Episode 133: Trust The Process To Be Ready For Your Next Opportunity With Zach Greenwald
There will always be new things to learn in life and new chances to level up yourself. In order to grab that next opportunity, you have to regularly practice, hone your craft, and improve yourself. In this episode, Amy Vetter interviews Zach Greenwald from Expensify. Together, they discuss how training to be a pro hockey player when he was younger has helped him try new things and put himself out there as an adult. Zach shares how he found a big break as a DJ, doing constant trial and error to improve his mixes. He also explains how to find comfort outside your comfort zone, the benefits of courageously showcasing yourself, and facing rejection with an open mind.
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Trust The Process To Be Ready For Your Next Opportunity With Zach Greenwald
I interview Zach Greenwald. He has been with Expensify for many years. He was hired as a member of the sales team and Zach quickly adopted a hybrid role leading partner channels with accounting firms and integrated CRMs. He's since contributed to Expensify’s nonprofit organization, worked on product development, and earned the title of Expensify’s resident DJ.
His passion for music has extended into live performances at ExpensiCon in Italy, which I got to see. He also on the side works on original music production with the dream of playing at festivals one day. During this interview we talked about his upbringing and training to be a pro hockey player during high school and going into college and how that training helped him to be able to try new things, change up life when he needed to change life, and put himself out there as an adult to take on new experiences, new hobbies, and see what life has in store for him.
There are many great lessons in this episode. I'm excited for you to read it but also share it with people who need to read it as well. 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 twelve 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.
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I am very excited to be here with Zach Greenwald from Expensify. Zach, do you want to start and give us a little background on what you do at Expensify before we get started?
I'm on our sales team and I also work in partnership development. I manage a lot of the accounting firms within our partner channel. I'm also involved in product development as well.
Thanks for joining us. Where we like to start is back where you began to get to know you and your path to where you are now. Where did you grow up? What did your parents do? Do you have brothers and sisters? We can start there.
I grew up in Maryland right outside of Washington, DC. My younger sister was exactly 2 years and 1 day apart, and we have always shared birthdays growing up, which at first was I would say a little annoying as a kid, then I have grown to love it because we get to celebrate our birthdays together. On top of that, my dad is in the construction business. He does wholesale construction supply for a lot of commercial projects up and down the East Coast. My mom is a travel agent, which has been pretty handy because we have been traveling a lot. As we get to experience and travel the world, I always lean on her for advice and it's been great throughout the years.
What were your hobbies when you grew up? What things did you enjoy doing?
Growing up, I played ice hockey my whole life. That was my passion as a kid. At first, it was something that consumed my life. On the weekends, I would travel up and down the East Coast. As I started getting into high school, I played hockey there. Right around the time I was ready to graduate high school, I had the opportunity to play what's considered juniors, which is an opportunity to put yourself to the test and see if you have what it takes to go pro. A lot of hockey players that go to college that are freshman year are 21 or 22 years old. They are a lot older than the normal freshmen and that's because they take that time off after high school to play juniors. I tried to put that to the test and I learned a lot about myself during that phase.
Next Opportunity: Put yourself out of your comfort zone and showcase yourself.
While my friends were out having fun in their freshman years of college, I was trying to pursue this dream of playing professional hockey one day. For me, going out and putting yourself on display in front of a lot of scouts and trying to make a name for yourself and build an individual brand around your name was a pretty hard thing to do. On top of that, your health is entirely dependent on how far you make it. I had opportunities to play Division 1 NCAA hockey.
There was a game up in Canada. There are a lot of scouts there. It’s almost my big shot to see if I have what it takes to make it to the next level. I got hit pretty hard. I blew out my shoulder in front of a bunch of scouts and after that, I realized that nobody wanted anything to do with me after that. A lot of those like, “Do you want offers to turn into like small D2 or D3 schools?” I will never forget this. I was sitting there talking to my dad about it and he was like, “I don't know if you are going to go pro. You need to think about going to a school that you think you will have fun at more importantly.”
I was like, “That's a pretty good idea.” A lot of the schools I was looking at were small schools up in New Hampshire. I got into Arizona State University and they were starting to build a hockey program out in the desert, which is crazy. They took me in. I started my freshman year at Arizona State. I was one of the few American players in my freshman year that was on that freshman team or recruiting class. A lot of the freshmen class were Canadian mostly because they were going through the same thing.
They were like, “I don't want to be up in the middle of Canada where it's freezing. I'd rather go down where there are palm trees and pool parties, but still be able to play competitive hockey and have fun with it.” I went to Arizona State to pursue hockey but also to enjoy myself as a collegiate student or as a collegiate athlete as well. Crazy enough, that team ended up becoming NCAA D1 a few years ago.
I was part of that initial rebuilding phase to get that team to rise to that level of stardom where they could get a bid into the NCAA. My coach back then was still the head coach and now they are playing teams like Minnesota and Boston University. They are pretty incredible. They have got this unbelievable arena that's brand new on campus. Now that I have moved to Arizona, I'm excited for the season to kick off to finally be able to watch and get reactivated.
There are many questions on this. The whole fun idea of being on a disciplined path to get to pro means it takes you away from a lot of regular times you would have had as a teenager. That's pretty similar to anyone who's been disciplined by their parents, then they go to college and have this freedom that they have never had or have to change that mindset of everything being for a purpose versus just enjoying hockey. How did you shift that mindset or did you get in trouble initially and have to change yourself around? How would this go for you?
What's interesting is you work hard towards a common goal as a kid trying to pursue this dream. Once I got to that college level, interestingly enough, I started losing interest. I was like, “I'm not going to go pro. I'm here. I get to play a game that I love but at the same time, it's consuming my weekend.” All my friends are out having fun. All my new friends are out having a good time in college and I was playing hockey. At the same time, I would be traveling almost every other weekend. I formed some amazing relationships. For me, it was while I got to play a sport that I loved and represent the school that I was at, it was an incredible experience. The injury that I endured early on in that career when I decided to make that transition to Arizona State persisted.
I blew my shoulder out in tryouts and they still took me on. In my freshman year, about twelve games in, I tore my ACL and MCL and had to get taken to the hospital mid-game. My season was over. I worked hard to get myself back to a healthy spot, and then I came back my sophomore year and hurt myself again. The same amount of games in and I got hurt twelve games. At the season's end, injury had to get surgery again.
Admittedly, and I'm pretty open about this, I was pretty depressed. I felt like I was going through depression a little bit. I had a deep look at myself and I was like, “This is impacting my ability to excel in school. It's impacting my grades. If I want to have a chance at making a better life for myself after college, I need to fix something. I need to do something different.”
After that second time, I got hurt after surgery. I looked over at my dad who's both of my parents and my sister have been incredibly supportive my entire life. I looked over at my dad and I was like, “I think I'm done. I can't do this anymore. I can't put my body through this. I need to start focusing on a different direction.” He still tells me to this day, “When you told me that, that hurt me more than it hurt you. I could tell because I have been your biggest fan since day one.” From there on out, I stopped playing and I started focusing on school and figuring out how I could graduate through college and figure out what I wanted to do with my life.
When you work hard at something thinking that you know exactly what you want to do with your life and through health and injury, it's taken from you. It takes a lot to sit back and to reevaluate maybe a different path for you to go down. I do believe everything happens for a reason. That was one of those things where I was like, “Maybe this isn't my path.” I have been ignoring the signs for many years. It's time to start accepting new signs that have been thrown at me and explore a new path. That's led me to where I am with Expensify.
You talk about yoga philosophy, mindfulness philosophy, and business, and bringing that together. One of the things that I talk about in my book about disconnecting to connect is ego and ego being the root of all unhappiness. When you talk about things depressed, a lot of that is how we see ourselves. For all those years you saw yourself as this pro hockey player. Even if you didn't achieve it, it's how you saw yourself.
We end up creating unhappiness in ourselves. We don't now know how to see ourselves because we still have that ego that's trying to protect us or however serving us personally from a mindset perspective and getting to the point of shedding that. A good example for me that is similar was when I sold my accounting practice in 2010 or 2011.
I remember thinking I should be happy. I spent two weeks depressed and I gave myself this framework of like, “Two weeks you can be sad,” but I would make myself go out, run, and try to do something each day. The important thing when we go through those changes is realizing, “That was how I defined myself.” I defined myself as the owner of this accounting practice and being a specialist or expert but even though it was a good thing to sell it, how do I define myself now instead of allowing myself to what is it that you think that you did? Did you get outside help? What did you put in place to help you on that journey?
I realized I needed to put myself out of my comfort zone. When you put yourself out of your comfort zone continuously, it starts to get a little bit more comfortable and you start to welcome new challenges that come your way. I was like, “I might as well voice myself into the business world.” I was a Film major in college. I was like, “I'm going to pick the easiest major in my class.”
Next Opportunity: When you put yourself out of your comfort zone continuously, it starts to get a little bit more comfortable. You start to welcome new challenges that come your way.
I was studying the history of cartoons, movie production and things like that didn't prepare me for the business world. I will never forget this. My best friend's mom who is a second mother to me was working at a digital marketing company at the time and she was like, “I can get you an internship and you can get into digital marketing. Give that a try. See if that's something that you want to do.”
I was like, “If it's something that can help me change the path that I'm on and I will forever be grateful for her for that. If that's something that I can maybe shift my path with a little bit.” In my junior year of college, I took on an internship with a digital marketing company in downtown Phoenix. I forced myself into the business world even though my prior jobs were working security at a bar on our college street. Before that, I worked at a Deli in my hometown in Maryland.
This was my first real exposure to the business world and having a cubicle and things like that don't exist nowadays at Expensify, but things that prepared me for this. I welcomed that new opportunity and I was nervous going into it, but I learned not just about being in the business world, but a lot about myself that even if it's scary at first, jumping in headfirst and learning as you go is the best way to continue to level up in your life. If you don't take those chances, you will never know what you are capable of. That was something that I learned pretty quickly.
Wouldn't hockey have prepared you for that by having a strategy, a plan, and how you put that together without realizing you did?
When it comes to hockey, you deal with adversity all the time. It's whether you want to level up and play on the first line or be a starter versus being a bench player or not getting accepted to be able to play in that game because you didn't make the starting lineup. There are different levels of adversity. When you are putting yourself on display in front of a scouting camp to see if anyone likes you and if you are able to make it to that next level, it's being able to rise to the occasion where you know that this is your one shot to get to that next level. Going through that many times throughout my years playing hockey mentally prepared me to take on a new path.
Dealing with rejection too.
That was a huge part of it where when you go into any interview, you are going into it thinking like, “You might get this job.” People generally are scared of going into interviews in the business world for pure fear of rejection. It's the same reason why people get nervous before dates. Fear of rejection is something that everybody has. I was rejected in sports growing up. I learned to overcome that fear. I wouldn't say even overcome it because it's human nature, but at least push it to the side and show a version of yourself that you didn't know that you had. Sometimes throughout that journey, you surprise yourself. I have continued to surprise myself throughout the years.
You have to have confidence in yourself that you might not be right for that person, team, or even that day, but you know you will the next day. You have to be sure of your vision and what you are trying to achieve. You can get past those rejections because you know there will be a yes somewhere.
That has something to say about imposter syndrome. The difference between showing confidence because you have imposter syndrome or at least trying not to show that you are scared when you have imposter syndrome or knowing that you have imposter syndrome. I didn't go to business school. I didn't have a Business degree and now I work at a publicly traded company. Sometimes I still wonder how I even got here. I have tried to accept it. The same thing goes into this new passion project of mine, which is getting into music. I have imposter syndrome.
You were at ExpensiCon in Italy and that was my first real opportunity to play music, which is something we can get into. I have imposter syndrome in that area, but you learn to accept it and eventually, as you continue to accept that you are going through or experiencing imposter syndrome, then the imposter syndrome naturally goes away and you are like, “This is me and I'm doing this. This is great.”
Next Opportunity: When you learn to accept that you are experiencing imposter syndrome, it naturally goes away and your authentic self reveals itself.
I have to tell you a funny story about that. The whole reason we got connected was because I was talking to Lindsay about you. When my son graduated from high school, I was trying to figure out a good gift for him. He played electric guitar in high school, but when he was going to college I was like, “He'd always walk around the house beatboxing. I'm going to give him a DJ set.” He started DJing and we both have a love for EDM, finding videos on YouTube, and going to some festivals. For His 21st birthday, I got him tickets for Marshmello in Las Vegas and we went there.
What a 21st birthday present. That's incredible.
It was fun. One of the things we also did with it was he would DJ my yoga classes as he was learning so that we'd have live music. We always passed back and forth in Italy and your DJ tag sounded like it was a famous person. I'm like, “Do I not know this DJ?” When put it past David to hire someone like well named, if I tell my son that there was a DJ here that he knew and I didn't know who it was. I was searching for your name online. I was trying to figure out so I didn't screw up with my son and then I talked to Lindsay and she's like, “We gave him a chance to DJ. He works here.” I was like, “How cool is that?” That was my personal story about it. I didn't want to look crap in front of my son not knowing a DJ.
You aren't the only person who tried to Google me and see if Verisito was some famous DJ.
It was coming up like, “What’s the meaning of Verisito?” Nothing was coming up. I’m like, “I give up.”
I have got a good story on that. We can get into that whenever you are ready. That was a cool experience.
How did that even start?
First off, I'm super blessed to be in a company where the culture is not only to show up and work hard and help the company grow, but they empower you to carry out your passion. I remember my interview at Expensify. When you go through this grueling interview process the last bit of that interview is you go one-on-one with David. For me, David came into this room in San Francisco and he was like, “What do you want to do with your life?”
I was like, “I don't know. I just got hired here. I want to work here.” I didn't have an answer for that to be completely honest. Deep down he was looking for people who had big dreams and aspirations to do something much bigger than Expensify in their life. He has always expressed that he wants Expensify to be a launching pad for anybody in the company to carry out any of their dreams. It's pretty incredible.
Can you go into how did you even get to Expensify? How did you get introduced there?
When I started going down that new path in college, I got this internship in Phoenix. The guy that I was sitting next to in the cubicle next to me, David Cardoza is still at Expensify. He got a job at Expensify about one year and a half before I did. He got the job at Expensify pretty early on and then I remember about a year and a half later I got a Facebook message from him and he was like, “Expensify is hiring. Would you be open to moving to San Francisco?” I was like, “Yes.”
I was going through somewhat of a tough time in Phoenix. I wasn't enjoying my job, which ended up that internship landed to be a full-time job after college and I wasn't enjoying it. I was like, “Absolutely.” A few months after that I got flown out for an interview for Expensify. We were young at the time like maybe 50 employees. I flew out for the interview. It was intense. You are in this unbelievable office overlooking downtown San Francisco. It was my first time there. It's six hours of interviews and challenges. I got through it and got the job. I never looked back and it was honestly the best thing that could have ever happened to me.
I love this question of what you want to do with your life because you would think he is looking for something there. He's looking saying, “Let it support whatever your dreams are.” That's amazing. I was asking how you get there to what is bigger than Expensify.
David, if you are reading, I finally know what I want to do now. For the last many years, I have never known what I wanted to do outside of building a career at Expensify. I never had a passion project on the side that would get me equally excited to wake up every day to take on Expensify challenges, but to also work on a passion project until around COVID is when I started picking up DJing.
Growing up I would always listen to hip-hop and rock. I was never exposed to electronic music until I came out to Arizona State for my freshman year. I remember going to my first show and it was Tiësto in Las Vegas at the Hard Rock Hotel. I didn't know what to expect but I was with a lot of my closest friends. We were all front row. That opened my eyes to how DJs control a room and the type of music that lifts you. It was a pretty euphoric experience.
I left there obsessed. I'd go home and every day I would search online for new music. I would follow new artists and watch them progress. I have always been jealous. Even when I go to a concert or a show, I'm like, “What do I have to do to get up there?” It starts with taking that first step. I downloaded this app on my iPad. I started messing around with it and learning by trial and error. I remember during COVID I purchased a DJ controller. We couldn't even leave our condo. Me and my wife would have some fun with it. I would DJ for her and we would drink wine and try to make the most out of being on lockdown. I kept going.
I was watching tutorials on YouTube. I was upgrading my DJ gear. I continue to practice every day and I still do because it's fun and it was almost an escape for me. During COVID, when you are on lockdown, your house is your office. Our second bedroom was my office. I found that when I didn't have anything else to do, I would work. I kept working. It was Friday night, I was still working and my wife was like, “Let's hang out. Let's do something.” I'm like, “You are right.”
I was like, “I should figure out like maybe take this a bit further and start practicing more and treat this more as like a passion project,” and I did. I started taking it more seriously. I would log off at a certain hour and start playing. Once COVID restrictions lifted, we'd go out with our friends in Portland and then have an after-party at our condo and would DJ for them.
I never had a lot of confidence in myself. I have never put myself to the test. I'm playing at home. I'm having a good time. Until two of our best friends got married in Mexico and they were like, “Do you want to DJ at our welcome party?” This is my first time playing in front of people I don't know that's not just like my wife in the kitchen. I was like, “This is good for me. This is how I level up.” I put myself to the test. I put myself in an uncomfortable situation where I'm going to go out there, expose myself, see if I'm any good, and see people like it. I could suck. People might not like it. I will find out quickly if I'm any good or if this is something I should keep doing. It's like, “You have to take that leap.”
I was like, “Absolutely.” First off, I was honored to even be considered. I started taking it seriously after that. I was like, “This is a big break for me. I was going home. I was organizing my music files, I was practicing every single day trial and error learning from my mistakes,” then that boat party happened. It was a boat party in Mexico and there were 100 people on board. People were jumping up and down going crazy. It was such a rewarding experience. Going into it, my heart was racing. I was super nervous.
After that was done, it was the best feeling. I was like, “That was so much fun. I was nervous, but now I feel good and validated at the same time because people think I'm good.” I was going from imposter syndrome to, “This might be something. I don't know.” After that, I started putting out mixes. I was like, “If people are hitting me up after like, ‘Did you record that? Can I get some of your music?’ Why don't I start recording my music and putting it on SoundCloud?” That's where it all started escalating. I would start putting out new mixes and then we started planning for ExpensiCon in Italy. Have you heard of our Offshore trip that we do every year?
Yes, but the audience probably hasn't. You can explain that.
Every year Expensify spends three weeks in a different country and it's called Offshore. We do this because we are largely a remote company. All of our employees work all over the world and we communicate every day through Slack, but it's an opportunity for us to get everybody together in the same location and build those relationships. On top of that, they are some of our most productive weeks because we set goals for the company as we go into each offshore, whether it's building new features. Some of our best features were built and deployed during Offshore, which is pretty incredible. Every time we go Offshore, the last week is usually a more upscale week where we get to stay in a nice hotel and then there's a big event where we hire a local DJ.
I remember the last Offshore was in Spain and there was a DJ there. Everyone loved this guy but I was like, “I think I'm better than this guy.” Everyone was having so much fun. I was like, “I think I can do this so much better.” As we were planning ExpensiCon. They were looking at local DJs in Italy and they were sharing their price tags. I was like, “This is expensive. Why are we paying for these DJs that no one's ever heard of? They are going to put the top 40. It's going to be the same song and dance. Let me throw my hat in the ring. On top of that, I'm free. You don't have to pay me.”
They were like, “Send us some mix. We want to hear you and compare you to the other DJs that we are considering hiring for this big event.” I went home. I put together a mix. On the first try, I was like, “This is pretty good. It's different. It's a unique sound. It's not top 40 but it's fun. It's a little bit of disco, some music that people can resonate with. It's upbeat and different. Different will get people dancing.” I submitted the mix and everyone was like, “This is pretty good.” A week went by and more people started playing it. I got a message from one of our employees in London. They were like, “We are playing this mix in London. It's amazing. We love it.”
They ended up being like, “We are going to go with you to play at ExpensiCon.” I was like, “This is it.” This is leveling up and going from playing in front of 100 people who all know and are very familiar with the electronic music scene to 300-plus people who might not know what electronic dance music is, who might still know what it is, but you have to put yourself to the test.
Going into that night, my heart was beating through my chest. I was practicing every single day. I upgraded my decks at home and my gear. I was making sure that this was something that I was taking seriously. I reassured everybody who picked me, I was like, “I'm not going to let you down. This is going to be a fun night that everyone's going to remember. I'm not going to mess this up.”
Going into that night and even before that, I remember we all got to meet George Clooney who was at ExpensiCon. We had him as our keynote speaker. I was like, “You would make my entire career if you came up on the DJ booth with me.” He didn't say yes, but he didn't say no and laughed at me a little bit. Going into that night now I'm double nervous. I'm playing in front of a bunch of people I don't know. George Clooney might be there and this is a huge break for me. Who knows where we can go after this?
Going into that night, I would say everything went super well. Playing for four hours is hard. Most DJs play for 1 to 1.5 hours. I left that event, went back to my hotel room and I couldn't stop smiling. I was like, “Once again you put yourself out of your comfort zone, to the test, and showcased yourself.” It goes back to everything that I have learned growing up to showcasing yourself, you have this one shot to help you level up in your life. This was potentially an opportunity for me to level up in music and see where I can go with this passion project that I love so much.
One of the things I have learned from watching my son DJ is it seems like it's easy to mix those things. He is an engineer and I'm like, “You need an engineering mind. It's specific like mixing beats.” I have always played music as well, but to me, that seems so much work. I thought it would be more like, “I will throw this and that one in.” You have to know exactly where you are going to transition and that your transitions are right. I was like, “This is exactly to every beat you play for four hours. People don't realize the amount of effort that goes into DJing.”
There's a big learning curve. Throughout the years, even since COVID, practicing every day, trial and error, and being like, “That didn't sound right. How do I switch this up?” It led me to that moment where I could play a great set that everyone could still talk about. I still get text messages from attendees to this day.
You have said a number of times that it is what you have learned growing up. In order to perform at an elite level, you have to practice. A lot of people show up without practicing understanding what it takes to get to a certain level or they look at other people and want to get there, but not understanding the work and the alone time that you have to spend in order to get to that. I played violin and viola growing up.
People don't realize how many times you play the same measure over and over for an hour to get it right, but you are hearing the composition when you go to a symphony, not realizing all the time, each person had to take individually by themselves, work with their teachers, what wasn't working then as a group to keep drilling. You know drills as an athlete. In order to take on anything, I have always thought that helped me. People would always ask about how I started keynoting or how I got that in my life. I have always attributed to my music background because I knew how to practice, set up the experience, know what dramatics, loud, soft, fast, slow, and all of those things that you have to put into music into these other things as well.
I would say a ton of practice, I completely agree with that. I would not have performed at the same level as I did that night if I hadn't spent every day practicing for hours getting ready for that big moment. On top of that, when you are up on a stage in front of hundreds of people, that wasn't my first time. I'm not referring to the time when I got to play at our friend's wedding, but I speak at SuiteWorld every year. I go to SuiteWorld’s accounting conference because I'm one of the channel leads for NetSuite. I speak at that conference every year. Every year I go up on stage, I'm always a little nervous. I will be the first to admit that like stage fright, I have it, and other people have it.
Anytime I go up on stage at a conference in front of hundreds of people talking about accounting and walking through our platform and how we could save time in their lives, I have to practice. I practice in front of a mirror, with my wife and colleagues. I go into it and I'm still a little nervous because all eyes are on you. The experience of being able to speak publicly and work on that is something that I want to get better at public speaking in general, immensely prepared me for being on stage in front of hundreds of people in Italy.
That's where it goes. I had an experience where I was running from place to place between different conferences and trying to get everything set up and make sure it was ready. People were coming into the room before I had enough time to make sure everything was ready. I looked through things. I had to stop myself and say, “Trust the process. You have trained for this. Let this go.” You want to force more detail but your brain can only take much more in a hyper-intense situation. You have to have prepared up to that point and know even if you miss your mark 20% of the time, most people won't know that you are delivering a great experience because of the training and the practice you have done up until then.
That's a good point to bring out because of the expectation of anybody who's on stage or has to perform, they think the people who are listening to you are expecting perfection and that it's not okay to mess up, but it's okay and it happens to everybody. I follow a lot of different artists on Instagram and conveniently the week before Italy, this DJ was explaining how if you were to mess up a transition in your set, no one is going to realize that or remember it.
Next Opportunity: The audience is always expecting perfection from the person performing on stage. Nevertheless, it is okay to mess up. It happens to everybody.
They are going to remember how much fun they had. The same thing goes for public speaking in general. If you forgot to say something, people aren't going to know that. You are going to know it but you are going to have to get over it and push yourself to be better next time. That's something that I try to carry with me in any opportunity that I get.
Who are your favorite DJs?
There's a guy DJ named John Summit who I like for a few reasons. I like his music, but he was an accountant at Ernst & Young. He didn't like his day-to-day. He wasn't enjoying his job and he was DJing at small bars in Chicago and trying to make a little side money. During COVID, there was a very popular song on TikTok that he made a remix of. He made this one song and all of a sudden it gets played everywhere.
He quit his job at Ernst & Young, don't quote me on that, and started pursuing his DJ career. He started creating new music, playing in front of 50, 100, 10,000, and 50,000. He rose to this level of stardom that was fast within a 2 to 3-year span it's not just the music that I love to listen to but his path has been super admirable. It got me leaning into music production as well, which is this new avenue that I'm taking.
I’m learning new software. I watch webinars or DJs and producers put on episodes on YouTube on how to produce a lot in my free time. I'm producing now, which is exciting. I'm not great at it but it's trial and error like learning how to DJ first. Maybe by some mistake, some miracle a great song will come out of it, and who knows what will happen.
That's what my son's working on. It's like starting over again. Learning a whole new language. One of the things he's working on is that he played electric guitar when he grew up and now figuring out how to incorporate that into the music production and do some riffs. It's pretty cool, all the stuff you could create and to have YouTube at your fingertips to learn anything. You can with practice and intention because you have to make the time. I would ask you how you make the time for it with a busy job.
I wanted to get into that because my priority is Expensify and I work all day every day on Expensify. I still find time to pursue this side project. I will never forget this. Many years ago, maybe we had a company all-hands like every month. David leads our company all hands. He walked in one day and he was like, “Life goals for everybody. I want to live rich. I want us all to have fun and save the world.” We were like, “What? What does that all mean?” After the all-hands, we are like, “What is he even talking about?” He kept saying it and then he would define it.
He would continue to say it to the point where we are like, “This makes a ton of sense.” When you expand on it, he is empowering us all individually to live a life where you can live rich, have fun, and save the world. It sounds easier said than done, but the way these are defined is pretty unique. To live rich is establishing a comfortable baseline where your most average boring day is still pretty great. I'm happy with my job. I wake up every day.
We don't have positions in the company. We have different teams. If you don't like what you are doing one day you can work on something different like I worked on sales, on the partnership side, and still do both. I participated in marketing. I work on product development. I have helped out with our nonprofit and I get to wake up every day and experience new challenges. Every day is different, which allows me to wake up and get excited about the day.
It also attributes to being able to live rich where I have a job that gives me comfortable pay and still encourages me to carry out my passions in life, then there's have fun. For having fun, it doesn't mean going to a concert with friends, but it's more geared towards hard fun. It is something that puts you out of your comfort zone and makes you feel rewarded when all is said and done. Hard fun is usually done in the way it's defined. It is usually done with other people. Sometimes with people that you don't know at the start, you form these relationships at the end. Hard fun are these bucket list fun things that maybe you couldn't afford or endure or even imagine. For me, that fun moment was DJing at ExpensiCon. I felt like a professional DJ. The production was insane. There was an LED.
Next Opportunity: Hard fun puts you out of your comfort zone and makes you feel rewarded. It is usually done with people you don’t know from the start but eventually form relationships with.
The lighting and all the stuff happening behind you was cool.
That was like my moment of fame. Expensify empowered me and gave me the opportunity to carry out what felt like a pipe dream for me. It turns into a bucket list thing to be able to play in front of people like that and a bunch of people I don't know and have a stage like that. It was incredible. Live rich and have fun, that's what those two mean then save the world, which is not going out there and like being like, “I'm going to save the world.”
Sometimes it's something super ambitious that seems unachievable. People say they want to save the world all the time and they might have an idea and then they might give up. We continue to embed this into our company's philosophy that no matter what we do, we also want to save the world with what we are doing.
I don't know how I want to tie that into my side project right now of music, but what was cool is I got to participate and we did a community justice grant challenge for Expensify.org, which is our nonprofit arm. It exposed me to all of the injustices that people are out there solving in their communities. I would not have learned about this other side where there's a bunch of people out there that are trying to make a difference and there are ways that we can help. The Community Justice Grant Challenge, and to summarize what that was, for anyone who's reading who isn't familiar with that. We had anybody all over the world who had an idea for how they could save the world submit a proposal to us. We got thousands of proposals and there was a structure to it.
It's like, “What's the problem you are solving and how are you going to solve it?” We reviewed thousands of applications and interviewed thousands of these nonprofits and change-makers around the world. The way that we built our solution to save the world was anytime they spent their own money towards their nonprofit or mission, they would submit it to us and we would match it. If they had X in funds, they now have 2X in funds. As long as they work with us, we will continue to help power and encourage them to double down on their efforts.
The reason why I wanted to bring this up is while I don't know what I want to do with music and how that can save the world, maybe it's taking what I have learned throughout the years in music once I get to a good place and reteach it to others. I was exposed to how the company has used its platform to help save the world. That was an awesome experience to be a part of. Even now, we still reimburse grocery receipts for people in Snap. It's an awesome thing that we are doing that we are still doing and something that I'm still very passionate about as well.
Sometimes you don't realize the small things that you do to save the world and provide people four hours of joy and remember how to feel light and dance like you did. It's those little moments. Sometimes we think it has to be these huge things, but each person has their impact when it's intentional. Although you were also achieving your dream at the same time, you were helping others to find some joy in their day as well. You should be proud of that.
That means the world to me. Thank you.
There are many great things for people to learn from this interview, but I'd like to end with some rapid-fire questions. You pick a category, either family and friends, money, spiritual, or health.
Spiritual.
Things are actions that I don't have that I want to have with spirituality.
I feel like I have everything. I'm happy with like everything that's going on in life.
You can pick family and friends. Money or health as well.
Let's go with family and friends.
That's the one I noticed most people do. Things or actions I don't have that I want.
I grew up in Maryland. Since moving away from Maryland, I don't have those deep relationships. I'm still very close with everybody that I have grown up with. Moving away and being in a different time zone. It's not an excuse, but it did impact the level of depth in our relationships. I am trying to make a better effort and call and text more, but that's something that I wish I had.
Things or actions I do have that I want to keep with my family and friends.
I'm conscious of that. I could not be conscious of the fact that I need to continue to check in with family, and friends and then be there for them and ask them questions about their lives. It's helped me to maintain good relationships with friends across the country and even coworkers who are in a completely different time zone that I have built relationships with over the years.
Things or actions I don't have that I don't want to have.
To be honest. I spend much time on work and then on the side more time as well on my passion project I want to spend more time focusing on developing relationships and doing more fun things with my wife when it's not 110 degrees here. I'm going to go on more walks, go outside more when I'm stuck inside on my computer 24/7 taking my natural surroundings for granted and I wish I could do that more.
It's good when you can recognize that and see where you need to stop because DJing is a very individual passion.
I'm very thankful to have a wife who's supportive in both areas, but I need to focus more on her, and going out more is something that I want to build up.
As we close out, is there anything that you want to make sure people take away from this episode that we haven't talked about or you want to emphasize?
First off, I'm thankful to Expensify for giving me a platform to be able to take a passion project and continue to build on it and allow them to support me in that dream. At the same time, if there's anything that you are passionate about on the outside that's outside of your work that can help you expand on your creativity, do it. There's nothing more rewarding than being able to apply yourself creatively and something else. Taking that leap, no matter how nervous you are going into an opportunity, the reward's always worth it. That's something that I have learned over the years.
Thank you so much for sharing your story. I'm excited to share it with our readers.
Thank you for having me.
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For our mindful moments in this interview with Zach, it was inspiring to know someone's story of finding a passion and finding something that was unexpected in their life that they are finding much joy out of. We began talking about his upbringing and working to become a pro hockey player one day when he was in high school and up to college when all of that changed and he got injured during a tryout. That dream of being a pro hockey player disappeared very fast. Once this happened, and we all have these moments that we have worked hard for and you are at that critical moment and life puts a fork in the road and changes it.
It was important the things that he learned from it because he kept trying to keep that passion that he had in his life and still play hockey after he was injured and found that he kept getting injured and making that very hard decision to change his life and give up hockey. One of his takeaways from it was learning that because of hockey, he had lost down on having a lot of fun with his friends and that he was missing out on a lot of things that he wanted to be a part of. If he wasn't going to go pro, why was he giving up that time?
Many times we keep pushing against a dream, whether it's in business or us personally, and we don't weigh the pros and cons of pushing against something that's pushing back at us as hard if not harder. Going through that process of giving up something that you would work hard for is soul-crushing sometimes like we talked about. He did go through a depression at that time. Snapped himself out of it by taking a look at himself and asking himself, “What can I do differently? If what I'm doing right now is not working, what are the things that I can do differently in my life?”
One of the things that he talked about was getting out of his comfort zone. Many times he had to get out of his comfort zone in hockey in order to put himself in front of scouts, be competitive, and so forth. He knew he had the skill of getting uncomfortable, but he had to force himself to find what was going to be he's not the expert, he's not the one in the room that knows everything and he has got to learn.
He talked about how his best friend's mom got him into business, gave him an internship with very little experience, and how that helped him to be able to gain the experience to do the things that you have done. If he hadn't gotten injured, where his path would be versus now being able to explore different things about himself and finding out what he's good at?
The other thing was that he had to realize that going into something that he wasn't good at, he might deal with rejection. That was also a skill he realized from his childhood and from being in hockey, that it was something that he could overcome, that he knew the process to overcome rejection, especially when you are put in a sales, or marketing position and you have rejection happening all the time in your daily life when you are trying to put yourself out there to sell new things. Instead of taking it hard, how do you go learn from it, push it aside, and keep taking on the next thing? His next thing was starting to work at Expensify.
One of the things that changed him was a question that he got from David Barrett, who is the CEO of Expensify during his interview. The question was, “What do you want to do with your life?” Many of us think we know what that answer is, but if you sat back and wrote that question for yourself and sometimes the answer to that question changes. We feel we got what we thought we wanted to do with our life, and maybe that's not the thing that's bringing us joy like we thought it would.
To still ask that question, no matter where we are in our life is an important thing because we never want to stop striving for that next best self for that next something that's going to give us joy. He couldn't answer that question at the time, and he kept exploring that. During COVID, he got back to music. He had gotten exposed to music by seeing a DJ while he was in college.
He decided during COVID to download an app and start learning how to DJ. An important piece of this interview is that anything that we do to get out of our comfort zone and we are trying something new, we have to remember how we learn. We learn is practicing many times. It's important that if we are going to try a new skill and get better at something we have to put time aside to take it seriously and to practice because a lot of adults I have seen try new things and then they are not good at it right away. They give it up and think that they should be as good as anyone else.
I know in yoga, I say it all the time to new people to not expect. To be as good as a person that has been coming in for 5, 10, or 20 years, instead to respect the experience of people who have been putting the time to practice and keep honing their skills. Anything that we are doing, that's the learning process. That's when we get outside of our comfort zone of not being the best at something, but looking to someone else and learning from them, not being afraid to ask questions, and remembering to set that time to make sure that we are practicing.
The other thing we talked about that is important is you find ways to rehearse it in small ways. He talked about how the first time he played was just with his wife, and then he started branching it out to some friends and then he was asked to play with his friend's wedding. That was a small wedding party, and then he got his confidence there.
When he finally put himself out there to play at this event at ExpensiCon in Italy, he had the experience of performing. It wasn't the first time he had ever performed before. When we talk about anything we are going to go into new, whether it's in business or outside of business, we need to think about our rehearsal process and practice. Putting the right amount of time instead of rushing through our day. If it's important to us. It's important that we are practicing those skills each day and how we are going to go about doing that.
When you are thinking about a hobby or a new initiative in business and it's something that you have never done, and it is a new skill, also think about how are you going to learn it. How are you going to put the time aside to learn it? How are you going to practice? How are you going to rehearse that you are ready for that game day? You are ready for when it launches, it's not a surprise that you can trust the process that you have gone through that you will be a success.
How he ended it was that anything, anything that you are passionate about, go and do it. Don't make excuses for why you can't do it, but find the little ways that you can do it and take the leap to do that. I want to thank Expensify again for sponsoring this episode. Expensify is a payment super app that helps individuals and businesses simplify the way they manage money.
To learn more about Expensify and how it can help save you time to focus on what matters, check out Use.Expensify.com/SpendManagement. I hope you got so much out of this episode that you can share it with your friends and family. Reach out and let us know other topics that you want me to interview or talk about on the show. I'm always happy to hear from you.
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About Zach Greenwald
Zach has been with Expensify for over 8 years now. Hired as a member of the sales team, Zach quickly adopted a hybrid role leading partner channels with accounting firms and integrated CRMs. He's since contributed to Expensify's non-profit organization, worked on product development, and more recently, has earned the title of Expensify's resident DJ. His passion for music has extended into live performances, most recently at ExpensiCon in Italy, while working on original music production with the dream of playing at festivals one day.