S02E10: Mike Massaro, Flywire

In this episode of the Without Borders podcast, we speak to the CEO of Flywire, Mike Massaro. After raising $120 million in a Series E round of investment, led by Goldman Sachs, earlier in 2020, we discuss life as an American unicorn, communications challenges and the future of transactions.

This episode also covers what makes the high-value payments business a success and how it merges software with transactions in a fast and friction-free way to help organisations. Listen today to hear expert communications advice alongside a discussion about the future of payment tech.

The interview, as ever, was co-hosted with Russell Goldsmith of the csuite podcast


Russell: [00:00:00] Thanks for downloading Show 119 of the csuite podcast, the latest in our special series episodes that we’re recording in partnership with the European PR Agency Tyto and their own Without Borders podcast, where we are interviewing leaders of unicorn companies to find out about the key issues, pain points and challenges that startups face and how they can address them with a strategic approach to marketing and communications. My name is Russell Goldsmith and having interviewed nine leaders of European unicorns so far, this time around, our focus switches to North America and so, along with my co-host for this special series of interviews is Tyto’s founder, Brendon Craigie, we’re thrilled to be joined online from Boston in the US by Mike Massaro, CEO of Flywire, a high growth vertical payments company that gained unicorn status in February 2020. So welcome to the show, Mike. We should probably start by you giving us a quick introduction to the business.

Mike: [00:00:52] Sure. Thanks for having me. Excited to be here. So, Flywire is a vertical payments company. We focus on the combination of what we believe is software and payments coming together, which is a major trend in tech. We started with an education vertical; it was our first vertical about 10 years ago. So, think of that as helping foreign students attend Harvard, Yale. At this point, 1600 universities across 32 different countries. We then added additional vertical markets, including health care, travel and now business payments. As we continue to add new verticals, new geographies, really what is unique about what we do, is we actually have a way in which we move the money, so we have a way to move the money. We have one shared tech platform for payment functions and then we have vertical software that’s super targeted for integration points within these industries, use cases and we bring all that together for our clients for about 500 Flymates or employees across 12 offices globally.

Russell: [00:01:48] I love that term. Flymates. Excellent. I mentioned in the intro that you reached unicorn status in February 2020, which was if I’ve got this right after a funding round of 120 million, how has becoming a unicorn changed the perception of the company?

Mike: [00:02:02] Yeah, you know it’s, it’s an interesting one. So, we’ve raised a little 250 million or so of venture capital total, you know, investors or folks like Spark, Fidelity, Bain, Temasek, which is the sovereign wealth fund in Singapore and Goldman Sachs most recently. Those are the major investors. And, you know, I would say if you asked Flymates internally, I’m probably one of the most anti unicorn type branding people heavily focused on execution, on all the blood, sweat and tears that went into building the company for ten years. So, you know, it’s nice to have the label. It’s nice to be held up as one of the hallmark companies in the fintech industry. But at the same time, there’s a lot more work to do. So, I would say they probably heard us celebrate it for about 30 seconds inside the company. And then we went on to doing what we need to do.

Brendon: [00:02:46] Brilliant. In preparing for this chat with you Mike I think we’re just reflecting on the fact that everyone’s been talking about payments for a long time and the kind of the innovation and the disruption going on in that space. And I was curious to look into that a bit more and saw that is one of the recent articles that Boston Consulting Group mentioned that the area of global payments is growing at roughly six percent annually. I’m kind of just curious, like what’s driving the growth in revenue, in payments?

Mike: [00:03:18] So there’s definitely a digitization that’s happening. So, when you just think globally in general, right, people are shifting away from cash. They’re shifting to more digital. I’d also say that the world is, prior to Covid at least, was getting much smaller. Right. People were picking up. They were travelling. They were interested in seeing the world, learning in different places, you know, potentially living in different places. So, again, I think that created a lot more digitization, you know, in even obviously the drive to ecommerce, which is, you know, increased during the pandemic. So, I think that’s all trying to start to drive those types of interactions that people are having. So, I think that’s a big part of it. The other thing I would highlight is when it comes to payments in particular, people used to go and select a payments vendor. And I think one of the other big shifts is that payments are kind of embedded in everything we do. Right. I often tell the story in New York City where, you know, prior to Covid, I was hopping out of a taxi cab, didn’t pay the taxi cab driver, thought he was an Uber, which offended the taxi cab driver. And that was a good example where payments are so embedded in my day-to-day experience that I didn’t even realize there was a transaction there. And I think that’s what’s happening with software as well. When you’re delivering software like we are to our clients, they’re sitting there and saying, well, jeez, I don’t have to make a payment decision now. Right? If payments are part of the offering, then that’s taking complexity away from me. That’s taking decision-making away from me. I don’t have to be an expert in payment. So, I think when you do that, when you have more seamlessly integrated software with payments, I think usage levels also can kind of go up because it’s just a better experience.

Brendon: [00:04:51] That’s really fascinating and helps to put that figure in context. Picking up another thing that caught our eye, a piece, I think it was in Forbes, was talking about how this is a space that is increasingly very margin thein and that fintech companies to be commercially successful really need to be sort of seeking out more vertical specific challenges to fix, which I guess that is an area that you’ve really focused on.

Mike: [00:05:20] Yeah. You know, and again, I think for us it’s the payment economics, at some point, you know, you can look at payments and say it’s very commoditised. Right. The cost of picking one vendor to process a credit card versus another can be very small. Right. So, people are trying to differentiate on the processing, the tech platforms that are behind them, the interfaces. Right. It’s part of the reason you’ve seen such consolidation inside the credit card processing sector. Right. Where there’s been massive acquisitions and in consolidation in what is traditional merchant processing. And again, I think part of why you see software kind of coming into this mix is you can deliver a lot of software to clients delivering a ton of value, and that value can then be monetized either through software licensing or payment economics or some combination of both. Right. So, if you actually have the payments integrated in with the software, you end up with a little more, I’d say flexibility, when it comes to monetization give you plenty, plenty of good examples if you think of what the software can do to add value. So, in some of our sectors, like education and health care in particular, the concept of paying a large amount of money all at once, you know, isn’t that common, right? If you’re going to send your child to Yale or Oxford. Right. You may not be able to kind of make that massive lump sum payment at one time. And so, this concept of a payment plan exists and that’s saying, hey, I can split my payment into five instalments. It’s a non-interest-bearing component, right? It’s just pretty much the university extending different payment terms because they know the ability to maybe pay 60 thousand dollars equivalent in a lump sum may be difficult for people. And so, when you look at that, you kind of have a situation where you have software adding a ton of value to both the payer but also to the end client, in our case, the university. So, it’s solving a complex problem that they have. But at the same time, your monetization is through software and through payments.

Brendon: [00:07:13] Brilliant,

Russell: [00:07:14] That’s interesting. Mike, you touched on Covid a little bit just before there. One of the things we were wondering in terms of I mean, obviously we’re recording this, you know, after a pretty difficult year. What impact has Coronavirus had on your business and how have you had to adapt it.

Mike: [00:07:29] It was definitely quite an experience. You know, we had we have 65 or so Flymates in Asia Pacific. So, a number of folks started to be impacted even in January, February, in places like Singapore, Tokyo, Shanghai. And so, we got a kind of early view than a lot of other tech startups had of what the potential implications were of having people shift and work remotely, some of the stresses that happen to people in kind of this environment. And so, when it happened here in the United States, pretty much the rest of the world in mid-March, our first focus, like many, was to make sure we could transition well to home to make sure people had the equipment they needed. They could perform their job to the best of the ability at a home office. And then that actually happened relatively easy for us. The transition we were a globally distributed team. We were used to a lot of collaboration tools. We have a video conference embedded in every television, in every office. And so that actually wasn’t a big transition. The harder part for us was actually helping our clients’ transition. Right. If you think of some of the top universities, top medical hospitals, even travel companies. Right. All of them were significantly impacted with Covid and they were also transitioning to work from home. And so, you would often see things not working. Right. They didn’t have access to maybe systems the right way. They didn’t you know, they had to adapt, maybe their billing dates, their invoicing dates, things in which they were doing had to change. And so, our team spent a lot of time and effort making either changes to the platform, changes to customizations for the clients, configuring different features for them that they may have not utilized before. And so that was a big focus actually gave us a kind of a rallying cry around how do we help our clients navigate this and in many ways tried to defocus it about ourselves and our experience and focus on what we could do to help our clients. So, I think that helped us a lot initially, of course, we did all the financial planning. You immediately start to look and say, OK, we were fortunate. We just raised 120 million in February. Thank goodness we kept the pedal down on the fund raise. But you, of course you sit there, you look at your spending, you look at we had a plan to hire 120 new Flymates this year. Of course, that wasn’t going to happen in this environment. So, you know, you adjusted your financial plans and then you tried to navigate. I’d say we definitely played defense for probably that two-to-three-month period between March and I’d say early mid-June. And then we started to say, OK, how do we. How do we start playing more offense, right, like this is going to be a bit of the new normal for a long time? My belief is that people want to play more offense than they do defense. How do you how do you look for opportunities to innovate? How do you look for new products to build, new markets to enter? And so that’s really where we started our efforts in kind of, I’d say July and August. And again, just trying to support our people, address some of the wellness mental health issues that everybody’s facing in a stressful time. So that’s kind of how we navigated.

Brendon: [00:10:27] That’s great. Moving on the discussion to one of our favourite topics, which is around communications. We’ve talked a little bit about how the payment space is on the surface of it, not necessarily in your specific area, on the surface of it, very noisy and crowded. What’s been your approach to raising awareness and differentiating Flywire in the market?

Mike: [00:10:47] I guess a lot of other companies, they kind of go after the massive payment opportunity, right? You’ll hear companies talk about how much money is moving around the world. You’ll hear them talk about the digitization of cash. They’ll talk about these kind of massive TAMs, total addressable markets. You’ll hear them kind of talk about these huge challenges. For us We’ve always taken a slightly different approach. We look at we look at our areas. Right. Like all the money moving around the world is actually moving around the world for different reasons. And our belief is that you have to actually understand those reasons. You have to dive into the use case or the vertical or the actual problem statement you’re trying to solve. I think that’s probably one of the things that differentiates us the most. In early days, frankly, everyone thought we were just kind of this niche player who was going after the small education market and our plans were always much bigger and broader. Right. We looked and said, hey, there are certain industries that have been poorly served by payments. They don’t just need credit card capture. They actually need more software, more comprehensive solution. Oftentimes the payments are larger, they’re more complex, they’re global. And our belief was that that was part of the big reason why so much of that money wasn’t digitized well. And so, we started in education, but expanded out. So, when you when you look at that, I think a lot of people looked at us and said, jeez, let’s see if they can actually get outside of education. Can they get into other verticals? Can they get into other countries? Can they offer additional products? And so, again, we were hyper focused on the problem we’re solving and then have scaled a bit different than kind of casting this big net, this big story, even though ultimately, we’re kind of going after that same large, total addressable market.

Brendon: [00:12:24] It sounds like you’re very much on the hunt and on the lookout for those much more complex challenges that need to be fixed. That seems to be a recurring theme of what you’re talking about.

Mike: [00:12:34] Yeah, you know, and I would also say just even with even with cards. Right. Like for Flywire, probably about 20 percent of our volume is over credit card. So, if you think of, you know, 80 percent of our volume is over bank accounts. Right. Effectively, part of that is do the transaction size, the complication of the payment. Some of it’s due to just the ability for someone to put, you know, 20, 30 thousand dollars or pounds on a credit card. Right. There’s certain types of limits that a lot of consumers still have. So, again, that’s a major differentiator. Right. Most of the traditional payment processors are oftentimes merchant processors for cards. Right. Point of sale, kiosk type payments, maybe e-commerce. And so, again, we’re actually casting a much broader net and we’re digitizing a lot of things that used to go over maybe bank wires or even cheques here in the United States or paper cheques are still quite significant. So, people used to be using those mechanisms and are really starting to digitize,

Brendon: [00:13:29] Turning a little bit to explore some of the values of Flywire, I know that we touched on collaboration a minute ago. I see that that’s one of your values. How have you managed to build this, your company culture in such a fast moving, high growth and I guess global way?

Mike: [00:13:45] Yeah, well, you know, it’s probably getting a bit of a theme, but we actually had ups and downs early on in the evolution of the company. Right. Which had a spot where we almost sold the business probably eight to nine years ago. And thankfully we didn’t. And we focused on our investors, supported us through finding product market fit. And we were able to really accelerate. And I would say we picked our head up probably about maybe three years, three and a half years into the journey and realized that we had a team of about 40 and we were going to have to scale in the next part of our journey to probably triple that. And that was the moment in which everybody kept referencing how great our culture was. But we didn’t have, like the fancy posters on the walls and the motivational statements and everything that people normally would put out there. And so, I actually embarked on a program internally with Flymates, obviously contributing, which was let’s unearth what everybody keeps talking about. Right. Because everybody who visits us, our investors, bank partners, there was ‘oh You guys got a great culture, right?’ They all spoke about what they saw consistent across Flymates, even across very distant locations. Right. And I found that fascinating. And so, I like to say we unearthed are our values, right and our culture, because it was there, we just had never put words to it, and before we went and hired another hundred people, we felt like we needed to know exactly what those traits were so that we could look for them in others and kind of grow. And so, you know, that’s where, you know, things like global collaboration came from. Part of it was a forcing mechanism. Frankly, early on, one of our biggest challenges was navigating global collaboration. Right. We didn’t have the money to kind of fly ourselves around the world to see each other. And so, you kind of had to use technology the best you could, and you did have to get on an aeroplane and go see people and build those relationships because you then had to go remote again. And so, by far, one of the probably most important values we’ve had, another one that’s kind of top of mind is authenticity. Again, it kind of covers a couple of things for me. It covers a level of transparency, of directness, bringing kind of true self to work, which I think has lots of tie ins. A lot of people aren’t in work environments where you’re actually allowed or encouraged to bring your entire self to work. Right. Bring a bit of your personal life in you to let people get to know you, know who you are as well. Also, just in the transparency, I’ve had experiences in my career where you would get into tech companies and you’d have CEOs and others say, ask me any question. Right. Like, ;Oh, we’re super open and transparent;. And then the person asks the question, how much money is on the balance sheet or how many shares are outstanding in the cap table? And all of a sudden, any question isn’t quite what the person meant. And I always wanted to push that here at Flywire. And so, we’ve had this level of transparency that we’ve been able to maintain for the entire ten years. So far, so know there is truly no bad question to ask. There is no question I won’t answer to a Flymate. And that’s you know, that’s even happened during pretty, pretty challenging times. So those values, I think, have held up kind of for a while. We may insert a new one or two here and there, especially after Covid and some of the traites we’ve learned that we have inside Covid. But those are two good examples of our core values.

Brendon: [00:17:05] It’s great when you get the opportunity to take some of those bad experiences you’ve had in the past and then correct them in the future, isn’t it?

Mike: [00:17:12] Yeah, no, it’s part of the journey. I mean, we actually have this great mural that’s on our wall in our Valencia, Spain office. And it literally shows pretty much all the major milestones of the company, even ones that were not great. Right. Times in which we had to either cut staff or we had a huge amount of uncertainty. Again, I think when you read about tech, when you read TechCrunch or any of the online publications, it seems like every startup’s successful. Right? Not the case. Right. Ninety five percent of them fail. It sounds like everything’s, you know, an overnight success. It’s not, it’s a grind. There’s a lot of work that goes into building these companies. And I think, you know, I think there is value to actually focusing on where you didn’t get it right. And I think people believe that when you’re able to highlight those things, I think you’re human, first of all. And I think the second part is, as you said, you learn from them and you avoid that rock the second time around.

Brendon: [00:18:06] That’s cool. Side note, I’m actually sat in Valencia, in Spain, that’s a cool place to have an office.

Mike: [00:18:14] Amazing spot.

Brendon: [00:18:15] Yeah, brilliant. And then I think just another area that struck us as you being quite forthright is around your commitment to diversity, equity and inclusion, obviously very prominent issues at the moment around the world. I’m just curious to get your perspective on what you think the role is of business in driving the agenda and how can companies like Flywire make a difference?

Mike: [00:18:43] You know, it’s obviously a critical, critical thing on the mind of so many people. For us, again, having a value around authenticity. It’s been something we’ve tried to push for a long time internally, right. Of, hey, we want a diverse group of Flymate’s. It’s naturally diverse just with the geographic footprint of the company. At the same time, every one of our offices has a diversity challenge, something they’re looking to improve. Right. Whether it’s maybe it’s our tech team’s gender composition, maybe it’s a certain type of religious diversity in a certain geographic part of the world. You know, maybe it’s the male to female ratio in our sales team in a certain area. So, there are all types of, and I think every company has those types of challenges. And the key is to how do you start moving forward? How do you start improving those numbers? How do you set goals, hold yourself collectively as a team, accountable for those goals around diversity? And one of the biggest learnings, I’d say, in the last few months for me has been the power of the team. Right. If you unleash a team, we have a great group called Flymates First, our Diversity and Inclusion Team, volunteer team of Flymates who are passionate about those types of topics and that teams actually helped navigate us through a lot of different decisions recently. Right. Of, Hey, how are we going to look at our KPIs, right, in what markets, how do we capture Our KPIs around diversity, what’s OK to ask in certain regions? And what is not OK to ask in certain regions? How do we make sure we’re looking at diverse talent pools? In some ways it isn’t rocket science. If you keep finding the same types of people, you’re likely looking in the same type of spots. Right. And so how do you broaden out your networks and actually target different pockets of talent that you may not have found before? My experience over the last few months is that it doesn’t take much. Right. Even if you go in and start, you know, go follow five or 10 people that maybe aren’t in your normal circle geographically or religiously or industry wise, and you will start to see pockets of information on places like Twitter and LinkedIn that you’ve never seen before. Right. And pockets of talent that you can recruit from. And so that’s been a huge learning. There’s a long way to go. Unfortunately, I think it’s still a generational issue. I don’t think there’s an overnight fix. I tell my team often that it isn’t about tweeting hashtags from your couch. It’s actually about getting out there, looking at what you’re doing every day, making change, having an active role in that change in the community as well as in professional life. One thing that we did to help Foster that is, we actually created two things. We call fly better days. I mentioned we’re good on branding, but again, in parts of the social injustice, unrest and racism issues that have happened in the world, like, it just became overwhelming to so many people inside the company and outside. We just said we’re going to create two paid days. People should go give their time and their efforts to causes that they care about. Right. So, it allowed Flymates to go out and potentially participate in a peaceful protest. It allowed them to maybe focus on getting people out to vote. Some people use that for all types of different causes, children’s groups, etc. And again, it was a way to say, hey, we can put money where our mouth is. If you will, and say you have two paid days. We know our Flymates want to do these things. Sometimes they don’t feel they can step away from work. And so, we encourage them to do it, to take a picture post it in the slack channel, share what they did. We’ve had a great response with that. And it focuses, I think, people on take action. Right? Again, don’t just talk about what we hope the world will be. Let’s find ways we can actually go out and start making it that way.

Russell: [00:22:16] That’s a great initiative. Just building on this element, around internal comms, because you’re talking about speaking with colleagues, or Flymates, as you call them. How do you balance that need, though, to talk to individuals and then teams and then the whole company as well, especially given at the moment, well, you’ve talked about how you’ve grown the team as well. So, there’s obviously a lot more of you now than there was a few years ago, we’re geographically spread and also, obviously with people working remotely at the moment, so that adds a few levels of challenges in there as well, doesn’t it?

Mike: [00:22:48] Yeah, does. I mean, I used to probably spend 150 thousand miles a year in the air and much of my executive would as well, and it would be very common to be in a flywire office in Valencia and see people from our Singapore office or Tokyo office. And that was just kind of commonplace. Obviously, the pandemic changed that. So, we’ve had to get more creative. I’d say we’ve probably tried three different formats of all company meetings because everybody is on these video conferences so often. How do you not take up more and more of their time to communicate the information when they’re constantly on these conferences to do their jobs? And so, we’ve been recording short videos, trying to give people bite sized content that they can consume throughout their day, or sometimes people even catch up on them over the weekend. So, it gets information out there without forcing people to sit there and listen in a forum so we have been trying things like that. I’ve been known to drop a zoom link in a slack channel of a couple of hundred people and say, I’m on this zoom for the next hour if anybody wants to drop in. And things like that, I think create a little spontaneity in a world where I guess serendipity may be gone for at least right now, everything seems so planned. Those are some of the things we’ve done, again, trying to create pockets of socially distant activities that people can participate in if that’s acceptable in the region in which they’re in, giving people we give people a stipend so that, hey, go find a Flymate, get a coffee. Right, go, go get it. Go get a drink, go order pizza and go to a park. Right. Those kind of things to try and encourage people to get together. Even if you couldn’t get together with large groups. We even pulled off a pretty crazy thing, I think it was, jeez, two weeks ago. We sometimes rent locations for retreats. Right? And we had a place that had twenty bedrooms. It was actually in the state of Maine here in the United States, about two and a half hours north of Boston. And we delayed it because we couldn’t actually go there during Covid. Delayed it ’til September. And we were going to we already put our money down. We didn’t have anybody that was going to use it. My executive team was distributed around the world so we couldn’t get here to use it and we decided to open it up for Flymates. And so we called it the Fly Lodge and. Here was a 20 thousand square foot house with independent bedrooms for anyone that went, you had to get Covid tested before you could go into the house effectively. And people loved it, right. They actually got a chance to see people again, work through the week, just have a different experience, and actually gave us an idea that we hadn’t thought of maybe months before, but maybe trying to replicate it in different parts of the world where we can’t maybe cross borders. But within certain regions there’s acceptable practices. There’s ways in which you can get tested, ensure safety of everybody. So, we may try something like that to help keep people engaged. But, yeah, it’s not easy. You know, people do miss community. And I think, frankly, the future of work isn’t going to be staring at the screen. There’s going to be some return to some level of interaction, even if it’s not the level of commuting and challenge we all had in just dealing with the old world.

Russell: [00:25:57] Tremendous. And what about your role as an external spokesperson and representative of the business? What’s your view on that? And what have you learned along the way in the 10 years of Flywire?

Mike: [00:26:07] It’s not something that everyone always asks. Are you an extrovert introvert? I’m a massive introvert, actually, and everybody’s often surprised because I think I’m good at, I think, faking it. But my level of interaction at a certain point, I kind of need the downtime and the focus. And so, for me, being the external spokesperson has been something I’ve had to kind of grow into and realize how to kind of navigate just with my own personality. What I would say is I absolutely love the industry, that I’m in, I’ve been in tech for 20 years. A lot of that in payments, in tech. So, building up that network has been amazing. Right. Obviously, we have a lot of great partners. We have some of the top banks in the world that are partners, the city banks, Deutsche Bank, Bank of America, Barclays, those types of folks. We also have MasterCard, Visa, American Express, Union Pay, Alipay, PayPal. So, you have these amazing companies who have been so good to us over the years and supporting us as we’re trying to do something new and different. And so, having those relationships and getting to interact with those companies, talk about partnerships externally and stuff has been great. And again, I’m a big believer in culture. I’m a big believer in people need to be working on things that they’re passionate about. And if you’re not passionate about it, go find what you’re passionate about. So, I love talking about the culture we’ve built, how companies can adapt and be a little more employee focused, try and focus on things that I’m most passionate about, even if it’s not my core default behaviour.

Russell: [00:27:37] What would you say has been the biggest challenge you’ve had then?

Mike: [00:27:39] It’s probably been the pace, right? So, I’m competitive in nature. I’m actually a father of four boys, so it’s constant competition everywhere around my house. And so, frankly, the pace in which I often ran before was probably too fast and too much, especially when it came to global travel. I’d hop on a plane for an hour meeting on the west coast of the United States. and I think so many of us did, but it would just be a constant grind. You know, I remember one trip where I think I hit Boston, Tokyo, Singapore, Cluj, Romania, Valencia and London within a ten-day span. Right. And so that’s actually really challenging to do. And I think I think I was on an aeroplane, slept on an aeroplane like four nights or something. So, like, those types of runs were just crazy in hindsight. Right. I didn’t get enough time in any location and I should have split it up. But again, I was doing it so often that there was just kind of a constant wheel that you felt like you were on. And so, I would say that was by far the biggest challenge, right. To now I think reflecting back, I would definitely do it different. Right. I’d go and spend a week in Singapore. I mean, I’d do it four times a year, five times a year, like I normally would have done. But I’d have longer trips that probably I could put more activity around with the people in those areas.

Russell: [00:28:55] And what about communications challenges? What would you say that the biggest one of that’s been for you?

Mike: [00:29:01] Sometimes I’m probably overly transparent. You know, I’m really realizing, especially as the company’s getting bigger, there’s a lot of folks who may not want to know all the detail, you know, almost constant level of decision making that the executives and I have on a daily basis. Some of those decisions are hard, right? If you look at just the pandemic, right. You have uncertainty, right. People want to know what the future of work is, for instance. And I tell Flymates, I can’t tell you what the future of work is like. I can’t mandate it, right. That’s the wrong answer. I can try, but it’s the wrong thing. Our engineering team may need a different future of work than our sales team. Right. And so, part of it is about us figuring it out together. And so sometimes I think being that direct and that transparent may actually sometimes push these complex decisions onto other people that don’t necessarily want them and show a level of uncertainty, even though I think that’s the reality of the world. And so, I’d say that’s the balance for me. I know other CEOs who just go in and say, hey, this is the future of work. This is what we’re doing. This is how we’re going to be organized. And to me, it’s just too simplistic of an answer. Right. And so, I try and convey that. But at the same time, some people may see that as pushing the challenging topics onto other shoulders, which isn’t the intent, just an aspect of transparency.

Brendon: [00:30:13] You need to confidently talk about the uncertainty.

Mike: [00:30:16] Yeah, that’s exactly right. Yeah, that’s the balance. I’m trying to figure out.

Brendon: [00:30:20] Just staying with communications. Has anyone ever given you any great advice that you would want to pass on to someone else because it’s made a real difference for you as far as communications is concerned?

Mike: [00:30:30] So I have a chairman. He ran major divisions of American Express for years. He’s on the board of a number of tech companies, Betterment, Yoyo Wallets, Remitly, Flywire. He has a way in which when he’s talking and oftentimes you know, think of the CEOs that he’s on the board of their companies like myself. They come to him with these ridiculous challenges, problems, complex things and his ability to reflect like first pause and then reflect, like most people want to jump in with an answer. And that’s my default behaviour too it’s like, you know, you throw a huge challenge at me and I’m going to start answering it or giving you direction, which drives my wife crazy as well. Right. She’s obviously, sometimes I just want you to listen. Right. So not try and solve every problem in. My chairman does a great job where he will often reflect and he’ll actually pause a conversation and he’ll say, you know, let me reflect on that. And he’ll take 30, 60, 90 seconds before even uttering another word. And then he’ll come out with an actually well thought out, well-articulated point. That’s been that’s been something I’ve been trying to leverage more, because I think the default, especially in tech companies and start-ups, it’s to fix stuff. It’s to change stuff. It’s to try stuff. And so, you’re kind of like, maybe shoot first, aim second. And when it comes to communication, sometimes if you just take that pause, if you really think through it, you can actually organize your thoughts in a better way. So that’s something I’ve been trying to work on a lot more.

Brendon: [00:31:59] That’s great advice.

Russell: [00:32:00] Yeah, brilliant. Mike, we’ve got one final question for you. It’s a question we’ve asked all our unicorn leaders on these interviews. If you were to go back in time and speak to your old self, what guidance would you give about communications and what steps would you encourage yourself to take in order for you and your business to excel in communications? And like your chairman, you can take 30 seconds to think about it if you want!

Mike: [00:32:25] I am going to take a minute to think about it! What I would say is it’s tied to communications when you’re communicating, it’s so important to understand who you’re communicating to and how best to get your point across to that person. And one thing I’ve found in the last 20 years in business has been people are barely able to understand themselves what made them who they are today, how they were brought up, the challenges they’ve faced in their life and the more you can understand about that and who they truly are, what gets communicated to them, how do they react to information? What’s the best way to interact with them? Like those types of things are actually really personal. And oftentimes I think people have broad communication strategies, right, where they try and do the same thing to different people. And so that uniqueness of an individual I think is really, really important. You know, I have some execs who, my walk in, random, one on one, no agenda, sink up that goes 90 minutes every two months is like all we need to connect. I have other execs that I work closely with who if we miss a checkpoint every five days, our relationship’s off the tracks. Right. And we’ve got to get it back. So, I think oftentimes people think of communication as kind of, you know, I get to decide it. I’m the communicator. I’m the person communicating. And the reality is it’s kind of a two way, two way street. Right. It has to work for both parties for for the relationship to really be great.

Russell: [00:33:49] Tremendous. Really enjoyed this one. Thank you so much. Mike Massaro. Thanks for joining us online to chat

Brendon: [00:33:55] Thanks, Mike.

Mike: [00:33:57] Russell, Brendon, thanks so much.

Russell: [00:33:59] Wow, Brendon, the first of our unicorn leaders from North America, thoughts on what Mike had to say and maybe comparing it to all the discussions we had with our European unicorn leaders.

Brendon: [00:34:09] I mean, I thought it’s really fascinating just to get a sense of everything that’s going on within the payment space and how Flywire is really sort of zeroed in on some of these more complex areas. But I think in terms of chatting to Mike, I think what impressed me and made a real impact on me is how thoughtful he’s been about everything that they’re doing with the business. And you pick up a real tenacity and focus about everything that they’re doing, whether that’s for customers or whether that’s for employees. I just think the combination of that thoughtfulness, but then that’s kind of like tenacity and focus in the execution of what they’re doing really shone through for me.

Russell: [00:34:48] Yeah, yeah. It’s going to be interesting interviewing our North American leaders moving forward.

Brendon: [00:34:54] Yeah. I mean, it really will be interesting. I imagine after we spoken to a few people we might be able to draw some good conclusions. I can’t say that at this particular point. I’d want to make any sweeping generalization.

Russell: [00:35:07] No, not at all. Well, that’s actually it for this latest episode of Unicorn interviews with Tyto. if you want to find out more about Flywire, then their website is very simply flywire.com. And we’d love to hear your comments on today’s chat and can share those on our Facebook, LinkedIn, Instagram or Twitter feeds. They’re all linked from the top of the website at csuite podcast.com, where you’ll also find all our previous shows and supporting show notes plus links to where you can subscribe for automatic downloads of each episode via the likes of Spotify and Apple. And if you’ve liked what you’ve heard, then please do give us a positive rating and review. We’re also available on all podcast apps. Just search for the csuite podcast and hit subscribe. Don’t forget, you can also subscribe to the Without Borders podcast from our partners at Tyto and all the details for that are on their website. Just head to TytoPR, and click on the podcast link in the top navabar. If you are a unicorn leader yourself and you’d like to be part of this series, please do get in touch with us via the contact form on the website and of course anyone can get in touch with us using that form and give us any feedback they may have. You can also reach me via Twitter using @RussGoldsmith or find me on LinkedIn. But for now, thanks for listening and goodbye.

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Tyto brings you Without Borders, a regular dose of inspiration for passionate communicators, courageous creatives and entrepreneurial business brains. Expect candid chats with the wisest old hands, bleeding edge innovators and left field thinkers and doers.