Why SaaS Partnerships Work With Just Hundreds of Customers

Omer (00:09.760)
Welcome to another episode of the SaaS Podcast.
I'm your host Omer Khan and this is the show where I interview proven founders and industry experts who share their stories, strategies and insights to help you build, launch and grow your SaaS business.
In this episode, I talk to Andrew Brown and 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 Cheque 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 Chegg'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, fast, 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, at least in the US requiring going state by state to ensure proper setup before anyone will trust you with money.
Today, Check has grown into 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 dec.
He wasn't going to be in such 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.
We also talk about why Andrew believed staying in stealth mode for years before launching was crucial for Chegg'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 and why Andrew believes that the opportunity for embedded payroll solutions is massive despite there only being a few hundred potential customers in the target market.
So I hope you enjoy it.
Andrew, welcome to the show.

Andrew Brown (02:41.620)
Thanks for having me on today.

Omer (02:42.740)
Omer, do you have a favorite quote?
Something that inspires or motivates you that you can share with us?

Andrew Brown (02:48.580)
I love the William Gibson quote that the future is already here.
It's just not evenly distributed.
I think about that all the time as we build product.

Omer (02:57.580)
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?

Andrew Brown (03:06.220)
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, 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 baked into that workflow, that's part of the everyday platform for the small business owner.

Omer (04:00.960)
Can you give us a sense of the size of the business?
Where are you in terms of revenue, customers, size of team?

Andrew Brown (04:08.000)
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 U.S. and D.C. and we're about 100 or so people.

Omer (04:26.270)
And I think in total you've raised about 119 million.

Andrew Brown (04:30.750)
That's correct, yeah.
We've been really fortunate to be backed by incredible investors.
Stripe Thrive Index, Bedrock Capital and a slew of amazing angels as well.

Omer (04:41.790)
So let's talk about what you were doing before you founded chk.
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?

Andrew Brown (04:57.870)
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 a, basically an amazing kind of four year run there.

Omer (05:18.950)
And just give us kind of the short version of the story, like how did you come up with the idea for that business and who did you build it with?
Because you had some co founders with you on that business, right?

Andrew Brown (05:34.070)
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, I'm definitely a nerd and 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 could we bring this unlimited subscription, I'll call it a more modern version of a library type of model.
To 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 then the publishing industry was based here.
We said, you know what, we know how to build software, 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 try and convince these, in some cases multi hundred year old publishing companies to take a shot on some 20 something year old guys on trying a totally new business model.

Omer (06:36.230)
I think you ran that business for three or four years, grew it to about 7 million in AR and then you ended up selling it to Google.

Andrew Brown (06:46.160)
That's exactly right.
Yeah, we were really fortunate with the trajectory of that business.
And it's interesting, I think I learned a lot there, that Google had the Google Play store and as part of that 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 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 kind of product and that consumer, consumer love into our amazing distribution engine where this app is literally pre installed on every Android device in the entire world, we can really build something pretty interesting.
And that was the core thesis behind the deal.

Omer (07:29.580)
And so you ended up spending another three or so years working at Google after that acquisition until you came up with the idea of a check.
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?

Andrew Brown (07:56.340)
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 just a very different beast.
And I think any founder would tell you certainly this was true for me.
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.
It's very disorienting.
It's like a pillar of your life has gone, what are you going to do next?
And so I spent a lot of those, 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 was 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, you know, and build into, you know, what our goal still is.
And I believe check will be, which is a generational business that, that stands the test of time.
So that was 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.

Omer (09:14.690)
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 personal fulfillment.
And so when I went out for this next business, yeah, I still maybe wanted to have an exit at some point, but not too quickly.
Something that I could work on for many years and build and grow and so on.
Is that kind of what I'm hearing?

Andrew Brown (09:50.250)
That's 100% right.

Omer (09:51.690)
That's so interesting.
So what happens?
So you kind of got this very high bar for figuring out this business, what this business is going to be.
Where did the idea come from?

Andrew Brown (10:04.830)
In some ways, probably 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 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 starting Check.
And it's funny because the thing that came first is 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 way we came to the idea was actually it wasn't some 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 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 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.

Omer (12:13.190)
Okay, great.
So you see this opportunity, 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 this kind of embedded payroll or payroll as an API.
It doesn't sound like the kind of thing you build as an MVP in a couple of months and get in front of customers.
So what approach did you have to take in terms of building the right first version of the product?

Andrew Brown (12:43.880)
Yeah, you're absolutely right.
So we spent the first two full years in stealth and raised two or maybe 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 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 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 build support for their state basically before they could get their paycheck.
And that added that real sense of urgency to the work.

Omer (14:10.030)
And did you get any commitment from home base?
So in terms of some letter of intent or something before you set out on this journey to build a solution over the next couple of years, the

Andrew Brown (14:25.290)
short answer is no.
We probably should have in retrospect, but I think truly so many things in the business world are based on trust and it actually honestly goes a lot deeper than 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 year or so of the company, what we were chasing.
And then once we turned the page to year two, at that point, we did have signed 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 truly signed contract.

Omer (15:04.490)
When I talk to founders like yourselves, the first thing we talk about is 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, 100 bucks a month type customer.
Can you give us an overview of 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 a business and 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?

Andrew Brown (16:00.790)
Yeah, our second company, Value is earned trust for exactly this reason.
Because 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 that's hard to combat.
There are a few things that we did.
First of all, our two main tactics were really network based.
Using our own investors folks, we knew relationships we were able to generate to get introductions and create that trust by association.
That was tactic one.
Far and away was our most important and still an incredibly helpful channel of distribution.
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.
We could literally write down the names of a few hundred companies that we wanted to talk with and it was normally one of two or three people at the company that we should get in front of.
I'd write a really thoughtful cold email to them.
I think attention to detail and craft conveys trust in a way that maybe folks underappreciate, especially when done repeatedly.
When that first cold email, when you get on a first call and are incredibly prepared and you go see someone in person and have done research on their business or talk to their customers, 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 give them an API key.
They try the platform, they love the platform and it all builds on itself.

Omer (17:27.470)
That's interesting.
I want to talk a little bit more about growth and the enterprise sales process, but one thing you mentioned that you had a very targeted list of potential customers in terms of the number of customers in your total addressable market, wasn't that big.
You're talking about hundreds of customers.
I think maybe somebody looking at that initially, 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 maybe 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?

Andrew Brown (18:13.540)
Absolutely.
So I think the key thing to understand about Czech 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.
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 every single business, every single employee that works in this country today and eventually in other countries all around the world.
Payroll is a very old, absolutely massive space that you can look at and see there's many companies worth tens of billions of dollars in it and frankly none of them are innovating at an incredibly high rate.
And so I think both we and our investors, and frankly our partners too, see that is 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 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.

Omer (19:26.120)
Yeah, I mean, I think that's the really smart thing here, that having that 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 mindlessly sending out a few hundred cold emails that look pretty much the same to anybody and everybody.

Andrew Brown (19:52.410)
Totally.
It's a bespoke custom in the weeds business for sure.
And importantly, and we haven't mentioned this, there's not only a go to market side of that, there's a product side to that too, where check as a platform looks totally different than any other payroll company that has ever been built in the past.
Not only is there an API for it, which is easy to say, the actual architecture under the hood is incredibly customizable.
It's very powerful and scalable and it gives folks the ability to then 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.

Omer (20:44.760)
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.

Andrew Brown (21:07.440)
100%, 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.
We work with public companies as well.
And those can be a year, maybe more.
It can certainly be several quarters.
So there's a fair amount of variability, but maybe call it average is 2/4, something along those lines, long enough to get to know them, build a relationship, give them time to assess the platform and then get it on their roadmap

Omer (21:46.270)
and then tell us about what happens once they've, you know, the deal has been signed.
What's.
What's involved in actually, you know, onboarding a new customer or partner?

Andrew Brown (21:57.430)
Yeah, we think of really three phases.
The first one is getting to launch.
You got to go from signature to launch.
Then we think about how we help you grow.
So you have to kind of, you got to 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 there from first 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 anywhere from a couple of months to a few months.
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, works really closely with them.
Sometimes it's in the office sitting next to their salespeople, giving their them feedback as they're on their first few calls, helping them stand up this distribution motion.
And then from there, once they've kind of 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 you're in scale mode and that's where we're trying to understand, where are they blocked?
What do they think they might be able to expand into another sub segment they serve?
If they integrate with some part of our system or we offer a new feature, things like.
Of that nature.

Omer (23:08.500)
Can you tell us a little bit about your pricing model?
I think, you know, maybe somebody listening to this 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, and your pricing, like it's, it's really dependent on your growth, is dependent on the success of your partners is right, Exactly.

Andrew Brown (23:35.230)
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 Shopify does in your, you know, partnership with them is huge to you and 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, we keep a smaller portion of that and our business grows as well.

Omer (24:15.410)
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 whole thing about going out and networking and building trust.
Looking back, what do you think?
What else was one of the biggest challenges or obstacles to hitting that first big milestone of a million in ARR?

Andrew Brown (24:44.320)
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 got to sign all the partnerships, get them live, get them launched and get them growing 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 huge things.
But there was also the idiosyncratic stuff you wouldn't expect.
Covid hitting was just a massive sideswipe for us as it was for so many businesses.
In our case, I think we were in that period in between, 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, than 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.
And not only did they survive, they didn't cut payroll, even while they might have 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 laid 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 software that deals with state forms and all those sorts of stuff, and did that really quickly as a matter of a six or eight week sprint together to help build this sort of new 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 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 going to grow our businesses side by side.

Omer (26:55.990)
You mentioned you'd been in stealth mode for a few years.
I'm curious, what was the main 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.

Andrew Brown (27:20.810)
It was 100% 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 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, 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 we were fortunate to be in a position to be able to put the pieces together to see that.
And we didn't really want to 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, very reliable way, Something you weren't gonna have to go pack together and redo at the end of the day.
And I think that served us really well.

Omer (28:17.850)
So you and I were talking earlier and I was saying that it looked like you were raising money like clockwork.
Like you launched January 2019, the January next year, you raise 8 million.
Series A, the January next year, 35 million and so on.
I'm trying to figure out, like, you know, one, you're in stealth mode.
Two, you're still building 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?

Andrew Brown (29:03.230)
The answer is the funding was crucial.
Payroll is a deeply complex state by state product and something that requires a lot of upfront investment.
There's not much of a thing of an MVP within payroll.
The IRS frankly, does not care whether you're six months old or 60 years old.
They expect you to do everything the exact same way.
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 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 for those first couple of rounds definitely went a lot 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 partners.
And then lastly 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 that's kind of what venture capitalists dream of.
And so I think we're able to attract quite a bit of attention in dollars.

Omer (30:26.710)
What does the competitive landscape look like today?
So it's 2019, so we're talking about four or five years you've been working on this business.
You looked at the incumbents back then, 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 create a better solution.
Has much changed in those last four

Andrew Brown (30:55.310)
or five years, I would say from the big guys, the big established payroll companies.
Not really is the answer.
If you go to their websites, they all have some generative AI chatbot strategy now or something or other.
But 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 really the whole category of embedded payroll that Chuck has now created and have tried to come in and compete with us, which I think is healthy and has helped frankly push the whole market forward.
But it's very much broken out where there's kind of a, I would call it a historical payroll set of incumbents and then the insurgents, of which we are the dominant one over on the other side trying to really evangelize this idea that embedded payroll is the future.

Omer (31:47.550)
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 feel that that again gave you an edge because you had a little bit of time to establish yourself in terms of being a leader in the space?

Andrew Brown (32:07.400)
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, 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.

Omer (32:21.880)
So, you know, with your story, it's a great one.
Like we talked about 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 $100 million.
You know, 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 maybe a flavor of maybe, you know, some of the, the difficulties or challenges that you've also faced.

Andrew Brown (33:03.480)
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.
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'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 a quarter, six months, a year.
I've been over, across these two companies at this.
For a decade or so.
At this point, maybe a little more.
At that point, you're talking about your life, right?
It's like, what are you dedicating it to?
And 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 between your life and your work, your passion, the company that you're building.
So more than anything else, that's what I'd say.
Not only did I go through the one acquisition which was exciting and at the same time not what I wanted, the personal side, I went through a divorce in that period, too.
So I'll give you another 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, we not only had our own business bank account, we have the account that we, on a custodial basis, were 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.
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 it was probably the worst feeling I've had, I think, in my whole career, was that Friday morning when we woke up and we saw that the funds were not in anyone's bank account.
It's hard to.
And what are you supposed to do, too?
It's hard to imagine kind of a worse situation as a founder of a payroll business.
And truly, for a minute, you're like, is this company killing?
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, managed to get every single person that was supposed to be paid through the platform, get them their money before the end of that business day.
And that took moving mountains.
It took both fast action and a ton of prep ahead of time.
So we thankfully had our corporate funds and other accounts, 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, we were able to move funds around, fall over to other banks, ultimately basically front the money and get folks paid, do the right thing by our partners.

Omer (36:17.460)
Wow, what a story.
I know many startups struggled with that situation, but your situation is unique because there were partners dependent on that money, there were people, employees and small businesses dependent on that.
And saying, well, 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.

Andrew Brown (36:45.270)
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.

Omer (37:08.370)
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 know, what you've done with this business so far has met the, the criteria that the type of business that you wanted to work on.
And, and also, what do you think the future looks like?
What is the opportunity ahead for you?

Andrew Brown (37:43.490)
Yeah, I've been reflecting on this a lot recently too, and the answer is 100%.
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.
Truly, if we raise another $500 million tomorrow, I feel like we could have 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 is really driving so much of the sector of the venture economy right now too.
And I just feel incredible, incredibly fortunate to be in that seat and have such an amazing team around me that 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 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 ecosystem of partners built on top of us and other folks who we work with who have any questions.
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.

Omer (39:02.150)
Love it.
Love it.
It's a super interesting business.
All right, let's wrap up.
Let's get onto the lightning round.
I've got seven quick fire questions for you.
You ready?

Andrew Brown (39:11.350)
Let's do it.

Omer (39:12.070)
Okay.
What's one of the best pieces of business advice you've received?

Andrew Brown (39:16.630)
When someone tells you who they are or shows you who they are, believe them.
I think business at the end is all about people, and you just got to believe who you believe, what you see.

Omer (39:26.070)
I love that.
What book would you recommend to our audience and why?

Andrew Brown (39:31.030)
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.

Omer (39:48.400)
What's one attribute or characteristic in your mind of a successful founder?

Andrew Brown (39:53.600)
Grit and determination.
I think at the end of the day, that's.
You got to have other things too, but that'll take you an awfully long way.
People underestimate hard work.

Omer (40:02.800)
Yeah.
What's your favorite personal productivity tool or habit?

Andrew Brown (40:08.720)
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.
It's all about getting through the to do list.

Omer (40:31.110)
I got to give props to Apple Notes.
I always thought of it as like this, this kind of super basic notes app.
And then I watched a 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 those features.
I don't know if that's good or bad.

Andrew Brown (40:45.760)
They like the minimalist design.

Omer (40:47.440)
Yeah.
What's a new or crazy business idea you'd love to pursue if you had the extra time?

Andrew Brown (40:52.400)
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 thing post check.
I may have to go give it another shot.

Omer (41:10.150)
What's an interesting or fun fact about you that most people don't know?

Andrew Brown (41:13.590)
I once camped out for two months in order to get into the Duke UNC basketball game.
I was a camera crazy.

Omer (41:19.950)
Two months.

Andrew Brown (41:20.790)
Two months, Yep.
Living in a tent in North Carolina.

Omer (41:23.830)
Wow.
And finally, what's one of your most important passions outside of your work?

Andrew Brown (41:29.270)
I love just getting outside.
Hiking, skiing, you know, anything that gets me into the great outdoors.
I think we spent and 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.

Omer (41:43.940)
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.
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 keep following up and see where you take this business.
If people want to 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?

Andrew Brown (42:14.990)
Yeah, just shoot me an email.
I'm andreweckhq.com I'm pretty easy to find on the interwebs.
And yeah, reach out.
I'd love to stay in touch.

Omer (42:22.510)
Awesome.
Thanks, man.
It's been a pleasure and I wish you and the team the best of success.

Andrew Brown (42:26.590)
Thanks, Omer.
Thanks for having me on.

Omer (42:28.190)
Cheers.