In This Episode
Charles Rosenblatt, CEO of Butter Payments, joins Rory Holland to pull back the curtain on the operational realities of global payments and subscription models. With over two decades of experience spanning traditional powerhouse banks like JPMorgan Chase to hyper-growth fintech exits like Hyperwallet and Payoneer, Charles brings an authentic operator perspective to the mic.
The conversation explores the massive, often hidden threat of involuntary churn—where mechanical payment failures quietly alienate good subscribers—and how Butter utilizes machine learning as a seamless predictive layer to capture lost revenue. Beyond the technology, Charles opens up about his journey from a competitive college athlete to building a fintech career, the deep personal influence of his father, and the invaluable leadership lesson of prioritizing long-term victory over short-term battles.
Key Takeaways
- The Reality of Involuntary Churn: Subscription businesses often lose valuable customers not because of product dissatisfaction, but because of technical friction and silent processing failures within the payment plumbing.
- The Operator Advantage: Successful execution in high-growth environments requires leadership to stay intimately connected to the operational blood and guts of the product rather than managing solely from a high-level conceptual strategy.
- Seamless Optimization Over Overhaul: Rectifying transaction friction does not require merchants to rip and replace their entire infrastructure; machine learning can act as a non-disruptive predictive layer directly on top of existing processors.
- The AI Evolution in Finance: The horizon of financial AI is shifting from reactive recovery to proactive prevention, using intelligent modeling to determine the precise timing and channel to clear a transaction smoothly.
- Legacy vs. Agile Infrastructure: Traditional bulge-bracket banks excel at massive security and scale, but the modern consumer experience requires the nimble, tech-first infrastructure natively engineered by modern fintechs.
- Long-Term Strategic Focus: True leadership maturity means accepting that it is far more critical to win the overarching war than to exert excessive energy trying to conquer every minor individual skirmish.
- Parallels of Corporate Coaching: Leading a rapidly growing company mirrors coaching a competitive sports team, relying heavily on developing individual talents, fostering extreme accountability, and aligning everyone toward a singular collective win.
Transcript
Hook- Mastercard Visa Negotiation
Charles Rosenblatt
I went to MasterCard and said, here’s the deal I need. If you tell me yes, I’ll accept it. If you don’t, then we’re done. They said we can’t get there. I said, fine, we’re going with Visa. I got a call from someone who said, No, we’ll match those terms, no problem. And I actually told her, Not only am I not giving you the deal, I’m biased not to work with you again on this because I told you what you needed to do to win. I was not lying. I said, you need to hit 11, whatever the number is.
You said nine was the most you can do, and after you lost the deal, you came back and said eleven. That’s not the way I do business. I got to pay a near couple years later, we’re doing a MasterCard deal. The first person we met on the other side who was negotiating the deal was the same woman who we negotiated the deal with at Hyperwall.
Introduction
Rory Holland
Hi I’m Rory Holland, CEO of CSTMR, and the host of Mighty Finsights. Every year I talk with hundreds of financial leaders and innovators. We unpack the highs and the lows in financial services in FinTech. And today, Charles Rosenblatt, the CEO of Butter Payments, joins the show. We talked about a ton of great stuff, including the painful lesson he learned about negotiating and why he’s never repeated the mistake. Why the development team at Butter is using AI to accelerate everything they do and the magic of receiving unreasonable requests. Join me as we get to know the people behind the brands we trust. Let’s dive in.
The Javelin Origin Story
Rory Holland
Well, hey Charles, welcome to Mighty Finsights. So good to have you.
Charles Rosenblatt
Hey Rory, thanks for having me. It’s great to be here.
Rory Holland
Yeah, man, so much fun stuff to talk about. Butter Payments, of course, the work that you do now, but I want to start with something that’s near and dear to my heart, and that’s athletics. I noticed that it might be a bit of a theme for us today as we go through some of your background and how that applies into the work you do at Butter, but I understand you were a competitive athlete in college. Is that right?
Charles Rosenblatt
Yeah, it’s actually a pretty funny story and a great lesson for the future, which I think you want to talk about. I actually played tennis and baseball for a while. And then I did some serious damage to my rotator cuff. And I don’t know how much you’ve either tried to play tennis or baseball with a rotator cuff problem. It’s not a friendly thing. And so we had to have PE credits in order to graduate. And so I said, okay, great. I’ll go take this badminton class.
And the badminton class was taught by the track coach and he said, looks like the way you’re swinging and your form, you’d be great at throwing the javelin. I’m like, okay, I’m not sure I get the correlation here, but sure, come out and practice, come out and try. And I went out and tried and it went well and I wound up being an All-American by the time I graduated. And I was an All-American who practiced two days a week,
because my arm couldn’t take throwing much more than that. And so some of the lessons you learn in general — it was a sport I’d never done in my entire life. You just practice, and sometimes you practice differently, and everyone has their own way of doing things. Other people practice five days a week. I threw mostly only in the meets. Athletics are a big part of my life in general, but this was a fun experience and a great thing to take an individual event and really make it a team event overall as well.
Rory Holland
Have you ever thrown a javelin before?
So it wasn’t until college that you got exposed to this opportunity. And did you just go out, show up, throw the javelin and were a rock star? Or what was the process?
Charles Rosenblatt
Pretty much. Like he said after badminton one day, he’s like, before you have your real classes, come out and try to throw. A buddy of mine and I went out and threw and he said, hey, there’s something here, try this. I always had a very strong arm. In baseball, I threw in the mid to high eighties. I could throw from the center field fence all the way to home on the fly. So I had a strong arm and he just figured out a way — credit to him —
that this was something he could teach. He was an All-American javelin thrower at UCLA many, many years earlier.
I liked the people, we were friends. It was great to go out. I played two or three sports in high school depending on the season. So to be part of the athletic community was great. I think it’s important for lessons learned. Just picked it up. By the time I was a senior, I finished All-Conference my junior year and senior year, and then senior year made nationals and was All-American — second team All-American. But yeah, it’s a funny world.
Rory Holland
Oh my goodness. That is a funny world. And I assume you don’t go out on the weekends and throw the javelin.
Charles Rosenblatt
No, I don’t. I offer people to catch if they’d like. There are many, many people I offer. My sons haven’t fallen for that yet. It’s funny because my son is actually a sprinter and a thrower in high school now. And javelin is not allowed in the state of Virginia in high school. I think there were just too many people getting hurt. So it actually, ironically, is only a college event in some states.
Rory Holland
Reminds me of lawn jarts. Do you remember those? You throw them up in the air and they stick in the ground. I don’t know how many kids got stuck in the top of the head. I don’t think those were around very long.
Charles Rosenblatt
Yeah. My kids like to mess around with archery in the backyard. And that’s like, you can’t do that when the dogs are out. That’s not a safe event.
Rory Holland
No. Like, hey, there might be some hunting involved of our beloved animals. Yeah.
Charles’ Father: “He Was Always There”
Rory Holland
So how was your dad involved in your life growing up related to your sports and other things?
Charles Rosenblatt
My dad was my beacon. He was a very, very successful corporate lawyer — in fact, created parts of corporate law and insurance law overall. And that’s great from a respect perspective.
But he was always there at any event. When I used to pitch, he used to catch — he used to get on the gravel and I’d throw 85 miles an hour and he’d have no gear on, and I’d bounce it in front of him and he’d get hit in the shin and move on.
We used to play softball together all the time. He coached all of my teams. Not only was he very important to me as a father, as a figure to look up to from a professional perspective — he was always there as I did sports growing up. And I think that’s really important.
Rory Holland
Yeah. The influence our dads have on us, particularly as men, as we enter into the business world.
Comparative Advantage, On and Off the Field
Rory Holland
I wanted to kind of transition that a little bit — how did you see yourself transitioning that competitive spirit into business? And did it come naturally to you? Is it work? Because I know how difficult that can be. I did it myself, being fairly competitive through my younger life and in sports and athletics, and then figuring out how to transition that competitive nature into business.
Charles Rosenblatt
You learn how to interact with people. And I think that’s the biggest piece of sports. I think that’s the biggest piece of business. As much as AI is fantastic, there’s a piece of interacting with people. I used to joke — in my career, I was at Capital One very early on. And Capital One had some of the smartest people I’ve ever worked with. There were also a lot of people who felt very comfortable in front of a spreadsheet,
but not necessarily talking to people. I came from a hedge fund before that, so I have an analytical background. But my comparative advantage was talking to people — not sitting in front of a spreadsheet, which I could do, I think, as well as most people, but not to the same comparative advantage. And you find out about comparative advantage in sports very early on. Hey, I want to pitch, but you’re the fifth best pitcher. Go play outfield because otherwise you’re not going to play — you’re better
comparatively than the other outfielders than you are as a pitcher. Some of that just plays into figuring out what your role on the team is. And I’ve played many different roles, everything from the most junior person at a large hedge fund to the CEO that I am today. Understanding your role is key in any team sport, whether it be basketball, whether it be baseball, even track as a team sport
when you get to a competitive level. And I think that’s filtered through my whole career. I learned a lot of that from my father, but I learned a lot of that from sports as well.
Rory Holland
Yeah. What I hear you saying is you were a utility player and you were adaptable. You learned how to use your skills and your talents to do a variety of different things. No matter what it took, you were able to move into those positions and learn from the ground up.
Charles Rosenblatt
Yeah. There are a couple of things. One is even today, when I’ve gone out for jobs or talked to people, it’s sort of: hey, Charles, you’re a best available athlete type person. If you need a seven-foot center because that’s the missing piece to your team, don’t hire the six-foot guy who can’t jump. Probably not the right move.
But if you want someone who is the best available athlete to make your team better, who can play multiple different roles — I’ve never played the role that my title is. I’ve always played different roles on top of that. And I believe very strongly — when I started at D.E. Shaw, which is now the second or third largest hedge fund in the world, I’ll never forget the guy who started next to me. We were doing treasury work for options and derivatives trading.
He graduated from Berkeley with a degree in arts, science, and French literature. Same day I did. He was a mid-twenties guy. Smart people can learn derivatives, right? None of us are going to learn this in college. He was just really smart and could come in and figure it out. In fact, I needed a guy who could tick and tie worksheets better than anyone. So I went and found someone who was detail-oriented. The guy I found actually was from Duke and he had a degree in —
I only remember that it was something like entomology, determining insects. It’s like, if you are that specific and precise in that field, and we hired another guy who was a music major — you have to be really specific in music to get things right — they can learn finance. Finance is easy to be taught, right? What you can’t learn is being really smart and being adaptable enough to figure things out.
Rory Holland
Yeah. You being a utility player, but then also at a young age learning how to hire the right people — not just looking at specifics like are they in finance, do they understand this particular thing, whether it’s bugs or research — but seeing that as an opportunity for someone who is coachable and can learn. That’s really cool.
The Road to Butter
Rory Holland
So how did you get there? You got involved in finance early. You’ve had a very storied career, some exits, things like that. Tell me a little bit about your background and how you arrived at Butter.
Charles Rosenblatt
Yeah, so some things come together. I spent about 10 years in the credit card industry. A lot of outward-facing roles creating rewards programs, doing partnerships and all that. And when I went to Washington Mutual, I was hired as essentially the first executive hire post the Providian acquisition. So I joined Joe Saunders and Dave Tomlinson and Warren Wilcox and that team there who had achieved so much.
When I got there, I was running product at the time, and rewards as a piece of it.
I hired this amazing woman by the name of Sophia Pogreb out of McKinsey to come join my team. I took my team from three to twenty-one. Probably the proudest thing I’ve done in my career when I look at how successful these people have been over the course of time. What a great group of people. It really makes me proud. But Sophia was one of the all-stars. She went on to be a co-founder at Next Insurance, the COO of Bill.com, and
then took over as CEO of Butter. I’m skipping a whole phase of my career where I ran global cross-border payments companies — we can talk about that later — but I’m trying to get to your question on the Butter side. Sophia called me while I was doing some work with some VCs and private equity firms and their portfolio companies and said, this is an amazing product. It really works well. We have a good group of people.
She said, I can handle the operations and tech side of the house. Can someone come in and run the front of the house? Let’s do this together. And to me, it’s about working with good people. Everything else falls into place if you have the right people. And I knew Sophia was not only good people, but was really good at what she did. And so I said yes.
I came in, ran that for about four months. Sadly, Sophia had some health issues in her family — not her, thank God — but in her family, which was going to take her internationally. And so she had to leave and the board asked me to come in as CEO, which I’ve done for the last six months or so.
Win the Room, Not Just the Deal
Rory Holland
Got it. And you’ve had some successful exits. I want to back up real quick. There’s a particular interpretation people have — “successful exits” m eans X or Y. What do you think are some of the biggest misconceptions about that?
Charles Rosenblatt
I’ll use exits, but I’ll talk about partnerships in general. If everyone doesn’t walk out of an agreement a little unhappy, then we didn’t do our job. Your job is to do the best you can, but not really screw over your partner.
And I’ll tell you — I’m actually about to go up to Charlottesville for my 25th business school reunion tomorrow. In business school, I had a negotiations class, which was my favorite class. I loved it. There was a case in the class where it said: you got hit by a car, you’re trying to figure out a settlement. One side is the insurance company, one side is the plaintiff. I was on the plaintiff side, and $300,000 was the cap the insurance was going to cover. And I used some tactics like, hey, I’m going to go to the press and make this terrible for you. And I got a $1.6 million dollar settlement. And they threw the curve up on the board.
No one else had gotten more than $300,000. I’m proud of myself. Great job. The next three negotiations I did, the other side wouldn’t negotiate with me because they didn’t want to be embarrassed. And we actually did not come up with a deal at all. It was a really good lesson for me. When you start talking about exits — you’re selling to someone who has a long-term view. Or if you go public, the stockholders care what you do.
If what you do is promise things that are not achievable, or try to get to a result so large that you can’t back it up on the back end, then you actually haven’t won anything. And so that lesson I learned in business school, which I’ve now taken into hundreds of negotiations over the course of my career, plays very much into exits. Just because you can get $6.2 million instead of $6.1 million doesn’t mean it’s the right thing.
Rory Commentary
Optimizing. Maximizing. Creating efficiency. Cutting waste. Extracting value. However you want to look at it, Charles is saying something that’s counter-intuitive to the way many people behave in business. It’s easy to believe that if you don’t take what’s yours, then you’ll always get the short end of the deal. Except relationships are the real driver behind long-term business success. And relationships thrive on trust, not winning and losing. After all, every exit is the beginning of another company and the gateway to another deal.
Win the Room, Not Just the Deal, Continued
Right? And I think that’s really important to think about — what are you actually maximizing in this situation?
Rory Holland
Yeah. We’re trained as business people to try to get the best deal for your side. But I’m a big believer that it has to be equally good for both. For the reasons you said — if you’re promising something you can’t deliver, or you’re embellishing, it’s going to come out somewhere.
The deal might get done, but it might get done in such a way that there are seriously hurt feelings and a lot of ramifications. So how do you take what you learned in sports — that competitive spirit, the teamwork — and still try to win the game, but also being a good sportsman? How do you see that playing into the work today?
Charles Rosenblatt
I think there are two things. Basketball has a lot of stats and I played basketball all throughout high school. The one everyone looks at is, oh my God, he scored 38 points in the game. Sometimes the assist is worth as much, if not more, than you scoring yourself, right? And if you think about that logically when you’re talking about a deal,
there’s multiple things. There’s the dollar value, but there’s also the effect on the people. There’s the long-standing effect. And candidly, fintech’s a small space. You’re going to run into people again. And I can tell you a relatively funny story about running into people again in negotiating if you want.
Rory Holland
I would actually love to get into it right now, because I think that’s something so valuable to the younger folks listening to this. You want to win at a young age, you want to move up in your career and have success. What you learn fast is your sphere of influence — particularly in finance and fintech — you’re going to keep running into these people. So you better do it right and treat people fairly and respectfully.
—
Same Woman, Three Tables Later
Charles Rosenblatt
Yeah, that’s right. The people here are retired, so I feel okay — I won’t use names. So one of the things I’ve done in my career everywhere I’ve gone is run the Visa and Mastercard issuing relationships, whether it was Capital One, whether it’s Washington Mutual. So when I was at Hyperwallet, we were trying to decide between Visa and Mastercard. We were a Visa issuer. We were willing to move to Mastercard.
Visa put a package together. I went to Mastercard and said, guys, here’s the deal I need. If you tell me yes, I’ll accept it. If you don’t, then we’re done. They said we can’t get there. I said, fine, we’re going with Visa. Called them up the next day. Got a call from someone who was two levels senior to the person I had done the deal with,
who said, no, we’ll match those terms, no problem. And I actually told her: not only am I not giving you the deal, I’m biased not to work with you again on this. Because I told you what you needed to do to win. I was not lying. I said you need to hit eleven — whatever the number is — you said nine was the most you could do. And after you lost the deal, you came back and said eleven. That’s not the way I do business. So we stayed with Visa.
Then a couple of years later, we were doing a Mastercard deal. The first person we met on the other side negotiating the deal was the same woman I had negotiated with at Hyperwallet. And she knew — when I say this is what you need to win the deal, I mean it. We wound up getting eight to nine digits, probably more than I think we should have, in that deal because our history was: if we don’t meet what he says, we’re not going to
win the deal. And then, even funnier — I left Payoneer a year and a half later to be the acting CEO and president of PayQuicker. As I arrived there, they were negotiating their Mastercard deal. And you’ll never imagine who was on the other side of the table. It was that same woman again. And we wound up doing a great deal with Mastercard again, great terms. You run into these people over and over. And because of the way I dealt with them the first time —
in fact, if I had taken that deal from them after I’d given it to Visa and they had balked, not only would I not have Visa as someone who wants to work with me again, Mastercard would have known: hey, this guy, you just need to not give him what he asks and then try at the end. They knew I walked away because I told them what they needed and they didn’t hit it. And that benefited me in the next two negotiations.
Rory Holland
That is so valuable. That whole story is an example of: you do things the right way. You put out what you’re looking for and what you need. You stand by that, and then you build good relationships, and people know how you work — you’re consistent and truthful and honest and authentic. All these words that we throw around, but in business sometimes folks forget about that, because we do so much virtually these days.
Versus back in the day — you remember these days, Charles — when you sit across the table from someone and you’re making a promise and shaking a hand before you send the piece of paper over via fax. It meant something because you’re looking somebody in the eye and you have that physical energy with each other. I think it’s great for people to hopefully hear what you just said and know how much that means decades down the road when you’re still in the same industry doing business with the same people.
Charles Rosenblatt
Yeah. And look, I’m sure there are plenty of people who I have not made friends with over the course of time. And I’m sure there are people who I have made friends with. But if you’re fair — and I think everyone does things differently. I’ve negotiated with someone recently who I call a zero-to-ten negotiator, right? You have to start at zero, they have to start at ten, then you go to three, then they go to seven, then you wind up at five and you’ve wasted two months and no one feels like they won.
My style is much more like: I’m going to cut through it and we’re just going to get to what makes sense for both of us. And Rory, you asked a question a couple of minutes ago, which is how do these deals happen? If you can figure out a way to expand the pie, it’s much less about fighting over the hundred. We each get fifty. But if I get it to 110, can I keep 58 of it and you get 52? And so you need to look at deals as a whole — how they can be expansive and mutually agreeable. What are the key drivers that person has?
So that person may need to sell a car by March 31st because it’s the end of the quarter. You’re helping them by signing a deal. They’re helping you by giving it to you a lot cheaper than you probably should get. You’ve both mutually hit goals that are important. What I always try to do is take the other side.
What I do is think about what’s a good deal and what would make sense for the other side, and work backwards from there. If all I’m doing is thinking about what’s good for me and what’s good for my company, we’ll never get to the optimal situation for everyone involved. And I think that works in M&A as well as partnerships and transactions.
Rory Holland
Just like in our day-to-day business, right? I always try to do the same — walk a day in someone’s shoes. If you understand where your potential partner or potential next deal is, what their needs and wants and desires are, and you get to know them at a human level, you can negotiate from a place of strength because you know each other and you can be open and honest and say, I want ten. We’re not going to start at one, I’m starting at ten, this is what I want. I really love that. Thank you for sharing all that.
Predicting Failure Before It Happens
Rory Holland
I wanted to shift gears a bit and talk about Butter Payments. In a sentence — what does Butter Payments do? What’s the market you serve? And I wanted to talk about a really hot topic after that.
Charles Rosenblatt
Sure. What Butter Payments does is use machine learning and AI to solve for involuntary churn in subscription payments. That’s payment failure. You have a subscription — MasterClass, who’s a great client of ours — it’s the fifth or thirteenth of the month, they try to take their payment, your payment fails. And what a lot of companies would do before we came along is cancel the subscription. So they’ve lost this customer they worked really hard to get. What we do is use around 120 data points about every transaction — over billions of transactions — to come up with an ML strategy to recover that payment for the merchant so that you stay on as a subscriber and the merchant keeps you.
And then what we’ve really rolled into now — given my background in the hedge fund world and Capital One — is a lot of predictive analytics. We’re actually able to tell our clients who is going to fail before they fail, and who is going to fail on acquisition even on the second transaction, so that you don’t pay out your vendors unnecessarily. That’s essentially what we do as a whole. We solve for involuntary churn at all points in the cycle.
Rory Holland
Predictions — great word. That’s exactly what I want to talk about. There’s so much talk about AI and predicting the future. I don’t know the answers. It’s going so fast. I’m curious how you think about AI — it’s such a core part of what you guys do at Butter. How far into the future do you think you can predict where things go? And what does it mean for your capabilities now and maybe in the near future?
Charles Rosenblatt
I think of AI as two separate things. ML — machine learning — which is what we historically have done. We were doing it at D.E. Shaw. When we were doing 15% of the trades on the New York Stock Exchange in a day, that was essentially machine learning. What AI has allowed is things to happen so much faster. We used to have a team in New York who coded during the day and a team in India who coded during the night — we were one of the first companies to do that, the round-the-clock model.
What probably took weeks to code for trading strategies, leveraging AI could probably be done in hours or less. And so from that perspective, you’re only as good as your inputs. The AI is not going to randomly create a new strategy based on nothing. You need to have the knowledge to provide the inputs in order to figure it out.
Rory Commentary
I’ve seen the truth of this in my own use of AI. While AI is allowing me to do some things much faster and easier than before, it still requires thoughtful direction or as Charles said, good inputs. AI is a genuine source of innovation across the economy and Butter Payments is using it to help business owners recover revenue they would have otherwise lost. However, I think it’s tempting to rely on AI to think for us, instead of applying our human wisdom and instincts. Let’s not lose sight of that as the technology leaps forward.
Predicting Failure Before It Happens, Continued
Charles Rosenblatt
However, Sonali — our CTO, who used to run ML at Block and is amazing — has added AI into everything we’re doing on the backend, including MCP servers. I know APIs because I can spell API, but that’s the extent — I’m not the technical person. But she’s added this throughout. We just did a session yesterday on how we’ve used AI, and
I was at a conference with our investors at Norwest where they brought in a speaker who said the average developer now has five people effectively working for them because they have five AI scripts running at the same time in the background. And we’ve seen that — we are so much more efficient than we were even three months ago. Some of those day-to-day tasks that were more menial are now being covered by other means.
I think that’s a huge benefit. It also scares me, candidly, for people who are just coming out of college whose jobs may have largely been those tasks — and I have kids about to graduate college. But that’s what I’ve seen is changing. It’s the speed. The speed is just absolutely remarkable — much more than the intelligence, so to speak. You still need human intervention.
Rory Holland
Yeah. I wanted to ask you about speed because you’re right — we see it too in my business. We’re using the latest technologies to take some of that menial manual work away so that we can be more strategic. But when I think of speed, my son used to race professionally on dirt bikes. In the world of motor sports, you can go really fast, but things tend to go really wrong catastrophically if you’re going too fast or you don’t have everything tightened up. Everything has to be fine-tuned to go at those speeds — whether it’s NASCAR, Indy, or motocross. What I picture in my head is we’re all going at hyper speed because there’s this FOMO — that I feel personally as a business owner, but I also see it out in the world. Nobody wants to miss the window. So everybody’s diving into AI.
And when you’re looking at personal data and credit card information and PII and all the stuff we deal with in our industry — how do you think about that? A wheel could fall off and then it’s complete catastrophe and you’ve totaled the car.
Perfection Is the Enemy of Good (Except When It Isn’t)
Charles Rosenblatt
I think what you’re hitting on is exactly right. I use an expression — I didn’t create it, many people have said it — but perfection is the enemy of good. When you’re flying a plane, perfection is not the enemy of good. Perfection is necessary. And so there are some tasks — maybe the dirt bike with the lug nuts, maybe NASCAR keeping a tire on — where being just good at something and moving to the next thing is not possible. Because if you’re not perfect, someone’s dead.
Thank God, nothing that we do in the fintech world means someone’s dead if you’re not perfect. And so leveraging AI to get you to those next steps and those learnings — because data is king. The speed to data is really critical. The more speed you have to the data, the more you are able to actually apply. So being good in some ways is just good enough. And as a leader, what your role is is understanding what things you need to be perfect at and what things it’s okay just being good at.
Rory Holland
Yeah, that’s a great point. I mentioned the lug nut because one day I did forget to put it on all the way, and my son’s front tire came off. Thank goodness he was young at that point. He didn’t get hurt, but it scared the crap out of me.
When the Market Takes the Wheel
Rory Holland
So I wanted to talk a little bit about your move from retail banking and credit cards into fintech and infrastructure — that’s a completely different move in your career.
What was one of the biggest things from a personal growth perspective that you learned through that whole process?
Charles Rosenblatt
Maybe less personal growth and more about direction. When I went to Washington Mutual — and I say Washington Mutual was “acquired” by Chase in air quotes, because the Fed took us over and handed the skeleton of it to Chase — even though
I was doing really good things. My credit card portfolio, my rewards portfolio, was the only portfolio that Chase wound up keeping and asking me to stay — although I decided not to. That was completely out of my control. And I made a decision at that point in my career that I needed to — I don’t need to run things, but I need to have a voice and control. And what happened at Washington Mutual, where a mortgage business I had nothing to do with tanked the whole company, can’t happen to me again. And I think that’s been a really important and guiding principle. I trust myself. I’d never worked on commission before in my life, but I’ve had roles where I work on commission because if I deliver
and can control my own result, that’s a really interesting thing. And that event in 2009 sort of pivoted my mindset in a number of ways.
Rory Holland
Was that the first experience you had with the market just completely dumping? In the business world, that is?
Charles Rosenblatt
No! At D.E. Shaw — which is now the second or third largest hedge fund — we lost about $800 million of Bank of America’s money back in 1999. And I had built and ran the Treasury desk there. Running a Treasury desk for a company that doesn’t have the trading and the money anymore is not really relevant. So I lost my job and I decided to go to business school, which turned out to be a great pivot. So I’d seen this before. It was actually about ten years to the day between the two events.
And then COVID came and that changed things as well. Being nimble and being able to — as we said at the beginning — be the best available athlete and help organizations in different ways has mattered. I’ve had four or five times in my career where I’ve taken on year-long consulting engagements, some more formal, some spanning multiple years.
What I realized was: one, I love getting involved with solving the problem for folks. That’s really the fun part. And two, you have to be able to help with different things. If you’re a crypto expert but all your expertise is Ethereum, the use case for you across many organizations is quite small. But if you’re a crypto expert and you’ve learned the whole landscape,
you can actually help in many ways. And I think that’s part of the guiding principles earlier of the best available athlete theory.
Rory Holland
Love that. If you reflect back, what was one of the greatest challenges in your career that you didn’t think was solvable, but somehow you moved through it?
Charles Rosenblatt
It’s a really interesting question. I’m not sure I didn’t think it was solvable, but I thought it was unreasonable. When I got to Washington Mutual, Warren Wilcox and Joe Saunders — both amazing, historic leaders for what they did at Providian and then at Visa — came to me with a list. I had a team of three people.
And they had a list of 40 projects that they’d been writing down on a piece of paper for three years that they wanted done. And I’m like, guys, I was running product at the time. We’re not doing all 40 of these. There’s no way. And what I did is I went to Joe with a plan. I said, Joe, I need 21 people if you want all 40. And his response back to me was:
Do I get all 40 if I get 21 people? I said, yeah, that’s what I said. And I grew my team out — the team I was talking about earlier with Sophia on it, as well as many others — out to 21 people. And while we didn’t deliver all 40 — because candidly, some of them made no sense to do whatsoever — we delivered everything meaningful on his list and then some. And my lesson out of that is:
Even if it seems outrageous, make the ask. The worst thing that can happen is they say no. What can you do with 13? And then I go back and say, well, we can do these 23 of them.
Rory Commentary
I’m a big believer in the old proverb that if you knock, doors will open, and if you ask, things will be given to you. The universe responds when we face tough situations and ask what’s possible. On a more practical note, if you take the time to create a plan and a list of necessary resources, you might just get what you ask for. But if you don’t plan, then you’re at a severe disadvantage for any negotiation. As the Rolling Stones said, you can’t always get what you want, but if you try sometimes, you get what you need.
When the Market Takes the Wheel, Continued
Charles Rosenblatt
But the task of doing 40 with three people was never going to happen, even with AI probably.
Rory Holland
Yeah. Well, it seems like everything’s possible with AI. That’s what everybody’s talking about. We’ll see if that’s true or not. Thanks for sharing that story. You went to school in Virginia — did you grow up in Virginia?
Charles Rosenblatt
No, I grew up in Northern New Jersey.
Rory Holland
Okay, so grew up in northern New Jersey, went to school in Virginia, then you moved to the Bay Area — about 15 years, is that right? I spent 13 years there myself. And now you’re back in Virginia. Tell me about that journey.
Charles Rosenblatt
After D.E. Shaw, I went to business school at Darden at UVA. I was offered a job at Capital One and they said you can go wherever you want. I was working with teams in Boston, Northern Virginia, Richmond. And I’m like, I get paid the same everywhere. I’ll take the job in Richmond. I met my wife in Richmond. Her family is here. And then I was offered the job
out at Washington Mutual, which moved me to the Bay Area. Loved the Bay Area, spent almost 15 years there. But when I joined Payoneer — I had a direct team of over 100 people in Israel and a dotted line team even larger with the rest of our management team in New York. And my agreement with Scott, the CEO at the time, was I can’t stay in San Francisco. The time difference to Israel is ten-plus hours.
There’s no working hour of the day where you’re both in normal business hours. It was COVID, so I didn’t need to be in New York. And so my wife and I decided we like Richmond, we like the quality of life here, her parents are getting older — it was a good time to be there. And so we moved back to Richmond. I’ve been here for almost six years now.
Rory Holland
Were your kids born in the Bay Area?
Charles Rosenblatt
I have one that was born in Richmond before we left, one that was born in the Bay Area, one that was born in New York when we were there for two years, and then another one born in the Bay Area. But they all pretty much grew up in the Bay Area outside of those two years in Northern New Jersey.
Rory Holland
Yeah. It’s funny how our careers take us different places if we’re open to it. You can stay put. I have plenty of buddies in Detroit — where I went to high school and college — who just planted themselves, got married, had kids, never left. And then there are guys like you and me who’ve probably owned a few different houses in a few different states.
Charles Rosenblatt
Yeah. And what I learned, candidly, is I moved my son who was in high school and my other son who was in middle school at the time. That was difficult for them. Not only was COVID a hard time, it was difficult for them. And I now still have a son who’s a freshman in high school and a son who’s a junior in high school. People have asked me in the last couple of years: can you move for this role? And I’ve really said, I’m not willing to do that to them. I’m happy to fly in every week wherever you want me. But I’m not moving them anymore. And I think that’s become even more critical now than maybe even when we were younger.
Rory Holland
For sure. I think roots matter. Home matters. Home to me is wherever you go. But my brother never left Detroit. Now he’s in Northern Michigan, retired. But he particularly is like, “I’m going to settle roots.” I’m staying here. I’m going to buy one house, which he did. Then he bought another up north and sold the Detroit house moved up north, but as a result, like his kids have grown up basically south Detroit, Detroit, the north northern Michigan.
Executive Headhunting: “When He Speaks, People Listen”
Rory Holland
So we like to ask this fun question about executive headhunting. As I mentioned, my son was a professional motocross racer, so the father-son bond was so important to me and still is today. And your dream hire — if you could bring anyone to work with you at Butter Payments — was your dad. Tell me about that choice.
Charles Rosenblatt
I’m going to date myself — and maybe Rory, you and I will be the only ones listening to this who remember it. But there was an old ad for EF Hutton: when EF Hutton speaks, people listen. And that was very much my father. My father was very soft-spoken. He was probably the smartest person in the room in each and every circumstance. He was there, but he was probably the least vocal overall.
And when he said something, everyone appreciated what he said. I wish I was like that. I’m not like that. People will tell you I speak a lot — you can tell on this podcast. He would take everything in, think about it, and then say the one comment that everyone walked out of the room remembering.
And I think that’s an important person to have in your organization. Actually, the other person who did that in my career was Frank Rotman. Frank is pretty well known in the fintech space. Frank was my boss at Capital One, and he would say the same thing: make sure people remember the one thing you said in the meeting, instead of saying 62 different things. So not only his work ethic —
my father joined our board of education, which we always joke about: what do you get paid for being on the board of education? Nothing. There’d be days he’d get home at three or four in the morning and head back out to work at seven, because they were negotiating a teacher’s contract where he was getting paid nothing to do it, then spending all day working for his clients. Having that work ethic, having someone always by your side who you can trust, and having someone who — when they speak — you know it’s important and the whole room listens: that is
absolutely critical, not only in life, but in any organization.
Rory Holland
Yeah, what a gift your dad gave you. One, that he obviously raised you really well — you’ve had a lot of success. But two, the fact that you would want him on your team says a lot. It reminds me of Tony Dungy, the former football coach. He wrote a really great book, and I remember something stuck with me that he said. He told the guys at training camp every year: look guys, I’m not the type of coach who’s going to jump up and down and scream. He said, if I get quiet,
that’s me getting mad. You need to lean in. He was very soft-spoken. He never got upset, but when he was, he would whisper — and he said the guys would have to lean in. That was him. But he learned it from his father. And the quick story is: he was out fishing with his brother and his dad, and he messed up — wasn’t looking, went to throw the hook, and it caught on his dad’s finger. And so
his dad didn’t say anything, but as he pulled it, it stopped. He turned around and his dad walked over quietly, didn’t say anything, just pointed it out — there’s a hook stuck in my finger. He got some pliers, pulled it out, and said: you need to watch what you’re doing when you’re casting. Be sure and look around. And Tony said that stuck with him so much. His dad could have gone sideways, but he didn’t. And he said that informed the
quiet presence that he carries to this day. It sounds like your dad maybe had a similar approach.
Charles Rosenblatt
Yeah. I’m not sure my dad would be thrilled that I act the same way as him. I joke with folks: I have a ton of respect for process. In fact, I think process is one of the most important things you bring into any leadership position. But if you’re going to hire someone to create a process, if you hire me you are making a huge mistake.
I am not a person who creates process. I recognize the value of process and I like to follow it. I just can’t do it. I think maybe the same thing is true here. I recognize the value of what my father brings to the table. I would love to be that person, but I’m not. And so you figure out how to surround yourself with people who do. And I think
inherently, if you ask any lesson from my career, it’s about the people you surround yourself with — that’s much more important than anything you’re doing yourself or driving into the business.
Rory Holland
100%. We tell our kids that, right? Be careful who you run around with, because that’s how you’ll be known. On that note — as a CEO of a company, high stakes, high intensity, a lot has to get done and it has to get done well. How do you stay grounded in your values day to day?
Charles Rosenblatt
I actually think that’s probably the hardest piece because you have so many competing entities, right? You have your board, your investors, your employees, and what’s right for you. You have to figure out where that balance is. In some cases it’s fully aligned and that’s a beautiful thing.
In many cases it’s not. We’ve had to do layoffs at Butter since I’ve been here. That’s a really hard conversation. It’s my least favorite thing I’ve needed to do as a CEO. And I think the way you stay grounded is you have people by your side. We are a very small company, but I have a general counsel who also handles operations and HR, and she’s an amazing person to just speak to and say: hey, am I thinking about this the right way? You know these people differently than I do. How are they going to take this conversation or this message? I think that is critical — find that person. And if you find that person outside the business, whether it’s your wife or your partner or your friend, that’s great.
But if you can find that person inside your business who understands the problems you’re dealing with and the people you’re involved with, that’s even better.
Everything Else Is in Service of the People Who Matter
Rory Holland
Yeah, love that. Thank you for sharing that. That’s great. Well, that leads me to my last question, and then we’ll wrap up. In the season of life that you’re in now — married, older kids, some moving on to careers, some moving through college — for someone to really know you right now, what would you want them to know?
Charles Rosenblatt
I think people need to look at things both at face value and underneath that. You need to say, hey, who is this person I’m dealing with. We talked about dealing with people honorably, negotiating with people honorably. And then you also need to think about what really matters. People say this all the time. I love my job at Butter. I’ve loved all my jobs, my consulting clients, and so on.
But when push comes to shove, the people I’m going to do the right thing for are my family. We’re not going to work, we’re not making the money, we’re not selling companies for the sake of the next company. We’re doing that for the sake of the part of our life and the people in our life who depend on us and really matter. I think separating the two and understanding that is something I’d want people to understand about me — but I think that’s hugely important in anyone you’re talking to.
Rory Holland
Man, I tell you — that kind of loyalty and that kind of commitment as a father and a husband and a business person, respecting and taking responsibility for all those roles and all the hats we wear as dads and as business people — that’s wonderful. I think of you as a super loyal guy who’s got a lot of intensity, wants to do the right thing, and does at every point in his career wherever he can.
You’d be the type of guy I’d throw the javelin with. I wouldn’t catch it — I might try, but I might die. I’ll just say we can go shoot hoops or throw baseball.
Charles Rosenblatt
Rory, you’re not one of those people I’d put on the catching side. I want to keep you around.
Connecting with Charles and Butter Payments
Rory Holland
But no, this has been a real pleasure. I know you’re super busy. I really love the work you’re doing at Butter Payments — super interesting. And on that note, how do people connect with you, Charles, or folks at Butter?
Charles Rosenblatt
People can connect on LinkedIn — that’s probably the best way for me personally. As far as Butter Payments, you can go to our website and fill out a form. Or if you’re interested in just chatting or sales, you can reach us at sales@butterpayments.com or me directly. I’m pretty accessible.
I try to give everyone a chance. Someone calls headhunting and you’re not looking for a job — I still talk to every single one of them, to try to help them. Happy to do that. Happy to answer questions. Happy to talk to people. Would love to have new clients and, if I can be helpful to anyone listening in any way, I’d love to work with them and figure that out.
Rory Holland
Well, thanks Charles, man. It’s been great to have you on.
Charles Rosenblatt
You too. Thanks, Rory.
Outro
Rory Holland
That ruthless optimization wins in a one shot game. In repeated games, and in an industry where the same names circle back to the same table for years, cooperation wins and relationships win. You can see how this played out in Charles’ negotiations with Visa and MasterCard. He wasn’t trying to play a game where the winner takes all. He wanted a partnership he could trust over the long haul. You don’t get that with bluster and manipulation, as Charles’s father modeled
You achieve that through quiet competence and consistency. Every word carries weight, every promise grounded in reality. That’s what it means to be a utility player, just like Charles found in his athletic career. He brought strength and structure to the team, along with a willingness to fill in the gaps, not just score all the points. We all need partners like that. And as Charles Rosenblatt shows us, the best way to get what you need is to give it to other people.
Thank you for listening to Mighty Finsights. You’ll find all of our episodes on our website, cstmr.com, including more one-on-one interviews with fintech and financial leaders, as well as deep dive episodes on specific topics like branding and marketing. This show is produced and distributed by Customer, a financial marketing agency, all rights reserved. Our production team includes Zach Garver, Becky Dombrowski, Brad Jurger, Romina Gomez, and Balin and Curio.
