The Long Game: Squire to $750M | Dave Salvant, Songe LaRon

Brandon (00:24) Hey, another session that's gonna be really hot.

I'm excited because I've known these guys forever, right? And I've seen the complete cycle from them being you know hustlers, right? But really, you know, corporate hustlers, and then deciding to to start Squire, Squire Technologies. I remember when these guys were in the valley making the rounds, joining YC, which is by the way, very impressive at the time in and of itself. And then it went on to to grow.

Squire to a seven hundred and fifty million dollar valuation, which, as we all know, is very, very rare air to be venture backed in general, but to to operate at that level. I think more importantly though is the cultural impact that we see with Squire. Very rarely do you see people getting out there building something like this that's a clearly tech driven company, right? So the technology is strong, but also like the impact they're making, the way they represent themselves and the culture as as a

A CEO and president is something to aspire to. So with that, I'm just gonna say, Songe, Dave, appreciate you appreciate you all as always joining and sharing the insights and the wisdom for these young, hungry, maybe not so young in cases, but they're hungry, looking to to build wealth creation. You're here on a launch pathway. So you're gonna tell us about your story, Building Squire. So thank you guys for joining. Thank you for having me. appreciate you, Brandon. Yeah, excited to be here. Most definitely. So

I think what what always to me is really interesting about this story is how so many of us can identify with where you started and then the risk reward math that you were doing along the way, right? From the perspective of, okay, you know, at a certain point you all had to leave the job. You know, what did you need to see for that to be something that made sense for you? to a degree you all met, right, organically as friends and then kind of

went through this process together, right? And so I think this idea of finding a co-founder, why this co-founder is a question a lot of us ask. You know, and then lastly there's the element of how do you test these concepts out before you actually step out there? And you all had an interesting approach and how you did that. But let's kind of start with maybe just let's set the let's set the baseline of Songe. I'll start with you in terms of what was your kind of professional journey up to the point of Squire becoming a thing.

Yeah, when we started Squire, as you said, Dave and I were friends, I was actually a corporate lawyer. So I was working at a big firm in New York, called Skadden Arps and I was doing M&A. And I had been working at that firm for maybe about three years, two or three years, before we started Squire. And you know, like a lot of big firm associates, I was not really fulfilled by the work.

It was long hours and and and really intense, which which wasn't a problem, but it was more so I didn't I didn't feel like the the the work I was doing as a junior level corporate associate really, really mattered and like the bigger, you know, picture of of of life. It just seemed very monotonous. so after a a few years of it, I I realized like I'm not gonna be the person that's gonna be here ten years and my partner. So what else is out there? What are the other options? And you know, so Dave and I used to just kinda go back and forth about ideas and and that's what

No, that led to and actually starting Squire. Love it. So so Dave, you know, and and we knew each other socially as well. How did you actually meet Songe to begin with? And what was your your journey? Where were you in your in your career at that point before you all started really brewing on this idea? Yeah, thanks. Thanks, Brandon. so so Songe and I met informally, just hanging out in Harlem, in the kind of like two thousand ten ish.

two thousand nine area and and basically we used to there's a group of, you know, black young professionals, you know, that we used to just go out and hang out and and have a good time. We had common interests, you know, party on the weekends and and just, you know, I think it was a it was a great time to to meet valuable connec connections and like minded people. So that's kind of, you know, how we met socially and, you know

going out and having fun on the weekends and really just, you know, enjoying, you know, Harlem in the you know, early two thousand tens. And what were you doing career wise at that at that point? So so so I was in finance, working at, you know, JP Morgan Chase. and then actually, you know, we started I started we started Squire, you know, during my first year of business school and yeah, that's kind of, you know, what I what I was doing.

So Songe, go ahead. And you know, I wanted to hear why why was Dave the one that you really locked in with when it came down to let's do something, right? Because and and you know, look, you had you came from this hot pedigree background. I want you to share about, you know, a little bit about that as well. But you had this ability to see like past with a lot of high, you know, kind of achievement folks, these kind of blinders. I need to do this, I need to present myself in this way to be successful, right? It's almost kinda in some ways like it feels like a prison.

You were able to kind of break through that. And I feel like Dave always represented, at least to me, someone who was always ex exploring different different ideas and people and relationships. What was it that drew you to to Dave and you know, it really locking in with him in this in this idea of kind of exploring entrepreneurship?

Yeah, as as they mentioned it it grew out of just a j genuine friendship where it started off socially. We were had a pretty tight knit group of friends, all lived in Harlem, all were making money for the first time in our lives in our, you know, early to mid twenties. So it was just a really, really fun and exciting exciting time. and after a f a few a few years though of just you know a a lot of hanging out, getting to know each other, we built some really great relationships, but also we were

started to get to a point where we were asking ourselves like what more is there to this? Like it just seemed like kinda like this hamster wheel. Working during the week, you know, partying on the weekends, you know, getting tables and, you know, all all that bottles and stuff. And then, you know, next year back Monday, same place again. And it was just like this can't this can't be it. So I think we're kinda connected on that point where we both were were wanted more. Want one was wondering what what more was there to life? and

And I think that we both have a very entrepreneurial spirit. I I I went to law school as you as I mentioned, I went to Yale for law school and and came out and and went directly to the firm. But prior to starting life law school, I actually had a company out of college. So I took a year off between undergrad and law school. And I started a tutoring company back then. So and ran that for a year. so even back then, like there was this entrepreneur entrepreneurial kind of spark.

And I think Dave, you know, I connected with Dave on that front 'cause he's very entrepreneurial. you may remember the tik the the infamous tequila room at Harlem. In Harlem, which was one of Dave's first ventures, which I remember, you know, distinctly and and we were all so excited about it. And, know, you could just see that he had had it in him to to just be somebody who creates things and is able to influence people and just kinda you know, really push things forward.

so I think that that's the kind of energy you need to be successful as a founder. You need to be able to just make something out of nothing and just have a sheer will to to manifest, you know, things and realities from your mind. and so I think we both kind of shared that. And and and then there was a genuine connection. I the the the best founder relationships, in my opinion, often have a foundation of of of a real friendship. It's not just pure business.

Well it's pure business when it go when the times get hard and there's conflict. oftentimes, you know, yeah, those those relationships deteriorate. But if there's like a common friendship and respect there, then you you can you can survive those hard moments. So yeah, that was that was that was it. And we we started just thinking about ideas and brainstorming and eventually both committed to let's let's try to be great instead of just working at these companies.

Yeah, th there's you know, out of a friend group there like nine, ten guys, you know, all about the same age. And, you know, I think I think, you know, Songe went around to to a bunch of them and and a lot of them, you know, like started something and they didn't they didn't they didn't want to participate, you know, like they didn't want to, you know. And and then, you know, I guess when, you know, we we spoke about it, it was like, Yeah, why why why not?

You know, it was one of those things where like, hey, if you don't take the risk now, when are you gonna take the risk? You know, like, you know, everybody can't be like you, Red and and and wait wait ten years or fifteen years and and get this nest egg built up. But but I think I said like the biggest risk is not taking the risks and you know, I didn't wanna get golden handcuffs later on where you're making so much money, it's just like

You're you're in this spiral where, you know, it costs too much to leave and you have this these these, you know, responsibilities like, you know, mortgages and and stuff like that where you just can't take take the risk, because it's just too costly. you know, and I really believe, you know, that you know, you have to you can't be halfway in it. You have to be all the way in it in order to like really, you know, back against the wall, this is gonna work, plan A type thing.

Because that just, you know, makes you focus on on a on another level where it's like, hey, this is how I have to eat and, you know, this has to work. I think there's a different mentality, you know, that has a sense of urgency. That, you know, if you're doing something not part time, but like, yeah, it could work, it could work, it couldn't work, I'll I'll still be okay. I think that drives a different level of urgency in you to kind of like

Get get it done and just make action happen. Let's get into that into that entrepreneurial mindset because you know, Dave, when I think about you, man, I I see, you know, take this for take this comparison for what it, you know, for for what it's worth. Like a Tupac, right? Tupac had he had this urgency, right, to move and and do things. I remember when I met you, you had a social concept going on. You were early in on the Airbnb thing before it became a thing.

You had your hand in so many different pots. And the other thing was, like, Tupac was very prolific, right? In a short amount of time, he had like an incredible body of work, right? And so to me, that hustler spirit, you combine that with like this ability to really see out and not really feel like there was nothing that you couldn't do if you weren't riding towards it. So I would argue back then, I want to hear how long ago you all actually started Squire. Tech was still kind of like,

earlier stages. I remember I was at Google at this time. We had moved to the Bay before you all did. but it was early, right? It it wasn't many people saying, let me get into the game and start a tech company, especially if I didn't have an engineering background. This was something that you locked into and said, we're going all the way, right? And then you got validation, which was you got into YC, et cetera. But it all kind of came back to me around really getting busy, having urgency.

seeing something that was out there and saying I could actually do this. what's your reflections on like how tech in a tech concept specifically became what you thought was the quote unquote hustle, you know, that that was gonna, you know, give you that that best shot? yeah, that's a great question. So so those little hustles, the Airbnb the the tequila lounge, all that, that didn't have a exponential return ability. You know, and and when you when you're like

thinking about like how can I have, you know, generational wealth and outcomes, I think it's focused it's important to focus on things that if this wins, it's gonna have a enormous return. and and that's kind of was the the litmus test is like, hey look, you know, you could do these little hustle things or you can lock in on something big and and and lock in for a couple of years and and this can have life changing effects. So that's what was really, you know, the the question to me is like

Hey, this has a potential, this, you know, gets big enough, will it change the legacy of of my family? And and and that's kind of where you where where you want to put your efforts in. It's kind of like with V V C models, like bet on something, commit to it, and you know, if you if you win, you win. If you lose, you can always go back to, you know, starting something else or or pivoting. But, you know, the worst case scenario is you'll learn something that's invaluable about yourself.

And you'll learn something about, you know, what what you what you' what you're made of. So Songe, you you, you know, again, we're gonna do the risk calculus right now, right? Dave had a bunch of head irons in the in the in the fire. You're working M&A at Skadden putting in some serious hours, right? For you, you had to do some some different math in terms of what you were walking away from, in terms of the perception risk. You know, Dave said locking into something big that he felt, you know, was was worth the the juice was worth the squeeze.

But you gotta really believe that, right? To step out there. You really gotta believe that you can create a a tech company that can achieve a seven hundred fifty million dollar valuation. How are you thinking about this opportunity, you know, at the time where it was this this trade off of, yes, I am young, but at the same time, like, you know, this I have to really believe in the potential of this thing.

look at it, I looked at at the time like like an asymmetry of o of risk reward. so meaning that you could pretty much define and and and cap like what the potential risk would be. Like we try this, we leave the job, you know, it goes to zero. It's a complete failure. What is what is the actual tangible impacts of of life? And and the way I looked at it is like, yes, that would be a setback, but it wouldn't be any it wouldn't be existential. It wouldn't be something that I couldn't recover from.

I could worst case, I could always get another law firm job or you know, find something else in the corporate world. Conversely, the upside was was is essentially limitless. Like there's this the as as entrepreneurships to start at a company and owning capital, there's no there's no limit to how much wealth and how much impact you could have. So from that perspective, it was it was a really actually an easy call, coupled with the fact that

I really did not enjoy and wasn't happy at the firm. So that made it even easier. So people always ask like how did you make the leap? And it w it wasn't at it, it was the easiest leap I ever made in my life at the time 'cause I was just so ready to to move on to something else. and fort fortunately i i it it worked out, but I I didn't know that the time was certainty. but I always b I believed that the potential was great and that we would eventually b be successful. So I never really looked back, never questioned it.

was an i it was an easy decision. Yeah, and and there's a there's I forget who who said there's a podcast or or something I was just the other day and that describes this situation pretty pretty spot on. but it's with capital when you invest. The worst thing you can do is lose one X. You know, one X your money. But if you hit and you go it's the the amount of of multiples you can make are are are amazing or are just

almost infinite if you hit the right thing. But you can only lose one X of what you put in. So i if you take that philosophy, you know, l and and you're confident in yourself, you can only lose like your time, yeah, yeah year, how much is that worth, you know, a couple. But but if you if if this goes big, you know, it could really be life changing. Okay. So let's let's go from, you know, we're talking about the ingredients of becoming a great entrepreneur and and obviously you all have earned

those stripes, you know, you will go down regardless of whatever happened from this point on as a great entrepreneur, simply based on what you already accomplished. We know assessing risk, right, getting into the game is a blocker for a lot of people. You already, you know, you kind of broke down how you got past that that stage. But Songe, at the end of the day, you have to find the concept, right, that you're gonna hang your hat on. And that process is not pretty. Can you give us a little bit of insight into where you started?

You know, you and Dave kicking around concepts to honing in on Squire, you know, maybe good let's call it V one Squire and and maybe how that has morphed into the platform today. Give us a little bit around, you know, what Squire does and and the needs you were looking to to serve.

The process was that we started on the weekends instead of going out during the day at least, instead of going to the brunch party, we would we would sneak into Columbia campus uptown and we would go into to the classrooms and just start whiteboarding ideas. And we did this over several weeks. and we were just trying to think of whatever like what are the problems we could solve, what are things that we understand that should exist and we were we were very focused on on tech.

and w and it being a tech company. And, you know, today's earlier point, we wanted something that had potential exponential scale and and impact. so that that much renewed. But other than that, we didn't really have any priors. It was just trying to start from first principles, blank canvas, what are the things we could do? Throughout through that process, we eventually came to this concept of of the barbershop and and it w it was rooted in our own experience, which I think are the best companies

in our own problems of every week we're getting a haircut, going to, you know, different shops, either in midtown near our office or, you know, in Harlem. And the process was just so inefficient of texting the barber back and forth, having to have cash, you know, get in there and you might wait ten minutes or you might wait two hours, which is, you know, okay when you're like a kid growing up, but when you're, you know, a busy professional, that's just unacceptable. And it it didn't make sense that this is like the last area of life at the time there was

pretty untouched by technology, and so inefficient. Yet at the same time it was such an important ritual, in in pretty much almost all men's lives of you go in and you you come out feeling like your best self, feeling like confident, in a way that you didn't when you when you first walked in. So it was a pretty magical experience and at the same time really antiquated a and quite frustrating. So that that was when we stumbled on that idea, we were like, Okay, we think we have something here and and we started getting excited and started doing

more research, talking to barbers, just walking in the shops, talking to people waiting and trying to get as much data and understanding from the customer of like, is this real? You know, can we validate this? And and we thought it might have been a b a a black barber issue at first only. but then the more we talk to people, different communities, different cultures, we started realizing, wow, this this is like a universal experience. This is something that's shared across you know, d d different groups, so we could really build something big.

let's talk about Dave the grind, right? You know, nowadays people wanna they see you and they're like, I don't wanna say you made it look easy, but in many people's minds you all have built the dream, right? Is your co founder, right? You know, the the the name Squire is a dope name. You're in barbershops is cool, but it's a tech company, you have this in this valuation. I could do that, right? It's is is easy. They did it. But, you know, we know deep down it's a

a lot, right? It took a lot to get to that point. Can you maybe Dave share like give us an appreciation for the grind, you know, the tough times earlier on. Even even now, like help us understand how hard this journey really is. I mean, if it was easy, everybody would do it, right? That's the that's the adult saying. But the thing is like the earliest with grind, you know, a lot of no's a lot of nos, a lot of people not believing.

A lot of a lot of you know pigeon boxing, you know, like pigeonholing, you know, us, you know, saying that this is just for black barbers, a lot of difficulty raising cash at first, you know, during our C Series A. You know, we didn't also like even though we went through Y Combinator, we didn't get that inflection of cash. It was just like build lay down the tracks, you know, get some traction, go back with your hand out, try to get some more money.

you know, a lot of times we get we we we almost ran out of money. We almost ran out of money during our series A series A fundraise. You know, only getting one term sheet after sixty meetings, you know, so it was it was it was not something that was easy. But I think, you know, not one point did we question giving up, you know, because we knew that we were building something, we knew that we had product market fit and customers

we're using our product and when customers are using your product telling you that they appreciate what you've done, you you've streamlined my operation, you know you have something, it sometimes it takes, you know, other people to realize, you know, what you're doing. And at the end of the day, you only need one yes no matter what how many no's you get. And I think that is the, you know, defining factor I would say is grit and determination. And you hear that a lot, but it's it's actually true. I mean

You know, people give up right when they're on the precipice, you know, right when they're on the cusp, people often give up and the ones that, you know, just keep going and fighting through the strife is the ones that actually make it. and and luckily, you know, we we we persevered. but I think if you if you work hard and you keep on going, you keep focused and you don't get discouraged, and it's easy to get discouraged, you know, when things aren't going right. But, you know, if you if you have, you know

product market fit customers, I think that's a that's a telltale of of of of you have something there. So Songe, you know, we d Dave is basically talking about, you know, the perseverance piece, right? And I think, you know, when I think about Squire, maybe there were some pivots in there, but if anything, I think you are just broaden a portfolio. But the core thesis kind of remained true. So I don't know if the the pivots we've seen from, you know, Instagram was this before it became that, Twitter was this before it became

That didn't really happen in in your situation. And so my question for you is, is it really the perseverance piece? Or are there times where people should kind of see the writing on the walls, you know, hear the feedback and say, you know what, maybe this isn't the right concept. Like how how should people think about keep going, keep going, keep going as a philosophy versus like trying to really understand and and you know, pivot or or even stop? Is that, you know, help us understand how to think about that?

Yeah, there's there's an element of perseverance and grit that is a necessity because even if you have the best idea, the best product, team, everything in your favor, like you're gonna get kicking the teeth at some point. You're gonna you're gonna like it's inevitable. Even the the most successful entrepreneurs will tell you that. so you gotta be able to take a punch and get back up and just kinda, you know, be determined to to keep pressing forward. but I think that

You need to be flexible and and and open to pivoting 'cause you know there's some people that say locked in on an idea and and it's it's clearly not working and and they just, you know, are are keep keep pressing forward. But I think the the what that that needs to be based on is is ultimately the customers. a lot of times entrepreneurs and and we've you know, I've made this state, you know, at at happen in the past. You you be you become really like fixated on an idea, but that that idea or that

product or feature, whatever you're working on, is really in furtherance of like your own interest and you're not putting your customer first. And a lot a lot of the biggest mistakes we've made, that's been the case, we we we've never made a mistake by putting a customer first. So if if the if the data that if if you keep trying you keep trying for something in the market and the customers are rejecting it or not paying for it or they're churning, then that means you need to p you need to change because the the market and the customer is telling you that what you're producing it ain't working.

But if you if you are getting that signal from the customers that they actually love this product, they'll pay for it, then you just keep going no matter what, because because you're you're getting that positive feedback from what ultimately matters. And I think you'll never go wrong by caring too much about by your customers and providing too much of a great experience. So it's kinda you you have to have a balance of that sheer just determination and also flexibility and ability to to change through the lens of

What are you hearing from your customers? Got it. That that makes a lot of sense. Dave, let's talk about milestones, right? And you know, obviously hindsight is 2020, but you know, someone just brought this idea of customers, right? And and and you know when you're going in the right direction when, you know, a customer has really leaned in. So let's talk about we reflect back these milestones that you knew like we're really on to something, right? And so maybe it's a customer that you went over, maybe it's getting into YC.

Maybe it's some other milestone, but when you kind of reflect back on like some of the the key moments that you knew you all were on to something, what what were some of those moments that come to mind for you? I mean, I think YC was one of the an inflection point where we got into my YC. But before that, it's like when people were giving you the opportunity to run their whole business operations on a platform that was improved.

And you you've seen it work. You see people booking. You see people coming in and and using your system and also being appreciative of of what you've built. Even though it was janky, even though like some of the V ones of our product was so, so bad, I don't know how these organizations trust us with with with their business. But they did. And and and and that told me and told Songe that, you know, we're working on something special. If an organization

And and and critically, like a critical component of their o organization of small businesses the money and and then money movement. And if they trust trusting you with their livelihood, that means with a with a product that was not good not good to say the least, then you're you're working on something and you just have to iter iterate to make it make it make it better. So I think that was the first

kind of like sign of of something like product market fit is cause people would go through the pain of using a product and still use it and we see w we saw the the transactions going up every month. We saw the the the the people willing to take chances. I don't know why they were willing to take chances but but ultimately they they did and and I think that was the first indicator that we were working on something that had had some likes. Got it. I think it's 'cause if if you're solving

a problem that's a real problem for a customer and it's something it's a pain that they're feeling viscerally and you're attempting to solve it, they will be very forgiving if it doesn't work 100% because they can see what you're trying to do. Versus if you're solving something they don't care about or that is like a vitamin, not a painkiller to them, then they're gonna be much less forgiving because if it works, it's not even gonna be that impactful anyway. And even though our product wasn't that great rel you know, especially relative to DAO

They could see that what we were building was we were the only ones doing it. And and we were we were really trying to do something that would add a lot of value to them. So I th I think that's why they were willing to work with us. I remember back in the day when you all were NYC and, you know, I think we we gotta talk about this part. You both are, you know, accomplished professionals, you know, both on the court, off the court, but you you were not engineers, right? And you're building a tech product. So in a lot of ways you were dependent on somebody else.

to come in and and be the be the the the technical builder for you. We could go a lot of ways with this conversation. You know, it could be how do you recruit people, right? It could be how do you identify the right talent. but I think at the end of the day, when you take, you know, when you're in these situations, really it's your your ability to sell, right? Sell a vision and sales really got the core. So Dave, help us understand how how a non-technical person can successfully build

First of getting a Y Combinator, which is known for you need to have an engineer, right? You have two co-founders who are not engineered. What was the story there? How did you think about this evolution on the technical side to to find somebody to build what you were looking for? and ultimately, you know, I think sales is a big part of it, but how are you able to continue to recruit people and and stick stick around long enough to even iterate through that process of finding the right, you know, builder for you for you all? Yeah, I think I think we were lucky and fortunate to find, you know, a technical

person after, you know, it's a it's another story on top of that. But we were lucky to find a technical person who actually became the CTO and we were able to convince this person to build this V one of the application that was just good enough to get into YC. we needed, you know, 'cause Michael Seibel back there was like technical, technical, technical, technical. We applied to Y Combinator three times.

On the third time we we we got in to the to the fellowship program and then we actually was ab were able to get into the the YC core program. So we we applied a bunch of times, but the first time we didn't have a technical co founder, second time, you know, that person just started and third time we had s somewhat of a a product that was that was built. So, you know, we got lucky we were able to, you know, convince this person to join the team as CTO.

And that was enough to get to get over get us over the hump. To your to your point about selling, at at that time, the this is before, you know, AI, obviously what we have now, but at that time, if you were not building product or an engineer, you are selling. There's no and there's only two things that a startup needs. It's the building of product, selling and getting customers. So if you're not tech if you weren't technical, you needed to be able to sell. And the first person you had to sell

Well the technical co-founder. Like there's just no no really no way around it. the only solo founders at the time really were technical. So like if it could be one person that could build and if it but it couldn't build the other way around. Like there's really no way to build a tech company. You could outsource it, but that almost never works. It's just you spend up spending a lot of money and getting, you know, poor product in return. Now, no, fortunately, this is a super exciting time to be a builder.

because these AI tools are just incredibly powerful and and and in in my opinion, the line between technical and non technical is is is is gonna be very blurred. And and in other words, not being technical is no longer an excuse. like go figure it out. Like you should be able to figure it out and and and co you know, vibe code your way to a functional prototype and or an MVP.

I think. I think anyone should be able to do that at this point, given the tools. and I know because I use them. Or, you know, like you have to be in it. so I think that's really, really exciting and and dope time for founders. But back then, you know, 10 years ago, there was no, no, no way around it. we had to get a CTO. This is actually a good segue into, you know, this conversation around raising venture capital, right? in many cases, it's hard to do.

In general, right? So even if you wanted to do it, it's it's definitely not promised that you're gonna be able to, you know, become a venture-backed company. But you all went through this process, right? Which is something else you can speak to with insight. Let us know what type of person or company or concept is best aligned with the VC model and what are the, you know, the pros and cons on both sides, right? And maybe, you know, you mentioned this Songe a little bit. How has this

How has your thinking evolved now with the power of AI tools to build these MVPs, et cetera? So you were a little bit of a different era, but some things are gonna hold true regardless, right? And then some things might have changed. what's your perspective on that? And I sorry, I'll come to you first and then we'll go to Dave. Yeah, I think the venture model hasn't hasn't really changed that. I mean changed, but not not fundamentally. whereas that they are looking for home runs.

So they're, you they'll place a hundred bets and and they only expect, you know, one one or handful to to really pay off and return return the fund. So as a founder, you have to understand that and ask yourself, like, is this a company that I'm building that could reach that level of scale to give the kind of returns that would be exciting to venture investors? you know, at at the time the goalposts have been moved a little bit, but you know, at the time it's safe to say like if if you have a pathway telling a story of like how this could be

a hundred million dollar, you know, revenue business, like that's usually pretty exciting. because that means that this is probably a a billion plus, you know, valuation you know, opportunity. and the earlier the investors get in, you know, the the the the the less big the company has to be for them to get a good return, meaning that if they if they invest super early like pre-seed angel, you know, and you you build a hundred million or two hundred million dollar company, like that could still be a very good return for them.

but if you're raising series A, Series B and later, then you the the goalpost moves and you gotta tell an even bigger story. And that is something that early on we struggled with, because we would constantly get pushback about our addressable market, how big is it? And th there's not a lot of reliable data that exists. So these investors would go Google how many barbers in the US and and because it's not a lot of good data

There'd be ridiculous you know, sites. It would say like there's six thousand barbershops in the US. And then they would come back to us and say, Well, there's only six thousand barbershops. How big could this be? And I'm like, dude, there's six thousand barbershops in Queens. Like, like there's no way that's the whole US number. So we had to get good at getting ahead of of their you guys hearing feedback or is that just me? No, you're good. okay. I had some feedback. Yeah, I'm hearing like just started.

I I hear you fine, but take that echo cancellation on on the side, but keep going. All right, all right. so where where was I? I was talking about the V Yeah, yeah, yeah. So we're so so yeah, so we we would like just you know, there's six thousand barbershops in Queens, so obviously that's not accurate. So we had to get better at responding, predicting what their pushbacks are gonna be and then having a story for it. and over time

We learn more about the business, about the industry, about our own kind of, you know, revenue model. And we started being able to paint the story of like, okay, this is how many shops there actually is. Here's a bottom up TAM analysis, here's a here's a top down, and here's how much revenue we make per barbershop, and here's how it grows over time. So then you can put all the pieces in place to tell a story that's believable about okay, I can see how that could scale to these numbers. But in the early days, you don't you don't know that. Like you're really just

putting your finger in the wind. And that's okay. Particularly in the valley. The the the ethos and the culture of the valley is dream big, go big, you know, talk about how you're gonna get to, you know, a hundred million, two hundred million, build a build a ten billion dollar company. You have to have that kind of vision, even if it feels uncomfortable. And that's something we had to learn. And I think a lot of times, you know, people from, you know, our communities, black black communities, like we we want to be very when we start companies, like very practical. We wanna like tell a number that we

are very confident and in this reasonable that we can that we can and that is a bit limiting when it comes to VC you know, batched companies and like just, you know, winning in tech in Silicon Valley. Like don't limit yourself. Think what's the biggest possible version of this and like, is it even possible within the laws of physics could this happen? Yes, okay. Like go for it then. Like like that's how you have to think. And you may not hit it, but if you you're gonna get a lot further than you would have. so that's one thing, you know.

that that we've learned. Dave, same question framed differently, which is Dave, the hustle king is starting right now. How would you approach the game? I mean, yeah, that's a great question. so I just want to say something, you know, the Songe brought up, you know, about the market size and how lazy VCs are sometimes. They're gonna have conf confirmation bias any which way, you know, and when you when you approaching them, you know, you can tell

You should be able to pick up whether they like the idea or they don't like the idea because what what often happens is when they like the data they're gonna look for data points that support it. And when they don't like the data the the idea they're gonna look for I c points that don't support it. And y we should pick up really easy, like it just didn't make any sense. they just did a Google search. You're being lazy, you know, like that's not you're not that's no you're not having any mental exercise because you i there's no way six thousand barbershops can support

you know, three hundred three three hundred million people. So so like that that stuff happened a lot early on. But but to your question, if I was, you know, starting a company right now, you know, I I would I would do things that are you know, I would try to focus on things that are central that to to life and health and and and stuff but stuff like that. I feel like with with AI a lot of things can be done really quickly. You can iterate really fast and you can get

your product in the hands of customers really quickly. And once you do that, you can validate ideas and you can see if there's product market fit or there's interests. I think, you know, I I like small businesses. I think they're the the the backbone in American economy. and, you know, they are very easy to approach and and talk to and you know the the barriers to entry

to to to have a conversation aren't that hard. When you when you go, you know, maybe upstream to, you know, more enterprises, that's a little more difficult. Those are they're entrenched and in in in their, you know, processes. So, you know, I think and and and and oftentimes, you know, people from, you know, our backgrounds who don't have the technical expertise, you know, it doesn't make sense to build the enterprise level

enterprise product tool if you don't have if you're not from that industry and you don't have the relationships because the barrier to entry and getting in there is gonna be difficult and getting those to advocate those those furly those early evangelists is is a is a challenge. So I I would think about businesses that are close that you have some sort of expertise or unfair advantage in and think about like and see those inefficiencies and kind of build something to to to that to that notion.

Songe, scaling, right? You know, so how how long has Squire been around now, total years? 11. First of all, congratulations, audience. Get give the virtual round of applause. because again, you know, people talk about survivorship bias, but you know, you all made it 11 years. That's that is not a small thing by any means. But during those 11 years, you went into

Okay, you know, now we are growing our team. Now we're dealing with competition, right? That's a thing. You know, we hit the pandemic. You know, we're we're now dividing our roles differently. We're bringing in, you know, we're hiring and maybe making some mistakes. so you know, tell us a little bit around that journey of scaling because it's like a Zuckerberg situation. Like, yeah, it started off Har Harvard only. Somehow along the way, he's been able to move and shake and Bob and we

to to run a completely different company, right? And so you have to grow along the way. You know, what have you learned in in scaling Squire that we can we can, you know, kinda to pick up some wisdom from?

Yeah, you're you're you're absolutely right that when you start a company from inception, from idea, literally an idea, all the way going through, you know, the journey of of the company maturing and then, you know, scaling and getting to kind of where we are now. so much changes. So much changes about the company itself, you know, the number of customers you you're interacting with, the product, the employees that you need to bring on at any given time. And

A lot of people who are part of the company in the early days, eventually the company will kind of outgrow them. Like, and that's okay. That's a natural part part of the part of the process. and then you have to find new people who are, you know, have what it takes to get the company to the next level. and as founders, if you want to kind of be in it throughout that entire journey and still adding value and and you know, making the company successful.

then I think you have to have you have to be a learning machine. Like you you have to, yeah, gr growing and and and learning is is kind of like your core job. because every six months or so, the the ground shifts beneath you and and the skills that are required changes. And the way you talk about the company changes and the narrative changes and the way you communicate in some ways has to change. and there's no way to do that successfully you know, based on what I've learned thus far without being very, very

adaptable and evolving with the company as it grows. and just to give some more concrete examples, like when you first start, you know, first year or two, you're trying to find product market fit, a company should not have a lot of bureaucracy and process at that time. that's why it's a mistake to hire big, big company people for early stage companies because they don't know how to move and navigate in an early stage environment. you you need to be able to just, you know,

throw things at the wall, see what sticks. Everybody's doing everything. You're focusing on customers. You're selling. You're doing customer support. Like is you have to be able to be a generalist, a super generalist. and and and then, you know, as the company starts growing, and then eventually it would it'll you'll hit a point where that stops working. And now you actually need process. And now you need to bring in people who have done it before, who have built teams. and the only way to be able to do both is you you have to be adaptable because a lot of most people are either

Early stage people, mid stage people, growth stage, public IPO type companies, type they work in companies like that. Very few people can navigate in in in all the above. and I think that's what, you know, you mentioned like Zuck and like a lot of these guys, like that's what the great founders are able to do. they're founder led companies and they've been able to grow with the companies all through the journey and are still operating at a really high level excelling. so that's what, you know, that's what I aspire aspire to do. I think we've been doing a good job.

you know, so far to getting where we are, still so much room to grow and so much learning to do. but it never Never stops. Never stops. Dave, same question, right? We hear we hear like, you know, nine out of ten, you know, startups are gonna fail, right? You all are in year eleven. Again, you know, applied take you know, tipping the hat to that. You know, what are the lessons you learn from scaling? And and another way to put it would be, what would you, you know, from your lessons learned, advise other folks

So that they're not in that nine out of ten, you know, that that aren't gonna make it. What I would advise other people is like, you know, as Songe said, be adaptable. you know, as time as time goes on, like you you learn a lot. You learn a lot about yourself, you learn a lot about the organization, you learn a lot about the people, you learn a lot what what you're good at and what you're what you're not good at. And I think a lot of folks

try to be good at everything, but you know, you're not gonna be the best finance person. You're not gonna be the best marketing. And when to bring those people in is critical. And also, you know, delegating responsibility and and giving people autonomy, I think is also a good a good a skill to to create, especially later on. early on, you know, I I think, you know, in order to succeed

you have to be, you know, willing to do anything and everything, when you're early. You know, you have to be willing to if somebody you have to be willing to go into a barber store and run the front desk. You just have to be it you just have to do it. You know, and I think having a philosophy of nothing is beneath you the meaning meaning like if if shit comes I'm sorry.

If if if i i if stuff hits the fan, you know, you will be willing to, you know, do whatever it takes to to get this get this done. You know, I think you know CO NVIDIA always says this, you know, as part of his thing. He said, Hey, I waited tables. You know, I I did this. So I know where my low point is, I know what I'm willing to do to in order to succeed. And I think that's has to be the philosophy that you'll do anything in order for this to achieve.

success even if it's going to going to you know doing the bare minimum what needs to get done. But that's not what you ultimately are responsible for and ultimately but it's the mindset. It's the mindset of like, hey, I'm willing to do this if necessary. You know, and then also that that ethos radiates throughout the organization. You know, if if if if you can say like listen

I'm willing to to the customer success person, you know, I'm willing to do your job if I need to and I I have to, I think changes the culture of the organization. And I think, you know, yeah, that's not scalable, but it's it's it's actually the mindset and what what kind of like transcends companies. So basically is is the inner battle becoming the bet the best version of yourself and then that sets the culture from the top.

To create it, you create an organization that will ultimately see, you know, see your example, live by your example. And so if you're not doing it, you're not setting up a culture for success. That's a lot of wisdom. Songe, let's let's switch gears a little bit, man. You all now, you know, you hear 750 million. That means you, in a lot of ways, unlocked a new level of, let's call it, security for your family and future generations. Talk to us about.

How that changed your outlook, right? People are looking at, you know, a lot of the reasons that people want to do it, whether it's the right reason or wrong reason is they want that, they want that, that, that opportunity to create a new, you know, circumstance for their for their future generations. When you got to whatever moment that was where you're like, I mean, you know, I've I've I've hit that milestone, right? One of the many milestones, but a major one. How did that change how you thought? What were you exposed to now that you can maybe share with other people around the challenges, the

the opportunities that you see now that you're kinda at a different level of the game.

Yeah, I think that it's a reflection of yes, we all wanna get paid, you know, everybody wants to, you know, be wealthy a hundred percent. From a founder perspective, like creating a company, it's it's reflection like the value you create for customer. If you create enough value for customers, get investors brought in on that, then you you you in turn can like the wealth that you're gonna

Acid ass get is is is just a small percentage of the hopefully the value that you're creating, you know, for your customers and for the world, for all the shareholders. so but yeah, we were fortunate and and when I look back on it now, it was actually in a relatively short period of time, even though it didn't feel like it in the moment. But some we've we've been running the company for so long now that when I look back, so we started twenty fifteen, launched twenty sixteen. By twenty nineteen,

We we had raised a s raised a series B end of end of twenty nineteen and took our first secondary. So really you're t you're you're talking about three and a half years and in that sec secondary is when when you raise money and then you s I know you know, but just for the audience, then you you you s you sell some of your shares as part of that transaction, and you actually catch some liquidity. so within three and a half years we were liquid millionaires, which is kinda wild.

and that just shows the potential of being an entrepreneur and taking a better on yourself. Because to have to be a million liquid, like I know I know people who worked at law firms and may partner and still want liquid a million dollars because their expenses are so high. so that was pretty incredible and that fundamentally changed I I'll speak to my life. growing you know, never growing up with wealth. you know, being being, you know, the the wealthiest person in my family just from

having worked at a law firm, not from actually ha, you know, had having substantial wealth until that point. and and then it definitely changes you in in in a lot of ways. And in some ways I think it makes it can make you a better founder because it's it's that's not enough money for you to just be like go retire on. But it's it's it's enough to give you the confidence and the st the stability to to to dream even going bigger.

because now you've got a taste of it, your family's comfortable, you're not stressed about finances, paying bills, mortgages, et cetera, and you can be really locked in on growing the company and also makes you go bigger because if selling a company for a smaller amount, once you're already, you know, a millionaire liquid, selling a company for let's just say, you know, two hundred million and and and making another ten, twenty million, like that actually is not that meaningful to you. Now you're like, All right, I'll put in the time to go even bigger.

Like now, but like we we're folks like this is gonna be a billion dollar exit come hella high water because like otherwise my life's not gonna change that much, right? So that's another you know kind of positive of it. But I I really always recommend founders, if you're fortunate enough to get to the opportunity to take secondary in your journey, hundred percent take it, 'cause you don't know what the future holds. We we took that secondary in night two thousand December nineteen. We didn't know what was round the corner.

And it it allowed us to go into that that period, you know, of COVID, much more stable, much more stability, much less stressed than we would have been had we not, you know, taken it. So yeah, that's my two cents on that. That's that's that's big. And it shows you never know it's around the corner to your point. That security is super important. Dave, it's like the ring, Lord of Rings. That that liquidity, you can you can either lock in and get more focused or you can get really distracted.

What what was your experience kinda achieving that? Liquidity wasn't that much. so it doesn't it doesn't really, you know, move near for me. I think focus on, you know, getting this, you know, to multi billion dollar exit, that's when that's when the real magic happens. You know, and I think

I respectfully push back a little bit. A million dollars a lot of money for us at the time, bro. It wasn't that much. You see how rich this guy is now? You know, look, get out of my pockets, basically. I can't No, but I think I think I think focusing on the focus on the the like North Star of like, hey, like what provides like generational generational wealth. And that's just not

you know, and that's us to get to, you know, exit. And that's kind of what what we're focused on, you know, like how do we build enough value, you know, where, you know, this company, you know, is you know, two hundred million revenue or whatever the case may be, where we can, you know, have a meaningful, you know, exit and make all our stakeholders and our employees employees, you know, really, really wealthy. And and that's kind of, you know, where we at because

Not everybody's the founder. Not everybody's gonna start a company, but you know, if you join the early stage company, you know, and take the risks, you should participate in in in the financial outcome of when, you know, it gets to you know sale or something like that. There's plenty of people who made a lot of money by joining these companies early and and getting equity in the in the company. And that's a p another pathway to to wealth where you don't have to take on the necessary risks, but you still get upside on on the back end. So

You know, I think that's the goal is to, you know, get to, you know, a transaction. you know, whether that's public, whether that's, you know, selling, you know, who knows what the future holds. But that's that's the goal, is to, you know, have have some type of exit to kind of complete complete the story. Right. To g make the cipher complete. Now, I'm gonna one last question for both of you guys, 'cause I know you gotta get back to running this business. Dave, there's multiple types of currency, right? There's the currency we just talked about, but then there's

relationship currency. This, your level of you know, moving the needle and and and hitting these milestones have now put you in, you know, different kinds of rooms. What has been your experience in terms of being in some of these rooms, right? Now that you have been invited in, you know, maybe as a YC founder and then later as someone, you know, who raised a series A and then a series B. tell us what your lessons are in terms of people that might struggle with

I'm in this new room. I don't necessarily feel like I belong and and maybe start the second, you know, second guess their their their confidence or f a sense of I should be in this room and what they might miss out on if they don't realize, you know, what you've realized. I think I think the the moral story is just just be yourself. You know, like a a lot of people say that, but that's the truth. You're in the room because you were yourself and if you tried to, you know, coach with a switch up, you know, then it's inauthentic and the people at that level

see it inauthentic, they realize inauthentic people really quickly. So I I I would say just be yourself. You got in that room being yourself and don't switch it up because you know people see right through that. And when you come across as not being genuine, I think that's a bigger red flag than you if you don't know something or or or or or if you're uncomfortable. but people I think appreciate when people other people

be themselves be their genuine self and that I think, you know, no matter where I I've gone, you know, I think that's the same Dave you're gonna get from Brooklyn the same Dave you're gonna get now. And and I think that resonates well. It might it might it might it might burn some people, burns like rub some people the wrong way, but if it rubs some people the wrong way, those are not the people for you anyway. Hmm. So on la last one before we close out,

A lot of folks here are watching, they're very inspired, right? You're now on the other side. You're still building, you're still growing, you got big plans, big visions, you know, and and and got a lot of room to to to see those things, you know, i manifest themselves. But, you know, it comes down to kind of this philosophy at the end of the day where we have to push ourselves to take some type of calculated risk so that we untether our time from our money, right? And so whether someone is looking to be a founder.

Or maybe there's another avenue that might be better suited for them based on their risk tolerance. What have you learned kind of looking back now and just the the general philosophy around wealth, around kind of why people should be thinking beyond just their current ability to pay bills and really think about, you know, generations to come. And even, you know, to the to the extent possible, how you feel the landscape may be shifting where this conversation is maybe a little bit more urgent than it was or felt like, you know, five, ten years ago.

I think that we're living in one of the greatest moments of civilizational transformation and wealth creation ever in human history. there's been, you know, s several of these moments. This is probably the biggest one. and I think that the fact that all your audience and you know are secluded that, you know, we're alive during this time in the game, you know, ability have the ability

to to be in it. whether working at a company, starting a company is just stuck so fortunate. You know, we could have all been born a hundred years ago or even worse, 200 years ago. so I just kinda keep try keep that perspective. and I think that there's gonna be so much wealth cre cr created and and and everyone on this call hopefully will be able to think about ways that they can be part of it and attach themselves to it.

And ultimately to your earlier point in the beginning of conversation, it is going to be related to, you know, ownership of of of capital. That that's that's what it's gonna take. And you know, people need to think about based on what they know, based on their skills, based on their experience thus far and their abilities, how can they best be be a part of this? and make sure that they they that they find some way. I I would venture to say that most of the folks probably, you know, in the audience

have already beaten the odds to get where they are at this point. You know, the odds were were kinda against all of us in the in this country. so so if you've beaten the odds before, have confidence in yourself that you can continue to do it. that's something that, you know, we we we say a lot, you know, at Squire like we've been beating the odds since inception. and and that's why, you know, we're so confident that we're gonna continue to and we're gonna be able to have a really big amazing outcome.

So, so yeah, so this is the time to do it. This is the time to take the risk. the bigger risk is not is is is is not doing it. and this is really an exciting time because it's just so much change. There's a lot of uncertainty though. You gotta be comfortable with it. No one knows what's gonna happen a week from now, let alone a year from now. but you gotta embrace that uncertainty and and and really, you know, make sure that you're you're you're in this game right now 'cause it's an exciting time to be a player, you know, in this game.

For sure. Dave, final words from you before we end this thing. Yeah, I mean, I think if you're on the fence, lean forward. And that's kind of what I'm saying. Like, you know, the biggest risk is not taking a risk. And if you want to start something, you've been waiting to start something, the time is now. There's no better moment than the present moment. And sometimes it takes you just taking a leap of faith and doing what you have to do. All right. This is from coming from guys who

Taking that risk, taking that that leap, showing you it's possible, doing it in an authentic way. Again, brothers, I know you got lot going on. A lot of gratitude for you taking the time to share some of this wisdom with the next generation of of of founders. Go support Squire, you know, avocado advocate for these guys to achieve that next level of success because these are the type of guys that will come back, give back, and create something that's gonna continue to aspire. So with that, audience, give Songe and Dave.

a virtual round of applause for joining the Owner Mode Summit. Appreciate you guys. We'll talk to you soon. Take care.