Defying the Corporate Comfort Zone: Andrew Jamison of Extend

Summary of Episode

#64: In this episode of the podcast, we speak with Andrew Jamison, co-founder of Extend, a platform that enables businesses to issue and manage digital credit cards. Jamison shares his journey from leaving the corporate world of American Express to embarking on entrepreneurship. Jamison explains that the idea for Extend came from identifying a gap in the market for a solution that would capture spend, reconciliation, and expense management, particularly for the middle market. Jamison also touches on the challenges of starting a company, including the need to secure investments from friends and family before reaching out to professional investors. 

About the Guest: 

Andrew Jamison is the CEO and Co-Founder of Extend, an innovative fintech startup that makes managing money simpler for startups. Before starting his own fintech startup, Andrew worked for over a decade as Vice President and Director in various departments at American Express.

Podcast Episode Notes

Introductions [0:00]

[1:35] Who is Gloria the chicken?

[4:23] What is Extend?

[8:15] What's the difference between a company that's sitting directly inside of it versus companies that are trying to solve this problem from outside?

[11:29] The Extend solution for the middle-market. 

[18:10] Andrew discusses not wanting to become an entrepreneur due to familial ties. 

[23:34] Andrew details leaving his cushy corporate job after realizing passion for solving complex problems, founding business with co-founders who each bring unique skills.

[31:22] Starting a startup requires personal sacrifice and milestones are important for success.

[37:58] Amex emphasizes service, builds strong teams, but lags in technological innovation. 

[42:12] Why having 3 co-founders provides diverse perspectives and expertise, preventing absolute power and allowing for mistakes. 

[45:48] Building infrastructure for digital distribution and integrating with the banking system, starting with commercial credit cards, to reduce friction for businesses and individuals.

[48:25] Andrew’s #1 piece of advice for entrepreneurs? Entrepreneurship is humbling but fulfilling. 

Full Interview Transcript

Ethan Peyton: Hey everybody and welcome to the Startup Savant podcast. I'm your host, Ethan, and this show is about the stories, challenges and triumphs of fast scaling startups and the founders who run them. 

Our guest on the show today is Andrew Jamison. Andrew is the CEO and founder of Extend, a company whose goal is to make business spend management simple. Andrew's career trajectory is a little bit different than many of the guests we've had on the show. He spent more than a decade in the corporate world at American Express, where he held several high level roles. And we're going to explore this transition out of corporate and into entrepreneurship quite a bit, because I think it's really important to explore the multitude of ways that people can find themselves in entrepreneurship. 

But before we get into that conversation, I wanna ask something of you. We want this show to grow and we want more people just like you to learn about startups and entrepreneurship. And the simplest way to make that happen is for you to share this show with your friends. So if you like what you're hearing, tap on that share button and fire it over to that other business nerd friend of yours. And I think both of you will learn something from hearing Andrew's story. But hey, speaking of Andrew's story, I'm gonna let him tell it. Hey, Andrew, how's your day going so far?

Andrew Jamison: Hi, Ethan. Going great, going better still now that we're on this show together.

Ethan Peyton: All right, I love to hear that. And we're gonna start out with a real curveball, just coming right out of left field, and I guess that's not where curve balls come from. So I'm gonna end the baseball talk right now. Andrew, tell us who is Gloria?

Andrew Jamison: Well, starting with curveballs, by the way, as a Brit, I'm more focused on cricket. Then curveballs, I was confused right there. Gloria is a very important part of our team. I think she, more than anything, encapsulates really the ethos of Extend. She is a chicken and somewhat poking fun at ourselves as a startup because so many people, when they... put the list of employees, put their dogs, their house pets, and I was like, okay, it's a little bit silly. So I always liked to go one step sillier. And we had a pet rooster, pet chicken. And that's because one of our earliest employees lived in a farm down in the Carolinas and she had 10 of them running around. And Gloria became really for us. by the symbol of really what we're doing here. We're doing something a little bit unusual and we're gonna continue to buck trends in terms of how we try and do things. And that's pretty much what the whole business model of Extend looks like and we'll get into that in just a second, but you'll start to understand a little bit more why, why that makes sense.

Ethan Peyton: Yeah, you know, the first time I saw Gloria was on the kind of like about us page where you were listing the, you know, associates and the names and all that good stuff. And I'm like, hmm, I'm not 100 percent for sure. Somebody might have laid an Easter egg on this website for, you know, someone like me who's doing research to come find. And then I saw it referenced again somewhere else. And I think it was your 2022 in review. There was a little chicken character. And I'm like, this is not a mistake. I have to ask about this. So thank you for letting us know about Gloria. And one step sillier, has that ever gotten you into trouble?

Andrew Jamison: The chicken or just trying to be contrarian?

Ethan Peyton: Just what the ethos of one step sillier.

Andrew Jamison: I think it always gets you in trouble, but there's levels of trouble, right? Trouble which stirs a good conversation, and there's trouble you don't want to be in, and I'd like to say it's in the first camp. But I think in general, it's healthy to poke fun at yourself. I think it's certainly one of the big character traits of Brits in general, and even though I'm only partly British, it's something I learned in boarding school pretty quickly. And it's served me really well ever since, right? Don't take yourself too seriously because frankly nothing good really comes of that. And I think if you can poke fun at yourselves means that you're open and receptive to feedback and then all good things start to go from there.

Ethan Peyton: You know, I think that's really good advice and we're gonna just end this on a strong note. Andrew, it's been really good talking to you. No, I'm kidding. So let's get into Extend, let's get into the business. Can you tell us what is Extend?

Andrew Jamison: Yeah, absolutely. So look, Extend at its simplest form, right, is trying to turn, every day commercial credit cards, right? And I say commercial because we're in the B2B space, not in the consumer space yet, into really a spend management vehicle. What does that mean? Right? Simply put, we're just trying to superpower the existing card that people have in their wallets, enabling people to have more control over how it's used. how potentially it can be distributed from that very physical card. And what I mean by that is have a very simple way through which I can take my card and shard off a piece of credit and give it to you with controls over where you can spend and over what period of time you can go and spend and up to what amount. And yet keep it all streamlined to my one credit card without having to sort of go through this whole issuance process for you to have a card, et cetera, et cetera. And then it's, you know, obviously it extends from there, no pun intended, but it's really then going into the broader expense management capabilities of visibility, and making sure that from an end of the month perspective, you help CFOs close their books as quickly as possible with as much control as possible.

Ethan Peyton: You know, this isn't the first business that we've had on that is kind of tackling this employee spend issue. Is it, I mean, are the solutions that are kind of like the legacy solutions that are out there right now, are they just really, really not good? Or are we coming into some sort of evolution of how things are being done inside businesses that is opening up new problems to be solved in different ways?

Andrew Jamison: Look, I think it's definitely an evolution. I think there's been best of breed solutions out there in the past, but technology is really what's enabling all of this, right? We've moved away from EDI into APIs, and that really is sort of enabling things at the transaction level rather than the batch level. And I think as a result of that, right, you start to have much more interactive solutions. 

I think the other frame I would put around this is... We focus a lot on technology, I think, on sort of B2C or in that pure consumer side of the world. I think a lot of these solutions we're talking about here are B2B and those are inherently much hairier problems to solve because suddenly you have company policies, you have technology that gets inserted into the discussion and into the process that you don't get to choose as a consumer, you are told to use. And so it brings a degree of complexity that frankly hasn't been tackled that well over the last 30 plus years. And the reason why I can say that with absolute confidence is, you know, I graduated from, from college in the mid nineties and the first role I did was go and join an SAP consultancy, right? So big hairy projects, right? Enterprise resource planning in its earlier days. 

And for me, the first project that was really tasked on was like, help us manage in the finance module, specifically, tail spend, right? These ad hoc suppliers. And it's just, tailspin goes way beyond just employee spend. It's really some of the other ancillary spend that doesn't go into your overall cost of building things. And that's usually about 20% of the spend. And it wasn't solved back then. And what COVID showed us was it's sure as hell ain't solved today either. Because suddenly people were stuck at home and they had to go and pay vendors. And suddenly I couldn't get access to the check printer. And so all of this came bubbling to the surface. And I think what you've seen is a proliferation of companies that are looking to solve for these challenges. Some are doing it outside the established financial services mandate, and we're very much inside the financial services ecosystem.

Ethan Peyton: What's the difference there? What's the difference between a company that's sitting directly inside of it versus companies that are trying to solve this problem from outside?

Andrew Jamison: Yeah. So, you know, if I look at how we're skinning this cat, not that I like skinning cats, but if I like to see, and again, a lot of this is driven from my experience with SAP. Right. I, my general belief is specifically in companies, they've got to invest in software already. Right. And they've already typically have a credit card that does a lot of things that they want. And for me, it's about threading that fine, you know, the thread through that, through the holes of the different technology platforms that they already have and essentially allowing them to do more with what they already have. Because having to strip everything out and start all over again is really painful for companies. 

And it's almost like, I'm just asking for incremental change, not for an overhaul. And the overhaul sometimes is a little bit overwhelming. And so that's the difference in my mind, right? And really what you see there is some of these players have come in and said like, you know, we're gonna rip everything out and we're gonna start from scratch. And that gives them tremendous freedom. But it means they have to go through a whole customer acquisition channel, which is super expensive and gets more expensive in a world where financing costs more than zero, which is the world we're living in now.

Ethan Peyton: That sure is true.

Andrew Jamison: And our philosophy has been, no, we'll essentially make best use of the tools, of the credit cards that you already have, and we will layer that digital experience and digital capabilities over the top of it. And again, I learned that in the world of SAP, where if you think that this turn of the century, I really feel old when I say that, but if you think about it then, right, SAP kind of won the ERP battle largely because they decided to become the ledger of choice across lots of different modules, whether it's sales or whether it was the general ledger, but then they kind of opened up this whole EDI channel and essentially then they allowed software providers to build over the top of them. And that's how Concur came to be and Ariba came to really be. And they bought both because they were best in breed serving Fortune 500. And I believe the same is happening in financial services today. What has been a closed ecosystem is now opening up, right? Largely because regulations have stepped in and said it's client financial data. And so you need to be able to give access to people.

Ethan Peyton: Gotcha, so just a bit of a personal background. Before I started my business and before I came in and worked for TRUiC, which is this company, I worked for a company that used SAP for everything. And so every time you say SAP, I kinda just like wanna crawl inside of myself and go find a little hole that I can just live in for the rest of the day. So good on you for having more boldness than I do. But so your platform, your product, is this a, obviously you're taking the existing credit cards and you're kind of giving the ability to split that credit card to multiple different, to different people within an organization. But what's the like form factor? Is this a piece of software that these companies are interfacing with or what's the actual product gets when they sign up for Extend. 

Andrew Jamison: Great, great question. So really all it takes is a piece of plastic, right? So you have an account. And again, here was a really first to market. They've said, actually, let's start with a simple form that everyone has in their possession. Don't go sign up for anything new, right? Don't go sign a new contract. Imagine, it's hard enough to try and open a new relationship when you're a consumer. It gets exponentially harder when you're a business. And so our view was, let's start with what they have. And then all you really, we're asking people to do is to have either a web application or a mobile application and register that card like you would in PayPal or anywhere else. And through registering through that experience, that is an extended experience, right? We essentially are able to authenticate that you're the rightful owner of that card. And from that point onwards, in under five minutes, I now have given you the capacity to distribute digital credit cards to thousands of people. Right? And that's really the key to this is, Why do incremental vetting? Cause you already have a line of credit. You've already established a relationship there. And really all we've done, all we've done, we've got to build right a platform and then some digital experience over the top of it that allows for that user experience that strays away from what you talked about, which is that SAP thing that makes you crawl into a box.

Ethan Peyton: Mm-hmm.

Andrew Jamison: Because unfortunately, when you build these monumental-like systems, by definition, they're fairly generic. And so you have to be an expert user to really see the value behind them.

Ethan Peyton: Yes.

Andrew Jamison: But if you're using it in your very sort of narrow industry or whatever it is, corridor, right, the terminology doesn't feel right, right? And so really what we're doing here is putting an experience that's right sized, right, for the types of businesses and for the types of people who just want a simple experience through which they can do all of these things. And unfortunately, the world that we live in is… we have a lot of sophistication in consumer. 

We have some sophistication in enterprise. But like children, the middle child kind of got starved and they're stuck between the two. And that's where we're bridging the gap, right? In terms of the segment we start to be really relevant to is kind of that business of a hundred, 200 employees. They're not enterprise, they're not consumer, but please give me the digital tools to help me run my business more efficiently.

Ethan Peyton: And did you choose that market simply just because there weren't great tools for those users already built?

Andrew Jamison: Yeah, so two reasons. One, I feel that on the enterprise level, I already knew that companies at that scale have curated experiences already. And actually, they don't want a net new user experience. They just want you to be embedded into that one, right? Because the change management needed to deploy things into large scale companies is huge. And so that's typically something that takes too long for these companies to approve. So I wasn't interested in going down that path. And I think there are plenty of sophisticated solutions out there. 

Then on the small business front, it was just these consumer plays that had been adapted a little bit to business, but they sort of like, they did it in a way that you sort of realized this is a complete afterthought, right? And there wasn't really the thought of a CFO over the top of this. It was almost like, no, you're really just a consumer with maybe some children, right? And so those children are now employees as opposed to your children. And I think that's the bit where I was saying, okay, there has to be a better middle ground and it's not like I blazed the trail here that there's others who got there ahead of us, but they chose to tear down Rome rather than to sort of interact with Rome. And so different approaches. And I just believe long term, the better approach is to mix old and new like Rome is today to actually create the right experience for these and reduce actually the amount of friction that's needed for these customers to adopt these solutions.

Ethan Peyton: Yeah, reducing friction seems to be a very common thread in the businesses and the founders that we interview. And we hear more and more about APIs, which is also something that you've mentioned, replacing things like fax machines and letters and phone calls and that sort of thing. And so it's very cool to see yet another application where technology and new thinking are creating businesses that essentially these businesses aren't completely unsolved but you're taking something that is difficult to solve and making it simple. So I really like seeing that. That's pretty cool.

Andrew Jamison: Yeah, look, I think the, I think what's interesting, right, and I think it's not just in this particular segment where we've seen a trailblaze, right, it goes back a couple of decades, right, and it all started really with that B2B2C world. It all really started with this whole concept of embedded finance, right, and obviously, the early adopters in that space were the likes of Uber. The more recent adopters, right, with the sort of buy now, pay later players. 

But in each and every one of those instances, they were really trailblazing in terms of trying to offer new financial solutions to consumers. I think the world that we're living in here is, “that's all we're willing to get. Good, go trailblaze, but hey, there's context.” You need to be aware of the context of businesses in order to really make this work in scale. And really, I don't think we've even seen the beginning of scale in that B2B space, in the commercial space, because we're only really talking about embedded finance 2.0 in my mind now, which is, hey, how do you make all of these ecosystems talk to each other through APIs? But how do you build really that middleware layer in between, right, that allows for it to translate between the two ecosystems without everyone having to reinvent the wheel every time? And that hasn't been possible in the credit card world because there's never actually been a standard, right? 

So there's, weirdly enough, there's a standard for ACH, it's called Narcha, there's one for international called Swift. There are standards around how you print checks. Credit cards, every issuer did it differently. And so if you're a technology company, you're like, well, I don't know how to get after this because I don't wanna have to reinvent 72 different ways of doing the same thing. and manage these idiosyncrasies and manage uptime of these platforms. I need a third party to do this on our behalf. And that's really where we're stepping in.

Ethan Peyton: All right, so I want to talk about your history a little bit. And before you became an entrepreneur, and this is your first startup, your first founder role, is that correct? 

Andrew Jamison: That is right, yeah.

Ethan Peyton: All right, so before you became an entrepreneur or founder, you spent most of your career in the corporate world. Can you tell us a little bit about that part of your career?

Andrew Jamison: Yeah, so I think the most important part is I started my career not ever wanting to be an entrepreneur. And the simple reason for that is my father was an entrepreneur in a totally different space. He was an entrepreneur in shop fitting equipment. We're talking about big French hypermarkets and really how you think about, you know, how you display products, et cetera, et cetera, et cetera. And I did my usual kids do the summer internship, right? The grinder, the grinder project with your dad and you're like, “oh, this is really never gonna go very well.” And I learned an awful lot. The first thing I learned was like, oh, I don't wanna do this for sure. Cause I had my uncle who was in pharmaceuticals and things seemed to be much rosier and much more interesting down that path. 

So I was committed to never becoming an entrepreneur. And then you look back and say, never say never cause it will bite you. But going back to your original point, look, I left. college and I had a choice to make in terms of going to a big three strategic consultancy firm or joining a very early stage emergent SAP consultancy. I was employee number 52. So to some degree it was a startup but I always look at people-businesses a little bit differently right as a consultancy firm and we grew really fast right. We grew from 52 to 700 employees in five years completely organically because SAP just took off right as a… and just continued to grow from there. 

And for me, what happened there is being in a smaller company versus the likes of Arthur Anderson's back then, Accenture Today, right, is we got exposed to much bigger deals and really exposed to bigger functions. And I really enjoyed that journey. But then very quickly I realized that, you know, you go from project to project to project, it's a pretty flat structure, you never really own anything, you're really helping and advising. And that's when I decided to... to make that change and say, hey, I've learned some great skills of how to manage big projects. Now let's go and own something for real. 

And that's when I went to business school and used the business school as my transition point after NCI to go and join American Express in London. And for me, the journey there was pretty simple. American Express was going through this transformation, or certainly... certainly a desire to expand beyond the borders of T&E, just not just about travel and expenses in the commercial world, but hey, how do we tackle tail spend? How do they continue to grow into other spend areas? And so for me, it was a pretty easy one because I was one of the few people that sat on the other side of the fence trying to implement these solutions for big corporate clients. And so I had a pretty good idea of what it took to make a payment happen, right? In terms of having supported. You know, AP clerks, accounts receivable clerks, you know, folks in charge of general ledger, the VPs of finance and CFOs, et cetera, et cetera. 

So that's what got me into that particular world. And then I sort of developed a real fascination really with payments. And how do we go beyond traditional just plastic cards into that more digital ecosystem? And that's kind of a big piece of the business that I was lucky enough to build up. We made an acquisition of a company and in fact we made two acquisitions. And I was the lucky person that got to go and define the product strategy around those two platforms and had to some extent the luxury of growing it from close to zero to about 35 billion over…

Ethan Peyton: Wow.

Andrew Jamison: …the five years in terms of payment flows. But that's a pretty material number when you start thinking about scale. And that's really what I enjoyed. I don't know if you have a specific angle on that question, but I can certainly talk a lot about my corporate experience and how I see some of the differences there.

Ethan Peyton: Well, let's definitely talk about the transition from corporate to startup. And I find it actually really interesting that you specifically didn't want to be an entrepreneur. And yet here you are as an entrepreneur, you know, you've been running Extend for what did you say, five or six years?

Andrew Jamison: Six years, yeah.

Ethan Peyton: Six years. So, yeah, you've taken the thing that you didn't want to do and you're kind of extending it out into a, you know, into a new career for yourself. But I think that feeling of, “I have a job. I am an employee, but I want to start something of my own. I want, I'm dreaming of something bigger for myself,” or even folks out there that just kind of want to have autonomy over their own time. Maybe they're not looking to build a business that's gonna be worth a billion dollars or whatever. They just want to have something that's building a lifestyle for themselves. But so many of the world aren't entrepreneurs. They are employees. And so that's what I want to, I want to really hit on, you know, how this transition happened, how it worked, how it may have gone better, you know, that sort of thing. So I think the first question that makes the most sense is what made you want to give up that, you know, essentially cushy corporate job? And you may disagree with me on how cushy it was, I have no idea, but what was the? Was there some sort of catalyst that kind of like solidified your decision to go in the entrepreneurship direction?

Andrew Jamison: Yeah, it was a bit of a life changing one for me personally. But I think, you know, you go back, you talk about the cushy job. Look, I think a lot of corporate jobs are pretty easy in that there's no stress because some bigger company is like paying your salary and if you're decently competent, right, you're going nowhere. And so, yeah, it's really the bigger the company, right, the more you have to be flexible and adapt to politics, because the politics is part of the game. And if you're not happy to play the game, then you're in the wrong type of environment. And it took me leaving to really understand, right? It's a game, right? In many cases. And you have to be comfortable navigating. 

You have to be very comfortable compromising. And I think to some extent, in many cases, you move from department to department, so it's hard to have a real passion for one particular thing. I think in my case, I had no desire to go into consumer inside of American Express, because I was like, if it's this blue, that blue, or the other blue, I was like, I really don't care. And I'm not driven by the color of my card. And so I was like, I'm just not a good candidate for some of those pieces, because I could never get behind it. But I was really always passionate about B2B payment flows, right? And... you know, how you go from a purchase order to a receipt to then, you know, a payment and the reconciliation, just the complexity behind it had my mind spinning and wanting to learn more and to dive in more. Now why leave that environment? Right. It's really comfortable. 

And really for me, it boiled down to one simple thing. Unfortunately, my mother was very, very sick at the time. It wasn't new. My mother had had her first bout of cancer when I was 10 years old. And. bless her soul, right, she battled through for 35 years with five different bouts of cancer, survived probably 12 years more than she ever should have done through sheer willpower and courage. But what it really helped me understand when I took a sabbatical, so I left Amex to go on a year long sabbatical and I decided to leave because I wanted the freedom to spend the time. and really enjoy the time versus always having this thing in the back of my head, like, you gotta get back, you gotta think about X, you gotta think about Y. And what that ended up creating is a bit of a luxury, which is time, right? 

In today's world, we rarely give ourselves time. And time is such a positive thing. It's why kids are so creative, is they have time. And we deny ourselves time as we get older. We fill it with lots of things, and we sort of never stop to think. And so this enforced time, because my mother at one stage was a little bit bedridden, so you're sitting there and you're thinking, and you really start to have the ability to process thoughts and those thoughts become clearer and clearer the more time you spend, right? Really sort of hitting on them. And what I learned about myself during that period was I love building things. I love talking to customers. I love getting into the depths of problems. But what I realized was as I got more and more senior within Amex, I got further and further away from what I actually love doing. And that's the piece where I realized I don't want to compromise on that anymore. 

Because whether it's Amex or another big blue chip company, I was still gonna be involved in more of the politics and the paper shuffling and all those pieces, which again, it wasn't really where I saw myself. And you can say, well, clearly you're not a good general manager. I was like, no, what my passion was, was actually to get out there and solve hairy problems, building things and solving, and solving for those challenges. 

So that's where I sort of gone from that. Never, ever did I suddenly have this moment of like, yeah, but if you're going to fulfill what is important to, to, to you as an individual, then you need to get back to building. And then it was all about, okay, but do you even have a good idea? You know, here we were 12 months after I'd left 14 months after I'd left Amex and I started sort of pushing around different ideas, but most important, I started looking into the marketplace of what had happened. What was transpiring and what you saw. Well, companies like Brex coming up, you saw companies like Marqeta coming up and the relevance of that is Marqeta on this idea of like these new businesses that are doing BNPL or they're doing right food deliveries.

They essentially needed access to APIs. Right. And they needed something they could set up quickly. And so there was a whole ecosystem that was being built around that. So that's interesting, right? Banks inherently typically, if you wanted to get access to these complicated technologies, took months, not hours. And I was like, okay, so they've hit on something there. 

Then the second part was, okay, this old middle child, right, middle market, middle child, the heartbeat of really the American economy, right? Had clearly articulated that they needed different solutions because you started seeing the Brex’s come along, the Divvy’s come along, and since then, there's been a plethora of these players come along. And I realized there was clearly a gap in the market for a solution that sort of captured your spend and reconciliation and expense management and how you managed your employees and their capacity to spend. And so those two things for me with the catalyst saying, okay, so I wanna build, right? There is a real opportunity there. And then I said, well, I could try and go and do it inside of a company, but I kind of half was in that environment and realized, it's hard to get that amount of discretionary funding. It's hard to get longevity of focus because leadership changes every 18 months. 

And I decided actually then the only way to really do this if I was gonna do it was to go out and step out and become an entrepreneur. But there was still one thing that held me back. which is like, okay, I can talk thin and I can talk some tech because of my SCV background, but I didn't feel comfortable enough that I could stand behind that piece. And so the final piece there was that Danny, who is one of my two co-founders, was actually a very good friend of my wife's. We talked a little bit about credit cards and we talked about this problem and he'd been thinking, you know, he'd been doing staff augmentation and really thinking about high-end consumer brands, right, with the likes of... projects for Apple and Tiffany's and others. And he was really a designer and an iOS developer. And he said, I love the idea. I think we should go and do this. 

And so that pushed us really to the edge of the precipice. And when we finally fell over is when Guillaume, the third co-founder who had a long time in sort of strategy at Amex. And I got to know him when he owned data products and said, hey, I love this journey. I wanna be part of this. And I'm actually looking for my next opportunity. And so suddenly we had a very steady three-legged stool where we had three people, you know, mature, I think, in our approach because we've all got gray hairs. And really said, okay, we don't have any overlapping skills. I think we can actually make this happen.

Ethan Peyton: So you've got three gray-haired guys with lots of experience. I'm assuming that between the three of you, there's probably a lot of financial security for personal, you were saying you were gonna take a year off. Not everybody has the resources to be able to take a year off. So I'm assuming that some of that was at least partially taken care of. Was this a…Did you three kind of have the idea that there wasn't any way that this was going to fail? That this was just going to, you knew the problem, you had the expertise and it was just kind of a guaranteed win?

Andrew Jamison: No, I think we all know that 99% of startups go to the wall. I think you're absolutely right. And I regularly talk about this, right? I give my wife credit for Extend because without her and the fact that her career went in a hockey stick direction, right? Is clearly one of the key parts of why I was even able to entertain this, right? We bootstrapped this for the best part of a year. That's why is because she was financing things behind and ensuring my kids were fed and all the important things were taken care of. 

And I think if you look at Guillaume, whose wife wasn't working, but now is working, there's always a big degree of personal sacrifice. You're making choices, right? You're deciding not to do different things. And obviously there's a difference there based on what income people have had in the past, et cetera, et cetera. And I don't even want to get into that debate, but the reality is we all make choices. And some of those involve bigger sacrifices than others, but you undeniably, right, you have to say, I find it really hard to think you could do this alone. And yeah, we all knuckle down. 

The beauty is my wife's a CFO, and she was like, “here's some milestones you're gonna have to hit if you want this to pay off” And so we look, we set out milestones because yes. you can easily let something drag on forever. And it just becomes an excuse to not go back to work. But look, we're all pretty motivated. And I think the key there was what were the milestones we were doing? And there were a couple of clear ones, right? Number one, we learned very quickly through speaking to investors, like, hey, investors are not that interested in investing in you. Unless you can convince friends and family that they should chip in first, right? Because if you can't get friends and family to invest in you, why on earth would us as professional investors go there? So that was one clear milestone. And then the second one was for us, we gave ourselves a deadline, right? If we couldn't raise money by the end of 2017, then it was like, okay, well, let's go and do a real job and earn money, even if it doesn't give us the same degree of pleasure and delight, right? We would go off and find jobs like we had in the past.

Ethan Peyton: And so you set these two big milestones and they're both very clear. If this by this date, then we keep going. If you hadn't hit those milestones or if you had set a goal to raise, I don't remember exactly what your first round of funding was, maybe 1.1 million or something like that, if I remember correctly. If you would have had on paper $700,000 you know, at the time when your first milestone came up, was it a black and white thought? Was it a, we didn't get it, we are not going to pursue any further? Or was there more of a nuanced feel to those milestones?

Andrew Jamison: So the friends and family for us was clear that the milestone that we had put in front of us was that we should not be investing a single actual dollar in the business because the time the three of us were doing and the fact we were bootstrapping was already a ton of dollars, right? It was well over a million bucks, right, in terms of lost salaries. And probably think double that.

And then the reality was, okay, so... If that's the case, then what's it going to take for us to get a couple of engineers offshore to go and build out that initial MVP that we took into a bakery? That was number one. Don't invest in a year of money. Get some money to build the back end. The second milestone was more about, I wanted to make sure we had enough money to give us at least a year and a half runway. So... If I was going to make 700, the question would have been, it's not 18 months. And the judgment would have been, do I think I can get the next funding round, right? To take us to the 18 months, right? Because it's never quite that cut and dried. 

But for me, it was like, if I'm going to ask other people to leave their jobs to come and join me, I better provide them a platform that gives them security for 18 months. Cause in today's world, 18 months, like a lifetime. And my view was if I can, get them on board and I can commit to them to that. It's a fair trade, right? It's a huge risk because it's always a risk. But hey, I'm giving you cash and giving you equity. Hopefully that aligns as well and say, let's give this damn good run for 18 months. And then we'll reassess, right? Somewhere 12 months down the line of where this is likely taking us.

Ethan Peyton: All right, so I'm curious if you have any kind of general advice for folks that are in a job, they want to start a company, they have an idea, what's the advice that you give them?

Andrew Jamison: So the number one thing I would say is an idea is worth nothing. I learned that the hard way. You can go around and pitch things, and unless you can actually get to a place where you can get rubber to meet the road, because you partner up with someone else who has the experience, who buys in on what you're doing, and get some form of a prototype out there, and get some degree of buying signals from the people you're going to be selling to…is really mission critical because it's too easy to get carried away in your own little world. And then you drag this on, you drag this on, and you pretend somewhere, somewhere on the line, that this is going to transform. I think you need to be super open to feedback, right, and criticism and some of the things that are less comfortable to deal with, because you really have to be able to do an out-of-body experience and do the outside looking in and saying, are you... Are you nuts? Right? Do you understand what this is? Right? And this goes back to, especially in today's environment, is there truly a moneification channel behind this? Will this ever make money and become profitable or is that just not even on the cards?

Ethan Peyton: All right, so you were in Amex. In fact, two of your three co-founders were within American Express. And looking at your site now, it's pretty obvious that there's a pretty strong bond between Extend and American Express. Can you tell us how the relationships that you built from within have helped to propel your business forward?

Andrew Jamison: Yeah, so I think one of the biggest values for American Express has always been around service. Amex prides itself on member sense. The whole point is I'm here for you and I'll always hopefully get to a place where I'm able to answer your queries and move you forwards. And that's something which we have taken on board as a team. And I've hired a number of people who are former Amex folks. 

But actually what I've realized is because Amex is a very unusual business and that it only really does credit cards. Okay, it's now going in other spaces, but for decades it has been really the premier provider of credit cards, certainly in commercial, globally. And so, you know, what you've seen is then employees over time have left to go to other banks and so it's created this incredible network actually of people. And one thing I'll always say is, I had tremendous relationships inside of American Express. Amex did a really good job hiring people and really crafting general managers. And it was really people who were maniacally focused because again, we didn't have the distraction of all these other products. 

So number one, the servicing side of things and a constant customer focus, two critical parts of really what I was looking for. When it comes to technology... You know, less so. Why? Because you know, Amex has been around for a long time and it has a lot of legacy technology that it has to continue improving on. But trying to adopt the latest and greatest technology every time is much harder, right? 

So for me, the beauty of being in a startup is, you have an ability to start with a clean slate, right? There is no debt there, debt quickly accumulates. And so for me, it was about saying, okay, I have a massive competitive advantage. And I start with. a clean slate, I get to pick the best to breed. And that gets me three to five years of clear advantage, right before some elements of technical debt step in on my side. So again, that was another thing was, where am I recruiting from? That's where Danny really played a really important role. Having come out of the consumer side of things, his whole thing was really about experience. How do you create some simplistic experience that takes you away from your nightmare of crawling into a closet? Because it's like, you have to be a rocket scientist to operate this damn dashboard, to how about we create more of a consumer-like experience inside of a commercial arena? And that really became a huge part of our focus. And even today remains one of our biggest differentiators, right, is the user experience and the servicing bundled together is what's allowing us to really build these relationships across the financial ecosystem.

Ethan Peyton: All right, so then we've got, you've got this business that is benefiting from the experience that you and your co-founder have built and the relationships that you've built over the years of being at this one company. And now I know that every company is different and you know, every person is different even within companies. And I understand that it's difficult to give kind of overall advice or standard advice for every different situation. But do you think that there are any good moves or positive items in the playbook that everyone can pull from if they are trying to start a company that is kind of I'm not going to call it a spin off, but you know, very related, something that you could have a relationship with that company as you build a new company. I know that was a very word salad question. So if you need me to repeat any of it, please say so.

Andrew Jamison: I think I got the gist, right? I think for me, the most important feedback is cover your bases. And what do I mean by that? The temptation, I think, often when you start a company is you're going to do it with somebody who's like-minded. And so before you know it, you're both salespeople, you're both marketing people, you're both product people. But I think the biggest value we've seen, and we're first-time entrepreneurs, so we're learning as we go, the biggest value I think we've gotten... And it's funny because we had this warning from investors like, ah, three founders, it's not really, it doesn't usually work out that well.

Ethan Peyton: Really?

Andrew Jamison: I think people talk about dilution and I'm like, that's great. But then in my mind, if you're worried about dilution, it's because you think the pie is this big. And I'm like, no, the pie is massive. So I'm not worried about dilution. That's not my, that's not my, my key concern. My key concern is making sure that we have perspective from lots of different angles. And so what I liked about, you know, being three, number one is, hey, we'll always get to a majority, right? There's never going to be the one-on-one or the absolute, which is also, I think, super dangerous, right? The absolute power of one. 

It was, we're going to keep each other in check, right? We've both, all three of us have had like really, really solid careers. And I think we therefore have learned, right? What leadership looks like. And I think we agreed, we can make mistakes and we can like, peel back and go forward in another direction. But it's almost like you agree to disagree, but you commit. And that's been super helpful. I think that the functional thing is really key as well, because I had more of that product lens, right? Product partnership and some degrees in sales lens. Guillaume had an amazing background in strategy and operations, having brought in some startups and brought them into Amex and really... made them operational in the context of a big blue chip company. 

And then you have Danny, who was this, you know, true, in my mind, light in terms of technology and design, but blending the two, right, which is again, a rare set of skills to blend really true hard technology with design. That's kind of… that's nirvana right there. And it's what you need. And so between the sort of business sense, the operational sense and the technology sense, we had a really stable base. And I think any company can do that. And by being founders, we kind of put ourselves on equal footing. And I think that was really, really helpful.

Ethan Peyton: All right, we're moving into the rhythm section of questions here, and I'm gonna ask my favorite question that I get to ask every episode, and that is what is your number one piece of advice for early stage entrepreneurs?

Andrew Jamison: I think the most important thing is be honest with yourself. It's rely on trusted friends and certainly mentors to give you a real read. It's so easy to go down the narrow tunnel. And sometimes opening up to really what's out there is really key. So that would be my biggest advice is seek that feedback. Pressure test all the time. your ideas and your concepts and be ready to evolve even if it feels uncomfortable. If it's uncomfortable you're learning and if you're learning you're probably doing something interesting.

Ethan Peyton: I think that's excellent advice. All right, what is next for Extend?

Andrew Jamison: Look, I think it's because we're really an infrastructure play, right? In terms of building this middleware with digital distribution, I think we're just at the very beginning of a journey. As I mentioned to you, the key for me is building this standard. Um, and by building that I build an exchange, right? And I've really become the exchange between a business technology world of, of procurement and the RPs and all these different things. And really then the integration. right into the banking system, right? And we start with commercial credit cards because it's a profitable line of business across the board, but it's also one that has not really been handled particularly well. So really for us to be that middleware, that translation layer between two complex ecosystems, I think is extremely challenging, but it really, I see a massive opportunity there over time. Again, all focused on, hey, let's reduce friction. for the ultimate beneficiary of this, which is the consumer of these applications, be they businesses or individuals.

Ethan Peyton: All right, Andrew, this has been a ton of fun. Last question, where can people connect with you online and how can our listeners support Extend?

Andrew Jamison: So connect with us online, certainly, obviously you can come to our website, I can obviously always be reached on LinkedIn or can be reached by email. It's andrew at And again, happy to support and help others in the ecosystem. I didn't get here without other people paying it forwards. And I think the key is just have thoughtful questions. And again, I think it spurs innovation in the end of itself. So I'm always, always happy to help there. Look, in terms of listeners, try it out, right? If you have an American Express business credit card or any of our other partners that we have out there, like Bank of Montreal, or you have a card with some of the other providers like PacWest and others, try it out. Register your card, see how simple it is, and let the dream come true.

Ethan Peyton: Awesome, that's and we're gonna put notes, excuse me, we're gonna put links to all those things over in the show notes at slash podcast. That's where you're gonna find everything else. You can find transcript, you can find all of everything we talked about here today, folks, and thank you for listening. Andrew, I'm gonna give you the last word.

Andrew Jamison: I want to say thank you for creating this platform. It's a great discussion. And look, more than anything else, I encourage people to go out there and try being an entrepreneur. It's a humbling experience, but it is incredibly fulfilling. And more than anything else, you just learn an awful amount about yourself and there's never anything bad that comes with that.

Ethan Peyton: All right, thank you very much. Cool, so then I'm gonna read an outro, but I won't do that until you're out. Hey, 431, we didn't do too bad.

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