Jason Lee: Entrepreneur, Architect of On-Demand Pay, and the Visionary Behind Two Major Exits

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[00:00:31] All right, I want to talk to you for a moment about retaining and developing your workforce.

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[00:01:20] Hey, what is going on everybody? Ryan Leary, William Tinkup here for the Inside the C-Suite Podcast.

[00:01:27] William, how are you today?

[00:01:29] I'm doing wonderful. Thank you for asking Ryan.

[00:01:31] Oh, I would never not ask you how you're doing, unlike some people I know that do introductions and just forget I'm here.

[00:01:39] Which has happened, Jason, who is our guest today.

[00:01:44] Jason, Jason Lee, we've had Jason on recently at our show that we did live at HR Tech, who had a hilarious story to talk about, which we're not going to talk about today.

[00:01:57] But we are here to learn about Jason's journey.

[00:02:00] Jason has a very storied history of success, and I'm sure there's some challenges in there that we can all learn from.

[00:02:09] So, Jason, welcome into the show. Why don't you take a moment and just introduce yourself to the audience?

[00:02:15] Well, thanks so much, William. It's really great that you have me on this show.

[00:02:20] Where's Ryan? Oh, Ryan, sorry.

[00:02:22] That's funny. That's funny. I kind of, I thought he was going there.

[00:02:28] So well played.

[00:02:29] That's great.

[00:02:30] Oh, my God.

[00:02:31] I thought that's where he was going.

[00:02:33] I was just like this, you know.

[00:02:35] This is exactly what needed to happen. Thank you.

[00:02:38] For the listeners on this podcast, I don't know how many of you have had the opportunity to meet William and Ryan in person, but it's also a riot in person.

[00:02:48] So thanks, guys, for having me here, for having me back.

[00:02:52] We spent some great time at a trade show called HR Technology about a month ago now, but it's great to reconnect here.

[00:03:01] I'm sure we'll get into it, but yeah.

[00:03:03] So I have had or I've done a couple of things, I guess, over my career.

[00:03:07] I started in a very traditional role on working on Wall Street at an investment bank, and somehow I kind of figured out how to take the things that I had learned on Wall Street and really, frankly, bring them to All Street, which is building products that really make more sense for everyday Americans.

[00:03:29] And, you know, that entrepreneurial journey has enabled me to start companies, to exit companies, to sell companies, to restart more companies, and now to work at a company.

[00:03:41] And so I'm looking forward to spending some time with you both.

[00:03:44] So tell us about the current position.

[00:03:46] What are you doing currently?

[00:03:48] Sure.

[00:03:48] So right now I work at a company called Chime Financial.

[00:03:53] I'm the chief of something that we call Chime Enterprise.

[00:03:56] Just to maybe back up for a quick moment, for those of you who may or may not have heard of Chime Financial, Chime is a digital banking application.

[00:04:07] We were founded about 12 years ago, and, you know, the company had found sort of early success in being able to really offer a highly compelling product to everyday Americans.

[00:04:20] And that product was a zero or no, excuse me, a zero fee or a very, very low fee basic checking account.

[00:04:29] And it had a really interesting feature and product associated with that checking account, which is, hey, if you get paid on Friday, we'll help you get paid on Wednesday.

[00:04:41] You know, it was this idea that the payroll departments already sent the money.

[00:04:46] And back then it was sort of in transit.

[00:04:49] And we at Chime are going to make those funds available to you on a Wednesday.

[00:04:54] Who would have thunk that people wanted that product and they wanted to receive their pay two days early?

[00:05:01] You may obviously hear a theme here, you know, as we, you know, as we go through my journey and my involvement with the company.

[00:05:10] But that turned out to be the spark of what turned into an amazing idea set of members, a company, a franchise.

[00:05:20] It just kind of grew and grew and grew.

[00:05:23] And, you know, today we've got seven million members or users who have our card in their wallet or in their purse, walking in and out of stores every day, spending a hundred billion dollars a year.

[00:05:35] And we're really adding a tremendous value to the financial and banking system for everyday Americans, people who need this probably more so than maybe, you know, you or I on the call today.

[00:05:48] That's Chime.

[00:05:50] And, you know, and we'll probably get into this.

[00:05:53] But, you know, certainly from my perspective, what I've observed is a what I would call maybe continuing evolution or developing relationship between finance and technology.

[00:06:06] And as those two worlds evolve, it opens up these very interesting opportunities and opens up some very interesting corridors for us to go down, which really enable us to create greater access and to unlock greater financial freedom for a lot of folks who may have been left behind in the current financial and banking system.

[00:06:26] And so that's kind of what our company does at large.

[00:06:30] What I'm doing, and this will kind of get into a little bit of my background, but what I do for a living is I work with or I work rather with large employers to really be able to offer them different types of financial wellness or financial stability products.

[00:06:47] And, you know, we call this HR technology, as you guys are familiar with, or financial wellness or a suite of benefits.

[00:06:56] That's sort of what I do for a living.

[00:06:58] Earlier this year, Chime had approached me and the company, the second company that I had founded, and said, hey, you know, do you think it makes sense for us to perhaps bring some of Chime's amazing financial suite of products to companies?

[00:07:15] And to create a version of Chime's amazing, and to create a version of those products that makes sense for us to offer to employers who can then offer those things to employees as different ways in which their employees can become more financially healthy.

[00:07:28] You know, I've known the Chime folks for several years.

[00:07:32] I have an enormous amount of respect for what they've built in perfect candor.

[00:07:37] And, you know, of course, I'd be lying if I said, you know, our company that they acquired had only been around for about 14 months or so.

[00:07:46] So it's not like we were looking to do an acquisition or looking to do a sale of the company.

[00:07:52] But when we kind of put the ideas together of what this could be, just an opportunity that I felt like me and the founding team really could not turn down.

[00:08:01] And so, you know, we transacted and we joined forces with Chime earlier this summer.

[00:08:08] And here we are now really trying to build a world-class enterprise financial wellness company within Chime that is built on top of the banking products and banking infrastructure that they have spent the last 12 years building.

[00:08:25] Jason, this is a show about you, right?

[00:08:29] Your journey, your history, your entrepreneurial journey into where you are today.

[00:08:35] So let's go back a little bit.

[00:08:38] Let's go back to the beginnings.

[00:08:40] How far do we want to go back today, William?

[00:08:43] College?

[00:08:43] High school?

[00:08:44] Yeah, let's do college.

[00:08:46] College?

[00:08:46] College.

[00:08:47] I think he probably had an idea of what he wanted to do.

[00:08:49] Possibly.

[00:08:50] Well, you know, let me start by saying this, and this is actually the truth, which is I have never done.

[00:08:55] I've never done a podcast or an interview like this because, you know, I have frankly been one who has always believed the main star of the show, the main character are the end users or our employer partners.

[00:09:08] Notwithstanding the fact that, yes, I get a lot of these requests to do these types of shows, I've really never felt like it's about me.

[00:09:15] This is about something that we are building to try to move the landscape and to really unlock financial progress for truly folks who have been a little bit left behind or left on the outside of the financial and banking system.

[00:09:30] But when, you know, I just have such an enormous amount of respect for what you guys do, for your reach, for the years and years and years that you've spent in HR technology.

[00:09:42] You know, this weird, wonderful world of HR technology.

[00:09:45] Weird is correct, yeah.

[00:09:47] Weird is correct.

[00:09:47] And so I did want to make sure that I noted that because I haven't done a lot of these where I talk about myself.

[00:09:52] I know.

[00:09:53] But I did want to make sure you guys, that you all knew that.

[00:09:57] I will definitely get to college, but maybe I can start by just saying, like, I think I've always looked at the world and I've always seen the world very, very differently.

[00:10:06] You know, unfortunately, and for those of you who are on the podcast, if you are like this, you know, IYK, IYK, you know, if you know, you know, which is you look at things and you just sort of wonder to yourself,

[00:10:21] well, why is it that way?

[00:10:23] Or that ought not to be that way.

[00:10:25] Or I can't really sleep at night because I feel like the world, everyone's looking at the world like this and I'm seeing it like this.

[00:10:32] What's wrong with me?

[00:10:33] You know, it's great that we have this thing in the United States called entrepreneurism and that enables people like us and me to be able to satisfy or to find a living or discover a living if you are one of those people who looks at the world differently.

[00:10:49] Eight years old, I was in the second grade and, you know, I grew up, I have an older brother.

[00:10:55] He's very, very different than I am.

[00:10:57] He's a physician.

[00:10:58] He's married to a physician.

[00:10:59] He's an incredible dermatologist up in Boston.

[00:11:02] But we're very, very different people, you know, and I, you know, I probably tend to be a little bit more gregarious and, you know, he's a little bit more, you know, in the books.

[00:11:10] And he grew up to be a doctor.

[00:11:12] I grew up to be a, you know, technology charlatan.

[00:11:15] And so we're very, very different people.

[00:11:17] You know, I remember he was he was 11 at the time.

[00:11:20] So he was maybe in the fifth in the fourth grade or so.

[00:11:24] And he was asked by his school to go sell 30 boxes of M&M.

[00:11:31] Remember, do you remember when you had the dealers?

[00:11:33] You sold the 30 boxes of M&Ms for a dollar.

[00:11:35] You had to raise the money because he was going on a school trip.

[00:11:38] Hi there.

[00:11:39] I'm Peter Zollman.

[00:11:40] I'm a co-host of the Inside Job Boards and Recruitment Marketplaces podcast.

[00:11:45] And I'm Steven Rothberg.

[00:11:47] And I guess that makes me the other co-host.

[00:11:49] Every other week, we're joined by guests from the world's leading job sites.

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[00:12:04] And it was a sleepaway trip.

[00:12:06] It was a real trip.

[00:12:08] And he had a month to do it.

[00:12:10] And I recall it was day 29 of that 30-day month.

[00:12:14] And he had sold one box to my parents.

[00:12:18] Yes.

[00:12:19] My parents.

[00:12:20] And I remember, like, there was this, my parents were worried.

[00:12:23] He was worried.

[00:12:24] I said, you know what?

[00:12:26] Let me do it.

[00:12:27] Here I am, second grade.

[00:12:28] Let me do it.

[00:12:29] I'm going to do it.

[00:12:30] And by the way, I'm going to tell this story the way my brother told the story at my wedding.

[00:12:35] Okay.

[00:12:36] So I saw Jason.

[00:12:37] Was he the best man at your wedding?

[00:12:38] He was, yeah.

[00:12:39] So he's like, I saw Jason.

[00:12:41] And he said, I'll do it.

[00:12:42] I said, okay, well, you can try.

[00:12:44] But, you know, I didn't want to sell these M&Ms.

[00:12:46] And so, anyways, the way he tells the story is he goes away.

[00:12:51] He went to his friend's house or something.

[00:12:53] He gets back in about an hour.

[00:12:55] And he sees me on the sofa eating M&Ms.

[00:12:59] And he says, what did you, you can't eat the M&Ms.

[00:13:05] I had to sell those for school.

[00:13:06] I mean, and he was completely freaking out.

[00:13:09] And I said, just wait.

[00:13:11] Here's the $29.

[00:13:13] And I said, I went around the neighborhood and I sold those for $2 a piece.

[00:13:18] And I took the money myself and went to 7-Eleven down the street and I bought my own M&Ms.

[00:13:23] Okay.

[00:13:24] And so, and I said, and he tells that story.

[00:13:28] And he told that story to basically say, like, even at that age, I knew that Jason saw the world very, very differently.

[00:13:34] And the thing that I had, the difference in the way that I had seen the world was this ain't about M&Ms.

[00:13:43] It's about someone else's willingness to make an investment in something that you are trying, that one is trying to do.

[00:13:49] It has nothing to do with one's desire to go buy M&Ms.

[00:13:53] This was about, can one convince and persuade someone else that this was a worthy cause?

[00:13:59] And if so, they should be willing to pay any price to go fund that cause.

[00:14:04] And so, I tell that story early on to say, like, you know, and, you know, look, I'm, you're, you're, if anyone's watching this on, on the video or if you're hearing it, you'll see that, or if you're seeing it rather, you'll see that I'm Asian American.

[00:14:20] And so my, you know, I grew up sort of in a very traditional household where, you know, folks were saying, my folks were saying, please do one of the following two things.

[00:14:30] You know, be, you know, be a doctor or be a lawyer, right?

[00:14:34] Like, one of two things.

[00:14:36] And, um.

[00:14:37] That's pretty options.

[00:14:38] That was really the only option.

[00:14:39] Because, you know, when you come to this country, the thing they tell you is that, well, professional licensure is very important.

[00:14:44] And those are things that, you know, people really can't take away from you.

[00:14:47] And so having some type of professional license is, um, it's a sure way to.

[00:14:53] But finance is a close third.

[00:14:55] Well, so what's interesting is no one, no one knew about that.

[00:14:59] Back when I was, um, in college, I came home.

[00:15:02] I said, look, I don't want to do, um, medicine or, um, or, or law.

[00:15:09] I'd like to do this third thing.

[00:15:10] You know, I want to go to Wall Street.

[00:15:11] And why I wanted to do that is because I felt like there was something that I had, um, which was I had this unique ability to understand very, very complicated things.

[00:15:25] But to be able to abstract that complexity away to really kind of get at the heart of either the product or the investment or the security or whatever transaction that we were doing.

[00:15:38] So I relish in complexity.

[00:15:42] But what I relish more in is the ability to abstract that complexity to create a very simple result for whomever that end user might be.

[00:15:49] And, and, and that was what I went into out of, uh, of undergrad.

[00:15:54] I went to undergrad in Philadelphia at the University of Pennsylvania.

[00:15:58] And, um, and what I discovered was there was this entire world up here in New York, which is where I am now, um, called Wall Street, where you could go have a really great career by knowing something highly esoteric.

[00:16:16] Yep.

[00:16:17] And repeating it a million times a year.

[00:16:20] And what I did was I went to Wall Street and, and, you know, it's funny.

[00:16:25] I thought I would fit in there.

[00:16:26] Frankly, I didn't really fit in there because even within a large investment bank, even when I had the opportunity to go create lots of really, like, highly esoteric, um, securities.

[00:16:39] And, and, and I worked on something called derivatives.

[00:16:43] Oh, yeah.

[00:16:43] Structured credit and all these structured finance.

[00:16:46] And I was probably doing, you know, one of the most complicated things on the street.

[00:16:52] I still felt like, you know, I still see the world very differently than the rest of my colleagues, uh, on Wall Street.

[00:17:00] One of the things that I learned, though, in building structured products is that not everyone wants them.

[00:17:09] And these are very, very tailored solutions.

[00:17:12] They're very difficult to get someone to do.

[00:17:16] Once you do them, well, then they're very profitable or whatever for the bank.

[00:17:20] But really, the thing that I learned in that entire experience was the ability to never give up trying to find a way to get the sofa through the front door.

[00:17:31] And we can call that sales skills or whatever.

[00:17:35] But, but really it's around how do we position this product even though the buyer, even though the client doesn't know they want it.

[00:17:44] How do we sort of like change this or position this or do this or create a piece of content that does this?

[00:17:52] And I mean, all of these things which enabled us to be able to get these like really weird products sold.

[00:18:01] I started a group, um, on Wall Street that was building these products.

[00:18:06] It's now become a multi-gajillion dollar industry where we took products that were highly bespoke, highly tailored.

[00:18:13] And because we were able to get so many people to do them, they became mainstream almost.

[00:18:19] Um, and that to me was super exciting, but that was like Wall Street, you know, and, and, um, you know, you're dealing with wholesale businesses, wholesale clients.

[00:18:30] Um, you know, and those are great things.

[00:18:33] You're a shame on me.

[00:18:34] Here I was in New York living sort of the life where one would never have thought of, um, the idea of, um, gosh, you know,

[00:18:43] is there a way to kind of take all of that learning and actually to kind of convert it and to almost transform it into something that is more accessible and more scalable through web technology to what I call all street, you know, from Wall Street to all street.

[00:19:01] One of the things that I did at, uh, on Wall Street was, um, I really specialized in this idea of like moving money around, um, to create different outcomes.

[00:19:14] And that's a very like high level way of thinking about what it is that we're doing.

[00:19:19] There's a word for that on Wall Street called derivatives, which basically means they're, they're contracts that we use that replicate or that create the payout of if you actually move the money itself.

[00:19:31] So it's a lot of like abstraction, a lot of synthetic arrangements, et cetera.

[00:19:35] What's very interesting about that background is it enabled me to then observe and to spot a really critical flaw in today's payroll system.

[00:19:47] And that flaw was, Hey, we are working today and every day we earn money, but that money is never really materialized until payday.

[00:19:59] It takes someone in Indiana in the payroll department to hit a few buttons to go, you know, hit a thing.

[00:20:06] And then that money sort of, you know, exits the company, the employer and hits the employee's bank account.

[00:20:11] I looked at that and I said, I wonder if there's a better way for us to use financial engineering scaled through web engineering to kind of create a very, very different result for that end employee.

[00:20:27] Um, and, and the basic concept that I, that we really started with, um, and I'll, and I'll give you some of the journey here, but the basic concept that we started with at, at daily pay was really the following, which is every day you work, the data that represents that you worked, it actually lives at the employer.

[00:20:47] Like that data exists in the employer's systems.

[00:20:51] The problem is it exists in highly unconstructed format, meaning the hours that you work, well, that exists, you know, on site at the time clock or, or whatever it might be.

[00:21:03] The, the TNA, the time and attendance system, the fact that you live in Indiana, well, that's trapped in the HRS or the central database, your payroll dates and all that, that's in the payroll system.

[00:21:14] So, and the money itself is actually at the company's bank account.

[00:21:18] So all of these things, they exist.

[00:21:21] The analogy I always give, I got a seven-year-old son and he's very into Legos.

[00:21:27] And if you open up one of his Ziploc bags, you will see all these disparate pieces of Lego, white piece, brown piece, a wheel, a steering wheel.

[00:21:36] Like, it's all jumbled up.

[00:21:38] But I can guarantee you and promise you that in that bag is a police car.

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[00:21:59] Whether you're in healthcare, transportation, or finance, our continuous monitoring ensures you have real-time data you need to respond to risk immediately.

[00:22:08] Protect your organization with SISIV's continuous criminal monitoring because workplace safety doesn't stop after hiring.

[00:22:18] You know what you should know?

[00:22:20] You should know the You Should Know podcast.

[00:22:23] That's what you should know.

[00:22:25] Because then you'd be in the know on all things that are timely and topical.

[00:22:29] Subscribe to the You Should Know podcast.

[00:22:32] Thanks.

[00:22:33] Or a fire truck.

[00:22:35] Or a Star Wars jet.

[00:22:37] You don't have to add a piece.

[00:22:38] You don't have to subtract a piece.

[00:22:39] All of the pieces are right there.

[00:22:41] But someone needs to construct it into the thing.

[00:22:46] And that's kind of what we did.

[00:22:48] We built a big computer that said all of the data is already there.

[00:22:52] Someone just needs to construct that data and create interoperability across all of the different systems that are out there.

[00:22:59] Cronus, ADP, Workday.

[00:23:02] And so we built this big machine that created all of this interoperability around all the data points to say we now know you have earned $84 as of today.

[00:23:14] We then did a bunch of Wall Street stuff that attached money to it.

[00:23:18] And then we provisioned an app and said whenever you want you can get this money.

[00:23:24] And that was really the birth of on-demand pay.

[00:23:28] And that's kind of how we thought about it.

[00:23:30] Now, it doesn't always work the way you think it will.

[00:23:33] Here are the challenges.

[00:23:35] Yeah, I'll tell you how I started the company.

[00:23:37] And I think this is probably more of what your listeners are more interested in, sort of the travails of starting a company like this.

[00:23:46] It is November of 2015.

[00:23:48] Imagine this.

[00:23:49] I'd like to go raise some venture capital.

[00:23:53] And, well, 98% of the venture capitalists I spoke to said, I don't understand.

[00:23:59] Why do people need access to their money?

[00:24:01] I don't need access to money.

[00:24:02] I have a lot of money.

[00:24:04] Of course you don't.

[00:24:06] Yeah.

[00:24:07] My favorite – so that's like 98%.

[00:24:10] So there's no product for this.

[00:24:11] There's no market for this.

[00:24:13] Yeah.

[00:24:13] There's no market for it.

[00:24:14] I don't – why would anyone pay for their money?

[00:24:17] Well, you don't understand.

[00:24:19] You see people are paying these overdrafts.

[00:24:20] My bank doesn't do overdraft.

[00:24:22] They waive those fees.

[00:24:24] It's going to get $15 million in the account.

[00:24:26] That's right.

[00:24:27] Yeah.

[00:24:28] It's in their best interest to waive those fees.

[00:24:30] Now, to be fair, 2% sort of said, okay, I'll take a phone call.

[00:24:35] A lot of no's.

[00:24:36] A lot of rejection.

[00:24:37] Right.

[00:24:38] 2% said, okay, I'll take a phone call.

[00:24:41] One of the guys came back and said, well, look, I thought this was a good idea.

[00:24:45] But I got in the backseat of my Uber, and I asked him.

[00:24:49] I said, do you need your money?

[00:24:51] Are you struggling right now?

[00:24:53] And the Uber driver told me he's fine.

[00:24:55] That's great research.

[00:24:57] And this guy was –

[00:24:58] David, sir, won.

[00:24:59] Good.

[00:25:00] Venture Capital.

[00:25:01] They have these funny lists.

[00:25:03] I think one of them is like the Midas list.

[00:25:06] Oh, yeah.

[00:25:06] Like everything you touch is gold.

[00:25:08] I mean – and so – and he was on that list.

[00:25:12] And I said, that's your research?

[00:25:13] I said, like, do you think that that immigrant is going to tell you the truth while he's driving you around?

[00:25:21] There's 100% no chance he's going to ever tell you the truth.

[00:25:24] And – but that – so those guys passed.

[00:25:27] I had one brave soul who said, you know what, we'll write a check.

[00:25:31] So first million dollars in.

[00:25:33] Eventually, we raised over $250 million of equity when I was there at the company.

[00:25:37] But that was sort of what – that was kind of the start of the company.

[00:25:41] Now, we had to prove that this thing actually worked.

[00:25:48] Right.

[00:25:48] And, you know, like all technologists, you have to get your first clients on.

[00:25:53] Well, I'm an enterprise person.

[00:25:55] I always knew that we would be doing this with employers, with companies, et cetera.

[00:26:01] But as you guys probably know, when you build something in payroll or with money, the bar is very, very high.

[00:26:10] It's extremely high.

[00:26:11] Can't make mistakes.

[00:26:12] And you can't make mistakes.

[00:26:13] Yeah.

[00:26:14] So I looked at this and I said, no.

[00:26:16] It's going to take us nine months to go find our first client.

[00:26:20] I don't have any cousins.

[00:26:22] No one owns a dry cleaner or a deli.

[00:26:25] I can't ask anyone for a favor, okay?

[00:26:27] I said, and if we found someone, they'd fire us because we're just getting started.

[00:26:33] Where do I find a bunch of people who all work for the same company who have a monolithic payroll time and attendance system where I don't need the employer's approval?

[00:26:45] And that led me to Uber drivers.

[00:26:48] I said, all of those drivers use the same system.

[00:26:51] Now, this is probably getting in a little trouble, but at this point, I'm like retired.

[00:26:55] Yeah, you're bad.

[00:26:57] That's your limitation.

[00:26:58] You know, I said, look.

[00:26:59] So my partner and I, my technology partner and I said, look, let's build an app that looks like the Uber driver app.

[00:27:07] Right.

[00:27:08] Okay?

[00:27:08] So it looked like the Uber driver app.

[00:27:12] And we said, log in.

[00:27:14] I feel like it's a documentary about that.

[00:27:15] We said, log in with your credentials.

[00:27:17] We said, log in with your Uber credentials and we'll pay you.

[00:27:21] And so what we were doing in my basement was we were taking those credentials and logging in on their behalf and seeing how much they had made.

[00:27:29] And then we would get that balance.

[00:27:31] We'd export it into our app and said, you're eligible to, you know, to receive whatever, 300 bucks because you've driven that much.

[00:27:39] Press a button.

[00:27:39] And that's how we did it.

[00:27:41] And so that's how we started to test the system.

[00:27:44] And we started testing it, seeing what the product market fit was.

[00:27:48] Right?

[00:27:49] It's all easy.

[00:27:51] Except for the fact that when we built it, we tested it with one driver.

[00:27:56] We were ready to go.

[00:27:58] Ready to go.

[00:27:59] We had our driver.

[00:28:00] He was in my basement.

[00:28:01] We're moving them.

[00:28:02] We're ready to go.

[00:28:03] Let's go sign up some drivers.

[00:28:05] It's going to be easy.

[00:28:14] Go to the subway, get out to JFK Airport, go to their big parking lot where they're all stationed waiting for the pickups.

[00:28:21] Start knocking on windows.

[00:28:23] It's the middle of January.

[00:28:24] Knock on windows.

[00:28:25] Hey, how are you?

[00:28:26] I'm Jason.

[00:28:27] Uber pays you every Thursday.

[00:28:29] Do you want to get paid whenever you want?

[00:28:31] No.

[00:28:32] I don't need it.

[00:28:34] No.

[00:28:34] First day.

[00:28:34] You're like the New York salesman that opens up his jacket with the watches.

[00:28:38] Yeah.

[00:28:39] First day.

[00:28:40] Probably talk to 100 people.

[00:28:42] No one signs up.

[00:28:43] Zero sign ups.

[00:28:44] Go home.

[00:28:44] Go back the next day.

[00:28:46] Zero sign ups.

[00:28:47] Go home.

[00:28:48] Go back the next day.

[00:28:50] Zero sign ups.

[00:28:51] Three full days.

[00:28:52] Zero sign ups.

[00:28:53] And it's getting, it's dark.

[00:28:55] Oh, yeah.

[00:28:56] I'm like, it's freezing.

[00:28:57] And I'm like, did I get this thing wrong?

[00:29:00] And I called my partner and I said, I don't know.

[00:29:06] This should be working.

[00:29:07] I don't know if we got this wrong or not.

[00:29:10] And as I'm walking out of the parking lot and Nigerian driver, he's a kid, he's 24 years

[00:29:15] old, stops me.

[00:29:16] He said, oh, what are you doing?

[00:29:18] And he said, oh, I explained it to him.

[00:29:20] He said, oh, I'll sign up.

[00:29:21] I'm like, thanks.

[00:29:23] Son of one driver.

[00:29:25] Yes.

[00:29:25] Next day online in our database, 25 people signed up.

[00:29:30] Next day after that, 100 people signed up.

[00:29:33] Fact.

[00:29:34] And he knew people.

[00:29:35] Next day after that, 300 people signed up.

[00:29:38] And so we, you know, go to patient zero.

[00:29:43] It is that Nigerian driver.

[00:29:44] I found out his phone number, called him up.

[00:29:47] And I said, I'd like to know what you did to get these people to sign up.

[00:29:52] And he said, oh, I just posted about you guys in a Nigerian Uber driver Facebook group.

[00:29:58] There you go.

[00:29:58] And in that moment, I realized, in that moment, I said, we have it.

[00:30:02] You see me going door to door, that's like a direct to consumer marketing.

[00:30:07] Right.

[00:30:07] And the fundamental issue is one of trust.

[00:30:11] They, the driver does not trust me.

[00:30:13] And that's the barrier to entry.

[00:30:15] However, the Facebook group is an abstraction for a trusted environment.

[00:30:22] You know?

[00:30:23] And now I know, if we do this through the employer, it's going to work.

[00:30:29] Because the employer represents a trusted environment.

[00:30:33] Just as a side note, for your listeners, I would tell you, the key to entrepreneurship

[00:30:37] is being able to read the signal and to create the abstraction.

[00:30:41] You see, the key to being a great entrepreneur is the ability to say, that's happening over

[00:30:48] there.

[00:30:48] But if I pull on this thread and I extrapolate, this is what the market's actually saying.

[00:30:55] Like, this was not about, is Facebook a good channel or should it be Instagram?

[00:30:59] This was about trust.

[00:31:01] Trust is the, is trust an element in being able to sell a product like this.

[00:31:07] And in that moment I said, we got it.

[00:31:11] This is going to work.

[00:31:12] And sure enough, I knew it.

[00:31:14] We let the Uber experiment run for another three months or so.

[00:31:18] 25,000 people signed up.

[00:31:19] And very, very proudly, I got my first cease and desist letter from no other than Uber

[00:31:27] itself.

[00:31:29] Yes, of course.

[00:31:30] Send me the letter.

[00:31:31] It comes in, you know, it comes in the green envelope, you know, the certified bail thing.

[00:31:36] Long, long legal letter.

[00:31:39] And I read it.

[00:31:40] A lot of fiery language in there.

[00:31:42] And you're taking driver logins and all these things.

[00:31:46] You stop immediately.

[00:31:47] Immediately took that letter and I said, we're ready.

[00:31:51] My partner said, for what?

[00:31:53] To go raise the next round of funding.

[00:31:55] That's right.

[00:31:56] Because what this is telling me is Uber's going to launch their own product, number one.

[00:32:01] Number two, their $10 billion capital raised.

[00:32:04] We've got a million.

[00:32:05] And they took the time to do this.

[00:32:07] We have something.

[00:32:09] Yeah.

[00:32:09] We have something.

[00:32:10] That's when you know.

[00:32:12] And I said, that's when I knew.

[00:32:13] Quick question, going back to Wall Street and leaving Wall Street.

[00:32:18] Were you married at the time?

[00:32:19] I was, yeah.

[00:32:20] Therein lies the question that I think Ryan and I would love to know.

[00:32:24] I'm assuming you were making pretty good money.

[00:32:26] Just going to assume most of my friends that went to Wall Street after business school did

[00:32:31] pretty well.

[00:32:32] Okay.

[00:32:32] So let's just assume that you were doing well.

[00:32:35] How did you talk your wife?

[00:32:37] How did you convince your wife that you were then going to go build a business?

[00:32:42] Well, number one, thankfully, she's very, very supportive.

[00:32:45] Number two, thankfully, she actually also worked on the street, which was also, you know,

[00:32:52] which really did help.

[00:32:54] Yeah.

[00:32:55] And then number three, I didn't have a choice.

[00:32:56] Like I was sort of leaving the bank at that time.

[00:32:59] And, you know, I was kind of looking for other opportunities.

[00:33:02] And I said, you know what?

[00:33:03] It's time to kind of go build something from scratch.

[00:33:08] This complex finance talk is very nice.

[00:33:11] Do I get my depot ever done?

[00:33:13] But you already have a depot.

[00:33:15] Eh, no.

[00:33:16] Yes, you have the Vodafone Gigadepot.

[00:33:18] Ah, right.

[00:33:19] And I have myself in the hand, how big my depot is.

[00:33:22] Now with the Vodafone Gigadepot and the data volume in the next month with me.

[00:33:27] Go on in the 5G-Netz of Vodafone.

[00:33:30] Vodafone.

[00:33:30] Together we can.

[00:33:34] The second question I have.

[00:33:36] When you did your second round of funding, did you go back to any of the people that said no to you?

[00:33:41] No.

[00:33:42] Because, you know, a lot of this is like once people say no, they're kind of out.

[00:33:46] Yeah.

[00:33:46] And they will never say yes.

[00:33:49] Right.

[00:33:49] People don't realize that.

[00:33:50] But there's too much pride.

[00:33:52] Right.

[00:33:53] They can't admit that you were wrong.

[00:33:55] Yeah.

[00:33:55] And so we, you know, people bought our stock at pennies on the dollar.

[00:34:00] And, you know, when I exited, that was in, you know, like the 20s.

[00:34:03] And so, like, we made people a lot of, we made folks a lot, a lot of value, which was great.

[00:34:10] And so we're happy that early supporters got rewarded for the risk that they took.

[00:34:15] Yeah.

[00:34:15] So, Jason, let's talk about, I always go get into mentorship and training and learning and things like that.

[00:34:24] And curious to get your thoughts on this.

[00:34:26] So as you're going through this journey, right, you're building daily pay at the moment.

[00:34:34] Was this just a you thing and your partner?

[00:34:36] Or did you have somebody there as your trusted inner circle that you would lean on to get advice?

[00:34:43] Or was this just kind of like, we're going to do it our way and we're going to try it?

[00:34:48] Well, look, what's great is that, like, I had a great partner.

[00:34:52] You know, while his specialty was more technology and mine was more business, I think we really complemented one another.

[00:35:01] And that really enabled us to really kind of test our judgments and to test our convictions with each other.

[00:35:09] I would say that was probably the most influential relationship.

[00:35:14] In part because also from a temperament standpoint, you know, he's fairly, you know, I'm fairly passionate and he's fairly dispassionate.

[00:35:21] And I think that was a good, you know, that was also a very, very good balance.

[00:35:26] Right.

[00:35:27] So the decision to leave daily pay, so daily pay for the audience industry leader and what they did, you got to a certain point and you wanted to do something new.

[00:35:41] You wanted to do salt labs.

[00:35:43] You wanted to do something new.

[00:35:46] How did that come about?

[00:35:47] Like, because here you are on this rocket ship.

[00:35:50] And I can imagine everyone's thinking you're crazy.

[00:35:52] So at different points, okay, you went to Penn, crazy.

[00:35:56] You left Penn, went to Wall Street, crazy.

[00:35:59] You left Wall Street to then start a business, crazy.

[00:36:03] The business is taking off, like killing it.

[00:36:07] You decide to then start another company, crazy.

[00:36:10] So at different points, again, people are looking at you and going, what do you, I mean, it turned out really well, Sean.

[00:36:17] But it's almost like you trust yourself to make a decision.

[00:36:20] Look, I think there's like three things that are probably going on at the same time.

[00:36:24] And it's a triangulation around these things.

[00:36:28] Number one, it's what is one's view of the project that one is working on today and how can one be most useful there?

[00:36:38] Second is market timing.

[00:36:39] You know, and like as a student of markets, I think market timing is something that you have to be very, very, that one has to be very, very mindful of.

[00:36:49] It's crazy for one not to think that way.

[00:36:52] And frankly, it's fairly arrogant to believe that your views are, you know, like I grew up in a place where I said, you know, I grew up on Wall Street at a particular culture where folks, where we believed nobody is smarter than the market.

[00:37:07] And the market is going to deem what it wants to do regardless of what you want to do.

[00:37:13] And you can either decide to get run over by the market and protest or you decide to get ahead of it.

[00:37:19] And so I think, you know, as it relates to those two things in particular, you know, and I want to be careful with what, be careful with the way I characterize this.

[00:37:30] But I think that, I don't think it's that, I don't think it's that difficult to make an assessment that technology companies, you know, at large probably have become a little bit less valuable just given the change in the interest rate environment that we are in.

[00:37:49] I mean, and that is just mathematics.

[00:37:51] That's not directed towards one particular company versus another company.

[00:37:56] It's just mathematics would dictate that in a higher interest rate environment, if one has less cash, you know, in the value of a company, well, then that will be worth less than one that is being valued in a lower interest rate environment.

[00:38:15] And that's just, you know, finance 101.

[00:38:18] And so I'd be lying if I didn't say that I am a very astute student of markets and notwithstanding the fact that I'm a deep believer in what all of my companies have built, one also has to kind of transition that ownership to people who are more equipped to operate a company in that environment.

[00:38:39] The people that my partner and I transitioned our ownership to, they are very used to operating within a lower growth or a slower growth, higher cash output environment.

[00:38:54] That's kind of what they do for a living.

[00:38:56] Right.

[00:38:58] And we were kind of all too happy to say, great, you guys take it.

[00:39:04] And, you know, we've kind of built something great here.

[00:39:06] I think our legacy is probably tied more deeply to the creation of on-demand pay and earned wage access than it is to any one particular provider.

[00:39:15] You know, candidly, like I spend a lot of my time now globally, you know, I'm on the boards of board advisor to the largest on-demand pay provider in Europe, the largest on-demand pay provider in Latin America, and the largest on-demand pay provider in Asia.

[00:39:32] And so I feel like our legacy and our involvement has sort of spanned beyond a particular company, but more to the fact that we want everybody, by the way, regardless of who the provider is, we want everyone to be able to access this life-changing benefit whenever they want.

[00:39:48] And, you know, for my seat, the tide has really been lifted because now more people have it.

[00:39:54] And so that's a little bit, but, you know, all of that to say, one also has to be a realist.

[00:40:01] And here's kind of where having a little bit of dispassion is actually very helpful.

[00:40:05] You know, you have to be able to say, you know what, and be able to walk away and say, okay, I'm not.

[00:40:11] Okay, the environment's changed.

[00:40:15] And there's a lot more that we can do.

[00:40:17] I also, by the way, just have a fundamental rule, and this is an operating rule, and you'll see it.

[00:40:22] If you ever came to my office, you would see it hung up on the door or above my door, which is,

[00:40:27] I should only do the things that only I can do.

[00:40:30] And what I mean by that is I should only do the things that only I can do because I'm very confident that there are only things that I can do.

[00:40:39] If I'm doing something that someone else can do, then I got the wrong job right now because I believe that there are only things.

[00:40:47] I'm the only one who could have walked around the neighborhood and sold a box of M&Ms for $2 when every other kid in that school is selling that box for $1.

[00:40:57] So you bet, Dennis, I'm going to sell those M&Ms for you and enjoy the peanuts myself because I'm the only one who can go do that.

[00:41:04] And I think it's important to really be very self-aware in terms of what are the things that only I can do in this world.

[00:41:13] And frankly, running a mature company, there are other people who can do that, other investors who can do that.

[00:41:20] But I think there are only a few people on the earth who can then do it again, restart salt, and then sell that, and then now try to build a bigger –

[00:41:28] I think there are only very few people who can do that, and that's really where I need to be spending my time.

[00:41:34] What advice do you give to someone that's in that predicament now?

[00:41:38] They're unable to make that decision internally to themselves to say, it's time.

[00:41:46] It's time to hand it over.

[00:41:48] I think we hear that a lot from listeners of this show in particular.

[00:41:52] In fact, it's really rare for someone to take it from zero to 100 million in HR tech in the world that we live in.

[00:42:00] I can think of two people that have done it.

[00:42:03] So, I mean, it's a short list.

[00:42:05] Go ahead, Ron.

[00:42:06] Sorry.

[00:42:06] Yeah.

[00:42:07] What's the advice you give to that person to say, this is how you make the decision.

[00:42:12] It's okay.

[00:42:13] Look, some of this is mom and apple pie and aphorisms, but I love my mother, and unfortunately, I eat too much apple pie.

[00:42:19] Anyway, these are some aphorisms, but this is really what I do tell people.

[00:42:27] Number one, and it's subjective, and I can only speak for myself, but this is what I've learned.

[00:42:34] Number one, it don't matter who you are, it always ends badly.

[00:42:38] It always ends badly.

[00:42:39] Always.

[00:42:40] Always.

[00:42:51] I live out here in New York.

[00:42:53] You think that Aaron Rodgers is really, does he really think he made the right decision here in trying to play out his last two years in New York, getting booed by these ruthless Jets fans?

[00:43:05] No.

[00:43:06] No, he doesn't think that.

[00:43:07] Probably not.

[00:43:07] It always ends badly.

[00:43:09] Absolutely.

[00:43:09] And I think you have to acknowledge that.

[00:43:12] Right.

[00:43:13] You have to acknowledge that things, it's not just about you.

[00:43:18] You have to have enough of a humility to understand that there are 85 other things that are going on in the world that will make what you want to do not happen.

[00:43:29] Right.

[00:43:29] Like, every day at Daily Pay, I always thought to myself, I'm on a timeline.

[00:43:34] Not that I'm trying to, like, get something done, but rather, I'm on borrowed time.

[00:43:37] Right.

[00:43:38] Every day I thought to myself, I'm on borrowed time.

[00:43:41] I'm on borrowed time.

[00:43:42] Why?

[00:43:42] Not because I thought that there was the boogeyman at some point, but because I know that's the way the world is.

[00:43:47] There's competition.

[00:43:49] There's regulation.

[00:43:49] There's people trying to kill you from the inside, from the outside.

[00:43:52] Every one of us, if you're in that spot, you're on borrowed time.

[00:43:56] And not all of us are alike.

[00:43:59] The president, like, what's great about politics is that there is fixed term.

[00:44:03] And you know when to end because it's a discrete date.

[00:44:06] Right.

[00:44:06] This is harder.

[00:44:07] But you have to have the discipline and the self-awareness and the humility to understand that you're not that great.

[00:44:14] You're on borrowed time.

[00:44:15] And nobody knows who the CEO of Xerox was 20 years ago.

[00:44:22] No.

[00:44:22] Right.

[00:44:22] But yeah, that was the best performing stock in the Dow.

[00:44:26] But nobody knows.

[00:44:28] Last question for me, and it's just because I know people are going to be interested.

[00:44:31] You're a technical partner from Daily Pay.

[00:44:36] What did he go on to do?

[00:44:39] So he is still my partner.

[00:44:40] So we worked.

[00:44:41] We founded Salt Labs.

[00:44:43] We are now.

[00:44:43] You got the band back together.

[00:44:44] We now work.

[00:44:45] We now work a time together.

[00:44:46] So he's here with me.

[00:44:47] And, you know, we already have, you know, we're always talking about the other, the next one or two things that we'll probably build after this.

[00:44:56] Of course.

[00:44:58] Sorry, Ryan.

[00:44:59] Let me just add one more thing to what you said, which is number one, it always ends badly.

[00:45:03] But also number two, this is my deep view.

[00:45:06] You never regret selling.

[00:45:07] And I don't mean selling just stocks.

[00:45:10] I mean you never regret making a decision.

[00:45:13] Because if you're that person who's always looking back, then you shouldn't even be on this podcast.

[00:45:18] We only want people who are on this podcast who are listening to this podcast who don't look back.

[00:45:24] Yeah.

[00:45:24] And I think that's probably the biggest, just talking to people.

[00:45:29] That's the biggest argument in their own mind.

[00:45:33] They're just afraid to make that mistake.

[00:45:36] Ryan, we see it with athletes all the time.

[00:45:38] Yeah.

[00:45:39] Or, you know, people that stay just one season longer than they should have.

[00:45:43] Aaron Rodgers.

[00:45:44] Or in boxing, one match longer than they should have.

[00:45:47] Mike Tyson.

[00:45:49] No, he's going to kill Jake Paul.

[00:45:53] So, Jason, this has been fantastic.

[00:45:55] You know, we spent a lot of time with you at HR Tech.

[00:45:58] Absolutely love you.

[00:45:59] Love what you built and are building with Chime Enterprise.

[00:46:04] Thank you so much for carving out time for us in the podcast.

[00:46:08] You guys are great.

[00:46:09] Thank you so much for having me.

[00:46:10] As I said, this is the first time I've ever done one about myself.

[00:46:13] And I had a blast.

[00:46:15] Now you can send it to your brother, your mom.

[00:46:17] Yeah, exactly.

[00:46:19] Thank you both.

[00:46:20] All right, buddy.

[00:46:20] Appreciate you.

[00:46:21] Appreciate you.