In short
Podcast Summary: Earn Your Leisure - How Two Friends Built a $750 Million Barber Tech Company
Episode Overview In this episode of the *Earn Your Leisure* podcast, hosts Rashad Bilal and Troy Millings interview Songe LaRon and Dave Salvant, the co-founders of Squire, a barber shop tech platform now valued at $750 million. The discussion centers on their entrepreneurial journey, the challenges they faced, and the innovative solutions they created within the barber industry.
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Key Themes and Discussions
Introduction to Squire
- Concept: Squire is a tech platform revolutionizing the traditional barber shop experience by allowing customers to book appointments and manage payment processes seamlessly.
- Founding Story:
- LaRon and Salvant met in New York and brainstormed ideas for impactful businesses while working in law and finance.
- They recognized the inefficiencies in the barbering industry, where booking appointments and payments were cumbersome.
Early Challenges and Solutions
- Initial Development:
- They built Squire without deep technical skills, opting to recruit a technical co-founder instead of outsourcing development.
- They conducted customer interviews to refine their product and ensure it met real needs.
- Free Service Period:
- Squire was offered for free for three years to gain product-market fit, allowing them to build a user base.
- Revenue was generated through transaction fees rather than subscription models at the beginning.
Fundraising Journey
- Angel Investors to VC:
- Discussed the process of fundraising, including the difficulty of securing investments and the importance of building relationships with angel investors.
- Successful Series A round raised $8 million after many rejections, emphasizing the need for persistence.
Scaling the Business
- User Growth:
- Squire scaled to serve 32,000 barbers and 10 million customers, a testament to their effective business model and marketing strategies.
- Marketing Strategy:
- A mix of word-of-mouth referrals, trade shows, and community events helped promote the platform.
The Role of Y Combinator
- Participating in Y Combinator provided access to resources, mentorship, and credibility, which were valuable in raising subsequent funding.
Technology and Innovation
- Incorporating AI:
- The conversation highlighted the importance of AI in improving operational efficiency and customer experience.
- They introduced features such as automated scheduling and marketing tools to enhance barber shop management.
Ownership and Control
- Equity and Governance:
- Discussed the dynamics of equity dilution as they brought in investors and the importance of retaining control despite losing majority ownership.
- Founders' Vision:
- Emphasized that building a sustainable, high-quality business is key to long-term success and potential exits.
Future Directions
- Global Expansion Plans:
- Interest in exploring international markets, recognizing that the barbering business model has universal appeal.
- Continued Innovation:
- Focused on leveraging AI further to empower barbers and enhance customer interactions.
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Key Takeaways
- Persistence is Key: The entrepreneurial journey involves facing numerous challenges and rejections, but resilience and adaptation can lead to success.
- Community Orientation: Building relationships within the community is crucial for growth, especially in industries like barbering that thrive on personal connections.
- Tech-Driven Solutions: Embracing technology and innovation can create significant efficiencies, even in traditional industries.
- Equity Considerations: Understanding the implications of equity dilution and maintaining control is vital for founders as they scale their businesses.
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Conclusion The episode offers valuable insights into the entrepreneurial journey of Songe LaRon and Dave Salvant, highlighting their innovative approach to transforming the barbering industry through technology and strategic business practices. Their story serves as an inspiration for aspiring entrepreneurs in any field.
For further information and resources, listeners can visit [Squire's website](https://squire.com).
Hashtags: EarnYourLeisure #Squire #Entrepreneurship #TechStartups #BlackFounders #Fundraising #AI
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
Automatic transcript. May contain errors.0:00This is an iHeart Podcast. Guaranteed Human.
0:32aka neurolinguistic programming. Is it a self-help miracle, a shady hypnosis scam, or both? Listen to Mind Games on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. This season on Dear Chelsea with me, Chelsea Handler, we've got some incredible guests like Kumail Nanjiani. Let's start with your cat. How is she? She is not with us anymore. Okay, great, great, great way to start. Maybe you will cry. Ross Matthews. You know what kids always say to me? Are you a boy or a girl? Oh my God. All the time. That's so funny. I know. So I try to butch it up for kids so they're not confused.
1:07Yeah, but you're butching it up. It's basically like Doris Day. Right? No, I turn into Bea Arthur. Listen to these episodes of Dear Chelsea on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hello, hello, all my people. What's up? It's Questlove. Recently, I had the opportunity to sit down with the one and only ASAP Rocky. He reflects on his journey from Harlem roots to global icon status and discovering the hip-hop origin of his name. The ledge was on the TV. Rakim had the Buckethead Kangol join on. I'm possibly like, that's Rakim. That's who you named after. I just, damn the f*** I swear.
1:46Listen to The Questlove Show on the iHeartRadio app, Apple Podcasts, or wherever you get your podcast. Run a business and not thinking about podcasting? Think again. More Americans listen to podcasts, then add supported streaming music from Spotify and Pandora. And as the number one podcaster, iHeart's twice as large as the next two combined. Learn how podcasting can help your business. Call 844-844-iHeart. A new year doesn't ask us to become someone new. It invites us back home to ourselves. I'm Mike Della Rocha, host of Sacred Lessons, a space for men to pause, reflect, and heal. This year, we're talking honestly about mental health, relationships, and the patterns we're ready to release.
2:27If you're looking for clarity, connection, and healthier ways to show up in your life, Sacred Lessons is here for you. Listen to Sacred Lessons with Mike Delaroach on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. This episode is brought to you by PNC Bank. A lot of people think podcasts about work are boring, and sure, they definitely can be. But understanding a professional's routine shows us how they achieve their success little by little, day after day. It's like banking with PNC Bank. It might seem boring to save, plan, and make calculated decisions with your bank, but keeping your money boring is what helps you live a more happily fulfilled life.
3:08PNC Bank, brilliantly boring since 1865. Brilliantly boring since 1865 is a service mark of the PNC Financial Service Group, Inc. PNC Bank, National Association, member FDIC. When I did the podcast with you all, I was telling you, probably the most impactful interview I've done in my career. Heroes now. Real heroes. I heard Rashad and Troy talk about the tax letters. We talk about finance, but we talk in a language that is common to the people that's from the community that we grew up in. You all are the bright spot of real estate and entrepreneurship for black Americans. This is the knowledge that actually matters.
3:52I applaud both of you for this. Thank you. Literacy isn't a country issue. It's not an American issue. It's a world issue. He came to earn our leisure.
4:08All right, guys, welcome back. EYL. You got a special episode, you know, long overdue. friends of ours and people that have really built tremendous business and really revolutionized the industry that for a long time kind of was in the dark ages when it comes to technology and the barbershop, we think a barbershop industry. So yeah, we got a song in David from Squire. If you're not familiar with Squire, that's an app that actually allows, well, I'll let you guys talk about it, but how I know it is it's an app that allows you to book for appointments for your barber right it allows the barber to manage the schedule to run a barbershop like an actual operation right um what's the other tech that's behind it as well that allows another part that's important is the payments so we make that you know really really simple and easy uh kind of like that experience when you take an uber you just get in you know do your ride and then get out you know we have to worry about tipping and cash and all that we take that kind of experience like to the barbershop as well.
5:11Yeah, I mean, and when we started this business like nine years ago, you know, it was nothing. Uber, 2015, 2016, Uber was just getting traction. And the experience of going down to the barbershop, having everything handled, just walking out after, we just wanted that seamless experience. And then we realized once we were in the business, the real opportunity was streamline the entire operations of the business. so that's kind of how Squire was born as a full management system that it is today and the valuation right now is 750 million yes congrats so congratulations thank you first and foremost thank you guys for joining us man appreciate it thanks for having us we run into y 'all a lot Dave I feel like we run into each other all the time so it was good to have you out here man and like you said something that's disruptive but has helped our community for sure in lots of communities get back time, which is the one asset that you can't replicate.
6:14And you guys have done that. So congratulations. Thank you. Thank you. All right. So let's get into it. So, okay. You guys start an app, which seems like somebody should have been to that, right? It wasn't something that was like too far out of the realm of like thought process as far as being able to book online, being able to process payments correctly, being able to manage appointments for barbers like it it seems like something that you know should have been in existence right um but it wasn't so walk us through a how you guys developed the relationship and the process of actually coming up with the idea and then getting the idea off the ground and to market yeah so dave and i we were friends before actually starting squire uh we both were in new york i was working at a law firm at the time and he was like in finance so we we had a lot of friends in common going out you know we're in our 20s at the time and um after a few years we were like really wanted to work on something that would be more impactful and we weren't really kind of fulfilled with the corporate trajectory we were on so we literally brainstorm ideas on the weekends instead of going out we used to sneak into uh columbia campus because we both lived up uptown in Harlem and uh we were literally just white whiteboard ideas like what could we work on what could we do that would actually you know could have a legacy that would have a bigger impact on you know on communities and just be more positive and um through that process we came up with this this experience of the barbershop like both of us have been going to barbers since we were kids you know I started going like around six or seven with my pops back in the day and um the the experience of getting haircut hadn't changed 20 years later you go in you wait it could be 10 minutes it could be two hours uh you might you know you have to pay of cash you text back and forth with your barber and didn't make sense that this one experience of life that was like so important and and so like joyous and one on the one hand was also so painful um so that that's why we came up the idea like how can we solve this with technology everybody got the experience when uh you go to a barbershop there's a big homie comes in and be like he's next i've been sitting for three hours everybody has that experience and you know like that used to happen to me all the time with a little kid because you know i grew up you know i used to go to barbershop by myself because mom was working or whatever the case may be but with technology now you can't do that because everything is regimented everything is uh on point and that's a harder that's harder pill to swallow for the barbershop owner barbers to like say nah somebody else was next and and a matter of what happens used to happen all the time you make appointment at 12 and then even if nobody took your spot the barber's just running late so it's taking an hour and a half 45 minutes so you don't actually get into the chair until two o 'clock and it's like you you you can't really run your day by like kind of hoping and wishing that there's a 90 minute window that you might potentially get so if you have set slots every hour, right?
9:15Like, that it holds, I think it holds everybody accountable. And I think it's done a job for barbers. It's made them more efficient with their time, but they're able to cut more efficiently knowing like, hey, I got somebody coming out there, let me be precise with this one, make sure I can get more people in, rather than wasting the time when it's like, yeah, I'm waiting for this dude, or you're next, who's the, I don't know is. They're actually becoming more efficient, which actually means more customers, more clients, more money. Absolutely. Absolutely. And now, you know, with the AI and being in Squire now and having the AI kind of like focus companies, the tools that we're able to leverage now is just incredible.
9:58Like we built Operator, which, you know, I demoed at LV Barber Expo. It's a way for barbers to never have to answer their phone. You know, people just call the barbershop and this human-like voice picks up and does all the scheduling for you and really is able to, like, do, like, the operations that normally a human would do. So we just, it's just making the barbers and the barbershop owners' lives more efficient. And efficiency leads to more money at the end of the day. When y 'all first figure out that you're going to create a solution for this problem, where's the first shop that you go to to tell them about this technology that you're about to use?
10:40Do you go back to the same spotlight? Yo, bro, I'm not sitting here for three hours. Here's this product. How did that go? So the thing with that is what we did was we went out. When we first had the idea, then we went out with an iPad and just asked questions. If we would build this thing, would you use it? Ask for feedback. you know, interviews. And like, it's hard to tell somebody no when you're already been involved in the process all along. So, so what we did early on is we built with the guys or with the owners and we had them a part of the process. And then when it was time to launch, you can't really say you're not doing this because you were lockstep the entire process.
11:26so let me ask you this as far as um the idea it's a relatively it's not a complex idea right but what's what does it take to actually get that tech to make it come to life and make it the application actually happen like how much money does that cost and what was the process as far as on the technical side to actually make that app get up and running and actually in the app store Yeah. So when we were at that stage, you know, this was like almost 10 years ago, there was no vibe coding at the time. It was a total different world where it was a lot harder to build that first like MVP, first version of the product to get in front of the customers.
12:07So the approach that we took was we wanted to recruit a co-founder to be technical that's like part of the team instead of outsourcing and like paying. And, you know, some people do it in different ways. But our philosophy was always like if you're paying somebody to build your product, you have inverse like goals. Like they want to do it for as fast as possible and make as much money as possible. And you want to get the best quality and pay as little as possible. So you're already kind of set up for failure. so um we were really focused on recruiting somebody to be our cto and co-founder and it took some time um and we went through some you know a couple iterations where like it didn't work out but eventually we did find that person and that person kind of joined the company at the time and and helped us build that first first version of the product yes you guys don't come obviously you're in law you're in finance how in depth did you have to get in the technological side right Because you're trying to build an app that is going to, obviously, you're going to recruit people to find.
13:06But how much did y 'all have to get in the weeds inside of tech to realize that, you know, we have to understand this industry just as much as the one that we came from? It was a learning process. Like, we didn't know anything about tech, had never, you know, started a tech company, didn't have any connections in tech at the time. So, honestly, we didn't know what we were doing. What we did have is pretty good product instincts because we were so close to the customer. So we understood the pain points and kind of like what we were trying to solve for. But in terms of under the hood and the actual process of like building something and like actually like building the first version of the app, which was an iOS app, we were completely clueless as to what was actually happening.
13:47Yeah, and it's a consumer-facing application. So, you know, directionally, we know what felt right in terms of like what a product actually operates. But in terms of like under the hood, we didn't know anything. I mean, how would you know? Like, you're just starting out, you have an idea and you're like, I want to go build this, but you don't actually know like what it takes. Now, of course, we've learned a lot. But that, you know, further was like more reason why we wanted to have somebody on the team who was aligned incentives and could help build it out. because when you're non-technical, especially back then before AI was the way it is now, like it's very difficult to like understand from a technical process, like what is actually required.
14:31Like something could take a day and they could say it takes a month. You have no idea. So you're really at it. There's an asymmetry of like knowledge at that point. So when I talk to early stage founders who want to be tech founders and want to start companies, um i say you know either learn to code now you can learn a lot with ai and you can vibe code your way to a lot um but really like you want to be have someone on your team who has a strong technical foundation if possible so how did what was the marketing campaign as far as to get barbers on board was it to get barbers on board was to get the clients of barbers on board like what was the first you know we did everything under the sun but uh it was us so so what happened in the beginning is we thought that if we built this beautiful application and folks started to use it everything would run smoothly the barbers love it the customers love it it'd be our early financial models had us get into 10 billion dollars in three years but but that's but that's before ai but but uh what was interesting is it didn't work you know it didn't work meaning that But when we sent customers, barbers would use it as a client acquisition tool.
15:48And it would be a janky experience for the user. So folks would come in and a barber would have them pay twice in the app and in the store again because he or she didn't trust the application. So there was stuff like that. There was double bookings. So even though we would say, hey, use this for all your appointments, he would then or she would then just keep on taking appointments away from existing customers. So we realized that if we didn't have the entire back end for the entire barbershop, we would still run into these problems over and over again. So we had to make sure all the appointments in the barbershop went through this system.
16:31So that was the first kind of unlock of like, hey, we're not just building an app. We have to build a comprehensive system that manages everything through the barbershop. So you targeted the barbershops. Yeah. Did you give it out for free at first? Absolutely. So we were literally, he and I, walking to every shop we could, like near our office in New York or near where we live. Like we were just like walking ourselves, wait, talk to the owner, try to get them to use the app. sometimes you know they didn't want to hear hear from us because they were like you know like what are you selling kind of kind of thing especially in new york and sometimes we had to actually like book a service like what's the cheapest service you got or a beer trim all right i'll pay you for that time and then when you're in the chair you can talk to them and kind of get their attention uh so we it was really like hand-to-hand combat how many how many did you give away for free first before you started i mean we didn't start charging uh for the software until like 20 2018 so how many three years three years just yeah just basically um here but we made money on the like the the transaction so it's like hey we still have some revenue coming in but you know in the first you just gotta when you're unproven when it's a new uh motion you gotta give it away free to get product market fit okay so how did it most people probably thinking like how do you guys make the money so the transaction fee there's a percentage that goes from it then the the subscription from the barbershops that use it, that's how you built the business model?
17:58Yeah, yeah, yeah. How much is that? How much is the subscription right now, like today? So it's$100 to$250, depending on - A month? Yeah, a month. Yeah, depending on what feature set you have. It starts at$30. The individual partner starts at$30. Oh, yeah. So if he has his own salon, that's just like - So now there's the business part of it. Like you're making the money, but you're giving it away for free, but you're trying to get it on ios it's ios you said yeah so you know that apple's got coming for that 30 how did how are you guys envisioning this and you're bouncing it to say all right we need to make revenue we're giving the product way for free yes we're making some from the transactions but we need to keep the business alive well you know that's where um earlier when you're that early before you're like making meaningful revenue um if you're able to raise money that kind of that Capital infusion is what keeps the lights on.
18:51And we were fortunate to be able to raise some angel rounds from our network of people who we knew. Not big checks, but from anywhere from$20 ,000,$30 ,000 up to$100 ,000. So that was our first capital that we were able to raise. And that sustained us over the first two or three years, just these angel checks that we were getting from people we knew. and um because the revenue wasn't we were definitely not making enough revenue to like support the business was that was that a space that y 'all were familiar with because angel invest i mean it's not common to a lot of people in our community it's a network you know one of the guys that gave us a big you know sign of approval early on was richard lou dennis uh he invested money uh when we didn't have anything because what we had some traction but not a lot traction compared to today but with venture you know uh and the way we did it because we didn't have access to these traditional networks we used to just build something get a little traction look what we built give us some like go out to our network get some more traction go out to that network again because you know back then it was very it was very difficult to raise you know money like for over four years it was just this piecemeal type of thing um we went to y accommodator uh which is a big inflection point in uh 2016 so we're able to raise some money out out of that but uh we were very fortunate uh because a lot of folks back then didn't didn't make it but because of our network because of our pedigrees uh because of the hustle mentality we were able to kind of just raise some money so at what point do you start like the pathway that being valued at 750 million dollars right that comes from you obviously had multiple rounds of being raising money right and then you have revenue coming in as well so when does it start becoming like profitable as far as okay this is now a real business that we're running full-time yeah say around the time we raised our series a which was 2019 uh that was the first institutional money um so so meaning like a big like firm that um that will give you you know one check that would be enough to sustain you to get to the next.
21:07How much was that? That was for$8 million. $8 million. That was the most money we ever had at once. And the first time we ever had enough to not be worried about fundraising. So what made them value the company enough to raise, to give you a check for$8 million? Yeah. Future valuations based off of revenue models? Like what was the... So to raise a Series A, you know, typically at that point, they want to see signs of like consistency. consistency um so like a consistent go-to-market motion um that you you're making um what's called ARPU like average revenue per user that is it was consistent so they can kind of see a pathway of like okay if they can get to this um we can we can see how they can get to that you know a bigger level uh typically back then it was like um if you can basically a million dollars in annual recurring revenue used to be the kind of milestone when you when you were about ready for a series a And that's where we were at that time.
22:02I think now that goalpost has moved from what I've heard for early stage founders. But back in 2019, that was it. So we were doing a million roughly in ARR. We had a consistent sales process that you could see how our pool would grow over time as the shops were coming on to Squire. All of that was evidence for an investor to see, OK, if they can do this, I can see how they could get to$10 million,$50 million,$100 million. because they have like a process that's reputable that makes sense how was the retention rate for you guys early stage into the series how was our retention then it's a lot better now we love it i mean so even even even that fundraise was difficult like i just think back like it was a a fundraise from hell like i think um we had about 60 meetings and got like one term sheet like one offer you know and based on the numbers i mean we should have had at least four or five in my view so so it was not an easy process uh with all the credentials with all the backing of y combinator we went through a y combinator series a program and we still it was still difficult so okay how did you know the process of actually even going through to try to get venture capital money Did you have a mentor that was like ushering you through these different meetings or you just cold calling different firms?
23:28Yeah. So as Dave mentioned, we did Y Combinator in 2016. So when we did that, we moved to the Bay Area. We moved the entire company kind of there and we went through that process, did that. So then fast forward to 2019. At the time, Y Combinator had a Series A program. Can you explain Y Combinator for people that may not be familiar? Yeah. So it's what I would call like the preeminent accelerator program for early stage startups based in Silicon Valley. Some of the people who are affiliated with us are essentially like the highest echelon of tech. Like, for example, like Sam Altman was there when we were there.
24:10So, you know, we got to know him pretty well. Michael Seibel is a mentor of ours and, you know, used to run the program. One of the co-founders of Twitch. You know, pretty much they are like the biggest name in tech for early stage companies. And so when you have that stamp of approval, it's equivalent to like going to Harvard or Stanford or something in the tech world. So it was a big deal when we did it. And then 2019, at the time, they had a Series A program. So for the companies that went through the core program that they thought were like ready for Series A, you could kind of apply and then redo it before Series A.
24:52So they would help us like set up investor meetings, connect us with the right people, help us with our pitch. So we had about as much help and support as any company could have in raising a Series A. and to Dave's point you know we still had you know 60 meetings of different VC funds and 59 rejections and we ended up getting one and that's what allowed us to get to the next level but all you need is one that's it all you need is one what was that process like we talked to a lot of people who've created businesses and founders that moment when you take on money right before it was just you guys and you got a CTO and now you have investors that you have to answer to and, you know, make sure that they're on board with what's going on.
25:38What was that process like for y 'all? Was that an adjustment phase? For sure. For sure. It was the first time. So when you get in an institutional fund that invests, usually they want a board seat. So that was the first time that we, you know, had an actual investor on our board and had to start being more formal in terms of having like board meetings and reporting and all that stuff. So at the time it was a bit stressful, if I'm honest, and it was, it was a change, but in retrospect, it definitely made us mature as a company and mature as founders. So, so it was a healthy thing for the company, but it's, it's increased scrutiny.
26:18Like now you're, you're, you're literally accountable, responsible every quarter. You have to report how you're doing. And someone who's kind of, in a sense, a little bit over you because they, you know they they're the board um is like saying you know giving you feedback and and really pushing you to go further so uh yeah it was a big change and the best board members you know i think are um super helpful because they can use their experience as an operator and or their experience from other boards that they sit on so so you know sometimes you don't agree with with what they are saying in the present moment, but, you know, there's been times like six months, a year later, I'm like, Hey, no, maybe it made sense, but I didn't see it because you haven't experienced that or you haven't lived through that.
27:09So what, what mistakes did you make or what lessons did you learn as far as in pitching your, your company to VC firms that if you, if you did it now, you might do differently. so so i think what separated in the early days and we really struggled with getting them excited about the opportunity and later on when we got better at it is is the size of how big can get um i think a lot of particularly a lot a lot of founders you know from our from our communities like we tend to be like very practical and like we want to paint a vision that we think we can really achieve but like the ethos of like particularly like silicon valley is like you have to go big you have to have the biggest possible vision imaginable and sell that because that's what gets people excited um you know they get excited about you know how can this company be a billion dollar company or a 10 billion dollar company or 100 billion dollar company so in the early days like it was it was hard for us to like make our narrative shape our narrative to fit something so big.
28:17Over time, we started getting better at it. And over time, the more data, the more that we learned about our business, we started being able to see a pathway like, okay, this is how we get to 100 million in revenue. This is how we get to a billion plus valuation. And then if you believe it, they can believe it. But if you can't even see it, the investor's never going to see it either. Is that the goal? Did you guys sit down one day, obviously as the vision becomes clear and say, yeah, we're going to be a unicorn. We have the potential to do it. Believed it. I mean, but it's communicating it. And Silicon Valley, it overemphasizes the outliers.
28:52You know, like the whole business model, the whole VC model is outliers. They want the folks that are like the 0.1 of 1 % because that can return the fund. And, you know, if you invest, so the math is the math. They don't, out of 10 portfolio companies, one, they hope one is going to be that 100x return. and a 100x return will pay out the payback to fund and make the individual partner very rich so you have to understand that so if you don't if you don't like pitch a 100x type of opportunity then it just doesn't excite them as much how does it look for forward revenue for you guys in terms of valuation like what's that forward multiple is it like a four five ten it honestly it varies and there's so many factors that like macroeconomic factors so the last fundraiser that we did was in 2021 and that was a very different climate um interest rates were super low it was like what they call like the you know zerp era where the interest rates were you know something was almost zero um so as a result like there's an inverse relation on on uh multiples so multiples were just much higher across the board for all companies and you know that that gives and takes and that changes with the economy so our focus is always on building a really great business if you build a great business that fundamentally is strong has great unit economics and a pathway to like being really big regardless of the economic climate like you're gonna be successful that was one of those things and Dave I'll let you finish it was like if you create a business make sure you have these components right so make sure you have the tech component consumer like all those components as you're doing it are y 'all checking off the list like oh we have all those things yeah I mean yeah I think so and I think you know The more we learn about our business and the more mature we get, we see, okay, fundamentally, this is a really solid, strong business that's going to endure.
30:47And the great thing about our customers is that people keep getting haircuts. It's very resilient. If there's an economic downturn, actually, people tend to get more haircuts because it's one of those luxuries you can afford even if you're not making as much money. So I think we're really well positioned to continue to thrive, like kind of regardless of what happens in the economy. Yeah, I want to. So a couple of things. And we're seeing that I was at a dinner last night and a seed early stage and they're raising 200x revenue, these AI companies. So it's just it just shifts with the tide, you know.
31:28So it's still there if you're the hot company, a hot industry at that time, and it's competition, people pay whatever, irrational. So that's one thing. And the second thing I want to go back to is like, you know, paying the vision. A lot of folks, you know, because we're two black founders, thought we were just focusing on black barbershops. And, you know, we made it really clear that we were not. In fact, in our early pitch decks, There was no mention of everything was like these hipster type barbershops so people can relate to because most of the investors that you were meeting were not of color.
32:10So we had to make sure it resonated with them. And those little social cues that you pick up on that you need to kind of incorporate to the story to make it seem like, hey. And then still some investors said, are you guys still targeting black barbershops? when, like, it just didn't make any sense to me. And, you know, I get it, but, like, you know, we made it really clear that we were going after the entire market, not just a slither of the market. What's the percentage of barbershops that you think you have that are not black? I mean, I think it probably matches the population overall, so probably 80%.
32:55so marketing to barbershops right are you marketing at the beginning you were the face you were going in hand in hand so were you doing that what white barbershops also absolutely well how did that work out so funny enough when we were first kind of thinking through how we're going to do this we had a bias against ourselves we thought we probably couldn't go in there and resonate with these non-black barbershops. So we ended up hiring a friend of ours who's actually still with the company, who's white. And his job was going to be kind of biz-deb, like going to the shops. So he was doing that. We were still doing it.
33:37And over time, this experience, we started finding out that actually we were better even at the white shops selling them than he was. And some of the bias that we had, you know, the preconceived notion that we had that these shop owners, because we didn't look like them, weren't going to want to hear us out, actually was just totally not true. And then, you know, and it turns out, you know, the white guy who we hired wasn't good at that. He ended up being really good at other things. So he moved into like product on the product side. So you just never, you never know. And sometimes there's a tendency to sell yourself short because, you know, you think somebody is going to think something about you.
34:13But if you have a great product and you go there and you meet them eye to eye, you know, we found that for the most part, customers are willing to hear you out, you know, regardless of what you look like. Yeah. Are you solving the hair on fire problem? You know, and if you're solving that problem, I don't care. Whatever you are, I think they're going to listen to you because you're addressing a real pain point in their lives. All right. Correct me if I'm wrong on these numbers. 32 ,000 barbershops? 32 ,000 barbershops. Yeah. Barbers. Barbers. 10 million clients last time i checked yeah somewhere in that range how are we every january we're encouraged to start over but what if this year is about slowing down and learning how to understand ourselves more deeply what if this year is about giving ourselves permission to feel what we've been holding and knowing that it's okay to ask for help i'm mike de la rocha host of sacred Lessons.
35:10This is a podcast for men navigating stress, emotional health, fatherhood, identity, and the unspoken pressures we're taught to carry alone. We talk honestly about mental health, about healing generational wounds, and about learning how to show up with more presence and care. If you want a healthier relationship with yourself and the people you love, then Sacred Lessons is the podcast for you. Listen to Sacred Lessons with Mike Dallarocha on America's number one podcast network, iHeart. Follow Sacred Lessons with Mike Dallarocha and start listening on the free iHeart Radio app today. New year, new goals, and in this economy, a better money plan is more necessary than ever.
35:55I am Matt. And I'm Joel. We are from the How to Money podcast, and every week we help you to spend smarter, save more, and make sense of what's going on out there. If you want 2026 to be the year you finally feel in control of your money, we're here to give you the tools and advice to help you make it happen. Listen to How to Money on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hey, what's up, y 'all? This is Questlove. Recently, I had the opportunity to sit down with A$AP Rocky ahead of his album release, Don't Be Dumb. He reflects on his journey from his Harlem roots to global icon status, discovering the hip-hop origin of his name.
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36:31The ledge was on the TV. Rakim had the bucket hat can go during the pasta. Like, that's Rakim. That's who you named after. I just was like, damn, that **** got swag. Rocky offers a window into not only a boundary-breaking artist, but as a man committed to fusing creative ideas, community, and remaining unapologetically himself. Have you ever gotten roasted for any of your outfits? For sure. Some people don't be getting the vision. Look, they can roast me. They can cook me. They can deep fry me. They can saute whatever they want. there's nobody who can f*** with my fashion sense and my taste is impeccable.
37:09I'm just like, I impress myself a lot. It's an amazing conversation. One you definitely don't want to miss, so listen to the Questlove show on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. What if mind control is real? If you could control the behavior of anybody around you, what kind of life would you have? Can you hypnotically persuade someone to buy a car? When you look at your car, you're going to become overwhelmed with such good feelings. Can you hypnotize someone into sleeping with you? I gave her some suggestions to be sexually aroused. Can you get someone to join your cult?
37:47NLP was used on me to access my subconscious. NLP, aka Neuro Linguistic Programming, is a blend of hypnosis, linguistics, and psychology. Fans say it's like finally getting a user manual for your brain. It's about engineering consciousness. Mind Games is the story of NLP, its crazy cast of disciples, and the fake doctor who invented it at a New Age commune and sold it to guys in suits. He stood trial for murder and got acquitted. The biggest mind game of all? NLP might actually work. This is wild. Listen to Mind Games on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. This season on Dear Chelsea with me, Chelsea Handler, we've got some incredible guests like Kumail Nanjiani.
38:35Let's start with your cat. How is she? She is not with a thing. Okay, great, great, great way to start. So this is a great beginning and hopefully you'll be able to, I don't know, maybe you will cry. Amanda Seyfried. Life is so short. if you feel something like that, you have that fire in you for this experience. It's not for a guy. It's for the experience of being in love. And like, it's bigger than a guy. Elizabeth Olsen. I love swimming naked so much. And I know you love taking pictures of yourself naked. I love to be naked. I just want to be in my brown underwear all the time. Ross Matthews.
39:10You know what kids always say to me? Are you a boy or a girl? Oh my God. All the time. That's so funny. I know. So I'm always like, hi. I try to butch it up for kids, you know, so they're not confused. Yeah, but you're butching it up is basically like Dora's Day. No, I turn into Bea Arthur. Listen to these episodes of Dear Chelsea on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Like, this is great, because you're talking from 2016 to this point. How are we scaling year to year? Like, what trends are you watching to say, all right, here's an opportunity, here's an opportunity.
39:44This is a demographic. We haven't touched this. But how are y 'all going about that? That's a lot. Congrats. Thank you. Thank you. Thank you. It's never enough, though. There was more. Let's get to the next. So what we learned is what's super important to scale is that you really have to scale your team. So, you know, in the early stages, you know, it was us and then a few other early employees. But as you get bigger, you really have to bring on folks who have the experience of kind of getting to the next level where you're trying to get. and over time we've built up a really incredible kind of bench of our executives and that that has helped you know helped tremendously and in the early days you do you know it's called doing things that don't scale like walking into the barbershop yourself and pitching them like that's great and but like you can't that's not going to get you to where we are now so over time you have to figure out how do you build like repeatable motions repeatable processes that's like scalable and you know that's essentially what we've been able to do so as far as this number of$750 million valuation can you break that down as far as like what does that actually mean in layman terms for somebody that they hear that but it's like that is the enterprise value or the kind of like market cap of your business so if somebody were to purchase the business they would have to pay$750 million for an entire business.
41:17And if somebody's investing, you know, based on the dollar amount they invest, that's a percentage amount of the$750 million. And that$750 million would come from investors valuing the company at that as far as, okay, I'm going to put this amount of money in per percentage and then that equals the$750 million. Or does that come from revenue that is projected to be like, okay, 10x revenue. I mean, there's some formula that they create, but that's essentially the formula. It's like, hey, look, for 1%, it's 7.5 million. So you times that by 10. If you want 10%, you've got to put up 75 million. So that's kind of how the math works.
42:00And it's just supply and demand. uh you know if you have a great product if you have some proprietary technology that they think might you know transform the world they're gonna they're gonna pay whatever they're gonna pay for it's just like you know what the company what people think the company is worth how does the ownership table look right because a lot of times startups you know we don't have money right we haven't gotten venture capital and so a lot of times people offer equity right like as an exchange or collateral to say, hey, I need you part of the team. How does ownership look then?
42:38How does it look now? Obviously, you've got a board, you've got investors. Are you guys majority owners still? How does this work? Yeah, so as far as the equity, all of our employees have some degree of equity. We think that's important. We think it's important, one, to align incentives, and it's also important as a wealth-building mechanism. Our company is, I don't know for sure, but I would say it's probably maybe the most diverse or one of the most diverse of a company like at our scale in terms of like the background of our employees so we think it's you know it's really important for them to have skin in the game and like when we do have the big exit you know hopefully we'll be creating a lot of millionaires and creating a lot of wealth in the community um so so uh so that's important um the second was the second part of your question ownership I think oh yeah yeah the ownership you get diluted I mean it's natural um you know it's the the pie gets bigger, but your percentage of the pie goes down over time.
43:35So, you know, unfortunately, I wouldn't say we have a majority, but, you know, that's just kind of the name of the game. Yeah, but, you know, control, I think, is also super important. Like, you know, when you go through this fundraising, take on more investors, you know, you lose control, but we still, like, a board can't get rid of us if they wanted to because, of the structure we have in place. And that's equally important is control. So the decision-making process, you guys still are able to make decisions without having to have input or? No, you get input and you take feedback. But to Dave's point, as founders are raising and bringing on investors, it's super important to understand the control provisions and control mechanisms with respect to majority of equity, but also board dynamics.
44:34So that's a lot of times people aren't thinking about that. And they raise money, they get these boards, and the next thing you know, they have a bad quarter, and then the board's like, all right. So can you explain that? Is there a set term that has to be in the contract to be like, okay, even though I'm not a majority shareholder, I still cannot be removed from board? I think it's pretty much just a couple of ways. it is like Mark Zuckerberg has this. We don't have this, but he has super majority voting. So essentially one of his shares equal like 10 or whatever shares that he has. And ultimately that's super rare what he has at a public stage.
45:13He can do whatever he wants and they just literally can't get rid of him. And you have to think about like, especially in the public markets, investors are quarter to quarter, very short term. You guys know this. But, you know, as a founder-led, you know, you're thinking three, four quarters ahead. So you might, you know, max out CapEx for a couple quarters, but your vision is, you know, this will ultimately pan out. And if you're looking at it from a quarter-over-quarter basis, you're not going to make those long-term decisions. So a supermajority is one. And then the second is board seats. So if you have the board controls the company, and if your investors have more board seats than you have, they can just vote you out.
46:04But in our scenario, we have the same amount of board seats as investors. So in any case, it's going to be kind of like a deadlock situation. Okay. So you mentioned the exit. And I think a lot of people get this misconstrued, especially if there's no education around it. Talk about the vision for that. Is there a number that we have in mind? And it's like, all right. And then obviously there's a board approval. Explain the process. Because we've seen people sell their businesses. And a lot of times they're like, oh, they sold out the business. They sell out. They don't understand the functionality behind creating a business, getting capital, and then saying, all right, we're going to exit potentially to start something new.
46:49It doesn't happen too frequently. Is there a number that we got in mind? Like, what's the vision for it? I think we just want to build a great business. I think our metrics is like, hey, the best businesses are bought, not sold. And if you continue to add value, continue to build, continue to drive revenues up and to the right, Like businesses will, bigger businesses or, you know, public markets will, will come calling. So I guess, you know, that's kind of what we're focusing on right now. And, you know, when it gets there, but, but like to answer you, to speak to your first point, Troy, is like capital has to be returned at some point.
47:33You know, like you can't just do this. If you take capital as investors, you've got to return the capital some way, somehow at some point. so you can't have these evergreen situations where you're just building because you know like there needs to be an exit at some point gotta pay back so how are you marketing this like I know you did the barbershop expo with Jay, shout out to him that's a way to get barbers on board I'm assuming you're running ads what is the main source of actually creating awareness to make sure that the message is being spread to all barbershops in a diverse manner? Yeah, so those are two big ways.
48:18We're really big on events. So we do a lot of trade shows. We do big trade shows like CT Barber Expo, which I know you attended, which was super dope. But then we do a lot of smaller events also. We do local community events. So we'll partner with a barbershop that's got a good reputation in a certain city or neighborhood and then invite all the other barbershops around and host things like that. And part of it is marketing, but part of it is also just kind of like being there in the community, showing up, you know, where our customers are and meeting them where they are. We do a lot of, you know, advertisements, you know, online digitally.
48:56Our customers are very active on social, particularly on like Instagram and then now like TikTok as well. So, you know, we try to be like, you know, where they are. And then a lot of it is honestly word of mouth. Like barbers are naturally very, very communal type of businesses. So like in every neighborhood, each shop knows all the shops around there. It's like hyper local. So we try to incentivize, you know, our customers to like share, squire, refer, refer other shops that they know. And like, it kind of spreads that way as well. And also we have a sales team out in Austin, Texas. and they reach out to shops on a daily basis.
49:42They monitor. Cold call? Cold call, but more so like warm leads. Essentially, they know where they are. They might meet them on a show. They might comment on that page, but they're also always sourcing opportunities. But I think the community there in that Austin office is incredible. everybody sits together. I think there's value now in office environments because I know a lot of people don't like it, but we see the value of people coming to work every day, being amongst people the same age as you, sharing stories, learning from each other in real time, I think is very impactful. And we're seeing it with the culture and also like the wins and the scale that we're achieving in Austin office.
50:39You guys created something when it needed to be created, right? So I remember having Squire early on and I'm like in a barbershop. My barber didn't have it. Really? Yeah, yeah, yeah. He was in the Bronx, Jamaican. You know, we stubborn. But that was a time when you guys were the only person doing it. And now, 2025, there are people who have apps that are similar. I wonder at this point, how do you guys look at the landscape from a competitive standpoint? What keeps you ahead? Like, what's the technology that gives you the mode to keep Squire at that valuation to keep growing? Yeah, no, that's a good point.
51:20At the time when we started, there were definitely, like, fewer people trying to go after this market. And then, you know, as we've been more successful, people see it. So they're kind of trying to get in. But most of the competitive landscape is still software companies that are really focused on salons, spas, yoga studios, everything. And then they also try to do barbers like on the side, but it's not really their focus. So part of our differentiation is just like we're so laser focused on building the best product specifically for this user base. And that allows us to go deeper and just build things that like a lot of these other companies, many of them are even bigger than us, aren't willing to do.
52:01But then now, like what we're really excited about is just this AI lens and really having like an AI first approach. What we see in the landscape is that there's a lot of attention and a lot of investment going into building AI solutions for like at the enterprise level for like big companies and then at the consumer level. but for the small business level like there's really not a lot of focus on bringing this like powerful technology like to these small business entrepreneurs and like that's where we step in like we think they were really well positioned to to do that and that's what we're doing um what was the most recent raise it was you had a d yes yeah 2021 okay so and that was tiger tiger global yeah so walk us through that that one like what was the difference between that series D and the series A and like what did you know how did that look?
52:52So we raised our series A May of 2019 we raised our B, C and D over the next 14 months so in a year we raised over 100 million dollars
53:11over a year technology was that right I don't know. I don't know. I don't know. So over a year, we raised about$100 million. And what happened was we got that first check, and we executed. We went fast. We started gaining a lot of customers. And the folks that passed on the Series A came back and let the B six months later. And then nine months later, we raised the C. And that was on the back of COVID. So when COVID went, COVID kind of was like an inflection point for us because we were the first company to waive subscription fees so we didn't charge our customers. Then we built things, tools that allowed our barbershops to operate during that time.
54:02So virtual waiting room because everybody was trying to do social distances. COVID forums because people need to check they haven't been to an area in two weeks or whatever the case may be. You know, access to, you know, access to, you know, the various government programs. So streamlining the operations to get the required documentation to get those, the federal government help. So in a matter of six weeks, we launched like four or five products. And then when everything opened back up, like we had a boom effect because we were community first. Our message was clear that we're not going to charge you subscriptions.
54:40and also we built all this product that made the lives of our customers better. So coming out of that, best month sales, because everybody had to use some form of technology now because of the regulations. And then we raised in September, we raised our Series C. And then 10 months later, we raised our Series D. And what was coming in is like we weren't pitching. People were just coming to us. So it was like a 180 from our Series A where we had to go out and do a lot of the pitching to, like, BC's pitching us now. So when you get the infusion of$100 million in a very short period of time, what did you do with the$100 million?
55:20We held on to it. You know, like, like. Bowling. Like, you know, like, we always remember, like, how difficult it was. Yes. So so I guess, you know, a lot of folks, they go out and they spend, they do all this stuff. I think we were very careful because we were of the of the school of thought that we didn't want to go out and have to raise again if we want it under because we've been on both sides of the spectrum where we had to really make it really difficult to us to raise. And then when we came really easy, we said, hey, we just want to easy, you know, like we just want to save this money, build a business, march towards profit.
56:01and if we want to raise, we will. But what does that look like? All right, for the average person, right? They think you get$100 million and it's one thing to get$100 million, but how do you deploy that properly? Because deploying$100 million is not as easy as somebody would think, right? So how do you know this is how much we're going to save to have reserves, this is how much we're going to put in the market and this is how much we're going to... Is there a team? Is there a board? The people that give you the money have stipulations on what to do with the money? Like kind of walk us through that whole process.
56:36Yeah, so they give you the money. The money is in the bank account of the business. So you can kind of use it as you see fit. But what they do is they're going to hold you accountable for kind of the growth and the performance of the business. So that's, you know, what you have to do is like really be measured about how you're spending it. and what it allows you to do is take more risks. So you can try to do things that you couldn't have afforded to do before to fuel that growth. Some things will work, some things won't work and that's kind of the nature of an early stage startup. So investors are usually pretty forgiving of that but ultimately when you raise a big amount, they're investing that based on where they think you're going to get to at a certain point and that's going to return their money and you're going to be valued at more than when they invested.
57:26So if you're not hitting those milestones and you're not kind of growing into that, eventually they will start being like, okay, like, what's up? This company's not performing well. Is there a time threshold that they put on it? Right? Like, if they invest in it, does it have to be... I mean, I think they want to see a growth rate. A growth rate. And rule of thumb is, for late stage, probably like at least 30 % year-over-year growth. Year-over-year. Yeah. As far as revenue is concerned. The revenues, you know, and they want to see revenue going up, And cash burn going down. So you're growing. If you're growing like 100%, it's different.
58:04But if you're growing like 30%, they want to see you growing 30 % but getting more efficient at the same time. Seriously, my thing about y 'all, and obviously the 32 ,000 barbers, I wanted to learn about the global expansion. We travel a lot. We were just in Dubai. I had to figure out to get barbers for the wedding. We're in Africa. how does this work are you guys do you guys have a global imprint and is that on the vision board to expand into the continent and abroad yeah yes so right now we are in other countries um we're in u.s obviously uk canada um so kind of english speaking for now i totally agree with you i think that the global opportunity is crazy because like there's barbers everywhere people getting haircuts everywhere and and the businesses don't vary that much but there's always like the cultural nuances and things that you need to think about um so long story short like i do think eventually there's a place for us to be you know i would love to be on the continent like um you know i spent some some time in kenya um yeah last year and just there were so many barbershops there and like every every time i'll go in there be like yeah when are you coming um so uh but also you know it's it's It's not easy.
59:22You have to really do it right. And it's easy to kind of mess up in Globe Books Mansion if you're not thoughtful about it. So it's not going to be in the near term, probably. But eventually, I see us being in way more countries than we're in now. Yeah, if you need a barber anywhere, just hit me. We have some London-based barbers operate in Dubai. but they're from London because we operate in London so you know everybody goes back from London to Dubai so you ever in the city you know having a barber just messes me in I'm sure they had Dave I've been pretty good at just referrals that's one thing like I feel like any city I never had a problem finding a barber because like the people that I know in the city I just ask them who's the best barber who do you recommend and it's never really failed me so far we're building we're building something like that to help that from a digital perspective you know like hey we have a city pages where you can go in a city and then you can look at all the barbers and then we have the referrals on that that's a product we launched last year and you can actually uh it's you can actually you can actually put video of their work and it's really really cool to see the videos and that's like a next level feature yeah because that would be good because like i mean fortunately for us we know a lot of people yeah but sometimes people they might not know somebody might just be in cleveland ohio for work and just randomly like they just need a barber They don't know anybody in Cleveland.
1:00:50So that's like a good tool. That's that power of AI. You talked about launching AI in terms of customer service. When I heard you talk about cash burn, the first thing went out to think AI is efficiency. So how else are you guys looking to incorporate it to become more efficient? Obviously, the revenue goes up, cash burn goes down. Yeah. So I think we launched a product called Cursor internally over the last 12 months. our engineering efficiency. Amongst other things, we got a new CPTO, a new VP of engineering from Stripe, but our output is 94 % more than last year. Because of that? Because of all those that I mentioned, but AI plays a big part in that.
1:01:38So from that standpoint, how many employees do you have? Just a little over 200, like around 200. So do you see AI taking jobs from existing employees that you have to run more efficiently and at a lower cost point so he's tipped us off by his head shake yeah um we see that we think we'll be able to do kind of more with the existing so i don't think that we're like okay we're gonna need to you know cut the x percent but with the 200 we have we think we'll be able to actually like achieve a lot more and then we'll as we grow we'll be able to probably hire fewer than we would have needed to hire like a couple years ago.
1:02:17Yeah, so I think about it like, you know, for 200 engineers, you probably get 300 engineer output with AI, which is meaningful. Okay. So any hair salons? We actually have a few, and they come on quite organically. And we have a handful, and we talk to them and kind of learn about how it's working with them. our focus is barbers, you know, right now, like that, that's the focus, but, you know, there's a lot of hair salons out there. Probably more than, more than barbershop. More than barbershop. Yeah. There's 10 more times, 10s. Yeah, so. And they spend more money. They spend more money. They don't get the haircut as often, but when they do, they spend more.
1:03:02Yeah. Yeah. Yeah, and if you go like extensions, if you go like, you know, color. Yeah. It gets. These braiders, have y 'all seen these braiders that have been popping up? They open 24-7. they're all over I live in Harlem there's like five on every block my sister-in-law was out once finished ahead two in the morning three in the morning it's an incredible business I don't fully understand it but it's amazing it's time consuming yeah but I just saw something they have like a on like a Harvard ah the robot yo I saw that the pressure just starts it they just starts it yeah she cut the time into like out like 20 minutes something crazy I saw the AI bar you saw the AI thing that's not real that's not real you put your head in that's not real that's not real alright that's not real but do you think that that's gonna come as far as having an AI barber I mean or a machine a machine barber precision cut maybe in like 20, 25, 30 years maybe but like the cost doesn't like the investment is just not worth it at this point to do it and it's like so nuanced like you know I think there's better uses of AI, like solving cancer thing.
1:04:14Would that make sense from a return process? I think I know the answer to this, but I'm just going to ask the cost of haircuts. Beneficial for you. They've gone up. They're going up substantially. I saw something the other day. What are your thoughts on it? We come from an average where it was$10 and if you gave me $15, that was a tip. Recently, we've seen numbers inflate, like you said but that helps business no right the higher the price the the commission costs on your side it helps it helps our business it helps the business of the barbers who are able to raise their prices and then keep their their books full so what i think of i think it's great i think it's capitalism it's it's it's the market like for those who over over charge and their prices go higher than their the market of their consumers are willing to bear like they're going to have fewer bookings and they're going to have to calibrate real quick or they're not going to stay in business so every people everybody that you know that complains about the prices I'm like the consumers ultimately have power and people are paying these prices people are paying 50 60 70 100 dollars a cut so that means that's what the market is saying that the price should be if it goes too high maybe it'll come down I don't know but look at Nike's people charge 150 people still paying it you think if they weren't paying Nike would still charge that no they would cut their prices but But I think what I try to communicate when I'm talking to barbers about the prices in general, I said, hey, it's okay to increase your prices.
1:05:48But at the same time, are you increasing the experience? Because the experience should justify the prices. If you haven't, your clients wait 15, 30 minutes for a haircut, and then that's not a good experience. Like, why am I paying this? And a lot of folks, everybody can do a decent haircut. I've gotten a lot of haircuts all the time. And a lot of barbers can get you there. What people don't understand, and the ones that are very successful, is the customer service. It's always on time. You get there at 11 o 'clock, you get in that chair at 11 o 'clock. And I think that is a difference in what people value nowadays, especially if you're charging those high dollar amounts.
1:06:31They just value their time. What, um, how do you like delegate the, who, who's making the decision or what area you guys are focusing on or who, you know, who's where, what needs to be communicated as far as your leadership roles are concerned? Yeah. Um, so it's funny. So early on when we first started, it was just like, everybody's doing whatever, like everybody wears many hats. Um, and, and, and that works. I think as the company gets bigger, more mature, you start bringing on these executives. There starts to be more of a need for like clearly like defined roles and whatnot. So, I mean, where it is now is that, you know, I'm the CEO.
1:07:15Dave is the president. You know, I have like kind of like typical CEO kind of, you know, role that most companies would have in terms of, you know, the C-suite reporting and all that stuff. um dave is like has some really really dope initiatives that i actually think we should talk about uh like the barber school and partnerships um and you want to talk about barber school a little bit yeah yeah so so so barber school is an initiative that you know we're undertaking where you know we want to get uh we want to get the the the barbers doing the right behaviors early on so uh what we launch is a squire for schools which essentially uh we give the software to barber schools for free and uh it gets them indoctrinated in the right way to do business right way to take appointments right professionalism right you know just operational excellence from the beginning so we we partner with like a hundred hundred about a hundred schools right now and and we see that program being like you know how we step into the future a bit we start from law and finance we become successful entrepreneurs how are you guys doing outside of business right because we always talk about balance and imbalance and it's subjective how have y 'all managed to navigate your newfound lives over the past five years as opposed to where we were prior to this journey yeah it's been it's been a journey it's been honestly the best experience that I could have ever wanted, just going through this and going through the struggles and the triumphs and us being together throughout the whole process as co-founders.
1:08:58And during this, we both had children. I've had two kids. Dave has a child. I've gotten married. So our personal lives have also, there's been so much change over the last 10 years. And, you know, at some point we were very broke in those early days and you make a lot of sacrifices. And then when you start to do better, you know, the situation changes and quality of life and lifestyle changes. So I think we've really managed just really no work life balance when you're a founder. Like it's just all life. It's all part of the same thing. Like you're never really turning off and it goes with you everywhere.
1:09:41and I think you know for me I think it's you know it's important to have other outlets and to really be focused on like you know wellness working out like trying to keep your energy level high because it's a marathon this shit is hard like it will I've seen a lot of founders like crash out burn out and like you know they've had to close their companies down and mentally they just haven't been there so but I think we're doing you know doing well now stress you know but I think outlets like my outlet is like music You know, I love music. And, you know, also, you know, we have a lounge in Harlem, a lounge in Hell's Kitchen.
1:10:22Saint, talk about that. I mean, it's creative. You know, I think the great thing about Saint is, like, it's a place where the community could, like, gather. I think there was a void in the market for that, avoid that, you know, folks of color ages like 25 to 45 would come in Manhattan to feel welcome. You know, we have a great operator, James Jones, who, you know, is a friend of mine for 20 years. And he's been doing this. So, yeah, I mean, yeah, it just was an opportunity. And so you guys have mentioned, like, as far as exit, right? So you're planning for the exit, right? Is that safe to say?
1:11:05Yeah, I mean, you're always planning. So in building the company and trying to get it as big as possible, that, in a sense, is planning for the exit because you know that's going to help the ultimate exit. But we're not actively in a process. But even that, because it's like even how a company is built, you have to keep in mind to build a company to exit, right? And that's something that people might not be fully aware of also. So talk about that as far as having that end in mind. Even when building the company and having it structured so it's like eventually gets to that point, you don't have to rework things and try to figure it out on the fly.
1:11:46Yeah, if you're raising money from professional investors, they're investing with the expectation there's going to be a liquidity event, an exit event at some time. If you have a small business and it's like a lifestyle business and you haven't taken on money from professional investors, that's different. You could just run that forever. And that's just your lifestyle. It just kicks off cash. It provides income for you. And that's cool. But that's a different kind of business. what we have is a venture-backed you know business of scale so the expectation is there will be some type of event and that could be an IPO or that could be getting acquired that's really only two two ways um and uh so those are you know just like any other company like us like those would be the two options to get liquidity yeah there's there's not many i'm glad we spoke about why i commented we had did an episode a couple years ago to speak about it but there's like a young group of guys or girls that are trying to get to Y Combinator, have their startup be, have more eyeballs on it?
1:12:53What are the type of qualities that a founder should have prior to going there? I mean, I think the traits are like, I think the number one trait is resilience because it's not going to be easy. Like, you don't have to be the smartest. you just have to be the folk that won't like it's a war attrition that won't give up i think that's the really these folks these folks that i see and i'm like that person is going to make it because of the finacity and the the the say hey i'm i'm making somehow and also what's really telling if you give somebody advice right on how to do something and they they need to do it themselves to find out early on.
1:13:42Like later on, like, Hey, you live, you, you have experts or you, you have experiences, but early on, like the best ostrichos I met, even if you gave them the advice, they have to see it through themselves to understand it from their perspective. And you learn a lesson, but I think the number one quality is the determination and kind of grit. When you saw Sam, you saw that? Sam Altman? Oh, yeah. Oh, yeah. Yeah. For sure. We didn't know what was going to be at the level just now. Yeah. But Sam is a cool dude. Like, he gets a lot of, you know, flack sometimes. But, you know, he's the same person that he was nine, ten years ago.
1:14:25Very important guy. He was, he was, he had a sense of things. Like, he was thinking about universal basic income, UBI, ten years ago. And AI. And AI, yeah. Yeah. Yeah. So what's next for you guys and where can the people find you? Talk about what's next as far as initiatives and then website, social media, and all that stuff. Yeah, I mean, what's next? Just doubling down on this AI and really trying to incorporate it more in the business as well as continue to add value for our customers. Yeah, you can go to kidsquired.ai. It's got the latest on that, yeah. And the AI, like you said, is calling.
1:15:06Is it more than that or is that the main focus? Oh, it's more. Yeah. That's just one. So what's the other feature? So essentially we're embedding like this AI layer throughout the entire like backend platform. So it's really going to be touch everything. And it's designed to make the barbers' lives more efficient, help them make more money. The other way that we already have incorporated is through our marketing feature, which is called Engage, which allows the barbers and the barbershop owners to like message, send messages to their client base, like email, text, push notification. So we've supercharged that with AI now.
1:15:44So now they can just type in what they want to achieve. Like I want to get my customers to come in for a holiday cut and it'll literally create the campaign and then tell them who to send it to and then send it out. So it's like their personal, like business partner that just like executes on things for them. So we're in the early, early phases. those are the first two things but we have so much more coming well appreciate you guys man thank you for your time and yeah man look forward to it for sure appreciate y 'all man thank y 'all for being disruptive alright y 'all thank you for rocking us we'll see you next week peace Ernest what's up you ever walk into a small business and everything just works like the checkout is fast the receipts are digital tipping is a breeze and you out the door before the line even builds.
1:16:34Odds are they're using Square. We love supporting businesses that run on Square because it just feels seamless, whether it's a local coffee shop, a vendor at a pop-up market, or even one of our merch partners. Square makes it easy for them to take payments, manage inventory, and run their business with confidence, all from one simple system. One of the things we love most is seeing neighborhood businesses level up. There's this West Indian spot right in our community that started with a small takeout counter. Now with Square, they've been able to expand into a full sit-down restaurant and even started catering events across the city.
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1:17:45Visit square.com backslash go backslash E-Y-L to learn more. That's square.com backslash go backslash EYL. Don't wait. Don't hesitate. Let Square handle the back end so you can keep pushing your vision forward. Hello. Hello, all my people. What's up? It's Questlove. Recently, I had the opportunity to sit down with the one and only ASAP Rocky. He reflects on his journey from Harlem roots to global icon status and discovering the hip-hop origin of his name. The ledge was on the TV. Rakim had the Buckethead Kangol join on. I'm possibly like, that's Rakim. That's who you named after. I just was like, damn, that f***ed I swag.
1:18:27Listen to The Questlove Show on the iHeartRadio app, Apple Podcasts, or wherever you get your podcast. This season on Dear Chelsea with me, Chelsea Handler, we've got some incredible guests like Kumail Nanjiani. Let's start with your cat. How How is she? She is not with us anymore. Okay, great, great, great way to start. Maybe you will cry. Ross Matthews. You know what kids always say to me? Are you a boy or a girl? Oh my God. All the time. That's so funny. I know. So I try to butch it up for kids so they're not confused. Yeah, but you're butching it up. It's basically like Doris Day. No, I turn into Bea Arthur.
1:19:03Listen to these episodes of Dear Chelsea on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. What if mind control is real? If you could control the behavior of anybody around you, what kind of life would you have? Can you hypnotically persuade someone to buy a car? When you look at your car, you're going to become overwhelmed with such good feelings. Can you hypnotize someone into sleeping with you? I gave her some suggestions to be sexually aroused. Can you get someone to join your cult? NLP was used on me to access my subconscious. Mind Games, a new podcast exploring NLP, a.k.a.
1:19:39neurolinguistic programming. Is it a self-help miracle, a shady hypnosis scam, or both? Listen to Mind Games on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. A new year doesn't ask us to become someone new. It invites us back home to ourselves. I'm Mike Della Rocha, host of Sacred Lessons, a space for men to pause, reflect, and heal. This year, we're talking honestly about mental health, relationships, and the patterns we're ready to release. If you're looking for clarity, connection, and healthier ways to show up in your life, Sacred Lessons is here for you. Listen to Sacred Lessons with Mike Delaroach on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
1:20:21Hey, it's Joel. And Matt. From HowToMoney. If your New Year's resolution is to finally get your finances in shape, we've got your back. Prices, they're still high, and the economy is all over the place. But 2026 is the year for you to get intentional and make real progress. That's right. Each week we break down what's happening with your money, the most important issues to focus on, and the small moves that make a big difference. Kick off the year with confidence. Listen to How to Money on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. This is an iHeart Podcast. Guaranteed human.
From the publisher
This week on Earn Your Leisure, we sit down with Songe LaRon and Dave Salvant, the co-founders of Squire, to break down how they built a barbershop tech platform into a $750 million company. They share how they met, landed their first customers, and built their first product without deep technical skills — including why they gave Squire away for three years before ever charging. The conversation dives into the realities of fundraising, from relying on angel investors to survive, taking 60 meetings to secure one VC, and how an $8 million Series A helped unlock massive growth. Songe and Dave also explain the role Y Combinator played, the strings attached to outside capital, ownership dilution, and what investors truly expect when they invest. We also explore how Squire scaled to 32,000 barbers and 10 million customers, what their $750M valuation actually means, and the challenges of being two Black founders raising capital. Plus, we discuss Squire’s marketing strategy, deploying $100 million in one year, and whether AI or rising haircut costs could disrupt the barber industry. EYL University: https://eyluniversity.com #EarnYourLeisure #Squire #SongeLaRon #DaveSalvant #StartupJourney #Fundraising #VentureCapital #BlackFounders #Entrepreneurship #TechStartups
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