk all day.

Mm-hmm.

And so, the second pump is really fast and it's at my house. So, like I said, I have an Assault Bike, a Concept2 rower. By the way, the Concept2 rower is absolutely spectacular. And, for a guy, I'm 45, so for every guy in their 40s, there's a joke with some of the people I know that are into this that they get the bug. And so, when you kind of get to your mid-40s, you start to hit the rower. And, the rower is great because it's a workout that is upper body. It really will get your upper body going. Most of the cardio stuff is very lower body focused like the biking and the running, and that's great, but there's something great about a total body workout for cardio, which the Concept2 Rower gets me. So, the other critical part of this is it takes only 15 minutes. And when I say 15, the actual clock time is 7 with 3 minutes of rest. And I'll do 4 by 500, 4 times with a minute of rest in about 1 minute and 40 seconds. So it's less than 7 minutes of clock time on the actual rower, but I am absolutely gassed. It's a sprint when I'm done. And I'm falling over, I'm dripping, and then I just basically get myself together for the next 5, 10 minutes. The adrenaline is rushing. I've probably burned, you know, if you look at the machine, it'll tell you. I think it's 45 per 500. So I probably burn, you know, 180 calories in that very short amount of time. And then I'm back to my desk, good to go.

Uh, do you beat yourself up when you do not follow this strict routine? Because like, life happens.

Yeah.

Things come up, meetings, whatever. There's tons of stuff, family emergencies. If you miss a workout in a day, if you do not eat the meal that you expected to eat, if you have a breakfast meeting and it's rude to not eat breakfast at that meeting, if your kids say, Dad, can we have some waffles together? All these things happen. Do you beat yourself up?

Well, I'm not going to have waffles in the morning because that just is going to slow me down. The thing about eating breakfast is that I think breakfast is— The food industry has built it up into breakfast is the most important meal of the day. We're going to get Cheerios. And I mean, cereal is absolutely the worst for you. You might as well just eat candy in the morning. But for me, when I eat, I don't feel as good. I'm just not as productive. Eating slows me down. And so I wait as long as possible to try to put something into me. And frankly, there are many days, even though I say fast till 2, there are plenty of times where I'll just fast the whole day until the evening. So I'm perfectly comfortable doing that. In fact, the more I do, the more I do. And so if I put food in me, that will actually slow me down. But back to your question about whether I'm going to be beating myself up, I actually don't feel as good if I don't work out. So I don't beat myself up emotionally like, oh, you're really off track today, Howard. You screwed up. But I actually— my body just, it's like expecting to get that sort of that kick. And if it doesn't, if I don't get it, then it's gonna, it's gonna physically tell me, hey, you know, you, you, you know, what about me?

Yeah, but what if— okay, let me just give you another example. What if you forgot the— what if you forgot your pair of shoes? What if you like, for like this trip or whatever, you brought the wrong pair?

Yeah.

Or like, I, I forgot all of my running shoes for my trip last week. But then what?

That would never happen.

Then what?

Then what? Never. There would be hell to pay. No, uh, I would be totally fine with that. I mean, traveling—

And then what, you don't work out?

I would go buy a pair of shoes.

Okay.

It would— I would literally go and I would be mad at myself and I would just walk down to buy a pair of On Cloud Runner. I mean, they're in every store. And if I couldn't find that, I'd buy a Nike pair and I would just spend the time and I would, I would, I would fix the routine. It's hard to keep it up when you're traveling because you can't have everything sort of set up in the same way. And I do travel quite a bit, but that's just part of being a founder and being an executive. So this routine works particularly well when you're not traveling, but it also can work really well when you are.

Are you married still?

Yes.

Yes. You're not wearing your wedding ring, I noticed.

I don't wear any jewelry or anything at all. I've never worn a watch. I've never worn a wedding ring. Ever?

Ever.

Nope.

How old were you when you got married?

I was very young. And I'm actually reminded of your insight, which you discussed with Angela Duckworth on this. I was fortunate enough— well, let me actually take a step back here. So the luckiest thing in my life besides meeting my wife when I was 20 was having been born in Northern Virginia, where In Northern Virginia, they had this magnet high school called Thomas Jefferson High School for Science and Technology, TJ as it's widely known. And I got in. I always had loved computers and I'd sort of figured out that this was a place where there might be other people that loved it. And so I applied and got into TJ.

Isn't it the top high school in the country?

According to various things, it is definitely the top. I personally believe it's the top high school in the country. They've changed some stuff recently, but they're bringing it back. But there's actually been a number of successful founders out of there. Vlad went there, Tenev from Robinhood. And the thing about TJ was you couldn't influence your way in. You can influence your way into Harvard. You totally can. You can influence your way into Duke. You totally can. You can influence your way into many private high schools. But with TJ, it was literally that you took a math test and then they cut it off at the top 400, and then that was who got in. And as a consequence of that, it self-selected the people that were into that in the first place. And then the people that were there were actually hardcore. And I saw a post from a fellow TJ founder yesterday who said something to the effect of, the people that I worked with in high school were smarter and more hardcore than the people that I knew at Stanford, for example.

Sophia?

Yeah. You saw that post too?

Yeah. We led the seed.

That's funny. She's TJ, TJ Grab. So I've never met her, but she went to TJ and I saw that and I was like, that's totally— I totally agree with that. That's how I felt too. I went to Duke and back to your question, that's where I met Wendy. And, you know, I met my wife when I was 20, but I was sort of an odd duck. It was—

Was?

And, um, at least I'm more self-aware of it now.

Hey, no knock on odd ducks.

I'm an odd duck. I get it. I, I think, you know, when I was growing up, I wasn't— I, I loved baseball. I always wanted to play sports, but it turned out that I wasn't very good at them. But what I was good at was not necessarily what I wanted to do, but my mom sort of forced me to do it anyway, and that was singing opera. So I was a child opera singer, and every day my mom used to pick me up from baseball practice in the middle of the practice in front of all the boys. You can imagine how this looked in front of a bunch of 10-year-old, 9-year-old boys who thought that opera was, you know, not the most masculine thing in the world. And I had to leave for opera practice every day and get driven down to The Kennedy Center, because I grew up in the DC area, where I was in world productions of operas with Plácido Domingo. And he would be playing Rodolfo in La Bohème, and I would play a children's role because they have children's roles in these productions. Actually, I forgot about this, but when I was 10 or 11, the Bolshoi Opera from Russia, right before the the fall, right before the coup, came to America and performed for the first time. And they brought me and my brother in.

Come on.

Because they needed 2 American kids to fill the roles. And so we were down there with all these Russians and there was all this security everywhere. It was crazy. I mean, I remember it was covered widely in the press. The Bolshoi Opera has appeared here. And they did 2 Russian operas. And I have to say, I was pretty good at the Italian operas. We were in La Bohème and Manon, the Puccini stuff and the Verdi stuff, we crushed. This Bolshoi Opera that they had us go in when I was 10, the sequence of stuff that they had us doing in the music, I think I screwed the whole thing up. I think I fucked up the Bolshoi Opera basically. Because they gave us these dolls. I remember they handed us these dolls and I had to throw the doll up 10 times and catch it and pass it off. It's just, I think it— anyway, I had to leave baseball practice to go do this kind of stuff every day. And as, you know, a half-Jewish fat kid from a red state that grew up singing opera, I was, you know, teased a lot. So I got really used to just like not giving a shit what anybody thinks and just proceeding in what I believe intuitively to be the correct thing.

Hmm.

And intuition has, for me, guided my life. I have just very strong intuitions about stuff and it's like quick, that gut feeling that happens right away. And I just know when something should be the case. And I think that's why I decided to be an entrepreneur because first off, I didn't decide to be an entrepreneur. It wasn't like I was like, ah, there's a career entrepreneur, I'm going to do it. I just started. I just started when I was 19, when I was 20. I started my first company and I sold it then. It was called Just a Tip and it grew to be pretty big. And Jon Stewart sent a tip on The Daily Show when I was just a freshman in college and it took off and went viral. And I had founded it with a couple of guys from TJ. And the thing about this was like, I just— when it comes to starting companies, there's not like an active decision process for me. It's, it's totally guttural. Like, I just know I see something that the world needs. I decide that I'm the best person in the world to, to solve this problem with an amazing team around me. And I assemble people that are way smarter and better than me and more skilled in various areas. And then we just go and we just do it. And it's a very guttural, intuitive kind of thing. But I just, when that feeling strikes, I just, it's going to happen. Like, I'm going to make it happen. And there's going to be, you know, rooms along, trash compactor disaster rooms along the way, but we will get out of it and we're going to get out of it together. And it's going to feel awesome when we do. And we're going to solve the problem and save the princess.

When you met your wife, you're 20 years old?

Yep.

Were you like this? No.

I was, let's see, in college, when I first got to Duke, I didn't really fit in because TJ had conditioned me that everyone cared about math and science and STEM. And I thought that was just going to be like, Duke would've been the next extension of that. But it turned out that people were like, what do you They didn't know about computer science. There's a great computer science department at Duke who I ended up knowing very well, but the majority of people were not like that. They cared about other things. And so the idea of sorority life and fraternity life had no appeal to me whatsoever. I have major issues with authority. All the other freshman kids would rush the fraternity to try to get in, and the fraternity would make them do all this stupid shit to you know, go through the hazing process and whatever. And like, that's fine. Like, people can do that if they want to. I couldn't have like held that in a lower regard. And so I was like one of the only people that like did not rush a fraternity, did not go through that whole Greek life thing. Um, so maybe that made me sort of like sidelined, I guess.

Mm-hmm.

But I did end up joining an a cappella group, and that was pretty awesome. And that's actually how I met Wendy. at an a cappella concert because I, we, um, we put on this great, this great concert and I, I met her, I met her when she was, she was 19 and I was 20.

So. Yext is probably your biggest company so far. Is that fair to say?

So far.

So far.

Yes.

Uh, you probably made, I'm just guessing, a couple hundred million dollars. Just guessing. I have no idea. It's about a billion-dollar company today.

Yep.

You owned a bunch of it.

Yep.

Like, you made a bunch of money. Life-changing.

Plenty. Yeah. Did—

okay, so like from 20 years old to Yext was about 12, 15 years when you started it. When did this metamorphosis happen? If it didn't happen when you had met Wendy, when did you go— the way I would describe it is like Spencer Skates from Amplitude. was telling me a story on the show about how basically he wrote down like, what does an ideal founder look like?

Yeah.

And then he basically was like, I'm going to choose to be that person and everything that that means. And in many ways, like your metamorphosis kind of reminds me of how he views what he did. And I'm just curious, like, what changed? Was it money? Like, did it happen after Yext where money afforded this? Um, yeah, what, what happened?

I think so. It's interesting. So the way Spencer talks about this, he's kind of doing some top-down thinking. I'm not a top-down— I actually used to be a top-down thinker. I used to say, and I think a lot of founders make the mistake of, I want to be a founder, Let me look at all these different potential markets and I'm going to figure out which one I can serve. And I think that basically never works. I think you have to be bottom-up. I think you have to feel the problem yourself and solve a problem for yourself, because then at least you've satisfied a market of one and you know you have product-market fit with at least you. And so it's just, it gets you closer And I've gotten recently into this kind of empiricism versus rationalism thinking. I used to be much more rational. I'd be in my own head and I'd be trying to figure stuff out without actually doing it. And then it turns out that doing stuff is the best way to learn. And being there and doing things with your hands. There's a great quote from TR on this about, do what you can with what's in front of you with your hands, with what you can do right now, Teddy Roosevelt. And that, I never really understood that until I started like doing stuff with my hands and started to, get out of my own rational planning and decision-making and trying to strategize about how everything's going to go and plan it all out and actually do stuff. And so I don't think I'd ever start from what are the attributes of a great founder and work backwards to try to meet those things. I will just do what I think is right. And it gets back to that kind of guttural intuition about myself. I have a very different approach from Spencer in that regard.

When did you go full— did it happen over time where the list that I just described of your day, did your pieces of your day start to come together?

Yes.

And then now it's a full day?

I think it is a continuous pro— and by the way, the day, the current iteration that you see is the current iteration. It's going to be continuously optimized and improved. I once— was it a Google zeitgeist? Nikesh gave a book out. About the click moment. And that's when I decided that every day I'm going to wake up, the first thing I'm going to do is put my gym shorts on. And it's just because it's a trigger to make you— when they're on, you work out. And so that was something I learned. And a quote that lives rent-free in my head is Charlie Munger about being able to— the smartest people are learning machines and you can get smarter at getting smarter. So you don't just get smarter, you can increase your rate of learning. And for me, being able to just have this kind of disciplined routine that I can continuously optimize is— it started, I would say, when— let's see. Well, I've been wearing these Lands' End turtlenecks for—

That's what it is, Lands' End?

This is a $20 Lands' End turtleneck. And they know me now, and they send me sweet Christmas cards and stuff like that in the mail. But this is a $20 Lanza turtleneck. I've been wearing these probably for almost 20 years, I would say.

Since Yext?

Oh, yes. Oh, yes. I mean, if you look back at all the Yext pictures and stuff in our IPO day. I mean, this has been what I have worn always. And I also think, by the way, and this is a crazy thing I'll tell you about, I think what you wear is hugely important. And it's funny, the fashion industry fundamentally understands that, right? Actually, you were talking about your favorite movie with Angela and—

Devil Wears Prada.

Devil Wears Prada with Like that color blue. And I don't remember the scene. Yeah, I don't remember. I don't really know that movie very well, but I did remember the story of like, well, somebody chose that for you. And I think a lot of people, when you put on the gym shorts, it's like, I am now ready to work out. And when I put on this turtleneck, it's like, I am now ready to build something awesome. And so for me, it's just simply a wardrobe choice That is putting me in the correct mindset to do something. When I take it off, like put on like a sleep shirt, okay, it's like ready to go to bed or whatever that is. And so I think you can do these little cues that condition your mind in a way that get you ready to do whatever it is you're going to do. Like before I would go on TV, I'd have a routine. It's like an athlete. They all have these little routines that they run to be able to be successful. Now you can get into the alter ego stuff, right? I think, who is it that does the alter ego?

Elizabeth Holmes?

No. Well, I don't know much about her at all, but I think, is it Beyoncé that had an alter ego that would jump into a different person? And she assumes a different name in her own mind when she's trying to be who she is. I don't do any of that kind of stuff. This is who I am. But there was no single moment. It's been just a process of continual evolution and trying to be the best I possibly can be. And by the way, I do look at the clocks because what gives me joy is actually not trying to improve upon my old scores, but just not get any worse. Because at 45, you stop pushing it because when you push it, that's when you get hurt. And my job is to basically maintain at this point.

Yeah. I mean, even, even for me, I'm still, I still worry about pushing it, uh, because I get injured every time.

You gotta be careful in basketball. Basketball. I know so many guys.

Even lifting weights though. Like if I try and push to a heavier, it doesn't matter.

And it doesn't, and by the way, that one's not in your control. Some other, somebody else that had a bad day and they're angry. That's true. Yeah.

Um, does your wife think you're nuts?

Yes.

How old are your kids?

8 and 10.

Does your wife take your edge off? Does your edge come off?

I don't think so.

So how we are talking right now is exactly how you would be right before you went to bed?

No, I, I— she, um, I think maybe—

can I reframe it? Everything you do is in service to performance, and your version of performance is company building.

Yes.

How does that make her feel? I don't know how else to ask.

Like, I guess I probably should ask her sometime. Uh, no, I think she knows what she signed up for in a lot of ways.

But you haven't been this way forever.

Well, I will also point out that having Met her when I was 20 and she was 19. We grew up together. And I think a lot of problems today is that people— I want my kids to get married young. Like, I tell them that all the time. They're 10 and they're 8, and I tell them to get married young and have kids young. And there's a lot of pressure and a lot of advice out there that say, hey, you know, go out there, forget trying to get married, forget having kids and a family. Go out and build your career for as long as you can. Move to New York and go work. And then when you're in your 30s, then you can focus on that kind of thing. And I think that advice is fundamentally— I think people can focus on their careers, but they don't have to do it at the expense of having a family and getting married young. Because when you get married or find your partner very young, you are able to grow together. And so she's not like me in any way like this at all. But she's been there through the entire metamorphosis and entire growth period. And so she knows exactly how the whole thing works, and we know each other so well that it's not the kind of thing where I have to ask her, is she okay that I'm now coating my shoes? She thinks it's funny. And she's like, you need— In fact, We tried the shoe coating thing. I started the shoe coating thing about 2 years ago, and for a while, I was struggling to find a pen that would not wear off. And so finally, she's like, you got to use this Sharpie. So now she leaves a Sharpie in my closet, and it's a silver Sharpie because it's going to be black shoes. And so she's a partner in crime to my—

She's an enabler.

She's a total enabler. She's handing me the Sharpie. Right? And she knows, she knows, she kind of, she might roll her eyes about it, but she thinks it's funny.

Do you want your kids to be this way?

I want my kids to be whatever they want. I don't want to pers— I'm not like Naval.

You don't care.

Naval is like, I don't want my kids to go to school.

Right.

Right? And I think that's like, what is he talking about?

Yeah.

Like, I, I'm, I'm, I want my kids to go to school. I want my kids to go to good schools. I want them to study. I, I'm, I make them do math in the morning when they wake up. And that said, I want them to understand. So the best thing I can do for my kids is to set a good example as opposed to force them to do stuff. So when they see me reading, I wake up and— do you have kids?

Not yet. I'm engaged, so I got to get married and then have kids.

Yeah. So when I sit down and they see me, when I wake up in the morning, they come downstairs, I'm reading. Usually, that's my 30 minutes of reading. And we talked a lot about the health, the macros and the calories and all that kind of stuff, but I actually really make it a point to read something very hard every day for 30 minutes that has nothing to do with— I read The NVIDIA Way and I'll read books on business stuff, but I also will go way outside and I try to put into my mind the greatest works that of mankind, things like Ivanhoe from Scotland or The Leopard, a fictional novel from Sicily that try to bring you closer to humanity in a way that let you then take that art because you said, my company building is— the best way I can describe it, my company building is my art. And for me, waking up, it's not work. I literally wake up and I get to— it's weird because when people hear about this routine and they hear about the work, they think, oh, he must be miserable. Oh, it must be the case that you don't go to barbecues and drink beer and watch football. That's the point of— what are you doing, man? How can you not do that? I just don't find that enjoyable, but that's not the point. The point is what I do each day, I find incredibly enjoyable. I literally tap danced into here to hang out with you today for this talk. I'm going to tap dance back. I'm going to open my laptop. I'll be right back into my— virtual office. I have the best people working on the coolest new features. I mean, if you saw the thing that I was— that we shipped literally last night that we announced this morning, it's one of the coolest features we've ever made. On your lock screen, you can see all the people in the company and it's rotating around. It's kind of like the Eye of Sauron and it shows you— and the icon is an eye. And I literally worked for 2 weeks with our designer on getting that exact interaction. Precisely correct in the way that felt really good to all of us. And to be able to bring that to the world today is an extraordinary luxury. And now to have all these people anywhere being able to use it. So, you know, I heard Angela talking about this. It is absolutely not inconsistent to have a regimented daily routine and to have joy. And I have extraordinary joy in the routine and frankly not having to stand around at a football game or have to worry about what shirt to put on because I would definitely get it wrong are liberators of joy for me as much as other types of things are.

And if a family member or a friend from middle school If somebody does not have value to you work-wise, will you spend time with them?

Well, yesterday, my old friend, actually a friend from middle school, emailed me. He's in Dubai. He's the CFO of Turing right now, Johnny's company. And Alok Bhushan is my good friend from middle school, by the way. We went to the same middle school and he went to TJ.

Mm-hmm.

And he worked with me at Yext for many years, and he emailed me. He's like, hey, I'm in San Francisco for the week. Let me know if you happen to be here too. And I did, and we went on a long walk, and that had nothing to do with work. I mean, we were reminiscing about our middle school math teacher, Mr. Williams, who was the best math teacher and taught pretty advanced geometry concepts to 7th graders, which was super cool, and we were blessed to have had him. And that's an example yesterday of just doing that. So that said, I'm going to say no to a lot of stuff too.

Yeah.

You have to. You have to say no all the time. And by the way, not just in people reaching out to you, but in product choices, in hiring choices. This firm, how many nos does a VC give out? VCs basically say no all the time. And it's tough to say no, but it's also how you create your artwork. You have to whittle things away until you get to something substantive.

Did money change anything for you?

I would say that money gave me the right to say whatever the fuck I want. And actually, probably also not running a public company helps with that too. So when you're running a public company, you have to really, you know, you put any statement through legal because you don't want to say anything that could be construed in a way that you could get sued for later. So now you look at some people on the other side of the spectrum here, they say whatever they want anyway, and they get away with saying whatever they want. Like Elon runs big companies and he does not hold back from what he thinks. And so When I take Roam public someday, and we will, I'm going to not change who I am. But my big— I don't want to say it's a mistake, but look, I was running Yext and I tried really hard to fit the mold in a way of what I thought Wall Street would've wanted.

Hmm.

And this time around, this is my second time around, I'm not going to do that. We're going to be who we're going to be, and I'm going to say what we're going to say. But the scope of what I talk about is stuff that I know about too. It's not like I— I actually have a rule. I don't tweet about politics. I don't talk about politics. That's just not my area of expertise at all. I know a lot about productivity. I know a lot about meetings. I know a lot about how to not have meetings, how to eliminate meetings, how to run effective meetings, how to run a company. And so these are the things that I'm going to share my opinions on, and sometimes people aren't going to like them, and I'm going to be okay with that. When I was running Yext and running a public company, I was more concerned with making sure everyone was not having their feelings hurt, at least externally. And so I won't do that the second time around as we build Roam into what we believe it can possibly be.

Did making money feel as good as you hoped it would?

It gives you a degree of freedom. I would say that there's a certain level at which you can feel that freedom too, and making money beyond that level does not materially change anything at all.

What do you think that level is?

Ooh, I think it depends on the person. Depends on the person a lot. What's the level for you? I think probably, I would say $20 million.

Why? What does $20 million get you?

Well, I live in Miami, So it's a little bit more, the cost of living there is higher than say Virginia where I grew up. And by the way, I went to public schools my whole life. I didn't grow up with money at all. So I think the thing that, and again, that's just a number. I haven't put a lot of thought into that. I think that that's enough where you can basically maintain a million-dollar-a-year lifestyle basically in that range if you're not dumb with your money. Which after taxes and you pay all that out, then that seems like that's probably enough for most people to go on. That's kind of a number where— and again, I haven't put a lot of thought into this, I'm speaking off the cuff— but $1 million a year before taxes in income is kind of enough where you don't have to have a job and you can do whatever you want. And you can do that really enough with you know, with family and live like a pretty high-end lifestyle. So what's interesting is I have this sort of stoic routine, but I also, I like to do cool things. And for me, the point of the money isn't necessarily for me to be able to like buy artwork. Like I don't give a shit about that stuff at all. Like, yes, I have a nice house and yes, I, you know, drive a nice car and like I care about that because I think that stuff is awesome. But the main thing that money does is it lets me make more companies and more art. And everything I have is devoted to trying to make Roam what I believe it can be, which is this incredible virtual office and an entire ecosystem. And I am totally committed to making that happen in an awesome way. And having money and being able to raise money from venture capitalists basically lets you hire incredible people because that's the main— I guess compute would be the other main investment people make. We're not making some fundamental investment in compute, but it lets me hire the best people I know. And get them to go on this shared mission of building the virtual office that powers the world's work.

What cool stuff do you do with the money besides put it in your own companies?

Well, I will tell you this. I think that money can be a double-edged sword for second-time founders because the first thing I did when I— the first company I started after I stepped back from Yext, which by the way, that was after 15 and a half years and I did everything I possibly could there, I started a music company and it was only out of passion for music. It was called— it was really cool. It was called Dynascore, like dynamic score. And you would upload a video and it would use AI to generate a score that exactly matched the sort of key points in the video. And it would re-scramble existing classical music, for example. So like, let's say you had a 17-second commercial you wanted or video you wanted to put out there. Hmm. And you wanted Mozart's Eine kleine Nachtmusik in the back of it. Well, Eine kleine is not 17 seconds. It's 3.5 minutes. And so how do you exactly splice? Usually you'd have to get an audio engineer to splice something to match that, but Dynascore let you upload the video and put sort of key inflection points of where you wanted to, like the scene changed or where you wanted the music to emphasize, and it would give you a 17-second version of Eine kleine. It was really cool. It turns out that there's no money in that product at all. Yet I put a lot of money into building the product in a way that was not economically rational. And I bought, paid for incredible design and great logo and UX and all this music. And we went deep into— there's this German company called Native Instruments. You've probably never heard of them, but they actually make all of the instrument sounds that people use everywhere and in their videos and stuff. Are you smiling because you know?

No, I just— this is an insane story.

Yeah. And so I went and we cut this licensing deal with this little company in Germany that makes all the best drum beats and all the best synth sounds so that we could use their sounds. And I was unwilling to use AI to train on the existing corpus of music. And this is where I think I was not willing to basically steal other people's music, whereas you see some of these things out there that are trained on Sony Records' music. They sound awesome, but they're literally trained illegally. And I was not willing to take that step. And so we sort of had a different approach. And as a consequence of that and a consequence of the product, I basically had— it was too much of a funhouse. It was like I was able to afford this, fund this crazy project, but it was not rooted in economic reality.

Because it didn't need to be.

It didn't need to be. There was no product-market fit, or it wasn't very strong. And I learned a lot from doing that. It was a big mistake. I shouldn't have funded it at the level I did. I shouldn't have tried to make it perfect. I should have I also waited too long to put it out in terms of like, no, we have to have this and this and this. And so it just, I ended up building something for something expensive for something nobody wanted. And this was right after I left Yext and it was a big mistake. Fortunately, Roam came out of that because we actually hacked up Roam as a way to stay together while we were building Dynatrace. And it turned out that we're back to the, oh, well, let's make something for ourselves that we love to use. Like, I wasn't making videos with music. This was a product for Adobe videographers. It was a Premiere Pro plugin. And it's funny because I talked to Marc Benioff about this and he said the same. He actually said a lot of second-time founders, he said, you should raise outside capital for your next company, even though you can fund it yourself, because you don't want to turn the company into a funhouse. Which is exactly what Dinosaur was. And so that's why when we started to build Roam, and we started to see traction there, that's where I had thought, well, should I just bootstrap this thing? It's not bootstrap because bootstrap implies you don't really need to put stuff in, but I could have funded the whole thing.

You put $10 million in?

A bit more.

Yeah. Okay.

A bit more. So I did put plenty in, but I also intentionally brought in an outside partner because I wanted them to keep me honest, and I wanted to make sure that I was playing by the same principles of the universe.

Right. That rational actors would—

That rational actors played by.

Yeah. Super interesting.

Yeah. So that was an intentional choice.

You ran Yext for 15 and a half years. How long was it private for?

We were founded in 2006. We went public in 2017, 11 years, 10 and a half years from founding to IPO.

And how long were you at the helm as a public company?

22 earnings calls, 22 quarters. Public company CEOs will always answer it in terms of quarters.

So yeah. Is the story out on how and why you left?

There's no story.

It was just time.

I did everything I could. I took it to almost half a billion of recurring revenue, which I know today doesn't sound that big, but this was high-margin SaaS revenue. From hard customers, we sold into McDonald's and AllianceBernstein, and we had big enterprises around the world, non-tech companies, legacy businesses. And this idea of business listings, this idea of— it's such a simple idea of when you look up a business on Google Maps or Apple Maps, where does the data come from? And being able to centrally control that, And so that you could go to McDonald's and let them have a knowledge graph system to be able to update the phone number of one of their branch locations and have it instantly update in 100 different places so that people always find the right information was a very simple but extremely hard idea to implement. And there's a whole story of how we broke the chicken and the egg there and finally got Google to open up their index and let us update Google Maps for Apple Maps. Remember how bad Apple Maps was when it first started?

Yeah.

The location data problem is a huge problem. And it remains a huge problem. And by the way, all the new AI search tools, there's all these AI visibility tools that I see every day coming out. They don't actually do anything. They tell you how you rank in AI search. And this was something at Yext. And again, I'm not running Yext anymore, so I can't speak to their product roadmap. But when I ran the company, it was easy to show you your problem. Like, your phone number is wrong in Google, your address is wrong in Apple Maps. That's all they were doing. But I would always say that that was not enough. I wanted to be able to fix the problem. I wanted to be able to, like, thank you for showing me that I have the wrong phone number. Now what do I do about it?

Well, I don't know.

And so these new AI visibility tools, which are sort of growing up in the same market, in the same space, are showing you Your problems. And yes, they're saying, well, there's some suggested solution. The suggested solution's always the same. It's to write a blog about content and have a top 10 list. It's the same old SEO trick. It's like the same old SEO tricks of working in AEO or whatever people want to call it these days. It's literally like you have to make a page on your domain and then take the top 10 competitors that you want to talk about and put them on the page and then get people to link to it. That's just There's really just not a whole lot to it. I look forward to a company like Yext. I'm not saying they can or will do this, but you would suspect they might want to be able to actually update ChatGPT's maps. And ChatGPT doesn't have maps yet, but considering they just launched a browser yesterday, you would think that they are going to be able, they must be thinking about this thing, or they're going to have to partner with some open source map. They will have a consumer app.

Yeah.

Perplexity will have a map. All these AI search, it's funny, the whole idea of Yext was that search was always going to be changing. There's going to be new players involved. It would actually be really— and Mike's a great CEO, their CEO that's there now. He has tremendous product vision. He has tremendous sales abilities. And it's a super exciting time for that company actually. I don't regret leaving. I did everything I could. to build the company and to pass the torch to a guy that I felt like could operate at the scale that we wanted to. But at the same time, this is a really exciting time for that space. These little things that are bubbling up, they're showing you your problem, but they're not correcting it. Yext has, I don't know the number, but probably 5 to 10 million authoritative businesses using the product. And so for an application like ChatGPT that wants to make their own app, The value prop is like, we're going to be able to give you authoritative real-time data for free. Like, we don't charge you for this on the 10 million businesses people give a shit about in the world. Here it is, take it, put it in your maps. That's it. So it would be exciting to run the company. It's probably an exciting time for them right now.

Maybe they'll buy you and you can do a Steve Jobs back.

Well, it would cost them. So the answer to that is maybe we'll buy them. Because I think Roam is going to be way bigger than Yext ever was. The opportunity to build a virtual office, the TAM is infinite, which is good and bad because it's like, well, who are you going after? But the product, Roam— so Yext was really hard to build because it was hard to get critical mass to be able to get Apple Maps to— you can't just call up Tim Cook and say, hey, we want to update Siri.

Right, right.

Like, like that takes, that takes a lot of business development, not just relationships, but actual leverage. You have to have leverage. And Yext has the oil, which is the data in, in, you know, in, in the, in this world. And so that was really hard from a data perspective. Rome was a very different challenge. Rome was very challenging technically. And in starting Roam, I totally fucked up. I completely underestimated how hard it would be to rebuild video conferencing. There's a joke now that when you watch the old Star Trek films, the most unrealistic technology in all of Star Trek is how fast the video conferencing is across galaxies and reliable it is. And I thought video conferencing would be the kind of thing that you could just get from a third party. Like turn it on from Amazon Chime or something like that. It turns out you cannot. And that, by the way, is why Zoom still is dominant to this very day in their— they have the best— Eric figured it out. They have the best video conferencing and they still do, and they still do at scale. And Teams and others have caught up. Google Meet's pretty good now. Google Meet's really good, but only for 10 people or less.

Mm-hmm.

Like try to get 48 people or 75 people or 150 people or Let alone thousands, it doesn't work as well. And we ended up building— speaking of side quests, we ended up in that trash compactor room for a year building video conferencing software. So I went out, we launched it, and it turned out that video conferencing was really hard. And by the way, people have such a high standard for it today that if you don't do a good job on it, you're in trouble. Yeah. So we went out there and we built all of our own video conferencing stack, our own SFU, everything bespoke. And that was an 18-month side quest and continues to be a side quest. And so Roam, while Yext was very difficult to break the chicken and the egg from the data perspective, Roam, the technology was way harder to build.

Mm-hmm.

And there's way, way, way, way, way more engineering that's gone into video conferencing and chat and the virtual office map and MagicCast, which is our— by the way, we support all these different platforms. So UX is a web app basically syncing across Apple and Google and Amazon and Meta, all their assets. Roam, we've got a Linux app, we have an iOS app, we have Android, we have web, we have Windows, we have every version of Windows going back. We have to support all the Mac stuff. And every time a new operating system comes out, because we're a desktop app, that sits on your desktop all day. Uh, you know, Mac Tahoe just came out and 10,000 bug reports show up because they changed the way a little bit how screen sharing works. And that's just like a whole situation to kind of go after. So this one has been much, much more of a technical challenge, but it's an exciting technical challenge. And, and I, and I, and, and the reason that this should exist in the world is, is it should not, not exist because the technology can't make it happen.

How big is the company?

We are about $2.5 million of ARR. We are actually, and I'm building in public, so I'm very comfortable talking about anything. We will, we're on, I know it's not cool to triple, triple, double, double anymore, but that's the path we're on, probably a little faster than that. But that's okay. That's competition for VC dollars much more than customers. I don't hear a lot of customers coming to us Saying why aren't you tripling? Why didn't you triple, triple, double, double? In fact, our customers are global. We have 30% of our customers are in not the United States, and we have super high net retention, and that's what I care about. And we want to grow because all healthy businesses grow, but they're not too concerned about our growth rates. They care about the fact that we just launched our watch feature this morning, and they're all fired up about that. And that's what gets me going is when I hear feedback immediately that people are like, this is freaking cool. And then you're in your CarPlay now driving around and you can glance down and see who's meeting with who in the virtual office and it rotates around and shows you. And that's just the kind of stuff that gets me going.

How many people?

We are 27 people. And the cool thing is I'm pretty sure we're going to be able to get to, as a public company CEO, I'd never throw this out there, but I don't care about that anymore. So I'm pretty sure we can get to $10 million of ARR. next year without hiring too many more people. I think it's going to be basically 27 still.

You think it's 27?

I think we'll hire a few.

Why? Because of the LLMs?

No, because of the 27, 24 of the people are design and engineering. We don't have any salespeople. And so I can just see the inbound demand that's happening and do the math on the compounding.

Yeah, but you're also getting more out of each engineer with these tools.

I see what you're asking. You're saying the engineering productivity, not the sales productivity?

Yeah, just in general, wouldn't you otherwise need to add more designers and engineers?

Well, one thing about adding new designers is it doesn't really work like that. If I added a second and third and fourth designer, I think we'd get probably one quarter of what we get right now. So design is kind of a weird one where you hire a couple of really good people and they can take you— how many designers did Apple have, for example? It's not a huge number. So you can get a lot of economy of scale. Actually, one of my favorite books is an old Disney book, and I have it sitting on my— it's called 13 Old Men. It's about the 13 original animators. It's actually hard to get this book. I had to wait a year, and it's not in print. 13 Old Men, and it's about the Disney animators and 13 guys that made every Disney film. Entrepreneurs in the Valley look up to Jobs and to Elon. My idol is Walt Disney. Maybe that's because I live in Florida and Orlando is right there. But if you really want to see magic and craftsmanship and art, go look at the fonts in the cash registers in Star Wars World at Disney. They've changed even the way the font works when it On the credit card processor when it says like, thank you, like that's the level of detailed craftsmanship. They call it Imagineering. And so I look at that, our Roam team, we do everything our own way. We don't have support people, we have Roamgineers. We don't have engineers actually, we have inventors. And we spell inventors with it, with the exclamation point that points to, you know, to point to spell it differently. We, we do things our own way. And our engineering productivity is, we don't need to hire tons of engineers to maintain and continue to expand the product that we have today. And 13 Old Men is kind of the idea that these 13 animators who were brilliant and did all the films that we all know, Snow White, Cinderella, all the famous ones for that kind of era of Disney from the '30s to the '60s, was basically made by 13 people. And then all the marketing happened to promote it out, to make it global. But that book is a really great book. And there was a couple of guys that just made all that stuff.

Do you ever need a— do you not need outlets from this all? Going back to the friends, beers, You know, you don't watch shows. Like, do you not need— like, I have a hard time believing that you don't need an outlet somewhere. And I, I don't know, when I say outlet, outlet does not— not something physical.

Mm-hmm.

Not exercise.

I think I've conditioned myself. I, I do think exercise is an outlet for sure, but my family is a great outlet. I also want to point out that, you know, we haven't talked a ton about this, but My kids, I see them all the time. And being able to work from Rome means that I get to see them when they come home at 3 o'clock and I get to hang out with them. And you'll understand that when you have kids, you're going to want to be around them. And I want to be present with them and just catching them right after they get home from school for even 10, 15 minutes. They're all excited. They just had school. You get to kind of— they're in a great mood. And they're through the high of the day. So I think my outlet is that. And my outlet is watching my daughter. She's a great singer. I was a decent opera singer. She is really good. And so my outlet, this summer, here's an outlet for you. We went to Austria and we shot a music video with her. And I don't know if you've ever seen Sound of Music. But I love Sound of Music. It's my favorite. I love Broadway musicals. And actually, maybe my outlet is, is we, we at Rome have done events where we bring in Broadway singers. Like, we'll do karaoke, but we have professional singers like in the room with you. It's actually really fun. And they'll do Wicked and they'll do Hamilton and all the cool like Broadway shows. And, and so my favorite was always Sound of Music. And, you know, they have the do, re, mi and all the classic favorite thing songs. And we bought my daughter, who's the singer, she had written a song, we composed it, we went to the studio, recorded it, and then we went to the hills of Austria where those famous scenes were shot.

Yeah.

Bought her a Dirndl, which is the traditional German outfit that Julie Andrews was wearing when they shot Sound of Music, and shot a music video, and it's on Spotify. And that's an outlet for me.

What are your vices then?

Probably music. I mean, I don't mean to sound like a virtuous monk or something like that.

Do you eat dessert?

Yeah, I will. By the way, all the things, the routine is not— first off, When I come to San Francisco, the first thing I did when I landed, I went to House of Nanking and I had some dumplings, man. They were great. And I'm sitting there, and by the way, I probably ate 4,000. I don't care. I'm like, you eat whatever you want for dinner.

Yeah.

I don't care. I'm good. And yes, I had a bunch of amazing dumplings from House of Nanking and they were perfect. And by the way, then I talked Mandarin to the shop owner. Because one of the things I did was I taught when I was running Yex, I taught myself to speak Mandarin. And it's very funny because I'm like, well, should you? You know, I always tell them like, hey, like, you know, they I'll usually jump into a conversation when I hear the waiters talking, like, and I'll be like, you know, well, Howard Lerman, what a公司，呃，我的公司Yex有一个办公室在上海，which is like my last company had an office in Shanghai. And like, I'll jump into the conversation or like when I'm in an Uber and I'll hear people. speaking in Mandarin, I'll jump in, which is always kind of funny. Then they hear the white guy basically jump in. They don't expect it at all.

Definitely not.

And, and that, that was like a fun thing for me to do. I love learning languages. So I taught myself German, I taught myself Mandarin. Um, I want to teach myself Italian.

So— Maybe Farsi? Throw some Farsi in there.

Salam.

It's not very practical.

Well, you know, I do want to learn a language like where you have to read different letters.

Right.

So obviously Mandarin's like that, but Greek is kind of up there. Maybe advice is over the summer I'll travel, so I'll go take the family to Greece.

How long?

A couple weeks.

Do you work?

It won't be like the 996 routine because basically the time zones are different. The thing is, for me, again, working, it's not work. I know, I'm just asking, do you, as conventional wisdom goes, work?

Yes.

What I won't do is I won't go visit a Greek customer when I'm gone. When I'm in Athens with my family, or when I'm in Italy with my family, I'm not going to go. Believe it or not, we have customers in Italy, in Rome, Rome in Rome, or in Milan. I'm not going to swing by their office. Old Howard would have definitely done that. I would have like showed up and like, hey, ciao, let's go. You know, I'm in Milan. I don't do that. So I will, I will work. I'm on top of everything. I'll keep the design team going, keep the product team going, but I won't take a meeting in the city that I'm traveling with my family.

That makes sense.

Yeah.

I'm, I'm so eager to see how things play out. How's your attrition?

Employee attrition or customer attrition?

Employee. Like, uh, do people like working for you?

I don't know, you have to ask them.

I want to.

Well, the, the only evidence I might give you on this one is that my founding team at Roam, my CTO I went to middle school with, my, uh, COO I went to high school with. So I've been working with— and they were the executive team at Yext, so I've been with them for— my God, I'm dating myself— 31 years. Wendy, we talked about, I met when I was 19. How about this? Tom, I met when I was 13 over a Weird Al song, Frank's 2000-inch TV. Sean, I met when I was 14. They both went to Princeton. They're CTO, COO. Wendy, I met when I was 19. The rest, my brother is our head of room engineering, so I guess I met him when I was 2. The rest of the company are people who I basically, I would say the average tenure of having worked with is probably more than a decade.

All right. That's a fair answer. Your brother's there.

Yeah.

How's that? Is he like you?

No, he's way more reasonable and he is super patient. I'm totally not patient. He is incredibly patient. He is Brilliant. He is creative. He was a Broadway composer for a while, so he was an artist and a musician. And about 8 years ago, he decided— he actually— we tried to do the music thing together, the Dynascore app that failed, but he has reinvented himself in tech and he's awesome. I actually think that's a little bit of a hack for any founder. If you hire a musician, first off, they They've mastered a craft like a professional musician, and they're usually pretty technical and pretty creative.

Hmm.

And a lot of them, if you get them in— and they're patient too, because to play the guitar or piano with skill takes a lot of, you know, continuous focus and discipline. And so I, I like hiring people that have— we actually have like some pretty talented musicians at Rome. It's pretty cool.

Dude, thank you for doing this.

Thank you for having me.

Super interesting. Like, I was so looking forward to this. That's amazing. I appreciate it.

Well, I'm, uh, I'm really glad to have— any, anytime a podcast about grit reaches out, I'm gonna do it. And it can be— Angela Duckworth is a hero of mine. Yeah. And I, you know, she's— I've done dinners with her. And actually, I'll just leave you with this. Every employee of Roam, we send 2 books when they join. The first book is Ready Player One. The second book is Grit by Angela Duckworth.

Why do you send them?

We want them— I believe when people read the same thing, the human brain is a mirror.

But why those books?

Oh, those 2 specifically? Uh, Ready Player One is just an amazing story of a virtual world, which Roam is. And then grit is the defining characteristic of success, and it can be learned.

So why do you say that?

Well, I think I certainly have gotten better at it.

Why do you think it's the defining characteristic?

Well, the data, I guess, you know, it's funny, I went on a walk yesterday with Alok. I told you, my friend. And I was like, look, why do you think Yext was successful? What was it? And he was like, literally, we just never gave up. Literally, your determination. And he said you, but I think it was the team. We just, whenever there was a barrier, we just worked through it. We never ever gave up. And he's like, and from the day that I joined in 2007, he's like, you talked about the day we IPO. And we made it happen and we just made it happen through sheer preservation, not just running through walls. If there's a wall, we'll go around the wall. We just didn't give up. And I do believe that, and by the way, I agree with you on the partner, are 2 of the most—

Having a strong partner at home.

100%. For the journey are the key things in the hero's journey. And it's Joseph Campbell's monomyth, man. It's, you know, the entrepreneurial journey is, is rough and it's very easy to quit. And those that don't quit are those that tend to make it in the long run. It's not always up and to the right. You can have an up and to the right. You can make Google or Facebook, but most of the time it is basically those that duke it out and are good at suffering and pain tolerance. The Latin word for— right, this is what you guys talked about too— for passion comes from suffering. And if you, if you love suffering, then maybe you're gonna love making a company.

Are you hiring? Anything you're hiring for?

You know, I really could use a great podcaster interviewer guy, especially one that has an— if I had your voice, you have such, you have such a good voice.

Oh, thank you.

Like on the pod, like, because, you know, people are listening to it.

Yeah.

And I hate my voice. I hate how it sounds. I hate how I talk. And if I had your voice, I think my market caps would be like 2x.

You know, I never thought of myself as having any kind of voice. I thought I had a normal voice. And, and then you start, you know, it turns out you start doing podcasts, people—

You have an awesome—

Comment on the voice.

Yeah, you have a voice for What you do.

Appreciate it.

How did you start doing this?

Uh, how did I start doing this? I— when I joined Kleiner, I—

Do you do investments? I—

so this is— I'll tell you the story.

Yeah.

Basically, when I joined KP, I was very young to join a venture firm as, at the time, an operating partner. And, you know, I had like not that much experience for usually a role that's like the end of your career. Where you like, you know, talk about all the cool stuff that you did and you have all this history and network and all this stuff. Okay. And very quickly I realized that when I was talking to founders about the things that I thought that they should do on go-to-market distribution, for example, they'd be like brilliant technical founders. We would like go back and forth and then very quickly, like there was routes to go run. Right? And I'm like not full-time at the company. And I'm like, oh my God, like somebody needs to run these routes. And it's not me and it's not the founder. Like we need like a CRO, we need like a sales leader, like we need somebody to do this. And so I was like, okay, well, I know my old boss, you know, like I know a few sales leaders, not that many.

Right.

So I'm like, okay, I need an excuse to get to know these people.

Right.

So that's how the podcast started. Episodes 1 through 80, 75, were only CROs.

I saw you had Sam.

Blond.

I love Sam. I'm seeing him tonight.

You are?

Yeah.

He's doing his own company.

Yeah.

Sam's amazing. Sam was episode 4.

I— if I could hire Sam, he'd be my first choice.

Sam, Sam was episode 4.

He's the best. I love him.

Yeah, I gotta, I gotta reach out to him.

Um, are you guys investors in Brex or Ramp? Or either.

Brex. Brex. Brex. Um, Sam's a gem, and we're investors in— we're the Series A of Rippling, which he knows, uh, Parker, from the days. Um, anyway, so I just needed an excuse. And so, you know, it— like, I, I came up with this as a good excuse to get to know someone, like, on a personal level. And I talked about the things that, like, it was a cus— I'm a customer of one. I want to talk about what I want to learn about.

Right.

That's it.

Right.

And then after that, it just started taking a life of its own. So like my TAM was quite narrow and then over time it became CMOs and then COOs and then CEOs that were CROs. And then by like episode 90-something, it's like John Doerr and then it's like the AOL founder and then it's like the Intuit founder. And then from then on, it's basically all been CEOs and founders, right? It just took a life of its own. But right, that was the original intent. And by the way, still to this day, like, it's funny you say like the voice thing, like, I only do this to get to know guests. I just do this because I'm fascinated by people building companies.

Well, that's the Rick Rubin approach, right? I mean, the artists that make the work for themselves are the ones that succeed. Yeah, the audience is incremental. And then people make the mistake of trying to make it for the audience, what they think the audience wants. That's when they— that's when the art becomes not as good.

Well, actually, I think when people make what somebody else wants, they quit. And the reason for that is because they are not actually genuinely curious anymore. Yeah, they're just doing it for somebody else. And that's why most podcasts just don't make it past an X amount of episodes, because you start to get all of this feedback from the outside world.

Yeah.

Start to care about what they're saying about you.

Right.

And then you start to behave differently and then you, like, lose the original intent and pursuit of what you were doing. And so anyway, I always say the show is over when I am no longer curious about my guests or I get Elon. One of those two happens. One of those two happens and it's over.

So this was fun, man. I really enjoyed meeting you.

Thanks for doing this.

Yeah.

That's it for now. If you liked the episode, please leave us a review or go back into the archives where we've done more than 200 episodes with some fantastic folks. This podcast is a Kleiner Perkins production, and I'm Juvin. Thanks for listening.

Thanks for listening.