Podcast: One on one with Wagestream CTO Portman Wills

In this episode of Fintech Thought Leaders, QED's Head of Early Stage Investments Bill Cilluffo speaks with Wagestream CTO and co-founder Portman Wills.

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Show Notes

Tune in to learn:

[1:07] An introduction to Wagestream, a super-app for frontline workers.

[2:28] How Portman thinks about his North Star -- the concept of a social enterprise business that helps those who are less fortunate but still pursues a profit.

[6:10] How moving schools 14 times in 12 years helped shaped Portman’s independence and resilience.

[14:02] The Wagestream origin story – the moment Portman and his co-founder learned about the concept of earned-wage access and why they knew it was a problem they wanted to tackle.

[20:36] Why Portman’s trip to Notting Hill in 2017 framed his perception of how people change their social calendars based on their pay schedule.

[23:07] Validating Wagestream’s theory that workers would want to be paid on their schedule – at hundreds of restaurants, ice cream trucks and boutiques in the shadow of Windsor Castle.

[27:00] Getting unexpected market research by cold-calling the UK government directly.

[30:42] Forks in the road – the one thing Portman got 100 percent correct from Day 1.

[33:46] Over-indexing on how popular their product would be at launch. Just because it is a no-brainer, it doesn’t mean every B2B enterprise company will want to sign on the dotted line right away.

[37:49] The ability to take complex problems and distill them down to the one core question. The importance of solving complexity by minimizing inputs.

[41:18] Get comfortable with failure. The entrepreneurship journey is never easy and never linear. Get knocked off the horse, get back on.

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Bios

Bill Cilluffo joined QED as a Special Advisor in the fall of 2014 and became a Partner in 2015. He is currently Head of Early Stage Investments after six years as Head of International, leading QED’s Investment teams in Latin America, Europe and Asia.

Prior to joining QED, Bill spent nearly 20 years at Capital One, spanning several roles and leading several businesses. He spent the first 6 years of his career leading Marketing, product development and credit policy for Capital One’s subprime credit card business; ultimately having overall P&L responsibility, and growing the business to become the most significant player in the market. He moved on to spend 2 years in various new business development roles, spanning the telecom, medical finance and small business finance industries. Bill spent 3 years as Deputy Chief Credit Officer for the bank, playing nearly every role there was to play in the central credit function, after helping build the department from scratch in 2002.

Bill then pivoted his career to general management, leading Capital One’s Canadian, and ultimately International businesses, over the course of 6 years. Profitability of the business grew significantly under Bill’s leadership, through new product and channel introductions, acquisitions, and significant cost take out. During Bill’s last 3 years at Capital One, he led its Co-Brand and Private Label credit card business, building the business nearly from scratch to one of the top few players in the US market, through a series of acquisitions, most notably including leading the acquisition and post-merger integration of HSBC’s US credit card business, which closed in May 2012.

Bill graduated with a BA in economics from the University of Michigan, and competed the SEP program at Stanford GSB.

Portman Wills is CTO and co-founder of Wagestream. In his role he oversees all product and engineering teams across the business, globally - including oversight of the future product roadmap and ensuring the business has the technology required to serve a scaling customer base.

Portman is a serial entrepreneur, and he founded and exited multiple technology businesses, before Wagestream: SocialCash (acquired by LifeStreet media in 2009), Join the Company (acquired by GSN in 2011) and Sports Illustrated Play (acquired by NBC/Comcast in 2017). He also served as the Chief Architect at Voxiva, where he designed global communications and information systems for developing nations, and CTO of Digital Divide Data, where he architected a system for synchronous data entry in multiple worldwide offices.

Portman holds a BA in mathematics, economics, and computer science from the University of Virginia.

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Full Transcript

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Bill Cilluffo:

Hello, and welcome to the Fintech Thought Leaders Podcast. I'm Bill Cilluffo and I'm the head of early stage investments at QED investors. Today I am excited to be joined by good friend Portman Wills, the co-founder and CTO of Wagestream in London, a financial super app for frontline workers. Portman, welcome to the podcast.

Portman Wills:

Thank you, Bill. It's so official. I love it.

Bill Cilluffo:

Hey, we try to be very professional here at QED.

Portman Wills:

Yeah.

Bill Cilluffo:

And for those not familiar with Wagestream, can you share a little bit about what the company does?

Portman Wills:

Yeah, sure. So we call ourselves a super app for frontline workers, which means essentially we partner with large employers in the primarily retail, healthcare and hospitality space. So think if you have 10,000 or more employees, so a big hospital system, a big retailer, a big restaurant group, we partner with them and we provide this financial super app for their frontline workers that gives them everything from coaching to an easy way to save money from their paychecks. The thing we're most famous for is you can choose when you want to get paid. So instead of waiting for your company's pay schedule, you can say, "Oh, I worked today. I'd like to get paid today." And we keep rolling more and more features into that and making it more and more cluttered, but the features keep getting used, so we'll keep doing it.

Bill Cilluffo:

No, that's awesome. We're really excited about all that you guys have done over the last few years later in the podcast. We're going to dive a lot deeper into sort of Wagestream and kind of the story, et cetera. But I'd love to start more by talking about you and getting a little bit more of your background. I mean, you've been in tech for over 20 years, anywhere from youth sports in San Francisco to social enterprises and Cambodia and Laos told me the other day that you'd love to start a company someday in Nigeria. At a high level, I'd love to just hear a little bit about your story and background.

Portman Wills:

Yeah, I mean, I think, look, we're all products of our experiences. So my experiences were went to... By the time I graduated high school, I had been to 14 different schools in 12 years. So a bit of that international brat background, so get kind of restless if I stay in one place for too long. And I think professionally I was super lucky. I got to work at Microsoft super early in my career actually as a teenager, and knew that I didn't want to do that. I didn't want to work at a big tech company even though I'm a computer nerd. So everybody told me that's what I was supposed to do.

And then right at the time that I was at Microsoft, an academic name, CK Prahalad published a pre-print of what would eventually be a book called The Fortune at the Bottom of the Pyramid that was about the what's going to happen as 3.5 billion people get lifted out of poverty and all of the enterprises that are going to have to be created to serve that population. So that was and has been for, what was that 25 years, a bit of a North Star for me. And it's a great book, plug, put it in the show notes. Is that what they say on podcasts? It'll be in the show notes. I think that's what they say.

Bill Cilluffo:

Yeah, I love it. I love it.

Portman Wills:

And you can get it, Bill, you can get that sweet, sweet affiliate revenue and get eight cents or whatever if anybody buys it. But it's a great book and it talks about this concept of a social enterprise, of a business that helps those who are less fortunate but still pursues a profit. And so then the decades since then have been trying to chase that and that has, like you said, brought me to Peru, India, Cambodia, Laos, the slums of San Francisco. So all over the place. And it feels like I know you said we'll get to this, but in many ways, Wagestream feels like the culmination of the past 20 years of trying to do that.

Bill Cilluffo:

The book that inspired you talks about probably mostly emerging markets and people getting out of poverty, but obviously Wagestream is very much focused on a similar problem and developed markets where lots of people have issues and dealing with their cash flows, and there's plenty of people that really need help all around the world.

Portman Wills:

Exactly.

Bill Cilluffo:

The stat you quoted, 14 countries growing up, I thought my wife moved around a lot. You've got her beat by a mile.

Portman Wills:

No, it was just to be clear, 14 schools.

Bill Cilluffo:

Oh, schools. Okay. Well, that's still a lot of schools.

Portman Wills:

That includes getting kicked out of schools in the same country.

Bill Cilluffo:

Well, we're going to have to explore that in a minute. I didn't realize that part of it. But anyways, talk to me about these 14 schools. I mean, that's obviously got to have a huge impact on how you grew up. I mean, I'd love to hear more about growing up and how that influenced you.

Portman Wills:

Yeah, I mean, look, I have an amazing mother and she is a teacher, was a teacher. And so sometimes between schools she would just say to us, "Hey, you guys are not going to enroll for the next three months, and we'll just bum around a European city and go to museums for three months." So very ahead of her time I think in that regard. But yeah, moving schools a lot. I think either, and a lot of my friends are also international brats, and we always joke like it either screws you up for life and you're like a misanthrope and low functioning adult, or you can roll with anything.

And so I'm lucky that myself and my brothers for that matter, we got the role with anything outcome from it. We haven't moved our kids 14 times, but we've been around both coasts of the US now in Europe. And I do think it builds a resilience in children if you give them that experience of changes, ghouls, making new friends and any curve ball that life throws you, we're an amazing species. You can deal with anything. And so I think for us, with my mom bringing us up that way, what my brothers and I got out of it is there's no curve ball that you can't handle.

Bill Cilluffo:

I can see that. I mean, we've moved our kids a lot less, but they've even gone from DC to Toronto for a few years and back. I mean even that experience is pretty eye opening.

Portman Wills:

Yeah, exactly. Now we've been in London for four years and which is the longest we've lived anywhere as a family. And so now they're like, "Wait, is there another year we're going to stay?" So now we have the opposite problem. If they're like, "We have a great life, everything's amazing." And they're like, "Wait, well you wouldn't stay a fifth year, would you?" What?

Bill Cilluffo:

You're making me nervous Portman. You're making me think you're going to leave somewhere. I hope not. So you did all these excursions. What's your favorite or most memorable of these excursions that you did as a kid?

Portman Wills:

Oh, man. Good question. My mom actually tried to have us drop eggs off the Leaning Tower of Pisa with the physics, the elementary school physics experiment where you put them in a parachute or egg, right? And so we, she smuggled them under her park and we were all going to do, but they got discovered and confiscated. So we never got eggs off the leaning tower.

Bill Cilluffo:

You just had to take the picture where you were holding it up instead. All the rest of the-

Portman Wills:

Yeah, like every other a-hole, exactly. So that one sticks out. My wife was going to kill me for saying there was a exhibit at the V&A Museum when we were kids on origami, the Japanese art of paper folding. And my wife always likes to make fun of how into origami I got. Cause when we were dating and she would go over to my mom's, my mom would be like, oh, do you want to see all of Portman's origami books from when he was really into origami? And she's never lived that town. So anytime I do anything stupid, she's like, "Oh, is that your origami books?

Bill Cilluffo:

Are these books in the Wagestream office? Can I check this out next week when I'm there?

Portman Wills:

Yeah, please come. I have far too many origami books from the 1980s.

Bill Cilluffo:

That is awesome.

Portman Wills:

I feel so fortunate that I got that experience, and we try to do a similar thing for our children, maybe slightly less hectic than my upbringing was, but hopefully you can give the kids a set of experiences that they'll remember and take with them.

Bill Cilluffo:

Definitely. Definitely. So one more question about childhood before we move on. I was instructed by a very good source that I had to ask you about owning chickens.

Portman Wills:

Oh, yeah. Well, so we lived in Sonoma, California and everybody around us was into agriculture of somehow. Obviously, a lot of people grow grapes, but then on one side of us was a dairy farm, on the other side was a marijuana farm. And so we were like, "Okay, we got to get into agriculture." And so we started with four baby chicks and then it got kind of spiraled out of control and we had 58.

Bill Cilluffo:

Holy cow.

Portman Wills:

By the peak. So we had 58 chickens. And I would spend my weekends building the Taj MaChicken, which was this giant, started as a little chicken run and then got bigger and bigger and swings in trap doors and solar panels. And because I'm a nerd, so I really dorked out over the chickens. And when I met Peter, my co-founder of Wagestream, we were talking about this because he had two chickens. And I was like, "Oh yeah, look at my chickens and he'll never leave me this down." I fire up my phone and I have, it's like the CIA, right? I have six live camera feeds of the chickens from all angles. And he was just like, what loser am I with right now.

Bill Cilluffo:

So do you think this is your retirement plan? You're going to be a full-time chicken farmer?

Portman Wills:

I mean, listen, our chickens have a very good life. It would be a wildly unprofitable venture if we tried to do it for profit because our kids give them baths and massages. But we have chickens here in England now too as well. Not 58, but eight. And it's great, and the eggs are phenomenal. And as Bill knows that I'm a big... I love food, I'm chronically overweight and farm fresh eggs are just delicious.

Bill Cilluffo:

That is pretty phenomenal. Imagine you cook up a mean omelet in the morning.

Portman Wills:

Yeah. Every day.

Bill Cilluffo:

That's awesome. One last exploration here before we get more into the Wagestream story, which is a wonderful one. You're a wahoo. I know. Went to UVA and we're an Echols Scholar. Talk to me about your time with the Cavalier Daily. That sounds like you had a very big impact on the school paper.

Portman Wills:

Oh, wow. Yeah, that's going back. So...

Bill Cilluffo:

And we do research Portman were very professional.

Portman Wills:

Geez. Very impressive. What an operation. So the Cavalier Daily is the second oldest college newspaper in the United States and has been published continuously every weekday since the 1800s. And when I arrived at UVA, there wasn't a website, and this was in the mid to late '90s. And so it was like, "Oh God, we need a website, obviously." And they were like, "Cool, cool." And I was a freshman. Sorry, first year.

Bill Cilluffo:

That's right. That's right. UVA is very particular about that.

Portman Wills:

It's totally snooty about this. And I was like, "Yeah, no, I'd love to do the website." And they were like, "Cool, cool, cool." Well, look, we wrap at about 2:30 AM is when we send the paper to the printers in Culpeper, Virginia for it to be turned around and delivered for 6:00 and so, "Yeah, why don't you just come," this is the third day of my freshman year. "Why don't you just come to the office at... Yeah, just before 2:30, 2:25 and make a website."

And so I did rode my dorky little bike from dorms to the office in the middle of the night and got all these Adobe files and then started picking through and the first online edition, so started at 2:30, first online audition was published at like 8:15. So it was pretty slow. And then was like, "Ah, yeah, I got to get more efficient at this." So yeah, we built up some software to convert from the desktop publishing stuff to web, but it was fun. So for the whole time I was at UVA from, except the first two days before, sorry, we had a website, and it was one of the bigger college online newspapers in the '90s and we got some AP awards and stuff that is really going back.

Bill Cilluffo:

That's awesome. How so long did you have to do all-nighters every single day before you could put yourself out of a job with code?

Portman Wills:

Six months.

Bill Cilluffo:

Wow.

Portman Wills:

Yeah, I didn't know what I was doing. And now that would be a day and a half of work.

Bill Cilluffo:

I don't even want to ask you what your GPA was-

Portman Wills:

Not good.

Bill Cilluffo:

... nonsense.

Portman Wills:

Not good.

Bill Cilluffo:

But you had a bigger impact on the world. That's even more important. So...

Portman Wills:

Wow. Credits your researchers that is going back.

Bill Cilluffo:

No, that's awesome. That's awesome. Well, look, I love the backstory, obviously gives us a bit of a glimpse as to who Portman is, but let's talk about Wagestream. I mean, you guys have one of the more interesting founding stories that I know. So I'd love to hear in your words a little bit of the Wagestream founding moment and how it all went down.

Portman Wills:

Yeah, well we can't talk about this without talking about Greg, obviously. So Greg Mazanec a brilliant partner at QED, sadly passed away a few years ago. But Greg introduced Peter and I, so my co-founder and I to each other. And Greg, I had known... God, I could do a whole podcast on Greg's stories and maybe we should sometime, but Greg at a previous company. Greg was our intern, and so we knew Greg before QED, got their hands on him and had Caitlin, my wife and I knew Greg and Elaine as they were dating and as they got engaged and got married. So just a sort of lifelong friendship with Greg. And then similarly, Greg knew Peter very well because Greg and Peter worked together at Living Social. And so as I play my previous company and Peter's previous company, we were both realizing that we're going to be exiting and kind of looking for the next thing.

We both emailed Greg and said, "Hey man, you're looking for something else to do. Let me know if you're here of anything." And as Greg tells it, those email, as he told it, those emails came like 30 seconds apart, which probably means they came a week apart, but better story if they're 30 seconds. And so he was like, "Wow, two would really hit it off doing anything together. So he connected us and then Greg also laid out a bunch of ideas that just off the top of his head projects to work on, and I don't even remember, I think he said six, seven, eight, nine ideas. And I don't remember what any of the others were because as soon as he explained, "Hey, and by the way, it's really weird how people get paid every two weeks and they need money more frequently and they've earned it, but it's just locked up at their employer."

And if you think about it, actually every working person is giving a two-week loan to their boss. That's kind of messed up. You should do something about that. And that idea just stuck in both Peter and myself, both our brains from the moment Greg seated it.

And then I had a flight on the 3rd of January to Heathrow. I'd never met Peter. We had spoken on the phones after Greg introduced us and we had traded emails but never met. So he picks me up on the 4th of January, red eye from California picks me up and we went and started talking about Wagestream. We didn't call it Wagestream at the time. And so that was the 4th of January. And if you look on the UK filings, the company was incorporated on the 7th of January. So it did not, it was really one of those just everything made sense, everything clicked into place and we just knew this was a problem we wanted to tackle. And so I flew back home, told my family, "Hey, we may be moving to London, pack up the chickens and the rest is kind of history."

Bill Cilluffo:

That's pretty amazing. Let me just take a real quick detour on Greg and I agree that we could do a whole podcast on Greg, but it even was so tragic when he passed away and we spent many years dealing with a number of addiction issues that most people really were completely sort of unaware until everything went down. Clearly mental health in the startup world is an important issue. And so on the QED side, when he passed away, I know Nigel made a promise to Elaine, his widow to kind of never let an opportunity go past. And his family has supported a great charity called Operation Lighthouse, some that I know both QED and Wagestream have supported. The whole mission of the organization is to try to highlight the impact of addiction in the startup community, which is probably a much higher issue than most people really realize.

And so Operation Lighthouse has worked to develop a program called Just Five, really trying to educate folks in startups and really building on the idea that, look, this is a disease. It's not a character flaw. It affects people and in incredible ways that they don't understand. But Wagestream was nice enough to be one of the early pilot companies for the program. We've had the chance to now roll it out to 50 of our companies in English-speaking world in the US and UK. We've now rolled out a Spanish language version to 22 portfolio companies in Latin America.

Portman Wills:

Yes.

Bill Cilluffo:

So all of you listening, we would encourage you to try to learn more both about the issue and encourage you to come to qedinvestors.com and search for Operation Lighthouse. We think it's a great program. It's only a start. This program itself is mostly about awareness and there's plenty more that can be done, but it's really an important issue. It was awful to lose Greg, and we want to do the best we can to keep honoring his memory.

Portman Wills:

Awesome. That's all. I didn't know that was in the LatAm countries too. That's great.

Bill Cilluffo:

Yeah, no, we're excited. Hopefully Portuguese is next and hopefully we can keep helping translate it to other languages.

Portman Wills:

Fantastic.

Bill Cilluffo:

But sort of back to Wagestream, and obviously we heard how important Greg is to the whole story there. It sounds like Greg talked to you guys about a number of ideas. I think Greg lied to us. He told us our mission was to sell you guys on earned-wage access. Maybe he just wrapped that up in a bunch of other company ideas because he knew it would resonate to you. What was it about the idea that it sounded like from the minute you heard it that you were sold? What about the concept was so resonant?

Portman Wills:

It is true that from the millisecond it was explained. I was like, "Oh my God." It's like a inception mind virus. You can't actually get it out of your head. And I think it's probably three things. One, we talked about, it's the culmination of a ghost I've been chasing for 20 plus years of how do you build a business that has an impact on those less fortunate, but also it doesn't rely on donations. And so it's pretty immediately clear that if I'll come back to the math in a second. So that one part. The second is that I had done a lot personally, I had done a lot in developing nations and then we had a startup called Free Pay that was trying to monetize people's attention in the us. So if you didn't buy something with your money because you didn't have money, could you monetize watch ads and monetize your attention and get the toaster oven or coffee maker that you needed?

And Free Pay really opened up to me, it was the first time I had had a product that directly served the hardworking, lower income segment of society and just how hardworking they are that people would grind away for to get a tennis racket for their kids. You take a real example of something a user would really run down. So that theme as well. And then the third is, and this is where just life is a super funny set of coincidences, but maybe four months before Greg mentioned the idea, we had just gone on a vacation in the UK to Notting Hill and we went to the park every day. It was a beautiful summer, 2017, went to the park every day with our kids, met other families, and we were there on the boundary of a month. So we were there from end of June to beginning of July and we would meet these families in the park and they'd be like, "Oh, come over have a glass of Prosecco. Oh, Americans. Yeah, come, we'd love to meet you."

And then that all dried up at the end of June and we thought we had said something offensive and stupid, made fun of Trump too many times or something. And then the 2nd of July we saw these together, "Hey, come over." And we're like, "Oh, wow, we thought we had offended you." And they were like, "Oh no, it was the end of the month. So we shut ourselves in. We don't do anything." And these are dual income professional families of accountants and doctor. And they're like, "Oh yeah, in England everybody, they just shut it down last weekend of the month." You were at home with Netflix spending no money because we get paid once a month and we're out of money by.

And I had thought when we heard that from one family, I thought they were kidding and exaggerating, then we heard that from a couple other families and I was like, "Oh, this is a real phenomenon in Europe that people change their social calendars based on the pay schedule." And so it's like those three things that one, trying to build a social impact business that also generates its own profits to be sustainable, to realizing that the lowest earners in the Western world work really, really hard and every penny counts. And then three, this concept that specifically in Europe, the monthly pay cycle is such a burden that people change their entire social calendars around it. And so I think I was primed for all three of those things. So when Greg said it, I was just like, "Oh my God, you have to do that."

Bill Cilluffo:

No, that's incredible because I think the idea that ultimately got us so excited was only based on a two-week pay cycle, right? So it's even more dramatic in the UK and many other countries around the world where it's a full month pay cycle. That's pretty incredible. You went and had your meeting with Peter, you guys decided to start the company three days later. I know you did do a bunch of research to help convince yourself. So this is a real thing. So I understand there was much casual dining to be done in the shadows of Windsor Castle. I know I need to hear more about.

Portman Wills:

That's spot on. So Peter, he picked me up at Heathrow and Heathrow is like an hour from London, but only 15 minutes from this place called Windsor. And Windsor is where the Queen, I guess you say the King now, where the King lives. That doesn't sound right. It's where Queen Elizabeth.

Bill Cilluffo:

That's 70 years, it's going to take an adjustment.

Portman Wills:

It's going to take a beat. So it's 15 minutes from Heathrow and it's a beautiful little small English town. And there's the castle literally up on the hill and then down below it are hundreds of shops and restaurants. And so we thought it'd be a good place to park ourselves for the day. And so drive over there and we just armed with nothing other than Greg's inception seed of, "Hey, people should be able to pick their own pay schedules, not wait for their bosses." We were in Windsor for actually two days, and we talked to 250 people, and we went in every single shop, restaurant boutique, ice cream truck, just everywhere and talk to everybody and ask them, how often do you get paid? Because I personally still didn't believe this thing that people were paid monthly. I thought, oh, maybe that's only accountants in central London that are paid month, right?

Because it's so for an American and for those listening who are not from the US, this is such a foreign concept to an American getting paid anything other than every two weeks. So I still kind of didn't believe that. So we asked how often do you get paid? How often do you wish you could get paid? And if there was an app that lets you get paid when you wanted to, would you use it? And I'll never get, so we did 273, I think interviews and 272 said, "Yes, please." And one I'm still to this day convinced did not speak English. It was the only possible explanation.

Bill Cilluffo:

Well, the fact that you got one no meant that it was real research because otherwise you would've thought it was fake or something.

Portman Wills:

Yeah, exactly. Yeah, we got one, no, out of the 270 something people that we talked to. And it was just amazing to hear. And that's when we first started, and I'll have to watch myself not to get on soapbox about this, but that's when we first started collecting these little stories of how impactful a rigid pay cycle is to people's lives where they're like, "Oh, I needed to get home after work. It was the last day of the month, and I had no money in my bank account. My credit cards were maxed out, and the train fare was $9 that I just didn't have." And you start to collect these little vignettes and stories and realize how just on the edge and on the margin, so many people are living where tiny, tiny increment, just getting access to nine pounds is the difference between sleeping in a train station or in your own bed. We got a good number of those in those first few days.

Bill Cilluffo:

Well, and especially how many people wind up turning to 1% interest a month or a day, a payday lending type businesses to solve some of these problems. And in so many cases, especially with a monthly pay cycle, they've already earned the money. They just don't have access to it yet. So it's easy to see how valuable that can be to people that, I forget the statistic, but the vast majority of folks in the US or UK don't have $300 or 300 pounds to deal with a car breaking down or kind of a minor medical issue.

Portman Wills:

Exactly, yeah. The UK status, 57% do not have 200 pounds of savings for some unexpected expense. So if you're in the 43, great, you can cover it, but in the 57% you're kind of out of luck unless something like a Wagestream exists.

Bill Cilluffo:

Yeah, no, it's stunning. So as you were doing this research, which sounds like it was incredibly compelling, you also managed to get some unexpected help from a government agency as part of this research mean, can you talk to us about that?

Portman Wills:

Oh, I forgot. Yeah, that is such a good story. So Peter, we were trying to figure out after talking to 270 people, okay, well exactly how many people in the UK are paid monthly and you can Google this and you come across stats that are tangentially related from what in the UK is called the ONS, Office of National Statistics. And on these stats that talk about labor categories and stat at the bottom of a couple of them was the same name and telephone number of the researcher who had compiled the stats. And so, Peter's like, "Let's call them." And I was like, "No, you dummy. You don't call the gov, you're not going to, we, I'm here for only a couple days. We can't just be calling government agencies and hold." He's like, "I'm going to call them." And puts the phone down on speaker, right?

And it literally goes like this, "[ring...], hello." Not even a full ring. A person picks up and Peter's like, "Is this Mr. Smith of ONS? Yes, we were on the website and looking at." And he was like, "Oh, lovely." And this guy is can't, I'm not going to do the accent, but he's Welsh, right? So in Wales sitting there, government job pumping out research and was so excited to A, get a phone call B, for it to be about a question that he had the data for somewhere. I wish it was in the era of Zoom and we could have seen the archives behind him. I have no idea if he's in a Harry Potter library or just like a shed, right? He's like so excited. He's like, "Yes, yes, yes, I know exactly what data's set to go to get this. Let me take that up for you."

And honest to God, in 20 minutes later, we hang up the phone and there's an email from a government agency with the official stats showing that 89% of all employed people in the United Kingdom are paid monthly. 7% are paid four weekly, which is not monthly-

Bill Cilluffo:

Four weekly.

Portman Wills:

Yeah, four weekly that's 13 paychecks a year instead of 12. And that only a tiny, tiny, tiny percent are paid more frequently than that.

Bill Cilluffo:

Maybe that was your one out of 273 that didn't need the service.

Portman Wills:

Yeah, exactly. But I mean for anybody listening who's tried to deal with government bureaucracy, what an amazing experience to call a number, get it picked up, have somebody who bespoke custom research for you and email you in 20 minutes. Yeah, it was unbelievable.

Bill Cilluffo:

It is amazing. As you talk about founding stories in the early days of companies, so many people have some random example of serendipity that kind of went their way. Now, I'm sure I'll ask you here in a minute, what are some examples that probably didn't go your way? And not everything's roses, but it's always nice to have those random strokes of luck when you can find them.

Portman Wills:

Totally, totally. That's people's founding story for a reason is because nobody... There's no company that's a linear, you graduate from college, and you say, I'm going to found a company and it's going to do X, and if A then B, B then C. They're not linear paths.

Bill Cilluffo:

Definitely. Definitely. Well, to that end, let me dig into that. So I'm sure you've made 15,000 choices in your process of building Wagestream over the last little bit. I wonder if you could start by sharing one or two of them that you feel like you absolutely got right. Where's an interesting fork in the road where you guys had to make a choice or make a decision or pursue some strategy and you look back in hindsight and said, "You know what, we just nailed it. We got that one. And it was big contributor to our success."

Portman Wills:

It's so much easier to come up with the ones you get wrong than-

Bill Cilluffo:

We'll give you that chance in a minute.

Portman Wills:

No, I know, but there's a fair number of technologies that we chose that we're still on that are good choices. That will be for a Fintech podcast, it'll be super uninteresting. But shout out to my boy Postgres, which is the greatest relational database on earth. That's a good choice. Never look back on. But in terms of business strategy, the one that probably comes to mind is, and actually Yusuf who's a QED partner and really kind of the third co-founder of Wagestream, Yusuf was a big proponent of this. So we engaged the regulator, the financial conduct authority, super, super early in our journey. And even though this is obviously not credit because you've earned the money, if you punch in punch out of your punch clock and you've earned 80 pounds, getting paid 80 pounds is not credit because you've earned it. If you get paid 81 pounds, that 81st pound would be credit, but not the 80 you've already earned.

And so it's not consumer credit. We didn't need to engage with the FCA, but we chose to. And I think that's been, that was such a good strategy for two reasons. One, I think it paved for the way for every governmental and regulatory interaction we've had since then, which is like, "Hey, here we are. Here's what we want to do, what do you need to know? And we're an open book." And that's worked really well with a variety of regulators over the years. But secondly, again, with this theme of the phenomenal competence of UK government agencies, we probably got lucky that it was the FCA and not a different organization, but they were so wonderful, and they were so clearly focused on just getting great outcomes for consumers in this country. And so rolling up our sleeves and figuring out what exactly, where does this sit because it's a weird gray thing in between payroll and credit and lending and wage and hour laws. So rolling up our sleeves and working directly with the regulator from the very beginning I think was a good choice.

Bill Cilluffo:

Yeah, I think in the world of generalizable learnings, I think that's an awesome one. So many Fintechs are out here to blow up the world and disrupt the status quo, et cetera. And well, disruption can be really powerful on behalf of the consumer. Sometimes so many companies are their own worst enemy by trying to do everything outside the system when sometimes working within the system to change things for the better can be an easier path. I imagine there's several interesting crypto related companies that might be reflecting on that point as-

Portman Wills:

Yeah, exactly. Yeah, good timing. And by the way, I just spent 17 minutes and you summarized it in 17 seconds, so thank you for that.

Bill Cilluffo:

So I'll give you the chance to go the other way. Thinking back on mistakes you've made as you've built Wagestream so far, is there a particular kind of mistake that stands out that you were able to learn from and is kind of impactful?

Portman Wills:

I think it's got to be in the tens of thousands of mistakes that we've made. If you took a census of them in Excel, you'd almost run out of Excel rows there've been so many. One of the big funny early ones that we tell all our new employees is how the idea makes so much sense. Why would you hear it? And you're like, "Oh yeah, the world should exist where people get paid as soon as they earned it and not have to wait." And so, Peter and I thought there would be a line of CEOs around the block to sign up to Wagestream to sign up their businesses. And we joke that at the forefront of our mind was the private security we would need on the office door to prevent the CEOs of the largest businesses from pounding down, "I need this, I need this right now."

And so we invested in a very nice door and a very nice secure, and then got the pen out the fountain pen. All right, we'll give you a nice pen to sign. And then crickets and just nobody was there to sign up on day one. And I think we've made versions of that mistake so many times where you think that because something is a no-brainer for a business, that you just have to explain it to them and they're going to sign up. And really, this is my first B2B enterprise sales business. Same with Peter. Most of our background's been consumer and oh my God, the hoops that you have to go through to sign an enterprise and the stakeholders and the meetings after meetings, and anybody who's listening who works in this will know what I'm talking about. But my God, it's just so much work and we consistently underestimate that still to this day, where we are like, "Oh, let's go into a new sector or a new country, new geo, and oh yeah, let's just tell everybody, hey, we're here. Come sign up." And no, you just have to do the work.

Bill Cilluffo:

Yeah, I mean, most large companies probably have about 50 people all empowered to say no, and not a single person ever empowered to say yes and figuring out a way to get there. And it's a pretty long journey. But again, as you guys have shown persistence, and ultimately when something is in their best interest, I'm pretty convinced over time they will usually pursue that route. Sometimes it can be complex.

Portman Wills:

Yeah, it can be complex. And I think the biggest thing is it's taught Peter and I, patience, you do have to just lay the groundwork, put together the value prop, wait for the buying cycle, which isn't always right now, it's not when we want, certainly it's when it's convenient for them. And then you know, do all that work and then eventually you'll harvest those accounts, and they'll sign up. It just takes a lot longer than you wish.

Bill Cilluffo:

Definitely, definitely. Well, look, one last topic I'd like to explore before we wrap here. I kind of ask you something that went well and something that was a challenge at Wagestream. I'd love to ask you more personal versions of that question. So if I were to pull everyone in the office that works with you, what would they say Portman's true superpower is?

Portman Wills:

I mean, this one's been easy for my whole life, and I know it sounds stupid, but it's the luckiest person. I've literally won every door prize at every event or gala I've ever been to, even to the point where we had to stop going to the kids' fundraisers because it just got embarrassing because we'd show up in balloons and confetti like, "Oh, you're the 745th person to enter." It's unreal. And I remember when I told Yusuf this and he was like, "No, people create their own luck." And he was like, "Oh, it's not." And then a year later he was like, "Hey, remember when you told me you were really luckiest." He was like, "Wow, you weren't kidding." It doesn't make any mathematical-

Bill Cilluffo:

Portman you realized the US had a $1.6 billion lottery couple weeks ago. Maybe you should have invested in some tickets.

Portman Wills:

I really should have. I completely missed that and thank gosh, because I probably would've won and then would have been like, "See you later, Bill. We're not doing that podcast on the 22nd."

Bill Cilluffo:

No, you still would have kept a date, I'm confident.

Portman Wills:

So no, that's a genuine thing, is being lucky. And then a slightly less flippant one, I think. And I think in all seriousness, you're the best you Bill Cilluffo or the best person I've ever met professionally at this. And I try to be a sort of just a top 10 and then I'd be happy. But the ability to take a complex problem and then just distill it down to the one core question. So I think a lot of times in business things are incredibly complex and you have a decision and there's... You think there's 15 axes that you have to look at, and then the skill is really just saying, actually, doesn't this just all boil down to if A then B, if not A then C kind of thing. And I think you and our board meet you do that incredibly well. And I try to do that for our team at Wagestream as well. I think it's a practice skill and you can get better at it over time.

Bill Cilluffo:

Yeah. Well, look, I appreciate that very much. I mean, in your case, being able to do that with juggling business issues and technology issues, I mean, your guy's technology quite confident is the best in the industry. So you can see where that type of problem-solving really helps build technology that really gets right at what you're trying to build. If I can flip that around, what's one thing that you wish you were better at that you've kind of worked on.

Portman Wills:

Yeah, how much time do we have? I got this. So I said how early in my career I worked at Microsoft, and one of the things they do incredibly well, especially with young employees early in their careers is sort of mentoring and coaching and feedback, or at least they did at that time. I assume they still do. And I remember my first sort of formal feedback from Bojana Ostojic, my assigned mentor was about how I had a real problem with conflict, and I would avoid conflict instead of confronting it. And that often led to worse outcomes for the business, for customers, for right, because you can't run away from conflict.

So that was at the age of 19, and I've been trying to work on that ever since and consistently get that feedback still decades and decades later that I'm not good at conflict. And so it's one of those examples of, you can teach yourself a lot of things, but there are some deficits that we all have that it takes a lifetime to get better at. And so for me, that's one of them I try every day, every week. And I think if you pulled people at Wagestream, I still probably suck at it, but yeah, I just find it incredibly hard because I want everybody to be happy and get along, and that's just not always the case.

Bill Cilluffo:

Yeah, I mean, that's a pretty easy one for me to relate to. I certainly have spent much time sort of thinking about that. And again, it's hard. You never want to be the ass that kind of gets in someone's face, but then you realize, look, if there's something that needs to be said, the sooner they hear about it, the sooner you take action, everyone winds up being better. But it's a tough one though, that's for sure.

Portman Wills:

Yeah, correct. I mean, scientifically and objectively, I can look at all the times that I've screwed up by not being an ass about something and saying it out loud and scientifically you're like, "Oh yeah, those are all worse because you beat around the bush with it." Doesn't-

Bill Cilluffo:

Doesn't make it any easier.

Portman Wills:

Exactly.

Bill Cilluffo:

All right. So last question, and look, really appreciate you spending all this time with us today. I think this has been a fantastic session, but if you were meeting a group of young entrepreneurs and had to share one key tip with them, folks that had not yet started their first business, what would you say?

Portman Wills:

Yeah, this is so easy. It's get very, very comfortable with failure. The single most important thing in being a... I mean, I wouldn't call myself a successful entrepreneur, but in becoming a non-abject failure of an entrepreneur's is like you just have to be okay with failing, with screwing up and get knocked off the horse, get back on. And so we tell our kids this all the time that I'd rather, my daughter, oldest daughter's a sophomore, is taking four APs as a sophomore. And the school was like, "Hey, I think this is too much course load and you're probably not going to get straight A's, which you're used to." And I was so proud when she was like, "Yeah, that's fine. If I fail, I fail." And both my wife and I were like, "Yes, that is awesome." I think that's the single most important piece of advice that was given to me and that anybody can give to sort of first-time founders is just be okay with failing.

Bill Cilluffo:

No, it's fantastic. I love the lesson. I mean, look, most startups don't succeed. And to your point, even those that do succeed are going to go through many, many tough days and many, many challenging times and have to learn a lot along the way. So that really resonates. I really appreciate having you here. It's been a fantastic 45, 50 minutes. I think we're going to wrap. We can probably keep going for hours, but I know you've got many things to do in building Wagestream. So thanks to all our listeners for joining us today. And until next time, take care and thanks again.

Portman Wills:

Awesome. Thanks, Bill. Appreciate it.

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