Women Leaders in Payments: Dru Armstrong, CEO of AffiniPay | Episode 342

Discover the captivating journey of Dru Armstrong, CEO of AffiniPay, as she shares her unique path from growing up in Los Angeles influenced by her father's legal profession to taking the helm of a fintech powerhouse. Dru’s story is a testament to hard work, resilience, and the high expectations instilled by her entrepreneurial parents. She reveals how AffiniPay transformed from serving associations to dominating the legal and professional services payments landscape, while offering a personal glimpse into her life through a fun icebreaker segment.

From law to management consulting, private equity, and ultimately the CEO role, Dru Armstrong's career transitions are nothing short of inspiring. She emphasizes the pivotal role of mentors and sponsors in her journey, the shift from relying solely on analytical skills to the importance of emotional intelligence, and the critical need for trust-based teams. Dru candidly discusses the unique challenges she faced as a young CEO and underscores the importance of aligning with ethical investors and colleagues to achieve sustainable success.

Tune in to hear Dru's insightful reflections on leading through strategic change and growth, particularly in a thriving company like AffiniPay. She shares her thoughts on the value of mentorship, the importance of resilience in overcoming setbacks, and the joy of finding career roles that align with personal passions. Whether you're entering the fintech sector or navigating your own career path, Dru’s experiences and advice offer valuable lessons on authentic leadership, the power of mentorship, and the fulfillment of impactful work.

Transcript

Greg Myers: 0:04

Thank you for joining us during this special series running throughout the month of July, focused exclusively on women leaders and payments. We've got great content this month, focused on mentorship, career advice, getting out of your comfort zone, having your voice heard and much, much more. A special thanks to our contributing sponsors, stacks Payments, nuve and Map Advisors, and to our episode sponsors, nmi, dailypay, g&d and Ingenico. Hi everyone and welcome to the Leaders in Payments podcast. I'm Greg Myers, the host of the show, and today's special guest is Drew Armstrong, the CEO of AffiniPay. So, drew, thank you so much for being here. Welcome to the show and, more specifically, thank you for participating during Women Leaders in Payments Month.

Dru Armstrong: 0:50

Thank you, greg, I'm excited to be here.

Greg Myers: 0:53

Great, so tell our audience a little bit about yourself, maybe where you grew up, where you went to school, where you currently live, a few things like that.

Dru Armstrong: 1:00

Sure, so I'm Drew Armstrong. I'm the CEO of Affinipay. We're the market leader in legal and professional services payments. I grew up in Los Angeles, california. I was the daughter of a former federal prosecutor and attorney, which really impacted my story and obviously made me excited to lead Affinipay, which serves attorneys. I was the oldest daughter, which means I was the bossiest of three siblings, and I went to Columbia undergrad to study economics. I thought I was going to be a prosecutor and attorney like my dad. I ended up getting my JD MBA at the University of Chicago and ended up switching from law to business and really fell in love with business. I live in Austin, texas, with my husband, scott, and my two boys, wyatt and Finnegan, who are nine and six. They are the real bosses of our household, as you can imagine. Lots of energy, yeah, and I'm very fortunate because I live less than 10 minutes away from our headquarters here in Austin.

Greg Myers: 2:05

Nice, nice. Well, tell us a little more about Affinipay, if you don't mind.

Dru Armstrong: 2:10

Sure. So Affinipay. As I mentioned, we started actually in the association space and through that, amy Porter, our amazing founder, realized there was a massive opportunity to bring best-in-class digital payments into the legal market, because the bar associations were some of our very first clients. Today, we're the market leader in legal payments. We serve over a quarter million attorneys, over 60,000 law firms. And then we saw the same opportunity in the association vertical sorry, excuse me, the accounting vertical. So we discovered that accountants, like lawyers, really needed a simple, easy way to take digital payments for their very valuable work. So we've got about 10,000 accounting firms as our clients as well. And one thing to note is I'm actually a software person by trade and so I think the lens has always been digital payments as a core piece of professional services software that we're providing. What else can we provide? So two years ago, we did a very strategic acquisition and bought core legal practice management and have been investing behind the MyCase platform to serve our clients with everything from legal payments all the way through full legal practice management.

Greg Myers: 3:26

Great, all right. So before we get into the meat of the conversation, I'd like to do a little icebreaker exercise where I'm going to ask you sort of a this or that question, so something like do you prefer early morning or late evening? And you just give me the quick answer and we're going to run through 10 of these real quick, and are you ready to go?

Dru Armstrong: 3:45

I'm ready to go.

Greg Myers: 3:46

Okay. Do you prefer summer or winter, summer Cats or dogs, dogs, apple or Android, apple, coffee or tea, tea Books or movies, books, beach or mountains, beach Books, beach or mountains, beach Chocolate or vanilla Chocolate. Texting or calling. Texting the city or the country.

Dru Armstrong: 4:12

The city.

Greg Myers: 4:14

And finally pizza or pasta.

Dru Armstrong: 4:17

Oh, that's the hardest one, probably pasta.

Greg Myers: 4:21

Okay, great, all right. Well, thank you so much for doing that. That's a lot of fun. Hopefully some people learned some things about you that maybe they didn't know you might be getting chocolate donuts tomorrow.

Dru Armstrong: 4:30

I know exactly Gluten-free, so gluten non-gluten there you go.

Greg Myers: 4:36

I should have done that For all the donut buyers out there. Great. Well, let's talk a little bit about you. So what was your life like growing up?

Dru Armstrong: 4:45

So I grew up in what I would describe a very happy middle class family in Los Angeles. You know, my dad was, and he was a solo businessman. He was an entrepreneur though I don't think he would have called himself that. His heart was really in the law an entrepreneur, though I don't think he would have called himself that. His heart was really in the law. And so, you know, I grew up in a very tight-knit family. My parents were both from the East Coast and had moved to California when my dad started teaching at UCLA Law School. He then went on to be a prosecutor and then start his own practice.

Dru Armstrong: 5:19

So I think, from a positive perspective, I grew up with incredibly loving and supportive parents. You know my mom was the one who said you should get a JD MBA before anyone even knew what that was Now it's very trendy. They always really pushed and encouraged me to kind of realize my potential. So I remember I'd get my report card and if I didn't get straight A's because my mom thought I should be getting straight A's based on my capabilities it was going to be an issue, whereas my neighbors were delighted with C's because they viewed it as a passing grade. So I just grew up in a household with really high expectations around performing, and performing to the best of our own abilities.

Dru Armstrong: 6:00

I think the thing, though, that really kind of changed and motivated me was, while my dad was a great attorney, he was not a great businessman, and so he had really early days of success running his practice, and then he had many years of that were not good years financially, and I think because he wasn't a business person, he didn't kind of know how to better manage his business to be financially successful, and when you know your whole family is dependent on that business, it's really bumpy and challenging, and so I think it one.

Dru Armstrong: 6:35

It's become very inspiring to me in terms of what we do, because our core mission at Affinipay is to really ensure that the firm financially thrives right, because if the firm can thrive, the individuals thrive, and so that's a core part of our belief. With providing tools and I think payments at its core helps deliver that value right, our attorneys get paid faster, they get paid in full, and it really changes people's lives. I could see that with my dad, where collecting on the work he did was really challenging. So on one sense, I was very blessed. I recognized the privilege that came with parents that supported me to go to an Ivy League school and really pushed me to kind of dream bigger. On the flip side, I also recognized the pain that came from lack of financial stability and that motivated me, both in terms of how I think about my career and the stability I want to provide my family, but also in the work that we do serving, you know, small firms.

Greg Myers: 7:34

So when you were young, what did you want to be when you grew up?

Dru Armstrong: 7:38

I wanted to be a prosecutor and a litigator like my dad and then I got to law school and University of Chicago is very academic and I think the big dream there is to be a Supreme Court clerk or be on the Supreme Court. And I very quickly realized I was a fish out of water and I, you know, I worked at some different law firms in the summer and that just further proved the point to me that I was not well. I fully admired that people wanted that as their profession. It was not going to be mine.

Greg Myers: 8:09

I gotcha. So my very first job was working in the cafeteria at a college, washing pots and pans. And I remember I think I was 15, because I couldn't drive my mother worked at the college so she would take me. So all summer, long from 10 o'clock to 2 o'clock, I washed pots and pans. So that was my very first job. So what was your very first job?

Dru Armstrong: 8:32

So my parents were, as I mentioned, very academically focused, so I didn't have my first job I'm embarrassed to admit until college and it was my first summer between freshman and sophomore year and my parents had given their neighbor's friend his first job, which was painting their fence, his freshman year summer, and so he actually was running a movie studio in LA, which I think sounds very cool. I was the assistant to the assistant to the VP of business development and my job was to catalog the scripts and track the scripts and I could take scripts home and read them and I just really didn't like it. So it's funny, growing up in Hollywood it's such a one-horse town around the entertainment business and that was the closest I ever got to it and I appreciated the paycheck but it motivated me more actually to go on to law school and business school down the road.

Greg Myers: 9:33

Well, maybe walk us through your professional journey, your career. Maybe you know got out of college and then to where you are today and then to where you are today.

Dru Armstrong: 9:45

Yeah, I think one thing to just acknowledge is that I've always been someone who was really looking for places where I felt like I fit in and could add value. I think that's an important lesson and it's a hard lesson to learn, especially when we're younger in our career, in the sense that that may mean that you're at a great place or a great firm or a great firm or great company, but it doesn't fit you right, just like going to law school. So many of my classmates are now amazing practicing attorneys and happy with that career. So I spent a lot of my career kind of seeking out the right environments for me to feel like I was going to be successful and always looking for things with new challenges. Like I feel kind of still very young in my career I'm 42. And so I feel like I've got many more years to go. So I, you know, added my MBA.

Dru Armstrong: 10:37

Realizing law wasn't for me. I went into management consulting at the Boston Consulting Group, which I really think coming out of grad school or undergrad is the right time to work unbelievable hours and learn a ton and be a sponge. I think consulting or banking are great training grounds, depending on where you want to end up. So I did that. I then got recruited by a client which was one of the early tech private equity funds out of Los Angeles. They were starting a mid-market fund. I did that for a couple of years. I liked the work. I didn't like the culture of the firm.

Dru Armstrong: 11:12

I ended up doing a startup with one of my friend's husbands who had had success with a semiconductor company. I call that my god-laugh year because I found out I was pregnant. My husband had a lot of health issues that I had to help him with. We had a baby and I realized doing a software as a hardware plus software startup was going to take a long time and I needed to you know contribute financially. So I ended up going back into private equity. One of my old bosses was with a new fund, recruited me in to consult and then I ended up chief product officer and then CEO of that business for five years Grace Hill. It was doing people management software for the property management space. It was a pretty amazing learning experience.

Dru Armstrong: 11:58

And then I joined Affinipay after I had led that business for five years, had two successful exits to different investors and got really excited and intrigued about the Affinipay opportunity, which was my transparently my first payments experience. So no pressure, jumped right into learning payments, you know, with a hugely successful payments company. So a lot of kind of willingness to this is like so cheesy. But I always think one of the best pieces of business advice is the quote from the song the Gambler, which is like no one to hold them and no one to fold them. There are many years where you're like, oh my God, what am I doing here? Is this going anywhere? And you need mentors and career sponsors to say, no, you got to stick through it. I know you feel like you're not moving forward as fast as you should, but trust me, versus there are other times where you look around and you go, yeah, this isn't for me, it's time to move. And figuring those out, I think, is kind of half the battle in building a great career.

Greg Myers: 13:03

Absolutely Well. That brings us to today. So obviously you've been very successful throughout your career. What are some of your guiding principles?

Dru Armstrong: 13:12

So one is, I think that the comment I just made, which is like I'm an impatient person, I think a lot of high performance people are and careers are built in, you know, over decades right, and so knowing that it's okay to be patient and even if it means it takes a little bit longer in the short term, that can be not massively impactful, you know, relative to the payoff. The second thing is I've really, you know, I started my life in kind of more on the analytical side. More on the analytical side we can analyze the problem, we can be very IQ-oriented. I think the longer I go, the more the soft stuff is the hard stuff, where it's a lot about EQ, it's a lot about people, it's a lot about building high-performance teams that have diverse perspectives, can learn to really trust each other, can push through hard times. And then, I think you know someone told me like birds of a feather flock together. I think there's like I feel like I have a series of bumper stickers coming out of this, but it is really true that, you know, I feel like where I am right now is working with phenomenal investors that really see the world the same way I do.

Dru Armstrong: 14:25

Doesn't mean we always agree, but like from a core kind of ethics, integrity, how to build value. You know there's so many ways to build a business. Finding people that you really align with and click with, I think is actually really important, and I was talking to someone recently and he gave me the advice that, like good people who like each other whether it's good chemistry more often than not end up working together at kind of a surprising rate, especially when you're doing M&A transactions or investments. It feels like there's this big broad process or universe when in reality it can get very small and narrow quickly as you find who you really click with. And so I think honoring we teach ourselves it's so much about the intellect but a lot of why people buy is emotional. You know why people stay and work somewhere is emotional, and so I think the longer I've gone, the more I've learned to kind of honor not just the IQ but the EQ side of my role and of being in business.

Greg Myers: 15:25

Well, let's talk about your journey to becoming a leader. Were there some pivotal moments or experiences that helped shape your path?

Dru Armstrong: 15:34

You know, I think it's an interesting thing becoming a CEO at a young age. I got appointed to be CEO at 34 and it felt young. I know we have a lot of mythology in our culture right now about founders and how they're kind of the Mark Zuckerbergs coming out of college. I think a lot of the data shows that it's more like your 40s or 50s is when you really hit your stride, and so I think it took me a moment to kind of try to figure out like why me, why was I in that in the seat and how could I honor that? I think that's an important thing as CEO to have that awareness that there's a lot of responsibility that comes with it. You know we serve hundreds of thousands of clients that are doing essential work and getting paid through our platform, and you know I've got 500 employees who are looking to me to steer the ship, and so you know there was an awareness for me early on that I really felt called to leadership. I was class president for two years in a row in high school and that was kind of something.

Dru Armstrong: 16:38

I woke up one day and thought, gosh, that would be a great thing to do, you know, when I was given the opportunity, it was not an easy one to take. The company was going through a lot of tough changes and had a not good CEO right before me who had made a lot of negative decisions. So it was very much a kind of steer the ship through choppy waters which took, frankly, three years to get us on the other side of that cleanup. It took, frankly, three years to get us on the other side of that cleanup, and so I do think a lot of it's you know one being fearless, two, feeling called to it.

Dru Armstrong: 17:09

It's definitely not easy, it's definitely not for everyone. I think if you ask my husband we met in business school early on he would have said, yes, I want to be CEO Now. He's like definitely not. It's a really hard job, but I think, you know, I would encourage anyone. The world needs more great leaders who are thoughtful and aware and trying to do the right thing, and so I think people should be eyes wide open about it, but I don't think they should be afraid of it. And I think you know making sure that you do something where you feel somewhat set up for success as you take those risks, because there is risk that comes with stepping into bigger and bigger leadership roles. I think is important as well.

Greg Myers: 17:49

Okay, and what are some of the biggest challenges that you've faced as a female leader and how did you overcome them?

Dru Armstrong: 18:00

Gosh. Yeah, it's interesting. I mean we can talk about the woman thing right. There's very few of us. We haven't made a lot of progress in terms of the CEO seat. Less than 10% of CEOs are women. I think Fortune 500, we've kind of stayed steady at below 10%. I think we were celebrating when we were at like 11%, but really there hasn't been a lot of progress, whereas there has have in other C-suite positions and in board seats.

Dru Armstrong: 18:27

And so you know, my approach to it has been just to be my authentic self and to find the things that resonate with people as I'm leading, and that, I think, extends both to the board and investor level as well as to the executive team and employee level. So, you know, I don't think the model of trying to be something that you aren't works very well. I think we're in a generational change in terms of what people expect their leaders to do and how they expect them to act. They expect them to be more authentic and more transparent. Them to be more authentic and more transparent, and I think, as a woman who is the mom with young kids and you know, in some ways it might actually be easier for me to kind of meet the current employees where their expectations are, because I don't think I have much of a choice but to be transparent and authentic about that, and so I think that's a big part of who I am, I would say. I think I'm hopeful that we'll see, in the next couple of decades, more change and that we give more women the opportunity to lead.

Dru Armstrong: 19:31

You know, the easiest thing to do is to not hire someone as a CEO because they've never been CEO before.

Dru Armstrong: 19:38

Someone has to give you your CEO wings right, and so I think the biggest challenge, honestly, is continuously earning the right to be CEO.

Dru Armstrong: 19:47

I think that's hard for anyone, but I think we just have so few models of it in our culture where it's been successful. So in some ways, you just you have to one, know that that's there, but two, continue to perform and deliver results and do it in your own authentic way, without letting you know the knowledge that it's harder for you, kind of weigh you down right. There are moments it pops up and you go, oh my gosh, we wouldn't be having this conversation if I wasn't a woman. I don't mean this podcast, but you know you have these moments where you're like, oh my gosh, this is really not a conversation as a female, like a male CEO would have, but then you have to kind of look at that and then put it back down and just keep going has been my, my approach. So I do think it is harder, but I think if you're able to do it, I think it's there's a lot of opportunity to craft a new style of leadership that really does resonate with people.

Greg Myers: 20:43

Yeah, I completely agree. So let's talk a little bit about getting out of your comfort zone. That's an important topic that I like to talk about with these interviews. So can you share an experience where you've had to step out of your comfort zone, maybe to achieve professional growth, and sort of what impact did that have on your overall development?

Dru Armstrong: 21:06

Every CEO job is a stepping out of your comfort zone, right, because I think you're coming in. When I joined Affinipay in some ways it's counterintuitive. But I remember Matt Flake, who's the CEO of Q2, and on our board he said you know, drew, this is harder than a turnaround, this is a don't F it up, because the company was doing incredibly well financially and yet we knew that the market was changing and that software and payments were converging. And so, you know, I had my first CEO job when I was hired at Grace Hill was kind of a bit of a turnaround. My second chapter at Grace Hill, when I got a new investor in, was kind of a strategic expansion. When I got hired at Finapay, it was kind of we're at this large and high growth, high profitability business but we're pure play payments in a world where payments and software converging. What are we going to do with that? You know, creating a new chapter where we became a software plus payments and embedded fintech company. And so I think anytime you're charting a new course and anytime if you do strategic work, you don't go in knowing the answer right. You have hypotheses, but you need data and you need lots of stakeholder engagement, for lack of a better word, sorry, I'm still a consultant at heart at times. So that kind of not knowing, I think, is always a good time to step out of your comfort zone, because you're kind of going, you know everyone's looking at you saying, well, what's the new plan? And you're going, trust me, we're going to figure it out. It just takes some time, right.

Dru Armstrong: 22:43

I think the other piece is when I joined Affinipay back to being an amazing business, I had really big shoes to fill. Amy Porter is an amazing leader, an amazing founder, and she had her own style and the company really needed fresh leadership, right in the sense that she was, you know, on the board and ready for her new chapter. And so figuring out how to kind of step in at a company that had great culture, great employee engagement, doing super well, you know, and so you kind of were like, okay, well, how do I do this, but in my own way? And how do I start charting a new course and bringing people along when there's a lot of love and loyalty to the past, right, both strategically and emotionally, to our founder and to its early days, and so I think that was another big stepping out of my comfort zone and I think anyone who's gone through a founder to professional CEO transition.

Dru Armstrong: 23:42

I will tell you the number one thing when I interview executives because we're currently recruiting for a couple of key executive roles the number one point of failure usually in someone's resume is they stepped in and they were trying to execute a founder to CEO transition and it failed, and so I didn't realize how big a deal that was going in.

Dru Armstrong: 24:04

It's actually the second time I did it, so you know, now I finally got it. It's a big deal, but I think that's a really big deal and I think if someone called me up with a job saying, hey, do you want to come back fill a founder? You know you have. That is very much a challenging thing to execute and pull off, and so I feel really good that Amy and I were able to execute that transition with our board support over the past three years. Look, the great thing about being a CEO is the job changes like every year, every day, every month, and so there's always something taking you out of your comfort zone and you either like it and learn to live with that or you don't, and it's probably the wrong job for you, right?

Greg Myers: 24:45

Right, right, right. I think the days for even you know any employee, whether it's the CEO or whatever role they're in it seems like things just move so much faster. You don't just sit around and do the same thing over and over. There's always change. There's always opportunities to do new and different things that you have to get out of your comfort zone to be successful.

Dru Armstrong: 25:08

I think you're exactly spot on. I think the interesting dynamic that we have to manage right now is that the rate of change has ratcheted up massively and COVID was a massive accelerant to that in terms of fundamentally shifting how we work, our expectations of each other technology plus COVID, plus all the social change that we've seen. And then, on the other hand, I do think teams and companies thrive with structure and planning and the ability to kind of plant seeds and watch them grow right, and it's hard to execute on a massive strategic change and drive massive growth if you aren't planning for that in advance. Right, whether that's quarter, you know months, quarters, years, and so I think the dance that we do is how to balance the speed with the thoughtfulness.

Dru Armstrong: 26:05

One of our new core values is work smart, win fast, because on one hand, you want urgency and pace and the whole world's competitive. If you're in a good market, people want to win and they want to take what I believe is rightfully ours, for example, but on the other hand, you need to let things have time to gestate and to grow. I think embedded fintech, which in my opinion, is the future of embedded payments, where we're kind of bringing all of the banking capabilities to bear. In the same way digital payments have across software platforms. Each of those new products that we do takes two years to gestate and bring to market because it's so multi-layered, and so I think that's the dance. That we all have to do is figuring out. You know how to go fast, but how to go fast at things that may take many years to actually bring to market or bring to fruition?

Greg Myers: 26:57

Right, right, Totally agree. So let's talk about mentorship. So have you had mentors in your career and you know just overall, discuss your view on mentorship. How important do you think it is to emerging leaders? Maybe some experiences you've had with mentors?

Dru Armstrong: 27:15

Mentors and career sponsors are really why I am where I am today. I think there's a lot of data to show that people who have exponential career growth it's because of mentors and, really, career sponsors. So, someone the difference, in my opinion, a mentor is someone who, long-term, is invested in your success and will always be a thought partner to you and you get to benefit. Wisdom is learning from other people's mistakes right, and so they give you the opportunity to be wise, because they give you advice that you may or may not like and you hopefully heed it. And then sponsors actually like open the door and give you your first CEO job or give you your promotion or let you take on the special project or present to the board, whatever it is. I think both of those are hugely important.

Dru Armstrong: 28:04

I also think that they're earned right, and I don't think that, you know, I don't think that you can kind of like blindly matchmake, like an arranged mentor-mentee marriage, and so I think one of the things we have to think about as we move into a more remote work environment is to make sure that those kind of soft connections that are ultimately hugely impactful continue to get built, like my mentors that I had, it came from working on deals together in war rooms and crazy situations and they've stayed my mentors for over a decade and been kind of invaluable to me. And so I would say I think the world where, on one hand, we get a lot of benefit from going remote, like I can be sitting on my laptop, I could be on the beach in Bali and we could be talking. Right now I'm unfortunately not. I thought you were. Yeah, I know I should be with a pina colada and on the beach no waves crashing.

Dru Armstrong: 28:58

So I think we get a lot more flexibility, which I love. Imagine me with a pina colada on the beach, no waves crashing. So I think we get a lot more flexibility, which I love. I think it's hugely impactful. But, on the other hand, I think making sure that folks building their career get enough exposure and I hate to say it, but oftentimes being in person is a better way to get that exposure and working the long hours and proving yourself, so finding that balance of the flexibility that we want but also kind of the ability to be in person and build those really valuable relationships, because I do think long-term they make the biggest difference to one's career.

Greg Myers: 29:34

Yeah, and we often hear about bigger companies have dedicated programs just to mentorship or finding mentors, and obviously there are organizations outside of companies ETA and Women in Payments and companies like that that definitely have programs and can help. I feel like there's sort of this misconception for younger employees that hey, I have to be a part of a program or whatever. And I think what I've learned just over doing kind of these type of conversations in the last couple of years is really, you know, you have to take ownership of that, right, you can't wait right.

Greg Myers: 30:13

You can't wait for a program to be developed by your company. You have to go out, build the relationships and I think sometimes mentor is a bad word because it has a certain connotation to it but at the end of the day it's like you have to take responsibility to build the relationships and keep them going. And it doesn't have to be so formal that you have, you know, monthly or quarterly appointments and you know, sometimes mentors pop up in strange places. They could be bosses, they could be people that you, people that are colleagues, they could be from anywhere. But I think that ownership of that is what a lot of people, at least up and coming people, need to understand and focus on.

Dru Armstrong: 30:51

I mean, I 100% agree A couple of things that you said. Just to echo is one I think mentors are earned right, and I think we shouldn't be afraid to ask someone to be our mentor, and you don't have to say it in those words. It could be more subtle than that. I think that's true on multiple levels. Right. It's like any relationship One.

Dru Armstrong: 31:14

You know, what I see from hugely successful people is there is a point in their career where they go oh my gosh, I've kind of made it. Whatever that looks like. It can be financial, it can be stature. Now I really want to kind of give back and be pulling people up behind me, or even building my team of people who are going to ultimately take over for me. It can be succession. It can be more altruistic than that.

Dru Armstrong: 31:38

I think it needs to be earned in the sense that they feel like you're a good investment, and that can go both from your raw natural talents and abilities and potential, but also in your willingness to listen. I mean, I'm sure you have the friend who always wants to go to lunch and never takes your advice and you're like how many times can we talk about this? You wanted my advice, I gave it to you, now are you going to do anything with it Right? So I advice I gave it to you, now you're are you going to do anything with it, right? And so I think a lot about it doesn't mean I take all the advice of all my mentors all the time. That's not realistic. But you know the mentors, like they would say, one of my great attributes is that I'm very coachable right as successful as I am. I certainly don't feel like I've quote unquote made it, and when people give me advice, I really try to listen and be thoughtful, even if it's advice that I don't want to hear Right back to. Sometimes they'll say you need to finish out this chapter at this company, or you need to have some more hard conversations or look in the mirror on why you're not being successful, whatever it is.

Dru Armstrong: 32:35

I think that's some of the most important advice, and I guess the second piece I'd say is I've never had a mentor come from a formal program, and so I think if you're waiting for the quote unquote company to matchmake you know I'm not saying it can't ever be successful the approach that our head of people has taken for our. We have been a nascent mentor, mentee program at Affinipay and I like the approach she's taken, which is people ask both senior leader and individual contributor, right, are asking to be enrolled in it, and then they can ask and there's kind of a matchmaking process where people are saying, hey, can you give us some more structure? But already I'm gravitating towards being, you know, connected with this person. I want to get their specific input. So I like more of the pull model where you're saying, hey, I'm looking up, I'm seeing Christian, our CFO.

Dru Armstrong: 33:28

He's amazing at these things. How can I do that? Would Christian be willing to mentor me? And likewise, christian has an ability to say, hey, here's who I think would be. You know, I'd really enjoy men. It has to kind of go both ways. So I'm not saying it can't be done, I just would be skeptical. And I would say the nice thing is, you know, you can start cultivating a mentor tomorrow, right? It's like can we get a coffee? Here's the things I'm thinking about. Do you mind if I ask you here's why? I really admire you and you'd be surprised at how many people respond to that, especially if there's follow through and they see you taking the advice. And it's very rewarding to watch people build their careers, you know, and to feel like you're having a hand in that.

Greg Myers: 34:10

Right, right. Well, so far we've talked about a lot of the positive things and things people can do to further their career. But I think, if we're realistic, we've all faced some kind of setback or failure. So can you share any instance, maybe, where you had sort of a setback, and then how did you handle it and what did you learn from it?

Dru Armstrong: 34:30

Yeah, it's a great question. I mean I feel like you know it's funny.

Dru Armstrong: 34:35

I think the Roger Federer graduation speech is kind of going viral where he said, you know even the best tennis players, he's won almost 80% of his matches, but he's only won like just slightly north of 50% of his points. And so his point is like you're always kind of, there's a lot, there's micro failures, there's larger failures. You know there's a lot of winning and losing that can add up to ultimately having a winning career. And it's really how you handle that with resilience. And I think one of the biggest attributes that I see in having a great career is just the resilience that getting knocked down. It can be a competitor launches a feature before you. It can be you lose a deal. It can be you lose a customer, can be a key team member quits. You don't get a promotion. You don't get the investment you want. There's like a whole, so many ways that every day or every month or every quarter years, whatever it can feel like the losses add up. It's, in my opinion, more about how you navigate through that.

Dru Armstrong: 35:37

I think one of the defining feelings I had of losing was when I first became CEO of Grace Hill and there had been a commitment made by my predecessor about launching a new platform without dates, without enough due diligence, and then getting pushed by the investors to get it live before it was really ready, and then taking our clients through what was a very unhappy and successful migration, and I measure the lack of success by how unhappy our clients were and how much churn there was, which is the enemy of any software business. And so I think what that taught me was where I failed in. That was not in the original decision making, but it was in, you know, not being courageous enough as CEO to say, hey, wait a second, like we have to do this the right way, like we owe that to our customers, we owe that ultimately to our investors, even if they think, you know there's it's more important to go fast and not really taking the time or feeling like I had the permission to do that. I mean, some of it was situational, but I think, as CEO, it's important to take responsibility, and so I'm actually thankful that I had that experience though, because, as I mentioned it, I'm like big picture, go fast, and so I really try to have a great team around me that have other kind of more process-driven, kind of more detail-oriented. I have a lot of people who are kind of if I'm the gas, I got a lot of brakes around me so that as I think about going fast and making bigger moves, that I make sure that it's really going to feel like a win for all the stakeholders and sometimes inside of companies, we can get caught up in our own goals, what we told the board and ultimately we have a great business because our customers love us.

Dru Armstrong: 37:31

And the worst feeling was making a whole industry I was not even six months in or one year in making a whole industry of people really mad at me and it felt very personal. I think part of being a CEO is you take it really personal and so and I stayed and worked and we cleaned it up and the business thrived and so it has a happy ending. But you know, I think you know it's really having the courage to take steps back and you know slow things down if needed or even mothball things, because you know you realize the original assumptions weren't the right one and you're always going. Is it better to kind of eat crow now and kill the project or, you know, push it out a year, or would I rather have thousands of clients angry at me and canceling their contracts?

Dru Armstrong: 38:25

I'm going to tell you, the willingness to be patient is always the right choice, and I would say it still kind of guides my ethos as a software leader, where there's a lot of desire to just go fast, break things, but we've got over 100,000 firms using our platform.

Dru Armstrong: 38:42

We need to be able to launch new products and invest in our platforms, but we also need to ultimately do it in the right way, and so I think that was one of those early, really painful lessons that I learned. I mean there's so many, right. I mean I shuttered a startup. You know I've all that. There's like lots of other failures that I've had, but I would say that is still the one that felt the most painful, just because of the magnitude of pain it created with our customers and our business, and ultimately, it was great to see it get cleaned up and I learned a ton from it, and I always tell my team today you get the benefit of all the lessons learned from the prior eight years. Right, that's the good news. As CEO, you get a better and better pattern recognition as you go along.

Greg Myers: 39:28

Yeah, I appreciate you sharing that. I mean, I know that can be a touchy subject for some people, so thanks for sharing that. So let's think through this scenario. Say someone, a young woman, graduates from college. She sees payments or fintech as an industry she's interested in building a career in. If she came to you and said, drew hey, what do I need to do to be successful in payments? What would you tell her?

Dru Armstrong: 39:52

Yeah, I mean, I think the question really is about because I think one mistake that the payments industry makes and it's funny I was having dinner with Simon, the CEO of Marketa, and we were kind of laughing that, like payments is the only industry that explains the how we do it versus the what we do, you know where, at the end of the day, it's as much software, and software does a really good job of saying, hey, here's the pain points we're going to be able to solve, you know for you and don't worry about what happens behind the curtains. I think payments were a little bit. We have an opportunity to better articulate, like how we really impact our clients and do it like payments. There's so many different flavors of payments companies, so one I would say like, think about what problems and what groups of people like what problems and what groups of people you want to go solve those for. I find it very compelling that for our attorneys and accountants that use our platform and while it's quote-unquote payments, it's really software. There's all this workflow built around it and oftentimes they're putting it in place before they're buying even the software they use to run their practice. It's the first piece of software they're putting in place in order to get their invoices paid, because there's a massive leakage, write-off problem in our industry and they need to do it, especially in the legal space, in a compliant way. And so I would say find the places where you're really passionate about solving the problems. And you can do that from the sales angle, where you're helping, you know, the SMB attorney figure out what the right solution is for them. You can do it from a customer support angle. You can do it onboarding, getting them set up. You can do it from a coding perspective where you're, like you know, actually making the sausage. You can do it from marketing.

Dru Armstrong: 41:48

But, like there's a lot of, it's kind of like what do you gravitate towards? Is it solving problems for businesses or consumers, you know? And then where in that value chain do you think, like, your gifts are most applicable? I think a big transition is like there's the high school model where we need, we're told, we have to be good at everything. Right, I mean, I have no musical capabilities and you know I took cello and guitar for years. That was part of my Columbia application. I did, but am I good at it? No, I'm terrible at it, you know. And then suddenly it switches on you. You get to college and beyond and it's about what are you uniquely gifted at right and and then if you figure out those gifts, then are you able to lead other people who are gifted with that right. So it kind of switches, you know, and does a 180.

Dru Armstrong: 42:38

And so my, my biggest encouragement is, I think you know, find what your gifts are and pattern match it to things that you're passionate about. And one piece of advice we didn't talk about this, but I went to culinary school in between undergrad and grad school and I realized, like I love to cook for fun, not for work. So figuring out the dividing line between work, like what you find that you're passionate about at work, versus what you're passionate about just for fun, is an important area to draw the line. You know, like for me, I love movies. I didn't want to work in a movie studio.

Dru Armstrong: 43:13

And then I'd say I think the industry, like, look for industries where there's a lot of growth and a lot of innovation, because that creates job security, right, and it means there's going to be new and exciting ways to apply all the innovation that's going on to really important problems.

Dru Armstrong: 43:31

And so I mean I never thought I would say this, but, like legal tech is really sexy and exciting.

Dru Armstrong: 43:36

We've got a massive industry, lawyers are just now adopting technology, and yet we know payments and embedded FinTech and general AI all are going to drive massive change to this industry over the next decade, and so look for places where there really is organic growth, because with growth comes job opportunities, especially responsible growth.

Dru Armstrong: 43:59

I think the correction that we've seen in the past couple of years where you couldn't just be growth at all costs unless you're maybe a certain very specific type of business, but businesses that are, you know, growing, are profitable, have thoughtful ways around how to spend and grow, and I would say I wouldn't underestimate looking at that and asking those questions, because you know part of how you're going to build wealth as a young person is the equity that you're going to be given in a public company, a private company, and so I'd say kind of number one is payments is an amazing industry going through a lot of transformation with a lot of innovation.

Dru Armstrong: 44:36

I think you know embedded payments, embedded fintech there's so much more to do and then picking industries where it has the biggest opportunity to transform and then picking the companies that you feel like are responsibly led with good organic growth and good thoughtfulness about how they spend money. If your budgeting process is your goal is to spend it all and more, probably hasn't gone through the right correction on thinking about profitable growth, because I think that is here to stay for a while.

Greg Myers: 45:05

I think that's all great advice. I appreciate you sharing that. Well, let's wrap up with one final question. Who or what inspires you to keep pushing forward in your career?

Dru Armstrong: 45:17

I mean, honestly, I think it's just innate in who I am. For me, I kind of look, what really lights my fire is just the ability to have impact and to have impact with our team and to really impact our industries. And so I think one thing that is interesting is this idea of having made it I'm doing air quotes which is the reality is, I think, if you are passionate and inspired I'm not saying we don't need to take vacations or it's still a job, right, you know, it's not the same thing as being on a yacht in Capri I don't know, I haven't been, but I would imagine like it's still a job, but like finding things, that kind of light your fire and, honestly, the easier it feels for you, the more you're probably doing the right job right, the more you're like days. I can't tell the difference between work and not work, because I can't believe I get to do this as my job. I think it makes you want to keep going, and I remember thinking when I took the Affinipay job, because the company was two and a half times larger than the one I had been running I was like, oh my God, I'm going to get to run a company with 200 employees and at the time we were a hundred million in revenue. I was like this is crazy. And you know, now we're multiples bigger than that and I'm running team multiples bigger and I'm like, oh my God, what will it be like when I'm running a company with a billion in revenue? And so I think you keep having these moments of like oh my God, look at the impact and look at the cool things we get to do, and what if I get to work with that investor and then, before you know it, they become your investor.

Dru Armstrong: 46:50

I think, as long as you have that fire and passion, like, there's a lot of opportunity to provide leadership and to contribute. And it's funny, one of my mentors, bob Pryor, who's the CEO of NTT Data amazing guy, that's a massive business. He just quote unquote retired and he's like Drew, I'm going to be even more busy than I was a CEO. I'm going to be chairman of one of their boards, I'm going to be running their venture arm, and he's like but you know, the data's there. Once you retire, the odds of dying in the first two years way goes up. And so I think there's something about.

Dru Armstrong: 47:27

You know, one of my. I have this amazing CTO, brian Thompson. He was the CTO at Heartland Payments and he was at Beyond Payments and now he's our CTO and he had a year non-compete where he kind of sat on the sidelines and he's like Drew, the first couple months were great. You know, I golfed, he has a big property outside of Dallas, I all the things right. And then he's like by like month four I was so bored. So, you know, I just would say I think there's a lot of impact. Careers can change, you know. You can go from being in a company to boards, to advising all these different things. But for me it's just the ability to continue to have impact and feeling like I'm pretty young and there's a lot more to do out there. So, and when it stops being fun, then I'll let you know.

Greg Myers: 48:13

There you go. All right, great. Well, thanks for sharing that and thank you so much for being on the show. I really enjoyed our conversation. You shared some great things. I think there are some bumper stickers that we'll maybe produce for this one, but no, seriously, thank you so much for being on the show. I know your time is very valuable, so I really appreciate you being here.

Dru Armstrong: 48:33

Thanks for having me, Greg. I really enjoyed the conversation and appreciated you letting me be on your show.

Greg Myers: 48:40

Absolutely, and to all you listeners out there. I thank you for your time as well and until the next story. Thank you for your time as well, and until the next story. A special thanks to our sponsors for helping make this month possible, especially our contributing sponsors Stacks Payments, nuve and Map Advisors, and to our episode sponsors NMI, daily Pay, g&d and Ingenica. To learn more, visit wwwleadersinpaymentscom.