HR isn’t what it used to be, and neither are career paths. In this episode, we sit down with Jon Lowe, Chief People Officer at DailyPay to explore the evolution of HR, the importance of self-awareness in career choices, and why adaptability is the key to success. From home improvement projects that went hilariously wrong to lessons learned in the workplace, we discuss how grit, intentionality, and accountability shape personal and professional growth.
In this episode, we look at earned wage access, HR transformation, professional development, and career pivots—breaking down the unpredictable nature of the job market and how to find the right workplace fit. Whether you’re in HR, exploring new career opportunities, or just trying to navigate life’s unexpected turns, this conversation is packed with insights and laughs.
Key Takeaways:
➡️ Home improvement projects can spark unexpected (and hilarious) neighbor disputes.
➡️ The role of HR is evolving—fast.
➡️ Self-awareness is critical in shaping career paths.
➡️ No two days in HR look the same.
➡️ Personal growth often comes from career pivots.
➡️ Humor makes even the toughest career lessons more bearable.
➡️ Workplace dynamics are changing, and adaptability is key.
➡️ Career paths are rarely linear—embrace the pivots.
➡️ HR titles and responsibilities are often misunderstood.
➡️ Family expectations can heavily influence career choices.
➡️ There’s a lack of real resources for career guidance.
➡️ Most people don’t end up working in their college major.
➡️ Finding work you enjoy is more important than chasing a title.
➡️ Grit and adaptability determine long-term success.
➡️ Building something meaningful beats maintaining the status quo.
➡️ Intentional career choices lead to better opportunities.
➡️ Self-reflection is essential for personal and professional growth.
➡️ Accountability is the backbone of career development.
➡️ The job market is always changing—flexibility is a must.
Chapters
00:00 Building Projects and Neighborly Relations
05:01 Introduction to DailyPay and HR Evolution
10:00 The Changing Landscape of HR
12:50 Jon Lowe's Journey: From High School to Career
20:00 Self-Awareness and Career Choices
20:32 Navigating Career Choices and Education
23:00 The Journey from College to Career
29:01 Finding the Right Fit in the Workplace
35:12 Building a Career in Tech and Beyond
41:11 The Importance of Grit and Adaptability
46:52 Intentionality in Career Growth
Connect with us here:
🔗 Connect with Jon Lowe: https://www.linkedin.com/in/lowejon/
🔗 Connect with William Tincup: https://www.linkedin.com/in/tincup/
🔗 Connect with Ryan Leary: https://www.linkedin.com/in/ryanleary/
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[00:00:00] Before we move to the next thing, I have a funny story. Are you ready, Ryan? There is no doubt that I am always ready to hear one of your stories. Always. The first time I managed HR, I had no idea about compliance. None. I had a friend come out and audit what I had done. I was pretty well set up, but I missed the memo on compliance posters. Yep, back then, HR posted safety and compliance posters in the brick room.
[00:00:28] I laughed, of course, and said, who cares about posters? She said, your city, your state, and most importantly, the federal government cares about those posters. HR friends, you know the drill. It's endless admin tasks and compliance headaches, trying to make time for what really matters, your people. Bamboo HR takes the stress out of HR, so you can focus on what you do best. We get it. HR is hard, but Bamboo HR is easy.
[00:00:57] Do a demo of Bamboo HR today. Do what a lot of our listeners have done. Get a free demo at BambooHR.com slash free demo. Get back to doing what you actually love in HR. Go to BambooHR.com slash free demo. That's BambooHR.com slash free demo.
[00:01:21] In my third year, I realized that there was like this one class. It's called like econometrics 3-0 whatever. And you know that moment when you're like looking around the classroom and you're like, it's not that I'm not studying, but like everybody else is getting this. I'm working wicked hard. Yeah. Like, I'm just not. And like, these are the same murderers that like in a year and a half's time I'm going to have to try to compete with for jobs. Like, maybe this ain't for me.
[00:01:59] Hey, this is William Tincup and Ryan Leary. You are listening and hopefully watching the Inside the C-Suite podcast. We got John Lowe from Daily Pay on today with us. And we've had a wonderful pre-show. Probably one of the funniest pre-shows we've ever had. Probably better than the episode to come. Oh, 100%. We should have recorded that. Yeah. So let's do some introductions. John, would you do us a favor and the audience a favor and introduce yourself? Sure. My name is John Lowe.
[00:02:27] I support the HR program here at Daily Pay. Technically, my title is CPO, but I'm a doer of many things around here. We operate within the earned wage access space. We've got a really great team. There's about 850 of us. We sit mostly in New York, but we're kind of all over America at this point. Right. Right. You're global pay too, right? You can do global or is it still in the four walls of the U.S.? We're mostly in the U.S.
[00:02:55] We have like a small footprint in Canada. We're starting into the U.K. But, you know, I would say that we're predominantly U.S. focused right now. It's CPO, Chief People Officer, yeah? CPO. I will say that there's an element of like confusion on ADP. It says I'm a CHRO. Yeah. I would say that 95% of the time. You can call me John. Hey there.
[00:03:24] My in-law is calling me asshole, so that's cool. Yeah. I'll respond to anything. Go ahead, Ryan. Yeah. Yeah, yeah. Is there really a difference though between CPO, Chief People Officer, and CHRO? You know, I don't know. I think that there's been kind of like an evolution of the titling. I would actually say that there's like a pretty sizable evolution of the function. Right, right.
[00:03:49] You know, if you think back over like the last 10, 15 years, that CHRO, you know, I would say that Chief People Officer is probably akin to Chief Personnel Officer. Right. Which is probably more likely what we were, you know, as recently as, you know, 15, 20 years ago. So, again, I think that out of all of the discipline areas, we probably feel a little bit confused about what it is we call ourselves and what it is that we do as a byproduct of the evolution that continues to happen within this space.
[00:04:19] Well, it's an identity crisis to people that are outside of HR. But really what's going on is HR both is evolving, but it's bringing on new things and letting go of things. So things that were important 10 years ago, projects and programs and things like that aren't as important. You have a new emphasis. Someone was asking me, first week of January, I was like, what? And they were a CPO and they were like, what do you think that we should be, that everyone
[00:04:48] else is focusing on? Five things that people are focusing on. I'm like, here's the five things, not a problem. But everyone's got, they're at different starting points. Yeah. So if it's DEI and that's important to you, great. Or if it's AI training, everyone's at a different place. So it doesn't really matter. You've got to kind of do the audit of what matters to the company and then redo your entire plan to then be adjacent or at least congruent with whatever's important to the company. Yeah.
[00:05:18] No, it's funny. Like if you think about all the other C-suite functions that are out there, finance, legal, technology. They don't change much. They really don't. Like, you know, financial years, audit tax, internal controls, treasury relations, like those are bona fides for those functions. And so I do think that like, you know, it's an interesting thing that you guys picked up on, which is, is it, well, is it CPO, CHRO? What is it that you're, you're, you're focused in on? Again, like what it is that we're focused in on this year might be very different the next year.
[00:05:53] It's so evolving. I don't think that who knows in 20 years, maybe we'll have a settled definition of what it is that like sits within the scope, but as it stands right now, it is still very transient. It's, it's interesting because what you've just. With the story you've just told makes me think of the personalities that thrive in sales, in accounting and finance, where year in and year out, there's a, there's a cadence. Whereas in HR, you know, there are some things that are, that have a cadence to them, but
[00:06:23] most of it is firefighting because at any given point, a sexual harassment claim could land on your desk. And it's like, well, I was doing this other project. Now, now it looks like I've got to do this project or not just the, those things, but anything to drop on your desk. It's the human nature of people. I mean, with, with finance and accounting, John, to your point, same thing, right? Rules change, laws change. So you adapt to that, but your job is the same. Right.
[00:06:52] I think, I think what we're seeing now more than ever is, I mean, obviously with the way people have changed and employment has changed, relationship between employer and employee has changed. Your job as specifically in your role, I mean, is changing daily. It's changing all the time. Daily change? Yeah. Nice. Nice. No punnings on it. Hashtag daily change. Pause after I said it. I'm like, yeah, that was cheesy, but I didn't really mean it that way.
[00:07:22] That is one of the, one of, one of the company references for the purposes of that. Yeah. It's, it's really interesting because, you know, when you think about the changing landscape, you know, the tax code does change, but it's like at a glacial speed. Imagine a scenario where you had a tax code, but it's broken down on a state by state basis with like different municipalities that have different rules, like New York City, Boulder, Colorado, the entire state of California.
[00:07:50] Seattle versus like a Texas, Arkansas, Mississippi, Missouri. Like it's, it's wild. And, you know, again, I think that there's this very wide oscillation that takes place. You know, the vast majority of organizations, human capital and people represent probably either their number one cost, if not their second cost. So when you really think about that idea of how close to, you know, company earnings, company performance people are, you know, it's very much day by day.
[00:08:18] We are, we live and die based off of how the economy is going. And so, you know, again, being able to foresee what's coming down. And then you spatter into that, like complaints, sexual harassment, harassment, you know, workforce stress ring. Oh yeah. Safety. What? Yeah. Any, any number of things, but like we are so exposed to elements that are well outside of control. Yeah. So yeah, every, every day is different. Every year is different.
[00:08:46] Which is exciting for some personalities, you know, for some personalities, they thrive in that because it's like, I don't have the same day twice. Whereas you talk to a CRO and it's like, they had the same day twice. You know, they're, they're, they're, they're marching sales to a quarter goal or pass the quota, whatever it is. So they have the same, they have a cadence to what they do.
[00:09:09] Whereas that personality probably wouldn't thrive in HR and thrive, uh, HR person leaders probably wouldn't thrive in that environment because it's changes addicting. We don't talk about it like that, but once you do it and you get it, you find yourself every day fighting some different fire or working on some type of different project. It's like, that's, that's actually addicting for some folks because they like it. So Ryan, you want to go backwards? Yeah.
[00:09:38] You know, I was just going to say as riveting as HR conversations are, I really want to learn about John's background. He got a huge personality. I'm just thinking there's going to be some funny stories in here. Let's do it. Let's do it, man. Let's go back. All right. So, uh, high school, let's go back to high school. What would, what did you want to do? What'd you want to be when you were in high school? Yeah. So, um, I grew up in Toronto. I grew up in Canada and went to a high school just outside of.
[00:10:07] Just, I guess it's technically in Toronto. Just barely. So you want to be Ryan Gretzky. Got it. Check. Yeah. Yeah. Trust me. You can't tell how tall I am, but like hockey and sports, like that, that, that was, that was pulled off the table real early. That wasn't going to be it. I think that like some people in high school had like a very clear view of what they wanted to do. Doctors, lawyers, engineers, whatever it was. I had absolutely no idea. I had like coming out of high school.
[00:10:35] Uh, I had two key objectives. One of them was to get into college and the other one was to make sure that that college was not in Toronto. Yeah. A hundred percent. Get the heck out of my parents' basement. And so I don't, I would say that out of most, as opposed to most of my classmates, I was the most lost. Were you voted most lost in a yearbook? Is that what you're telling us? I don't know. I've disposed of that thing many years ago. A hundred percent. It was funny. I was thinking through and I was like, you know, there's things that I'm generally good at.
[00:11:04] I thought I was going to become an economist. I had like an aptitude for, for business. Like I wasn't a killer in anything. I was like mediocre in accounting. I couldn't figure out debits versus credits. Like it wasn't really all that. Like I wasn't anyone's first pick. Right, right, right. Dodgeball. Yeah. Yeah. All right. I guess. You are describing my life right now. All right. I guess, I guess we'll take John. All right. Go ahead.
[00:11:31] It sounds self-deprecating, but I really wasn't very talented. You know what? It doesn't matter. That's the journey. Like every, everyone starts in a different place. Yeah. Those that did start, they knew exactly what they wanted to do. They went to Harvard and they plotted their career only to find out, hey, wait a minute. There's a, there's a pivot in there that I get to a point 10 years into my career and go, I hate this shit. I just, I hate it.
[00:11:59] So then they have to, then they have to reassess, which is not easy, especially if you've been thinking about a certain goal for 20 years of your life. So I think, I think it's one of those deals. In fact, I was telling, I have a 19 year old and I was telling him and my 15 year old the same story. I told him my career and I said, I've changed directions in my career. I've changed directions in my career at least 20 times. And they were both shocked. They're like, really? I'm like, oh yeah. Oh yeah.
[00:12:28] I would go this direction only to find out. Yep. Hate that. Okay. Go this direction. And they're like, we just thought that this is what you've been doing all your life. I'm like, no, no. Considering you've been working for about 23 years, that's a lot of changes. They just said there, yeah, I'm actually, I'm actually a millennial. I'm Jim Z. Yeah. Way before that came along. So what, what'd you do? It was college. Where did you go? You ended up getting out of Toronto, I'm assuming.
[00:12:56] What if I told you that your boss skydives, Tim in marketing is a magician and Sam in accounting does sums in his head while standing on his hands. Seeing sides of the people you work with, but never see sides that inform and inspire their work and that can inspire yours is what the talent show is all about. Email me, Tom Alexander, host of the talent show at talent show at backboneinc.com and show us what you got. I look forward to seeing you on the talent show.
[00:13:57] Yeah. I went to a school just outside of Toronto. It was called Queens. I think one of the things that like really shaped me as part of that process was that like my, my parents are, were immigrants to Canada. And so there are like a very limited number. Like if you have any Asian friends, you can ask them. Oh yeah. Very limited number. Doctor, lawyer. That's it. It's one of those three people. That's exactly it. So they're just like, Hey, you're going to become an accountant. You're going to become an engineer. You're going to become an engineer.
[00:14:27] Good point. That's it. Or you're going to become a lawyer, right? And all of a sudden you say, I want to do poetry. What? Yeah. Yeah. Well, I'll, I'll get to how disappointed they are. That's in the next 30 seconds. We'll get better. Yeah. Do you have brothers and sisters? I do. Okay. So did they, did they make the traditional picks? He's just a better human than us. It's funny.
[00:14:55] You know, normally your parents tried to go and mask, you know, we love equally. You both have your own. No, no. He's actually really good at stuff. He's taller. He's better looking. He's more successful. He's dating and counting. Like there were children. Like I strive to be more like my younger brother. So like I, I, I, I grew up with a bit of a complex. I still have a good, a healthy amount of that complex. So yes. That's fair. So I went to, I went to university.
[00:15:25] Also known as college. I still was along that line of like, don't really know what I want to go and do. I did some sociology, did some economics. And it's funny. One of the pivotal moments that I had, which I think, again, one of the things that you'll see through all of this is that like. Hey, it's Bob Pulver, host Q podcast. Human centric AI, AI driven transformation, hiring for skills and potential dynamic workforce ecosystems, responsible innovation.
[00:15:54] These are some of the themes my expert guests and I chat about, and we certainly geek out on the details. Nothing too technical. I hope you check it out.
[00:16:44] That dude is wicked lucky. He was like, there's so many things I could have gone off the rails in my third year. I realized that there was like this one class it's called like econometrics three Oh whatever. And you know, that moment when you're like looking around the classroom and you're like, it's not that I'm not studying, but like everybody else is getting this. I'm working wicked hard. Yeah. Like, I just, these are the same murderers that like in a year and a half time, I'm going
[00:17:13] to have to try to compete with for jobs. Like maybe this ain't for me. This door is now shut. Yeah. Yeah. It's just like, you know, it's like being a ballerina, but like just not being able to jump high and just like, like it, I was, I was not talented within that area. And whilst I think that I liked it, I just wasn't good. Right. And I remember it like vividly. I was just like, there was like this one moment I was like, okay, where do I sit in this class? Like honestly.
[00:17:43] Right. And it was like, definitely not top quartile. I don't think I'm even top half. I don't think I'm like, I'm thinking I'm in the bottom quartile of this class right now. Like awareness though. Like you knew. It's how I tell people when I graduated high school, I'm like, I graduated, you know, fourth in my class. Whoa. And people were like, it was 800 students. There was only six people. No, no, it was 800 students in high school, uh, seniors. And, uh, they're like, man, that's dope. That's great.
[00:18:13] I'm at four from the bottom. That's, uh, yeah. Four from the bottom. That track. That track. I'm schooled, but yeah. Yeah. Yeah. Well, what I think is, so John, what I think is interesting about that is I was getting the same situation. I went, I went about four years in comp sci and was like, yeah, I'm done. Like, I'm not going to be these guys. Like, and I knew that, but there was no real resources. We're probably all about the same. Right. And there's no resources for me to look at. Right.
[00:18:41] We didn't have social like it is today to look at these guys and say, it's okay to fail. So I was told you're going here, you're doing this and that's what it is. Yeah. Yeah. So it's, that's a scary spot though. How you, you know, what you're talking about. So my, I was lucky because I, I worked for almost five years before I went to college from high school to college. And my career advisor after our register and you sit down back then you'd sit down with a career advisor and they're like, she goes, listen, here's the deal.
[00:19:11] One in four people work in their major. So the current statistic is three quarters of those are working in something else. You get a degree in physics, you have a one in four chance of actually working in physics. So make it easy on yourself. You're an older student. You're probably going to be a little bit more disciplined than some of the younger students. What do you like? I said, well, I'm an artist. She was great. Do art, do art or art history or something around art.
[00:19:40] It'll be easy for you and don't worry about what you do after graduation because it doesn't matter. So I'm like, all right, cool. Went over to the art department, talked to his schedule time, talked to the chair. And he's like, man, show me your portfolio. I'm like, all right. Showed him his portfolio. He's like, listen, what do you want to do? Do you want to do an MFA? Do you want to do a BA? Do you want to do art studio? Do you want to do art history? I'm like, I kind of want to do the history side. I feel like I got the art side. I really want to do the history side.
[00:20:10] It sounds interesting. He's like, fantastic. You're going to love it. He goes, and this is when you could talk like this. And he goes, you're also, there's a side benefit. I said, do tell. He said, most of your class, 90% of your class will be girls. I'm like, really? He goes, yeah. I'm like, I'm so going into this profession. This is easy. Done. But of course, I didn't work in it. I didn't work in history afterwards. Like, it doesn't really, now we know. It doesn't really matter if you're going to get a degree in a lot of professions.
[00:20:40] Just get the thing, tick the box, and move on. So what was the first thing you did out of college? Yeah. So it's funny. So in my third year, I ended up, after I had that epiphany that I kind of solved at like the thing that I thought I wanted to do, I actually picked up like an associate's degree in HR. I did an associate's program in HR. And that was like my contingency plan. I was like, oh God, like I just need something that's going to preclude me from, I got to have some skills in something, right?
[00:21:08] And so my first job out of college was actually at, for the first time ever, my parents were actually proud of me. I got it. They must have mixed up the names. I got like one of those coveted roles in big four accounting. So I got a job as an analyst at KPMG. You didn't even have to tell them that you were in HR. You just said KPMG. No, no, no. I wasn't in HR. I was in advisory services and protection. So I got really lucky. Like I'm pretty sure this is a byproduct that they mixed up the names.
[00:21:38] Yeah. So I ended up doing that for almost a year. And what's crazy about it is that I got to this point where it was exactly the same thing. I was like looking around the room and I'm like, okay, I'm never going to get promoted here because everyone here is wicked smart. And it's just things come really naturally to them. And so that was probably one of the hardest decisions I made in my career, which is like, I'm going to, I'm going to do me.
[00:22:08] Which, you know, when, when you were hard coded to like, Hey, this is the journey that you're going to go down. And the rejection of that to be like, no, I'm going to, I can't do this. Like I'm one year in. If you're telling me I have to do this for another 40 years, I think I might just jump out of the 42nd floor, right? And so I ended up leaving and I remember that was actually my pivot point into HR. And it was really funny.
[00:22:37] I remember, you know, and again, in the spirit of like things that are, you know, getting really lucky, you take a step back and you're like, think through like, what limited tools do I have to be able to go and create value for another organization? And I was like, okay, time to go and pull out that, like that reserve shoot. It's like, I'm going to hit the ground, right? First shoot didn't work. Okay.
[00:23:00] And so my, my first foray into HR and I remember sitting in what I applied to like a ton of jobs. Like I just, anything and everything. And it's just like luck of the drawn who, who calls you back. Um, and one of the people that called me back was this, um, regional manufacturing company. It was like a pulp and paper company. Yep. And I remember sitting in the office of the HR director or like VP of HR, like the guy who ran the, the big kahuna that ran the program.
[00:23:29] Uh, and I remember psyching myself out. I'm just going to be like, I'm going to fake it till I make it. I'm going to tell them I know a whole bunch of stuff about HR. Obviously in my resume, I have no experience. Right. And so I go in there, I've got my talk track and I'll cue cards and memorize and practice in front of the mirror. I'm like ready to go. Right. Like the guy cuts me off midway through. Yeah. Stop doing that. Okay. Listen, you're not sitting here because you know anything about HR. So let's just let that.
[00:24:01] I'm just like, I'm going to get my bang jacket on and like see myself out. I don't like, I'm like never going to make eye contact with anyone from that organization. Um, and what's crazy about it is that he was like, I actually don't care about that. I care about the fact that you actually have an element of like analytical modeling experience and HR, right? Wow. We operate like one of, we have a lot of, a lot of unionized facilities. 80% of our firm is unionized.
[00:24:30] And like, it is a useful skillset to have on our collective bargaining team to be able to go and model out language adjustments as it relates to what it is that we are offering and like how to go and quantify that. Right. Wicked lucky. Practically speaking, I should have just bought lottery tickets. Oh, that was a good decision. Leading up, you made the choice. And your boss or the guy at the time, that's, that was wicked smart.
[00:24:57] Because, you know, kudos to him or her for making that, uh, or having that inside because it's, that, that's just smart to be able to go into that room with the negotiator and say, Hey, listen, we've done the math. Check it out. Make sure that you see the same thing we do. Then you don't have any rational expectations on the union side where they come in and go, it's up here. It's like, actually, let's, let's just look at the math. You can have the math too. Like that, that's brilliant.
[00:25:26] I mean, on, on their hand. But let's get to the real question here, John. How disappointed were you that you spent all that time preparing? And he said, dude, just stop talking. You got the job. Yeah. No, trust me. It was, it was really humbling. And I think that like, that's one of the things that, you know, I'll tell you that you apply to a zillion jobs. Oh yeah. Just like, just want something humble. Real fast. It doesn't matter. I'll get coffee, whatever. Just, I just want something.
[00:25:55] And I think that it's that piece, which like is actually a worthwhile process for people to struggle through. Like that, that, that cultivation of grit and just humbleness that comes out of like, you know, maybe I can create value. Maybe I can. And like, you know, everyone tries hard and that's just the cost of admission. Like, you know, I think that's really important. And so I, so the long and short of it is that I joined them.
[00:26:21] And I get put into this weird position where I'm like, way, getting to see way more about the HR program than any fledgling HR person should ever get. And so I ended up staying there for about four years. I, I, I, it was, it was actually longer than I anticipated. I thought through it. And I was like, I'm going to go to law school. I told them I was going to go to law school. They were like, oh, and again, in the spirit of getting wicked lucky, they were like, you know what?
[00:26:49] I happen to know that instant noodles are a core staple of your diet. We'd pay for an MBA. And so they, they actually, this was like a simpler time. They paid for my MBA and a Canadian MBA. So don't worry. It was wicked cheap. And so I ended up getting my MBA there, but also getting my foothold into like a core amount of HR concerns. And so that was, again, the one theme that you will see through here was wicked lucky. It was also the same moment that my parents did not understand what I did.
[00:27:18] And I have now, like I'm now on the, on the dark side of parental disappointment because like approval and excitement to your back to John. Are you an engineer, lawyer, doctor? Are you one of those? If you're not, what are you doing? What are you doing with your life? What are you going to do with that? What are you doing? The worst is at weddings when they're like, oh, this is my son, Matt. He's an accountant. And then they get to me and they're like, not sure what he does, but I think it's recruiting.
[00:27:47] He does something with the job. We're not sure. Anywho, my, your other son, our other son is really, really, he's, he's doing, he's really successful. Great. Right. So what did you do after the NBA? What was the bid after the NBA? Okay. So I got, again, I got crazy lucky. I did, I did a really quick stint in consulting for about a year. Yeah.
[00:28:11] Because I think everyone after you do, if you do an MBA, like management consulting, blah, blah, blah. It's either investment banking or consulting. One of the two. Pick one. Yeah, totally. Totally. You just, you just, you drink enough Kool-Aid. You go and you do it and like whatever. Yeah. So I got wicked lucky again. So like in the spirit of like, if you want to get hit by lightning multiple times, apparently that I'm that guy. So this is like 2011, 2011, 2012.
[00:28:41] I get this call from this organization called Amazon. At the time they, yeah, crazy. I'm like a small company. Most people don't know who they are. I'm still a nobody. Right. I'm like, I don't know. I don't know how they got my phone number. So I get this call from Amazon. They had not, they were starting up deployment into Canada. This is like a weird time at Amazon. They're not profitable. Right. Like they're not market dominant. I actually didn't even know who Amazon was. I thought it was a subsidiary of eBay.
[00:29:08] My mindset at the time was I'll come and talk to you because I've never been to Seattle. And that sounds like a free trip. Oh yeah. Oh yeah. And Seattle's got great stuff there. So that makes sense. Unbelievable. Unbelievable. Anyways, I guess again, they must've mixed up. I get the job. So I moved from Toronto to Vancouver and they tasked me with like, okay, figure out how to go and launch Amazon in Canada. Right. And, and there, you know, one of the things that happens with Canada and maybe this will be true.
[00:29:37] Maybe it won't be true depending on whether or not we become the 51st state is that people underestimate the complexity of operating internationally, even though it's only 150 miles north of Seattle. Right. Right. Yeah. And so, you know, for a portion of about four years, I supported the build out of Amazon from one facility to just, but by the time I had left, I think I had launched 70% of the Amazon facilities in Canada. Wow. Wow. Okay. Quick question.
[00:30:07] Yeah. Non sequitur. The difference between Vancouver and Toronto from your perspective. Vancouver is like, like Vancouver is like the chill version of Toronto. Like the only problem with Vancouver is that it's kind of like Aspen. Like nobody actually has a real job there. Either you like, you've made it and you move to Vancouver or you work for people who have made it. And there's, there's no real career. Cost of living is crazy high.
[00:30:39] So fun sequitur on that. There was this one point where when I moved there, I was like, oh, I should go and buy a house. And I was like, I don't know how long I'm going to be here for. I could have earned as much as I earned at Amazon, inclusive of RSUs. Had I just bought that house and did nothing else for the period of four years. So in the game of snakes and ladders, I rolled through all of the steps of it, but should have just caught that one freaking ladder and got across mines. Yeah. That was, that was wild.
[00:31:08] So I did that with Amazon. Probably. I think everyone has like a come up story. I got lucky. I got two solid come up stories. At the time, my wife was doing a postdoc. We were still eating a lot of instant noodles. It was like, we've got to go get a job, like a real job. But she, but she got one of the jobs that's supposed to be gotten. So she was on the path. Yeah. Yeah. So at least you could point to her and say, oh, my wife's a doctor. Yeah, we're good. Not a useful doctor. She's a biochemist. So.
[00:31:40] Sounds smart. So that's good. No. So you can explain that. That sounds like something you can quote about, right? Right. Right. So. You don't even need to explain that. My wife's a biochemist. Oh, shit. You know. Legit. Yeah. What do you do? I'm a recruiter. It doesn't matter. I'm staying home with the kids. Yeah. Yeah. That's what I do. But that's, that's my, my target job. So we went to the US in 2016. Kind of continue the Amazon story.
[00:32:10] There was like a lot of buildup that was taking place in the Northeast. I was lucky enough to get some really large facilities. So like, I think the largest one I had was like 5,500 people. Like a small town of like just employees. Wow. And it taught me a lot about operating at scale, the value of standard work, scalability, and like really operating within like a big tech environment. I did some work within analytics, which was really nice.
[00:32:39] So like labor modeling for like hundreds of thousands of people, which is like crazy when you really start to think about what that means from a scaling standpoint. Again, I got really lucky to be able to go and get moved down to the US. We've been down here since. And then one of the things that I learned towards the end of my time at Amazon is that I think that the things that made me most excited about Amazon in 2011 started to give way to like, you know, they were big and mature and like really focused scaling.
[00:33:09] And, you know, there's a moment of introspection of like how much do I actually enjoy what fills up my day. And I realized that like I am inherently like an earlier stage person. I like building and thinking and breaking things and like, you know, to the point of like some of the conversations we had about like building for like furniture and stuff. I like putting stuff together, even if it's a bit janky. Right. And so I ended up electing to leave Amazon in 2019.
[00:33:39] And then COVID hit and Amazon stock price went up to a zillion dollars. Probably wouldn't be having this conversation if we just held on to my RSUs. Oh, yeah. Oh, yeah. Oh, yeah. But I had a chance to join like a fintech firm. I pivoted back into that. This time investment thesis of where I play best, which is like series C, D, E and accident IPO.
[00:34:07] And that's just that opportunity to be able to actually build stuff versus and I think that there's like a mindset element of either you're a builder or you're a janitor. Right. And I would like hate janitorial work. I'd hate the idea of just like every day's Groundhog Day. And I was just like, give me some DeWalt tools and let me go and build some janky stuff. And what does that happen for you, though? So in these roles, when did that start to happen?
[00:34:37] Is it the amount of time something's just something changes in the workforce or you've gotten to a level of build and you're like, all right, my job's done. And you get bored and you move on. Monotony. Yeah. It becomes the same. I think that at Amazon, like it creeps up on you, right? Like suddenly, you know, the idea of being able to operate, you know, you become in large organizations, there's a tendency to become narrow and deep, right? Right.
[00:35:05] And, you know, suddenly it creeps up on you. Like, whereas, you know, when I first joined in 2011, 2012, I was literally a janitor. Like I would push the broom around the place and like tidy stuff up and like, you know, whatever needed to be done, I would go and do. Towards, you know, you have like a scaled team. There's like 40 people on your team and you are now just like air traffic control for like just landing airplanes.
[00:35:33] And every day is another day at JFK and you're going to land 190 airplanes during your eight-hour shift, right? And like that's the process of like, you know, again, it sneaks up on you because first it's like you got to land airplanes. But then your job becomes narrow and deep where all you do is you talk to pilots and you land airplanes. And so I don't know. It's funny. So for the last couple of years, I've been operating within the fintech space. I joined a company called Revoluts. I joined them quite early on.
[00:36:01] I think when I joined them, they were at like a $550 million valuation. It was just a bunch of like vest-wearing tech bros trying to like rewrite the invisible rules of money in New York. And so spent about two and a half years there. That was really cool because, again, in the spirit of getting lucky, that company took off. They did really well in Europe. So when I joined them, they were just entering into Series C.
[00:36:28] They did a raise at $1.7 billion, $5.5 billion. And then they did this massive leap to like $30 billion. Their last raise was like $45 billion. And so like, again, that journey of like build really fast to be able to facilitate scaling. Right. Which is inherently very interesting. I was then, you know, I got pulled to a broker dealer. Think Robinhood, but for Europe. The name of the company was eToro.
[00:36:57] And the thesis there was like, get us mature so we can SPAC. And then the SPAC market blew up. And so you get to use a slightly different skill set of like, oh my God, how do you keep the lights on? The door is open. So I did that for a couple of years. And then a couple of years after that, I got to daily pay. And again, I think the daily pay is probably, you know, smack dab in the middle of that standard thesis of, you know, when I joined, you know, about a year and a half ago, we were still, you know, lots of stuff was breaking. And we're still trying to figure a bunch of stuff out.
[00:37:26] But like very focused on like, hey, by the way, like whip out your sawzah and like, let's go and like build some janky shit. Right. Let it work. It's like, yeah, again, it's this idea of being able to go and build and to move the needle and have like something that's tangible. Is it like world class? Maybe not. But, you know, it is like there was no table there. Now there is a janky table there, but at least something that we can start to iterate on.
[00:37:52] And I find that so rewarding and so engaging as it relates to actually having to think through something. It was like, hey, by the way, like we need a table. So like get your pickup truck. We're going to Ikea. And then you have to follow the stick men to try and put it together. Like hate that. No, I fail there every time. Last question for me is what type of personalities are people that thrive around you? What do you need around you? You know, it's it's funny.
[00:38:21] I was actually talking to one of my colleagues about it recently. And she was like, you know, I think you want X, but practically speaking, you really need something else. So that that that I think. So I'll put a caveat on this on this, which is there's a very real possibility I'm wrong. So I think the people that thrive around me are outside of the box thinkers that are inherently gritty and focused on moving the needle. Right.
[00:38:50] And are they starters? Are they self starters? Self starters. Yeah. But one of the things that I think that I've realized, and this is, again, one of the reasons the statement on why I'm putting an asterisk on this and is that I also think that you can have too much of that. Suddenly, suddenly you just have the hot lodge, like fruit salad of like things that die in the backyard graveyard of unfinished projects. Right.
[00:39:18] And so more and more, I realized that there is a there's a balance that needs to be hit because if you have too many dreamers, nothing gets done. And so I will say that, like, it's one of the things that I'm working on myself on, like having a deeper appreciation for the fact that, again, that it takes a whole bunch of skill sets. And there is merit within a lot of those skill sets beyond the things that I view as being core. That's cool. Core to who I am. So. Yeah. Yeah.
[00:39:46] John, last question from me outside of your background is about people. Yeah. I've been studying and reading a lot on where people thrive and where they don't thrive. Sure. So I want to get your perception as a people officer, chief people officer, where do most people fail? Where do most people fail? Say more. I feel like people fail a lot everywhere.
[00:40:16] Yeah. Yeah. Where do they maybe where do they let themselves down in the process of growth from college through the journey of of a career that maybe has no direction? Right. And they feel lost. But where do they fail in in not making a pivot or not continuing on? What's your view on that? Yeah. I think that every day is a grind. Yeah. Like, don't get me wrong.
[00:40:45] I wake up most days and I'm excited about the day. But, man, there are days where it's a grind. Yeah. And I think that it's life in a career can be death by a thousand paper cuts. And so the timing on that question is actually very apropos. It's January 15th. This is like a really good opportunity to take. I think that people don't do enough retrospectives, like really silver retrospectives where you take a good hard look at, like, what you've gotten done in the last year.
[00:41:15] You give it a rating from one to five. You give yourself a performance. Like, you sit down with some Jack Daniels and you just, like, have a silver conversation with you. Right? One. One performance improvement plan. Right? There's a secondary piece to it, which is that I think that the question then becomes how do you become more deliberate about what you do in the following year? Intentionality. Yeah. Intentionality is, like, one of those things that, like, to engage in intentionality, you have to be intentional. Right? It's like.
[00:41:45] Right. It doesn't come from nowhere. Right? But, again, I think that that element of retrospective, really silver look at, like, what did it, like, based off of what I want to get done, do I get it done? And then being really deliberate. Deliberate. And when I say deliberate, it's like really being clear in your own mind of what it is that you want to go and pursue. Right? Right. And then making. You might change once you get to that place. You might get to that place and go, okay, yeah, let me do this other thing. That's fine. Oh, heck, yeah.
[00:42:14] I mean, and that was my experience. I got into KPMG, like, top-tier accounting firm. I thought that's what I wanted. Freaking hated my life. Yeah. Like, no offense to KPMG. No, no, no. Great people. Great people. Again, that element that, you know, what it is that you want and the iteration and synthesis of who a person is and what it is that they value, it changes over time.
[00:42:35] And so, again, I think that the one thing that keeps people from getting stuck is one, internal accountability, which is like, again, taking a retrospective. Not of like yesterday or last week, but like in a meaningful timeframe.
[00:42:48] And then really being deliberate about, like, what you want to go and tackle and making sure that wherever you are, you're paying yourself first and you're making sure that there's enough reciprocal value being created by that organization to be able to go and make it worth your while or that pursuit that you are on to make it worth your while. Drops mic. Walks off stage. John, this has been wonderful. Thank you so much for your time. Thanks for coming on the show. I know the audience is going to love it. And also for the audience, thanks for listening.
[00:43:18] Until next time.