John MacIlwaine On Raising $50 Million To Create The Most Modern Payment Card Platform

After years of growing some of the most well-known financial and technology brands, John Macllwaine decided to take the reins of the future with his own fintech startup. His company, Highnote has attracted funding from top-tier investors like Westcap, SVB Capital, Renaud Laplanche, and Costanoa Ventures.

In this episode, you will learn:

• The thesis for Highnote, and how they are empowering businesses
• The vision for the future of payments
• Rebranding
• Fundraising strategy
• John Macllwaine’s top advice for other aspiring entrepreneurs

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About John MacIlwaine:

John MacIlwaine is a senior business and technology professional with 25 years of experience in executive-level GM/CEO and CTO/CPO roles, primarily within the financial services industry. His expertise in technology innovation, strategic vision, implementation execution, and operational excellence in both early stage and mature companies are commendable.

John is a seasoned general manager with significant people leadership (1,500 staff) and P&L responsibility ($195 Million). He has acquired a reputation for building high performing global teams (India, Singapore, Philippines, US) and operating effectively in diverse corporate cultures across industries and geographies

John has well-honed client management and executive presentation skills; collaborative business partner and thought leader; outstanding analytical and problem solving abilities; and is able to deliver quantifiable results that meet or exceed objectives

Connect with John MacIlwaine:

• Crunchbase
• LinkedIn
• Twitter
• Facebook

Read the Full Transcript of the Interview Here:

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Alejandro: Alright hello everyone and welcome to the deal maker show. So super excited with our guest today. We’re gonna be talking quite a bit about scaling organizations and then also the entrepreneurial journey. So I guess without furtherdo let’s welcome our guests today John mcowwain welcome to the show. Welcome.

John MacIlwaine: Hey thanks a lot Alejandra great to be here.

Alejandro: So let’s talk about your upbringings and doing a little bit of a walkth through memory lane. How was life growing up in Ohio.

John MacIlwaine: You know life in Ohio is it’s a great place to grow up and I quickly left Ohio and went to Michigan up north and studied computer engineering there and then took a big jump and moved over to London for a couple years and um and got involved in. Financial services and technology and but it was great. Ohio is a fun place and and so is Michigan by the way so that’s where I went to school well at an early age I um.

Alejandro: And how did you get into computers.

John MacIlwaine: My dad bought me 1 of the very first Apple computers which I don’t know is right behind me here in this podcast at Apple 2 plus and I was really excited about being able to engage with technology and a computer and started up and actually a business when I was very young. Um. Using the computer and I just was just fascinated by it and and um and continued to be um, excited about gaming and business and a lot of different you know technologies as they emerged but it all started with this this Apple two plus air

Alejandro: And in terms of really getting into computers but more specifically financial technology I mean why out of all things financial technology because I mean it sounds like it got you hooked and you’ve been you know around you know fintech you know since since the 90 s now. So.

John MacIlwaine: Yep, and I’ve been fortunate to have seen here and and worked in a number of different sort of segments of of financial services from from brokerage to payments to asset management and wealth wealth management to credit and lending and you know I’m just. Really excited about the sort of the pace of innovation that occurs or or um can occur to change in business models and to emergge and to allow different innovative ideas happen all through. Technology and product and so it’s really about the pace of innovation that’s excited me most about financial services and technologies and then and then you know beyond that it’s It’s the ability to to unlock new business models and and do that in ways that help people and help businesses. Grow and and differentiate and be successful and it’s it’s that connection between the the product the technology and and the customers that I found to be very rewarding and exciting within within financial services.

Alejandro: And in that in that in that sense the first company that you worked at was ended up being acquired by Morgan Stanley so I think that to a certain degree. Also he gave you access to what that full life cycle looks like and that integration process. So what did you learn from that.

John MacIlwaine: You know you’re right? It was really about the the notion that not knowing everything about a particular industry is sometimes a benefit because I think had we known how maybe difficult or challenging or how. Um, much of the infrastructure did not exist within um within the brokerage environment. You know I don’t know if we would have decided to tackle it it was it was more of a hey why can’t we do things differently and and and what is it about Um, this legacy infrastructure. But as preventing it from being modernized and so as an example with the brokerage business. We we really looked at connecting Apis between the internet and the stock trading floor if you will and it turned out. There were no apis that existed to to allow us to do that and so you might think well Gee. You know. Sounds like that wasn’t going to go very far but no you innovate around that you figure out a way to create um innovations that allow for the businesses to exist and that’s that’s what we did. We start off with. You. You know? so you know wrapping some legacy technology and then we we worked with companies that had apis and integrated with them and you know over time that type of that innovation and and looking at things differently was was really the key and 1 of the biggest lessons learned was you know don’t don’t take things for granted things are are the way they are. You know, not necessarily for the best reasons and um and thinking about those challenges and then actually innovating and and maybe the answer is not. You know the the ultimate this is the way it should be done but you can go through different iterations and different pieces and and different ways to get to the. The end goal some of its manual some of the innovation we did with the brokerage side ended up being manual and you’d think well, that’s not really online brokerage but that was the exception case and then you you modernize and you automate more and more and more and more and eventually. You have an end-end system which was ultimately but what we built and and and then we’re acquired by by the bigger company. So lots. Lots of lessons learned there.

Alejandro: And in terms of worldview I’m sure that is changed a little bit on your shape of thinking because I mean you’ve worked in London as you were saying then Chicago I think California I mean pretty much all over the map I mean how how do you think that that has helped you to really.

John MacIlwaine: Um.

Alejandro: You know, gather or gain you know access to a different way of seeing things.

John MacIlwaine: You know it’s a great question I think there’s a lot of different things to unpack there I think there are certainly cultural differences you know between you know you know international businesses and and but beyond that there’s regulatory issues and concerns that that you need to learn. There’s. Um, infrastructure and the the way in which markets work in different areas is different and so it it gave me a broader perspective around what you need to do to to so really build a global company and working at Visa which which was obviously ah ah a global business. Kind of understanding even the idiosyncrasies of cross-border messaging and settlement and currency and as well as all of the regulatory issues. You know, really sort of broadened my horizons if you will and in in terms of how to think about building a business that. Eventually is a global business but but not being so naive to think that it’s it’s easy to do or or it’s just ah, you know it’s not a technology problem per se There’s a lot more that that’s required to um to take into account. Having said that you know I think payments is a global business and um. The interconnectivity between different markets and um, you know different customers that are sometimes overseas and and want to still have access to everything they expect with their digital wallets I mean those kind of thinking that that kind of capability is really. Um, becoming more commonplace and expected and so as a result you know it needs to be part of the thinking in the early days of I think any any payments business that’s um, that’s getting out of the gate.

Alejandro: Now You’ve been involved with pretty big organizations. I mean you are alluding down now to visa. But also you were part of lending Club Braintree I mean you name it now one of those experiences that I thought it was really interesting. It was the experience of lending crop now of lending club Because. Lending Clubbe You were able to really experience that fastpa and that Rocket ship Environment. So What kind of culture allows for that to happen. So.

John MacIlwaine: Yeah I think I think the the exciting part about lending club when I joined was was just the thinking that we could build you know a new business model a new way to borrow a new way to lend and it’s at a good example of kind of setting out on a certain path. Um. And and designing and implementing products and solutions that that may not um, you know may not have been exactly where where where we ended up and so I remember when I joined that there was such um, such rapid growth in adoption in that business that you know we were even having you know. Quite a bit of of scalability and and challenges and processing all of the loans and and doing the sort of the nightly reconciliation and um I remember you know a couple a couple of times where you know we weren’t sure we’re going to be able to even complete the processing and and those are pretty those are pretty eye-opening. Um, you know so stay up all night and and figure out the problems but I realized that if you’ve got if you’ve got a great team if you’ve got you know people that are dedicated and focused. You know those types of of technical challenges. Um can be can be overcome, but but you know. It’s the exciting time of being in ah in a rapid growth company. But but it’s it’s not always smooth sailing and and it’s really about looking at challenges and and solving them with great teams and and 1 of the bigger challenges. You know, even later on at at lending club was not necessarily technical but we had a um. You know a departure of our Ceo fairly abruptly and um and that really exercised a lot of sort of leadership and and really ensuring that um the the business. The company. Teams could continue to carry on because we had built something so great and so navigating through that was another. You know another challenge that you know I learned a lot in terms of yeah who’s with you and and who who’s behind the vision in the team and and who’s willing to forge forge through and it was really It wasn’t a great experience but it was a great learning experience in terms of how to deal with some of you know some of the challenges that are you know across the board. So sometimes happen when you’re building and and watching great businesses.

Alejandro: Because how many people were there when you joined lending club on how many were when you were leaving.

John MacIlwaine: Yeah I joined when there were about 50 people in the company on the early days I joined as the chief technology officer and built built built up the business grew the teams and then I left in total we were about. 131400 people at the time that I left post ipo so we had built built the business rate raised capital went into the public markets had a very successful ipo and then I stayed for a year after that so lot lot of great experiences. There.

Alejandro: And in this case, you went to Braintree and Braintree was the ultimate last immediate step to building your own business. So how was that how was that like yes.

John MacIlwaine: Ah, bridgetry was great and braintry for those who may not know is the sort of the acquiring business within Paypal and so it was a company within a larger company really focused on implementing technology for payment acceptance and so that was my. Ah, so I joined Braintree as the chief technology officer and and also chief product officer and that was an exciting sort of learning experience in terms of working with super smart people in the payments business people that have really kind of really understand how to build. Um, cuttingedge gateways and and scalable technology platforms and understand developer experiences and what’s required to launch not only small and growing businesses. But but some of the largest companies in the world we using um and still are using brainstree as an acquiring business. But I think the biggest thing I learned when I was there was when I was promoted to Gm or or Ceo basically general manager of the entire brainy business. So full accountability of of the p and l and having that perspective around. Globalization as we talked about earlier and because but brainree is a global business and really understanding where some of the pockets were of opportunity for braintready compete with some of the other requires and continue to move fast within a large company and and how do you how do you move you know how do you continue to innovate in. Um. Within a larger company because let’s face it. You know when you get to a certain size. Um, it can be difficult. There can be obstacles to innovation and you know you know my entire career has been a bit of a combination of of smaller organizations where we’re moving fast but but also I’ve worked at large companies as you mentioned and. For me, it’s been about figuring out how to continue to innovate to hire great people and and and to push the forefront regardless of whether it’s a large company or a small company and so braintree was a mix of sort of a a small ur company within a larger company and so that was a. Great experience and learned learned a lot about the acquiring business learned a lot about international and global payments more than I had at visa um and sort of got the um you know got got the wheels turning if you will in terms of what’s next and and um. But some of the opportunities were for for a new business.

Alejandro: Now in this case, let’s talk about high note then you know at what point that’s the idea of high note come knocking and and what was that moment where you say you know what I think I’m gonna I’m gonna go for this one.

John MacIlwaine: Well I think ah when I had left Braintree and and Paypal I was still pretty excited about the the payment acquiring space and the opportunities in terms of pockets of of sort of opportunity that I saw as as gm and where you know where. You know innovation still was was sort of yet to meet some of the some of the customer demand but as I got sort of deeper and deeper into you know what was happening within payments I became particularly interested in issuance and and this notion of instant issuance or virtual issuance. So. Allowing companies and businesses to pretty much immediately gain access to the payment rails and and to actually do things that are more innovative than the traditional sort of plastic card issuance or Cobrand issuance where if you’re a business and you know you want to put your brand on a card and. Launch that to your customers and and I think historically those types of models were reserved to some of the largest businesses whether they be airlines or you know major hotel change but with this onset of of kind of capability with instant issuance that became exciting to me because I felt like. With the the world of embedded finance and the the amount of innovation occurring with different business models such as you know uber and and doordash and um, you know, ah other fast-growing businesses that are requiring a slight twist or slight innovation around. Um. Card products and embedded finance that was exciting to me and when I looked at sort of who was out there providing these services. It. It felt like you know there were there were some businesses in this space but but lots more opportunity and if we could think about how to build something for purpose and really built for today’s sort of challenges but also for for the future and and create a platform that looks at processing or issuance more as a product construct than a kind of a back-office you know churn through a bunch of cards and transaction really about how do we move the innovation into the platform side as a product and that’s that’s ultimately what. What we decided to do was build a full stack meaning n top to bottom. Um, issuer processing platform but build it in a way that would allow our customers to innovate because ultimately what we found as we went into the market is there are solutions that that can perform issuance. Obviously. But the ability to allow customers to be differentiated to do things differently to separate themselves from the rest of their competitors and to do it faster than um than what some of the solutions out there would allow for it was that combination of of sort of differentiation and speed to market.

John MacIlwaine: Where I thought the opportunity was and so to address that I think you really have to think about the architecture of the platform. The the notion of you know 100% Apis and and really not trying to build a platform with a bunch of features but build a platform that was enabling that would allow. Customers to build with us and innovate features because I always think that you know customers build the best products not not businesses and it’s really about the connection between customers in certain verticals and understanding. What they need now and where they’re going and be able to have a platform that’s nimble that can react that can scale that can support all of their needs in the future and that’s that was really the idea behind behind high note.

Alejandro: So then in terms of how you know and so that the people that are listening get it. What ended up being the business model and how do you guys make money.

John MacIlwaine: So the business model we are a a again, a full stack card issue. So we issue cards to our customers. We’re a b two b company. So we partner with businesses that want to create their own card products whether that be virtual or. Or a plastic physical card. We we handle everything we’re we’re sort of a full program manager. Um, and but we handle all of the regulatory and compliance and and integration with Bank Partners all all of the capability that a business needs we handle that. But allow them to innovate customize differentiate and extend their brand within payments within embedded finance or card issuance and our business model is around similar to most business models which is we we make money when our customers. Um. Um, have successful card programs and card products where where there’s volume where there’s spend on cards where there’s innovation on on increasing stickiness with the customer experience through through spend and that comes through. Through interchange basically in terms of that model. That’s that’s really what our business is based on.

Alejandro: And in terms of the you know shift for you because I mean up until now since the 90 s I mean you’ve been really on the tech side either as a cto or hit a product but now you’ve really shifted. No, you’ve done like a one eighty on your on your approach of of really you know going about the operations or your or your routine and and now you’re on the business side. So how hard has it been really going from the tech side to the business side for you. Jeff.

John MacIlwaine: Yeah I mean for me, it hasn’t been that hard because I’ve always been sort of grounded by business models and customers and and I think that that technology for me was sort of ah a means to an end. It was a means for sort of understanding. What are the opportunities. What is the actual business but also grounded by. You know what what are the possibilities what can be done and what are certain ways and so I think it’s ah has been a sort of a unique combination of my passion is really around. You know. Customers and and unique business models and unlocking innovation. Um, but but as you as you rightly point out a lot of my experience has been kind of owning that being accountable for the delivery, the execution and I think certainly in payments I do think it’s important to in some regard be grounded by. By both the technology and and the product but but also kind of where where are business is going where do they need to go and and therefore how do we put something together that is not a reflection of where things are now but really sort of the culmination of where things are headed manifested in ah in a platform that. Um, can help all these businesses grow faster. so so I think it hasn’t been ah ah necessarily a pivot. In fact, I was gm at at Braintree so I did have full full accountability for for p and l and operations and and product and engineering as well. And so so that was a kind of a natural sort of leap and and foray into into high note and a chance to sort of. Do it. You know from scratch with a team that I think is the most advanced team and in payments and in the us ever assembled and um and the ability to sort of continue to execute and and innovate um around this area has has been I think a ah you know a demonstration of. Ah, the kind of the team that we put together and interca continue to grow.

Alejandro: And you guys have gone through a rebrand not long ago and I know for a fact, you know personally that that can be painful So so was it that challenging for you all.

John MacIlwaine: Just with this. Yeah, so we started the company in the seed stage with a placeholder name called called Bay One and that was ah an old company that I had during the lombard days that was acquired and we sort of sort of repackaged that just as a place sort it was it was myself and my co-founder kin key. And a few seed members and we decided you know, let’s let’s get the business off the ground. Let’s build some technology. Let’s let’s understand where the market is and we’ll we’ll figure out you know what? what the brand is later and so we we made the decision to rebrand before we had really emerged from. From stealth if you will so for us it wasn’t super painful. We hadn’t done any marketing people were really knowing who Bay One was but no, you know, no major customer sort of conversations I think at that point and so so from that perspective. Um, you know the Rebrand wasn’t. Particularly complex I do think that high note is ah is a great powerful brand. It has a positive connotation sort of you know, end your podcast on a high note. Um and I think it’s easy to say easy to spell and easy to remember and it’s it’s quite different from anything else. That’s out there and so it allowed us. Kind of as a team as we had 30 or 40 people in the company to to together kind of rally around you know the notion of this is our identity. This is what we need. This is what we’re bringing to market and so we emerged from sort of stealth in ah in ah in September of 2021 with the high note brand. And um, you know it’s been great ever. It’s been great. Great well received and um and we’re all excited about it.

Alejandro: And and in terms of capitalizing the business I mean how how did you guys go about capitalizing this business.

John MacIlwaine: So in the early days we um, you know we were you know conceiving of this idea around issuance and and building a platform and so we ended up raising a seed round with a couple of investors and and you know our seed round was you know. Perhaps a little higher than most seed runs was about Eleven Eleven and a half million dollars and I wanted it to be that amount or near that amount because you know building a payments business from scratch is is somewhat unlike you know, many startup or early stage businesses where you know you you you seek. Some amount of capital whether it be 2 3 $4000000 you build some technology. You do a product market fit you test you innovate you pivot you you know you meet some more milestones you you know, go into the market for additional funding and there’s nothing wrong with that model. That’s a great model but within payments you you can’t you can’t sort of. Build ah, you know a minimum viable product. You have to build the full stack. You have to build you know integrations with with the networks you have to build integrations with the banks you have to build the platform with the vault. It has to be secure. It has to be compliant and so. And you have to you have to hire great people and so we felt like the past should be let’s let’s have enough seed capital so that we can get this thing launched with great people and get the partnerships in place. Um, and go from there and so that’s so that’s what we do and so it’s eleven half million dollars and then six months later a couple of the existing investors. I think you know we’re very excited about the progress that we’ve made and becoming more and more convinced that you know given the landscape given the competitors given the addressable market given the size and given you know the team’s experience in in delivery that this was going to be a big um, ah. You you know a big opportunity and so we had a preemptive series a around and we raised an additional forty forty some odd million dollars which you know allowed us to continue to grow and and and and then emerge from stealth and and kind of that’s where we are now.

Alejandro: And what does it mean preemptive and what what does that look like.

John MacIlwaine: Well, it wasn’t I wasn’t sort of we weren’t in fundraising Mode. So I wasn’t going into the market I wasn’t approaching venture firms looking to raise Capital Um, and so it was more of it sort of an inbound. Um, let’s get ahead of you Know. Series a and we’ll just we’ll just fund your series a earlier than you may than you may have been may have been looking for and so that’s what preeptive means.

Alejandro: Now in this case I mean for you guys, you know what on what a while ride you know I Guess the the the question that comes to mine. Is you know if you were to go to sleep tonight and you wake up in a world where the vision of high note is fully realized what does that world look like but.

John MacIlwaine: Ah, look We have pretty pretty. Um, we have pretty audacious and ambitious goals and I think that the the the company is starting off in the issuance space. But I Really believe there’s an opportunity for us to deliver a. Sort of the de facto platform for businesses that want to work with the most modern technology platform product out there that will allow them to launch card product acquire transactions um across a whole spectrum. Ah, extend Globally um, participate in in a lot of the global payments markets. But but really a platform that is about customers. Not not about high note. It’s It’s really about providing capabilities that you know many businesses can’t even envision right now because they’re not fintech or they never thought they would need. Ah, card product or they’re happy with their existing legacy provider. But when you start looking at how innovative these types of products can be and and how necessary they are to offer an integrated financial experience to your customer because the demands of you know. The next generation on on customer experience and digital wallet and Cross-border Payments is continually rising and so I think you know being able to step in and offer that capability and those capabilities now and in the future is really what. You know I would love for for high note to um, be known as you know overtime here and that’s what we’re building towards.

Alejandro: And I guess as as you’re looking back. What do you think? took you so long to become an entrepreneur.

John MacIlwaine: You know I’ve asked myself that question. Um I think I think a lot of it is confidence. it’s timing it’s um you know it’s it’s not an easy thing because I I’m having so much fun here and and building the team has been just great I love the first experience with lumbard brokerage. But I think to some degree I think I needed to go through the journey I really felt like the the experience that I gathered both in the the domain of of financial services and payments. But also you know as a leader and as an entrepreneur and as a business leader. Sort of there is a lot to be said about the experiences, both highs and lows that that you get along the way and I think that that’s sort of brought me to the point where you know there was no way I was going to go work for for someone else. It was really about this is the right thing to do and this is the right time for me. And I’m not sure what it would have looked like if I tried to do it five or ten years ago but we can’t go back in time. So here. We are.

Alejandro: So let’s say you were able to go back in time John and today I put you to a time machine and you’re able to ask that then or to share with that younger John with your younger self one piece of advice before launching a business. What would that be and why you and why you know now

John MacIlwaine: Um, I think you know I think yeah, you know some advice was given to me later in my career I don’t know in my thirty s maybe that I wish I had had you know when I was 17 or 18 or 19 and I I’ll just I think about that a lot because I think it kind of um. It makes me think about um but about the journey and so the the advice was around you know in an or in the early days when you’re getting your career off the ground a few things one you know, primarily you know, be brave and and don’t be afraid don’t be afraid to take risks. And and certainly don’t be afraid to make mistakes and and then in conjunction with that stay sensitive to other people and and I learned along the way that kind of you start off in your career and it’s it’s about it’s about me and it’s about how can I do things and how can I contribute and how can I be a better. Ah, better leader but in reality and you learn and some leaders learn this very very early on and some leaders learn it later on it’s it’s really about the people and the team and the success of the experience around surrounding yourself with great leaders and great people and. Learning how to recognize great leaders and great talent and great people and and you know that’s not always so straightforward. So the the idea around stay sensitive to other people and and then from a confidence perspective. You know if you can build that strength sort of if you can build that strength inside you then. Then the outside world is is going to respond and and that’s really um, been evidenced I think in my personal journey and um I think I I would have hoped that I intuitively thought that when I was younger, but but really sort of if I went back in that time machine and and someone said no no, this is you know this is really the way to. To sort of think about things and and keep your eyes and ears open and that’s that’s probably what I would say.

Alejandro: Very nice now for the people that are listening John what is the best way for them to reach out and say hi.

John MacIlwaine: Yeah I think Linkedin is always a good way. It’s it’s it’s open and I’m on it every day and and that’s probably the the best way to to connect in and would love to hear from people and would love to share more about what we’re doing here. We’ve got a great business. Great great company and we’re obviously hiring ah people across the board. So. You know you’re excited about you know, joining a fast-moving innovative company where we’re having a lot of fun and making a big difference then please reach out.

Alejandro: Amazing. Well John thank you so much for being on the deal maker show. It has been on on earth to have you today with us. Thank.

John MacIlwaine: Thanks a lot Really appreciate it hollander.

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