Today, we are joined by Ryan Harrington, a seasoned startup investor, advisor, and product manager specializing in financial technology. In this episode, Ryan shares his incredible journey from a private wealth analyst at JPMorgan to becoming a key player in the NYC tech scene. Learn about his extensive experience, including finding product/market fit, defining roadmap strategy, and aligning development teams to maximize output. Discover the impact of digital transformation on the financial industry, the real-life responsibilities of a product manager, and the future of FinTech.
Ryan is an expert in financial technology, with years of experience in both early and late-stage tech startups. As an advisor and investor, he has helped numerous companies navigate their growth and development phases. Ryan offers insights into the challenges and triumphs of navigating tech startups and the evolving landscape of FinTech.
What you’ll hear in this episode:
- Ryan’s transition from private wealth analyst at JPMorgan to tech product manager
- The impact of digital transformation on the financial industry
- The real-life day-to-day responsibilities of a product manager
- Insights into effective product management strategies and planning
- Lessons from Ryan’s journey and his approach to early-stage investing
Comment your thoughts on Ryan’s journey and insights into the future of FinTech.
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LinkedIn: Ryan Harrington
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The Evolution Of FinTech: A Conversation With Ryan Harrington | LeverUp® Podcast [Season 1 Episode 9]
Sitting down with Ryan Harrington. Really excited to sit down with you. You have a really interesting career. You went from being a private wealth analyst over to the tech scene, and now you’re a product manager in tech. There’s been a lot of really interesting commentary around the product manager role in the last month based on some TikTok videos. Anyway, tell me a little bit about yourself first.
Super high level. I was a finance undergrad. I left undergrad. I went to work in private wealth. I was at J.P. Morgan. I had interned there, went back full-time. It was a great job. It was a great place to start, and you get to work with a lot of smart people. It just wasn’t for me. The thing is, there’s a lot of digital transformation happening across capital markets. Fintech is all over the place. It’s in wealth tech, there’s capital markets, there’s all parts of it. It was all coming to my desktop, is what I’m trying to say. I was seeing cool things that I wasn’t a part of, I was a user of, and I was having an existential crisis of what I wanted to do anyways. That’s a great combination to then pivot to tech. That’s exactly what I did.
I went to a startup, very early stage, was there through an acquisition, all the way through to the late stage. I’ve seen and touched a lot of things across tech as an operator, always on the product side. A lot that I can point to and talk about there, but before I do, I know you’ve got a surprise teed up for me. This is the part where I get hazed a little bit on air. Let’s see it.
The Daily Life Of A Product Manager
I do have a surprise for you. We’re hearing a lot about the product managers and what they do as their personal day in life. I’m going to play two product manager videos that have gone viral over the last three months. Here’s number one, A Day in the Life of a Product Manager at Microsoft.
“Welcome to a day in my life as a product manager at Microsoft. I started around 9:00. The first thing I get when I get into the office is a latte from the baristas at SVC, and as we see, I miss this office so much. I work on the design that would later inform one of my later meetings. I filmed some content for a Christmas video that my team was putting together. At 11:00, I spoke with the designers about that work that I had done earlier. Part of my team is in the office. I don’t get to explore this campus that often. It’s so pretty. I did some work on deep learning and met up at 3:00 with one of my intern friends from last year. I headed home around 4:40. Bye.”
You start at 9:00?
If I’m lucky. If I’m late. Where’s my barista?
I know, we need a barista.
I got the bad end of this deal. We must have missed that part where she did that work earlier.
She did some work earlier. I did this work earlier.
That’s inferred.
I know, of course she did the work.
4:40, they’d be looking for me.
At least she’s in the office. The second one, and I think it was Net Capital Girl that said the next video is going to do for product managers what Top Gun did for Navy Recruiting.
Totally.
Anyway, so here, I’m going to play the second one. We got another minute, but this one was the most hallucinating for me.
“My coworkers keep saying I need to make a tech TikTok. Because if you look at my TikTok, you’d never guess I have a job.” I wonder why. That’s crazy. “Anyways, this is our current workstation. Callie and I are what you call product managers. Callie, what is your team over? My team is over recording and internal tools.” Should’ve thought about that. “I am over what we call card experience. We work on anything from activating your credit card to freezing, reissue, shipping, all the good stuff. What’s a PM?” I don’t even know.
This might be the cringiest thing I’ve ever seen.
It’s so hard to watch. I’ve never got three in one sitting. “You know what to build so that you have the product to use. Exactly. You might have a team, like the engineers actually do the developing, the coding, which is the impressive part. Designers also do the impressive part, which is everything you see when you’re in a software. Product managers essentially decide what the team’s going to work on, do competitive research.” Gaslight. “Prioritize bugs, keep it focused.”
That’s what they do. They gaslight the development team.
It’s crazy. “That’s what we do. We work from home, which means you work from the internet.” Or you don’t. “Thanks for tuning in. I hope all you coworkers are happy. I’m branching out into the tech niche.”
Now that we’ve recovered from that atrocity, what does the real day in the life of a product manager look like? What are you actually doing? What time do you get up? I want to know the nuts and bolts of something that’s actually added value.
100%. Here’s the thing about this because I’ve seen these videos. That video is not new. It came out in 2021. Correlation versus causation. Not long after that is when a lot of big tech layoffs started because rates started going up and people had to start being responsible, but you can point to that and be like, that was really apocalyptic for a lot of people. Part of this is like, if you’re working on a big tech consumer platform where the value already exists, the product market fit is already there. The customers are sticky. Say you get the majority of revenue from a very legacy business that you’ve monopolized. I’m not going to call any names out Google, but you can afford to hire big teams like that and wave in the big talent.
You’re a PM, you’re a developer, blah, blah, blah. Put everyone together and be like, we don’t have anything ready to go yet, so go play outside. That’s how you end up in a situation like this versus where I am, which has been early-stage B2B SaaS, specifically in FinTech, where we are coming in, we’re solving a specific problem in financial markets. We have competitors. Our clients are super sophisticated and have high expectations because they’re using other technology solutions. We have to be on the ball, and we’re going to develop a new product in addition to maintaining an existing one. We have to really split our time and be really efficient about it.
We ultimately try to be the leaders of, like, where is the business going? What is the story? How do we get ahead of it? And how do we translate that to something that a developer can build a solution for, that we can take to sales, who can sell, find out if we did it right or did it wrong, and iterate. That’s the high level. I’ll go so much more granular than that, but my initial reaction to something like that is, if you’re not actively solving problems, then you’re going to go to the pool. Because that’s our job, and if that’s not what we have to do all day, then that’s how you end up in a situation like that.
Incremental Improvements
What I’m hearing you say is that is a better example of a late-stage product manager. Not to say that their role is check-the-box, but that their role is more incremental. Does that make sense? It’s, like, incremental improvements at best. Walk me through. I want to get as deep as possible.
Totally.
7:00 AM. What are you waking up? What are you thinking about? What are you thinking about when you go to bed?
100%. For me, I have always owned specific products, and especially being in early-stage tech, I’ve taken products from being on paper to in an MVP state, to on someone’s desktop, watching them use it, figure out if we did it right. For me, when I wake up, and I’m getting ready, and I go to the office, I already know what my checklist is on a quarterly basis, what our firm’s guidance is for the next three years, and what I have to do to accrue to those things. I put this in the playbook as well. The real goal of a product manager is the firm has these top-level KPIs. We want to grow revenue this way. We want to enter this market. We want to go international. We want to penetrate this channel and kick out the incumbent.
We have these things we want to do. We have salespeople who want to get in front of the clients. We have developers that want to work on tough problems where they feel stimulated. My job is to align everyone around those things in a way that fits those long-term goals. We want to grow in the international channel. Great. I have a roadmap for that. This quarter, here are the ten things that we’re going to do that we think are going to accrue to this, which means I’m going to talk to these potential users. I’m going to talk to these sales stakeholders. I’m going to take that feedback. I’m going to write it all down. I’m going to socialize it. I’m going to go to legal and see what we can do.
I’m going to talk to our tech leads and see what we can do. I’m going to break that down to individual tickets of, today this guy works on this. Tomorrow, this guy does this because of this. Get to the minimum viable product, which is what we live and die by, and we can talk more about that. Get that out the door, track the data, see if we were successful, and if we weren’t, no problem. We fail all the time, but we fail quickly and unemotionally, which is critical. I’m never married to the results. I am married to this thing works for me, and if it’s not working, we’re going to move on. Get it out the door, and then move on.
We fail all the time, but we fail quickly and unemotionally, which is critical. Never get married to the results. Share on XLeadership Challenges
Give me an example of leadership coming to you with a specific challenge, and give me a real-world specific challenge, and how did you dissect that problem, and how did you get that to, because a little bit of translation between executive and customer into developer-speak, for lack of a better word. Walk me through a specific scenario, because I want to see, because I laughed at the videos too, but I know that’s the 1% edge case of what you guys do.
Totally, and they ruin it for the rest of us, but the reality is, I am the guy, the buck stops with me. The business says, we want to take our product that’s successful in the US, we want to use it in the UK. We’ve never done business in the United Kingdom before. This is a hypothetical, by the way, but we want to go to the United Kingdom, to which I would say, great. I have to think through everything about, and everything, by the way.
The legal ramifications.
The legal ramifications, the user behaviors, how does their market work? When do they do business? If you were to go to Portugal, they’ll take a siesta. In LATAM, they’re more decentralized, and I made big players in the spaces that I’ve worked. Do we change to a more consumer-type model? How do we handle time zone changes, especially in fintech? If you’re at all transaction-oriented, time zones matter. What is the user’s experience when they come to the platform? All of that kind of stuff. Our data feeds. We get data in the US from 9:30 to 4:00. If you’re doing something in markets, but in the UK, that 9:30 to 4:00 Eastern doesn’t work, so do we have to change vendors?
Do we have to ingest it in a different way? Somebody has to literally ask all these questions. The thing that I’ve learned from being a product manager is nothing on the screen is an accident. It’s all intentional. Somebody has thought through the color of every button, when you click on it, why you’re clicking on it, what journey you are going on, and what we can do to keep you engaged in a way that we’re going to add value for you so that you can add value back to us.
Shaping Customer Journeys
You said the word journey. One of the things I talked about when I was in consulting was a customer journey. Double-click into that. What helps you shape those decisions to make the journey? Obviously, the font color is an output, but how do you think about the customer journeys?
We do a lot of what’s called user experience research and design. This is a mix of qualitative and quantitative. The qualitative is, I talked to sales, or I talked to a prospective client, and they told me a story. I want to be able to do this. I want to be able to do that. We will start literally going to a whiteboard. These are some of the highlights of my career. It’s like being in a room with all my guys and whiteboarding it out. We will start to talk. If he comes in, he finds this. How do we show it to him without being too aggressive? How do we get him to click on this? Because it’ll take him somewhere else. As we start to build something that does this, the initial iteration is not going to be the shiniest thing in the world.
We want to prove a concept as quickly as possible. We will track the data behind that journey. What I mean is, we will track click metrics, we’ll track user sessions. How long were you in here? Did you do what we wanted you to do? Did it take you a while to get there? Did you leave? Did you get frustrated and leave? Technology today, a lot of the tools that we use, have allowed us to break into that and actually see, so-and-so got this far before they exited the platform. They still did business, but they just did it away from us. That is critical for us to understand so that we can patch those holes in the ship and keep it up.
Success And Failure With Features
What’s a good example of something where you put a feature out and it had amazing uptick, and then give me the counterexample of where you put a feature out and it crashed and burned.
I don’t even know where to start on both of those. I have tens in each direction. There was one feature that I put out that was solving a data integrity problem for a lot of our clients. Because a lot of the platforms that I’ve worked on have been very data-intensive in what they’re giving to the end user. We have to get that data from a lot of people, and that’s hard. Because data comes in different formats, people have different ways of doing it. When you’re asking people to send you things systematically, you’re asking them to do work, and they’re like, hang on, you got to fit into my roadmap. Suddenly, we’re going head-to-head on something.
We want the same thing. I had built a feature that allowed us to get data more succinctly from a UI solution. Instead of needing a bunch of engineers to do it, a human who knows the business could go and be like, they want this from me. If I give it to them, it’s going to help me do business with them in a way that accrues to my bottom line. I’ll give it to them this way. Great. We built a not-shiny solution to do exactly what I just said. Not shiny is an understatement. It was basically a box of rocks on the screen, but it got the job done. It was more efficient, and people loved it. We’re like, we’re going to invest in it. We’re going to clean it up, and we’re going to make it faster. We’re going to do all this stuff. That’s the best way to do it.
You have to divorce yourself from the product. Because I thought it was a good idea, but I’m not going to know until I see the numbers. Versus my next story is I thought this was a good idea, and then we put it out there, and it blew up. You can’t cry about it. Because stuff is going to blow up all the time when you’re a PM, and you just move along. You keep thinking about the North Star. My next story on this is, I’ve put out features where I’m like, I have an idea for a user journey that I’m going to create. I know that so-and-so wants to go from A to B. They’re going this way. I can shorten the journey by introducing this button in this area, and we’re going to track it.
As a product manager, you have to divorce yourself from the product. You can't cry about it. When it blows up, just move along. Just keep thinking about the North Star. Share on XIt’s going to be faster. It’s going to be slick. It’s going to give them all sorts of, like, these guys are so smart. They’re thinking of me, but I was thinking of it from my perspective, and I was wrong. I put this feature out there, and I didn’t socialize it enough. I didn’t go through the proper product methodology that I’ve laid out. As a result, no one even ended up finding it. They’d find it and get frustrated. I was like, I’m not even going to try to save this. We have better problems to solve, and you just move on. It’s critical.
Career Transition
Let’s take a step back. You started your career out as a banking analyst in high net worth. Talk to me about that role. There’s a lot of people that tune in that are interested in, like, I want to break into finance. They’re probably college students. Talk to me about that role, and then with the inflection point, you did it. What made you pivot over to tech?
100%.
Talk to me, walk me through that, and take a lot of time to do it.
I for sure will. I started getting interested in finance back in high school. I actually had a really cool personal finance teacher who was, like, the man, like a super young guy.
Amazing. We need more of that in America.
I couldn’t even believe it. Super young guy. He had been a commodities trader, had made a bunch of money. He bought a bunch of real estate. He goes to become a high school personal finance teacher, which is not where you saw that story going, right?
Absolutely not.
Me either. Even at sixteen, I was like, “What are you doing here?” He said to us, “I don’t have to be here. I made all this money. I own all this real estate. I could be on the beach. I’m here because I want to be. I am completely independent. I want to impart knowledge on you guys. That’s why I came.” I was like, “I want to live like that. I want to be like this guy. Should I study finance? Should I be this self-sufficient?” That got me, like, through the door mentally. I go to school, I study finance. I get an internship, luckily, at JP Morgan Private Bank. I was so unqualified compared to my cohort. I walked in, and I was like, I can’t believe I’m even here.
Something tells me you talked yourself into that internship.
It’s how I talk myself into this room. I’m a big storytelling guy. They’re like, you must know things. I was like, you’re going to be so disappointed. But so I show up, and I’m like, I’m going to keep this ruse going and ended up having a great experience. Interned, joined back full-time, worked as a private banking analyst. I was on the desk. I was working with bankers, investors, really sophisticated clients. It was a great experience. You can grow up in that world and be so successful. Some of the bankers who I worked for, they’re covering these brilliant clients. They’re doing interesting work. They’re making a ton of money. Everybody’s super happy. I’m like, I should be so lucky to ever be as cool as this guy is. But where my head was at was it just wasn’t for me. I wasn’t as stimulated by it.
What was bugging you about it?
Nothing was really bugging me about it. You know what it was? I would look at my boss, who, again, was super successful, very happy, and everyone respects him. I’m just like, I just don’t want your job. I don’t want to deal with the things on a day-to-day.
What was he doing? You got to tell me more. What was he dealing with that it was like, that’s not for me? Because you have way more headaches than a private wealth manager has.
That is for sure. I know.
You have way more headaches.
I’m like, what was I thinking? I’ll give you an example. When I was there, we were dealing with their family office. We’re talking about guys with hundreds of millions or billions of dollars. They’re going to say jump, and we’re going to say how high, and so that can get a little bit old. There was one guy who called us to roll a bunch of T-bills, which is an operational thing. We’re talking about tens of millions of dollars’ worth of T-bills, but he was like, I’m not paying the commission on this. I do so much business with you guys. I’m not doing it. Do it for free, or I’m doing it with Goldman. Those are the kind of people we would start to work with. I was like, and of course we did it for free because, like, he’s right. He’s completely right.
He’s sophisticated. He’s going to know this, but that was the type of stuff that I was like, I don’t know if I can do this at scale. Some of these guys can. I give them all the credit in the world because they’ve built amazing businesses, but it just wasn’t for me. But it is for other people, and I’m not going to discount it at all. This is not a “don’t work at JP Morgan” thing. Please do, if you could be so lucky. It was great for my career, but as that was happening, I was taking a really big step back and thinking, what do I want to do? I started looking around the bank. Do I want to go into investment banking? Do I want to go into markets? I’d be blessed to get any of these opportunities, but I then took a lot of time to think about what’s interesting to me.
Honestly, not just like, I should go do IB because my friends do IB and they’re making more money than me. I removed myself from that mentality and was like, what would I get super stoked about when I’m in the shower in the morning to go solve? What am I going to think about before I go to bed, like, I’m so excited that I get to be the guy who takes care of this and the world’s a better place to some degree? My head landed on tech. The reason was what I alluded to earlier. All these new softwares were landing on my desk to make my life easier. I was like, who built this? Who came up with this? This is so good.
I can do that.
I was like, I can do this. I know the problems that I have. I would love to build something for me and then watch the next Ryan Harrington go use it and be like, this is sick. I was like, what is that? What’s up? I didn’t know what a product manager was, which is hilarious because I am one. Three years ago, four years ago, I was like, what is this concept?
You watched some TikToks, you figured it out.
I was like, I just go to the pool. This is great. They make coffee. But so that got me interested in it. There was a startup that I was looking at. I had used one of their products, and I was like, this is sick. It was on my desk every single day, so I was the user. I was like, I should build for me. There’s no better example than, like, this thing that was built for me. So I reached out, managed to get a job there.
So, you reached out and sourced your own job?
Yeah.
Keep going. Unpack that. You got to unpack that.
You absolutely have to. If you think about it, if you throw your resume down the resume hole, good luck. Honestly, luck is all that’s on your side. If you have a story to tell, people love stories. If you can reach out to someone and be like, I’m using your product. I really enjoy it. I would use it more if you did this. I have feedback on it, but also, I can help you with this. I can help solve this problem. That’s what I did, and that fits the bill because there’s immediate value.
That doesn’t hit the recruiting pipeline mentality. I will check the boxes. I’m a target school. The problem with that is uncertainty, and no one wants to be in an uncertain world. What do you do to manage that? What was your hit rate? One for one? Did you say that to three different people?
No, it was terrible.
You walk into the actual process. You’re telling me the victory story. Tell me the struggle story.
I’ll preface this with one of my favorite quotes, Peter Thiel being like, “Competition is for losers.” That’s how I approach this. Where I’m like, I don’t want to just apply for jobs. I want to stand out. This is something that I’ve done, which I’ll tell you another story on this as I’ve been trying to expand my career further as an investor. I would LinkedIn message people, and I wouldn’t even expect a response, but I would have something ready to go, and I would send it out the door. I’ve made Excel trackers of people. I’ll spend more time finding people to reach out to than actually reaching out. I’ll put together the tracker and be like, they work at this firm. This is what they do. This is our connection.
I’ll have a canned thing that I reach out with that I’ll tweak based on the notes in the tracker, and then I’ll go out, and I’m just going to start hammering them. Most of them won’t respond. I’ll give you an example. I’ve been doing a lot more work on the investing side personally, and I’ve had some opportunities come up for me in that world. One of the ways that I’ve been able to get in front of people is I’ll send them a deal. Because I live in New York City, I’ve done private investing myself. I have my own small nascent pipeline of deals. I will get one in the early stage, and it’s someone who I know who wants help raising anyways.
They’re like, talk to anybody who might know about this, and my LinkedIn outreach will be like, I saw your profile. I think it’s really interesting what you do. I’d love just to pick your brain. By the way, here’s the deal that I’m looking at. They’re raising. Here’s why I like it. Check it out.
I get those mails. People send me that, “We got a deal for you, pre-seed round,” and it never lands on me.
Why not?
I don’t really know. It doesn’t land on me, but what I heard you say that’s different is you’re like, “Can I talk to you? And also, I have a deal.” It’s like they lead with the, forgive me, the black, better word. There’s no foreplay, they just lead with that. Here’s the deal.
Guy like me, strictly business.
Strictly business. It’s like straight to the deal. I’m like, delete, archive, really quickly. How many cold mails do you send out on LinkedIn a week?
It depends on the time of year or where I’m at, but when I was doing this more aggressively, a little bit more back in the day, not as much recently. I’m very happy right now. I could build a tracker over a couple of days of 50 people that I want to hit, and then I’m going to go ten a day, Monday through Friday.
But you’re always doing this?
I’m always doing this.
You have a full-time job, and you’re still always doing this.
Your full-time job is to get another full-time job, even if you’re happy where you are. There’s a saying from literally Sex and the City that is totally true. I’ve never even seen the movie, but I still agree with this, everyone in New York is looking for at least one of the following, which is an apartment, a relationship, or a job.
That’s beautiful.
It is. I can’t say this enough, I’ve never seen that movie, but it’s a great quote. It’s a great quote. I look around, and I’m like, all my friends who are like me, who are super ambitious and doing well, but always want more, same thing.
Same, same.
Same, same. Every single day. If you have a job and you’re happy like that, it could still be taken away from you. You got to stay competitive. Stay networking.
If you have a job you are happy with, it could still be taken away from you. You have to stay competitive and keep on networking. Share on XYou’re ten a week at least?
Yeah.
At least?
At least.
Is there ever a week when you don’t send a cold mail?
I’ve not been as much recently.
Tell me why.
I’ve been happy at my job. I’m like, I hope they see this, but I’ve been happy. I have great opportunities. I’m not looking to really make a move. When I was younger and I was trying to jump into tech land for the first time, when you’re asking somebody to take a chance on you, I’ve hired people before, and I see someone who this resume kind of looks like mine did. But honestly, I’m not in a position to take a risk. I need somebody who can come in and work because we’re busy.
If I’m going to deviate from that plan and take the risk, I need to be sold a little bit. If they can sell me a little bit, then I’ve always said that, like, people who have reached out to me with a compelling outreach, not just like, “Ryan, we saw that you’re hiring, and I’m a grad student.” I’m like, I’ll file that one away. But if I get something creative, or there’s a joke in there, it could be anything. You can be a good one-liner in the opener, and I’m going to be like, I want to talk to this guy. Maybe he’s cool. It’s just that simple. People are people at the end of the day.
You’re not looking out, you’re happy. What would it take for something to hit your desk for you to reevaluate what’s going on? I’ve been in a situation before where I was happy in the role when I was in McKinsey, and then suddenly, I get an inbound, and I’m like, this is different. It’s a game changer. What does it take for you to reevaluate things?
You know what it is for me? The reason I love being a product manager is I love solving problems, especially if it’s for the first time. I’ve been working in FinTech for a few years now, so in our little space that I’m in, I do know it well enough. I’m not the best, I’m not even close. But I’ve learned a lot about it. If there was an opportunity to do that again from scratch and be challenging, I care more about the challenge at times than I do about the compensation. If this works out, we’ll make a bunch of money, but upfront, you might even take a pay cut. If it’s a hard enough problem and I can be stimulated by it, I could sink my teeth into it and do 80 hours of me just thinking about this.
When I’m thinking about the problem in the shower, I’m happy. Honestly, that’s a good barometer for a guy like me. If it’s that stimulating that I’m going to bed and I’m waking up and I want to make this better, and I have that, that’s why I’m where I am. That’s what I’m always looking for. The day that I don’t have that is a day that I’m going to be sniffing around.
Investment Strategy
You’ve got some side investments that you’ve seeded. Talk me through, what does your investment buy box look like? What are you interested in? Whether it’s in FinTech or something else, walk me through how do you evaluate an investment and what’s interesting?
Totally. For me, I’ve only ever done early-stage investing, and that’s very intentional. I’ll tell you a good story on how I got started in this because I was like, “I’m ready to start investing in private companies.” A lot of this is like you’re just in the right place at the right time. Here’s a good one for you. I’m at the office, two seats down from me is this guy named Ha. Ha’s a quant engineer. He’s our head of quant. He’s one of the smartest guys I’ve ever met. He was a big mentor to me early on coming into tech. I have nothing but good things to say about him. This is a guy that wears sweatpants and flip-flops to the office every day, and that’s fine. He’s so smart that we’re like, “Dude, you can come in with your pajamas, keep solving the world’s problems, and we’re happy.”
Whatever you want to do.
He comes in one day in a full suit with a tie. I’m like, “Ha, who died? Are you going to a funeral? Are you interviewing?” I know something is going on. Something’s afoot. This is not another day in paradise. He’s like, “No, I’m going to a prospective investor event. You should come with me.” Because we had a close relationship, I was like, “I would love to. I got to go home and change, clearly, but I will absolutely do that.” After work, I go with him to this event. It turns out the guy raising money is a three-time entrepreneur, the founder of Omni Labs, which I ended up investing in. Three-time entrepreneur, had sold his last company to Google, has a PhD in computer science from Stanford, he’s checking all the founder boxes.
I had looked at the actual company as well, which I did, but he’s checking a lot of boxes that are upfront. I’m like, “This is very exciting. I can’t believe I’m in this room.” Turns out this guy, the founder Thuc Phu, is from Vietnam. Ha is from Vietnam. They went to high school together. To be in New York City at the same time, how small does this world get? I’ll get to the point on this. When I’m there, I meet him. I get the financials to do my own diligence. I’m looking for things at the early stage. Mostly it’s like, what’s the burn? Are they raising money because they need to survive, or are they raising money because they’re growing? That’s the number one thing.
A lot of the rest of the model is just forecasting because their revenue is nascent, and it’s usually concentrated to four or five buyers. There’s just going to be a lot of risk in the model. You have to hope that the guy is going to be able to take you away from the concentration, reduce his burn, and actually grow the business. That’s what you’re hoping he’s raising for. If you can distill that all out and get comfortable with it and get comfortable with them, which I could pretty quickly because I was like, this guy’s done this three times, fine. That’s a bit of an example. That’s what got me to go forward. The bigger thing for me was being in that room. Because with early stage, you want to just get access to things. You want to know what’s going on.
I have friends who are institutional-level investors. They work for big VCs, and they focus on early stage, like pre-seed through Series A. They’re like, “The number one way that I can add value to my team is not just being the best at Excel here.” Because everyone’s good at Excel. They have an investment criteria. I’m just trying to solve those. I’m trying to answer questions for them. It’s sourcing. The more you can network, the more you can plug yourself into an industry. I’ve learned, I’ve done a lot of generalist approaches to this, but I work in FinTech. People want to hear what I have to say. I can get in those rooms, offer an opinion, and suddenly there’s, “It’s valuable to know this guy. We should call him when we’re raising. We’d love to have him on the cap table.”
Is that for your personal account?
Personal.
FinTech And Investment Management
It’s for your personal account. You have a view on FinTech. What role do you see FinTech playing in investment management? We hear a lot about, “Is AI going to disrupt the P associate? What is FinTech going to do to private equity, to venture capital?” As far as the whole co-side?
Yeah.
Is that a good thing? Is it a bad thing? What’s going to happen there?
I think it’s a great thing. I’ve been hearing this for years, and I don’t remember who first told me this. I think I heard this, it sounds like JP Morgan. The AI is not going to replace people. It’s never going to be net destructive. We’ve talked about this.
AI is not going to replace people. It will never be net destructive but would move people to better things. Share on XNever destroyed a single job, never been one job.
It’s moved people to better things. We don’t have people lighting candles on the street anymore. That’s a good thing. AI is the same thing. We’re just going to turn one guy into a superhuman. A product manager in general faces ten engineers before he runs out of capacity because then you’re spending all your time having to manage people as opposed to finding the next problem to solve. With AI, it’s like, maybe you can have fifteen, and those fifteen are twice as good. In the tech side, that’s why I think about it. In investment management, it’s even better. There’s a girl who I met who you would actually really like, and you should probably have her on. She’s in Y Combinator. She was a friend of a friend. I met her right before she got in. I was actually there two days before she got the call, side story. She’s in Y Combinator with her company, and they’re doing AI-assisted due diligence. They’re literally calling it analyst as a service, but it’s not supposed to replace your analyst.
It’s supposed to just empower them to, like, “I need to build this model. Here’s the assumptions tab.” It’ll go, “Here’s the model.” Go in and tweak it, and suddenly they’re doing more. They can do more work. They can sit in more calls. They can be in the boardroom as opposed to just at their desk all day. Everybody wins in this story. It may look scary at first. Companies, in the meantime, are going to spend a ton of money on it, and their CapEx is going to go through the roof. That’s a separate problem, but, like, we’re all going to be so happy about it in the future.
What do you think drives that fear? Because it was the same thing. The assembly line came out in the early 1900s. Everybody’s like, “The jobs are going away. It’s more productive,” but what we found is the assembly line had to get maintained and have more technicians. What do you think still continues to drive that fear? I did a thread for the last 100 years, “The robots are taking all the jobs.” But every time some new technology comes up, what is driving this fear?
I put it on both sides. There’s fear on the consumer side where it’s like, “I’m going to lose my job, or something like this is going to happen,” or it’s fear on the business side where it’s, “We’re going to get displaced. We’re going to be Kodak in this story, or we’re going to try to go out in this rabbit hole, like the tech bubble, and spend all our money on it, and it goes nowhere, and now we’re out of business,” which is the CapEx bubble. We’re seeing a little bit in public markets. I think it’s the fear of change. It’s getting a little too excited and then being like, “We don’t know what to do.” For me personally, I’ve started thinking about, how can AI integrate into the products that I work on? How can we solve problems using this new tooling that didn’t exist before? I personally look at it not as like, “It’s AI.” That’s a buzzword.
It’s a buzzword.
What it really is, it’s just better backend engineering for your tool. It’s like, instead of having a four-cylinder, now you have a six-cylinder. That’s how you should think about it. But because it’s so new, we don’t even know how to do it. Like, what is a GPU? What are all these costs that we’re spending? I get pressed on that, and I appreciate it. There’s, like, how do we responsibly integrate this in a way that makes sense for the story and not lose that vision of, like, what I said earlier, the firm has these goals. Does this actually help with that? Versus, on the other side, “It’s going to be AI. It’s going to take over.” No. We’re going to responsibly integrate it.
We’re going to put safeguards in place. It’s going to be humans that are checking boxes before it moves on. It’s going to be fine in the end. We’re all going to be scared. We’re going to hit a ton of speed bumps in the meantime. It’s not going to be like we’re up into the right. It’s going to happen. But also, this is me being a glass-half-full kind of guy, maybe to a fault, maybe because I haven’t fallen on my face hard enough yet, but that’s how I feel.
Product Management Failure And Recovery
That’s a good point. Tell me about a time when you were either the product manager of something, when you fell flat on your face, and how did you get back up?
I have such a story here. I was working on something where essentially a part of a product that I was doing was very workflow-intensive and involved a lot of people having to do things with each other. It’s not a single-user journey. Ryan comes to the platform, he does this, then this happens. Ryan’s who we care about in this story. It’s Ryan doing something, and then Paul sees him do it and does something in response, and then Ryan does a response to Paul. It’s almost like a marketplace kind of thing. As part of that, we were sending email notifications to people involved in this workflow, intentionally, to keep them engaged, to make it easier for them to not slip up, reduce errors.
We had the best intentions, and it was going really well. I wanted to clean up some technology debt. Tech debt is what we call it, where essentially a bunch of old actions were just sitting in our database and clogging it up. I was like, “We’ll just move them all to this end state. We’ll just shuffle them along. No problem. We’ll clean it up. I’ll be the hero. No one will even know that I did it, and then it’ll be fine.” What I had failed to consider, and this is like a classic product management story, which is like, I went and did something and I considered 9 things out of 10, and that last one was nuclear. That’s what happened here.
Because in the process of, “These old data, we’re going to move it to the graveyard. No problem,” I didn’t think about what that was going to do workflow-wise because it was still part of this workflow. We move all this old data to the graveyard, which it was supposed to do naturally. When that happened, it triggered those emails because emails happened with each one. I knew immediately what I did wrong because I was like, “We’re going to make this change. We’ll release it tonight after hours. No problem.”
How many emails got sent?
I wake up, I check my phone, and I get up early. This is early for my boss to be emailing me. I have emails from my boss and fifteen different core clients, clients you say their name, people perk their ears up, email me directly and be like, “Why are we getting blasted with emails? We’ve got 10,000 emails so far, and the market’s not even open yet.” I’m like, I immediately put two and two together. I was like, I missed that one thing, and it was an atom bomb. Got it. Go online. I’m like, yep. All those things that we cleared out are triggering emails, and we trigger them on a job cycle so we don’t do them all at once.
It was a slow bleed, all day long. I was getting sent, and I’m just getting lit. I’m at this point calling customers and being like, “I made the mistake. I’m falling on this sword. It was me. We have a solution. This will stop by around 3:00 PM. We have a solution. We’re going to fix it. I apologize. It was my fault. This is not reflective on the business or anybody else. You can take my head to whoever you take it to. I made a mistake.” That’s the biggest thing to do, by the way, is we’re all going to make mistakes like this. This is why whenever I interview somebody for a job, I always ask them, like, “Tell me the biggest mistake you made.” I want to hear a story like this.
That sounds exhausting. That sounded like a bad day.
It was a terrible day.
That’s like a seven-beer day.
I think about it not unoften. I’m like in the shower. I’m like, “I really wish I was better at my job,” kind of thing. But it happens.
If you’re not messing anything up, you’re not doing anything good either.
I was talking to a guy. He was an early security engineer at Facebook, and now he’s a VC. You can imagine this guy did very well. He was early. We were talking about this because I told him this story, and he laughed, of course. He was like, “I was the guy that put Facebook down for three hours in 2014. When Facebook’s down, it loses $20 million a minute in loss.” I was like, “Fine. You win this round. I’m sure you had a lot longer showers than I did after that, just banging the wall.” But it happens. We laughed at it later because we didn’t mean to do it.
It’s so funny. I’m the industrials guy. A bad mistake for me is throwing six hours’ worth of product in the trash can, but in tech, a bad day is annoying, like 20,000 customers. I actually put it in perspective. I think industrials wins in this spot, actually.
This is my thing with product management. You get a lot of responsibility upfront, especially in the early-stage startup arena where they need somebody to come in who knows the business context, knows what problems they’re trying to solve, and wants to do it. You can end up with a 24-year-old, which is probably how old I was at the time, it was a few years ago, having that power to make a mistake on that scale. It’s like a double-edged sword when you see that video and you were like, “I want to be a PM.” It’s not like that outside of those contexts. It’s actually a very stressful job.
Advice For Aspiring Product Managers
You’ve told a horrible experience. You’ve got some good sides, some upside, you’ve got early exposure, which is a good thing. What advice would you give to someone that says, “Product management is pretty cool. You’re telling a better story than pull people. Do you want to start in finance? Do you want to start in engineering?”
Product is interesting because people most often end up in it not having known what it was, or they were doing something else before. I stumbled into it. I didn’t know what it was when I graduated college, and I couldn’t be happier because I love it. It depends on the product that you’re doing, honestly. There are a lot of engineers who become product managers because they just had that interest in the business, and they know the whole tech stack. It’s a natural fit. There are business people who are in an arena, like FinTech, who started in finance, who are the perfect people for it because they know the business context already and they can learn the tech later. You’re always going to fill in one of those gaps. It’s all about where you start. There are things like hard tech.
The guy who’s a product manager at NVIDIA? I’m never going to be qualified for that. Are you kidding me? The level of engineering you need to have on solid product. The point that I’m trying to make with this is you find something that you’re interested in. Whether you’re interested in finance, healthcare, or biotech, you get into that world at all. If you can prove yourself, people will take a chance on you. Because I didn’t have an engineering background. I had a finance background, and next thing you know, I’m in a WeWork with brilliant engineers, and they have to trust me. That’s hard, but if you can prove yourself by being like, “I know what customers want, and I know when I’m wrong, and I take feedback really well.”
This feels a bit like the Rick Rubin interview. If you’ve seen this, can you code?
Barely.
Could you organize a database? Could you stand in for someone?
If I had ChatGPT, I could get close, but no, I couldn’t do it all the way.
Engagement With Developers
This really feels like the Rick Rubin story of being a producer. What about you do developers find engaging, and why do they want to work with you? Obviously, you’re an engaging person, but why do they want to work with you?
This is actually a great question because this happens all the time when someone who’s not an engineer with no computer science background ends up in a product seat, and suddenly brilliant technical people have to work with you, and they may not want to at first. I’ve had conversations with VP-level engineers that I work with who have told me straight up, like, “When you came into the seat, we were like, great, here we go. Another guy that looks like everybody else in finance we have to talk to who doesn’t know anything.” You have to earn the seat at the table, and the way that you do it is, like, you find out what you’re good at in this equation that is like taking a product from not existing to existing, and you just focus on that. You find the people who can fill in the gaps, and you just say to them, “I know this thing, and I know that I’m right on this. I know that you know this part.
Can you figure out what to do here?” For example, the product brief, which I put in the playbook, that’s the golden thing that I do. It’s literally like, I talked to fifteen users. I wrote down all their interviews. Here’s the consistencies. Here’s where I think we get the most bang for our buck, then I go to my tech leads and I’m like, “How do you think we should solve this given what you know and what I just told you?” You trust them. Over time, they’ll start to trust you because they’re like, “You tell the story here. Great. We then code it up. Great. Sales sells it. Got it.” You just become part of the value chain.
Feedback From The Team
Interesting. One of the things I always tell my team is, and I did this when I took the keys to the chemicals industry business, the first thing I did was I put on pencil coveralls and went out there. I made batches with the team. I helped stir the ingredients up, reacted the chemicals. I feel that’s a little analogous to what you do. You actually do the work and unpack what they’re doing. Given that, if I did anonymous feedback with the team you’re working on, what would they say about you?
That’s a good question because I’m thinking about feedback that I’ve got over the years that has made me better, that has been really constructive. Some of the things that actually have really pushed me to be better are like, “Ryan’s trying to do too many things, not well. He should do one thing really well and then rely on us to do the rest.” I would write documentation for, like, “Here’s a problem that we should solve.” I would say, “Here’s how we should solve it. We should use this database.” They’re like, “Ryan, that’s not your job. We’re going to know what to do. We’re the experts.” I have learned over time that trying to overextend myself is actually bad for the team.
There’s a thing that I’m good at, and if I keep getting better at it, I will expand here. That’s one thing. Also, being able to fail quickly is more important than you think because if you’re a product manager and you get married to your product and you feel connected to it, you’ve lost. Because, like, that thing works for the business at the end of the day, just like you do. This happens a lot with junior product managers. You give them a part of the platform and you’re like, “You own this experience.” They’re like, “It’s mine.” It makes you feel fuzzy in the morning because you get to have something, but if it’s not doing well, and the business’s goal is to make money and get users, we got to cut and run here.
Being able to fail quickly is more important than you think. If you're a product manager and you get married to your product and feel connected to it, you have lost. Share on XWe got to either save it and change something dramatically, or we’re just going to stop doing it and put you on something else that’s going well. You can maybe be better at that. Being able to notice that about myself and not sink myself into a cost and be like, “I’m going to save it,” but being like, “You know what, guys? I actually don’t think this is a good idea. I know it was my idea originally, but, like, I was wrong. This is why I’m wrong. This is why I think I’d be right to do something else.”
Career Outlook
Synthesizing all that, where do you see your life and career going in the next 5 to 10 years? You’ve done some investment background, you’re a product manager, you worked in high net worth finance. Where do you see your life going?
I certainly didn’t think it was going to go here, which is awesome because it’s been a pleasant surprise. You’d be sitting in this room is such a black swan event in my mind. You got a crazy view, and the team out there is great. It’s awesome. For me, I love doing product work. I love operating. I love going into the situation room and it honestly being a mess and then getting to clean it up. That sounds psychotic when you say it, but I really do feel that way. I think it means that I should stay in product. I want to grow up and be a product leader, have more junior PMs that I can mentor who then become like me, and then I can lead a product org and maybe one day be a CPO or a founder.
At some point, do more investing and transition to being that investor. The value-buying investor. Kind of like what you guys do. You go in, and you have an operating process. You buy the control to go in there and change it and make it better. I would love to do that in tech. If that means, at the early stage, I’m like the in-house product guy that can come in and help you find product-market fit, I would love to be that guy, and I’m working towards that.
Advice For 22-Year-Old Self
Last couple of questions. We ask these two all the time. What advice would you give 22-year-old you getting out of college?
Explore more and faster because, when I came out of college and I joined JP Morgan being 22, I was like, “Cool. I’m going to do this now.” I just was, like, siloed, and I couldn’t get out of my own way on the track.
You’re on the track.
I’m on the track. I’m going to grow up. I’m going to be associated VP blah, blah, blah. But the reality is, if I could go back in time and do it differently, I would have just been more curious, and I would have spent more time being curious. I would have spent my Saturday mornings thinking about, why do I like this? Does anybody else do this? Will they talk to me? I would have networked harder. I would have found better mentors earlier. That is something that I absolutely feel. For example, you ever seen Arnold Schwarzenegger’s commencement speech?
I love it.
Love it. He’s like, “Don’t call me a self-made man.” I feel so much more that way now than I did at 22 because I didn’t recognize that. Because when you’re 22, you have a chip on your shoulder. You’re like, “I have to prove myself. I’m going to be the best analyst.” That’s ridiculous. Go talk to people, hear what they do, see if it inspires you, and change often.
Go talk to people, hear what they do, see if it inspires you, and change often. Share on XMost Influential Book
Last question we ask everybody. What is the best book you’ve ever read or most influential on you, and tell me about why.
Good one. I got to think for a sec. I’ve read a lot of books by different tech entrepreneurs, like Peter Thiel’s Zero to One: Notes on Startups, or How to Build the Future. I feel cliché saying that, but that one’s really good. I read The 48 Laws of Power, which I think you introduced me to. I love that one.
One of my favorites. It’s a defense against the dark arts, everybody needs to know.
It really is. I read The Art of War, but it was a little tough to get through. It’s very context-heavy. I’m like, “Ancient China? This is a little difficult.” I’m going to go with The 48 Laws of Power or Art of Seduction: An Indispensible Primer on the Ultimate Form of Power.
Art of Seduction: An Indispensible Primer on the Ultimate Form of Power is good.
Because that one’s not just about what you think it is from the title. It really is a book about getting what you want by, like, either allies or enemies, and how do you help the right people and not waste your time in other areas. I feel that way about life. Those books put me onto that in a way that I couldn’t describe.
Super great having you out, Ryan. How do we get in touch with you?
You can find me on LinkedIn. That’s probably the best way. I have a Twitter, Ry Harrington. That’s definitely going to be the place to go. If you want to DM me, I’m always open. I’m happy to talk. I would love the outreach. LinkedIn or Twitter are going to be the best.
Super good to talk to you.
Thank you, Paul. I really appreciate it.
Talk to you soon.
Bye.