#071: How Patrick Cleary Left a $1B Unicorn to Build Paul Street into a Top Growth Agency

Yeah, walk us through that decision-making process of like, okay, you had this interest from when you were younger of like, I want to start or co-found a company, but I'm also on the founding team here. And as you mentioned, one of the fastest growing companies or fastest growing company ever out of Ireland to reach unicorn status.

Yeah, exactly. Let's see, give context on timelines. We started Pole Street end of '22 and kind of really started kicking off in '23. I met Aaron, Aaron's my co-founder. Aaron's from the affiliate background for the previous 6 or 7 years. So, we met, we have a bunch of mutual friends, we started hanging out a bit more. And it was actually on a drive down to, what is it? I can't remember the name of the conference. We were driving down to a conference in Philly from here. So, it was just me and him for like whatever, an hour and a half, 2 hours. And he starts telling me about wanting to start his new agency, because the agency he was at turned into like a platform and they stopped. Um, and all these other clients wanted to work with him, but agency wasn't there. He's like, oh. I was like, that, that sounds awesome, you should do that. And he's like, yeah, I know, I really want to do it. Uh, I was like, great, yeah, like, do it, I support you, go for it. He's like, I need to find a co-founder and all this. And I was like, I'll try help, or we'll try I do something again. This is 20, that must have been what, summer of '22. Anyway, we kept talking and then he kept asking like, oh, is there any way we could like try work together? I was like, I'd love to, but I'm just not stepping away at the moment. Then eventually it ended up being like, okay, well, how about I just try to do things on the side or I'll do things in the evening and simple, like help set up the company and talk through things all the time. And it just started growing quickly and I was like, oh shit, this is, more interesting than continuing my day-to-day role.

Welcome back to Season 3, Episode 14 of the Turning Pro Podcast. Today we have Paddy Cleary, who is a founding member of Wayflyer and also co-founder and president of Paul Street. Thanks for joining us today.

Thanks for having me on.

Damn, I nailed that. Oh, usually takes me— usually takes me a couple of tries.

Clean intro. Great pronunciation.

It's impressive. Didn't mess up the name.

What's that?

Didn't mess up.

Yeah, I was like thinking when I started, I'm like, oh, I'm bound to mess up. But no, here we are. Um, would love to just jump in, maybe start with the, the story of Wayflyer. I feel like we got to start there.

Um, well, yeah, what, what do you want to start?

Remember like where, where you guys started, where the business got to before you ended up leaving and going off and doing a new thing?

Yeah, I mean, uh, crazy. So I guess we can start my background. I mean, I was been in New York 2016, um, was working on finance. My background is engineering. Then I'm good friends with one of the founders, Jack Pierce, um, and he was coming over raising money for the idea of Wayflare. Um, I would always have people staying on my couch, uh, in Williamsburg at the time. So he came over, was staying on the couch, like, oh, I got this idea for a debt fund, and wouldn't— didn't really go into much detail because I didn't think I'd be very interested. But at the time I was finishing up, just got my green card, so I was able to look at doing my own thing. I always wanted to have my own company. So I was looking at playing around different things in e-commerce. I think I was, me and a few buddies were getting like boxers, we wanted to start like a Mack Weldon competitor or something. And then Jack's like, oh yeah, I know I have this debt fund idea. I was like, oh well, tell me more. Like I was Again, I was in a fund of funds at the time. And he's like, oh, well, it's like an e-commerce thing. And I was like, oh, OK. Come on, give me some information here. And he goes, oh, well, I met this guy. He was working in VC at the time for Highway One. But he's working at VC, and he came across the co-founder, current CEO, Aidan, who's working at— or he had founded Conjura, which is a data analytics platform. He was like, oh, I met this incredible company and like team that had this really accurate forecasting, revenue forecasting for online businesses, but they're using it for the wrong thing. So he starts to explain that to me and I'm like, oh, that is very interesting. Um, he's like, yeah, so we're gonna just take that pivot, use that for revenue forecasting. So we connect up into all transactional data, marketing data to see what the next 6 months of revenue looks like or what their marketing efficiency looks like so that they can lend money over that period and have a really accurate understanding of what that future revenue looked like. And I was like, oh, that makes a lot of sense. That's exactly what I'm looking at. My background in data analytics and then being interested in e-commerce and working in finance, I was like, this ticks a lot of boxes here. Which is complete luck or fortune, I guess, that this guy is starting the company, staying on my couch. So that whole week we spent a lot of time talking about it. This is probably 20— say this is like August, September, October 2019. Um, and then yeah, so we kept, kept talking. Uh, I became a seed investor then as he was raising money.

You invested first before coming on board?

Yeah, with friends and family.

Ah, interesting.

Wow, I love that.

Um, and that was my— I'd made some other like angel investments at that point, but I had high conviction in that and put way more money than anyone should in an angel investment that is a friend of yours that is very much a long shot. As I think you guys know, angel investing is similar to roulette.

Very similar.

But there was a few things. One, I really liked the data analytics part of it and the e-commerce space, and there was a clear need for working capital. If you had— if you're an e-com brand and you had like proven product market fit or proven you had marketing efficiency and there was like need for your product, the main thing that's holding you back is access to cash to put into marketing and inventory. So that was clear. And then the other, uh, thing that made it very easy was ClearBank was around at the time. Didn't have, or at least didn't talk about, any sort of data analytics aspect, but had identified the need for working capital in the market. So they were first to market, and they had, um, they already had, I think, a billion-dollar valuation at the time and were just giving financing at extremely high rates without really understanding, uh, having a really good underwriting model. So that was the biggest question mark at the time, was like, oh, how would we compete with a company that's already valued at a billion dollars? We were just some guys in a basement in Dublin at the time. But then when we went to market, we realized that there were such high defaults because they didn't have the analytics piece, that they were pricing so highly. So it didn't actually matter how expensive the debt capital, or the capital we were getting to lend out, was, because we had a very clear understanding of— if it was a good company to— or how we underwrite. We were very confident in how we underwrote the brands at the time. And still to this day, default rates have been— I don't think there's been any year that defaults are less than 1%. For context, they gave out over $1 billion last year and are growing still.

That's crazy.

That's a wild metric. That's so rare.

Under 1%.

Oh yeah. Again, I'm not in the weeds anymore.

Yeah, yeah.

I don't have access to that stuff.

I imagine, I imagine over the last 12 months things have gotten a little bit more interesting.

No, you'd be surprised because also the majority of brands that Wayflyer finance are all fully unsecured. So what that means is, one, it's more founder-friendly, but two, it means that they've always only focused on like the top, top brands. And so a lot of brands just don't meet the criteria, won't pass through.

Yeah.

And so it's like they're very selective of who they work with. And again, it's quite accurate to like 6, 9 months out, you can kind of make those decisions and be able to see if, okay, the market's not looking so great, as it hasn't for the last 18 months, 2 years. Um, so yeah, they've done to my knowledge, there's not, not big, uh, defaults or anything to be—

What was the moment in your Wayflyer journey where you're like, all right, now's the time to, to jump?

I mean, that was a really tricky decision for me. Um, again, I always wanted to have my own company, uh, so that's since I was young. Um, so I was always in the back of my mind. How— then I have a co-founder, obviously, up Paul Street, Aaron. So I was running partnerships here in the US for Wayflyer. So my main role ended up kind of being the face of Wayflyer in many ways. I'd just kind of go to events. I'd host dinners. Then obviously build partnerships.

You did a good job, because I think that's where we first met or where I started to hear about you. I just knew your name.

I actually— we went for coffee, what, a few weeks ago, maybe like 2 months ago?

Yeah, yeah. But I've known your name for years.

No, I know. Yeah, yeah, yeah. But I was trying to think. I was like, wait a second. Like, we definitely chat a long time. So I went through my old emails. It was, uh, July '21.

No way.

Yeah.

Wow.

It was— what was it, the Bulletproof, or— oh, the Proof.

It was like a wellness—

that was your email? Yeah.

Wow, that's a long time ago, man. Yeah, there you go. So once you— yeah, walk us through that decision-making process of like, okay, you had this interest from, you know, when you were younger of like, I want to start or co-found a company. But I'm also on the founding team here. And as you mentioned, one of the fastest-growing companies or fastest-growing company ever out of Ireland to reach unicorn status. That's a pretty tempting place to stay.

Yeah, yeah, exactly. But then obviously, if you look at the market in the last 2 years, the VC market has dried up. Their last round was their Series B. And that's, again, the company internally has continued to succeed and grow, but it's dependent on interest rates, on when VC opens back up. So that was certainly top of my mind. Let's see, give context on timelines. We started Paul Street end of '22 and kind of really started kicking off in '23. I met Aaron, Aaron's my co-founder. Aaron's from the affiliate background for previous 6 or 7 years, had worked with a ton of like the huge brands who had succeeded in affiliate and worked on those accounts at another agency. So we met, we have a bunch of mutual friends, we started hanging out a bit more, and it was actually on a drive down to— oh, what is it? I can't remember the name of the conference. We're driving down to a conference in Philly from here. So just me and him for like whatever, an hour and a half, 2 hours. And he starts telling me about wanting to start his new agency because the agency he was at turned into like a platform and they stopped. And again, he'd worked with HelloFresh, he'd worked on Goalie, he'd worked with Onnit, who were all these huge success stories in specifically in affiliate. Like a lot of them have between like 50, 60, 70, 80% of new customers were acquired through affiliate. And all these other clients wanted to work with him, but agency wasn't there. He's like, ah. I was like, that sounds awesome, you should do that. And he's like, yeah, I know, I really want to do it. Uh, I was like, great, yeah, like, do it, I support you, go for it. He's like, I need to find a co-founder and all this. And I was like, I'll try help, or we'll try to do something. Again, this is 20— that must have been, what, summer of '22? Um, But yeah, we kept talking. Um, I was like very busy at the time. I was— no interest in trying to leave Wayflyer, certainly. Um, anyway, we kept talking, and then he kept asking like, oh, is there any way we could like try work together? I was like, I'd love to, but I'm just not stepping away at the moment. Then eventually it ended up being, okay, well, how about I just try to do things on the side, or I'll do things in the evening and simple help set up the company and talk through things all the time. So the end of that year, mostly started '23 as working both jobs, had tried to just do the simple setup. I was like, oh, we'll see what happens. I think we started with a couple of clients, Solowave, who was like Andrew and Eli are more friends than anything. And then Aaron had also separately known them, so they come on at the start, then a bunch more of Aaron's, like people in his network who he'd worked on. So we had like maybe call it 4 or 5 clients right away. And I was like, oh shit, okay, there's a bit here. And again, I was really just looking after, call it setting up the company, making sure we were fully compliant and receiving or sending out invoices and receiving our bank account. So it wasn't a lot of time required. But then it just started growing quickly, and I was like, oh shit, this is more interesting than continuing my day-to-day role at Waveflyer. So that was really tough, because again, a lot of my closest friends obviously work with or work at Waveflyer, and I'd done a huge amount there. But eventually it just grew. Positive just grew quick to the size where I was like, OK, I need to make that. Transition over. So it was kind of— it was almost a cop-out. I didn't make a big leap in the end. I was kind of stuck between the decision, and then the decision was made for me.

I feel like that's a very common path though to starting a company. Like, I would never recommend to someone who wants to be a first-time entrepreneur, go quit your job and just like lock yourself in a room and think of an idea. Yeah, well, it's always like a side hustle until it's not. Like, that was the same thing with Platter. I was working at GoPuff at the time, was tinkering on some shit on the side, and then it started to grow, and then I was like, wait, this is real. And then it started to take away from my day job. And then I was like, if I don't give this more attention, I don't know if it'll ever see the, you know, the light of day beyond that. And it's like, you just— the rubber meets the road and you got to pull the Band-Aid off.

Yeah, it's classic golden handcuffs. I was in a great— yeah, I loved my role and I had a lot of freedom there as well, and, and great access. The thing I was most interested in actually, which is a good point to bring up, like even when we were starting it and what, call it what, start 2020, because it didn't actually launch till April 2020, I think. Um, I joined, I think, maybe January 2020. And then what I was most interested in was like, oh well, at the very least it's going to be a cool like data analytics platform and I'll be able to like see what other e-com businesses are doing. Again, I was like messing around with starting my own e-com brand at the time, so I was like, I'll learn some stuff. But then COVID happened right when we launched, and then every brand needed financing or needed working capital because everyone was shopping online, so everyone was growing. And so all of a sudden we had hundreds, and then we had thousands, yeah, of brands connected to these platforms. And, and what was most interesting to me was it meant that one, I'd get to see what brands were doing cool things or what, like, were growing in certain ways, and I'd be able to connect right with the founder and be like, hey, oh, you're in New York, great, let's go for dinner or grab a drink. And I get to chat to these people all the time or be on calls. I must have been— I must have talked to honestly hundreds, if not like 1,000 different e-com founders over that like 2020 to 2023, end of '23 period.

I'm curious, in a very public-facing role, it could be BD part— was your head of partnerships or—

Towards that.

Yeah. BD, partnership sales, whatever it is, especially public-facing. And in a city where you can't just do Zooms, you got to be in person, dinners, coffee, whatever.

Well, 2020, 2021 was a lot of stacks. Yeah. Yeah.

In those roles, I think we have similar roles as well. Some days when I'm well slept and working out, I have a ton of energy. I'm excited about the calls and they're going well. It's easy to do like 10 back-to-backs. But in the days when you wake up and you're like exhausted, you have 4 hours of sleep, you're like eating like shit, you're not working out for whatever reason— what are those days like and how do you get through them?

Like back then? Yeah, back then. Yeah, I mean, back— that was probably the— I wasn't exercising a huge amount during those early years, um, but there was just the fact how fast the company was growing and seeing all the each month, just more and more brands signing up and taking money as well, was— that was just the energizing in itself. And like, yeah, easily take 10 calls back to back, it's fine.

What would you say was the biggest learning that you took with you from Wayflyer when you were starting your own company?

Um, I don't know if this is much of a learning from Wayflyer, but just even over the years, just how important network is. And, and keeping those relationships strong with those, with those people within your network, especially in e-commerce. E-commerce is such a small, tiny little space.

You're in it for like 3 months, you kind of like know the amount of overlap is crazy.

Um, so I guess that was a really big learning, just like how important it is to keep— but be a nice guy, I guess. That's pretty important.

Don't be a shitty person.

But like how connected everyone is and to always just be proactively thinking about your network and keeping that strong.

More tactically, what are ways that you think about maintaining your network?

I'm probably actually not the best at maintaining my network. I try to just go to as many different events I can and keep up with people, but I definitely need to get better at that. I have built a great network over the years just from sheer volume, and again, not pissing anyone off, at least I don't think I have. But like, yeah, I don't know, I'm like a professional-grade networker, but showing up, going to things. I think you guys talk about a lot is like not just being focused on like, oh, go for a coffee during the day or trying to get meetings. It's like, no, it's like, what do you do outside of work hours? Like hanging out with someone on a weekend. Um, yeah, so I guess truly making them more into your like friend circle and caring about those people, being curious and interested in what people are doing, I think is the precursor. And then that evolves into being friends with, with people and like hanging out with them more. Like I've gone on One thing we've done like each year is like going to Austin for, for the F1. Aaron lives in Austin, so that's an easy one. But, um, we'll get like a bunch of people come with us, and that's always a great time. And you, again, you're building network with their friends.

Yeah, I think that's actually— it's been a huge learning for me as well when you realize there are so many people in the world of whatever industry you're in. Like e-com, there's thousands of brands. You can build a successful business and do it by being around people that you enjoy being around. And there's longevity around, to your point, like building relationships to the point where they feel like friendships. When you start to go into business with someone, or like a mutual customer that we've talked about is NarrowGum, right? Like Ryan and Kent are awesome. I consider— yeah, look, he's got it with him. My gum is sitting over there on the desk. You could see it. Yeah, but that's someone who, like, I feel like I'm their genuine friend. Like, yeah, we're a partner of theirs and we're doing business together. But when I look at the scale of all the people we work with, like, if they were in town, I would go hang out with them and not even talk about business for 2 seconds. So being able to scale that concept is challenging, but I think it makes it more rewarding for me.

I think there's like two layers. I think you can be very intentional, tactical, whatever you want to call it, about increasing your surface area of like new people that you can meet. That's the strategic, like events, conferences, also just showing up and like being a curious person, reaching out to people like we met on LinkedIn just because like we were both trying to reach out to cool people and we want to learn what they do. So I think that part you can be very strategic about. But then the other layer after that, in terms of like catching up with people or like nurturing relationships, that I have like no strategy for. It's just of all the people that you meet, you're just going to get along with some of them and those will just naturally— like if like, oh, you're in Greenpoint. Okay, cool. Let's hang out. Oh, you're in the city. I'll be around. Let's do a potluck. Those you don't— I don't really think about those. It's just like, oh, I had a good interaction. I want to keep hanging out with them. It's like, I don't think there's that much strategy to like nurturing relationships. I think it's just people that you vibe with, you end up hanging out with more.

Yeah, it depends where you want to spend your energy.

100%. I want to talk about fast scaling agencies. And so you guys are a year and a half in?

Uh, yep, year and a half, coming up on 2 years.

Yeah. Okay. Um, there's an art and a science to like a fast growing agency from a reputation standpoint, from a BD standpoint, retention standpoint. And so walk me through, what are a couple things that you think you guys have done very well?

We're certainly more on the art side of things.

I love the honesty.

Yeah, I mean, it's easy to look at that and say, oh my god, of that year and a half or 2 years, you've grown so quickly. Like, how did you do that? Or what did you do in those 2 years? But again, it's more important to look at what happened before that 2 years. And again, I've built a great network, so I just know a ton of founders. And even more so, Aaron built a great network in the affiliate space and is known for affiliates. Everyone wants to work with Aaron, and he has an incredible network. So the two of us, and we're very aligned on, I guess, business development. We have zero business development team or function at the company. It's just all come through me and Aaron's network to start, and then after that, it's like more referrals and introductions through our clients. Like, one thing we always say is like, good work brings more work. And also, if you look at like the retention that we have on a lot of our clients, I think we have like 5 or 6 brands that have been with us for almost the whole time, like since we started.

So crazy.

Um, for that, like at least 18 months. Um, and some clients literally since the first month, like Solo Wave, I think I mentioned. Um, So just by focusing purely on the work that's being done to the clients and making sure we're listening to them, aligning to what their goals are. And that's where things get tricky as well. And we have a big operations team for that because it causes more nuance per client, which takes more work. But making sure their clients are listened to and we're— changing our strategy to what they're trying to achieve, um, has always been really important to us. And then, yeah, and then just reaching out to them and trying to hold on to the clients. Because one metric I try to look at a lot is like net client retention month over month. So sure, yeah, it'd be great to do a bunch of marketing and sales and sign 5, 10 clients in a month, but if you're losing clients, what's the point? Um, So it's much like, I'd much prefer to have— oh, I'd love to have 1 or 2 more total clients, which a huge part of that is obviously retain retention. Um, so a lot's coming from our network and then just being really focused on driving good work and constantly improving on that work. Um, and making sure that— and again, the amount of— it's hard even to— that's why it's much more art than science because it's so hard to quantify like the referrals that we get from different clients, or like how important it is to have like a Hexclad, like marquee kind of client from early on. And then our team there, and like the work we do with like the numbers they do is amazing just through the affiliate channel as well. Um, and how highly they speak of us and then like refer clients in, like that is unquantifiable how much maybe new business that comes into us. I think another big learning as well is being— and it's a, this is a blessing to be able to do it, but being selective of who you work with as well, client on the client side. Again, that feeds in massively to the retention piece. And if you believe you're gonna be able to do good work with that client, and we try to focus on much larger clients that have like found that product-market fit, which is really important in the affiliate space. And on all types of our, on each of our service offerings, because it's much easier to get traction or to tap into our network of publishers to talk more about these specific brands, or even get media buying affiliates interested because they see the volumes that go through them and they have an idea of what kind of money they'll be able to make and try drive our money through that channel. I'm not sure if I answered your question.

I think you did. Something that I guess— selfish question right now. I think about— we started like 2 and a half years ago, and for— I swear, like the first year and a half, 2 years, I thought every single team that I worked with cared about me being in the room and me being on the calls. I'm sure there's ego wrapped up in that. And then I forget who told me, maybe it was on a podcast or something, that end of the day, your customers care about your standards, not your presence. They could care less about your presence as long as the standards are getting higher and higher. And that completely reshaped how we built our executive team, how we built our operations team. And it seems like when we've caught up, that came to you guys naturally, and you immediately knew to do that. Was that natural? Did that take some learning of, like, they don't care if Paddy and Aaron are on the call as long as it's top-tier work?

Yeah. Well, nobody cares if I'm on the call, I don't think. But more so for Aron from the start, I think, and that was something we had to address that. And obviously we're starting out, there's just the two of us, and then team grows out and whatever, and then it starts to become a question of, okay, we can't be on every call, or Aron can't be on every strategy call for client-facing roles. And we have a lot of, two of our closest friends, I say we, me and Aron, are also agency owners, agency space, and have similar kind of following or would have a name that would want to be on that call. And that was a lesson that they maybe passed on to us early on as well, is you need to set those kind of boundaries and expectations. It all comes back to expectation setting from the start, or we found that certainly. We also hired great heads of each division under us early, so we focused on hiring those people in early on that we knew we could trust. And then they would get introduced on. So I'd still, even like most new prospects, me and Aaron will still, and again, Aaron's the one that they want to see, but Aaron will jump on. And then we have a very robust onboarding process and strategy and onboarding calls, which our team will be running through those decks and presentations and going into detail and making it clear how we communicate with clients and obviously and taking on what their communication preferences are. But, um, yeah, it's just setting those clear expectations from the start. And we, uh, I'd say we learned it, but we're also kind of taught that from our network of other people who've gone through it, um, which was a huge help because there's no way you'd be— you can scale if you have to be on and in the weeds of every impossible—

do you have any situations where a client just like didn't didn't receive that well?

Um, less so now, definitely more so last year, probably in that kind of transition page. Um, and it would have to be like something would have to be going wrong for then that to be like an issue, because when things are going well, who cares?

I don't care.

Yeah, we don't want to see Aaron anymore. Um, but yeah, there certainly was, uh, last year if like, I don't know, if performance wasn't meeting the expectations, and all of a sudden Aaron was on the earlier calls and wasn't then, then it's like, oh well, it's because he's on the calls. And when that probably wasn't even the case, but it's easy to draw that line. Um, but no, I don't think that hasn't come up in a while.

You've been in and around this e-com space for a long time. I'm curious to get your perspective, having worked with the amount of brands you've worked with. Like, what do you think are the differentiators for those that build like strong, successful brands versus a lot of these flash-in-the-pans that come up and disappear, especially with the fight— like, the financial environment that we're dealing with today.

Well, I was going to say, like, having an understanding on your, uh, financials and like when you become profitable or how you become profitable or trying to be first order profitable or whatever it is, if it's an LTV play, um, like Focusing on, like, you need to have that bare minimum of trying to focus on your financials. Um, it was crazy. And like, this question can be answered in a different way every year over the past 4 years. Um, you'd be a crazy person to be focusing on profitability in 2020.

We were talking about that earlier today. Like, I, I feel like I looked like an idiot for building a business now 2 and a half years in where we were generating revenue in the first year of business as a SaaS company.

Yeah, but—

It was frowned upon almost.

Yeah, but that turns out to play, to work in your favor over the long term. Growing any business is a question of profitability or growth, and that they're levers you pull on. So a lot of the big brands that are still around and successful today, they understood those levers, and they didn't pull too hard on the growth. Or at least they knew when they were pulling hard on the growth and were able to adapt quick enough to the change in the markets that we saw. And other ones are like, there's some people that are just incredible marketers, or— and I don't mean like, oh, they're great at Facebook ads. Like, they'll find ways to make viral moments or, um, just be incredible at short-form video. And be able to acquire customers at so much less and not having to focus on Facebook ads or just creating a static ad and putting money behind it. That's seen huge success. Have you guys ever heard of a brand called Telfar? Have you seen those bags walking around? You'll see them all around New York. No. It's more of a— it's a handbag, so I'm not too surprised. But just a quick, quick story. They were one of the craziest brands I'd seen coming in. And this was, this actually is summer of 2020. And they came in, again, so summer 2020, we've only been live, Wayflyer's only been live for, what, call it 3 or 4 months. And the whole premise was you connect up your marketing platform and your transactional data, and we understand your potential growth from that. We meet this guy, the COO there. He's, uh, New Jersey-based. He's here in New York. Uh, the two founders are these fashion designers, and they'd won a— they'd won like some award for the design of this handbag that grew the viral sensation and still, still is. Um, but they had this like Instagram page that was viral. Don't— hadn't avert— like hated the idea of paid ads to the point we were trying to I was so— and again, this is the scrappy— we're only a few months old, so I'm just like meeting this guy. I'm like, okay, we need to try find a way to give you money, but like, you do have anything we can connect to? He's like, no, no, I— we don't ever want to do paid ads.

It was all organic coming in, all organic. Insane.

And just from creating these— again, the Instagram page was just viral, and they would do like their own like fashion shows and Again, they're just incredibly popular online, and they also had to have a drop model, so they'd only launch, they'd only make available like each week one color of the bag, and they'd have like whatever, 15 different colors, and it would only be live. They'd sell out in seconds at that time in 2020, it's out in seconds. And we're like, okay, well, they clearly have demand. They've somehow created this virality around the brand, and they've no interest in doing paid brands. Now, that's not something that you can replicate. It's almost impossible to replicate. These are like established fashion designers who won an award on this bag and then created virality. Um, but I mean, when you find those kind of products that aren't reliant on just like trying to game the marketing system, like online marketing they're the ones that really take off. I don't know what formula there is to make a successful brand, but that was one of the most— that was one of the craziest brands I've seen.

But I always wonder, because I, I know a couple of brands like that. I mean, a friend of mine right now, do you know Seagull and Stable?

Yeah, the hats.

Yeah, I mean, that's a great example where it's like every time he was—

he did a great— he was incredible.

Yeah, it's just like it would go crazy But I always wonder, just like, what is the long— like, what is the longevity to that? And what happens if you have a month where you don't have this viral moment? It doesn't mean your brand is struggling. It just means like you need to reinvent yourself to optimize for longevity because you never know when your brand stops going viral.

Yeah, well, to— if you want to go on the Siegelman Stable like case study, I think they did really well. And I think there's the best way to launch brands still today is you have to, you have to find your audience and you have to kind of understand who you're selling to. And I know what they, they like sent a bunch of hats and gear to basketball players during COVID I think it was rappers and athletes. Yeah, yeah. And then, and then just started collecting emails and sending out, uh, again, so we're talking they did, they found an interesting way to go to market without just throwing money into the online ad machines. Um, and then they grew slowly from there. So it's even going back to like growth lever. And I'm sure they were probably profitable in those early days because they weren't spending a bunch on just like making people see ads. And that's especially when you're starting out, you don't know who to put those ads in front of because you don't know who your audience is. Um, so like finding those ways to— another like creative way to do it is doing some really targeted influencer outreach, or like JOLLY, their launch of sending emails around and getting all these influencers to post and get people to just talk about how dirty your water is and the effects of dirty water on you, and just like, oh, enter your zip code to get a free water report of how dirty your water is. And then that just blew up, and everyone was like, okay, I can do that, I have my zip code. What's the next thing you have to enter? Your email address. OK, guess what? You got hundreds of thousands of email addresses now. And you haven't paid a cent on ads. But then you launch. And that was pre-launch. Then they launch with all these email addresses that they've collected of people who have just received a water report saying how dirty their water is and how bad it is for your hair and skin. OK, you should probably buy a filtered water shower.

Outside of just the marketing side of things or the creative side of things, Are there any operators or operating teams behind brands that you've been really, really impressed by? Maybe like a big brand, but like under-the-radar teams, whether in supply chain or operations or finance, that you're like, those guys are killers.

And like, Ben and the guys at True Classics have just done an incredible job. And they're also like, they've spoken about it and they like really understood the way to use like the likes of a Wayflyer. Because a lot of people will talk about like short-term— they'll be like, oh, that's like short-term financing, that's expensive. Um, but they were like almost the perfect fit of, oh, you have created this demand, your capacity to how quickly you can grow is how much access to capital you have. Some brands will go and raise a ton of equity and do all these things. They just were like, you can tap in with the likes of like a Wayflyer, you can— and you're constantly connected. So if you can see that the demand is there, they'll just be able to give you more money. And they just did that for 2 years of— sorry, I'm sure they still are. Again, I'm not in the weeds, but just watching them over those years was incredibly impressive.

They're like very sophisticated operators.

It would certainly— Ben on understanding how to grow on Facebook, incredibly sophisticated. I think it's Matt, or I can't remember who was like running their finance, but the three of, um, Brian, Matt, and, uh, Ben, like, together, understanding how quick— how to be able to just like pull that growth lever as much as possible while still like not, not going too far over the skis. Like, that— the growth trajectory they went on was—

yeah, but I imagine their first sort of profitable, probably nowadays, I think.

Yeah, I'm talking through the years.

Yeah. So then at that point, it's just like, how much money could you literally get and how fast could you grow?

Yeah, the way to think about like taking any sort of financing of any kind is like, okay, well, what's the benefit you're getting? Does the benefit outweigh the cost of this financing round? And like, their benefit was just like growing at a ridiculous rate, um, and it was way better to do that than take on any equity or whatever fees were involved. Um, other ones like, like Ryan from JOLI as well, he's an incredible operator from, uh, like already successful. He has a shoe brand that he's great. Yes, bought by Steve Madden.

Yeah, yeah.

Um, who's the founder of—

what you said, Great?

Great.

Yeah, yeah, I had multiple pairs. I didn't know.

Common Projects looking.

Yeah, yeah, I bought multiple. I didn't know he was the founder.

Yeah.

Wow.

Yeah, so incredible operator. And then like, yeah, he's still, uh, I think his team is like 5 or 6 people.

No, well, Jolie. 5 people.

I think so. He talks about it. I haven't caught up with him in a while.

No idea.

Wow.

Yeah. And I was lucky enough to— I invested in that pre-launch, again, just because of knowing his background and how I'd met him a bunch of times and seeing his conviction. I had no idea if filtered showerheads was a good product or if that made any sense. But him as an operator and just him talking through what that launch strategy was going to be, was super compelling.

I was like, I have a filtered shower head.

Do you have a drill?

Yeah.

Oh, and then I actually have a— I have a friend who started a competitor called Filter Baby. They started with the sink, they just launched their shower head. They did like a month or two ago.

Canopy did too, the humidifier to the shower.

They did a shower head also?

Yeah.

Yeah, I didn't—

yeah, let's tell you, created the category and then of course you're going to get competitors following.

Yeah, of course.

One thing I want to talk about is You mentioned investing in Jolie and then building client roster at Paul Street without having to do really much outbound or sales or BD. Talk to me about the value of compounding networks in a very, very specific ecosystem. I think everyone, if they've experienced the value of compounding a little bit of staying in a business for a while, they can kind of see it like Wayflyer growing very quickly. But just the personal networks of like, I have some friends that did VC, then SaaS, then a brand, then go to an agency, and you have to start over. Like maybe you have a little overlap, but you basically have to start over versus being in e-commerce, I don't know, 6 years, 10 years, 20 years. Like it just gets better and better and better. So what are some of those things? Like the Jolie investment example is a great example of you seeing the value firsthand of like, hey, if I went and built a SaaS tool, things may have been different.

Yeah, I think, well, like the value of the network, I think like we talked about it, earlier, there's a lot of immeasurable connections that kind of come through which don't even— it's hard to even map back. It's like, oh, some people just like organically sign up on the website and it turns out they might have been talking to someone that me or Aaron have like known. Yeah. Or something like that. I think the other like value of a network might— and just being in one specific industry, if you're more leaning into that side of the question, Like, knowing that Paul Street was a great opportunity was more from being in the ecosystem and talking to a lot of these founders who needed this service. And like, if you would have asked me 2, 3 years ago, like, are you going to found a marketing agency of any kind? I'd be like, I doubt it. I don't know.

Bootstrapped marketing agency.

Yeah, but then from, again, from being in the network, talking to these founders, talking to other people who have SaaS companies or even other agencies, and then talking to Aaron, and then again, because there's months between talking to Aaron and then actually pulling the trigger and starting the company, I was constantly talking to founders that whole time and having more of an eye out for Uh, when we first started, it was media buying growth affiliates. Um, and any brand I talked to was like, that, I mean, yeah, that I need that. I don't really understand that. I'd like to learn more or talk about that. I was like, oh, you just talk to Aaron. Um, and then I think have— but by sticking to like focusing on one industry, you then become the expert. And like, you become an expert in that specific topic. I think that's where the value really is. Sure, there's business development opportunities, but I think that's less important more so than knowing the right opportunities and like actually understanding what is a good product or service or whatever it is. So I could understand this is actually a really good service offering, that there wasn't great competitors serving the clients that we were going after and serving the clients we knew we had access to. And so I found that way more valuable, knowing that that was going to be a or knowing that had a good chance of being a successful business.

What is the end goal for Ball Street? Um, like, fast forward 5 years, what does the end of the story look like?

Yeah, I mean, me and Aaron talk about this a lot. It— the two options are what? You continue to grow and it's a cash-flowing business, or like, you aim for an exit. Um, so we talk about that at both. I think it's— I think it's smarter to build a company that should be able to last, last and be cash flow positive and be generating like a capital. And with them, that also is a company that would be good to be acquired. And so like, we— I'd say we aim towards building a long-term company that will last 10, 15 years and build a great culture and build a company that we want to stay with for 10 years. If there was the option for a great acquisition along that way, great. Um, but I think if you, if you try to build a company to like be acquired, that gets a little bit dicey where you might make decisions that you shouldn't have made, and then the market might change and you might not be able to be acquired. So we definitely, I think we try to build a company forever. Forever probably being like 10 years. And then yeah, sure, maybe it gets acquired along the way, which I think we'd be happy with, but I don't like to build for that.

This is damn good. I do want to ask before we leave is on that agency journey, something you just talked about is like the same outcomes either way. They may have different inputs on the front end, like making a decision for hypergrowth versus deciding to grow a little slower with the right culture, something that you can see yourself in 20 years. As you think about like that decision matrix, what are those conversations with your co-founder in real time like? Is it just riffing, where heads at, what you're hearing from the market. I'm a solo founder, and so I hired an exec team who I talk about some of this stuff with, but I can't really talk about that with a lot of people. And so I'm curious what those conversations look like.

Yeah, I love those conversations. I don't know.

I'm going to call you more often.

Yeah, solo founders, I don't know how you do it. It's like—

They're crazy.

Yeah, it's wild.

I didn't mean to, man. I would love a co-founder.

Like, you need— I don't know. You need to have those conversations. Me and Aaron are like, I don't know, our relationship is fantastic for having those conversations. Obviously we're talking like every day or whatever, and then probably have more structured conversations on a weekly or depending on what, how big of a decision. Like the strategy conversations we're looking at probably more on a monthly basis in terms of like I said earlier, we don't want to, we can't onboard too many clients. So like we constantly have a pipeline of clients that we're like, OK, we can maybe work with them. That's a good fit. But to work with them, we need to look at the capacity of everyone on each of our teams. What service offering are they going to be working in? How are they going to fit into that team? What does the workload look like for everyone on that team? We need to hire to take on these people. So that's where— we could have brought on way more clients over the last year and a half easily. And that would have been a terrible decision. I think, uh, maybe not, could be wrong, but I think that would have caused us to offer a much lower grade service, and that would have led to issues with our clients, and that would have led to more churn in our clients, that would have led to less referrals of these like huge clients that were now being put in front of and like talking to. Um, so, and me and Aaron are aligned on most things, I would say. But have, like, there is like slight things that we go back and forth on, and then it, like, we both definitely need that to come to the right decision.

Yeah.

Um, and I think that being— I think that's the most important conversation or like strategy piece for any company or founder is those decisions of how quickly to grow and how to invest into growth. And like, we also could be a lot more profitable, but we're putting that straight into hiring more people.

Yeah.

Um, like, we could easily just chill out, uh, with the clients we have and the team we have and maybe grow retainers or add a few more clients. But we want to lean into building a much bigger team and, uh, taking— like, it's almost like a hamster wheel is what I've been calling it because you can't have more clients without having more employees, and you can't hire more employees because we're fully bootstrapped. You can't— we need the revenue from the new clients to hire the employees. So every couple— they ask you, sorry, every month, if not every week, we're talking about who— it was like, what roles we need to hire for and what impact those roles will have, what that means for being able to take on more clients and Yeah, I think you like having that, like having the two of us to talk through these conversations. Those conversations can always like drag out and I don't know what we do.

Adrian, you just look in the mirror and talk. Your shadow will give you answers.

Well, you got, you got ChatGPT now.

I just will tell you, last time we, when we caught up a couple weeks ago, I was, I was asking him these exact same questions. I mean, we're targeting this, we're growing this fast. How would you hire? How would you structure I feel like a lot of, I think especially with service-based businesses, you've been here making the wrong decision around growing too fast and maybe someone churns. This cycle in services happens so quickly of someone churns, bad referral, slower beat. Like it's a really slippery slope.

And it's a small ecosystem. And it's a very small community.

I mean, we're not just in e-commerce.

We work with B2B now. Oh yeah, true, true.

But especially early days when like 90% of the people we worked with were like commerce infrastructure. It was— you had to be so careful because like it was, it was not just a slippery slope, but it went down so quickly if something bad happened. You had to be so careful about like reputation and growing slowly.

And yeah, I mean, any agency, uh, we have like an initial term and then most contracts, all contracts go to month to month. So that same— which was hard for me again starting at this. And I think that, yeah, that's common, uh, so, so I believe, but For me, early on, looking at that, like, kind of structure, that was terrifying. It's like, oh, what if you make—

you're gonna have a bad Friday one week.

Yeah.

So in theory, or if there's a shift in the market that, like, every brand— because what's the first thing you're probably going to get rid of is, like, a marketing agency, or, or if it's really bad, it could be every vendor. Yeah, every vendor that your contract allows, which will tick that box. And that is still scary. But I think as we've— now we have clients that have been with us for 20-something months, it's like, oh, okay, maybe they won't leave us.

And if you— and if you're able to crack into like the upper tier of the market, it's like— but yeah, if you're losing everyone, it's probably a business problem.

If you're—

if the largest brands in the market are like churning. But I think that's something you deal with. I think every business deals with that in one form or another. I'm gonna leave you with one last question. Looking back on your journey to date, what would you say is the number one turning pro moment?

Um, turning pro moment, I actually think it's probably something more recently. Certainly having— I think probably having your own business is like the pro, going into the pro phase. Um, and like more recently, so we have our first offsite, uh, coming up in 2 weeks, 3 weeks, and we've booked out a hotel in Prince Edward County. And like most of our team is— most of our North American team is in was in Toronto. So like, just even like having that booked in and seeing that we have like 20-something people coming to a hotel and offsite, um, felt pretty professional.

It's really cool. Yeah, congrats. It's a big milestone.

Thank you.

When everyone's there and also there from the business that you brought in, the company that you grew, and the company that you're scaling, it's a, it's a cool moment.

Yeah, it will be. Yeah, we haven't done that. A lot of people just haven't done enough.

So not with— now that we— I mean, we were 10 people at the beginning of Q2, we're 25 now. So like, we haven't done it with the, the new team, if you will. But I think, I think 2025 will— it'll be a goal.

I'm excited for you guys to finally get that feeling.

Yeah, we got to get there.

Thank you so much for coming on.

Thank you.

To the camera on the far left, tell people where they can find you and Paul Street.

Yeah, you can find paulstreet.co is the website. Uh, my Twitter, which I don't really do anything on that, but I might start posting more. It's Paddy Clearly. Uh, or LinkedIn. I'm on LinkedIn. Uh, Patrick Cleary, Paul Street.

Oh yeah, that's a great plug. I might start posting, so follow me.

I've been saying that for like 2 years.

Thanks for coming on, man.

This is great.