#103 20 Minute Playbook: Andrew Jamison – CEO and Co-Founder of Extend

Andrew Jamison is CEO and Co-Founder of Extend, a virtual credit card platform. In this episode, Andrew and Daniel discuss building diverse and cohesive teams and the definition of success.
Last updated
August 13, 2023
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Before founding Extend, Andrew spent 12 years as a Vice President at American Express.
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#103 20 Minute Playbook: Andrew Jamison – CEO and Co-Founder of Extend

“It's about trust in the people—because you run through walls for people, you don't run through walls for a company. And so if we create the right culture around the right people, we will continue to grow.” – Andrew Jamison 

Andrew Jamison is CEO and Co-Founder of Extend, a virtual credit card platform. Prior to founding Extend, Andrew managed all B2B payments solutions, including virtual card platforms and products at American Express. Before that, he spent 10 years as an SAP consultant.

Topics discussed with Andrew Jamison

  • 00:01:21 – Being a reluctant entrepreneur
  • 00:05:17 – Time and stress management
  • 00:07:44 – Selling into large financial institutions
  • 00:11:18 – Inspirational leaders and building great teams
  • 00:18:00 – Defining success

Andrew Jamison Resources


Daniel Scrivner (00:05):

Hello, and welcome to another episode of our 20 Minute Playbook series, where each week we sit down with an elite performer from iconic founders, to world renowned investors and bestselling authors, to dive into the ideas, frameworks and strategies that got them to the top of their field, all in less than 20 minutes. I'm Daniel Scrivner and on the show today, I sit down with Andrew Jamison, Co-founder and CEO of Extend, which is the world's first virtual card platform that works with every card issuer.

Daniel Scrivner (00:33):

Before co-founding Extend, Andrew worked as a Vice President at American Express for over 12 years. In this episode, we cover why Andrew's a reluctant entrepreneur and how growing up in a family of entrepreneurs shaped his approach to building Extend, why he goes running daily and always packs a pair of trainers in his bag when traveling, how he manages his time and approaches leading the team at Extend, and the wisdom he'd whisper in his ear if he could go back and visit himself when he was 20.

Daniel Scrivner (00:58):

You can find the notes and transcript for this episode at outlieracademy.com/103. You can find Extend on twitter @PayWithExtend and online at paywithextend.com. With that, let's dive into Andrew Jamison's playbook. Andrew, thank you so much for joining me on 20 Minute Playbook. I'm really excited to have you back on.

Andrew Jamison (01:18):

No. Absolutely looking forward to this section.

Daniel Scrivner (01:21):

So I want to start with a story that you shared with me when we were doing our first prep call around the fact that you are a reluctant entrepreneur and the fact that you spent a lot of time with a dad who was an entrepreneur growing up and how that maybe dissuaded you from doing it for a long period of time. Talk a little bit about that experience growing up and why you were a reluctant entrepreneur.

Andrew Jamison (01:45):

Yeah, so it turns out all the things I wager against end up happening to me. I waged that I would never move to the US. I'm in the US, have been for the last 16 years and I waged I would never be an entrepreneur for very different reasons, but yeah, no, look, I saw firsthand what it's like to be an entrepreneur. And this was in a different setting. It was shelving equipments. So we're in a warehouse, we're packing boxes and putting labels and counting screws, and when I tell this story, my sisters will be laughing, remembering this. And we did it with my aunt and uncle, because he created the company with his brother and I was like, that looks like an absolute nightmare.

Andrew Jamison (02:19):

When I looked across the aisle at my other uncle who was working in pharma and sort of ended up sort of working for Roche and doing really well. And I was like, I think I prefer his life, where you're sort of flying business class and doing all these different things versus... And his kids didn't seem to be counting screws and shelves and labeling boxes. But I guess, look, it's super formative. You sort of lean in and you get cracking because you realize you're not getting out of there until you get it done. So it was like, all right, let's do this, roll up your sleeves. Let's go.

Andrew Jamison (02:47):

And actually, out of it, obviously you create a really strong family spirit because the fun afterwards, like he'd take us out for dinner and we'd have a massive fun dinner and do all these different things. But again, completely different. But I was like, that doesn't seem like the journey, which is why I started my career in consulting and went to another big blue chip company called Amex. And I was like, yeah, this is more like what my uncle was doing. And lo and behold, I slipped down the slide, and went down the entrepreneurial path eventually.

Daniel Scrivner (03:11):

Yeah you did. So I want to ask one more question because obviously we just did an in depth interview, a founder spotlight episode all around the company you're building now, which is called Extend, which does virtual basically is a virtual card provider. It can layer on top of any physical card. The question that I wanted to ask you was, how did this background in being self labeled, reluctant entrepreneur shape your decision to start Extend in your perch to founding and building the company? And maybe it's nothing more than just, you said no for a long time and you finally say yes. I'm guessing there's maybe more to it.

Andrew Jamison (03:46):

No, I think it's also about, is there a good idea out there? And that to me was one of the founding things. Is there a good idea and can you get people to follow you to doing it? Because I was never going to be, I think someone who's going to go and create a company all on their own. I just thought I was just too daunting and I was really lucky in a way, on the one hand, one of my co-founders Danny, we were at a barbecue and he's like, that sounds like a great idea. And I'm like, hang on, he's fin on tech so we can do this. And then we started sort of putting our plans together and we're sort of bashing our heads in the wall, trying to figure out how we're going to present this concept as we went to money 2020 and lo and behold, Guillaume, the third Co-founder steps in to this coworking space we were operating out of.

Andrew Jamison (04:26):

And he's, former strategist and was sort like, well, let me help you guys, don't worry, let's do this. And before you know it, he's knee deep in this, even though his wife has said, "You are not allowed to become an entrepreneur." He was a sole bread in his family. It's not made for entrepreneurship at the ripe old age of 40, with three kids in private schooling. But again, just amazing in my mind what it is with three people, completely different skill sets. We're not stepping on each other's toes at all.

Andrew Jamison (04:52):

And that I found really invigorating, which was sort of like, it was so crystal clear what each and everyone had to do. And we were just a really good, solid storm. My boss always said, you need to have a solid stool, the pillars of that have to have a strong foundation and that's what we had. And then the platform became Extend and that's really what's allowed us. I think, certainly to be successful in the early days, right before we started to hire the team.

Daniel Scrivner (05:17):

Yeah. It sounds like a lot of it's maybe just having a much higher bar for when you're willing to decide to jump in and actually become an entrepreneur. I want to switch tracks and talk about focus, prioritization, time management. As a founder, there's always more to do than you have time in a day, which I'm sure you feel every day. How do you manage that? Do you have a system for it? And, can you talk, I guess, to set a super high level around how you emotionally, mentally keep yourself above the stress if that's even possible.

Andrew Jamison (05:48):

So for me, the stress part's actually strangely easy and I've always relied on it throughout my life, which is to go running. So for me, that part of me as a consultant, I always packed trainers. When I travel with Amex, I always pack trainers. When I travel today, I will always pack trainers. Because I always felt that, that was a one thing that allowed me to sort of truly release the tension. And you think about different things and running in New York's great because you see so many different things, you run down the west side of highway you're like, holy smokes and it distracts you pretty damn quickly. So it allows you to sort of to free that up.

Andrew Jamison (06:19):

I think again, going back to, I don't think me individually, I would've been a great entrepreneur. It is having a good team, like Guillaume is so incredibly organized and so driven. To break things down into individual tasks. So I knew from an operations perspective, I wouldn't have to fail there, which is what I feel I would've done. So Danny's a little bit different because, I was in product, so you would've thought, well, there's an overlap there surely. You are in product, he's in product. He just was so much more on the consumer side of product. I was a bit like, well, I can't even think that way. I'll just tell him how I think about business, but you tell me what the experience should be. So that was super easy as well.

Andrew Jamison (06:56):

So for me it was actually my primary focus really became business development and then fundraising. My job is really to engage with the card networks, engage with the card processors, engage with the issuing banks. And that's a role which I actually felt very comfortable doing, because I'd sort of done it in pre-sales with SAP and done a lot of pre-sales inside of Amex. So I was in my swim lane. So then it was all about... It's a big social aspect to it and I'm reasonably outgoing. So from that perspective, I was like okay, this is something I can do. I've never been a salesperson with a sales target, but these were really strategic sales. So it's a relationship, not a sale. So that bit I felt very good with. I feel that's one thing I've enjoyed doing is building relationships. So that felt good.

Daniel Scrivner (07:44):

Yeah. Talk a little bit more about that because one of the unique things that we didn't touch on in the previous interview was around just the unique nature of selling into large financial institutions. And you've spent a lot of time doing that as you said, not with a particular or exact sales label, but what's unique about that, and what are some of the skills that are important in doing that? And maybe just talk a little bit about the speed, the pace.

Andrew Jamison (08:08):

Yeah. So I think one of the things that you have to recognize is, big financial institutions have a short and list of goals that they can go and pursue in any given year. So number one is like, okay, how do I ladder up to one of those? Because I'm not going to create a new item on the list, that's for next year, that's an 18 month project. So how do you create something that's already on the list and repurpose what you're doing into one of those items? And then the other things we learned very quickly was, you better make damn sure that your tech is plug and play. If a financial institution, your card network or process has to do any tech work, you can guarantee you're not 18 months down the line, you have three years down the line, because they have lists, longer than both their arms of things they need to get done.

Andrew Jamison (08:48):

So it's like you got to find a way of being plug and play. And then the second piece was, get over the second hurdle, which is a contractual piece, which can take two years. I sort of talked about in the earlier episode, how do you shrink that down to a couple of months so that you take away that fear factor in that piece? And I think the last piece is, we've hit the market at the right time. Timing is everything with these companies. When I first started talking about virtual cars back in 2008 and nine, you'd find at a conference, maybe one little side room where people are talking about it. I just came out from this conference in London. I think there wasn't a single session where virtual cars didn't come up as a topic, because this concept of digital issuance is at the heart of everything today.

Andrew Jamison (09:27):

And people are thinking about from the application process to receiving your actual funding account and then creating all these digital account, it's all one digital path. So we're at the kernel of what that is, how do you create from that one account, thousands of potential other accounts that flow off it. So you got to be at the right time, right place. There's an element of luck in there and then judgment as to when you want to go and create that business, and all these things have got to come together. There's no one success factor there, but certainly engaging with the banks and knowing what their priorities was. I think probably the biggest scary part was, what we'd initially thought this is really going to help with contractors and employees didn't have cars and then COVID hit, and you still sit there going, "Well, all the contractors got fired really quickly." No one's traveling. And you're sort like, "Well, what the hell do we do now with this business?"

Andrew Jamison (10:18):

And that's just again, where you start to very quickly understand what are the next set of problems that occurred, and what happened is the whole workforce got distributed instantly. So you had an even greater need as it turns out, not for travel, but for things like subscriptions and for paying suppliers and for people embedding payments into other services that they were offering and the way they could do it centrally in the office. Now they can't. So you have to reinvent yourself in the moment.

Andrew Jamison (10:47):

And funny enough, we unearth the much bigger opportunity than what the first one was. Tail spend has been a nightmare. But for decades, in fact, that was my first project with SAP was, help us understand how we can better manage one time vendors in SAP. And now here I am, 30 odd years later, like yeah, it's still pretty bad. So virtual cards are a great tool to help in that journey. So it's almost full circle. First project, first startup, we're back to solving for these one time suppliers or suppliers where you contract, fairly and frequently with them.

Daniel Scrivner (11:18):

Yeah. Like a lot in life, just complete full circle, complete round trip. As a reluctant founder, so you then start with two wonderful partners Extend with two co-founders. Were there any books that were instrumental for you guys? And this could be you individually, just anything that had principles that really spoke to you that you put to use building Extend, anything that you shared or asked employees in the company to read, anything that you and your co-founders read. Is there anything in that regard?

Andrew Jamison (11:48):

So I can hear my wife figuratively laughing over my shoulder saying, "What are you talking about, Andrew, doesn't read." I read the FT a lot, but I do also listen a lot and I take a lot out of the different leadership courses that I've had over my time. And yeah, I also read sort of white papers or Harvard Business Reviews or those kind of things which are little sort of sound bites where I can actually walk away and remember the challenge when you read a book is by the end of it, you're like, hang on, what were the three really interesting lessons that were supposed to get out of it? So I'm much more into reading little soundbites of things that I can absorb very quickly and churn out the other side really quickly. I have a stack of books that I'd be meaning to read. I read a few books between Amex and starting the company. And there are a few, and unfortunately off the top of my head, I can't remember. There's a couple that I really liked and I've completely escaped me.

Daniel Scrivner (12:43):

If you think of them, email me and I will add them to the show notes.

Andrew Jamison (12:46):

Brilliant. There you go. Because no, look, I think that's the thing, you need time. And for me, relaxing is mostly been going for runs or spending time with a family or watching a Netflix series. That's what I do. I sort of, I need to decompress with different sensors.

Daniel Scrivner (13:05):

Yeah. No, I think that's really well said, and I love the way you describe white papers as tiny, actionable something you can churn and immediately put to use, because I relate with that a lot. And I think which is why I way too and frequently read fiction books, because I'm just like, what's the point. Even if I'm enjoying the story.

Andrew Jamison (13:24):

I'd love to say much more intelligent by claiming that I'm really into reading like some philosophical books. It just, at the end of the day-

Daniel Scrivner (13:31):

Just Financial Times. Just financial times and maybe a couple Harvard Business Reviews and you're good to go. Are there any thinkers or founders or executives that you draw on for inspiration or that you draw on for inspiration building Extend?

Andrew Jamison (13:45):

Again, I take it from a lot of my own experience firsthand. I'd like to some extent you look at some of these founders, and then you discover many years later that not really who you thought they were. So I've tended to rely more and more on my own life experience. And I was actually meeting with one of these individuals who's a mentor of mine, who helped set up this company where we were working alongside SAP called Druid back in the day, a gentleman by the name of Nick Keating. And again, for me, that the key part is he was all about creating these high performing teams. And really it was all about, if you're stuck in an airport with someone for six hours, are you going to survive? And if you are, then you've probably found someone who's really good.

Andrew Jamison (14:25):

I'm going to assume you're smart enough because you went to a good school and all those things, he was much more focused on actually, are you going to be cohesive as individuals? So for me, that was really instrumental as I thought about teams, I took a huge learning from him and he made work fun. We all knew at the time we were working 14 to 16 hour days and you knew you had to have a fun decompression piece. And he had a flare for the amusing as we went out after work and even during work. He had a very good sense. And then from a people perspective and this wouldn't be a surprise, I think to anybody who's certainly worked at American Express.

Andrew Jamison (15:01):

Ken Chenault was truly an inspirational leader on so many different levels. He did so many things that frankly companies only just catching up to today, which is, what's the percentage of leaders that are women on your team? How much diversity do you have on your team?. And it was linked to our financial goals. 25% of our bonus was linked to, did you meet those criteria?

Daniel Scrivner (15:22):

That's serious skin in the game, which obviously improves the odds it's going to happen.

Andrew Jamison (15:26):

That's right. And his view was unless we put in some of this positive affirmation pieces, we are going to sit there and not do anything about it. So it has continued right inside of the company with Steve Squeri now. And I think it's ingrained in the leadership, that it's upon us to act, to create a more equitable place at work. So that becomes an important part of it and actually it's funny, we had International Women's Day, and I think we've quickly realized that 40% of the employees, 42% I think were women, our Chief Product Officer is Orna Albus, our chief people officer is someone who used to work with my wife at the Brooklyn Nets.

Andrew Jamison (16:05):

So again, we've brought people into leadership and again, I'm constantly asking people to hold us accountable, not just for who we employ, the type of business that we do as well. Are there any business construct that people aren't comfortable with? And again, I've found that the team has a really strong voice and I think that's because we've layered that trust in there and we're all trying to do the right thing. But that's where I've taken my inspiration from, probably more so than sure, you could sort of lean in and say Warren Buffet and it's amazing, the [inaudible 00:16:33] works like he's 90 or work he's 130, if he lives that long on the other hand you could say Bill Gates and you could say all these different people, but the reality is I feel it's more powerful because it's people I've worked with and I truly understand what those values really are. So I can more easily embody them and really impart them onto others versus people who again, invariably over time will somehow disappoint us.

Daniel Scrivner (16:59):

Yeah. But you think you know at a distance it's much different when you work with someone like in that example, 14 to 16 hour days. If you work with a leader who's inspirational and you work together that much time, that is truly extraordinary. It's truly extraordinary person. I think there's a lot to learn there.

Andrew Jamison (17:16):

But I think reminding people, and that's one of the things which is interesting in US, people take themselves quite seriously as a general rule. One of the skills that Brits have is to be very self deprecating, and then sometimes that doesn't gel, because people are like, "Are you serious?" You're not serious." And I'm a bit like, no, the whole point is guys is we should be able to have fun, make fun of ourselves first, which then gives us the ability to lean in and create a bit of a comic moment across the board. So that's one of those things which you want to impart on people is, we work really hard, but we got to have fun at the same time. I mean, that's just the reality.

Daniel Scrivner (17:51):

Yeah. We're only here for as many years as we're here. So let's not make them duller than they need to be.

Andrew Jamison (17:57):

That's exactly right.

Daniel Scrivner (18:00):

I want to ask a question around success and you're someone who seems very principled in the way that you think, and the typical way I would ask this question is much more personally like, how do you define success today? How has that definition changed over time? I'd be curious to hear your answer around Extend and what success looks like for Extend. I'm guessing that will change over time, but what are your thoughts building a company that you've obviously invested enormous amount of your own life, your founders as well, your team as well into. What does success look like and how do you think about that and talk about that as a company?

Andrew Jamison (18:34):

So for me, success, I really define it as standing a company up that stands in its own two feet. That's not reliant on venture funding. That's not reliant on external forces and factors. It's can you truly build a standalone business in collaboration with partners. That to me is number one, is that I define that as a huge success for the company as a whole. Then I think that the success goes back to again, the type of team and culture that you go and create inside of the company. And again, we're only on this earth for as long as we are. So I'm keen to create the right culture, the right level of serious and comic mixes that come into there. But also, for me, success is really about how you're willing to take risks on people, how you're willing to empower people.

Andrew Jamison (19:23):

Because I feel that in a lot of bigger companies, you run through a process, it's almost like, you've been here two years, you should be this. You've been here for four years, you should be that right. And some people don't quite make it because they don't have the social piece or they don't have this and that. So it's quite liberating to be able to create a culture here where we get to choose how we want to play that game. And hopefully we write size things relative to what a small company looks like but ultimately, like all of these companies it's about the people. So if your success ain't about the people that are the motive behind the engine, that might be the voice piece, that's out there.

Andrew Jamison (19:56):

But ultimately I think I'm judged on success is how does the team feel about the business? How does the team feel about the direction we're going in and therefore attrition and all those things to me, matter a lot, because it really starts to sort of talk very openly as the type of culture you've created as a company and clearly for me, that's the important part, because again, I think as you get older, financial matters matter less and less. I think that's just the, I don't know, that's been my experiences. I've spoken to a lot of my friends recently is, you're much more focused on your family. You're much more focused on making sure that those pieces of the pie and you're not chasing, keeping up with the Joneses or did you buy this or did you buy not, you're much less focused on consumerism?

Andrew Jamison (20:43):

So for me, that's the piece that gets me more and more excited. Don't get me wrong, I have financial needs. I want to make sure my kids are well taken care of, but the end game for me is not any sort of massive financial outcome in this, it's about creating a company that creates the right level of returns and empowers people to go on to do great things.

Daniel Scrivner (21:01):

Feels like a lot of it's around what's truly durable as opposed to what... I think with money, you can come up with a nice bank account, but I don't think at a certain point just working towards more and more makes no sense. And I think it sounds what you're focused on your team is much more of the durable things that are truly built to last, which is, do we enjoy working together? Are we having an impact on the world?

Andrew Jamison (21:26):

Well, I think the thing is I also have my career in my own hands. That's another big important thing. I reached 50, so in larger companies, you start to feel like maybe you won't get to control your destiny. So I feel as there's an element there that's quite satisfying too, is like, hopefully you get to a place where you get to choose the path and direction you want to take and where you get to step off the gas and do all these different things. So there's definitely a selfish bit in there as well.

Daniel Scrivner (21:52):

No, but it's a selfish bit, but I think to say it another way, it's like, you're finally handed the pin to your story and it's like, here you go, your turn. Your turn to figure out what to write and what to write next.

Andrew Jamison (22:02):

Yeah. No, that's very true.

Daniel Scrivner (22:05):

Thank you so much for joining me on 20 Minute Playbook. It's been a joy to have you on Andrew. I really appreciate it.

Andrew Jamison (22:09):

No. Cheers Daniel.

Daniel Scrivner (22:12):

Thank you so much for listening. You can find links to everything we discussed as well as the notes and transcript for this episode at outlieracademy.com/103. For more from Andrew, listen to episode 100 where he joins me on our founder spotlight series to go deep on Extend, the world's first virtual card platform that works with every single card issuer. In that episode, we explore why tokenizing a physical card into many different virtual cards for specific people on your team or departments at your company unlocks a lot, including a much better understanding of who spent what, which makes accounting and running a business so much easier.

Daniel Scrivner (22:48):

You now also find us on YouTube at youtube.com/outlieracademy. On our channel, you'll find all of our full length interviews, including the video version, as well as our favorite short clips from every episode, including this one. Thank you so much for listening. We'll see right here next week on Outlier Academy.

On Outlier Academy, Daniel Scrivner explores the tactics, routines, and habits of world-class performers working at the edge—in business, investing, entertainment, and more. In each episode, he decodes what they've mastered and what they've learned along the way. Start learning from the world’s best today. 

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Daniel Scrivner and Mighty Publishing LLC own the copyright in and to all content in and transcripts of the Outlier Academy podcast, with all rights reserved, including Daniel’s right of publicity.

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