Computer programmers may have the best ideas in their minds, but they are worthless if they cannot communicate them clearly to other people. David Barrett, CEO of Expensify, joins Amy Vetter to share how to cross the imagination gap by being an excellent communicator both verbally and on paper. He looks back on falling in love with computer programming at the age of six and the story behind the genesis of Expensify. David also discusses the secret of his career success, detailing how to stay positive despite the negativities he faced along the way, the importance of humility in leadership, and the power of framing success regardless of other people’s expectations.

We are honored that Expensify sponsored this episode. Expensify is a payment super-app that helps individuals and businesses simplify the way they manage money. More than 12 million people use Expensify’s free features, which include corporate cards, expense tracking, next-day reimbursement, invoicing, bill pay, global reimbursement, and travel booking, all in one app.

To learn more about how Expensify can help save you time to focus on what really matters, check out use.expensify.com/spend-management.

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In Between It All Is The "Imagination Gap" With David Barrett CEO Of Expensify

I interviewed David Barrett, the CEO of Expensify. David is a lifelong programmer who founded Expensify in 2008 and built it into the most popular pre-accounting platform on the planet. He is recognized as one of the world's top network engineers, having created the Expensify blockchain-powered database a year before Satoshi's Whitepaper on Bitcoin. Prior to Expensify, David led engineering for Red Swoosh, which was acquired by Akamai Technologies in 2007 and held various roles in 3D graphics and VR development. When he's not fearlessly leading team Expensify from Portland, David enjoys playing Minecraft with his daughter.

During this episode, David and I talked about how he started programming at the age of six, which eventually took him on this journey to be the Founder of Expensify. David realized through the years that even though he was told he was a math geek, he learned to shut out the noise and realized he had so much more to offer the world by not only believing in his dreams but also his bigger mission and shutting out the outside noise.

This episode is sponsored by Expensify. We are honored that Expensify is sponsoring this episode. They are a payment super app that helps individuals and businesses simplify the way they manage money. More than 12 million people use Expensify's free features, which include corporate cards, expense tracking, next-day reimbursement, invoicing, bill pay, global reimbursement, and travel booking, all in one app. To learn more about how Expensify can help save you time to focus on what matters, check out Use.Expensify.com/SpendManagement. I hope you enjoyed this episode. There are many great lessons from David in my conversation with him. I am sure you are going to share this with the people that you know who can benefit from it.

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I'm very excited to talk to David Barrett from Expensify. David, do you want to give a little background on yourself before we start, and then we'll get into your story?

I'm 47, so there is a lot of background, but I quickly summarize as I've been a computer programmer since I was six. I did video games and 3D graphics are my jam. I worked in the Virtual Reality Lab at the University of Michigan. I worked in game industry technology for a couple of years after college. I went into a push to talk video conferencing and peer-to-peer content distribution. It's an unlikely background for the extension board magnate that I've become, but it's been a wandering journey. It's gotten me here and I love it.

I can't wait to get into it. Where did you grow up and what were your parents' occupations? What did they do?

I grew up orbiting Lake Michigan. I was born in Michigan, then moved outside of Chicago, then to Wisconsin and then back to Michigan. My mom was a nurse. My dad was a salesman for something like giant industrial robots, like these huge arms that would pick up pieces of cars and move them around and things like that. He basically sold to the auto industry. We moved around the Great Lakes Region and focused on that.

Did he take you to see these robots?

I have only one memory of that. It was a great memory because this huge robotic arm would basically go and pick up a car or something like that, set it down and then grab this bucket full of gumballs and pour it out in a drawer in front of us. That impressed upon me.

Isn't that amazing what we hold? Did you have brothers and sisters? What was your childhood like?

I have one brother. He's two years older than me. When we were younger, we looked at identical. It was weird. We had the same hair and the same build. I remember one time I was in the front room with my cousins, whom I would see once a year or something like that. I was talking to her in the front and then she walked back to the kitchen and saw my brother there. She did this double take. She was like, “I was just talking to you. Did you change your shirt? What happened?”

Even though we ended up looking very similar or at least we did for a while, when we were kids, he became full-sized super early. He's 6 feet tall, but he got there super early. He was this giant. He was into skating. He had chains, leather, skulls, a skateboard and long hair. At the time, growing up, skating meant that you were definitely satanic. Now it's the most wholesome sport in the world. Back then, it was basically the mark of the devil. I liked rainbows. I wear a T-shirt with some dolphins or something like that. We have very different personality types.

What was it about your personality? What were you drawn to when you were younger?

I started programming young because we lived in the middle of nowhere. As a result, I didn't have anything better to do. It's our house. It’s me and my brother, and then we had one neighbor with no kids. It was farm fields as far as you could see. Our closest friend was something like a mile and that's if you cut through all the fields. I was very shy. I was smart but bad in school because I didn't care. I got a computer early. My dad traded a trailer hitch for it or something like that. I got this VIC-20 computer. That was my thing.

Nowadays, we view computer programmers as wizards like, “They're building the future.” Back then, it was this oddity. It was viewed as a weird offshoot of math for some reason. Everyone thinks computers have something to do with math. I don't know anything about math. Anyway, I was a weird kid on this computer and I’m like, “What is that thing?”

It's important for people who are younger to know that a computer at that time was pretty big.

It was a large-ish or something like that. You had to bring your own TV and plug into it. For most of my life, I didn't know a single computer programmer. I never even met a computer programmer until college. This is pre-internet. I would go to the bookstore and read a book in the bookstore because I couldn't afford the books about programming.

How would you even know what it does or find out about it? Why were you fascinated with it?

I like computer games. Early on, I saw a video game and I'm like, “That's cool. I want to make that,” and then I saw 3D graphics and I'm like, “I definitely want to do that.” There was this thing called BBS, which is where modems would connect. It's like a website that only one person can access at a time by dialing in. I'm like, “I'm going to take video games plus video graphics and combine it with modems. That would be cool,” then the internet came out and I'm like, “Screw modems. I want to do internet. That's super cool.”

I was about trying to make video games and then I made video games after college. I realized I spent so much time working on my game that I didn't even want to play my own game. It felt like such a waste of my time to play my own game. I had this epiphany. I'm like, “If I can't even justify the time to play my own game, how can I excuse anyone else doing this stuff? My success is measured by how much time I squander someone of else. That doesn't feel good.” I left gaming and then went into much more useful practices.

What type of game-making?

My very first game I loved. This game is called Ultima IV. Looking down from the top, you can see a map, you can walk around and go on adventures and things like that. That was very basic graphics, but it was this huge world that you could explore. You get lost in this world for ages and then come out this game called Wolfenstein 3D. It was the first game where you could see through your eyes and run around. I'm like, “This is mindblowing.” I wanted to combine Ultima with this with the internet, then basically started trying to build a massively multiplayer roleplaying game back in the day.

The company I ultimately joined was a motorcycle racing simulation. One thing I learned a lot along the way was the game industry is big. The industry for simulations is very small. For motorcycle simulations, it is basically nonexistent. I learned an important lesson. It doesn't matter how good your code is. If there are no customers, it doesn't matter. We worked for years in this game and no one bought it. I'm like, “My part I was very proud of. I did my job, but someone else picked the genre of our game that was someone else's job and they screwed that one up. That's an important thing.” Any member of the team can ruin it for everyone else.

When you were creating this on your own, because it sounds like you were pretty much alone a lot of times or you didn't have a lot of people around you, did video games give you a community or character?

Not really, because it didn't have a community. It's just me, but it gave me an outlet because the great thing about programming is you can build anything you can imagine. As a result, it's much instant gratification because you sit down in front of a computer and you control every single variable. You quickly learn that everything is your fault. If something doesn't go right, it's because you programmed it wrong. There's no one else to blame.

It drives a lot of accountability, but there's so much pride when you have something that comes out. You're like, “This is amazing. I did this. It wouldn't exist if it weren't for me.” It's an exciting field because it's creative and it's interesting. It's not perceived as creative. People see programming as like math. They are like, “There's nothing creative about that. That's not real art.” I'm like, “I disagree. I think it is extraordinarily complicated and beautiful art.”

You can tell me if I'm wrong. I've worked in a number of tech companies and met with programmers in trying to get different features built. From the accounting side, I was going in and saying, “We need this.” I would sometimes have a hard time for them to understand what they were building. They were very much about programming, but there was one instance in particular. I brought customers that were computer programmers. I had them explain how they're using the software and what it's solving for them, talking about different features that are important to them and why.

When they left, I talked to the programmers and they were like, “I didn't even know that's what I built. I didn't know that's what I did on the other side.” There's got to be people that like the math and the programming, and then there's the people that like the creative visioning of programming. You can tell me because I'm not a programmer, but that was shocking for me.

That's incredibly common where, up until Expensify, I had never built anything that was for me. Most of your job is building something for someone else. It's building some tool that someone who isn't you is going to use. It's like, “I'm not an accountant, but I build tools for accountants.” You have to imagine this entirely different job in order to do your job.

That's quite hard. It was the imagination gap. When you're trying to describe an idea to someone, in your mind, you've got this powerful, amazing, sophisticated thing that took you years to figure out and then you condense it down to 100 words that you communicate to someone else. They expand that into something else that’s completely different, which isn’t what you have in mind at all.

It’s hard to know that because there’s a limit to what they’re able to imagine. You can limit how effectively you can communicate what you’re imagining. That’s tough. That’s why it’s effective to bring in people who’ve lived the job who can tell stories about it, make it real, and show it in practice because it helps someone imagine what you’re trying to do, even if you correctly described it.

If they don’t have the context to understand the words that you used, it didn’t come through and land. What you said is not necessarily what they heard, but what they heard is what they’re going to build. Sometimes, what they hear is nonsense. That doesn’t make any sense, but like, “Whatever, you’re the client.” They build it for you and you’re like, “This isn’t what I want.” They’re like, “I thought you wanted it.”

I went into accounting because I was made to go into accounting in my life. What I wanted to do was be in art. There was a period of time and it was a while back where I was trying to figure out, “Do I want to stay in this area or profession? Do I want to go back to school and try what this would be?” There’s a top design school in Ohio. I went, and the dean was talking.

I was like, “This is exactly what happens in tech companies all the time,” because I went for fashion design. I wanted to see what it would be like to do that. He was talking about how designers come into the field because they get to create anything that they want, but you are there to serve the needs of your customers who are coming to you. Someone's got to be that intermediary communicator that understands both sides.

He was talking about this fantastic project where they went out to another school for them to solve a problem. They went to the medical school and said, “What do you want the fashion designers to solve for you?” What they said was, “When people put on a hospital gown, they get sicker. Design a hospital gown that someone doesn't feel sicker.” I was like, “That's fantastic. That's exciting.” You don't go into fashion design thinking you're going to be designing hospital gowns. Computer programming is the same situation where you're trying to solve other people's issues and then interpret it that you solve that, which is hard.

So much of it is trying to put yourself into the shoes of the clients. The most fun as a programmer is when you're scratching your own itch and when you're solving a problem that you've personally experienced. That's an exciting time because then you don't have to talk to anyone. You can start building what you need and you are like, “At least there's one person on the planet that will like this.” Odds are you're not that special. If you like it, probably other people will. That'll only get you far, but at least it'll get you to a start.

Let's talk about your journey. You went to college for computer programming.

I went to the University of Michigan and got a degree in Computer Engineering there.

How did you feel about that?

I hated it because going to college for computer programming is the dumbest thing in the world. It was then and is now because there's nothing you can't learn with an internet connection in your basement. You can learn it so much better by yourself. I'm not going to say this is true for all fields, but when it comes to computer programming, there's a very strong inverse correlation between how long you spent in school and how useful you are as an engineer.

If you didn't go to school at all, you're probably great. If you only went for a Bachelor's degree, you can recover from that. Master's, it starts to get tricky. If you have a PhD in Computer Science, that's tough because you've learned much of the wrong thing. It has to be unlearned. I'd say the internet is designed by programmers for programmers to teach people how to program. There are many good resources out there.

You're saying it's like the street smarts. If you're passionate enough about it, you're going to want to be tinkering, playing and trying to develop these things on your own without being taught.

At Expensify, we talked about the three major core qualities. One of the first of these qualities is talent. Talent is the ability to learn without being taught and then teach others what you know. A talented person absorbs knowledge from all around them, condenses it, and shares it with others. The problem is schools don't teach talent. They teach you how to learn in the worst, least efficient possible way. The key is learning how to learn and that's not something that schools teach you.

When you left there, what did you end up doing when you graduated?

I was torn between two different companies, a bigger, more established company in Chicago and then this tiny little game startup in Texas. I went with the Texas company, which was a disaster. The Chicago company ended up being called Bungie. They did Halo in basically all of the major video games in the past couple of decades.

I picked the road less traveled, but the advantage of it is I was put in way over my head. I was given responsibilities far beyond what I was qualified for, but they were incredibly educational. That company did fail utterly, like every other company I've been with in my career prior to Expensify. In the process of its failure, it was a very good lesson for me.

What was the lesson? Do you think some of the lessons of being with a startup helped you at Expensify?

All the companies that I was with before failed utterly, but not even for creative reasons. They failed doing the same stuff that people knew was bad while it was happening. It's common to be in a company and be like, “I got to do this thing. It's not going to work, but what can you do? You do it. It didn't work. I told you.” Who won? What was that even about? My career was largely about seeing how not to do it, which is pretty instructive. There are a lot of lessons along the way for me with the game company.

I was a very good programmer. I would go in, have an idea and be like, “I can build that.” I would stamp all night. I had a sleeping bag under my desk that I used a lot. In the morning, I'd show it off and I'd be like, “Check it out.” They're like, “That's cool, but what about this?” I'm like, “Great idea.” I throw it all out and rewrite it all night. I was very good in that way. There was this other programmer, probably not even as good a programmer as me, would go and ask everyone. He'd be like, “What should we do?”

I'd be like, “Do this. “ He'd write that down. He'd walk to the next person, “What do you need?” “Write that down. Go around everyone. Write a document.” He's like, “I wrote this document. Does this accurately describe what you need?” Go around, then he would write it once. It would come out, and it'd be perfect. He did not have a sleeping bag under his desk. I'm like, “I'm doing this wrong. “

My method is clearly a bad method. That's where I concluded that C++ might be a great programming language, but English is even better. The ability to communicate with others about the requirements of what you're doing is the most important thing. I wasn't prioritizing it at all. When I left that company, I decided to get a job as a technical writer, which is a very weird career path. I dropped engineering. I've been in programming for 21 years at that point or for most of my life. I applied for a technical writing job.

Technical writing is interesting. There's no technology or whatsoever for the role. It's basically an English major. It would apply for this. As a result, I was going through these jobs. They're like, “You were overqualified for this job.” I'm like, “That's fine. I'm here to write user manuals.” I took this job learning to write engineering specifications on one side and user manuals on the other.

I realized if you do both of those, you bookend the entire project. You write the user manual in such a fashion that there's only one way to build it, and then people build it that way without even telling them how to build it because you made it obvious that that's how it needed to be built. A big lesson coming out of it was the importance of good communication.

Going back to this point about the imagination gap. It's hard to build the right thing if people can't agree on what it is. It’s not like people even know from the start. It's not like someone can tell you to build X because they don't have X in their mind as to what makes sense. You have to go back and forth, iterate, collaborate and all this. That's where I learned the importance of collaborating in a written form because writing is tangible evidence of thought. You can sit and talk all day with people, walk out, and say, “We're aligned, but no one agrees on anything.” You have to write it down before anyone knows what they're agreeing upon.

Also, agreement. That happens all the time as we think communication happens. It's easier to respond in writing versus having to face someone and say, “I don't truly understand.”

What's nice about writing is it is synchronous. Expensify has employees all around the world. The sun never sets in the Expensify empire. There are always some conversations happening. It's always a cool conversation on something important. If you collaborate in real-time, then it means you can only collaborate with people in your time zone.

If you collaborate through writing, documentation, asynchronous chat and so forth, you can engage in a truly global conversation. It's a very different style because you have to write it down, which means you have to think about what you're going to say, recognizing that if someone's going to read it twelve hours from now, it has to stand on its own. Everyone has to be a good communicator in writing because being a good communicator orally only gets you so far.

That expands in the social media of why communities can be built globally because that's interesting. I've never thought about it that way. Where was the leap to start Expensify? How did that happen?

I went to a few different game industry or companies. It was a kid company or something. I never even figured out what it was. It didn't make any sense at all. I did technical writing for one hour in this company. I'm like, “This Is the dumbest technology ever. It doesn't matter. I'm here to write user manuals. I'm not assessing. This company's going to fail for this reason,” then later it failed for that reason. I went through a couple of companies like that. It does another challenging lesson. I realized that being right also doesn't matter if you're not convincing.

I remember I had this CTO. He was a nemesis. He was wrong 100% of the time on every major decision in ways that were completely obvious to me. I called and it didn't matter because everyone paid attention to him. No one paid attention to me. Company failed. I was like, “This guy is good at running things to the ground and walking away Scott-free.” It was never his fault to others. I'm like, “That was clearly going to happen.” There are a lot of important lessons along the way.

I joined a small company called Red Swoosh. I did peer-to-peer content distribution, which is like BitTorrent but for legitimate content. It’s a smaller user base because you're not dealing with piracy but it's more profitable because you're not getting sued to oblivion, either. We acquired a very small company, six people or something like that. I had some money in my pocket, not a ton, but more than I've had. I lived in the Tenderloin, San Francisco. When I walked to work, I'd walk by the same people on the street every single day.

I'm thinking like, “I can't solve hunger globally or even in the city, but I have the resources to ensure that the people I see every day in the street can get a hot meal. That's within my power. It's inconvenient to try to support people on a daily basis. You could try to bring them into a McDonald's, which is very confusing and awkward. I give out gift cards or gift certificates. It's a $10 gift card or a $7 value meal. It’s not very efficient. What if I took this gift card and I had no money on it? I had a stack in my pocket. I could hand them out such that in the millisecond, when the card was swiped, I could load the exact amount of money onto that card since it'd be used for that meal. I could limit it to only work at restaurants that don't serve alcohol and only once a day for up to $10 a day. I could build something like that, a private food stamps card.”

I went to the banks with this idea and they're like, “What? No, what are you talking about? You're going to give out money? Where's the business in that? It was KYC, money laundering and PCI. Do any of these acronyms mean? This is so much work. What are you talking about? It's too weird and risky.” It was the most boring application of these cards I can come up with. I’m like, “Expense reports.”

How I got into it was I took that same exact technology. I went back to those banks and figured out all that. It's called Expensify, the corporate card for the masses. You take this card and business owners can give these cards up to their employees. Employees can use them to spend up to a certain amount of money or frequency per day at certain merchant types, and then all the purchases are routed back to the business owner so they can keep all the miles. It’s the same exact technology they wanted basically for my food stamps card, except presented in a business context. Everyone is like, “That sounds safe and boring. I hate my extension reports.”

In the process of trying to make this food stamps card, I had to invent the story of Expensify because it needed to sound credible to like all these banking partners. They'd be like, "Tell me about this expense reporting company.” I'm like, “It does all the stuff you'd expect it would do.” They're like, “Do you reimburse the receipts? I never heard those letters before, but we do that.” The iPhone comes out, and they're like, “Do you support the iPhone?” I'm like, “Absolutely. Mind you, I didn't have an iPhone. The iPhone didn't even have an app store when it launched.”

They're like, “What does your iPhone app do?” I'm like, “Everything you'd think it would do, which is,” and they're like, “Does it scan receipts?” I'm like, “Yes. Obviously, it scans receipts.” Even though, at the time, the iPhone’s camera was bad. If you took a picture receipt, you couldn't even read it. It's blurry and terrible. I made up. I kept saying yes to everything.

“Does it connect to QuickBooks?” “Absolutely.” I never use QuickBooks. I don't know anything about it. I said yes to everything. In the end, I had a pretty good pitch for this fictional company and then one day, the economy collapsed. I lost all my savings. Now I need to do something. They're like, “How about I build this company that everyone thinks is pretty cool?” The next day, the iPhone came out with an app Store and they got an autofocus camera. Now you could take cameras.

You have crystal clear receipt images. I was the only company out there pitching receipt scanning for a mobile platform that didn't have an app store and a phone that didn't take pictures. Suddenly, they got both. We became the very first expense-reporting mobile app. We were the very first to do any integrated receipt scanning and credit card import. We stumbled into the entire thing.

Were you still able to fulfill what you wanted to do for the homeless?

Eventually, we came back. Every time you swipe the card, we get a little bit of interchange. We take a bit of that. It goes to a non-profit we created called Expensify.org. It's done a bunch of different campaigns all over the place. Some are on hunger. It's a SNAP campaign in the sense that if you have a food stamps card and you have an ETF card or a SNAP benefit card, whatever you want to call it, it'll show that on the receipt when you make a purchase with it. It was when COVID happened. We said, “Scan your receipt for your bag of groceries. If it's bought with a SNAP card, we'll pay you back so you can go buy another one.”

We did basically food assistance to thousands of families throughout the pandemic. We're coming out with a new campaign that's focused on teachers because it's extremely common for teachers to pay out of pocket to help a student's need. It's common. There's already an IRS deduction specifically for teachers to pay out of pocket to help kids. We're going to be basically saying, “Scan your receipt, get your principal to approve it and then we will pay you back half.” It is doubling the money for teachers who are already heroes out there, basically taking care of kids. Expensify.org has a bunch of different campaigns. It's been going on for years. It's growing.

It's important to understand the bigger purpose behind the companies. I love that story. Going back to getting this started. You're a one-man show and a great programmer starting a business. What was that like? Because that takes you into a whole another side of you that you probably haven't explored. You're going to not only have to please when you eventually have investors but also people who work for you.

It's pretty interesting. When I started programming, it was this weird offshoot of math. I was always told, “You're like a math geek.” That's how I was categorized by everyone. I never imagined myself starting a business. I was never told I could. I never thought I could. Everyone's like, “Business is different. That's like sales, marketing and finance. Do you know what that word means?” I'm like, “I don't.” I assumed it was hard. I assumed it was beyond my skills. I'm like, “I'll stay in my lane.”

Having gone through enough failed businesses, I'm like, “If this crap can do it, I think I can too.” I didn't even plan on starting a business or Expensify. I stumbled into it. I had to because I got fired. I was doing it on the side, like nights and weekends thing. I lost my job. When the economy collapsed, all my savings were wiped out. It was out of necessity.

Was it 2008?

It’s something like that. It was pretty daunting. I'd learned a lot along the way. One important lesson I learned was that you should never share an idea before it's ready. My instincts for a long time, whenever I had an idea, I was always an idea person. I always wanted like, “I could build this.” All my friends were always like, “Lame. It's been tried, but it didn't work. Here's why it's going to fail.” I'm trying to help you out. It’s demoralized. I realized eventually, “Why am I even talking to these people? I've thought a ton about this. I share this idea and then in two seconds, why do I think they're going to have better ideas?” It took me years to come up with, “That doesn't make any sense.”

When I started to Expensify, I didn't tell anyone for one year. I've been working on it full-time for one year. The only person who knew was my girlfriend. The very first person outside of that that I told was the person who became my co-founder. We didn't tell anyone for another year until we launched a functioning product at a conference called TechCrunch50.

He's a programmer. He is an unusual guy and a former professional hockey player in Poland. I remember when I interviewed him for my previous company when I was making the pitch for Expensify, he's like, “I don't know. I could do Expensify or I'm thinking about buying a liquor store.” He went through like, “A liquor store shelf-stable product, very reliable clientele and all this stuff.” I'm like, “That's the balance. He was the cheapest guy I had ever met. He was also an incredible programmer and a great guy.” I was basically like, “I'm competing with a liquor store, but that liquor store sounds like a pretty good business.” He did. He joined here.

Before you move on, I want to hold on to this concept of negativity because it is a mindset that our brains naturally go to. It's very hard when you're a visionary. You're thinking of these ideas that the normal human experience is to go back and think about failures. Those failures get in your way of trying new things or people don't want to fail again, look or feel bad. They'll get in their way. We'll have this talk to stop putting ourselves out there again. What do you think influenced you or was within you to stay positive? You have in your story a lot of negative experiences that have happened in your career. How did that still give you hope when you have people telling you no, but in your Head

Two different things. One thing that comes to mind on the concept of dealing with rejection and failure, and I think a challenge is that success and failure look exactly the same right up to the very end. It's basically like until you're a clear success, you're a presumed failure. It's a real challenging thing to accept. What I learned is I have a lot of control over how I define success. I trace it back to, oddly enough, on my very first day of college. I met this girl. We dated for three years. We broke up the summer before senior year.

I had an internship at Intel. I was 21. I was going out to California. I had money for the first time when I was single. I remember walking around Downtown Folsom, California. I'm like, “I'm going to ask someone out, but girls are scary. I don't want to be turned down. That sucks.” I realized like, “I don't have any control over that. What they say is up to them. The only thing I can control is asking them out.” I'm going to change my mindset here and basically define it as success. In my mind, it is asking them out and whatever happens after that is gravy. I had this epiphany. I looked up and standing in front of me was this super hot skater chick way out of my league, someone I would've never asked out before.

I said, “Want to get a bottle of wine?” She's like, “Okay.” I'm like, “It's that easy? This whole time, I thought it was this hard.” I realized that moment that you have much control over how you frame success and it requires no one's permission. You just do it. You don't even have to tell anyone. You have to believe it. That always carried through with me.

When it came to starting a startup, the most important thing for me wasn't how many customers I had. It wasn't any of that stuff. It was basically like, “Was I still trying? Had I given up yet?”My measure of success is, “Am I still at it?” The way I measured that was I tracked my hours. This is for accountants. Is this very common for programmers? Not really, because I wasn't building anyone.

There's no reason to track my hours. I said, “I want to live a good life, but I also want to get crap done. I think I'm going to work 50 solid hours a week. Some people work more or less. Fifty is a good number. If I can maintain 50 task-focused hours per week, I'm going to feel good about whatever comes out.” I'm only going to put down an hour if I believe I worked that out. It's really simple. Every day, I have a spreadsheet with two columns. 1) Date. 2) “How many hours did you try your best to work this day?” No one looks at it. It's just for you. There's no reason to lie. The only right answer is, “Do you believe that number?”

You're like, “I was distracted at that hour.” “How distracted? 50% distracted. Cool. Cut it in half, then put it down. It doesn't matter.” When you work for yourself, it's paralyzing because you can go anywhere and do anything. Imagine you're in a desert at high noon. All you see are sand dunes in every direction all around you. It's like, “Which way you want to go?” It's like, “I have no idea. They all look fine.” If you change that exercise such that you can see footsteps coming all the way over the horizon, standing to the right where you walk and like, “I've been walking this direction. I guess I'm going to keep going in that direction. By adding an analysis of your own history, make a decision that was impossible. It makes it trivial.”

For me, it was about, “I want to measure my footsteps. Am I moving somewhere and doing something? I don't even know where I'm going, but as long as I'm moving, I'm going to be happy with it.” That was my attitude throughout this entire thing. I'm like, “I'm going to do this food stamps card. That doesn't work. I'm going to do this fake expense boarding company. That didn't work and I'm going to do a real expense boarding company.” I was never committed too much to the outcome. I was committed to the journey itself. I was trying to please myself. Luckily, I was in the programming field and able to make it all work, but for years, I had nothing to show for it except for a spreadsheet full of numbers.

People definitely have this mindset of like, “Am I contributing? Is my work meaningful to me?” They don't assess. There might be things within your day that were more meaningful to you than you thought if you notice them. We don't necessarily take that beat or pause in our day to notice. It's coming at us all day. That makes us be more aware of our choices.

When it comes to hiring, as we talk about these qualities, one I talk about is talent. The ability to learn without being taught and teach what you know. The second is what we call ambition. Having an actual goal for your life and some evidence that you've worked towards it. If you ask anyone, “Do you want to do something amazing with your life?” Everyone's going to be like, “I do.” You ask them, “What specific amazing thing do you want to do with your life?” They'll be like, “I have no idea. I've literally never even thought of it.”

Ambition is about taking the time to visualize your life. One of the helpful parts is that if you can see the footsteps that got you where you are, you can forward the project where you're going. You are like, “I'm walking in this direction. I've been going in this direction. Do I like where that goes?” Ambition is about trying to think about, ‘Where am I going? Do I want to go there? If not, I'm going to start making adjustments today to shift that path. Maybe it's a slow shift, but I need to take it somewhere else if I want to get someplace else.’” Ambition is about paying attention, taking your own future seriously and taking ownership over that future.

Zach was on from your company. He brought up this question you asked him during his interview and couldn't answer it. That's important that sometimes you can't answer it. I remember in my career, I was very driven toward becoming a partner in a CPA firm. I didn't know why, but that was type A personality. You want to achieve that. At a point, I was at a company and was good friends with my manager. I would realize that I would get these reviews, and 99% of the reviews would be great and 1% would be feedback that I didn't like, then I'd be all bent out of shape over that 1%.

They'd be giving me what I asked for. She stood back one time and was like, “What would make you happy?” It is like this question you're asking. There is a difference between career goals and knowing what would make you happy because sometimes you're doing things you don't even realize are not making you happy. I realized at that moment I could not answer her question, which was weird for me because I am ambitious, but I didn't know what that looked like.

Zach said the same thing. When you asked him that question, he didn't know what that was. As he's played around on the side with this DJ, this hobby has become more and more of a love and if you get into his story with this hockey playing, we drew on all of that. it drew into the skill he has of, “Practicing until you're achieving this dream.” It's like what you said. You have to be open to the possibility of what's ahead. As long as you're open to achievement, sometimes you don't know that answer right away.

Having a diversity of these goals is important. We like to say at Expensify, “We want to accomplish three things. We want to live rich, have fun and save the world.” I love the bombastic phrasing of all of those. We are like, “Let's make sure that every average boring day is awesome. You wake up in a comfortable bed with one million thread count sheets. You are with someone you love. You have a great breakfast. You go to work. You're inspired and challenged. You're working with people you enjoy, but you come home and have time and resources to spend with the people you love doing the project inside and  every boring average day is awesome.”

That's why we call it living rich. Second is having fun, which is not like Xbox fun, but bucket list fun. Ideally, at any point in time, you should always be like, “That thing we did is once in a lifetime.” That was amazing. That thing we're about to do is also going to be amazing once in a lifetime. You should always be between two bucket list entries. That's why I think it is having fun. If you're doing both of those, if you're like, “Every day is awesome,” but you're making rapid progress through your bucket list of doing cool stuff all the time, then I think you get to the mindset to think like, “My life is very full, but how do I make it better?” That's where I think giving back starts to become a real priority.

The best most people can even think about is like, “I try not to make it worse. I feel bad that I exist, but I do. I'm going to try to minimize my impact and I'm going to call that a day. That's the best I could do.” Some people are like, “I'm going to do my part. I'm going to recycle. Even though basically all evidence shows recycling is bad for the environment in many obvious ways, or there's a bunch of this virtue signaling that we do because it's like, ‘I know it doesn't matter, but it makes me look good.’”

If you want to make a difference, it's hard. It requires sustained effort, creativity, resources, and time. The only way you'll get into a mindset that you're going to apply that level of focus is if your life is awesome. If you're already having super fun, then you'll start to think about like, “What would it take to save the world? What sacrifices do I need to make in the long run? How can I maintain that over the long haul with the right people?” Expensify is all about trying to find that collection of people, get them into that mind space where they're willing to put the effort into saving the world, and then equip them with the resources to do so.

What do you do when things aren't going well in your life, uncontrollables happen and every day is not going to be your best day?

That's why you have to put on your own mask before helping others. Fundamentally, it’s like Maslow's Hierarchy. I don't think that you can realistically get into a save-the-world mindset if you're struggling at home. First is taking care of yourself, your family and your local community. You work up towards it. There's escapism to international news. We will obsess about what's happening on the other side of the planet and then ignore the problems on our doorstep. It's like, “I'm engaged. I'm a global citizen. I care about this issue over there. That makes me a good person.” It excuses not caring about the person. It's like it's easier to care about something you have no influence over because no one expects you to do anything. They care about something in front of you because then you feel obligated to act.

As far as you as a leader and being able to come up with all these concepts and ways of running your culture because you definitely run a very alternative culture that isn't necessarily something that if you are taking investment on as a tech company that I'm sure you've had to fight through a lot of the things that you do to justify it and make sure that they are willing to invest money for you to do those things with your people like having the month where you all are working in another country. You do a lot of extreme things. How did you get to that point of people on the way that have helped influence that mindset or belief in how you run a company?

First, that assumes that we're asking investors to fund this stuff. That's not going to work. That's why I'd be like, “We got profitable super early.” We're not funded by investors. We're funded by customers. Customers don't care what we do as long as we give them a good product. We prove ourselves through the product that we deliver, not through some philosophy. Fundamentally, it's about build. It sounds basic. That's why I come back to the question, “How do you run a business? Most of us don't do the dumb stuff. Don't do anything you don't think is going to work,” which sounds obvious, but almost everyone is doing stuff on a daily basis that they think is dumb and they keep doing it anyway.

It's like, “Don't do the dumb stuff.” One of the basics is to build a good product. 2) Have a sizable market. 3) Sell it at a fair price or get close to your customers and make sure they like you. Things like this, it's very basic, but we take those basics quite seriously. We have to have a functioning business and it has to be a good, sustainable growing business for us to do all this other stuff. If your business is suffering, you got to basically get back to the core.

You may have to dial back some of the fun stuff for a while and make sure that you're taking care of the actual foundation of it all. It ebbs and flows. It’s not having too tight a grip on things and recognizing that it's about the journey. We don't know what's going to happen tomorrow, but you got to enjoy along the way. Take the time, especially when you can take the time, and then double down at the times that you can't. It's very dynamic and making sure people are on board for a bumpy journey.

That's part of the interviewing process. Being brutally honest about this might be different than what you have experienced before.

We found that Expensify is great for a certain type of person and it sucks for everyone else. I talked about talent and ambition. The third and the most challenging is humility, a genuine appreciation for the ideas of others. Humility is the toughest one to interview. Talent is easy. You do testing and you can figure out basically what they know. Ambition is challenging, but we have ways to figure out basically, like, “What is your actual goal in life?”

Humility is the hardest because anyone can basically keep their shit together for an interview for a month, a year or a couple of years. Eventually, the real you comes out. If someone has an epic problem or flames out in the company, it's not because of talent, it's not because of a lack of mission generally. It's usually because they reveal over time. It's like, “I never agreed with that thing. I didn't say anything, but now I'm finally comfortable to say it.” It's like, “You should have said it from the start.”

Talent, ambition and humility. If you have those three, you are going to succeed in life. Nothing will stop you. If you don't have those three, you're going to struggle for a variety of reasons. We're only looking for people to have those three conditions and then we stand back and say, “You're going to be a superstar. We're here to help you on your journey. We'll all try to align our journeys together.” Expensify is the overlap of whatever everyone wants to do in their lives, then we were like, “I want to do this. I want to go to Vancouver. I want to go to Portland. I want to go to Seattle. There are different destinations, but they're all North.”

They can all basically take the same path for as long as that path aligns. It turns out that it doesn't matter what you want to do. Odds are, it overlaps 90% with what other people want to do. That's why we don't have any bosses. No one reports to anyone because we're trying to get an environment where everyone feels like they're working for themselves, pursuing their own dreams and ambitions alongside others that are voluntary.

I can keep talking to you. We've got to take some of this and wrap it up. There are many great stories here. Is there anything that we didn't cover you want to make sure people walk away from this conversation with?

It's about mindset and basically trying to live a good life. It's on you to figure out what that good life is. No one asks you that. How much time did you spend yesterday thinking about your long-term journey? Probably nothing. How much time today? Probably also nothing. Tomorrow's probably going to be the same. Most people go through their entire lives and never stop to think, “What am I trying to do with this?” Imagine you were reading a book about your life, “Would you read that book? Is that an interesting book?”

People have interesting lives. Anyone can do it. I'm sure there are incredibly interesting lives out there by people who are starting from a way worse place than you are. If they can do it, you can probably do it, too. The big difference is they started. They tried. They decided to do something exciting with their lives and then they started deciding what that is and doing it. I think you can do it too, but it's on you to figure that out.

This has been an amazing conversation, as usual. Thank you so much for sharing your stories with our listeners. I'm sure there are going to be many things that people take away from this.

Thanks much for asking. It's been a real pleasure.

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Now for my Mindful Moments with my conversation with David. It was fascinating to know how David thinks and how he has evolved over his career and growing up. We talked about the fact that he started computer programming at six years old. He got his first computer from his father and because of that, he started working on programming very early. He started trying to figure out video games and 3D graphics and wanted to combine video games with this experience of 3D and wanted to create adventures and experiences for people that were a part of these video games.

One of the interesting things that came from that discussion was that through all of this programming that David was doing and all of the fascination he had in creation, he didn't want to play his own games. Over time, he started realizing that there was something bigger that he wanted to do with all of this if he wasn't willing to play his own games. There was a great lesson that he said in this.

“It doesn't matter how good your code is if no one cares about it and there are no customers.” One of those things is making sure you know who your target market is and understanding who are the people that you are serving with whatever product and service that you're creating, but also, it's not just about you. It's about making sure that there is some value that you're creating by what you do that's bigger than yourself. Sometimes, we can get away from that because we're driven by our own goals that we're not thinking outside of ourselves.

One of the examples he was talking about was this company that he had joined that was motorcycle simulation games. He loved the product but understood that, once he started getting into it, there was a very small market between who would want to use that product and be interested in it. Even though you might think something is interesting, then you have to figure out if someone else cares and that you're solving a problem that someone is experiencing or a desire that somebody wants.

We also talked about the skill of computer programming. Over time, he realized that the more people went to school for computer programming, there was an inverse correlation between how useful they were as computer programmers. It's not necessarily true of any profession, but what I would say is that if you aren't passionate about what you do and willing to do it when you're not getting paid or wanting to learn more beyond the job that you're in, you become less useful. You can be technically knowledgeable, but that street smart, that real-world experience, the other things that you can offer because this skill is something that's interesting to you becomes something that makes you more valuable in the future.

It is important to think about what you do, and you want to make sure that you enjoy it outside of work and school, that you want to continue to learn and grow and that it has something in the future for you. The other thing that we talked about with this is that talent isn't just about what you learn through schooling or whether someone schools themself. It's that you have the ability to learn without being taught.

You can go find ways to learn a skill, then once you learn it, you know how to communicate it and teach it to somebody else for them to understand. We got into this discussion about communication a number of times during this conversation because there are many times that we think we've communicated that someone on the other side hasn't received the communication in the way that we intended and how there are ways to do it.

We talked about how he started expanding his skill in this is that as a programmer himself, he would go and program, then someone would review it, tell him where the flaws were and he'd go program again because he loved the program. He had watched the people around him and there was somebody else that he worked with who went and questioned people and got what was important to them before he started developing and how that saved him time in the long run.

This is important when we identify there's a gap in us. Even though David had the strength of programming, he realized he had a gap in communication. One of the things that he did was instead of taking his next role in programming, he took it as a technical writer so that he could learn how to write communication that people did build products in the right way, but he also took in all of the pain points that they were trying to solve and make sure to write it in a way that gained agreement.

When we're trying to communicate, we can leave a communication where everyone walks away and says they agree, but until we confirm that agreement in writing and doing it in writing in an effective way is important. This skill of technical writing means that you have to be able to write it so that anyone can understand it. That teaches us another way of communication when we have to write things that way.

I went through this early on in my career where I was writing QuickBooks technical manuals. I realized the detail that you had to go through in order to give instructions on how to do anything in software is very specific. You have to be very clear in your communication, or else people can't do what they intend to do.

This is an important skill to think about. If you've got a gap, how do you go learn it? How do you put yourself in something uncomfortable that might not be natural to you in order to do that? His point here, and I thought this was a good line that he said was, “Being right doesn't matter if there isn't consensus.”

A lot of times, we go into these discussions and we believe we know the right way. We might know the right way, but if we haven't gained consensus in the conversation and agreement, it doesn't matter because no one thinks we have the right way. Until we gain agreement, we can't move forward in a way that's going to solve anything for everyone.

We also talked about Expensify and how all of that got started. I thought it was such an important thing that we talked about where he talked about the whole purpose of why he started it was to help the homeless and find a way to give them money, but that they're spending it in the right way on the right things. It's not just giving them money and going toward harm.

Because of him going through the process of trying to figure out what that is, and I think this happens a lot in businesses, we have an intention of what the business is and what we want to create. We go through the process of designing it. It doesn't necessarily work out where he wasn't getting the backing to do what he wanted to do, and then we're left with to stop, review and say, “What else could this thing do? How else could I create what I have started, the knowledge and investment I've put into it? Is there another way to use it?”

That's an entrepreneurial mindset that, instead of giving up on something or walking away completely, we look at what's worked about it, what hasn't worked about it, and we can get there in another way. As you saw in the story, he has gotten there in another way. We got there by creating a product that did have use for users. We had to make sure you had the market for it using the same type of concept that he had created.

Because he has it, he is still able to fulfill his dreams of giving back and doing it in ways through that same software to make sure that he's giving back to his community in the ways that he wants to give. I think that's important that we've got a purpose beyond what we do every day, which makes it so much larger and more important. I talked to him about taking that step to start a business from being someone who's a sole or individual contributor. He talked about the fact that success and failure look the same until you get to the end of it and you've succeeded.

It's true because we make a decision to do something. We're excited to get started on that first day. We're celebrating all these great ideas, but then we have to go to the next day and bump into the issues along the way and have the problems that we have to get over, rejection that might come over time and negativity that we have to get past. We have to have the belief that the overall concept and value of what we are creating is important and it's worth it to keep working toward it, even if we have to shift things along the way.

We talked about these concepts of talent, which we talked about of being able to learn on your own and then be able to communicate it. We also talked about ambition being a very big core value that he wants to know that the people who work at Expensify have. There's a way for us to know what it is that to live a good life and trying to make sure that we know what we want in life. Even if we can't answer it, we have a belief that there's something bigger that we want to do, and we keep striving toward that until we can see it and envision it.

The third big value that he talked about, besides talent and ambition, was humility and making sure that you always have this appreciation of others. There's no ego involved. When we see the ego coming up in the workplace or in the things that we do, a lot of times, we get in the way of innovation and everybody's talent that contributes to the end game that we want. It's important that as we go through this, I think these three values of his and Expensify are important to make sure that you are focused on the right things.

His tagline of, “Living rich, having fun and saving the world while you go do it,” is to make sure that you are taking care of yourself and that you're enjoying the life that you have. You also have the bigger purpose of giving back and making a difference. We ended with understanding that mindset is something that is up to us. No one else can set our mindset for us. It's important that we make sure that we are living a good life.

No one is going to make sure we are unless we do that. To take moments to stop and think about these concepts in everything that we do and ensure that we are making a difference, even if it's in small ways with our family and in bigger ways in business, whatever it is that we can identify what those things are that we feel appreciation for each day and making sure it's not happening to us, that we're living with intention.

That is important when we talk about the energy that we create and we think about that energy for ourselves and making sure we're creating that energy for those around us. If you want to learn more about Expensify, which they have so much to offer. It's worth spending a little time of how it can save you time in your businesses and with your clients, that you can go and learn more about them and how they manage money, whether that is with corporate cars, expense tracking, next day reimbursement, invoicing, bill pay, global reimbursement, and travel booking, check out Use.Expensify.com/SpendManagement.

I hope that you enjoyed this episode and were able to take away a lot of life lessons like I was able to from David's story. Subscribe to this show so that you're notified of the next great conversation and life story we talk about, that you can learn from, and keep creating more intention and better energy for yourself and those around you.

Important Links 

• Expensify

• Spend Management

• Zach Greenwald – Past Episode

• davidmbarrett - Linkedin

• dbarrett - Twitter

About David Barrett 

David is a lifelong programmer who founded Expensify in 2008 and built it into the most popular pre accounting platform on the planet. He’s recognized as one of the world’s top network engineers, having created Expensify’s blockchain-powered database a year before Satoshi’s white paper on Bitcoin. Prior to Expensify, David led engineering for Red Swoosh — which was acquired by Akamai Technologies in 2007 — and held various roles in 3D graphics and VR development. When he’s not fearlessly leading Team Expensify from Portland, David enjoys playing Minecraft with his daughter.