Katelyn Gleason, Co-founder & CEO, Eligible
At 23, Katelyn Gleason faced, like many people in their early 20s, an existential crisis. She just didn’t know what she wanted to do.
“I started thinking about jobs. I was like ‘God if I’m going to have to do this for the rest of my life it better be something I really care about, that can be my life’s work, that I can really invest all of my time and all my energy into,’” Gleason says.
Her first step was to start reading the biographies of some of the greatest individuals in human history—Marie Curie, Jane Austen, Abraham Lincoln, anything she could get her hands on. Gleason’s goal was to learn as much as she could about these great people and how they managed to leave such a large legacy and imprint on humankind today.
It wasn’t long before Gleason found herself immersed in the world of healthcare, technology, and startups. It was there she found her purpose. Gleason noticed a problem in the medical industry that no one seemed to be talking about or trying to solve. Doctors and patients alike were getting bogged down with paperwork that was often confusing, and as a result, many were dealing with huge costs simply by filling out the wrong forms.
The next nine months were spent at her kitchen table, furiously working on a solution to this problem. That solution would end up becoming Eligible, a medical billing startup designed to make it as simple as possible for doctors and insurance companies to work together and save everyone money, patients, doctors, insurance companies alike.
As a two-time alumni of Y-Combinator, Gleason led Eligible from quietly testing and validating its product to becoming an explosive fast-growth company. Today, Eligible processes 14 million transactions per month, with a projected 50 million transactions by the end of the year, and has raised more than $25 million in funding.
- Every step you need to take as the founder of a startup, from validating to raising capital
- How to gain proof of concept as quickly as possible
- Where to find co-founders to complement your own skills and talents
- What strategies you can use to build a fast-growth company
- How to manage the people around you and keep them focused on your goal
Full Transcript of Podcast with Katelyn Gleason
Nathan: Hello and welcome to another episode of the “Foundr Podcast.” My name is Nathan Chan and I am coming to you live from Melbourne, Australia. I am the CEO of “Foundr Magazine” and the founder of “Foundr Magazine,” and the host of the “Foundr Podcast.” And today, we have an amazing guest, the founder of eligible.com, Katelyn Gleason. And she come out of Y Combinator, she’s done it two times. And one thing that, you know, I will mention this to you guys but I recently joined, oh, actually about a year ago now, almost a year ago I joined this group, like, a little bit like a mastermind called EO, Entrepreneurs’ Organization.
Incredible group and, you know, you meet some really, really smart people. And, you know, you join this thing called a forum which is like your little group. And there’s, you know, nine people in our forum here in Melbourne and they have chapters all around the world. And I catch up with this group of nine people every single month. And, you know, we talked about our challenges. Everyone has all sorts of different businesses and all sorts of different industries and niches, and we all talk about our challenges and we help each other work through them from experience sharing. It’s not opinion, it’s experience sharing which is really, really cool and powerful.
And where I’m going with this is, the common things that I found from being in the EO and speaking to, you know, entrepreneurs, staff, founders, these are the common things that, you know, entrepreneurs, business owners, staff, founders face. One, cash flow. Two, people. And literally, those are the number two things that people always face, cash flow and people. And in today’s episode, we talk with Katelyn about managing people when you have a fast-growth startup hiring strategies, leadership strategies, how to manage the growth while you’re finding and building a leadership team, how to utilize your advisory board.
So, it’s a great interview, a lot of gold shared. And I just want to share with you also, before we jump in, you know, my vision for Foundr is to build a household name entrepreneurial brand. And I have the vision of having tens of millions of people consuming our content every single month across the magazine, across the podcast, across the blog, across our social, you name it. Right now, we’ve got millions of people but not tens of millions. And another thing that, you know, I’m working towards in one of my other visions is to build an amazingly powerful startup education platform, the best in the world.
Because there’s a lot of educational platforms but nothing curated at a really high production level just for entrepreneurship and founders. And that’s what we’re working on. You know, by the end of next year, I wanna have at least 40 highly produced, really, really high quality courses. And where, you know, we can teach them, just having the Foundr team teach them. And from a series of surveys, you know, speaking to you guys, we found out that one of the biggest problems that we have in our…that our audience has is 30%, a subset of 30% haven’t even launched a business yet.
Then we further asked those people and said, “What kind of business do you wanna launch?” And everyone said they want to launch a physical product business. So, we found an expert and that’s what we’re doing. We’re just teaming up with experts and finding and the best in the world that are just absolute superstars, proven founders, to teach how to do X or how to do Y. And we’re just about to launch our first instructive-based course, where we’ve teamed up with an instructor and getting them to teach it at high production, high quality, and it’s on how to start an online business, in particular, how to sell physical products.
So, if you wanna know how to sell online business, in particular, a physical product, please to make sure you sign up at foundrmag.com/ecommerce to get on the early bird list, to get the early bird special pricing. If you are listening to this and you haven’t launched a business yet, we wanna help solve that problem. This person actually has been on the Foundr Podcast. She’s got four multi-million dollar e-commerce brands. She’s an absolute superstar, and you’re in for a treat. So, please do go and check that out.
All right, that’s it from me, guys. I’ve told you enough about the vision, where we’re going, now let’s jump to the show.
The first question I ask everyone that comes on is, how did you get your job?
Katelyn: How did I get my job? As in right, the founder and CEO of Eligible, my job today currently, yeah?
Katelyn: God. I’ve never had someone asked me that like that. Okay. So, I started out as an actor in New York City and I was actually really frustrated because I didn’t really have many job opportunities. I sort of went to school out on Long Island, New York. And I went, you know, for acting. I did very, very well in school though. I graduated top of my class. And, you know, all throughout high school and everything, I had like one of the highest sort of IQs and which just my gifted programs and things of that nature. And I just felt like very unused and very not put to work by being an actor, a sort of like actor in New York City.
It just seemed so wrong to me. I was about 23 at the time. And I became really existential about jobs and about work. And it occurred to me that I would have to work. I don’t come from many things, so background wise, my family, you know, really struggled my whole life and there were four kids. And if I wanted a shirt, you know, it was my job to go out and get that shirt. So, existentially thinking about jobs. I was like, “God, if I’m gonna have to do this for the rest of my life, it better be something I really care about. That can be, you know, my life’s work and then I can really invest all of my time and all of my energy into.”
So, I started just like on my own sort of existential journey. I started reading biographies like every major legacy, you know, in the world. Everything from like Madame Curie to like Jane Austen, to Ayn Rand, to Benjamin Franklin, to anything and everything, Abraham Lincoln. Anything and everything I could possibly get my hands on. It’s about people who had, what I feel like had sort of lit their torch in the world and let it burn really great. Again, I was like 23, needing a job and decided, okay, I need to figure out how I’m gonna make this work. So, the only thing I really knew at that time had to do with sell. So, I sort of just look for a sales job.
I had one pre-requisite for the job. I kinda knew I could walk into any place and get any sales job I wanted. So, I said, “Okay, I’m gonna get a sales job where I could be working for the people who made the things that I was about to sell.” Because then I thought like I could, like at least help them make their products better if, you know, the shit sucked. So, I found a company via Craigslist which they hate when I tell people that story. They’re like, “Can you like make up something more romantic, like, than Craigslist?” But I found them on Craigslist. It was like a startup company that work with doctors. That’s, you know, this kinda lead me to my job at Eligible now.
It was a startup company, they had an iPad app at 2010. They were the only iPad app in the app store for doctors, so anytime a doctor got an iPad, that was the app they downloaded. So, we had the incredible distribution right off the bat. So, I found these two founders, they had built this iPad app, that was really interesting to me. And I was like, “Okay, I can help these guys. They don’t know how to sell. I can go and sell this thing.” Make them a ton of money and like get my sort of way into this world than I haven’t really knew now existed. Prior to that, I hated tech. I was an artist, I thought tech was like ruining everything. So, yeah.
So, getting that job with them is what led me to healthcare, it’s what led me to check, it’s what led me to startups. And it’s what led me to a program called Y Combinator which is a really prominent investor group that’s invested in Dropbox, Reddit, Airbnb, Stripe, and just some of like the most successful startups in the world. So, we get into Y Combinator. I’m with this company, I learned all about this sort of culture. And I see a huge problem that’s not being served in healthcare with patient billing and insurance billing. And sort of streamlining that process for providers. I always tell a story that I was working with like one of the top oncologists in the country.
They were, you know, curing cancer essentially, and they have like 5 million dollars’ worth of their own money wrapped up in health insurance companies out here just because they filled out that paperwork wrong. And that was just so sad to me, like this doctor should be focusing on like medicine and curing cancer, and like, he’s, like, filling out paperwork wrong. And he’s got stacks of paperworks that he’s sending me to like help him get these 5 million, that’s his money. So, that was like just so sad to me. I identified that problem out there in Silicon Valley. I, sort of, went out by myself, sat at my kitchen table for 9 months and $5,000 is all I had, and then a whole shit load of credit card debt.
And I literally sat there by myself, at my kitchen table, and was like, “I am going to put together a prototype of how I will solve this problem. It is going to happen.” And I just got very obsessive. I did not see my family, my friends for like that entire time. And I just focused entirely on trying to build some proof of concept that could help solve this problem. Nine months later, I have like just about run out of money. I always tell the story that I like walk into like a yogurt store and like, I tried to get a frozen yogurt and my last credit card declined, and I was like, “Oh, shit. I’m so screwed. Like, what am I gonna do?” And literally, I think it was like two days later I raised my first batch of money and that was from YC.
And thank God, it was like 150K, and I was able to, like, pay off all my credit card debt, like before any interest tipped. Oh, yes. But, yeah, I always tell that story because it just shows you, like you’re so close to absolute destruction and failure. And then boom, it just happened. So, I had a prototype, it was a working prototype, I had like one customer and they’re paying me for it. And like, I gotten to YC, raised 150K, and I could start like building the company. Right after YC, I was able to raise 1.6 million, so I took that for 3 years and just obsessively built the company very quietly. What we do is we go out and that’s like how I have my job, right?
So, like, we go out and we connect to every major health insurer in United States. There are thousands of different health insurance policies, hundreds of different payers. And we go out and we build connectivity to them and then we make it simple for folks that Cleveland Clinic, which is a major hospital out here, RadNet Radiology which is a radiology center out here, for them to interact and build interfaces with all these insurance companies, that’s what we do. And, like I said for the first, you know, the first chunk of the company, there were eight people. We were, you know, just a real hardcore startup.
And I brought us to profitability, you know, making over a million dollars in annual recurring revenue. And then I went out and raised capital, you know, like the big check. So, I think all in total now, we’ve got about 25 million that I’ve brought in, but that was after we’ve sort of like proved product market fit, proved our first customers, we were ramping up, grew rate point 4X, and, you know, we are making a lot of money. Now, the company is 53 people and I have my job now as CEO and founder which is changing every single day. And, yeah, that’s how I got my job.
Nathan: Yeah, wow. That was an incredible story. I have a lot of questions.
Nathan: So, you mentioned about a product type that you worked on for eight, nine months before you got into YC. What did that look like and how did you know what that would be?
Katelyn: Yes. So, I didn’t at first. First of all, it ended up being an iPhone app that could check a patient’s eligibility. So, it could check for patient’s billing responsibility if they were going to get a service of care. So, it was a nice phone app, but as a patient, you can put in your insurance and so, and you could get like your deductible information, your co-insurance information on behalf of whatever provider we were demoing for. So, provider means like doctors, so whatever doctor we were demoing the app for. So, it’s just like a simple app prototype. So, in the beginning, I knew that there were…so there’s something called HIPAA in the US that came out and made me sick.
So, when I first went out on my own, like, okay. I was like, okay, I know that HIPAA actually forces the insurance companies to put this information out electronically. So, most people don’t know this but the P in HIPAA, it’s actually not privacy, it’s portability. So, like, they’re forced to port out this data. And I know I was one of the very first people that really understand that and kind of share that information with Silicon Valley. But I knew that they had to do that, so I could leverage that. And there are a lot of old, like, aggregators in the space, like very old, byzantine aggregators that you would take a ton of money to.
But that they would, in terms of like per transaction, like every time you send them a transaction, you pay them like 50 cents or something. But it was enough that I could build on top of them just to start and show the proof of concept, and show, “Hey, people really would want this even if we’re not processing high volumes.” So, doing like 5 or 10 transactions at 50 cents, it doesn’t matter. You know, now we do 12.7 a month, so that would not be possible. But back then, that was okay to just kinda show a prototype. And yeah, it just kinda lead from there. So, like, I kind of just followed the pattern, did a lot of reading, found the right people, and then like kind of put it all together in this simple iPhone app that really didn’t do much but just prove that the concept was possible.
Nathan: I see. And with the prototype, you designed it. You developed it yourself? So, you self-taught to…?
Katelyn: Yes. So, with the prototype, I went out, yes. So, I sat there, so, again, like I went to school for acting, so I had to teach myself everything, right? So, like, I remember this first time I made us a website. It was the most ridiculous website ever and I made it myself. And I used, like, GoDaddy and, like, FileZilla. And, like, so when I first realized that code, it was like a bunch of TXT files. And I was like sat there by myself and just like, you know, I even back then kinda knew about what XHTML and like CSS. And, like, I knew if I could, like, I would build up a prototype in like Photoshop and then give it to, like, front end folks to make me that.
And then like I went and like uploaded that on FileZilla. It was like with GoDaddy it was like ridiculous, but that’s what I did in the very beginning. And then I was able to recruit my fiancé at the time, his cousin. And he was like an iPhone app developer and I, like, paid him at first, and then eventually gave him equity. But I just had him like build the iPhone app and build all the, like, background files, so no story board. So, I would just build all the need files and then he would, like, go and like blends them all up. So, he did the iPhone app development and then I went on Stack Overflow and I found a gentleman who bid in Brussels.
And he had like four kids, he was like 50 years old. He, like, worked at ING Bank and I got him to moonlight and just help me to, again, this is just a proof of concept prototype, so like we didn’t have to ever reuse this code and like we don’t use it today. But he could, like, help me just build the proof of concept of like going to this aggregator, sending this inquiry, and getting back the results. And, you know, it just kinda really keep it very simple through that. So, that’s how I got like that first prototype built. And I did so much…like I remember even things like very simple things that now, like, it’s actually insane for me not to have known but I didn’t even know where the REST API was at that point.
I didn’t even know what JSON was. When we were… uses very old, byzantine format via, like, it’s something called X12 and that’s what’s mandated to use in the United States. So, we were using that and then we were building like an API on top of it which is what we do today. But I was like having the dude send me like a string of variable because that’s what I knew how to push, like I didn’t know what JSON was. I had just literally like go in Stack Overflow to figure out what JSON was. Like, and it wasn’t even… I remember asking them, like, “I’m having him send me a string of variables. I think it should be XML.”
And someone was like, “Oh, you should probably use JSON.” I’m like, “Okay.” And I start Googling JSON. Like it’s ridiculous to go back and like all of that is, like, public. You can go back and check with 2011, like my question of, “Should we use JSON?” I mean it’s like really funny stuff. So, yeah, it was real, for me, this has been a real personal lifetime journey. You know, I have learned so much over the past five years because of this, and like have taught so much to myself, and then have learned so much from other people. But yes, I had to literally start from absolutely no experience whatsoever and just be enough to be dangerous.
I mean, three years in when I was running Eligible, I was the VP of Engineering, I was the VP of Tech Ops because we didn’t have a leadership team. I was the CTO. I mean, for years. So, it’s like we were setting up VPNs, like I was in there, like, setting up VPNs, like that’s how it was going down. And we were building our design, like, architecture for logging, like I was in there. I can still talk to our tech ops team and our engineering team about that today. So, there was really…there’s no part of our entire system that you can point to that I don’t understand like how it works, at least today. That may change, I guess.
Nathan: Wow. That’s very, very full on.
Katelyn: Yeah. Yeah, I don’t know how to do anything that fast.
Nathan: Wow, okay. So, when you got into YC, did you join with a co-founder. Was that your fiance’s cousin?
Katelyn: So, that’s actually very good question. So, he came to YC with me. I went to the interview by myself and I got in by myself. And then I had him and then I also tried to get this moonlighter from Belgium to come as well. So, I think I only actually ended up meeting in person one time out of that whole year that he worked with me. And they both had equity in the company still today. But the one in Belgium had, like, four kids and he just, like, couldn’t commit to anything. And then the young lad, preferred to go, like, go to his, like, senior prom and I was like, “Listen, dude. We’re in YC, like you’re gonna make a choice, we’re gonna do this or not.”
So, he just…I think it was even before demo day, so it was like a month before YC ended, he decided to leave. And, you know, we let him pass and take some of his shares, but he decided to leave. So, here I am, like non-technical co-founder, sitting in Y Combinator like the best thing in the world. It was, like, talk about like the lowest of lows. And I remember going to see Paul Graham, I had like an Office Hour. And I, like, walked into the Office Hour and I was like, “I cannot go to demo day.” I was like, “I can’t go by myself, you know.” And then I started…then he’s like, “Well, just pull all that aside, just talk what’s the product.”
So, we had gotten the product to a pretty stable version. I mean decent enough that it was a decent enough prototype that we could have like a live customer who’s paying us, I think it was like $5,000 a month. It wasn’t a lot of money but it was like something. And he’s like, “Wait a minute, you have something, it works. It could be ginormous one day. It’s going to…I mean it’s healthcare so the market is just gigantic. It’s a huge problem. You’ve solved it for yourself on your iPhone app and now you can go solve it for tons of other people. Why would you give up now?” And, like, I just needed that, like, I just needed that, you know? Like I just needed to not feel alone like for that second, and thank god.
Sometimes I wonder, I’m like, “Ah, but I have just given up, like, then, you know.” But, yeah. So, I went to demo day by myself, solo founder, no technical co-founder and I’m still able to raise the 1.6 million, so I was very, very happy. And it was mainly just raising it on the vision, on the opportunity, on the inbounds. We just have quite a bit, we did a soft launch on Hacker News and just with that alone, no PR, nothing like that. We had incredible leads coming to us and still do until this day completely organically. So, you kinda knew, “God, we’re definitely building something people want for sure.”
Nathan: Yeah, wow. Awesome, that’s really impressive. So, still to this day, you’re single founder, sole majority share owner?
Katelyn: Oh, yeah. Oh, yes. So, a single founder, majority shareholder, full birth control, so I have the full control of the company until this day.
Nathan: Awesome. Okay, fantastic. So, when I go to your website, it says you guys are now Fortune 500 company and that you’ve scaled, which is I thought was interesting. You said perfectly scaled from startup to the Fortune 500. Like, talk us about scaling this company.
Katelyn: So, to be clear, that’s in regards to our customers. So, our product scale is from startups to Fortune 500 companies. Does that makes sense?
Nathan: Ah, got you, got you, got you, yeah. Okay, that’s my bad.
Katelyn: No, no, no, no worries, no worries. Yeah. So, our actual product, so the mass majority of our customers that generate, you know, millions of dollars of annual recurring revenue for us, they are public companies. So, when we go out and bring on, you know, like I said, at Providence Healthcare or Cleveland Clinic, or RadNet Radiology. These guys are doing billions dollars in annual recurring revenue and we’re increasing their revenue sometimes by, you know, just astronomical numbers. So, yeah, so we worked with a lot of top, you know, billion dollar public companies. And then we can also work with brand new healthcare startups.
So, you have someone like Omada Health which is like a big sort of buzz healthcare startup. Where you have someone like counsel or you have someone like every day health. And these guys are all, you know, “startups” but they are able to use this in the exact same way that, you know, billion dollar companies use that.
Nathan: Got you, got you, I see. Okay. So, talk to us about, I guess building and growing the business. Has it been easy?
Katelyn: No, there’s never been anything more painful than growing this business. I would say my favorite year was like the first year when I was like one of the most peaceful year, it was like my first year when I was just like laying out on the grass and like thinking and planning and being an artist. Growing this company has been such, I mean…like I love challenges. So, for me, growing a company is like the ultimate challenge. It changes every single day. Every single day, I feel like I’m failing and I have to figure out like a better way to solve a problem. So, last year, we more than doubled our team size and now we’re 53 people.
And I think the single most important piece of advice that I was given last year when this was happening, well, actually before it happened was go out and hire a killer leadership team. Because as you bring in a killer leadership team, they will bring in their squad of killer employees. And it was so true. And it seems almost counterintuitive where something about it didn’t seem obvious to me. And I’m absolutely certain that I would not have thought of that, had someone not explain that to me. But it was absolutely true. So, I’d go out and I hire, you know, a VP of Tech Ops and all of a sudden you have five, you know, incredible tech ops engineers that wanna come and work with you, right?
Because they’ve worked with them before, this guy has been doing it for 20 years. He’s reliable, they adore him, they just wanna be with him, right? So, like, all of a sudden you’ve got all these folks coming in working for you. Exact same thing happened with our VP of Engineering, same thing happened with our CTO, same thing happened with our Chief Security Officer. And these are all like heavy duty, really forward or advanced in their technology folks. So, yeah, that was the absolute best thing I could have ever have done. Had I not done that, it would have been even more painful than it is.
I think being a girl does make it actually really hard. I don’t mean…like, whatever. I shouldn’t even say being a girl, being sensitive makes it really hard. I think that I had to really put a lot of feedback in perspective when you’re growing so fast and there are so many new faces. Everyone has an answer as to what way you should be doing something. And I think I was a little sensitive for that and I think that landed itself at just being a little bit more painful than it had to be. I think now, the second time around, so we’ll probably double our team size again this year. That’s gonna be tremendous, right? That’s gonna be a huge difference from…yeah.
And I feel ready for that now though. Because I have the infrastructure in place, I have like just the processes in place to it. Like, I have the leadership team in place, like with our vision. Everyone is on the same page, everyone is saying they have the same vocabulary that we did not have a year ago, right? So, I feel like, “Okay, yeah. Now doing it will be so much easier.” Oh, god, this last year, wooh. Yeah, huge, huge learning experience, that’s for sure.
Nathan: Hi, guys. Just wanna take a quick second to let you know about our sponsor for today’s episode, FreshBooks. FreshBooks makes cloud accounting software for entrepreneurs so ridiculously easy to use. They’ve now helped over 10 million people, save time, and get paid faster. What makes them so great? Sending an invoice in under 30 seconds and automating late payment reminders and sending up online payments in just two clicks is a good place to start. The world is not built for the self-employed but luckily, we’ve got FreshBooks. I highly recommend them and now they’re offering our listeners a 30-day free trial. So, if you go to freshbooks.com, so freshbooks.com/foundr and enter F-O-U-N-D-R in the “How did you hear about us” section. Because remember, when you’re supporting our sponsors, you’re supporting the show. Okay, now let’s jump back in.
Talk to us about the leadership and management piece. Because even though bring…like you have to manage all these people, right?
Katelyn: Yeah. The hardest thing that I had to deal with was understanding that your leadership team is there to execute on your vision. It’s sometimes, again, super easy, like hindsight is 20/20 or whatever they say. But it definitely seems logical, right? But for some reason, it was counterintuitive to me. So, your leadership team is there to understand, you know, and execute on your plan. Yes, it is absolutely their job to push back on you. But it is absolutely their job to execute on the plan that you lay out together, and that is really, really important. And I’ve read a lot of, you know, good books and I think it’s high output management and then there is like the one minute manager.
And there’s just like a lot out there that you can read, but that was really important for me to grasp. But know their mean and they are to be your sort of arms throughout the org, right? So, the closer you are with them, the more on the same page you are with them. And you can’t, like I wanted so bad in the beginning to control them. It sounds so bad but like it was so wrong, like I’d wanted to, like, control it and it was like that’s the absolute worst way to go, it’s from my experience at least. What I found is that the more I give them context, the more information I share with them, the more I just give them more and more just details, the more they automatically do what makes me happy.
Because then they’re in the group two, right? Like they see it. There, it’s just so much better. So, that was the big thing that I had to learn this year was like, instead of trying to control and kind of micromanage. And you just can’t help it when you go from something so small to so big, so fast, like, and just me being the person I am, I just wanted to like micromanage everything and it was the worst. It just resulted in me exact opposite results that I wanted. So, I found, I was like, I kind of, like, let go of the micromanaging, let’s focus on information, focus on content, focus on getting them everything they need. That really, really worked.
Nathan: I see, that makes sense. And how often do you catch up with them?
Katelyn: Oh, I think constant… At least like once a day I’m having just like a quick interactions with them. Depending on where our focus is, you know, especially just like focus through the quarter. You know, I may spend…you know, every day, at some point during the day for an hour a day with, you know, a certain part of that team. That all really depends on where the focus is for that quarter.
Nathan: Got you, I see. And do you do standups with them daily?
Katelyn: Yeah. So, daily, and that’s kind of interesting because I’m so in the weeds when I do take the time to be with them. It’s that that standup sometimes end up being a bit longer, like an hour. But it really is to just kind of break down, you know what’s going on but yes, definitely daily. Not daily with all, daily with whatever the focus there is for that week.
Nathan: Got you, I see. And you plan out the weeks and the months, and the quarters?
Katelyn: Yes, yes.
Nathan: Got you, I see. And talk to us about the domain. Eligible.com, that’s a very, very, very strong domain. When did you guys acquire that?
Katelyn: Yeah. You know what, so we got it last year only. We just got the trademark as well which is very nice. I’m very happy about that. Yeah, it is a killer, isn’t it? I mean that’s a hell of a word. Yeah, I was very, very happy about it now.
Nathan: And what did you have before?
Nathan: Got you. And was it expensive?
Katelyn: No, it actually wasn’t that bad. I think it was like 250K.
Nathan: Yeah, geez, that’s good. That is really good.
Katelyn: I know, considering. I mean it could get really bad.
Nathan: Yeah. We actually just recently acquired our own domain, so foundr.com but with our spelling. And yeah, I can see how that can get really, really expensive. So, I’m also really curious. You said you’ve raised, was it over 20 million now?
Katelyn: Yeah. So, in total it’s a bit over 25.
Nathan: Okay, got you. How do you work out where to allocate those funds and also when to go for profitability?
Katelyn: Yeah. So, for me, I’m always shooting for profitability just because I’m that kind of founder, but I am also always investing in the future. So, for us, it’s actually super clear because we have a number of sort of deals or contracts that are closed. And it’s just a matter of catering to those deals and getting those deals live. So, for us, in terms of allocating resources, focusing always on the user and always on the team. So, things are always through that vision, right? So, making sure our customers are taken care of and making sure our team are taken care of. You take care of those two things, everything else takes care of itself.
So, that’s definitely where the budgeting comes into effect. And when we budget everything out, those are always our two focal points, customer and then team. In terms of profitability, you know, for me, so our business is just great economics. It’s actually not a sort of standard venture capital business in a sense where we do not have to have like negative growth margins and crazy things like that. We can argue that our only cost, our infrastructure cost. So, for every five cents that we charge, we get to keep those five cents. And that’s kind of incredible for, you know, to Silicon Valley and just for the tech startups in general.
So, our economic share are really, really strong. They’re really, really good. The only reason we’re not profitable right now is just an investment and growth. So, it’s an investment in getting these deals which will make us profitable to, you know, substantial revenue and to, you know, deployments.
Nathan: Got you. And do you think you will raise a series B?
Katelyn: There is a very good chance. Well, just a story. In terms of this capital we’ve raised, it’s actually not an official theory day. So, we’ve done it…yeah. So, we’ve done it via, just like super angel rounds and that’s high, I remain in complete control of the company. So, there is like no other board member but me right now at the time, which is pretty incredible especially for raising that much capital, yeah. There is a chance. Well, we just will never have to raise capital ever again.
Nathan: Got you. And would you…you would prefer not to?
Katelyn: Absolutely, yeah.
Nathan: Got you, I see. And are you able to share with us some numbers and some traction, and also what will you anticipate in terms of growth?
Katelyn: Yeah. So, we have some things that we’re allowed to say. So, we do 12.7 million unique eligibility in claim cases per month, so that means 12.7 million patients run through our pipeline every month. So that results in billions of dollars of healthcare services annually. So, those are the numbers we were currently sharing today. For task-wise, those numbers are looking like they could double by this time next year, if not more. But yeah, that’s what we’re comfortable sharing at this point.
Nathan: Okay, awesome. Now, I’m really curious, Katelyn, solo founder, you previously worked at a startup doing sales, building a fast-growth startup, how are you learning? Most people, single, solo founder, first business, that’s a very, very high chance for failure.
Katelyn: Yeah. I think that actually I’m keenly aware of that. And I think I am that OCD about it, you know, and I don’t really have any other existence. And I believe truly that that’s the way it has to be. I kinda kid around like I had to go to some party with a friend the other day, and I think it was the first time I had been in a party in like six years, and even the friend is one of our investors, so it doesn’t mean it really count, right? Like that doesn’t count, right? Like, okay, you’re my investor. I’m meeting your other hedge fund friends, this doesn’t count. So, yeah, I mean I just don’t really had any other life other than this.
There’s some folks thinks it’s weird, right? Some folks, you know, you just get a lot of judgement about it. But for me, I truly believe it’s the only way that it can work. I need expensive amount of time to think and dream, and plan, and build, and repeat. So, for me, it’s a full on commitment. This is my child, I have no children, I have no, like, significant other. This is a 100% Katelyn. So, yeah, I think that’s the only way that I can, at least, turn around at the end of the day and say, “Listen, I gave it my all to avoid, you know, some of the pitfalls.” And listen, I fail every single day and I get back up. So, I think it’s also a bit about that as well.
Nathan: Yeah, that’s really interesting around the obsession piece. I agree with you. But what about weekends and stuff? Like, talk to us about hours. Are you doing 80 hours still every single week?
Katelyn: I’d probably would say more. I mean I don’t, I mean there’s… Friday night I tend to like I’ll do something, like, you know what I mean? It’s like hopefully, sometimes, you know, like maybe I’ll go out on a date, like maybe. You know, like Friday nights but like I’m not, like, really that’s it. Like really, truly that’s it. Like, yeah, like Saturday, Sunday, like that’s the entire time. I mean I like some stuff, like I like girl stuff. I will get my hair done, I’ll have my makeup done sometimes, you know what I mean? Like, I don’t really need to work out, I’m pretty tiny, like I don’t have that sort of blah or whatever. But I like girl stuff. So, like, that’s like my fun stuff, but yeah. Like even weekends, absolutely weekends are my most important time because no one is asking me a million questions. I work every single night, I work every single morning.
Nathan: Have you ever got burned out yet?
Katelyn: Yeah, I think I did in like 2014, and I was really able to just kinda give myself what I needed to get back, and it worked out perfectly. I could recharge before the big growth spurt which is nice. Yeah, I really… Everybody is different and I think that’s because a lot of my work I believe is day…like I’m often daydreaming, and to me that’s work. You know, I will sit there and have to think or go for a walk or just drink a latte, and like that’s me. And, you know, I’ll go off on my own and like do that. That to me is work. So, it’s not just crunching the whole time. It’s just kind of all-consuming I would say.
Nathan: Yeah, yeah. But you’re always on and I’m just saying. I totally get it, yeah.
Katelyn: Always on.
Nathan: I totally get it. You said it that when you burnt out, you recovered. How did you recover?
Katelyn: A ton of things. So, when I burnt out at that point, I had not seen my family in like three years almost. I think I saw them like once. They came out to visit in Mountain View, California when I was building the company and they were so concerned about me. And I was like, “Why? I’m fine.” They come to visit, I own nothing other than like a TV. Well, I didn’t even have a TV, I don’t have a TV in like 10 years. But I had nothing but like my… No, my dad. I thought of TV because of my dad, that’s the one thing he asked for. He’s like, “How do you not have a couch and a TV?” I’m like, “No, you don’t need it.” But, like, I have like my table, my iMac, my lip-gloss, and like, my, like, you know, Murphy bed. And, I don’t know, I like it. Like I’m a hippie, like just give me that, give me a latte, give me my work, like let me roam around, like I’m just into it. And they were all like, “Oh, my god.”
But, anyway, when I burnt out, I hadn’t seen them in like three years, so it was important. Like I spent time with my family again. I saw best friends who I grew up with my whole life, who I had, like, missed all their weddings. And I caught, like, one of their weddings at the very end of that spurt. And, you know, it was just things like that, and just, sort of, aligning with that part of me that really just more girly sort of, you know, sweet part of me. And I’ve been trying ever since now. That I, like, make sure that that part doesn’t go away, so that I don’t have to burn out like that. I think that’s the only time I’ve burnt out is when I just had to like turn off all of that, like sweet, warm, like, you know, part of me. So, keeping that alive and fresh is definitely my, like, secret weapon.
Nathan: Do you meditate on a daily basis?
Katelyn: I don’t call it meditating but I daydream. And that’s actually really important thing to me because it’s by myself, it’s quiet, it’s thought, right? It’s peaceful, I love it. I don’t think it’s meditating but it’s super important to me.
Nathan: But you try and be present, right?
Katelyn: It’s super present, I’m super present. I just think I call it something different, yeah, I don’t know. To me, it’s daydreaming, like to me… Because I don’t really dream at night, like when I sleep I don’t really dream, it’s a weird thing. So, like, yeah. It’s so weird, right? I felt like because I bring them to life, like they’re real. I’m, like, my work, think about it. Like, I’m working all the time but I have to go and meet with reporters. I have to go and meet with the investors or I have to go…some constantly like surrounded by, like, incredible, amazing opportunities through people.
Nathan: One thing I really agree with you around the daydreaming piece, just, I think you need as a founder time to think, whether that any…
Nathan: And that thinking time, are you capturing it on Evernote or what?
Katelyn: Yeah. And I’ll constantly turn over to either grab my computer or grab, you know, my phone, or grab my notepad or something. But I’m a big list and like jotter-downer, right? Like ideas will come to me at all random times and like that’s the best. Yes, absolutely. Yeah.
Nathan: Yeah. And the ones are the ones that just keep coming back to you during those when you’re dreaming about daydreaming and thinking about things? Are the ones that keep coming to you more and more, they’re the ones you end up pursuing or that go higher on your priority list?
Katelyn: Yeah, I would say absolutely. And I would also say that depending on what we’re working on as a company for that week or that quarter, it felt change, right? So, they tend to not to be the same thing over and over because for something to surface at that time, it’s usually the most important, and it gets done really fast.
Nathan: Got you. But it is scheduled?
Katelyn: It does end up getting…usually yeah. I mean how… You mean my daydreaming, no, it’s definitely not scheduled. I mean it is because I’m in a rhythm and I know my rhythm and I know that on Saturday and Sunday I’m gonna spend like a span of time to sort of by myself. I’m thinking and reading, and walking, and, you know, so I do know that that is when that time will happen, just it’s not scheduled, no.
Nathan: Yeah, okay, I see it. But 100%, spending time thinking or doing things by yourself even, because I think it has to be an obsession is definitely underride at that time thinking. That’s when you need some serious gold.
Nathan: Okay. We have to work towards wrapping up. Was there any questions that you wanted me to ask you that I didn’t ask you?
Katelyn: No, I think I’m okay, I think I’m good. Yeah, I feel like I’ve been able to share quite a bit.
Nathan: Okay, awesome. Number one piece of advice for aspiring novice startup founders.
Katelyn: Just don’t give up, right? Like I really don’t think you should. I mean if it’s something you truly want and if it’s something you are willing to devote your life to, then definitely…I just remember that time when I almost gave up. And find the person who you respect and who you cherish, and who can give you that little bit of a push that you need to keep going. Like Paul Graham did for me, right?
Nathan: Yeah, that’s amazing. Awesome. And where’s the best place people can find you?
Katelyn: Yeah. Twitter is great. Obviously, Facebook is fine. LinkedIn is great. I’m super active on all those mediums. They can always email me at just [email protected]
Nathan: Awesome. Fantastic. Well, look, thank you so much for your time, Katelyn. It’s an absolute pleasure to speak with you.
Katelyn: Nice to meet you.
Nathan: Yeah, great to meet you, too.
Key Resources From Our Interview With Katelyn Gleason