Andrew Brown - Check

Check: Building a SaaS Startup You’re Not Rushing to Sell – with Andrew Brown [373]

Check: Building a SaaS Startup You're Not Rushing to Sell

Andrew Brown is the founder and CEO of Check, a payroll infrastructure startup that embeds payroll directly into other software platforms.

In 2015, Andrew sold his B2C startup, Oyster, to Google. But that big win also left a void in his professional life. He decided his next startup would be something he could work on for a decade or more, rather than just aiming for a quick sell-off.

After spending years carefully searching for the right business idea, Andrew finally landed on the concept for Check when a potential partner revealed just how complex it was to build payroll functionality directly into their HR platform.

Andrew spent several years operating in stealth mode, entirely focused on establishing Check's initial product and early partnerships before ever officially launching.

But earning trust was much harder than Andrew expected, with many early prospects questioning why they should trust an early-stage startup with their payroll solution.

It took years of relationship building through warm introductions, thoughtful cold outreach, and diligently preparing for every meeting to finally land pilots with initial partners.

As Andrew described, payroll is an incredibly complex 50-state problem requiring going state-by-state to ensure proper setup before anyone will trust you with money.

Today, Check has grown to a team of over 100 people and raised $119 million so far.

In this episode, you'll learn:

  • Why Andrew felt unfulfilled after selling his first startup and decided he wasn't going to be in a rush to sell his next company.
  • How feedback from a potential partner about payroll complexity revealed the startup opportunity Andrew eventually pursued with Check.
  • Why Andrew believed staying in stealth mode for years pre-launch was crucial for Check's initial product and partnerships.
  • How Andrew creatively earned the trust of early payroll customers despite Check being an unknown quantity and a stealth startup.
  • Why Andrew believes the opportunity for embedded payroll solution is massive despite there only being a few hundred potential customers in the target market.

I hope you enjoy it.


Click to view transcript

This is a machine-generated transcript.

[00:00:00] Omer: Andrew, welcome to the show.

[00:00:01] Andrew: Thanks for having me on today, Omer.

[00:00:03] Omer: Do you have a favorite quote? Something that inspires or motivates you that you can share with us?

[00:00:08] Andrew: I love the William Gibson quote that the future is already here. It's just not evenly distributed. That's I think about that all the time as we build product.

[00:00:17] Omer: Love that. So tell us about Check. What does the product do? Who's it for? And what's the main problem you're helping to solve?

[00:00:25] Andrew: Check is a platform for building new payroll products and businesses. So let me explain what that means and why does anyone need a new payroll service? You know, most folks like, hey, every company has payroll already.

So the way we think about it is a small business owner. Historically, they might have managed their business on pen and paper. Over the last 10 years, they've begun to use some sort of platform. You can think of, you know, the squares and toasts of the world to actually run their business every day. Now, payroll historically has been a whole other separate system disconnected from that core one that they're using to run their business.

That makes no sense to us. We think as a small business owner, you have way more things to do than you have time to think about them. Payroll should not be on that list. So what we do is we work with those platforms, folks like Homebase and Housecall Pro, who are our customers, so that payroll is baked into that workflow.

It's part of the everyday platform for the small business

[00:01:20] Omer: owner. Can you give us a sense of the size of the business? Where are you in terms of revenue, customers, size of

[00:01:26] Andrew: team? Yeah, so Check is a Series C company. We're a little over four years into the business now. The partners who we work with power hundreds of thousands of businesses, more than 3 million employees across all 50 states in the US and DC.

And we're about a hundred or so people.

[00:01:45] Omer: And I think it totally raised about 119 million.

[00:01:50] Andrew: That's correct. Yeah. We've been really fortunate to be backed by, you know, incredible investors, Stripe, Thrive, Index, Bedrock Capital and a slew of amazing angels as well.

[00:02:00] Omer: So, let's talk about what you were doing before you founded Check.

You spent some time at Google and then you, you know, jumped into the startup world, but your first company was a B2C business, is that right?

[00:02:17] Andrew: That's right. My first company was called Oyster. And it was a subscription service for eBooks. So think Spotify or Netflix, but for eBooks and you would access that, you know, on your phone, your tablet, you know, those sorts of devices.

And it was started at about a year out of school. I was 23 and had to be an amazing kind of four-year run there. And

[00:02:37] Omer: just give us a kind of the short version of the story. Like how did you. Come up with the idea for that business and, you know, like who, who did you build it with? Cause you had some co-founders with you on that business, right?

[00:02:52] Andrew: Yeah, I had two partners in that business Eric and Willem and the three of us were really, one, we loved books. We loved reading speaking for myself, definitely a nerd. And, you know, always as a kid, spent a lot of time at the library. And so we had that experience on the one hand, and on the other hand, you know, we loved Netflix.

Spotify at the time was relatively new. We loved what they had brought to music. And we said, hey, why couldn't we bring this, you know, unlimited subscription, I'll call it a more modern version of a library type of model, to You know, the book industry, that seemed like something that someone should do. And we thought we were based in New York at the time.

New York, I mean, still am, but New York was a much smaller tech scene than the publishing industry was based here. We said, you know what, we you know, we know how to build software. Willem's an incredible designer. Eric knew how to do BD deals. We were in the right place. We said, Hey, let's go take a swing at this thing and, you know, try and convince these, in some cases, you know, multi-hundred-year-old publishing companies to take a shot on some 20-something-year-old guys on trying a totally new business model. I

[00:03:53] Omer: think you ran that business for three or four years, grew it to about 7 million in ARR, and then you ended up selling it to Google.

[00:04:02] Andrew: That's exactly right. Yeah, we were, we were really fortunate with you know, the trajectory of that business and, and it's interesting.

I think I learned a lot there that Google had the Google Play Store. And in post part of that, you know, they had an ebook app and a music app and a video app, et cetera. But I think ebooks for them had been underinvested in. And you know, they looked at what we had been able to build and really the, I think, consumer love that we'd been able to generate.

And they said, hey, if you plug that you know, kind of product and that consumer love into our amazing distribution engine where this app is literally pre installed on every Android device in the entire world. You know, we can really build something, you know, pretty interesting. And, you know, that was the core thesis behind the deal.

[00:04:43] Omer: And so you ended up spending another three or so years working at Google after that acquisition and, you know, until you came up with the idea of a check. So, so tell me about how that idea was born because You know, you've gone through, you've had a successful exit with a B2C business and now suddenly you're going into B2B, enterprise, completely different world.

Like where did that idea come from?

[00:05:10] Andrew: If I can take one step back, I think this is where the story really gets interesting. You know, you've got this trajectory. We started this company, we sold it. You know, those three years at Google were tough for me. I honestly, like, while the acquisition was exciting from the outside, it was not the outcome that I wanted.

I wanted to build Spotify. I wanted to build Netflix. I loved running the business. I loved our team and kind of post-acquisition life was was just a very different And, you know, I think any founder would tell you, certainly this was true for me, you know, you work your butt off to build something and then kind of overnight it's like, wait, this is gone or it's totally different.

Like what? It's very disorienting. You know, it's like, what kind of a pillar of your life has gone? What are you going to do next? And so I spent a lot of those, those kind of call it a two year period there. Trying to figure out one, did I want to start another company? Did I have that in me? And then two, how is I going to be damn sure that whatever I did next, you know, really was something that I was going to be able to run for the long haul and, you know, and build into, you know, what our, our goal still is.

And I believe check will be, which is a, you know, generational business that stands the test of time. So that was a. It's a really high bar to clear. It's part of why it took me three years, I think, to ultimately find the idea. But once we got there, you know, we've been off to the races.

[00:06:27] Omer: So that's interesting.

Every founder, you know, talks about having a successful exit and you, you had one. But what I heard was, hey, it wasn't. You know, all that great in, you know, other aspects of, you know, my, my, my life and, and personal fulfillment. And so when I went out for this next business, yeah, I still maybe wanted to have a, an exit at some point, but not too quickly.

Something that I could work on for, for many years and build and grow and so on. Is that kind of what I'm, what I'm hearing?

[00:07:03] Andrew: That's a hundred percent right.

[00:07:04] Omer: That's interesting. So, so what happened? So you, you, you kind of got this very high bar for figuring out this business you know, what this business is going to be, like, where did the idea come from?

[00:07:17] Andrew: In some ways, probably it's, it's a good problem to have. It's a second-time founder problem, but I had basically the team lined up. I had folks that I had, you know, I brought on and worked really closely with at Oyster, who I was really close with. We wanted to work together. I had investors that wanted to back us, basically all the makings of a company, but we didn't have the idea.

That was the hardest part of of starting Check. And it's funny because the thing that came first was we identified. Basically, the shape of the idea that we wanted, which was I had done a consumer business. I did not want to do consumer again. I knew that, you know, running Instagram and you know, Google AdWords all day was just not my, my cup of tea.

I wanted a pretty analytical, logical guy. I wanted a B2B, ideally sort of enterprise y business. I'm an engineer by background. So if it was a platform that folks could build on even better and I studied economics in undergrad too. So I've always liked kind of. big economic systems. And so fintech really interested me.

So I was basically looking at a whole slew of opportunities in that general realm. You know, what were things that were going to fit that criteria? And so then we ultimately came to check. The really sort of key insight and key, you know, way we came to the idea was actually it wasn't some, you know, brilliant top down analysis on our part.

Check was the product of customer pain. One of our earliest, still most important partners, Homebase, wanted to build payroll. They are a scheduling and time tracking tool for like local main street businesses all across the country. Think, you know, coffee shops, restaurants, those sorts of things. And you know, they were really banging their head against the wall, like, Hey, we've got to provide this service to our customers.

They want it. It'll be amazing business for us. And payroll was just too complex for them to build internally. And so I, we were close to the team over there and had gotten to know them and we said, Hey, This is a business. If we do this, we can provide this service to you and then this same platform to all sorts of other, you know, vertical SaaS and kind of HR businesses all across the country so that no one has to go tackle this complexity of payroll on their own ever again.

[00:09:25] Omer: Okay, great. So you, you see this opportunity. There's, there's clearly a pain that somebody wants to go and solve. To me, it doesn't sound like the kind of payroll solution that you build, you know, this kind of embedded. payroll or payroll as an, as you know, as an API. It doesn't sound like the kind of thing you build as an MVP in a couple of months and, and get in front of customers.

So what approach did you have to take in terms of building the right, you know, first version of the product?

[00:09:55] Andrew: Yeah, you're absolutely right. So we spent the first two full years in stealth and raise two or even three rounds of capital, all while in that stealth mode, just working on the product. And that's both because payroll is complicated and because it is a massive 50 state problem.

You have to go state by state, in some cases even county by county, school district by school district, making sure you have the tax rates correct, you've integrated them in the right way, you're able to pay the taxes in the right way. It's an incredibly complex problem. So there were… There's really two sides to that.

One is, you know, you have to, maybe three. One, you have to fund it so that you can do that. Second, you have to convince customers somewhere along the way to start using you so that you can, you know, get some feedback and, and build trust with them. And then I think third is you got to figure out how to still create like.

Energy and momentum and urgency internally on a day by day basis. And, and, and that last one is maybe the one that I think we spent the most time on early on, because it was clear how big a problem and how hard a problem it was going to be. And I think our single best tactic there is that we built our own, like we ran on our own system.

So my co-founder Vivek and I, we refused to pay ourselves until we could run it on our own platform. When we'd hire new people onto the team, if they were in a different state, we would make them, you know. Build support for their state, basically, before they could get their paycheck. And, you know, that added that real sense of urgency to to the work.

[00:11:21] Omer: And did you, did you get any commitment from Homebase? So, in, in terms of some letter of intent or, or, or something before you set out on this journey to build a solution, you know, over the next couple of years?

[00:11:36] Andrew: The short answer is no, we probably should have in retrospect but you know, I think truly so many things in, in the business world are based on trust and it's actually honestly goes a lot deeper than, you know, any piece of paper would.

And so from the early days, I think we understood that when, what we built Homebase would use, and that was really for the first. And you know, what we were chasing. And then once we turned the page to year two, at that point, we did have signed you know, LOIs or something like that from Homebase and one maybe two other platforms.

And then it was still probably another six months after that before we had our first like truly signed contract.

[00:12:14] Omer: You know, when I talk to founders like yourselves, the first thing we, we talk about is like those, you know, the first 10 customers and with you guys, as you were explaining to me earlier, it wasn't that simple.

It took you several years just to even get the first four or five customers, each one being very significant. It wasn't like, you know, a hundred bucks a month type customer. Can you give us an overview of what? What it took to, to sign a customer like that, like what, what was the process that you had to go through?

I mean, with Homebase, you said you had some existing relationships and maybe there's some level of trust and people are more open to being willing to work with you. But when you're going into. You know, a business is saying, Hey, we're a startup and we can help you with your payroll. It's like, really?

It's like, how can I trust you? Right. So what was your experience with that?

[00:13:10] Andrew: Yeah. Our second company value is earned trust for exactly this reason. Cause I had so many people early on who said. Literally the exact words that just came out of your mouth, like this sounds good, but how can I trust you? Why would we work with you?

So, you know, that's hard to combat. There were a few things that we did. First of all, like our two main tactics were really network based using our own investors, folks we knew. You know, relationships we were able to generate to get introductions and sort of create that trust by association. You know, that was tactic one.

And far and away was our most important and still an incredibly helpful, you know, channel of distribution for us. The other one was really cold outreach. We were fortunate in that we had a unique product in the market. And a very specific set of folks, like we could literally write down the names of a few hundred companies that we wanted to talk with.

And it was normally, you know, one of two or three people at the company that we should get in front of. And so I'd write a really thoughtful, cold email to them. And, you know, I think, I think attention to detail and crafts. sort of conveys trust in a way that maybe folks underappreciate, especially when done repeatedly.

So when that first cold email is great, when you get on a first call and are incredibly prepared and you, you know, go see someone in person and have done research on their business or talk to their customers, you know, you don't do it all in one day, but it's little by little through each of those interactions over time, you build it up and eventually, you know, You give them an AAPI key.

They try the platform, they love the platform, and it all builds on itself.

[00:14:36] Omer: Yeah, that's, that's interesting. I, I want to talk a little bit more about you know, growth and, and the enterprise sales process. But one thing, you know, you mentioned that you had a very targeted list of potential customers in terms of your.

The number of customers in your total addressable market wasn't that big. You're talking about hundreds of customers. I think, you know, maybe somebody looking at that initially, when in the early days of doing research, they may just say, ah, I'm not sure there's a big enough opportunity here, right? The market is not big enough.

So. It may be the number of customers wasn't huge, but the, the, the value behind each potential partnership or deal was, was significant enough to, to drive you. But can you just help us understand a little bit about how you thought about the opportunity here?

[00:15:21] Andrew: Absolutely. So I think the key thing to understand about Check is that we really have a two phase growth motion.

So we, you know, work with our customers. We call them partners. And then they serve typically tens or hundreds of thousands of small and medium sized businesses each. Potentially millions of employees each. And so what that means is that when you think about our total market we really think of ourselves as being able to address You know, every single business, every single employee that works in this country today, and eventually in other countries, you know, all around the world, payroll is a very old, absolutely massive space that you can look at and see, you know, there's many companies worth tens of billions of dollars in it, and frankly, none of them are, you know, innovating at an incredibly high rate.

And so I think both we and, you know, our investors and frankly, our partners too, see that as the opportunity. We see providing a absolutely customized, just something that almost so easy to use that fades into the background experience for payroll for every single one of those companies as, as the prize that we're chasing.

The challenge then is how do you address that? And that's where our partners come in. Those are the ones who, you know, it's hundreds of them and they're each quite large. And those are the key relationships we have to establish.

[00:16:33] Omer: Yeah, I mean, I think that's the really smart thing here that having that, you know, a very finite list of potential partnerships that you can do helps you take the time, I think, to build more relationships, to network and so on, rather than, you know, mindlessly sending out, you know, a few hundred cold emails that look pretty much the same to anybody and everybody.

[00:16:59] Andrew: Totally. It's a bespoke custom, you know, in the weeds business for sure. And importantly, and we haven't mentioned this, like there's not only a go to market side of that, there's a product side to that too, where, you know, check as a platform looks totally different than any other payroll company that has ever been built in the past.

It's so not only is there an API for it, which is sort of easy to say, you know, the actual architecture under the hood is incredibly customizable. It's very powerful and scalable. And it gives folks the ability to then, you know, actually build their own you know, products kind of lean into their own creativity on top of it in a way that I think no one had ever really imagined before.

We're kind of taking this like old stodgy sort of service-based industry and almost turning it, you know, inside out on its head and redistributing much of the value of the industry to, you know, these platforms that really now own the customer relationship.

[00:17:50] Omer: So let's talk a little bit more about the sales and onboarding.

You told us a little bit about, you know, some of the challenges and the importance of building trust. Typically, what have you been finding? How long does it take to close this type of deal? And then I think, you know, once you've closed it, it sounds like that's when… The work actually begins.

[00:18:13] Andrew: A hundred percent.

Yeah. The work definitely starts there. So I'd say that initial sale process, it can vary because, you know, you have to, our partners are really setting up a new business line when they get into payroll. And so they have to be ready for that. But I would say a typical sales cycle for us can look like anything from a few weeks for a small startup up to, you know, we work with public companies as well.

And those can be, you know, a year, maybe more, you know, it can certainly be several quarters. So there's a fair amount of variability, but maybe call it average is two quarters, something along those lines, long enough to, you know, get to know them, build a relationship, give them time to, you know, assess the platform and then sort of get it on their roadmap.

[00:18:52] Omer: And then tell us about what happens once they've, you know, the deal has been onboarding a new customer or partner.

[00:19:03] Andrew: Yeah, we think of really three phases. The first one is getting to launch. You gotta go from signature to launch. Then we think about how we help you grow. So you have to kind of, you gotta get those first few reps in. Everything we've been talking about here, how do you get those first 10 customers?

Each of our partners has to understand how they get their first, you know, 10 customers for their payroll service. And then it's all about scaling it from there. So that means those first, call it quarter or so, normally our partners are trying to launch within You know, anywhere from, you know, a couple of months to a few months you know, it's working really closely together with our partner engineering team to help guide them on their setup and launch.

And then once they get past that, we have basically a growth consulting team that goes in and works really closely with them. Sometimes it's, you know, in the office sitting next to their salespeople, giving them feedback as they're on their first few calls, you know, helping them stand up this distribution motion.

And then from there, once they've kind of, you know, have the momentum going and really the wheels are in motion, at that point, we take a little bit of a step back and then we're, you're in scale mode. And that's where we're, you know, trying to understand where are they blocked. What do they think they might be able to, you know, expand into another sub-segment they serve if they integrate with some part of our system, or we offer a new feature, things of that nature.

[00:20:13] Omer: Can you tell us a little bit about your pricing model? I think, you know, maybe somebody listening to this is might be thinking, well, You know, having a growth team to help a customer kind of sounds a bit overkill, but with, with you guys, from what I understand in your pricing, like it's, it's really dependent on, your growth is dependent on the success of your partners is right.

[00:20:38] Andrew: Exactly. And this is a very I think common thing for embedded fintech. So if you think about some of the largest brands out there, think about stripe, think about a firm you know, companies of that nature. It's similar. You know, if you're a firm, how Spotify or not Spotify does and your, you know, partnership with them is huge to you.

And if that's worth investing a lot in our business is very similar. And so our pricing is entirely aligned with the incentives of our customers, which means we get paid a certain flat amount. Based on the number of employees and number of companies that they're running payroll for at any given time.

So it is all about how do they grow their business and if their business grows, you know, we keep a smaller portion of that and our business grows as well.

[00:21:18] Omer: In terms of hitting the first million in ARR, I think it took you guys a couple of years or so to get there. Aside from this, this whole thing about, you know, going out and networking and building trust, looking back, what do you think, what else was You know, one of the biggest challenges or, you know, obstacles to, to hitting that first big milestone of a million in ARR.

[00:21:47] Andrew: Yeah. And I'll say it was really, it was probably about three years, I think, to get to that first million for us, because again, you've got to sign all the partnerships, get them live, get them launched and get them growing at, you know, before we got there and there were. Look, there are several pieces that are fundamental to the model.

Yes, it's the partnerships. And yes, it's also the complexity of payroll actually building out that product. Those were two, you know, huge things. But there was also the idiosyncratic stuff you wouldn't expect. COVID hitting was just a massive you know, sideswipe for us as it was for so many businesses.

In our case, I think we were in that period in between having letters of intent. But not yet signed contracts. Keep in mind, all of our partners serve small businesses and mostly, frankly, in the real world, blue-collar workers. Those people weren't doing anything, at least for those first few weeks, first few months.

It was very unclear. Were our partners businesses going to even, I mean, were their customers going to exist anymore, number one? Then were they going to exist? Much less, were they going to prioritize payroll? You know, there were some scary moments there. But I think we learned two. Really amazing lessons from that.

Number one is how critical we were to the future of our partners businesses. Not only did they survive, they didn't cut payroll, even while they might've done layoffs and cut many other initiatives because we were part of their core. We were their future and they wanted to bet on their future. So that was number one.

And then number two, we learned how to really be adaptable and how to be great partners. What I mean by that is one of the folks we were working with, their companies had Light off a ton of people and their hypothesis was that as COVID began to ebb, they were going to want to hire many of those people back.

And so we worked with them to build some really sophisticated, essentially onboarding you know, software that deals with, you know, state forms and all those sorts of stuff. And did that really quickly, you know, as a matter of like a six or eight-week sprint together to help build this, you know, sort of do sub product, if you will, sort of an onboarding into payroll in order to really help.

Them out and help their customers out as they came out of it. And, you know, that generated maybe some tiny amount of revenue. But, the real thing it did was it cemented the partnership. It cemented how we could work together and this idea that we were gonna grow our businesses side by side.

[00:23:55] Omer: You, you mentioned you'd been in stealth mode for, for a few years.

I'm curious, what was the. What was the main kind of driving reason behind that and, you know, sort of looking back, do you feel like timing-wise it was the right thing to spend those, you know, two or three years in stealth mode or maybe, you know, looking back, you would have done it differently?

[00:24:20] Andrew: It was 100 percent the right call to be in stealth mode for those two years.

If I had to do anything, I might have waited another six or 12 months to come out of stealth, but you got to do it eventually. And there are a couple of reasons for that. I mean, number one, probably the most important one is that we felt like we had a differentiated insight about the world. You know, that common question, like, what's the thing you believe about the world that no one else does?

I think for us, the answer to that question was that there needed to be an order of magnitude more payroll products out there than there were today. And they're just there. We were fortunate to be in a position to be able to put the pieces together to see that. And You know, we didn't really want to, you know, tell others about that until we felt like we had kind of broken out.

That was one. And then two, we needed time to build the product. We didn't want to be out there sort of selling something that didn't exist. And we wanted to make sure we really built it in a first class, you know, very reliable way. Something you were going to have to go, you know, hack together and redo at the end of the day.

And I think that served us, you know, really well.

[00:25:17] Omer: So you, you, you and I were talking earlier and we… You know, I was saying that, you know, it looked like you were, you know, raising money like clockwork, like you, you launched January, 2019, the January next year, you raise. You know, 8 million Series A, the January next year, 35 million and so on.

How, I'm trying to figure out like, you know, one you're in stealth mode, two, you're still building a a product. You, you potentially only have a handful of customers at that point. How easy or hard was it to raise that money and how important. Was that funding to you to be able to build the kind of product that you believe you needed to build?

[00:26:01] Andrew: The answer is the funding was crucial. Payroll is a, a deeply complex state by state product and something that requires a lot of upfront investment. You know, the, the sort of, there's not much of a thing of an MVP, you know, within within payroll. And the IRS, frankly, does not care whether you're six months old or 60 years old.

They expect you to do everything, you know, the exact same way. And so, you know, with that in mind, this is definitely a business that needed to be venture backed. The funding was crucial to us. And frankly, it was crucial to be able to set up the right incentives where our incentive matched our partners.

We didn't have to ask them to, you know, pay us a lot of money before we had delivered any value to them. So that was one. In terms of the ease of raising the funds, I think we were in a really fortunate spot where none of our fundraisers were ever particularly difficult. And there were a few factors there.

One, the fact that I was a second time successful founder, you know, for those first couple of rounds definitely went a long way. I think we executed really well through those first couple of years and folks saw that. They saw that we were actually very quickly building something that was very complex and the market was responding to that.

We were signing up amazing, you know, partners. And then lastly, it was just the size of the opportunity. Again, this is something that Every single business across the entire country needs in a market where the incumbents are just really not pushing the state of the art forward, and, you know, that's, that's kind of what, you know, venture capitalists dream of, and, and so I think we're able to detract quite a bit of attention in dollars.

[00:27:23] Omer: What does the competitive landscape look like today? So, you know, it's, it's 2019. So we're talking about, you know, four or five years, you've been working on this business. You looked at the incumbents back then, you know, players like ADP and there wasn't really much going on there. And that's what helped you to believe you had an opportunity to disrupt and, and, you know, create a better solution. Has much changed in those last four or five years?

[00:27:53] Andrew: I would say from the big guys, the, the big established payroll companies. Not really is the answer. I mean, if you go to their websites, they all have some, you know, generative AI chatbot strategy now or something or other.

But you know, you tell me if that's really changing the payroll experience all that much for them. They're pretty much doing the same thing they've been doing for the last 50 years. And there are definitely other companies who have seen, you know, the, really the whole category of embedded payroll, the check is now created and have tried to come in and, and.

You know, compete with us, which I think is healthy and you know, has helped, frankly, push the whole market forward. But it's, it's very much broken out where there's kind of a, I would call it a historical, you know, kind of payroll set of incumbents. And then, you know, the, the insurgents of which, you know, we are the, the dominant one over on the other side, trying to, you know, really evangelize this idea that embedded payroll is the future.

[00:28:42] Omer: And that's interesting with these new players coming into the space, going back to what we talked about with going into stealth mode. Do you, do you feel that that again gave you an edge because you had a little bit of time to… Establish yourself in terms of being, being a leader in this space.

[00:29:02] Andrew: Totally. We got a two to three year head start over everyone else. And we saw it, even the big incumbents in terms of how they reacted. You know, there was a, they're pretty wide eyed. You could tell, you know, once we came into the end of the market. So that's a huge part of why I'm glad we did it.

[00:29:15] Omer: So, you know, with your story, it, It's a great one, like we, we talked about, you know, coming up with this idea for Oyster, working on that for a few years, selling it to Google then going from B2C to B2B, building Check raising well over a hundred million dollars, you know, you, you make it look.

Easy. And so just for a reality check for people who are listening to this and not finding it as easy, give us a maybe a flavor of maybe, you know, some of the difficulties or challenges that you've also faced.

[00:29:56] Andrew: I will say it has not felt easy, first of all, and you know, for those watching, they can see the gray in my beard that this comes from having built those two companies, you know, there's the typical stuff, the, you know, the late nights, the, you know, working through weekends, the, you know, missing important occasions, things like that, like that, that's definitely been true for me, as I know, as it is for so many entrepreneurs.

And it's one thing to do that for sure. You know, a quarter, six months, a year, you know, I've been over across these two companies at this for, you know, a decade or so at this point, maybe a little more. That's that point you're talking about your life, right? It's like, what are you dedicating it to? And, you know, that's a whole other thing that you got to figure out how to create the right, I don't even call it balance, but integration.

You know, between your life and, and your, your work, your passion, the company that you're building. So more than anything else, that's, that's what I'd say, you know, I, not only did I go through the one acquisition, which was exciting, and at the same time, not what I wanted on the personal side, I went through a divorce in that period too, you know, and so I'll give you another.

You know, recent example of a challenge that we've had to overcome, which was the collapse of Silicon Valley Bank back in Q1 of this year. For context, SVB was the partner bank that we had worked with from the very beginning of our company's life cycle. And as a payroll business, you know, we not only had our own business bank account, we have the account that we on a custodial basis, we're holding all of the funds on behalf of all of the companies that we serve.

And so, you know, the expectation is we, we take those funds and then we pay them out. to employees, right, on Friday morning, typically. Well, SVB decided to collapse overnight between Thursday night and Friday morning. That meant that was the, you know, critical peak time when we are holding those funds that we are trying to pay out for all of those employees.

And, you know, it was probably the worst feeling I've had in my, my whole career was that Friday morning when we woke up. And we saw that the funds were not in anyone's bank account. You know, it's hard to, and, and, and what are you supposed to do to you know, that's, it's hard to imagine kind of a worse situation you know, as a founder of a payroll business.

And truly, you know, for many, like, is this company killing? Like, what are we going to do? And I think we actually managed, it was probably the craziest day of my career, but in a matter of not even 24 hours, turn it from being truly our darkest moment into, I think the proudest day. In the history of the company, because we still, despite the bank being totally shut down through the weekend, everything that was going on, we had to get every single person, you know, that was supposed to be paid through the platform, get them their money before the end of that business day.

And, and that took, you know, moving mountains. We were It took both fast action and a ton of prep ahead of time. So we, we thankfully had our, our corporate funds and other accounts, and we had done quarters and quarters of work to begin to integrate with multiple different banking partners because we knew that reliability and redundancy were going to be very important.

And so as a result of that preparation and then some quick thinking, you know, we were able to move funds around, fall over to other banks, you know, ultimately basically front the money and and get folks paid, do the right thing by our partners.

[00:33:07] Omer: Wow, what a story. You know, I know many startups struggled with that situation, but your situation is, is unique because there were partners dependent on that money.

There were people, employees and small businesses dependent on that. And And saying, well, you know, SVB, nobody would care about that. All they would remember was that you didn't, you didn't work or you didn't deliver the paycheck like you were supposed to.

[00:33:35] Andrew: Totally. We talked about earning trust earlier. I think we actually earned more trust in that one day than we had at any other moment in the company's history, because we were able to show that we went so far above and beyond, and by the way, you know, communicated on a minute by minute basis with every one of our partners throughout the day to let them know what we were doing too.

And you know, that's just it. It goes a long way.

[00:33:57] Omer: Yeah, yeah, definitely. Okay, so before we move on to the lightning round you're coming up to, in a few months, I guess, about five years on this business. When we talked about you finding the idea, you had a very high bar for the type of business you wanted to work on.

So in terms of a five year check, do you feel like the, you, you know, what you've done with this business so far has met? The criteria that the type of business that you wanted to work on and, and also what do you think, you know, the, the future looks like, what, what is the opportunity ahead for you?

[00:34:32] Andrew: Yeah.

I've been reflecting on this a lot recently too, and the answer is a hundred percent. It absolutely meets exactly all of the criteria that I had hoped that it would. And frankly, my favorite part about it is that it feels like we are still just getting started. We have so many things that we still want to build so far to go, you know, truly, if we raise another 500 million tomorrow, I feel like we could have, you know, really high ROI places to go invest it.

And this is a space that truly it's so large and so backwards, there's so much great software that needs to be built. And we're really helping power this just massive wave of vertical SaaS companies and really just custom software for small businesses that you know, is, is really driving so much of the sector of the venture economy right now too.

And I just feel incredibly fortunate to to be in that seat and have such an amazing team around me that, you know, makes my job fun every day. And then. Lastly, I'd be remiss if I didn't mention that the founders and especially the CEOs of, you know, each of our partners, too, who I get to work really closely with, it's one of the most fun parts of my job is we're not just building Check, but we're building an entire, you know, ecosystem of partners built on top of us and other folks who we work with, who, you know, have an ecosystem that help power our partners around Check as well.

And that has been, it's just incredibly rewarding. And I think we're all just growing this whole part of the economy together.

[00:35:50] Omer: Love it, love it. It's a super interesting business. All right, let's let's wrap up. Let's get into the lightning round. I've got seven quickfire questions for you. You ready?

Let's do it. Okay. What's one of the best pieces of business advice you've received?

[00:36:04] Andrew: When someone tells you who they are or shows you who they are, believe them. I think business today is all about people and you just got to believe who, believe what you see.

[00:36:13] Omer: I love that. Love that. What book would you recommend to our audience and why?

[00:36:18] Andrew: There's a book called Reboot, Leadership and the Art of Growing Up, which I think is, again, we talk about business being about people. Leadership first and foremost is about managing yourself, and I think that is the single best book to help you figure out how to really manage yourself and your own emotions in the, you know, towards the end of leading a team.

[00:36:35] Omer: What's one attribute or characteristic in your mind of a successful founder?

[00:36:40] Andrew: Grit and determination. I think at the end of the day, that's you gotta have other things too, but that'll take you an awfully long way. People underestimate hard work.

[00:36:50] Omer: What's your favorite personal productivity tool or habit?

[00:36:55] Andrew: I don't have anything special here. Mine is Apple Notes. I have a note. It is a to do list. It has each day what I want to get done and sort of over the course of the week what I want to get done. And I make sure to get those things done, maybe to a fault. I'm a completionist. If my list is not done, I don't…

I'm not happy. I can't think. I, you know, can't hang out with people. It's all about getting through the to do list.

[00:37:17] Omer: I gotta give props to Apple Notes. I always thought of it as like this. It's kind of super basic notes app. And then I watched the YouTube video the other day and I was like, wow, I didn't know you could do all of this stuff in there.

Apple's very good at hiding, hiding those features. So I don't know if that's good or bad.

[00:37:31] Andrew: They like the minimalist design.

[00:37:32] Omer: Yeah. What's a new or crazy business idea you'd love to pursue if you had the extra time?

[00:37:37] Andrew: Oh, we talked about SVB earlier. I would love to buy or build a modern bank. I think the banking infrastructure out there is still kind of a mess, and there's a couple of companies doing this who I'm friends with and I'm big fans of.

I hope they succeed. If they don't, then I don't know, in 20 years or something post-check, I may have to go give it another shot.

[00:37:54] Omer: What's an interesting or fun fact about you that most people don't know?

[00:37:57] Andrew: I once camped out for two months in order to get into the Duke-UNC basketball game. I was a camera crazy.

For two months? Two months. Yep. Living in a tent in North Carolina.

[00:38:08] Omer: Wow. And finally, what's one of your most important passions outside of your work?

[00:38:12] Andrew: I love just getting outside, hiking, skiing, you know, anything that gets me into the great outdoors. I think we spend so much time, you know, at our computer and email and Slack opening your eyes and horizons to the beautiful world around us to me is how I kind of rejuvenate myself.

[00:38:26] Omer: Love it. Andrew, thank you so much for joining me. Thank you for sharing your story and some of the lessons you've learned along the way. It really does sound, like it's a super interesting business, as I said, and I think it does really sound like you guys are still just getting started and there's so much more you could be doing.

So I'd love to, you know, keep following up and see where you take this business. If people want to check out, check out, Check, they can go to checkhq. com. And if folks want to get in touch with you, what's the best way for them to do that?

[00:38:57] Andrew: Yeah, just shoot me an email. I'm Andrew at checkhq. com and pretty easy to find on the interwebs and yeah, reach out.

I'd love to stay in touch.

[00:39:05] Omer: Awesome. Thanks, man. It's been a pleasure and I wish you and the team the best of success.

[00:39:09] Andrew: Thanks, Omer. Thanks for having me on.

[00:39:10] Omer: Cheers.

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