Simplifying Taxes for the Gig Economy: Insights from Keeper’s Paul Koullick

Jake Aaron Villarreal: Welcome to our podcast, From the Ground Up, where we interview startup founders exploring their journeys, their challenges, successes, and lessons learned. We hope you'd be inspired in discovering what it takes to build a thriving startup. I'm your host, Jake Aaron Villarreal, and excited to have with us today Paul Koullick, founder of Keeper, a San Francisco based startup that went through Y Combinator and raised $15 million in funding. Paul, welcome to the show.

Paul Koullick: Thanks Jake. Excited to be here.

Jake Aaron Villarreal: Great. Well, Keeper is a startup that's raised $15 million in funding. It's the first AI-based tax filing software to date. Keeper's helped over a million Americans uncover easy-to-overlook deductions and file their taxes. Paul, I love the product and the solution. Before we dive in a little bit on what problem you're solving, let's talk a little bit about you. Just so that people that are listening and other founders potentially just have a little bit more insight about you. Where are you currently live? And give us kind of the day in the life of what it's like to be you.

Paul Koullick: Yeah, um what it's like to be me. It's such a, you know, it seems like a simple question, and it's uh, people are so different, it's, it's everything's relative. But yeah, I'll start with a little background of myself, I think, I think it's helpful. Um so I live in San Francisco, but my background is you know, I'm Russo-Ukrainian I guess, genetically uh. But I, I grew up all over the world. I was born in Japan. I uh grew up in the Netherlands. And then my family moved to the States when I was 11. You know, so growing up we were not particularly well off. Uh I think my parents, you know, they prioritized my education in a, in a disproportionate way. They paid for a private school. Um but like a lot of immigrant, immigrant kids, you know I, I was always a bit of an outsider both culturally and financially. Um so I think that background you know taught me that I needed to work hard. It taught me that I, you know, always needed to, I felt like I always needed to pro- prove myself. That environment led me to Harvard, product management, and eventually to uh building Keeper.

Jake Aaron Villarreal: That's great. Um you mentioned Harvard.

Paul Koullick: Yeah.

Jake Aaron Villarreal: Great. Yeah, it's such a great school and you know it's funny, just the other day I was looking at like the top 10 most wealthiest people in the world and I think three out of the 10 came from Harvard, the other three came from Stanford. And you know, there's a lot to say about education and, and kind of where you go, you know. Network, build...

Paul Koullick: Probably selection bias, right? Uh, the wealth is generational. I, I don't know, I don't know how many of those folks were self-made you know.

Jake Aaron Villarreal: No, I, you know... yeah.

Paul Koullick: Thanks for saying that. I, I really don't think that's uh the institution. I think what, one thing Harvard does really well is they focus on... I mean as much flak as they get for, for doing uh you know, for letting money influence some of you know at least half of the people that they allow to attend the school. The other half they do a good job you know trying to find uh people who otherwise couldn't afford it. And I was you know really lucky to be part of that other half. So yeah.

Jake Aaron Villarreal: Well how did you go from Harvard and then getting into the startup community, the startup world? What was your path to get into really building technology?

Paul Koullick: Yeah um, it's a great question. I think that for me it always felt obvious. I, I always, I grew up believing that I wanted to be a businessman you know. Whatever that meant at the time I didn't know what that meant, but I, I felt it in my bones. And I think ultimately what it was, was a, a sense of uh you know complete and, and earnest authenticity with my work. I wanted to feel like I could put everything into my job and have, get rewarded for that. And I think initially I started off uh you know working for others and, and finding that at a certain point you know you don't get rewarded for additional input. And, and there is a limit to how far you can go there. And so I think eventually 5 years into my career I, I made the leap. And it felt very natural for me at the time.

Jake Aaron Villarreal: Are you a programmer by background?

Paul Koullick: Um you know I have a degree in computer science, but I, I wouldn't call myself a programmer. I, I'm always sort of tech-adjacent uh or, or programming-adjacent.

Jake Aaron Villarreal: Yeah. So you go through college, you get your degree. Walk me through how you started to get into building a startup. And I'll make the assumption that Keeper isn't your first startup. I could be wrong, but walk me through that.

Paul Koullick: Yeah um, Keeper was my first real startup. Uh I think that, I think that I was always... so Keeper is a, is a tax company. And you you know... I don't have any sort of relationship with taxes you would think, but taxes always attracted me. Because there's, how do I put this um... there's something about like defending the little guy when you're doing individual tax prep and that, that always spoke to me. My, you know, I, I grew up in a, my, my, my parents grew up in the Soviet Union. And so there was always this sense of, I would say a healthy distrust of authority. Uh just because you know, if you grow up in the Soviet Union, you can't, you can't pay all of your taxes. Like, you could not live, afford to eat, and pay all of your taxes. You have to pick one or the other, right? And so there was a sense of like you know, if you're smart... and there's this expression, like the only people who pay all their taxes are the ones who can't afford to, uh in the Soviet Union. And so I think obviously the United States is different and I think our laws are much more reasonable here, but to some extent the same is true. And I always felt this deep-rooted emotional you know, defiance towards that injustice.

We have a very complex tax system here in the States, and unfortunately that favors people who have the resources to navigate it, right? The people who um can hire a great accountant who can explain how you know, how what loopholes they can, they can claim and which ones they can't, and that, and that's how it works. And, and, and it's you know, it's capitalism. It just makes me frustrated. And it makes me especially frustrated when I see um demographics of, of hardworking people, people who often have multiple jobs, people who work what you might call gig jobs, um you know, under-optimizing their tax situation and, and paying thousands of dollars more than they should be. That's, that's what got me into Keeper in the first place, was this, this uh anger over how that part of the system worked. And I came to the realization that you can't solve that problem with you know online articles, you can't solve that problem with school, you can't solve that problem with anything except technology. You can't solve that problem with labor, right? It's too expensive to try to like, human services are too expensive to deploy against that problem. You have to solve it with tech. And that's what Keeper was. That's that, that's how Keeper started, was a, an attempt to solve this particular niche, this particular complexity within our tax code, which is called tax-deductible business expenses, um through technology.

Jake Aaron Villarreal: How big is that market?

Paul Koullick: You know uh you'd be surprised. There are 60 million households in the US that have some sort of 1099 contracting, gig income. Uh you know, about 5 million of those are going to be your traditional business owners, what people think about when they think you know "business income." But the rest are people making ends meet. You know, they, they're sometimes they're freelancers, but they usually have some sort of W2 on the side. Sometimes they have, they have two, three, four different jobs. Um so it's a huge market. It's a huge and overlooked market uh that you know, that, that I think in the tax world kind of gets bundled in with these traditional business owners. And, and that's part of the problem that we're solving at Keeper.

Jake Aaron Villarreal: I hear gig economy and I hear gig workers, I think Uber drivers. I think freelance designers. People that are doing a side hustle that you know add a couple extra grand a month. You know, you kind of forget about your expenses in the process when the year goes by because it's not your full-time job for the most part. Sometimes it is. Um I did a little research and just for the... how, how the finances are I guess defined as ter-, terms of gig economy, 2018 was I think roughly 205 billion in revenue generated from freelance and gig economy workers. 2023 is roughly in the 450 billion range. That's a lot of growth.

Paul Koullick: Yeah.

Jake Aaron Villarreal: A lot of people, YouTubers, online artists, creators, you know, making a real living. Your product helps them how?

Paul Koullick: Yeah, so these people as you said uh often don't realize or, or want to track what are called business tax-deductible expenses. So in short, these are people who are considered business owners by the IRS. They get taxed more than people who uh have W2 income. They actually pay an additional 15% tax that is independent of income bracket. It's horrible, but the, but the sort of silver lining is that they can, they can rightfully claim that a bunch of the things that they buy are actually business expenses. Um the tricky part is that part of the tax code is complex to navigate. You know, you could imagine that if you wanted to take advantage of it in a, in a, in a you know, in a not so honest way, you, you could, by claiming everything you buy as, is for your business. So the IRS has set up a bunch of uh little gotchas you know, little tricks. Like, "oh, you shouldn't claim over this many business meals" and "you shouldn't claim a home office that's more than you know 25% of your home overall." You know, these are audit flags that will get you in trouble.

And so those, that sort of a combination of factors, the fact that you know, these are, these are important to claim, but also they, it's a minefield, make it a uh make it an area that people tend to skip over or under-optimize. Um you know, the way to really claim this historically uh, because you're right, the, the types of 1099 income is so broad. You know, you might be a scorpion catcher in Arizona or you might be a food, food creator on YouTube. So it's, it's, it's... there's, there isn't a cookie cutter model for what you can write off. So you would have to go to a human. You would have to go to an accountant and get their seal of approval. And so historically this was very difficult to do. What we're doing is we're using uh you know intelligent software, uh AI to basically do what a human accountant would do if you walked into their office.

Uh so we start by asking you a couple of questions: "What do you do for work?" "Great, you're a scorpion catcher, you work from home, you drive to meet your clients. Makes sense." Um and then we ask you to connect your financial account. So whatever you use to make your purchases throughout the year, credit cards, bank statements. Uh and this is all, obviously we're sort of standing on the shoulders of giants with the, with the Plaids of the world, um so it's very easy to do that these days. And then we use that combination of data to uh intelligently scan through all of their expenses and tell them which of the things they bought are actually tax-deductible.

Uh and so that's a really exciting experience for a lot of people. They, you know, it's, it's this, it's our magic moment. It's this feeling of like uncovering the write-offs that you, you know, that you had no idea you could claim. It's very empowering. It's this feeling of uh you know, you're on the other side of the table now. You're, you're "the man," right? You're taking advantage of the system, you're writing off part of your rent, and you're doing it you know rightfully. You're doing it, you have every right to do that, you know. And here are the exact rules and, and why you can claim you know a desk in your bedroom even though it's not a separate room, you know. Here's the um the legal precedence that makes that okay, you know. We are... one of the things that always made that hard is it required a human's time. AI has, has infinite time, right? Or it's very, it's very cheap. And so it can take the time to explain every little thing to you and make you feel safe and help you understand the tax code in a way that was never possible before.

Jake Aaron Villarreal: I love the fact that you can do it with a phone and you can get the alerts. I mean, I didn't know much about your company. I did a little research, went to YouTube, saw some commercials, some ads. And you know, every day we're spending money as a company. And I can tell you that manually, if I'm not tracking it or at least thinking about "what did we spend last month" or looking at my credit card every month and doing an assessment of where, where spend is going... you know, if I got a text, I'm looking at this text every day. And if I respond and it's organized and you know, structured in a way that I don't have to do the work, that's a really, a no-brainer from my perspective. You mentioned AI. AI's gotten so much press in the last six months than probably has in the last 30 years.

Paul Koullick: Yeah.

Jake Aaron Villarreal: Um you started your company before ChatGPT came out or at least was publicized.

Paul Koullick: Yeah.

Jake Aaron Villarreal: Um how does, how does AI really impact your business? Is your platform completely built on AI? Is it integrated? Walk, walk me through that.

Paul Koullick: You know it's funny, even, even two years ago I would have hated to hear myself describe us as an AI company in some ways. I, I've always been, I guess, on the, on the, in the range of founders I've always been a bit allergic to the jargon side of things. You know, I, I, I, I sort of never... well it's, it's a weakness of, you know, it is what it is. I, I've never, I've always stayed away from crypto, NF-, NFTs, you know, Internet of Things, whatever. I, I sort of, I've always wanted to just build, create value, and you know, exchange that for, for revenue. That's always been the goal. So in many ways we didn't used to describe ourselves as an AI-based company. But enough has, in the world has changed, I would say over the last two years, that, that intelligence that we were doing before... which was AI, but, but sort of we would just "smart software, like do it, do what you will with it"... we now I think rightfully call it um AI. Because, because so much has advanced. I mean LLMs are so powerful. Uh the, a lot of the technology that, that used to limit our ability to do like holistic uh tax advice is now, is not quite achievable.

So, so the way you asked the question about what part of um the process is AI. So our company, I think like a lot of other companies in the space, is like 80% infrastructure and 20% magic, you know. Uh and it's only the, it's only the quote-unquote "magic" that, that AI is helpful for. Most of the work is still, "Okay, get the bank statements, identify which of these are recent transactions you know, pending versus, versus actual transactions, you know, uh clean up the merchant name, uh you know categorize it." You know, you only need AI when you have... I guess the intelligence is only as good as its inputs. And so you have to prepare the inputs for it.

And, and so there is this moment where I would say if you're trying to build with rules-based software pre-AI, it was very difficult to do that last step. The prediction step. You know, someone has common their expenses, "Was, you know, should I recommend that uh this, you know, this trip to Safeway was actually a write-off?" Well, it's really hard to know because it depends on, you know, is Safeway a gas station in the state that they live in? And if it is a gas station, do they drive for work? Would they be able to claim it? "Oh, they, they do. Okay. Have they claimed Safeway as gas before? Uh other, other people in their region, do they claim Safeway as gas?" So there's, there are so many... To try to build that as a rules-based system is, is, is an almost impossible task. But even the current state of, of uh, which is still fairly limited, of, of quote-unquote "general AI" can handle it. Uh where it could handle at the level I would say that a human accountant could, can do it. Uh which is, which is fairly high, you know. There's, there's still a limit, you, you can't, like you know, you can't know the unknowable. But you, but you can get to the level of a, you know, sort of an H&R Block accountant.

Jake Aaron Villarreal: So if you are a business owner and you've got QuickBooks for example, and you write [up] final at the end of the year, you go to your CPA, you got to provide them all the data and they're going to do your taxes. Where's, where do you inter- you know, where are you at in that spectrum?

Paul Koullick: Yeah, great question. Yeah. So I, I would say uh you know when I broke down the market for 60 million households, 5 million of which are real business owners quote-unquote right, they, they take it seriously, they do business accounting, and that's what QuickBooks is. And so there's a, it's actually a very well established and, and, and great market. There's a lot of tools available to you if you're willing to put in the work. So if you're willing to spend your Sunday night you know categorizing and you're willing to do the research to know to tell a platform like QuickBooks "this was a write-off and this was not," then um you know then, then that's great. And, and there's a lot of alternatives for you.

The part of the market that we're focused on is the, is the 55 million. It's the much, it's the much bigger and much harder segment where they don't want to do business accounting. They, they don't, you know, if you told them, "Oh, this is a business accounting tool," they would say "No, no, I don't need that." Um what they want is to get more money back on their refund right. That's, that's, that's what taxes are. Is, is once a year I get a, you know, either get some money back or I owe the government, I would like to you know reduce that or, or get more money. Like that's, that's what taxes are. And so we, so, where, where we fit in is we meet them exactly where they're at and we put write-offs in context of that greater goal. Rather than treating it separately from... you know traditionally you have like accounting, bookkeeping services and tax filing services. And they kind of, you need both, and they're separate. And so one of our big things is that we yeah, we, we, we, we sort of get rid of all that Ivory Tower mentality. You don't have to have a separate bank account. We don't expect you to pay quarterly taxes. We don't you know, we don't expect you to know what's a write-off and what's not. We meet you exactly where you're at.

Jake Aaron Villarreal: There's another company that we work with called Beacons. I'm not sure if you heard of them, Beacons AI.

Paul Koullick: Mm-hmm.

Jake Aaron Villarreal: And they actually cater to the, the gig economy online creators. They've done a tremendous job of growth and have, you know, millions of, I think they have millions of um customers, but it sounds like a, a really good collaborative opportunity potentially with them just if there's any sort of you know um introductions that make sense. I mean, I'm just thinking about you know, we're in the startup space. We work with lots of founders, lots of companies that are innovating. And there's so many that are building products that there's like affiliation relationships that probably would be very uh helpful for both parties, right? You're both solving the same problems but with different technologies.

Paul Koullick: Yeah.

Jake Aaron Villarreal: So um I always love to hear you know different areas within business world that you're solving problems that business owners go through, but they're not sure when they're going to get there, where they need products like, like yours.

Paul Koullick: Yeah.

Jake Aaron Villarreal: When you went out and started your company, you most companies' product, they might get some users, they might go through an accelerator, they raise capital. Um in the last five years a lot of companies raised a ton of money. A lot of them are out of business today. What was your strategy in raising capital and how is that ahead of the curve in today's world versus many other companies that are no longer around?

Paul Koullick: Yeah, I mean hindsight is 20/20 and it's tempting to make it sound like we were savants. Um we were not. I would say in some ways we were just scared. We were just um, you know, I think so we, we were a YC company and I think one thing YC does very well is that they instill you know, the, the right level of paranoia and fear into, into their companies. They, you know, they, one, one thing they do very well for example is they talk about how you don't have product-market fit until your customers are sending you cupcakes, right? That's like a classic line from um, from Patrick from Stripe, right? He's like, "You don't have it. Like you think you have it, you don't have it." And uh you know, unless they're not knocking down your door and you're, you, you know you're accepting cupcakes, like you're all, you're trying to like force a manifest destiny. And at some point that boulder is kind of come rolling down, back, back down the hill. And so we were very conscious of that attitude and we were quite scrappy because of it.

I think that um you know we were four people uh well beyond 2 million in ARR. Uh we, you know, we had raised $15 million, we were 2 million in ARR and we, and, and we were just four people. So I think for, in my mind it was, part of it was about um trying to have sort of a long-term perspective. Like, "My goal is not to hire a bunch of people. My goal is to build a great business. And do I need... because every time you add a person you add overhead, uh you add communication overhead, you add misalignment overhead. And like, it doesn't equal you know, plus one doesn't equal plus one on, on you know, on, on productivity. It's some, it starts to flatten out." And so uh we've always been very conscious to that.

When we did raise 15 million, it was 2021. And we, I guess again in retrospect it sounds nice, but in, in many ways we also bought into the hype. And it was, it was impossible not to. I mean, we were like, "Okay, we got to, got to hire a bunch of people you know, it's time." And so we did do that. We, we are 25 uh folks today. We just, we just so happen to be building a business that makes money. Um you know we, we, this is again probably a bit of the paranoia and fear that was instilled in us by YC and, and maybe is gener- generally what we have, is we, we never, you know, we never did the thing where it was like "oh, revenue doesn't matter," you know. It was always at the end of the day, we felt like revenue was a manifestation of value. It was a reflection of the value we deliver. And so if we don't, if customers are not paying us, then, then what we're building may not be valuable. The one way to prove that it's valuable is, is, is that they pay us. And so that was the uh yeah, that's probably the reason why we didn't hire 60 people, you know. And that was the reason why uh we are on track to be you know, 11 million, 12 million and cash flow positive by end of this tax year, is because we, maybe a combination of that paranoia and a little bit of like first principles thinking.

But I, it was not easy at the time, you know. I don't, I don't mean to make it sound like we knew what was going to happen. We had no idea. We were just, in many ways we were looking at these other companies and thinking like, "We're behind," you know. "They're, they're, they're able to... how are they able to hire 60 people so quickly?" you know? Um so I think it was... yeah, I think it was uh, I was also extremely paranoid about hiring the right people. I mean, the amount of like energy that I put into, I, I would do, especially for, for senior hires, I would do maybe eight, nine reference calls. I mean, I was like, I was like a detective. Like I would, I would identify a thing that I was a little bit worried about. Like, "Okay, this person seems really great at these things. I'm a little worried that they're going to you know... wants, they're going to... there's going to be tension around people management you know, I don't see people management in their short-term uh horizon. I'm worried that they might have an ego thing where they you know, they want to push in that direction." So I would sort of like, like a dog with a, with a scent, I would chase that trail. I would talk to all their references. I would really poke on that. I was just so worried that we would hire the wrong people, having been at other startups where I felt like sometimes one... I don't want to say bad apple, but one mis-, one, one misaligned uh hire can really hurt the culture of the business. So we, for that reason, we hired very slowly.

Jake Aaron Villarreal: Yeah, well congratulations on taking that approach. I think you know, a lot of companies are looking at that model today, and even ones that have raised a lot of money and have had to downsize, you know, they're looking at you know how they move forward. It's about you know generating revenue and profitability and not how many people you have on the books.

Paul Koullick: Yeah.

Jake Aaron Villarreal: You know, is it sustainable? So those are all great things. Hiring is a tricky, tricky problem. You got to understand what you are and what you want, and then go out in the market and hopefully you find those type of people that fit what you want them to do. The core skills you need, do they fit your culture, do they align with what you're building. What's, what's, what, what are some of the insights that you've learned? We haven't gotten it all right, hired, fired. What are some of the insights you've learned that have really helped you identify and make sure you've got the right people on, on your team?

Paul Koullick: Yeah, that's a great question. So my favorite part of an interview process is always towards the end where I you know, I very purposefully create an environment that is uh bi-directional. So what I mean by that is, is that final call is always goes... not the final, the sort of pre-offer and then post-offer experience always goes something like this: "Listen, we're in the same boat now, like you know, we're, you've really, you're incredibly impressive. You have all the opportunities in the world in front of you. Let's talk about whether you'll be happy here. Let's, let's figure out if this is the right place for you right. Like here are the things I'm worried about. What are you worried about?" And, and we sort of go through that process. It's like an anti-interview right. And I you know, you, I spend so much time with them at that point. We, we, we get breakfast, we uh you know, we go for a walk. We, we really, I, I really make it clear to them, which I think the more senior you are the more you realize this already, is that this is, this is years of your life. And you don't know us yet, you, you know, you have no idea if, if uh you know, I want this to be a success for you as much as I, I need it to be a success for us.

And that process is, I think very um, very important. A lot of people are you know, they sort of treat an interview process as like, "Well, my job is to get the offer, and then I'll think about it." And they, they, then they don't really... once they get the offer they're, they're tired, and they just kind of, they just kind of like don't do the second step of thinking about it. And I found that to be very dangerous. So I, I've always forced that to happen, you know, sort of independent of, of you know, "We're, we're sort of, we can make the offer, but we can always... there's always time to, to, to, to have another conversation, to have you meet this person, to um you know, really dig into what kind of people management opportunities there exist," like that kind of thing.

Jake Aaron Villarreal: You've been in business how many years now?

Paul Koullick: Been five years. Yeah.

Jake Aaron Villarreal: Okay. You got 25 people. Um what's the culture like today in the company? Like if you're outside looking in, you hear this story, and it sounds like a perfect fit for what you're doing and they want to be part of it. What do they experience there? And what is it like to work for you? And why is it great to work for Keeper?

Paul Koullick: Yeah. So the, those original four uh people, right, that we... for the first three years we were just four people. We were all uh... we all came from other startups, we all saw other uh versions of what it, what, what it could be like to build a small business. And I think we all, for that reason, were very intentional about the kind of environment we wanted to create. Um some of the things that, the values that, that I think are evident for anyone who joins... the kind of feedback we get you know a week after they join about things that they weren't expecting, is um just how uh I would say psychologically safe an environment we create. We work a lot on uh making sure that people have information at their disposal, that they um have a voice, that they are, you know... that we don't ambush people with uh, with sort of meeting culture.

So one of the things that we do a lot of for example is, is um... this is going to sound super boring but I love it uh very much, is, is doc culture. Where you have this uh where you have this uh kind of expectation to write down your thoughts ahead of time, share it beforehand, leave comments, and then discuss the comments in live. I think goes a long way to create that sense of psychological safety, to make people more efficient, to avoid wasting people's time in meetings. We have a very intense doc culture. Uh and that was kind of an outcome of, of having seen what happens as companies scale, you know. From, I guess I had been through all the way from Series A's through Series E's before this, and seen you know what, what things scale like at those different stages. And, and seeing you know politics do start to happen once you get to a certain point, um and seeing how to, how to make sure that you're not uh feeding that cycle.

Jake Aaron Villarreal: Yeah, that's great. I, I think you know messaging is really important. You know when companies start to grow, you know when you have hiring processes in place, and you know as the founder... as your four founders, you might have a different message of why it's great to work for your company versus the hiring manager that's interviewing maybe for the first time. And aligning that message, making sure everyone's on the same page, in sync, um can get you know, diluted pretty quick. Um what, what are the things that you do to ensure that everyone's kind of on message when it comes to, to building your team?

Paul Koullick: Yeah, that's fair. Uh it's a good question. So I work with the hiring manager to, to give them the pitch. I mean, you know, good candidates, one thing we learned about good candidates too is they don't, they need information up front. They're not going to just take a leap on some random you know... if they don't know us, then, then of course they're going to assume that we're just another you know random startup. So we, we, the first call is always "pitch." And it's an earnest pitch right? It's "Here's what we do. Here's why we do it. Here's why we uh you know, are excited about the future." And so I do coach every uh hiring manager on exactly how to do that. Sometimes they apply their own flavor, but a lot of the time it's like, you know, "My job is to do the pitch, I've had a lot of practice and, and this is a good formula for explaining what we do." So they'll just sort of adopt it. Um so that, that's the first step I would say.

Uh from there, I think it's okay for different hiring managers to have different cultures. You know, my um... sorry if the... can you hear that background noise or no?

Jake Aaron Villarreal: Yeah, no problem.

Paul Koullick: Okay. Um you know, my, my CTO for example, is a much more kind of uh buttoned up personality. You know, I'm much more like "bring your work personality to work and you know, I don't need you to be my friend" kind of uh you know persona, which I think is actually very respectful and great in that environment. And then my product lead is um, is, is, is very kind of vivacious and, and uh you know wants to put, wears his heart on his sleeve and all that. And so I think it's, I think it's good at that point to bring in your personality because ultimately a person joins for their manager. Uh so I do encourage that. And then towards the end of the process, I'm involved every time, right. Um so I, I always have that call. Uh I, I spend, sometimes it's multiple calls with every candidate. Uh because, because it's that important.

Jake Aaron Villarreal: So some companies today are focused on you know, "COVID is gone, it's time to come back in the office." You know, there's a lot of debate what's right, what's wrong. I don't know if there's an answer. What's your answer for that?

Paul Koullick: Yeah, um so we, our answer is uh we're small enough where I think you have to be in the... like you will, we, we gain a lot from, from meat space, uh from being in the office. So we do require that every new employee is in the office at least for the first year. We make certain exceptions after that point. Uh so we do have a, a few folks who are remote first, but most of the team is in San Francisco. And um you know comes in at least three days a week.

Jake Aaron Villarreal: Yeah, trade-offs both ways. And like I said there's no right or wrong answer, but I, I think that's great you know, you at some point you got to put your foot in the ground and say, "this is how we do it, you know. If you're a fit, you'll be part of how we operate."

Paul Koullick: Yeah, I think that, I think that... I'll be honest, I think it's tricky to hire um you know, I guess it is easy to hire young people that are willing to like move cities and uh you know and just come in every day. It starts to get trickier and like your pool starts to diminish quite a bit if you're looking for more senior exec types who are already living in the area and already able to commute and all these things. And so that's where the real trade-offs come into play. You know, I think, you know, as we're on our journey and, and we raise a B, you know, I think that at that point uh we'll have to think about it again. Because I think up to this point it's been very easy to be in person. But I think you know at the Series B plus stage, when you, when you you know when you continue to need additional types of leaders to join your organization, like that's where the bigger trade-offs start to come in in my mind.

Jake Aaron Villarreal: Yeah, you know funding is tricky. It's um... you've succeeded. You got the 15 million dollars. You've got you know, a large amount of ARR coming in. So financially it sounds like you're in a good position. Um I always love to ask the question: how many times do you have to pitch to actually get your A round?

Paul Koullick: Yeah, it's a good, it's a great question. So I'll start by talking about our seed round. Our seed round was so easy, it was crazy right. I was like, I was on top of the world. That was like one day after demo day. YC is an incredible kind of uh you know accelerator in both meanings of the word for that. And then the Series A was very hard. Uh I think that it was 2021, I mean it was, there was every reason in the world for it to be easy, but uh it was very difficult. And I think we did about 70 uh top of funnel conversations. Uh I think that, you know you probably hear this a lot, you know, about, about three quarters of the way through we, we were almost like "you know what, that's fine. We don't need to raise money. We can build, we can build this off of our own uh you know off our own revenue." And basically gave up. And then it wasn't until... and then at that point I think something maybe changed, something clicked. And uh you know folks started to buy in. But it wasn't easy. I think that uh you learned a lot from that hardship. I think you did, you do in many ways. The business we're building is uh... there's a, let's just say there's a graveyard of other companies that have tried to build in the, in the model that we're doing. And it took, it took work to convince those uh those people who, who are with us today that we're doing things differently and we figured it out, you know. And, and we have, you know, because you're... especially during a Series A, the "we figured it out" bit is, is a very tricky balance. Because you're not... the truth is you haven't figured it out. Like you, you figured out some of it, and you have a confidence that you have more than 10% chance of figuring it out, right? Which is like a, a little bit of a different uh, yeah. So anyway, it was hard. Uh and you learned a lot, or I learned a lot. But yeah.

Jake Aaron Villarreal: Well, congratulations. That's really great to hear. We've, we hear numbers that are pretty crazy. And I think um on the outside looking in, you would never think it would take that many presentations. We've talked to people that have you know, they put a list of 2,000 investors to target together. And you know on you know, presentation number 150 and they're still you know, in the process. And some get the funding and some don't. But I do, I do think you learn a lot. I think your story gets better. When you first started your company and the thesis that you had, has that changed? And have you had to make any major pivots between where you started and where you're at today?

Paul Koullick: Yeah, that's a great question. Let me actually double click on the comment you made previously as well. Um you know, the, the comment about "your story gets better." So I want to clarify what that means for us, because one way to interpret that line... I think it's a very wise uh sentiment... but I think one way to interpret it is like, "oh, you pitch better, you like explain it better." I think that's only a small portion of it. For us a lot of it was I became more resolute in my understanding of my business. Because I was getting pushed around so much. Because I was constantly getting "you know, what about this, what about that?" I got, finally got to a point where I was like, "You know what? You're right. I don't know the answer to this, but here's why, you know, here are the reasons not to invest, and here are the reasons, you know, here's what you need to believe in order to uh, to join us on this journey." And that sort of... that only crystallizes after a lot of pain and a lot of no's. You know, having that sort of sense of, "you know what, this isn't for everyone." Um, and so that, that part of you know, telling your story I think is, was really important for us. That, that part of the telling our story is that we're a direct to consumer business that has you know a long way to go before we get to the kind of retention that like a TurboTax has. And so sort of convincing investors that, you know... and ourselves frankly, most importantly ourselves... that we, this is how we're going to get there was a really part of that journey. Really big part of that journey.

Um with respect to whether we pivoted. Yeah, so we, we've um we've gotten a little bit broader. So we started off as just focused on gig workers. And one of the sort of realities of you know of building a business that, that uh is, wants to be cash flow positive is you have, you have to think about the uh, the relationship between your customer persona and retention. And you know, we sort of got, we, we, we had this mentality for a long time, maybe for three and a half years that you know, "if we just build the right features, you know if we just do the right kind of product changes, we can retain these gig workers forever. And they'll keep paying us $168 a year you know for the rest of their lives." And they, and eventually we got to a point where we learned that "you know what? Maybe um, maybe that's not realistic. Maybe someone who earns 30k a year shouldn't be paying 168, we just can't make that math work."

And so we got to a point about a year and a half ago where things really clicked and we realized that we just need to, we need to, we, we can continue to serve gig workers and we can offer like tiered pricing to make it affordable. But we need to also go up market. And we need to sell to the kind of customer who values their time more than their money. And uh you know, and is willing to pay uh you know, we now have a plan for 192 and another plan for 300 a year, right? And, and we, we love to sell to, to customers who were previously getting ripped off and paying $2,000 for an accountant. Because you, you would, it's unbelievable how many people there are like that who are you know, middle-class Americans. And so that, we, we sort of stepped into that segment and that, that change of segment also changed our, change of, that change of segment also changed our uh, our, our roadmap quite a bit. It made us kind of go from an app that you know, when we would market ourselves, it was essentially some version of "free money." It was like, "link your bank account, answer a couple questions, we add $1,200 to your refund" was the pitch. And then we, we had to mature. We had to serve a customer who was a little bit more you know, savvier and, and, and, and, and all that. So we, we updated our visuals and our messaging is much more holistic now. It's you know, "Intelligent, the first intelligent tax filing software." And "yes, we'll automatically identify your write-offs, but we'll also keep you safe from audits." "Well you know, we ensure all these different things. We you know have a human reviewer sign your return at the end." All those different things that attract a sort of higher um LTV customer.

Jake Aaron Villarreal: Really cool to hear that. Um as we kind of wrap up here, I have a few more questions for you. As a leader, as the one that's kind of guiding the ship. You know, it's lonely at the top sometimes. You don't always have the insights about your own employees of what's happening. And you know, how do you always keep that line of communication open? But sometimes you just need a sounding board. Sometimes you get a coach, sometimes you have just a third party you can talk to. What, what's work, what works for you? What, what's your strategy there?

Paul Koullick: It's a great question. I have, so, so absolutely it's lonely at the top uh, or maybe you know maybe not, I have a co-founder. So I think, I think that helps first of all. So you know, we share that burden you know. I, I, there is, there are no, we are fully transparent uh, and so I think that's, that was always important to me. We're 50/50, is always important to me. I, I understand that certain founders feel like you know one person is more experienced, and so it should be 70/30 or whatever or 60/40. But I always felt like this is going to be a hard path, a hard journey. And you know, let's be 50/50 to, to, to reflect that. And so I think that's a big part of it. I think that I have gone through and, and worked with coaches as well. And some have been better, better than others, but I haven't sort of found one long term. And then you know, having a life outside of work, or at least relationships outside of work, I think is also the quote-unquote "trick." So my wife is you know, I married... we got married about uh six months into the startup journey. So I locked that in and now she's uh you know she's seen it all. We, we you know she knows, she knows the struggle. So I think that's a big part of it as well.

Jake Aaron Villarreal: Really cool. I want to wrap up with the insights of the day in the life of you Paul. So give me the one-minute chronological "you wake up at this time and you do all these tasks and at the end of the day you're closing the, closing the door going to bed at this time." What's that look like for you?

Paul Koullick: Yeah um, I mean look, I've, I've never been the you know "sleep four hours maniac" type. I, I sleep a lot because I, I think that quality matters more than quantity. So I sleep... holy cow, I'm so sorry Jake.

Jake Aaron Villarreal: No problems.

Paul Koullick: Um alright, so I'm going to keep, I'm going to redo that. So, so yeah, look. I, I wake up at 7. I um, I, I have found that I have to exercise every day. I keep going through these stages where I try to convince myself that I don't have to, and then I become frustrated and sad and I realize that yes I do. So I do exercise every day. It's either swimming or running. Um at that point I, I work from you know 9 to 7 usually. Uh I think that it used to be more, I think I used to be maybe, maybe 8 to 8 uh, but I've learned how to, yeah, I've learned that there are ways that that starts to bite you that aren't healthy, that are actually worse for the business. I find that the, if I have a prolonged period of time where I'm working a lot uh you know, I get, I also get more touchy. I get more sensitive. I get more angry. And, and that causes other issues in the business. And so I, yeah, so I, I have a regimented schedule. I don't actually deviate off of that schedule. I don't work after you know, late at night. Um I sleep, I, I, that, that's, that's also working, right. I need to be fresh for the day ahead.

Um during the day I uh, one thing I found, you know we're 25 people, so it's certainly different at different stages, but one thing I found at our stage is that my, my job changes a lot every three months or every two months maybe, you know. I'll do, I'll basically deep dive on a certain part of the business. So I might you know, during a given two months increment, I might be extremely focused on product management and you know digging into those processes and fixing some of those issues. And then I might switch over to our you know our, our marketing team. Um so kind of embracing that, that my job is not you know, regular in that sense. Uh but then outside of that, I have my one-on-ones with my you know reports. Uh a big part of that is I usually do those on Fridays. We do those in person. In person I think really matters. Uh and those are really, really important. I actually prepare quite a bit for those to make sure that they're effective. What I think we, I used to do one-on-ones where it was just you know "let's catch up." Uh but I found that it's good to have that personal connection, but it's really important to, to maximize the value there, to really push on the things that need to be pushed on. Um so yeah. So that's the day in life. I come home. Uh I actually am the one who cooks dinner. My wife is uh she does other things, but I, I always cook the dinner. So I, I'll cook food, uh we'll have a sit-down dinner and uh we'll go to bed around 9:30, 10.

Jake Aaron Villarreal: That's great. I think the thing that sticks out to me of everything you just said there is the, the, the sleep and the requirement for sleep. Uh and especially when you're stressed and you're just building companies and going through your daily family life, you know, sleep can get away from you. And that's right, that's right, it changes your energy and it changes how you operate and how you think. And I think it's so undervalued in our society that... yeah I love that answer.

Paul Koullick: Productivity is not linear. I mean this is something, maybe, maybe when you're two, four people it is, but uh it's so difficult to, you can't map hours spent to output you know. So much of the time, especially when you have a larger team, your job is to make other people more productive. And figuring out how to make other people more productive is, is an art, right. It's tricky, it requires being well rested frankly. Um and, and I often lull myself, I find myself uh very comfortable being busy, right. And so I tell myself that "oh well I'll pick up an, an individual contributor task and I'll just you know slam my head against that for a while." I think there's value to it you know, setting an example. Sometimes there are tasks that, that, that are uniquely you know diff- like cross-functional that, that the CEO needs to take on. But a lot of the time it's not. It's actually not productive. You're feeling productive but you're actually, you're actually the opposite of that. You're, you know, you're kind of just pantomiming going through the motions.

Jake Aaron Villarreal: Yeah I totally agree with you. It's, it's cool to hear you say that because it's easy to feel productive. But if you're more strategic about how your time is utilized as a leader, you could do 10x you know the value of what you're doing in the company at that point in time. The fact that you said you evolve or you kind of have a new position every couple months, two or three, that to me is really insightful. Because you know you have a title and you have certain characteristics and requirements to kind of run the company, but I don't think people put too much attention to how much you have to evolve and adapt as your company's adapting.

Paul Koullick: Yeah, I think it's critically important to do that and be aware of that too. So really cool to hear you say. I spent about 4 months just being a you know, social media advertiser at one point in the business. And I, and I, I remember thinking, I was like "Okay, am I going too deep?" But as it turns out, that is a really important skillset for the business. And that experience helped me hire an incredible uh you know division owner who I would not have been able to hire had I not had a hands-on experience. So I think, I think it's, it's um, it's tempting to say "Well, I'm the CEO, I need to delegate everything." And it's a, it's a tricky balance between those two.

Jake Aaron Villarreal: Yeah, yeah. Well Paul it's been a great uh experience hearing your story and understanding your journey. It sounds like you've done a lot but there's a lot forward moving. What, what's next for your company? What do you see on the horizon as you look into the next you know 2024, 2025?

Paul Koullick: This is a very exciting year. I think the world has woken up to the power of more general intelligence. I think that the way that our product works is going to rapidly change and has already rapidly changed. And it's really exciting to be on the bleeding edge of that. I also am excited just from a financial standpoint of getting to a stronger position, right? "Let's get the 12 million in ARR. Let's get cash flow positive. Let's um you know, at that point if the you know, if we want to raise we can raise. And you know, and that's great. And we can, we don't have to be at the sort of mercy of the capital markets uh if we don't want to raise at that time." So I'm excited for all that. I think that um you know I think that those are the macro things that you think about every day as a founder. And then the little things are, are good to remind yourself of, that you know your, your childhood friend who actually downloaded your app and didn't realize it was your app and is immensely grateful for the service. Stuff like that sometimes is, is the real thing that gets you up in the morning. So yeah.

Jake Aaron Villarreal: That's great. If people want to find you or find Keeper Paul, where do they go?

Paul Koullick: Keepertax.com. You can find us on the App Store: Keeper. Um yeah, and, and you know you can reach out. I'm, I'm... we're not you know, especially if you're, if you're someone who uh we're hiring for engineers. We're hiring for really any, any smart you know, talented person looking to join a 25-person team and excited about our mission. So reach out on LinkedIn or just paul@keepertax.com.

Jake Aaron Villarreal: Cool. Paul thanks so much for joining our program today and for all the listeners that are listening, uh appreciate you and thanks for spending your time with us today. Look forward to catching up with you, in the future Paul, and with all our listeners on the next episode. Have a great...

Paul Koullick: It was really fun to be here. Connect soon. See you.

Jake Aaron Villarreal: Before we wrap up, I want to give a big shout out to all the entrepreneurs that have joined to make this podcast possible. And for all the listeners for listening, it means the world to me that you chose to spend your time with us today. I'm your host Jake Aaron Villarreal signing off for now, but can't wait to connect with you all soon on the next episode. Take care.  

This show is sponsored by Match Relevant, a company that helps venture-backed startups find the best people in the market. And they do it in three simple steps. First, they sit down with founders to understand their story. Second, they tell their story into multiple candidate channels. And third, they schedule interviews within 48 hours. Find us at matchrelevant.com to learn more about how we do it.  

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