The Nexus of Creativity and Entrepreneurship - Scott Scarano

Unexpected connections exist all around us; we just have to be open to them. One such connection that many listeners may find surprising is the link between music and accounting. Our guest today, Scott Scarano, has always had a passion for both these disciplines. He describes accounting as the language of business and music as the language of life. Scott is the owner of a thriving accounting firm, a podcaster, and the custodian of Accounting High, an online resource that is helping to modernize the accounting profession and make it more accessible for everyone. While many people view accountants as lacking creativity, Scott, aka The Rapping CPA, is here to insist otherwise. In today’s conversation with Scott, we delve into One CPA’s Journey: The Nexus of Creativity and Entrepreneurship. 

Our discussion includes the nature of creativity, how repetition helps us grow, and what it means to be open to recognizing new and unexpected connections. Scott talks with us about how his grandfather inspired him to pursue accounting, what it was like to build his CPA firm, and how he made the transition from being an operator in his business to a high-level visionary. We also contemplate the nature of failure before hearing the story of how Scott started writing highly detailed and entertaining rap parodies. Scott closes off today's episode with a rendition of his riveting Superapp rap, which is based on Eminem’s Superman (and written for Expensify), and shares the response he got from Expensify CEO David Barrett when he had him as a guest on his podcast.

Key Points From This Episode:

• A story from Scott illustrating the power of being open to connection.
• Scott’s lifelong dream of being an actor, rapper, entertainer, and accountant.
• The connection between performance, music, and accounting.
• Scott’s history selling drugs and what it taught him about business.
• An overview of Scott’s career as an accountant and how he grew his CPA firm.
• How to go from being an operator to a high-level visionary in your business.
• Scott’s reflections on starting a podcast and what he’s learned from it.
• The Dunning-Kruger effect and the experience of repetition, change, and growth over time.
• What Scott has learned about creativity and his own desire to form new connections.
• Why every failure is an opportunity to learn, even if it’s painful.
• How Scott realized his dream of becoming a rapper.
• What Scott learned from writing rap parody songs.
• The story of how Scott wrote an Eminem rap parody for Expensify.
• Scott’s parody version of Eminem’s Superman, Superapp!

Links Mentioned in Today’s Episode:

Scott Scarano on LinkedIn
Scott Scarano on Twitter
Accounting High
Accounting High on YouTube
Accounting High Podcast
The Dunning-Kruger effect
The Creative Act: A Way of Being
FreshBooks
Expensify
ExpensiCon
David Barrett on LinkedIn
Connection Builders
Alex Drost LinkedIn

Transcript

[INTRODUCTION]

[0:00:04.5] ANNOUNCER: Welcome to Branch Out, a connection builder’s podcast, helping middle-market professionals connect, grow and excel in their careers. Through a series of conversations with leading professionals, we share stories and insights to take your career to the next level. A successful career begins with meaningful connections.

[INTERVIEW]

[0:00:20.9] AD: Scott, welcome to the Branch Out Podcast. I am looking forward to this conversation today. So I‘m going to ask you to introduce yourself in a minute here but I wanted to share a little of my thoughts and kind of my relationship with you. We got to know each other over the last, what? A handful of months now. 

We had an introduction through a mutual connection and we’ve talked a number of times for a duration of hours and just had really good conversations, really riffing back and forth and I find you to be a very creative person, a very insightful person, and also, a very unique individual that has a lot of great insights. I don’t say that just to rub your ego, thanks for coming on the show but I’m saying that because what I’m most – 

[0:00:56.9] SS: I rub my own ego enough, we’re good.

[0:01:00.3] AD: Love it. What I’m looking forward to today is just to have kind of an open dialog about being your kind of true self but also learning how to lean into the person that you are. So with all that said Scott, why don’t you just lead us off, tell us a little about who you are and what got you to where you are today?

[0:01:15.4] SS: We got to thank Randy Crabtree for introducing us. Randy’s a – he is a big connector as well, he is a connection builder as well. Sometimes I see myself or others see me as a connection builder and I know a lot of people and I like to talk and obviously us people who have podcasts in other platforms were builders of connection.

So, I always find connections with things, with people and I always draw them from different inspirations but it’s always mid-conversation that I’ll bring something up and I’ll come out of left field and I’ll be referring to this other person or this other thing and then I’ve already connected them.

So we created this new game in the card on the way down to accounting salon last year. So if you haven’t heard of an accounting salon, it’s like the little club for accountants. You got to be invited to get in, I don’t know, that is just a sidebar. We created this game on the way down there and so you start with one song or artist and then another person in the car says, any other song or artist and I got to find the connection between the two through songs. 

Six degrees of separation or less, right? And so – and I don’t know how I got into this story but it’s finding the connections between different things and this is what I do. I go off on tangents, I talk about other things but it was a dope game and we played it again this year and it was even funner the second time around because everybody else was into it and it wasn’t about figuring it out. 

Everybody’s like, “Oh, why don’t you use this one because Jay-Z is covering Elvis here and then we can use that to connect to Taylor Swift through Ed Sheeran because Ed Sheeran has this song with this person” and then we already planned out the next five songs and then I just queue them up on the playlist, so it was fun.

[0:02:53.8] AD: And speaking in, I want to make sure we get some time to learn about you and who you are before we jump in too deep here but the idea of connections and of really recognizing that most things that occur in the world have some kind of nexus somewhere, someone brought two ideas together and when you are actively seeking to find, make, and create those connections, you tend to find yourself in a more favorable place.

You stumble on more random opportunity than if you otherwise would not, right? You can argue whether it’s random or not because it’s your actions that are creating that but oftentimes, you’re sitting there and you’re like, “Oh wow, I never realized this is a great connection, this goes together.”

[0:03:27.8] SS: If you’re paying attention.

[0:03:28.3] AD: Correct. If you’re paying attention, 100%.

[0:03:31.4] SS: If you’re not paying attention then you’re only thinking about that other thing and you don’t see what’s right in front of you, then you’re going to miss a lot of opportunities. So that also happened on the same trip, I lost my luggage. It turned into such a great trip because I lost my luggage. It was a huge opportunity, we ended up stopping in this place called Buc-ees on the way down there, and we’re all playing that game and I picked up an entire wardrobe at Buc-ees. 

I got cheesy shirts but they look cool, like, it was like, Buc-ees world tour in every Buc-ees that has opened in Texas and Alabama and it was so cool. Now, that’s the mascot at my Accounting High, Buc-ee the beaver. I mean, it’s spelled differently. I don’t want to get into any copyright issues but everything I do has copyright issues. Everything’s like borrowed from somewhere. 

So but again, like all of this stuff is just to highlight the whole importance of connections, I know that’s what the show is called and that’s why I brought that story up. I know I kind of avoided the question of talking about me and I tend to always talk about myself on my show but when I get somewhere else, I want to talk about everything else.

[0:04:26.8] AD: Well, let’s talk about you now. Let’s talk about you, who are you?

[0:04:30.2] SS: This year, I’m Scotty. I didn’t ever go by that most of my life but now, people call me that. My friends always – look, my really, really close friends used to call me that but I never turned it into my own nickname until recently I started using it as like my email for Accounting High and I sign my signature with that now, so then other people start doing it. You know, it’s not like I want you to call me this or that but yeah, that’s where I’ll start. I don’t know what else do you want to know, besides my name?

[0:04:55.0] AD: What’s your career, what do you do for a living? Tell us what you to today and how you got there.

[0:04:57.1] SS: I want to be a rapper. I want to be a rapper. I’ve always wanted to be a rapper, I’ve always wanted to be an entertainer, I’ve always wanted to be an actor ever since I was young but I also always wanted to be an accountant.

[0:05:07.5] AD: How did those two go together at all?

[0:05:08.7] SS: They start with the letter A, I don’t know, actor, accountant. I don’t know how they go together but I’m figuring that out. It’s weird because nobody sees the obvious connection between the two but you can always bridge two anything’s and see where they best fit, what’s the point of connection with the least amount of artists or turns along the way?

And I think with accounting and art or accounting and music, in a lot of ways, I drew this connection before. Accounting is the language of business and music is the language of life, for some people. For me, it is, for sure. It’s like the soundtrack and it’s an entirely different language too, reading music is different than words and reading numbers is different than words.

So that’s one way that they’re different and the same. I think music’s based on numbers too and accounting’s based on numbers. So I don't know, my grandfather was a CPA and I just always saw that as an honorable profession. He’d seem to have done pretty well for himself, you know, three kids, family, never was you know, he was always working but never worried about money. So I thought, you know, that’s probably the stable profession. 

The story that I tell a lot and learning how to tell better is when I was in college, I wasn’t – I started school for accounting and I lost my way somewhere. That’s when I wanted to be an entertainer, that’s when I wanted to rap, I always wanted to act, I have a TV show at the school but I was also selling drugs at the same time and that’s where I learned business.

And I’m not saying this because I’m proud of it but it is all in my life lessons in business was learned “on the streets.” So running a business, being profitable, I mean, I wasn’t following the rules but I still don’t follow the rules today. I don’t break all the wrong rules now. I don’t break the law anymore but I was doing that then because I was a kid. I didn’t know any better, I guess. 

[0:07:00.8] AD: But you have some hustle. You’ve got some hustle and drive, you’ve got some entrepreneurialism in you, you’re clearly willing to grind, right?

[0:07:07.9] SS: Nobody could tell anything, you know? Nobody could tell me anything. It’s always about the hustle, it still is about the hustle, it always is going to be, that’s what Jay-Z, that’s why I connect with rap so much because that’s always about the hustle. “I’m a hustler baby” you know? Like, that was my connecting people too, and being the center of the party, I always loved that.

Like, if the party revolved around the person who had the party goods and the things like that, like, that was also the way I saw it, so part of it was that, part of it was having fun. Most of it was making money, that’s why I was doing it. I was – I mean, that was the easiest way to make money of any other ways to make money and you didn’t have to work that hard. It was a lot of risks involved and I took the risk, I also paid the price. 

So I lost pretty much everything to find everything I needed at that point. I was doing too much of the drugs, I was on a bad path.

[0:07:57.0] AD: Sometimes you have to become who you’re not to see who you are, right?

[0:08:00.9] SS: There you go, I like that one. I’ll write that down. So and I don’t know if I became who I was not because I still model a lot of the same behaviors now just in different ways.

[0:08:11.4] AD: Like healthier ways.

[0:08:12.5] SS: Yeah.

[0:08:12.7] AD: In a healthier way, right?

[0:08:12.8] SS: Yeah. Definitely, in a healthier way for sure and a smarter way, I would say in some ways but I learned so much through those experiences and then I went back to school for accounting and ended up finishing in accounting, worked at a couple of CPA firms, and then grew my own firm to the point where I worked myself out of a job.

So for like, the last 15 years, I mean, this was for the 15 years that I ran the firm, you know, that’s what I cared about, it was the only thing I cared about was growing the firm. Grow-grow-grow. Not really sure if I knew why I was growing it besides, I want to make more money but got to a point where I wanted to be the one that was just running the business, right?

Like, E-myth really changed my life when I read that and then a lot of Ron Baker’s books changed my life when I was reading those, and then EOS, we started doing EOS about six years ago. We were able to effectively plan out my “exit out of operations and sales” and anything else that wasn’t the visionary seat.

[0:09:11.4] AD: I want to back up, I want two things I want to make sure we highlight for our listeners. Number one, E-Myth, it’s an excellent book, we’ll make sure it’s linked in the show notes below and then beyond that, you mentioned EOS, the entrepreneurial operating system. 

Again, we’ll make sure that that is linked and that there is a book called Traction but what really – what both of those, the curriculum to the knowledge behind both of those, really is driving towards this idea of separating the difference from being the tactical professional that works in the business, the operator, versus the owner who is stepping back and looking up from a high level and saying, “Here’s where we’re going” the visionary seat if you will, and really recognizing that many folks are finding themselves in those roles very intertwined together and are so stuck in the day-to-day of working in the business that nobody’s stepping back and looking at, “How do I work on it?”

And what you’re saying is that through that process and over a number of years of working towards it, you really worked to elevate yourself above and to kind of a more of a visionary and being able to get out of the day-to-day grind and step back and look at the organization from a visionary standpoint. Is that where we’re at?

[0:10:16.2] SS: I love that, that’s dope. I need this. You’re like the little lightbulb or the Clippie that comes in and explains halfway through so I don’t get too far off the rails, right? Like, and also –

[0:10:25.9] AD: That’s 120 podcast episodes.

[0:10:28.1] SS: Yeah, it provides context. So I don't know, because I’ve done over 200 and I still don’t do that shit. So, there you go.

[0:10:37.1] AD: You’re insane though too. You do a lot of content.

[0:10:40.0] SS: Insane is probably the right word. I’ve been insane and I’ll never be the same but that’s part of that story. So I had a lot of clarity after I got arrested and after everything that happened back then. I don’t know why I jumped all the way back to there. I think the insane comment. I think I’m now at the part where I’m running my firm. So – 

But I had a lot of clarity at the early – those early stages of where I wanted and what I wanted and I sort of like, in a way, mapped out what my life would look like, and where I am right now is exactly where I kind of thought it would be but I never saw passed that point. I never had the dreams to go back and do the things that I wanted to do that I never did but I knew that that’s not what I wanted at that point. 

I knew that wasn’t what was going to make me happy. If I pursue the entertainment stuff, it would be an endless pursuit for more. It would be an endless pursuit of like, it just would never – there was no end in sight for that because when I looked at accounting and having a family and having a stable life, that seemed very appealing to me at that stage and most, you know, early 20-year-olds aren’t rushing out and getting married and having kids but I did in my early 20s.

So my daughter’s almost 16 and you know, I’ve got two other kids too but I saw that. I saw the long view of that. I’m going to have three kids, I’m going to live in a house, I’m going to play golf, live at a country club and all those things happened and then I got to the point where I wasn’t really like in any seats at the firm. 

I was just in a visionary seat and I’ll be honest, I was just bored like it wasn’t the right time for me to go in and tinker at stuff at the firm because everybody was still trying to get stable through COVID and we had all these other stuff going on and we got turned over and they’re trying to figure shit out so it’s not like they want me to help grow things or fix anything. They just needed things continuing to stay stable.

So that’s when I started doing a podcast. I don’t really know why I did it except for the fact that I like to talk and I always have a lot to say so that was a good outlet for me. I love meeting new people and I just kept getting fueled by every conversation I had and everything like – and it was terrible in the beginning. The podcast was so bad and still think it has a long way to go but it’s a lot better now than it was. You know, we’ve gone through a rebrand already and it’s really just a podcast right now.

[SPONSOR MESSAGE]

[0:13:00.4] ANNOUNCER: This is Branch Out, a connection builder’s podcast.

[INTERVIEW CONTINUED]

[0:13:07.9] AD: Let’s talk about that. I don’t want to certainly dive into why you should podcast and get into deep podcast conversation but I want to talk about this idea of repetition and kind of continual change and evolvement and I say that from the context. I know you and I were talking about this before we hit record but I myself too, I’m coming up on nearly 125 episodes and kind of winding this down. 

I’m finding myself really doing a lot of reflection and like, “Holy cow, I come a long way, I’ve grown a lot, I’ve changed a lot, I’ve learned a lot, I’ve improved a lot. What am I now, where does this go? Where do I take it from here?” and I know you’ve had some of that similar experience. Talk me through that, what have you learned? What have you – what’s kind of the lesson and what do you see in yourself out of it? 

[0:13:43.7] SS: Yeah, good question. So I’m learning about myself more than anything else and I’m learning how to become a better listener. How to become a better, more gracious person in life through my actions and what I’m saying on there because I was editing all my own episodes too for a long time. I have an editor now but early on I was like, “Damn, I shouldn’t have said that” like if I wasn’t editing it, then I wouldn’t have ever gotten any better.

I was almost editing myself. In the prior episodes. I was editing just to make it sound better so I would be okay releasing it even though the guest was fine, you know? Sometimes I‘ve had to edit through a guest because they were unsure of themselves and I was just – I was getting anybody. I would have anybody on the show and there’s something to be said about like, I was curious about what everybody had to say.

It didn’t matter who it was, it didn’t have to be a big guest or a small guest. I’m just happy to talk to anybody and still am. You know now, I’m trying to plan them out a little bit better but before, I was just hungry to record more and more and more, it’s like getting reps. I knew I was getting better over time. You know, you don’t see it progressively day-to-day, you don’t really notice it until you can go into the weeds and just to answer your question like, that’s what learned most.

Beyond that, so many other things. So many things that I took for granted about running a practice or running a firm because that’s our center, like the podcast is for the model, like early-stage firm owner and somebody that is in that position that I was in too, and all my guests and the people that I’ve had on and continuous cohost, it’s those people that are trying to learn how to become business owners. 

You know, we know accounting, you know, it’s Accounting High. So we just need to learn all these other things that nobody ever really taught us. So that’s what it turned into, at least, that’s who the ideal like, the audiences, I know the audience now so I know who we’re speaking to. So now I’m being a little bit more thoughtful about the actions and the content that we’re producing. We’re trying to gear it toward that ideal listener, the ideal persona.

[0:15:49.2] AD: One thing you said was that in the process, while you’re going through it. It not only often time seems hard, challenging, there’s stress and angst around things, there’s a learning curve but you're also recognizing that in the moment, you’re not feeling like you’re growing. You’re not seeing the change but when you look back over a period of time, when you reflect back, you start to say, “Holy cow, like, I have had a lot of growth through that, I’ve learned a lot, I’ve gained a lot of clarity.” 

And I think that’s, you know, obviously, we’re talking about this in the podcast terms but I think it’s applicable to a lot of things in life, especially things that you do that require a series of reps, right? Where you’re doing something. Again, the first time you do a tax return, it’s a little confusing. The second time you’re, “Oh, I hope I got it right.” The third time, it’s starting to make sense. The 500th time, you’re pretty good at it. 

[0:16:35.5] SS: So there’s a curve. I use this a lot and I’ve created some little titles for each part of the curve but the curve kind of goes up and then down really low and then kind of ends up somewhere in the middle and keeps continuing to rise. So it’s that peak of mount stupid is what I call it.

Like, you keep rising, you learn and then you think you know it all, and you think, “Oh, I got this, I can handle anything that you throw at me, any kind of tax return you throw at me” and then you fuck something up really big or you do something and then you end up in the valley of despair and you're like, you know too much.

You know that you don’t know anything or everything and you’re never going to become as good as those others, other tax preparers or whatever it is but then as you keep doing it and you keep getting those reps, you start climbing upwards to till you’re at the point where, “Okay, you know how stupid you were but you also know that you know a thing or two” and I remember the point I got to that in the firm and I remember the point I got to that in the podcast.

And that’s sort of like, I call it the plateau of peace or prosperity or whatever I try to throw Ps in there. I don’t have a name for that one yet but that’s sort of like plateaus and you do have growth but it’s not as steady. It’s not as sharp and it’s also a lot more intentional and you kind of know the direction you're going and it’s not as – you’ve already been through and sometimes you go back through that peak of mount stupid again and then you go back to the valley of despair, those are the highs and lows of business owner or if anybody, of a creative for sure.

[0:18:06.8] AD: Let’s talk about creative and business though, you and I have had this conversation before.

[0:18:10.4] SS: It’s the Dean and Kruger curve, that’s what it’s called. That was the one I was describing. I don’t know how to – 

[0:18:15.0] AD: Say that one more time.

[0:18:15.7] SS: Dean and Kruger curve or D and Kruger, something Kruger.

[0:18:19.2] AD: All right, we’ll try to find a link in the show notes. We’ll make sure that gets to that. No, I’ve seen similar. I think it’s a good framework to think by and this idea of being creative, leaning into the unknown, and being an entrepreneur, right? You and I have had this discussion before. As an entrepreneur, really most knowledge workers in this that we kind of meet today but specifically if you are a service-based knowledge worker, especially if you’re leading and building a firm, you’re a creative individual. 

Whether you recognize and acknowledge or not, you are constantly creating solutions, new solutions to problems that you haven’t faced before that don’t have simple answers, right? And that’s the complexities of business and those that figure out how to manage and navigate the complex and to be the ones that do the best and the way to do that is by really taking a lot of risks and leaning into the unknown and learning and making mistakes and having to be creative.

It's a different framework to think about. How have you seen that in your own entrepreneurial journey and your own kind of career and pathway?

[0:19:16.8] SS: Shout out to our boy Rick. Rick Ruben. Creative Act. That was a book I read this year that changed my life. Man, Ruben’s already changed my life like in a way but he says basically what you were saying too. I know you read the book too, so it’s like, everybody’s a creator, everybody creates and Dave Barrett said it on his episode on our show.

He don’t like people calling themselves creatives or labeling themselves as creatives. They’re usually the least creative, because everybody is. That’s sort of the point in like, what I’m figuring out is really what you – you know, forget all the labels and everything. You know, the creative, it’s in us to create and some people thrive on that. Some people thrive on doing something new and, I think, I never really understood why I always wanted to change everything. 

At the firm or in my life or whatever, I always seeked to change this and make this better or “Let’s try this differently or let’s do this.” It’s because I wanted to always create new pathways and new connections, old ways of doing things and new ways to do things and that sort of being you know, creating. All we’re doing is bridging things in a different way, with a different combination, we’re never really creating something new. 

There’s only a certain number of things in the periodic table, right? All we’re doing is finding unique ways from our own worldview to connect things differently. So to connect the different, like, phone wires to make that – you know, how the phone switcher would do that, that’s all we’re doing. With different ideas and different things, we’re just piecing them together the way that makes sense for us so we can make sense of the world, and those people that actually do that and do that out loud, others connect with that too. 

You know, not maybe not everybody will, but there’s a lot of people that will like what you’re doing and like what you're creating.

[0:21:04.4] AD: Two thoughts I want to say that I think are important. Number one, I’m a big believer that in every awe-inspiring idea is really just a derivative of a previous thought or idea that I someone heard. 

We all pull information from somewhere, there’s always more information that we’re pulling from somewhere and ultimately framing it in a different light, bringing different context to it, creating new previously unseen connections between two, what seems like disparate thoughts. 

That idea of doing that is the kind of the creative element, the seeking out but again, recognizing that we’re pulling this from previous knowledge and then what I think is really important to recognize as an individual behind that is, the only way to say something smart often times is to say, a lot of dumb things beforehand.

I mean, I have a lot of things that I get credited for that I shouldn’t say a lot, not to pat my own head but I get people relatively frequently that will say to me, “Man, that was a really good idea, Alex.” You said that really well, you’re really thoughtful in how you explain that you did a great job articulating that and I appreciate those comments. 

But recognizing that that was not the first time that I thought that thought and likely, if someone said I said it well, it’s likely not the first time I’ve thought that thought out loud and actually verbalized it. I’ve probably said it many a times before and it probably sounded less smart the first time it came out and every time I’ve talked about it again, the thought has developed further and I have gained more clarity on my own thinking behind it and my own ability to describe something and to articulate it. 

That’s going back to podcasting, that’s really been a huge benefit for me in podcasting. It’s just simply the forum to have the conversations that I do but more importantly, it’s recognizing for yourself and I think for everyone, whether it be through your writing, through your other forms of creative expression, speaking, talking, just even general socializing.

If you're not taking ideas and thinking through them and expressing them with uncertainty, knowing, “Hey, I don’t know the answer but this is what I’m thinking” and then being willing to say, “Well, you know, maybe I was wrong, let me think that through a little bit more.” How are you ever going to develop that kind of next tier of thinking?

[0:23:16.2] SS: Yeah, well, the next tier, thinking may catch you by surprise too. A lot of times it does but then also, and I just said basically, you know, something similar on a recent episode, I think with Jason Blumer. You know, sometimes things are buried in your subconscious too and you don’t even know where you got an idea from until you see it again later. I know this happens to me a lot.

[0:23:41.9] AD: That’s why I write notes down, lots of notes.

[0:23:43.3] SS: Yeah. Notes but it’s also just like you know, people are worried that they’re going to forget an idea or like, “Oh, I had this great idea and I’ve lost it. It was gone forever.” It’s going to come back up if it was a good enough idea or it’s the right time for that idea or the right time for whatever it might be and then later, you figure out what the connection was or why it was the right time. 

Because sometimes you got to go with your instinct or sometimes you got you know, you got to just let ideas move and work their way through. That’s what Rick says a lot in the book, you know you got to make sure you’re ready for it and sometimes you're not, sometimes these ideas that derail me, I’m learning this as I go too. I get derailed by an idea and it just wasn’t the right time for it but then later, it is.

Well, I’ll derail it from other things too. So I reprioritize everything in my life because of this one rap that I’m working on or this, the tournament. Like that whole ABC Tournament, the Accountant Bracket Challenge was just a whim idea that didn’t come to fruition for another year and then it was the right time and then I had somebody to help me do it and then it came out and that totally, you know, I wouldn’t say it derailed anything because that was the one thing that worked and it wasn’t the right time for it the year prior and I let the idea just sit in the back of a notebook but it came out again when we were brainstorming in December.

So you know sometimes, you know, I get impatient with the ideas too and I want them to happen because I see what it’s going to look like and I don’t have the patience to build it out or to do it. So I know I need other people to work with me, that’s where that integrator idea comes in and I don’t know if I was at it even a certain point in the story or now we’re just kind or riffing. 

But that’s you know, everything I’ve learned along the way, I’ve learned through screwing it up first too. Like every failure is just a stepping stone too. Everything that you consider a failure in the time is hard, in the time that it happens but it always makes you better in the end and you learn from that inevitably. 

I hate the failures in the moment and I hate when things don’t work out, I’ll hitch my wagon on something. So when the tournament was first starting, it was right around the time where Expensify is giving away trips to Italy and I’m like, “I had just finished writing a rap for them” like I thought I was in really good graces with them and I was like, “Do you guys want to give away one extra trip and just link it to this tournament that we’re doing?” 

They’re already giving away a hundred of them, might as well just have one of them be for the winner of this tournament. It will give them a bunch of publicity and I thought it was the greatest idea. I thought there was no way they’re going to say no to this, they just told me I was going to Italy and I’m leaving tomorrow but this was back in January and I was like, “If you guys could be the banner on this, this tournament could be Accounting High presents brought to you by Expensify.” 

It’s like they’re sponsoring a stadium but instead, it’s the whole tournament, and all they’ve got to do is give away another trip to Italy that they’re already doing. It seems like a no-brainer, everything seems to connect. It was perfect, everything was perfect and then they were like, “No, we can’t commit to something like that. We can’t do that” this is just like they don’t really know what I was doing. 

I was trying to explain the tournament like there was the imagination guy that Dave talked about in his episode. I’m devastated, I wasn’t even going to do the tournament when they said no to that. I was like, “Oh god if they don’t see the vision of this, nobody is going to see it” and then I’m approaching other people to sponsor it because I wanted to give away a trip. It’s like, “Fuck, we can’t give away a trip to Italy, maybe we’ll do, I don’t know” and I was asking around. 

I asked our faculty, so Ron Baker suggested we give away Disney University. I was like, “I don’t know if that’s a big enough draw. Are people going to really sign up for this tournament?” and all that and I don’t know, I just thought the whole thing is going to be a failure and I was going to throw in the towel and then it was the people around me that we’re actually excited about it still. 

Even though Expensify said no about the trip giveaway, people are just excited because it was going to be fun and that’s what I thought in the beginning too, but I wanted it to be big not just fun, I wanted it to be big. So then I just threw it out there. I was like, “We’re going to give away a trip to Hawaii, we don’t need Italy. We’ll figure out how we’re going to give it away, we’re going to give away a trip to Hawaii” and that became the draw for the nomination phase and it worked out. 

The tournament went from zero to 2,000. You know, we had 2,000 people over the course of the tournament. I just released the final summary episode, a recap with the two people that made it to the championship and it was long. This tournament lasted longer than the real tournament, longer than tax season, pretty much all of tax season and that was sort of intentional too. 

So it all worked out but I could’ve just not done it and I almost was just like I was so discouraged in the moment. I was like anytime somebody says no to me, I can’t deal with that because it is a reality-shaking thing because I’ve already created the reality that they said yes and I’m already onto the next few steps along the way. I’m already creating fliers that say, “Win a trip to Italy with Expensify and Accounting High” on there, right? 

I’m already designing all that shit and once they said no, I was just like, “Is any of this fucking shit worth it?” 

[SPONSOR MESSAGE]

[0:28:47.8] ANNOUNCER: This is Branch Out, bringing you candid conversations with leading middle-market professionals. 

[INTERVIEW CONTINUED]

[0:28:55.3] AD: So what’s the lesson on there? How do you learn from it and what do you do to keep going? If someone’s listening who is an entrepreneur, who’s a creative who is trying. 

[0:29:02.2] SS: Well, you’ve got to keep going. 

[0:29:02.9] AD: There you go. 

[0:29:03.7] SS: That’s it like that’s the only thing that you learn because I didn’t quit and I felt down. I felt low for a little bit but I got distracted by something else and it wasn’t that bad. You know, it wasn’t as bad as I may be dramatically explaining but it was still like one of those experiences that like and this is still playing out like me writing the rap for them was just on a whim too and that could have been a failure. 

They could have looked at this like, “What is going on here?” and maybe I could play the rap at the end because I am going to perform it and I need to go back and listen to it. I’m going to be performing it this week but that was the whole idea. I wrote it because I was like, “They’re giving away a trip to Italy, maybe I could perform the shit in Italy, that would be so dope but it’s got to be really good” and it had to be really good. 

It was like at first, I didn’t know what rap I was going to do because I do all parodies on all the ones that I do. 

[0:29:52.4] AD: Let me stop you for a sec, I want to highlight this and make this real clear for our listeners. So you said rap a few times, let’s back up. Talk a little bit about the [inaudible 0:29:59.6]

[0:29:59.1] SS: Ooh, yeah, I didn’t get there in the story. Yeah, all right. 

[0:30:02.0] AD: Let’s dive into that and then let’s go into this hearing this rap. 

[0:30:06.2] SS: I got out of the work, I started doing a podcast and then since I started messing with microphones and I started editing sound, I was like, “Maybe I could do this rap thing now.” I’ve been always wanting to do this shit my whole life and I’ve got a pretty good idea and this was late 2020 that this idea came in my head and then early 2021, I made the proclamation that by the end of – Oh no, no, this was late 2021, early 2022 last year I had made the proclamation. 

I’m going to perform, I am going to write a rap and perform it for the end of the year, this was last year and I did that but the first rap I was going to do was like just one of those little ideas that wasn’t the right time. The idea would kept floating around and then finally January, I started writing it and it took me five or six months to finish this one rap that I was working on. 

[0:30:56.7] AD: Why did you want to do it, to begin with? What was the drive for you? 

[0:30:59.2] SS: Because I’ve always wanted to be a rapper. I love rap, that’s my heart and that’s what I’ve always thought was the one thing that I love but I can’t do. You know how everybody always says like they wish they’ve pursued their dream of becoming a pianist or you know like, “I wish I was an opera singer and I just do it in the shower now” those kind of things. I want to be able to say I gave it a shot. 

You know, I saw Lil Dicky, I saw what Dave Bird is doing and how he just made one album. Brilliant, it was so dope, and then he used that to parlay into having a TV show and now he’s got a TV show on FXX and he’s part of the industry now but he was just a marketer. He was just a dude, just a regular dude and I saw him kind of paving the way for me to be able to do something like this and then I also saw other people doing it. 

So then I see as I am paying attention, I see this guy in Austin, he calls himself The Sales Rapper, Ding Zheng on LinkedIn and then I see this rapping CPA, Drew Carrick on and I saw he did a music video, The Accountants Anthem and I’m like, “There’s a place for this.” Even though everybody is telling me nobody does this, people are doing it. This is dope, this is my world, these are my people, and so I kept working on that one rap and it was my first one and it was called Outkast ATLiens and I called it CPAliens. 

This is my school now, I am going to, you know, Jack Black do the School of Rock. This is the school of rap and I’m just learning from the best of the best. I start with Outkast and the one I’m referring to for Expensify is Eminem, I’ll get to that story too. This is story time and the Outkast one kind of just unfolded over time, I started learning different things, different techniques teaching myself rhyme schemes and patterns and the way they were bending words and what they were doing with it, and how different Andre and Big Boy were too. 

I don’t know, I don’t think this has anything to do with business but it has everything to do with business like they’re complimentary to each other. One is the visionary and one is the integrator, one is the rock and the other one is the fluid-like and the stream, one is the liquid and one is the solid and I am starting to learn so much just by doing this parody and it was really just, I kind of just told my story in there. 

That was the most natural way of doing it because that’s what all rappers do, they tell their own story and so that was the first one I did and then I’m in Mexico last year and I got a bunch of ads that had sold while I was there. Before I was there and I was like, “I wanted to do ad raps. I wanted to do raps for the ads, so people would listen to the ads on the show.” So it wasn’t just like a regular ad, I wanted it to be a catchy song. 

So Dark Horse CPAs, why not do Katy Perry’s Dark Horse? John Garret did a Katy Perry Parody, I could do one too and so – because I saw his Manager video. He’s still got it on his website and I was like, “I’m going to do a Katy Perry” so Katy Parody is what I called it, Dark Horse CPA. So I just took Juicy Jay’s verse from Dark Horse CPA and I just work out at it while I was in Mexico. 

It’s not that good but it’s pretty good for the timeframe that I was doing it and for what I was trying to do, it took their value prop and I merged it with the actual song and I had my daughter do the hook and she’s singing their value prop like it was pretty cool. 

[0:34:21.1] AD: I’m going to say and I mean this very genuinely, you do a hell of a job on these, right? I’ve heard, I don’t know, four or five of the raps that you’ve done, you’ve shared with me that I listened to and I’ve listened to them not just like listen to a minute of it but actually listen to and kind of seeing some of the creative expression you’re doing and how good of a job you do not only keeping it with the parody element of it. 

But with really communicating a funny comical but also engaging in real storyline that ties in very well to whatever the underlying audience and it really speaks to not just your creative expression but the work that you put into it, right? You’ve shown me a little bit of your workflow and your process and you’re not grabbing a handful of words and throwing them back to back and calling it done. You are studying, analyzing, and really building this out in a very thoughtful way. 

[0:35:10.0] SS: I’m trying to be a storyteller. 

[0:35:11.1] AD: Man, you do a hell of a job at it. Well, let’s talk about the Expensify one. Tell me a little bit about that process and what that is and maybe we’ll wind the show out here with getting a listen to it. 

[0:35:19.8] SS: All right, so the Expensify. So this was I think maybe the fifth one, this is my second Eminem. So I did the first Eminem for my daughter for her quinceañera. I did a Haley song for Julia, Julia’s Song, and I was talking about this right before I was going to perform my first rap, so I’m bridging all the stories together, right? Connecting them so to speak. The first rap I was going to perform and I did perform it. 

So when I said I’m going to perform a rap before the end of the year, this was in September, I was up in Toronto for Fresh Books and I performed it in front of the Fresh Pack. It was like 30 people like accountants and some Fresh Books employees on a boat and it was dope. That was my first ever performance and I remember I was telling the story, it was the story that I was telling was about Julia’s and then the person that I was telling it to, I wear my Superman chain. 

I’m not wearing it right now but I always have that and they were like, “Oh Eminem” and my favorite song by Eminem is Superman and I was like, “It’s kind of my least favorite of all of them but I like it, it’s all right” but it just kind of stuck with me like that was somebody’s favorite song of Eminem and then I’m editing this little special that we did for Expensify and I just did it for attention to try to get Dave Barrett on the show. 

So I do a series of Nicole McKenzie and we call them Mix Tips and we did all words that start with the letter P, profitability, pricing, processes, people, all of it and then we did Puglia because that is where they announced this Italy trip was going to be for ExpensiCon and it was like a terrible episode, terrible. By all means, I shouldn’t even release it and we were just talking about their trip and it wasn’t really like no value adding at all. 

Nobody really listened to it but I pushed it on Twitter and I tagged them and I said, “We want to get David Barrett on the show” and they agreed to it. This was right after I finished the Toronto thing, Fresh Books, and I’m back home and then they tweet back and they say, “DM us” and all this and they scheduled it for the next week and so David Barrett is coming on the show the next week, this was like early October and I said, “I got to do a rap for them.”

They kept calling themselves the super app in emails and other things and immediately I had this idea because when I typed it out and I saw super rap, I saw super app but I saw super rap and then I thought Superman, like that was already stuck in my head because somebody said how much they loved that song, Eminem’s Superman like I know what I can do. I can do this David Barrett in first person because he’s been known for sending long emails. 

I love his emails but he did since really polarizing emails like the Donald Trump one during the election, he sent it to all the Expensify users and everybody got this email and everybody’s talking about it, yet they still go public and everything still works out for them. They keep winning. Every time he makes these big swings and does these big things, they keep winning and I idolized that. 

I love that and that was like fuel for me. It was so inspiring to watch everything he did along the way and then I knew he was going to be on the show, so I got to do this justice and I remember I was a guest on somebody else’s show that Friday before I had him on. I think he was coming on Monday or Wednesday and I had just started roughing together this idea and the person I was talking to like the host of the other show was like, “Yeah, you don’t have to put that much effort to it, they’re going to like it” and I was like, “I know.” 

I’ve already been working on this for eight or nine hours for an entire day and it wasn’t even close to where I thought it could be and he was like, “You could just give that to him, they’re going to like that” I was like, “No, I don’t want them to like it, I want them to fucking love it” and I kept getting it there. I basically took all of his emails for the last two or three years and put them in a notion page and I just kept working at Eminem’s rhyme schemes. 

I kept finding phrases that he said that fit perfect. If it wasn’t a perfect fit then and I could do some jumping jacks with it. I could change some words but most of it was his words and this is three verses, a bridge, and a chorus, and an intro interlude all on a five-minute song and I nailed all of it except for maybe the beginning intro, which I get to rewrite because this was for his birthday, so it’s also ExpensiCon in Italy but it’s also his birthday. 

I guess I can say this now because this will already be in the past, his girlfriend reached out to me recently. I guess I jumped forward to with the story. I’m going back, let me just back up to when I was writing it and I wrote it and I spent all weekend on it and I finished it. I felt like it was done. I don’t know if you know that feeling like I could work on something forever.

[0:39:54.2] AD: You birthed it when you really know it’s ready to be birthed. 

[0:39:56.5] SS: When you know it’s ready and I knew it was ready. I had auto-tune on there, I had layers of sound, I had the right instrumental and I knew I probably couldn’t release this because it was copyright. I took the instrumental from the extended deluxe edition of the 20th anniversary of the Eminem show, ripped straight off of the deluxe album thing. So I was like, “I know I can’t use this but this is what I’m going to send to them.” 

So I just created a lyric video and sent it to them for the episode because I didn’t want the whole episode – well, at first, I wanted the episode to be about that and then I got schooled by one of my buddies and he said, “No, you can’t make the episode about a rap that you just wrote for them. Play it at the end” and he’s like, “Send it to them beforehand too” and so I sent it to them beforehand and I didn’t get a response the next day. 

But I did get a response and they said they liked it and they said, “You know, play it at the end. Dave might not stay on for the whole thing or he may leave before, he may be busy but you could play it at the end” sort of like it was a huge let down for me because I have just put so much effort into it. I thought they were going to love it and everything and then it was like they said they liked it, you know? 

I was like, “All right, all right, cool” and then when he got on, the first thing I had to talk about the rap. The first I’m meeting him and everything and we were like talking for a little bit and then I was just like, “So what do you think about the rap?” and he was like, “I fucking loved it” like that was his reaction and he was like, “Well at first, we were all a little bit like, “Uh, what is this? I don’t know” and they were kind of cringey at first. 

At first and then and you’ll hear it when I play it because, in the beginning, it’s intentionally like aggressively like you know, how Eminem’s. 

[0:41:35.5] AD: Yeah, I mean, it’s Superman’s song. For anyone who knows the song, I mean it’s – 

[0:41:39.8] SS: It’s just as irreverent as they are or just as like and so just a forewarning for any listeners but I did it intentionally because I knew that’s also the kind of thing that they would like. I could have pulled it off or not, they could have hated it and I knew I was prepared for them to either hate it or love it and so now the employees knew me. So then when I went to another trip later in the year and I started meeting some of the Expensify employees at their booth, they had heard it from their Slack, so it was all shared internally. 

So I didn’t really release it but it got like play within the company, that’s all I cared about. That’s all I wanted, I didn’t want anything out of it. I wasn’t going to like charge them for it, it’s an ad. Basically, I’m going to play an Expensify ad for you here too and this is free marketing for them because I am inspired by them. 

[0:42:24.8] AD: It’s cool. Scott, again, your creativeness behind this, the work you put into it I think it’s really cool and it is cool to see it work out and you’ve done – how many of this have you done in total not just Expensify? How many of these have you done? 

[0:42:34.1] SS: 12 now. 

[0:42:36.3] AD: 12, holy cow, okay. So here’s what I want to do for us and I want us to, in a moment here, I want you to play it. I want to wind this down and then we’ll play it so that listeners can hear it on the kind of the full version of it here on the backend. Where else can they hear? Are there any other raps out if they want to hear more, can we link to a few more of this? 

[0:42:55.4] SS: One music video on YouTube, that’s the one I’m going to recommend because I have another music video that’s in production right now and I have one that I released as like a lyric video. Otherwise, they’re buried in my show. I’ll play them here and there depending on the guest because I really do need an audience when I do this. 

Releasing something out into the wild is so hard for me because I don’t see the audience’s reaction and then I could get a negative reaction or I could get one or two people that don’t like it or that respond like it’s not even negative. I don’t even fear negative responses, I fear people not really caring at all like being indifferent to it. I want the indifferent listener to be like, “Oh, that was actually pretty good.” 

That’s what I’m going for is somebody saying, “That shit was actually pretty funny” like that’s the best compliment I can get. That’s why my new rap name is OKR. If I could be better than OKR, then I’m all right and that’s the OK rapper, right? That’s you know, we talk about OKRs because Google is a big thing and I hope I don’t get sued by Google too using that as my rap name but I don’t think so. 

[0:44:03.0] AD: I don’t think, I think. 

[0:44:04.7] SS: Yeah, I mean, my other rap name is Lil Toddler. I think you know that too and that’s like sort of a nod to Lil Wayne, Lil Baby. I’m a little older than Lil Baby, it’s also a little nod to Lil Dicky because it’s a little self-deprecating. That’s sort of the – I don’t really have a full channel yet, I probably should do Sound Cloud and start releasing all of these but I will put them together now. 

I have enough tracks for the first mix tape, the app raps, right? So OKR presents App Raps. I didn’t have this time last year, so now I can release them all at once and make sure I got all the copyright shit figured out and tighten up a little, the production. 

[0:44:37.6] AD: You’ve done a good job and make sure to share with me any of the links, we’ll make sure it’s linked in the show notes for listeners here. 

[0:44:42.8] SS: You just go into our Accounting High YouTube channel. 

[0:44:44.8] AD: Excellent, we’ll get your link in there because everyone listening like honestly, I have listened, as I said, a handful of them and you’re pretty creative in putting this together. So all of that said, in a moment here I want to jump in and play it. 

[0:44:55.3] SS: You added to making this whole thing about the raps. I want them to make it about business. I want them to talk about the business stuff and then look where we are. 

[0:45:01.2] AD: We did. No, we got them. I think we got into some good business stuff. I enjoyed the conversation. I hope listeners found it valuable and for anyone listening, how can they get in touch with you? What’s the best place to find you if they want to learn more? 

[0:45:11.6] SS: I’ve got to check my email. I don’t even think I can get direct messages on Twitter. I think you can reach out to me on LinkedIn but I don’t know. I mean, yeah, LinkedIn is kind of cool. If you want to write a little note on there, I will probably see it. That’s the one thing, one input I kind of check not frequently but yeah. Yeah, I’m very like I live in my basement unless I’m traveling.

You can definitely see me at – I’ll be at conferences here and there for sure. Hopefully one day I’ll be rapping at one of these conferences and maybe we’ll see that, maybe there’ll be a space for that at some point. There’s space for comedy at them, I think comedy raps is the next thing. 

[0:45:45.5] AD: I love it. With that said, let’s jump into the Expensify rap here and again, what’s the official title? 

[0:45:50.3] SS: Super rap. Super App, they can check out Accounting High too, that’s on the podcast platforms. So this is Superapp.

[MUSIC]

[0:46:00.8] SUPER 

“Yeah, Expensify baby. Yeah.

Talk to me.

You want me to tell you something? 

Uh-huh.

I know what you want to hear

Our team’s extremely happy, I think that you are too. 

I think I love you, baby

And love by clients too, just snap a picture girl, come on let’s save the world

All the receipts you capture, world’s oyster, you’re the pearl

Even accountants happy, complete with payroll too

I call you Superapp, you’ve come to the rescue

We’ll be around forever, come on, let’s save the world

Ooh boy, you drive me crazy

Sit at my long-ass table

They call me CSO, post IPO, with the jingle now it’s simple now 

One single app, it’s universal, wow user experience we’re doubling down

Relationship and to end encrypt, maybe it’s irreverent 

Superbowl ad was the shit, Donald Trump can suck a dick

Straight from the cloud to outer space, expense report that’s self-replace

Household names we’re not the same, tiny joke startup into first place

Receipts do scan, we buy pad 

You want tips, concierge just ask 

Did you miss Expensify.cash, high margin, and enterprise-class 

We set out to grow without, sale reps it’s that word of mouth

Payroll now we fully sourced out, democracy under fire, we show out

Same low price, why it’s so nice

Bitch, Expensify has changed my life

Blind PC cash, trade for dry ice foregoing Nazi, I fly through twice

But I do one thing though, competitors come, they go

First age through fourth and fifth age, spend management 2.0

Maybe it’s ‘cause we’re viral, we thought clients we grow

We’ll surpass your forecast 2 Chainz at fucking Superbowl

It’s the age of the Superapp, age of the Superapp, age of the Superapp, age of the Superapp

The age of the Superapp, age of the Superapp, age of the Superapp, the Superapp, the Superapp 

Don’t get me wrong, we have different goals

Wearing lines between work and home

Yeah, they suck, we’d start up, where were you are, you’re in control

In the end, we’re too disciplined, we’ll be around forever I’m convinced

Support all SMBs in existence, one app all free paid subscription

You know you want that, so easy to buy not for control or collect for file

You’ll enjoy full Expensify, all plans included six-week free try

Guess it sounds too good to be true, bow we generate W2s

Consolidate all your different tools, one super app made just for you

But I do know one thing though competitors come, they go

First age through fourth and fifth age, spend management 2.0

Maybe it’s ‘cause we’re viral, we thought clients we grow

We’ll surpass your forecast 2 Chainz at fucking Superbowl

Our team’s extremely happy, I think that you are too. 

I think I love you, baby

And loved by clients too, just snap a picture girl, come on let’s save the world

All the receipts you capture, world’s oyster, you’re the pearl

Even accountants happy, complete with payroll too

I call you Superapp, you’ve come to the rescue

We’ll be around forever, come on, let’s save the world

Ooh boy, you drive me crazy

Sit at my long-ass table

First age you say pencil and pape then the cloud lasted a decade

Part three mobile app scan, we’ll receipt

Fourth age was neo-cart companies 

Oh yeah, venture clever way, failed attempt to explore interest rates

That brings us to the fifth age, free accounting, here’s my candid take

First off, what makes us special? Went public multinational

How did we stretch our cash flow? That’s just our business model

Something we really value, we built it from the bottom

Good lord, whoa there, we don’t rely on its DR models

Might say econo-classed, lived rich and fun we have

Think back when I would grab food stamps in my back pants 

Commenced up and expense, dispense, expressed how blessed I am

True to the core convinced will save the world and that’s the plan

But I do know one thing though competitors come, they go

First age through fourth and fifth age, spend management 2.0

Maybe it’s ‘cause we’re viral, we thought clients we grow

We’ll surpass your forecast 2 Chainz at fucking Superbowl

It’s the age of the Superapp, age of the Superapp, age of the Superapp, age of the Superapp

The age of the Superapp, age of the Superapp, age of the Superapp, the Superapp, the Superapp

It’s the age of the Superapp, age of the Superapp, age of the Superapp, age of the Superapp

The age of the Superapp, age of the Superapp, age of the Superapp, the Superapp, the Superapp

[INTERVIEW CONTINUED]

[0:50:41.7] AD: And what I love about that is for anyone listening that has listened to Superman and I grew up I feel like listening to Superman and a multitude of his songs but Superman is definitely one I listen to a lot, you nailed it. You nailed the parody element of it. It was very applicable to Expensify, I love it. 

So with that said Scott, we’re bumping up to our hour. I appreciate you coming on, I appreciate you sharing that and seriously man, hats off to you and all the work you’re doing, all the energy you’re putting into it because it shows and you certainly are very a creative individual but has done excellent work around these, so thank you again for taking the time to talk.

[0:51:18.2] SS: Thank you for having me on Alex, thanks. 

[0:51:20.3] AD: All right, we’ll talk soon. 

[END OF INTERVIEW]

[0:51:23.5] ANNOUNCER: Thank you for tuning in this week. Share this podcast with your professional network to help others connect, grow and excel. Like what you hear? Leave us a review and don’t forget to subscribe now. 

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