
Vested Capital · 2026-03-26 · 57 min
Key moments - from our scoring
Substance score
67 / 100
Five dimensions, 20 points each
Yahya Mokhtarzada traces the path of three brothers - all co-founders of Truebill - from running a family passport and visa service through their first major exit with Webs.com (a Squarespace competitor launched in 2001) to building a unicorn in personal finance. The Webs.com story is particularly instructive: bootstrapped for five years before a Series A in 2006, it grew using viral mechanics (a branded footer on free websites) to eventually sell for $117.5 million in 2011. Yahya's departure to run the ad-tech platform Nanigans - which hit a $30 million run rate before crashing after Facebook improved its own tools - taught him hard lessons about scaling and strategic execution. Truebill emerged from a basement whiteboarding session in late 2015, built on the insight that most people don't know what subscriptions they're paying for. The app lets users see all recurring charges and cancel them with one click, plus negotiate better rates on cable, internet, and other utilities. With just under $100 million in venture funding, they scaled to $100 million ARR before Rocket Companies acquired the business. This episode appeals to operators interested in how to scale a consumer fintech product, build viral loops, navigate multiple startup cycles, and optimize founder economics in an exit.
Truebill raised less than $100 million in venture capital before being acquired for $1.275 billion, meaning over 90 percent of the acquisition money went directly to the co-founder shareholders rather than to investors.
Webs.com was a website builder launched in 2001 (initially as Free Webs) that competed with GeoCities and later Squarespace. It grew virally by placing a branded footer on every free website that invited visitors to create their own, with a premium tier to remove the footer.
Around 2007-2008, Yahya spun out to co-found Nanigans, a Facebook ad-buying platform that grew to $30 million ARR but crashed after Facebook improved its own in-house advertising products.
Truebill shows users all recurring charges on their credit cards and allows them to cancel subscriptions with one click, plus it helps negotiate better rates on bills like cable and internet.
Yahya wanted financial upside, his younger brother enjoyed building and wasn't ready to retire, and his older brother was mission-driven to impact millions of lives through technology.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode contains a solid cluster of non-obvious tactical insights - the manual concierge MVP, the mechanics of paid acquisition unit economics reaching break-even, and the counterintuitive finding that premium conversion strength matters less than retention - but it is diluted by extended biographical backstory about Webs.com and Nanigans that adds color rather than lessons.
finances are fundamentally shameful and fundamentally private... People just don't like to say, hey, I found this app that helps me with my money
you spend $100 and you make back 50... you keep doing this iterative cycle over months and months and then finally one day you spend $100 and you get back $101 and that's when the business just blows open
A few genuinely fresh observations - particularly the 'finances are shameful' explanation for fintech's viral ceiling and the honest admission of being too deferential to VCs on monetisation - but the overall arc is a standard founder-success narrative without sustained contrarian or first-principles thinking.
I banged my head against the affiliate wall for a year and a half before even trying premium. I assumed that no one would pay for this... it wasn't really until we were on death's doorstep that we tried premium out of desperation
for you to go volunteer is extremely selfish... If you really want to make an impact... best thing you could do is start a tech company, make a ton of money, and then use that money to help people
Yahya is a genuine repeat operator: hands-on CEO through the full Truebill lifecycle, previously co-founded a company that hit $30M ARR and 200 employees, and held equity through a $117.5M exit - all before Truebill. He actually did the work described, including manually cancelling subscriptions and running paid acquisition himself.
we grew to be the largest ad buying platform for Facebook... went straight up to uh, I think like a $30 million run rate and 200 employees
I started spending two hours a day, like on the phone canceling people's subscriptions
The episode is unusually number-rich for a founder story: seed round mechanics down to cheque sizes and weekly burn, the 50-cent letter API cost with a 30% take rate, precise user growth milestones, and a detailed PR-vs-scale comparison with real daily signup figures all anchor the narrative in concrete operational reality.
seed round was 2.7 million... cobbled together in checks ranging from, like, 10 to 50,000... I was going out every week and needing to raise another, you know, 25,000 to keep the company alive for another week. And we were burning 100k a month
It cost us 50 cents each time. Postage, plus a few cents... I think we charged, like, 30% of the refund
The host asks several legitimately good mechanical follow-ups (pressing on how subscription cancellation and bill negotiation actually worked at scale), but spends too long on biographical backstory, misses opportunities to push on fundraising strategy and unit economics, and produces a shallow summary takeaway ('don't listen to VCs') that lets the guest off the hook.
How did you automate? Because I don't think you can just have a button to cancel subscriptions
How did you do that at scale? Because again, that sounds like a manual
Computed from the transcript - who did the talking, and the words that came up most.
In this episode, I sit down with Yaya Mokhtarzada, one of three brothers who co-founded Truebill and sold it to Rocket Companies for over a billion dollars. Yaya shares the rollercoaster journey from bootstrapping in a basement to hitting $100M in revenue, including the manual work that got them started and the paid acquisition strategy that scaled them to unicorn status.
Transcribed and scored by The B2B Podcast Index.
Speaker A: Hi there, this is Yarrow. And welcome to Vested capital, episode number 34 with my guest Yahya Mokhtarzada, one of the co founders of Truebill, which was then acquired in very late 2021 by Rocket Companies, known for Rocket Mortgages, acquired for $1.275 billion. So a fantastic unicorn success story I have with you to share from my guest Yahya, who is one of three brothers who co founded truebill. This is such a fun podcast. Honestly, I love billion dol outcomes. Obviously big numbers is amazing and you can hear the behind the scenes of really important things like how did they scale, how did they get their first few customers, how did they get their first 10,000, first hundred thousand, all the way to the point where they reached $100 million annual run rate and then made the decision to sell to, uh, rocket companies for over a billion dollars. And as you'll hear in the story too, they had less than $100 million in venture capital raised to that point. So I'd say more than 90% of that acquisition money was pretty much in
Speaker B: the pockets of the co founders.
Speaker A: So they all did extremely well from this really fun story too, because there's a background from Yaya which he talks about his early business projects. In fact, the brothers had a company called Webs.com which was a, what you see is what you get website building tool during the kind of early squarespace period. So interesting background there with a success story, but more so for Yaya's brothers. He left that company to start an ad tech business which was an absolute rollercoaster of huge fast growth on the back of Facebook gaming and then falling back down and basically being, uh, sold
Speaker B: off for spare parts really.
Speaker A: So he experienced both seeing his brother's exit with a, uh, $100 million plus company to his own second company crashing and burning to then being the CEO
Speaker B: and co founder of a unicorn with, uh, Truebill.
Speaker A: The Truebill app itself is so interesting as a service because it kind of makes sense. It's initially as a way for you to see what you're being charged on your credit card and then basically initiating cancellations for you so you can click a button to cancel a subscription. No doubt really important because probably like me, like you, we all have these payments on our credit cards and we don't necessarily realize there's something being charged each month that we could, uh, cancel and probably should cancel to save some money. And they also have some other tools that were slowly added simple things like being able to negotiate better deals on common Bills like your cable, you know, Internet access. But really the vision for the company,
Speaker B: as Yayo talks about in the interview,
Speaker A: is to make all your financial aspects of your life more efficient. And it really is a story of true bootstrapping. I'm going to let you listen to the podcast to explain how they rolled out version 1.0, the MVP of True Bill, because it's a lot more manual than you expect, which I think, uh, certainly surprised me all the way to the point at the end of the podcast where I asked Yahya and he had a really fun answer of how his life has changed once these hundreds of millions of dollars of money hit his bank account.
Speaker B: So he'll, he'll answer that as well.
Speaker A: Great interview. Know you'll love it. Of course, as always, this podcast, you can subscribe to it wherever you get your podcast, whether you're in Apple or you're using the Spotify player or I personally have an Android phone, so I'm using the Google Podcast app. Just hit the subscribe button. Look for vested capital or look for my name, Yarrow Y A R O. And you can subscribe there and get episodes like this with Yaya and lots of other amazing entrepreneurial background stories as well. Okay, I'm going to hit play right now. Here is the interview with Yahya Mokhtarzada.
Speaker B: First question I've got to ask is how do I pronounce your last name to get that one right?
Speaker C: You know, the A is what throws it off. So it's Moktarzada. Sorry, the H is what throws it off.
Speaker B: Mukhtarzada. Okay, where's that from? What's the background?
Speaker C: That is from Afghanistan.
Speaker A: Afghanistan. Oh, uh, very cool. So you're known.
Speaker B: I mean, well, you're known for a lot, but obviously I came across you for your recent story with Truebill being acquired by Rocket for 1.275 billion. So super excited to hear that story. But I was diving into your background and I saw there's the usual lemonade stand. The lawn mowing company with your brothers, the snow shoveling business with your brothers.
Speaker A: Was it an entrepreneurial upbringing for you
Speaker B: with your family, or was that just, uh, the common practice for people in the neighborhood?
Speaker C: Yeah, I think we just grew up entrepreneurially. Our parents had a home office, which meant that at home we had multiple phone lines. It wasn't a big or especially successful company. I think they had like two employees. We had computers, we had a fax machine, we had a photocopy machine. I never saw my parents Going out and getting a job or having a boss, they had just started their own business. So that's sort of what I knew. And in a funny way, I thought, um, getting a job was more prestigious than being an entrepreneur growing up.
Speaker A: Oh, really?
Speaker C: Yeah, I thought you kind of start companies when you can't get a job, which is kind of silly, but yeah, like you said, you know, we were always kind of starting little, little either businesses or hustles. You know, I sold candy bars at school, you know, sold lemonade on the side of the road and then lawn mowing and snow shoveling. And when the Internet came out, you know, my uncle had a, uh, had a domain that he sort of gave us and he said, do what you'll you want with it. And it was tennis links dot com. And you know, this was before the days of like sophisticated search engines. And my brother got that to making about $40 a month just in ad revenue. I remember that was just incredibly mind blowing, the idea that you could put something out on the Internet, which was like this new thing that wasn't tangible or real, and make money with it. And so I think that's what got us hooked on sort of online businesses. And from there, you know, we grew up, we got smarter and got more sophisticated.
Speaker A: What was your parents business?
Speaker C: It was just a passport and visa service.
Speaker A: Okay.
Speaker B: So nothing digital or it. Okay.
Speaker C: Uh, FedEx in your passport photos and your application. They'd run it, uh, into Washington D.C. and get you a visa or passport and then FedEx it back to you.
Speaker B: Okay. Yeah, it's one of those things when you see your parents doing something. I know my parents, one was academic, one was entrepreneurial. But neither of them I saw as something I wanted to follow in their footsteps. Exactly. It was more like do the opposite of them. Sounds like to you you thought the opposite too? I'd rather get a job than do what my parents are doing. But thankfully you saw the path of entrepreneurship.
Speaker A: How much of the Internet part of
Speaker B: this do you think influenced you? Because obviously tennis links, you see the capability of making money. I know it's a cliche, but while you sleep. Because ad revenue on a website did seem somewhat easy. And I want to put this into context too. Where are we in your own life? Are we talking teenager, college age? Where did you enter this type of time of your life?
Speaker C: So I would have been just starting high school at the time, and I was very fortunate that I had older brothers who were smarter than me. So I just got to kind of piggyback on to what they were doing. Right when I was finishing high school, they were putting together a project called webs.com actually at the time was called Free Webs with a Z. And that was a create your own website blog thing, you know. And it was, it was a pretty obvious idea, like just the idea that anyone should be able to like put together a website. And so they were working on that. I was working on that part time through college. They were working on that basically full time as I was in college. And then right as I graduated, we closed the series A on that. And so I, uh, finished college and immediately moved out to San Francisco and opened the west coast office for that. Really not knowing. Running biz dev for this company that was now a good size or a series A company, really not knowing much of anything and being hugely under qualified. But it was sort of a crash course in and how startups work.
Speaker A: What's the age difference between you and your two brothers?
Speaker C: I have three brothers, but, uh, my older brother, one is three years older than me and one's four years older than me.
Speaker B: Okay. So there's a fourth brother as well who's not part of this business story anyway. Okay.
Speaker C: He is actually so truebill is my older brother. My younger brother and I.
Speaker B: Okay, wow. But there is another brother who's not. He wasn't in the founding team. Okay. What does he do, just out of curiosity?
Speaker C: He owned a tech company.
Speaker A: Okay.
Speaker C: Okay.
Speaker B: So it's all still in the world.
Speaker A: Okay.
Speaker B: So, I mean, this is. Normally I'd ask while you're in school and then you choose to go to college. Usually choose a degree that might have some kind of career path or something. It sounds like because of your brother's just leading the way with Webs.com, which I have to ask you how you got that domain name as well. Uh, they made it obvious that, okay, this is what I'm going to do after graduating. Or was there a time when you ever thought, no, I'm going to be a doctor, I'm going to be a dentist, I'm going to be a lawyer or something.
Speaker C: I was aiming to be a lawyer or work in the government because, you know, uh, like I said, it was getting started right when I was starting college. You know, for the first two, three years, it wasn't really making money. I mean, at that point in time, the business was, you know, a server in my brother's closet and, you know, an hour or two a day, I do customer support and stuff on it. I remember it started making A thousand dollars? I said, when it makes a thousand dollars total, that's when I would sort of start paying attention because they were always trying to like push me into it. When it made its first thousand dollars, that's when I was like, oh, this is kind of real. But even then I didn't think it was the path to, uh, success or wealth. I thought it was this cool thing that could, who know, maybe even subsidize law school or something. Towards the end of college was when it was sort of becoming apparent that it had the potential to be something big. But, uh, we didn't really know about venture capital or any of the things that us in the startup ecosystem sort of take for granted or sort of learn on day one. And so there's definitely a crash course in that.
Speaker B: Why is that? Were you not around entrepreneurs at the time or what is there?
Speaker C: Growing up in Maryland, there's not a big VC scene there. Uh, today it's not uncommon to start a company anywhere in America and have VCs either on the west coast or anywhere else invest. But back then the VCs who were investing in tech were all heavily concentrated on Sand Hill Road in Silicon Valley. And they, that's where they wanted to invest.
Speaker B: Okay, yeah, makes sense. With Webs.com, i'm obviously thinking of today, you know, we've got Squarespace, we've got wix, we've got some very large companies that do, uh, you know, website building tools. What was the time period that you guys launched webs?
Speaker C: Right at the same time as Squarespace.
Speaker B: Oh, really?
Speaker A: Okay, so what was the chronology of
Speaker B: this business you guys started? You get to that thousand dollars point.
Speaker C: Oh man. I want to say it started 2001. 2002, 2001.
Speaker B: So just after the dot com bubble, right?
Speaker C: Uh, right in the midst of the dot com bubble, yeah. So 2001, right in the midst of the dot com bubble. Series A was 2006 and then it was acquired right at the end of 2011. So it was exactly 10 years.
Speaker B: Okay, so it's a full on proper startup journey. I mean, I'd love to spend a little bit of time on it because it sounds like it was a, uh, success for you guys. More importantly too, like with Squarespace and everything growing, I'm curious why you decided to sell it. But can I start with the first question? How did you get webs.com? was it just the case it was 2000 and no, it was, well, free
Speaker C: webs with a Z.
Speaker B: Right. Terrible name, but yep, it generated A
Speaker C: little bit of revenue. And so we were able to acquire free webs with an S. Okay, getting better. We were able to acquire webs.com?
Speaker B: okay, so you just, you actually had to acquire it. It wasn't, uh, a $9 domain available somewhere there? No.
Speaker A: Okay.
Speaker B: My audience loves hearing that. How did you get your first customer and then how did you get to your six figures, seven figures? In summary, like, what was the marketing kind of growth journey of that business? Because it is somewhat generic, standardized web building tools. There's WordPress, there's nowadays Squarespace, and so on. So what was it like for you guys?
Speaker C: I certainly wouldn't start it now. Back then, I think it was two things. One, GeoCities was around, but GeoCities sites just looked schlocky, right?
Speaker B: I said one.
Speaker C: Yeah. So we really wanted to just make it easy to make a website that actually looked decent. Obviously it didn't look professional, but it looked decent. I don't know if you remember, this was the era of like the under construction banners and things.
Speaker B: Yeah. I had a GeoCities website in the late 90s, so. I know, exactly. And there was, uh.
Speaker A: What was the other one?
Speaker B: There was Angelfire. There was quite a few at that time. Yeah, yeah.
Speaker C: But there was a really nice sort of viral mechanic in it, which was, you know, the website was free, and then at the bottom of the website was a bar that said, you know, this site is host, built and hosted for free by freewebs. Click here to get your own website. Right. And if you wanted to get rid of that, you could pay and go premium. And if you didn't, then everyone who visited your website saw it. So it did have an inherent viral mechanism in it from day one.
Speaker B: And that's what led to the growth. It's a fairly technical thing to do, build a website builder. Were all three of you founders who code at that point?
Speaker C: No. My oldest brother and my younger brother were technical and then the other two of us were not.
Speaker B: Okay, so when you came together with webs.com by default you just fell into the right roles for your skill sets or.
Speaker C: Yes, My oldest brother was cto. My younger brother, who was in high school at the time, was an engineer, and then my older brother was CEO, head of product, and then I tagged in on biz dev and wherever else could be helpful.
Speaker B: Okay, and what did your parents think of all four of you guys going into one business together?
Speaker C: I think they really liked that we all worked together. But I think that, you know, for the older generation like being an entrepreneur, starting a uh, web company was not prestigious. Right. So I think they wanted us to be doctors, lawyers or academics. Uh, I think it wasn't until really the exit that it sort of hit them that, wow, this is a real thing and there's something here.
Speaker B: Okay, well take us through that exit. So it's a 10 year journey. I know. Was it a case of just improving the software, scaling up, marketing, ad spend? Obviously more M tools are coming out. Google search, eventually Facebook, so on. Is that kind of what happened or was it bit more rough than that kind of journey? And also I'm curious, all four of you running this together. Like I can't imagine working with siblings and deciding, you know, making big decisions all the time together.
Speaker C: Well, so I had left, I had left and done, uh, an ad tech startup. I was working on an ad tech startup. Okay, so three of them were still there. So in 2000, uh, 2007 I guess, I don't know if you remember, the Facebook platform launched or maybe 2008. And so we spun out a company from webs called SGN or social Gaming Network, making uh, Facebook games. And so a couple of us from web spun out and started that and that went up and then not so up after a while. In terms of the exit, I think, I don't want to speak for my brothers, but they were at it for 10 years. The company was not in a hyper growth phase. Squarespace was still growing really quickly. But webs, I don't want to say it was plateaued, but it was kind of chugging along. I think they were ready. You know, the offer came in, it ended up selling for 117.5 million, which at the time seemed like all the money in the world. And I think it was the right price at the right time for them and they accepted.
Speaker B: So you were still a shareholder I assume as a co founder as well. And you raised a series A along the way. Was there a series B or anything after just an A? Okay, so you had some bootstrapped for
Speaker C: five years up to the A and then, and then the A carried till the exit.
Speaker B: So when this exit happened, you're uh, not part of the company, but obviously you get the windfall. Where were you at that time? Were you still doing the ad?
Speaker C: I was doing ad tech.
Speaker B: Ad tech. Okay.
Speaker C: So it was a company called Nanigans. We grew to be the largest ad buying platform for Facebook. And that was uh, just a roller coaster where it went straight up to uh, I think like a $30 million run rate and 200 employees. And then came crashing down as we made some strategic mistakes and as Facebook sort of improved their own in house products.
Speaker B: Oh, wow. Okay, so, ah, that's a story I didn't see on your bio anywhere. That's a whole other company there. Okay. All right, so can I get your mindset where you're at when the exit happened with Webs, and then you're obviously in the middle of a roller coaster ride with your ad tech company?
Speaker C: Yeah, well, Mannequins wasn't a roller coaster ride yet. It was still straight up.
Speaker B: Okay, that was a good time. So to you, this exit's happening and you're like, great, but I'm all focused on maintaining this crazy, uh, rocket to the moon that was happening.
Speaker C: Everything was going right for that business. And so, you know, I was ecstatic for my brothers. You know, that made the idea of an exit just seem suddenly within reach, intangible. And so it really fired me up for what we were doing at Nanigans to try to go bigger. Right. And at the time, ad tech is kind of a very unattractive industry right now, but at the time, it was kind of hot. And there's all sorts of companies selling for three or four or $500 million or even a billion dollars in ad tech. And so that seemed within reach within a couple years.
Speaker B: Right, so remember Doubleclick? That was an earlier timeframe, I think,
Speaker C: when they were 3 billion.
Speaker B: Yeah, by Google, Right? Yeah, that was a big one.
Speaker A: Okay, so there's a lot of history
Speaker B: before you even got to truebill with all of this. I mean, I could spend an hour talking about each company, but just from the two experiences of the web with your brothers and then Nanigans, was that what it was? The ad tech company one, clearly you have 100 million plus exit. That's obviously a success. I mean, your parents must have been like, okay, yeah, you guys made a good choice at the end of the day. And then did you end up having an exit with Nanigans, or was it just a case of no?
Speaker C: Nanigan sold its primary asset to fund R and D, and it's still kind of going.
Speaker B: Okay, so by the tone of your voice, you weren't happy with the exit that it was that the closing of
Speaker C: a check, there's no liquidity from the exit. It all went back into.
Speaker A: So you'd seen kind of both.
Speaker B: Then you'd seen a company that had a decade run, got acquired, and then you'd seen a company that grew like crazy. But then Fizzled. So you really knew both stories in terms of potential outcomes. How does all this play out to the truebill story? Like, was it a case of, I mean, brothers? Must have been like, oh, we're exhausted. We don't want to jump into a startup. We just made a bunch of money. We're going to, like.
Speaker C: So we started Truebill right at the end of 2015, and Web sold at the end of 2011. So we're.
Speaker B: That's four years between. Yeah. Okay. Did you guys travel around the world, have a break, was there? No.
Speaker C: No. So two of them, um, stayed at Webs for, I think, two years. One was still at Webs, and I left Nanigans maybe six months. So three of us were not working. And I was really the one that was like, hey, let's get the band back together and do this again.
Speaker B: Right?
Speaker C: I just looked at, you know, how little we knew going into webs, how much I learned at Nanigans and all the mistakes we made that I wouldn't make again. And it's like, you know, like, we've learned so much. Like, if last time we got to, you know, this point, like, imagine how much further we can get now knowing what we know. You know, we all got together in my brother's basement and, like, you know, pulled out a whiteboard and just started whiteboarding ideas and came up with nothing. And then that's, uh, how truebill was born.
Speaker B: Oh, yeah, of course. Logical connection. I have read up. So I do know kind of how you, uh, sort of came to the idea, but I'll let you share that story in a second. I just want to know, though, in terms of motivations for starting another company after the stories you guys already went through, is it just a case of seeing. Because, like, financially, I don't think it's as important. You've already made enough money that you guys are obviously not going to be struggling. But you're thinking, we want to do another company because we want to do all the things that we now know better, reach a bigger milestone. What was the core motivation behind getting back into another startup?
Speaker C: Each of us had a different motivation. I wanted to make money. My younger brother just likes building stuff. And he must have been just turning 30 at the time, if that. Uh, 29, 30, something like that. And I just think he wasn't ready to retire. He wanted to keep going. My older brother is super mission driven. He's 100% certain that what drives him is meaningfully improving the lives of millions of people. And he says that Constantly I was goading him and trying to push him into doing this for a while. He was like, I might want to just go do some non, um, profit stuff or volunteer. And, uh, one of the things I said to him, I don't know if this motivated him or not, but I was trying to convince him. And I said, listen, for you to go volunteer is extremely selfish. I said, what are you gonna do? You're gonna go serve soup in a soup kitchen? You're gonna do that because it makes you feel good. But realistically, you have this skill set that's worth millions or tens of millions or however many millions of dollars. If you really want to make an impact and you really want to help people, best thing you could do is start a tech company, make a ton of money, and then use that money to help people. So if you do less than that, if you go serve soup, you're doing that for you. You're not doing that for others. Which is, as I said, it's a very manipulative thing to say.
Speaker A: You're really pulling the heartstrings for him there.
Speaker C: I think me sort of bugging him for weeks, kind of nudge him in that direction. I think also he's just a natural problem solver. I think he sees inefficiencies, wants to fix them, and he's just the type to build stuff, and it's his nature. And the combination of all those things sort of became too much to walk away from.
Speaker B: And you, what was your motivation?
Speaker C: I wanted to build a big, successful company.
Speaker B: Okay, so you were feeling not satisfied from the previous two. You were still hungry for more?
Speaker C: Well, webs, I wasn't there for the exit. Nanigans kind of came crashing down. Uh, and I was in my early 30s, and so I just am still a worker.
Speaker B: Yeah, yeah. Bigger and better next mountain.
Speaker C: I just don't think I'm m the type to sit on a beach. I've done that for periods of time. And it's a funny thing, waking up on a beach and saying, you know what? I feel not awesome. And then you have to dig into why do I not feel awesome and when do I feel the best? I realized that for me, I'm at my happiest when I have a tangible, measurable goal and I'm making progress towards it.
Speaker B: Makes sense. I'm very similar.
Speaker A: Okay, so you didn't come up with
Speaker B: an idea with the whiteboarding session. And I believe this was somewhere. Uh, there's always a cliche story in a basement, but I don't think you guys had to be in a basement. That's just where you chose to do this. Where did the idea or the germ of the original idea for True Bill come from?
Speaker C: So after, like, I don't know, a couple days staring at this whiteboard with, you know, a bunch of dreadfully bad ideas on it, I said, look, you know, we're not going to be able to just, like, think up this billion dollar idea, like, out of thin air. Like, none of us have been creative for a while now. Like, we need to start creating and then from that, like, we'll get into creative mindset and that's when we'll figure out what to do. So I said, instead of trying to think of big companies, we just need to think up, like, small pain points that we could maybe fix or make things that someone out there might want. And so, uh, I launched a subscription box company, but a subscription box, and it actually started doing really well, I think, like, month three. Month one, we had like 14 subscribers. Month two, we had like 75. Month three, we had like 150. So it was going really well. What was the product the product was for? It was called homebox and it's for expats. Basically every month you get a box of foods. Foods like a magazine, you know, a soft drink from your home country to make you feel at home.
Speaker B: Okay. Is there an f. Afghanistan connection here?
Speaker C: I started with Turkey, actually.
Speaker B: Okay.
Speaker C: And so, like, you know, I found this distributor of Turkish foods, and I packaged a bunch of cheeses and candy bars and Turkish magazine and ship it out every month. But it was a nightmare. I had, you know, food going bad in a storage unit like, I had. It was just a logistics heavy business. And almost immediately I said, I don't want to run a logistics business. So I shut that down. Then I tried to do this shopping app thing that didn't work at all, and so shut that down immediately. And then with truebill, you know, it was just a natural pain point. So, you know, the subscription economy was growing. More and more consumer spending was moving to subscriptions. I don't know if it was me or my brother, but one of us mentioned, like, for me, what happened was I was. I looked at my credit card statement, which I never do often enough, which or which I almost never do rather. And I saw this charge for $40 for inflight wi Fi, and I'm like, oh, man, that sucks. Like, and I started going back in time, looking to see, like, when that. When that appeared, because I certainly, I didn't Fly that month. I didn't recognize the purchase. And I was paying $40 a month for 14 months before I spotted it. And I felt like a huge idiot. And my brother had something similar where he was paying for his home security system in his old house that he'd moved out of. And then my, uh, younger brother also relates something similar. And we said, all right, great. Can we fix this? Can you solve it? So my little brother was like, yeah, I think I could put something together to do this. Plaid had just launched. Plaid is a company that lets you sort of connect people's bank accounts and credit cards and get transactional data. So we built a Plaid connection and built a very simple algorithm that would SC your transactions and find recurring things. And we called it Bill Ninja at the time. And we sent that out to friends and family, and it was pretty cool. It seemed like most of the people we sent it to were finding things that either didn't know they had or had forgotten about or just didn't want anymore.
Speaker B: Can I ask with Bill Ninja, the case of just your engineering brother sitting down and creating an app just to do that, and how long does that take him? Is this like a one week job? Um, and then you're going to send an MVP out to, to friends and family?
Speaker C: Yeah, exactly.
Speaker B: Nice.
Speaker C: You know, it didn't look great. It didn't work great. But it looked and it kind of worked. So, you know, we sent that out and the cool thing was after, you know, two or three weeks, we were getting like 15 to 30 signups a day, which meant that, like, someone out there was sharing it and, like, others were finding it useful.
Speaker B: Interesting. So just within your friends and families, there was referrals happening, right? Yeah.
Speaker C: Yeah.
Speaker B: Okay, so that's enough of a positive sign for you guys to dive further into it?
Speaker C: Well, it was, I mean, you know, we weren't like, okay, let's all, you know, go full time on this. It was more like, this is worth another week or another week or two. Right. So then we added a button to, uh, cancel subscriptions. Because I was like, that seemed the next logical extension was like, okay, it's one thing. Seeing subscriptions wouldn't be great if instead of having to call up and wait on hold, you can just click a button. It gets rid of it for you. And so then, you know, I started spending two hours a day, like on the phone canceling people's subscriptions for him.
Speaker B: Um, I was going to ask, how did you automate? Because I don't think you can just have A button to cancel subscriptions.
Speaker C: Well, now we've built out a ton of automation, but, uh, back then, yeah, it was me, uh, logging into people's things or emailing different services, saying, hi, I'm John Smith's assistant. I need to cancel this. Oh, my gosh, we're just getting on the phone. We did that. I think for me, the real aha moment was I said, look, you know what? The reason we didn't want to go all in on it was I fundamentally didn't think there was a business to be built just tracking canceling subscriptions. And maybe there was. I might have been wrong, but I didn't think so at the time. And so one day, I kind of had an epiphany. I said, you know what? This is not a business built around canceling subscriptions. This is a company around eliminating financial inefficiency in general. And that seemed like it could be a valuable company one day because you think about all the different sources of financial inefficiency, and they can now all fit under this umbrella. So we started adding more things. Like, we added, uh, bank fee refunds, where if your bank charged you a fee, we would reach out to you, like, let's say an overdraft fee or late fee. We would reach out and try to get you a refund, and we're successful a lot of the time.
Speaker B: Did you do that manually as well? Was that like a phone call situation?
Speaker C: No, uh, we found this API that would send a certified letter or. Sorry, send a letter in that case. And so when you got a refund, we would automatically generate a letter and mail it to the bank requesting a refund.
Speaker B: Wow. Okay. Is that. Is that cost effective, or does that cost you? Like, were you running negative to do that?
Speaker C: It cost us 50 cents each time. Postage, plus a few cents. And I'm trying to remember if we. We would charge, like. I think we charged, like, 30% of the refund. And so, uh. But we had people, you know, like, they would get. It was crazy. People would get, like, four overdraft fees in a day. And so, like, you know, you'd see $120 in overdraft fees, and we get all of it refunded. So, you know, it wasn't. It wasn't printing money for us, but it at least covered the cost of postage, right?
Speaker B: Yeah.
Speaker A: Okay.
Speaker C: And we also added bill negotiation where, you know, we could look at your Verizon, your cable, your cell phone bill across dozens of different services and negotiate, like, identify hidden promotions or better rates that were available to you and negotiate those down.
Speaker B: How did you do that at scale? Because again, that sounds like a manual.
Speaker C: Actually had a partner that was doing it for us. And then over time we brought it in house.
Speaker B: Is that something you can do with automation as well, or is that is
Speaker C: not something you can do with automation? That's hundreds of people on hundreds of phones.
Speaker B: Oh my gosh. Okay. Yeah, because I remember researching truebill, I'm in Canada and I don't recall. It's always we get things later. And I'm like, I was thinking the things that truebill does, I'm like, I'm not sure of the behind the scenes mechanics of how this actually works. So, um, I really appreciate you explaining, especially some of the manual aspects of it. Real true startup story, if you're on the phone actually having to cancel subscriptions after that button got hit, I think
Speaker C: that's one of the paradigms that's changed about startups, right? 15, 20 years ago, if you wanted to start a company, you need to spend a lot of money, build a full product, polished product, and then launch it, right? And now, at least for us, we did everything the opposite. So we said, okay, we want to launch subscription cancellation, right? Like, you could easily spend $40 million and build out a huge automation engine to cancel subscriptions. But our thing was like, would people even use this and how can we validate it and is it valuable? And that meant me jumping on the phone and canceling people's newspapers or whatever it was. And so I think for most of the projects we built, we sort of started with like, how could we just get this out there and start getting data on it and then use that to justify the investment of building it properly.
Speaker B: Right? Yeah, and seeing a bit of viral growth. All these encouraging signs too. But I can imagine you still.
Speaker C: All those people never grew virally.
Speaker B: Oh, really?
Speaker C: Yeah, no, it was always, uh, a paid acquisition player.
Speaker B: Oh, okay. Well, I wanted to talk to you about that. But yeah, I, I can imagine you sitting there in those early days when people start hitting the cancel button. You must have been going, ugh, more, you know, because that's how I would have felt, I think.
Speaker C: You know, I had a friend of mine who was working as a, uh, as a temp receptionist somewhere, called her and I was like, hey, how would you like a full time job? He's like, she's like, that's great. I think I said, like, how'd you like a full time job in operations? I don't think I said cancer, but she's like. She's like, yeah, that sounds great. Okay, let me give my two weeks notice. And this is like, Thursday. I'm like, no, I need you to start Monday.
Speaker B: Oh, wow.
Speaker C: And she's like, wow, you're really going to put me in that position? I was like, yes, I am, unfortunately. And so she started Monday and was eventually grew with the company and became like a product manager and everything, but hired a friend to do cancellations and then hired another cancellations person and grew that. And then also in parallel to growing, that team brought on a team of automation engineers to automate it.
Speaker B: Was it all bootstrapped during this entire time, I'm assuming?
Speaker C: No, we went to Y Combinator pretty early on.
Speaker B: Oh, okay.
Speaker C: So we went to Y Combinator, obviously, that's startup incubator on the west coast. And then we pretty quickly raised the seed round. So we ended up doing a seed round of 2.7 million.
Speaker B: Okay. And at that point, were you just doing the cancellations or had you already built the other, like, the negotiation services and things like that?
Speaker C: Negotiations came. If I'm being super specific, we raised 620,000. When we added negotiations, the thing about the seed round is, you know, like, if you've got a really cool company, you can go out and, like, get one investor to give you a $2 million C check, which is awesome. Um, we were not cool enough to do that. It was very hard for us to raise funding.
Speaker A: I find that surprising because you guys had such a good background.
Speaker B: Like, one exit, you had wrapped.
Speaker C: The Series A and the Series B were also just impossibly hard. And even the C was really difficult. You know, we had investors say things like, listen, I love you guys. Literally, if you're doing anything else, I would invest, just not this.
Speaker B: What was the reason for the lack of. Because to me it sounds like, wow, this clearly, especially when I hear you. Hear you say the vision. It's not just a tool to cancel subscriptions. You're right. It's a vision about automating and making more efficient your finances.
Speaker C: Yeah. So at every stage, there was a different list of invest reasons to pass. Um, so at the seed round, it was, this is actually one fund. So I got this fund. It was like the number one, the fund I wanted most. And I'm like, look, we're going like crazy. We're up to 30,000 users already. And he's like, yeah, this is niche. So you're in this niche audience. And, like, you'll get to 30, but you'll never get past 100,000, right? And so I'm like, okay, like, maybe he's right. You know, super smart VC. What can I say? You know, we blew past 100,000. And then I went back and I'm like, look, you know, you said we cap at 100,000 or 250,000. And he's like, yeah, you know, there's definitely more people that want this than I anticipate, but no one's ever going to pay for it. And so then, uh, we went out and monetized, and revenue was going vertical. And I was like, okay, look, people are paying for it. And he's like, yeah, but you're never going to pass. I don't remember what the number was. Like, 5 million run rate. And so we got to 10 million, and I went back and I'm like, look, we doubled that run rate. And he's like, yeah, you did. You proved me wrong every step of the way. I wish I'd invested earlier. Now it's too expensive. So there was a lot of that. Yeah. So our seed round was, you know, it was 2.7 million, but, you know, it was not like a $2 million check. It was cobbled together in checks ranging from, like, 10 to 50,000. And, you know, for over a year, basically, I was going out every week and needing to raise another, you know, 25,000 to keep the company alive for another week. And so I go to a meeting and, you know, they commit 50k, and I'd be like, great, okay, that's two more weeks. We were burning 100k a month, so I was like, okay, that's. That's two more weeks of Runway. And we sort of kept the company alive like that for, I think, about the first two years, almost.
Speaker B: Wow. And you were the, uh, sort of the CEO fundraising role.
Speaker A: Okay, take me back to the marketing.
Speaker B: So you clearly sound like the growth was good, but it wasn't viral. So did you have to, like, is there a brother?
Speaker C: Right. So we launched, we got a bunch of press. We got to, like, you know, 30, 40,000 users pretty quickly. And then it just flatlined. Right. And so we started playing with all sorts of, you know, all these things were like, this thing needs to go viral. You need viral mechanics. So we started playing with referral programs and everything else, and we never got the product to be. To have any type of viral coefficient. And I think the reason is finances are fundamentally shameful and fundamentally private. And even though our user base is not low income, it doesn't skew towards low income. I think People just don't like to say, hey, I found this app that helps me with my money. Because the inherent, you know, I tried to frame it as like, we try to push users to frame it as like, I'm really good with my money and I use this app. But uh, you know, that never really succeeded. And so I think people felt like it's like saying, oh, I found this app that helps with my money is implicitly saying, I'm not good with my money or I'm having money problems, I need apps to help me. Whereas with fitness or food, people like really, really want to share. There's just a natural drive. Like, you know, I have a running app and if I do a good pace or long distance, I definitely share it. Right. But if my bank account gets bigger, I can't share that because that's tacky. And if it's not doing well and the app helps me, I don't want to share that because it's embarrassing that I'm not doing well.
Speaker B: Mhm. Yeah, that makes sense.
Speaker C: So for us it was all about paid acquisition. And what happens with paid acquisition is you go out and you start buying traffic and you spend $100 and you make back 50. Right. And so that doesn't work. And then you make some tweaks to your ads and you make some tweaks to your product and you spend $100 and you start getting back 60, and then you spend $100 to get back $70. And you keep doing this iterative cycle over months and months and then finally one day you spend $100 and you get back $101 and that's when the business just blows open. Not that you would necessarily go out and spend a ton of money there. You actually want a better ratio than that. But at least, you know, you can market profitably. And from there, like a few more tweaks and you can scale and it becomes a game of like, how much money can I spend on marketing? Not, uh, like, how much money can I afford to lose or anything else.
Speaker B: Right. Okay. Is there a brother with like, you know, ad buying skills in there or who?
Speaker C: Well, that was me. I spent five years building an ad tech company.
Speaker B: Okay. And you were, you were in the, in the trenches. All right, so was it a case of Facebook ads, Google Ads, everything? And above?
Speaker C: Beginning it was Facebook ads, but more Instagram than Facebook and Apple search ads. And then over time we grew to, uh, you know, today it's gotta be 50 to 100 channels.
Speaker B: Okay. Was there because I'M trying to think about the timeframe. We're sort of 2015, 16, 17, 18, 18.
Speaker C: Let's say the project really launched at the start of 2016. 2016 was full struggle bus. Uh, I'd say late 2017 was when things started initially clicking.
Speaker B: Okay. Was there like the thought of doing maybe influencer marketing at the time? I don't know if that was common yet, but I would have thought we tested it.
Speaker C: We did affiliate, we did influencer, because
Speaker B: I know the finance YouTube space is quite big, so I would have thought budgeting and so forth.
Speaker C: So there's finance, YouTube, finance, podcasts, all sorts of things. The challenge was, you know, we'd find things that, you know, before Facebook was efficient, meaning when we would lose money on Facebook ads here and there, you'd find an influencer that worked. Right. But it was difficult to find it at scale. So you find an influencer that worked, but you could only spend $100 a week with them. Right. And so it's, it's nice, but it's not moving the needle. And then you're like, okay, well if I go out and find 100 of those, then that's great. But you've got a small team. And the problem is with Facebook, you can go out and you can spend a quarter million dollars a day and the platform has that kind of volume. Right. With influencers, you need a team of people sort of going out, scouting and managing them. And so there's sort of. Facebook's expensive, but it has a ton of scale. But that expensiveness is cost prohibitive in some cases. And then on the influencer side, it's resource prohibitive. If you're the CEO and you're a six person company, you don't have a team of 10 people going out to like scout out and maintain relationships with all these influencers.
Speaker B: Right. I mean, you could use an agency, but, um, I'm guessing even then it's sort of cost prohibitive potentially for the ROI as well.
Speaker C: You know, we tried a few influencer agencies and, you know, they sort of ran into the same problem, which was like, at really small budgets, they could find like, really like specific niche influencers who would work, but then anytime they try to scale, it stops.
Speaker B: Yeah, yeah. It's funny because it's a great way to start a business, but it's not a great way to scale a business. Right.
Speaker C: I think it's similar to PR, right. When you're super early starting your company, PR is great. PR is what took us from like 5,000 to 30,000 users. Right. Over a few weeks. But today, you know, so let's say we get an article on TechCrunch. Right. That would give us, you know, call it 400 users, 400 signups, right. Now if you've got 5,000 signups, you're like, we grew 9% today, that's freaking awesome. Right. Or 8% rather. But today, you know, if we're getting 25,000 signups a day and we get an extra 400 like, and I spend hours of my time pitching TechCrunch to get a hit. I just spent 10 hours to get 400 users. It doesn't scale, doesn't move the needle.
Speaker B: Yeah.
Speaker C: So you know, I know I'm contrarian on this, but you know, I think early stage startups like PR is a strategy, but it's not a long term strategy.
Speaker B: Mhm. And this is why Google and Facebook are such large companies. Right. Because at the end of the day, for a lot of companies, that is the channel for scaling and maintaining scale over time. Right.
Speaker A: So let's talk about monetization.
Speaker B: So I know a little bit of research. You guys were sort of affiliate, like you mentioned before, you were taking a chunk from any of the chargebacks that you could kind of get refunded or the.
Speaker C: And we had affiliate stuff, you know, we point people to get a new credit card or something like that.
Speaker B: Yeah. And correct me if I'm wrong, that was not enough. Long story short, yeah, come close to working.
Speaker C: It was horrible. And unfortunately, uh, you go and you meet with VCs and they say no one's going to pay for this. And at least for me, what I should have done was said I'm going to prove them wrong. But instead I said, they're really smart and I'm going to listen to that. I banged my head against the affiliate wall for a year and a half before even trying premium. I assumed that no one would pay for this and we'd build out launch premium and we'd get a 1 or 2% conversion rate. And it wasn't really until we were on death's doorstep that we tried premium out of desperation. And the conversion rate was way higher than we thought it was going to be. And then we spent a week tuning it and we doubled it again. And that's what sort of saved the business from dying and then just put us on this rocket ship straight up from there.
Speaker B: Wow.
Speaker C: I think over the next four years we didn't have a single down month and I think we had one month in four years. Where we grew less than 5% month over month.
Speaker B: Wow. I feel like the takeaway from this interview is don't listen to VCs. That seems to be a big point.
Speaker A: Can you talk a little bit about
Speaker B: the rollout of premium? Because you've had years as a free service, how do you introduce something like premium? Is it just a case of emailing or putting a box that pops up on the app? How do you roll it out?
Speaker C: The first thing you got to decide is what is premium going to be. And so we said, all right, premium will be. We'll say subscription tracking is free, but cancellation is premium. Bank free refunds are premium. And I think that's what we launched
Speaker B: with, which would have been the two most popular services, I would have thought too, on the app.
Speaker C: Well, they've been to all the services.
Speaker A: Okay, okay.
Speaker C: Yeah, that's what we launched with. And then from there, you know, what we found there was that people will go premium, but they won't stay premium. Right.
Speaker B: Interesting.
Speaker C: You would think I need this really compelling premium offering to get people to go premium. And I don't think that's the case. I think the strength of your premium offering is actually not as correlated to getting premium as you might think. Where it really matters is Churn. So, you know, we started getting pretty decent premium conversion rates pretty quickly, but our premium retention was terrible. Right, Right. You know, it's a lot easier to increase conversion than it is to increase retention because conversion, you know, you redo your premium pop up box or you know, the email telling people to go premium and like, you know, you make that, you can change that email and get 10% better at it. Right. Or that box, you know, you change the button from blue to green and you get a 5% bump. Right. But getting a 5 or 10% increase in conversion is a, uh, hell of a lot of work. Right. Like you have to increase not just your core product and your upfront experience, but like you have to improve the experience that people continue to have with the app over time to get them to stick around for longer.
Speaker B: Right. You mean retention, not conversion. Right?
Speaker C: Yeah.
Speaker B: Right, yeah, yep.
Speaker C: But because we have premium, it sort of changed our North Star. Right. When you're running an affiliate model, that's your revenue, that's your lifeblood, is those affiliate clicks. So whether you like it or not, you're looking your product evolution is partially guided, is too much guided by like, how do I get people to click on a button to get a credit card or to do this thing? Right. And once You've got a premium model, and you're gunning for retention. Your North Star is like, how do I make this product as useful as possible so people keep it. That's just a better paradigm for product development. And so we started saying, okay, what can we add to the app to make the app better? And then for whatever we add to it, what's the free component and what's the premium component?
Speaker A: So what worked?
Speaker B: Because I'm thinking about Churn. It makes sense. Once I've canceled my subscriptions and once I've requested the money back from my bank fees, there's nothing else to pay for.
Speaker C: Right? Well, so then you say, okay, what can I add? Right? And so we said, okay. And no one thing you add is going to be like a magic pill that fixes everything. Right. But we had. Let's say you had budgeting, right? Okay, cool. So budgeting is something that people might continue to come back for, and they say, okay, what's free and what's premium? Well, you know, what we'll do is we'll let people have five categories for free, and if they want more categories or they want to create custom categories, we'll let them go premium. And then we added things like credit scores and credit reports. So we said, okay, people want to track their credit score. That's something that you want to engage with over time to see how it's done trending. Right. So we'll make credit score free and then the full credit report premium. And so we just continued sort of adding features onto the app, and each one building in like a free and, uh, a premium component.
Speaker B: Or as I've heard someone call that stacking. The cool. You just made it better and better and more reason to stay, remember? Yeah.
Speaker A: Since we're getting closer to the end
Speaker B: here, let's go forward to the time you. Well, the recent history where you guys actually were acquired, that was at the start of this year, right. 2022, as we record this right at
Speaker C: the end of 2021.
Speaker A: Okay, so leading up to that, tell
Speaker B: me about where you guys were at. Uh, were you looking to be acquired? Did you just want to keep growing it? Where were you?
Speaker C: You know, so we did our series B, C and D like, six months apart each time. So we did our B. Six months later, we did our C. Six months later, we did our D. Sorry, no. Twelve months later, we did our C six months later, we did our D. And then we had a term sheet for series E six months after that. And it was that unicorn marker. Right? So we had term sheet from a really, really killer fund with a valuation north of a billion. And that's sort of everyone. At least that was always our dream. Over the last bunch of years. You constantly have people kick the tires about an acquisition, but not pull the trigger. But those conversations always end with like, okay, well, maybe we can find a way to get involved, so if you want to do another round, let us know. Maybe we can participate. Or just keep us posted before you do anything big. So we were looking at raising. I wasn't necessarily looking at selling. I thought we were going to raise. So I was out fundraising. And in the midst of that, as word got out, uh, that we were fundraising and I let some people who we'd previously spoken to, I'd reach out and say, hey, heads up, we're going to raise a big round, $100 million. So if you wanted to do something either on the investing side or on the strategic acquisition side, now is the time. Because after that, it's kind of off the table and people perked up. So we were running fundraising conversations and acquisition conversations in tandem. And, you know, the offer came in from, uh, you know, we ended up selling to Rocket Companies, which is known for Rocket Mortgage. And, you know, I think there was a few things that just really made sense about it. Specifically, there was just a ton of alignment in terms of, you know, we had a very clear idea of the vision we were working towards, and they did not want to buy truebill and just, like, absorb it into their product. Like, they were on board with like, continuing that roadmap towards the same mission. And that was really important to us because it didn't feel like we were giving this thing up. It felt like we were joining forces, but also getting the benefits of an exit.
Speaker B: Okay, so if I remember right, you were doing about 100 million run rate towards that time frame when you were maybe being acquired, maybe raising the next round.
Speaker C: We're not quite there, but we're approaching it.
Speaker B: Yeah. Approaching it. Okay. I'm assuming most of that's from premium subscribers to the app.
Speaker C: Uh, the vast majority is from premium, yeah.
Speaker B: Yeah. As a, like, you know, everyone dreams about the exit, especially as a unicorn price tag. And you said that was a big part of your goals for your brothers, too. Were you all on the same sort of page with let's take this exit, or was there a lot of back and forth and pros and cons?
Speaker C: It was certainly not an easy decision. There's a lot that goes into it. Right. One is, you know, start Seeing the zeros and it's hard to, you know, I have a ton of respect to anyone who turns down a multi billion dollar offer. Like you hear about like Zuckerberg or Spiegel turning down, I don't remember under 20 or 30 billion, you're like, holy crap, like the balls on those guys, how did they do that? I wouldn't have like the strength to do it. So that's, I think that's something that once you're there, it's a unique position to be put in that not a lot of people get put in. And it really gives me a ton of respect for the guys who were able to stare down that number and keep going.
Speaker B: And you're coming from a place where you had a company grow really well and then turn to zero. So was there maybe a bit of fear that it could have gone sour or not?
Speaker C: No, I mean the business was just crushing it and uh, I could not see anything disrupting that. And it's continued to crush since the acquisition. I think part of it was this. It's like, okay, so we're worth call 1.3 billion at that point, right? You raise 100 million, that means you're going, hopefully by the end of that you should be worth 3 billion. Right. And then it's like, okay, so at 3 billion, uh, an acquisition, it's not guaranteed to be off the table, but it's probably off the table, you're probably looking harder. Right. And then on the ipo, your ipo, and you know, it's not like you get paid cash. You have stock in this company and the funny thing about it is, since the bulk of your net worth is tied to the company and a lot of the company valuation is tied to you being CEO, you're kind of stuck there. Right. And so I was more okay with that, but I think my brothers were looking at that like, okay, if we take this money, if we fundraise, you know, we're uh, another two years out from an ipo. And then you're signing up for three or four or five years of continuing on as CEO after the ipo. Right. So you're looking at like a seven year commitment. And running a company is fricking stressful. And it's hard and it's scary to sign up for seven more years of um, very nice handcuffs.
Speaker A: Mhm.
Speaker C: So I think that played into it as well.
Speaker B: Okay, and did you guys all stay
Speaker A: on after the acquisition?
Speaker C: Yeah.
Speaker B: I know you raised quite a few rounds. So there was a lot of money to pay Back to the previous investors. But when all that was, you raised 85 million. Okay, well that's not a lot then considering you had a 1.3 billion.
Speaker C: Yeah, exactly.
Speaker B: So you and your brothers all did extremely well. And you could go back to your elder brother who wanted to give back and now he's got a much larger pool of money. So your original claim of not going to the soup kitchen could really come out and was true.
Speaker A: Did your, your guys lives change at all? Like have you done stuff with this money?
Speaker B: I don't know what, what your lifestyle is? You the guy driving around in the sports car or are you still, you
Speaker C: know, it changes a lot, lot less than you think or than I, than I expected. So my brothers live in the same houses they had before and they're, you know, fine houses. Here's what I've realized is even if, let's say I gave you like, you know, a billion dollars, right? Well, if you're still working, you know, you go to the office, you sit at the same desk, Your desk doesn't turn to gold all of a sudden. Right?
Speaker B: Uh, I'm looking at your chair right now. Yeah,
Speaker C: the chair I have is comfortable. You know, you don't. When I picked my chair, I didn't pick it based on budget. I picked the chair I liked. Right. And so you know that let's say you're at the office nine, ten hours a day, right. Doesn't matter if you have a billion dollars in the bank or $100 in the bank, those 10 hours don't change, right. You're sleeping. Let's say you sleep, I don't know, seven, eight hours. Right? Well like that doesn't change. Right. So the amount of time per day that you're actually rich is really small. Right. Like commuting. I'm in New York. It's just quicker for me to go to the office on the subway than like a black car or anything else. Right?
Speaker B: Right.
Speaker C: So, um, I'm still on the subway. Doesn't matter if you have $10 or
Speaker B: a billion dollars on the subway.
Speaker C: It's the same subway, right? Right. Like I still like burritos. Like, you know, let's say, oh, I found this awesome thousand dollar burrito and now I'm eating them, but I'm not. I'm eating st burritos.
Speaker B: Right.
Speaker C: So like very little of your life changes. And I'm sure people that aren't in that situation like disagree with me the same way that I would. Right. I made two big purchases. I bought a sports Car. And I bought a really nice speaker system. Right? I love the speakers. The sports car. You know, the thing is you only get to drive it like an idiot. Like what? 1% of the time, right? Because there's time in traffic where you don't want to get a ticket, right?
Speaker B: Not in New York, that's for sure.
Speaker C: Yeah, well, that's in Miami, but, okay, Miami's dead. So once a month you find, like a windy road without traffic, and you get to enjoy it for like two minutes until you're in at the end of the wind, right? The rest of the time it's actually just more bumpy than a normal car and, like, less. Less comfortable.
Speaker B: Right, right.
Speaker C: Louder. So that's not all that it's cracked up to be. But, you know, these are things that I didn't. And like, I, you know, I thought all of a sudden I'd sell and be 6 inches taller and all sorts of things. And not as much changes as you think.
Speaker B: So, I mean, reveal as much as you like with this, but where do you keep all that money? Is it like, obviously you have been able to spend it on stupid things. Is it just sitting in stocks and bonds and gold and so on, or how do you invest?
Speaker C: Well, firstly, you have someone who's helping you with it, right? So the instant the announcement goes out, your phone starts blowing up and your inbox starts blowing up from JP Morgan and UBS and Merrill lynch and everyone else, right? So, so you get help. But there really is a crash course in figuring out, okay, what the heck am I going to do with this? One, how am I going to make it impactful? Because you want to do some things for others. And then two is, what is my macro view of where the world is going and how do I bet on that? But managing it, it does take a fair amount of mindshare.
Speaker A: Oh, really?
Speaker B: Okay, so you actually are thinking about, do I put it in bitcoin, do I put it in something else? Or what's the ratios?
Speaker C: Uh, well, that or so you do a rough matrix and you say, OK, 20% of it should be. Or x percent should be in real estate. X percent should be in stocks, x percent bonds, y percent in angel investments, z percent in private equity. Right? And then you gotta kind of evaluate all that. And it does take work.
Speaker A: We only have a couple minutes left. So first of all, anything you want
Speaker B: to shout out to the audience, like, obviously, now it's at, uh, Racket, where truebill exists. And that's where they go download Rocket Money.
Speaker C: We rebranded App to racket Money.
Speaker B: Racket money.
Speaker C: Do genuinely, strongly believe it is the best app, um, out there for your finances, regardless of income level. It's funny because for lower income people, if it can save you 30 bucks a month, that's meaningful. Right. And then for higher income people, it's just shocking how much financial inefficiency you allow because your time becomes. You start getting other demands on your time that are just more, more pressing than saving yourself 20 bucks here or there. Right. And so if there's an app that can sort of do all that housekeeping for you, it's actually pretty beneficial.
Speaker B: Yeah, yeah, I totally agree. Pressing a button is a whole lot easier than making a phone call and wasting your time at the bank or whatever. So what's next for you?
Speaker A: Are you planning on seeing it out where you are now and is there
Speaker B: another company in you or what's going to happen?
Speaker C: So there's definitely some products that are either in the works or at least ideated that I want to see through and I want to be there for us to launch. And so that's the next period of time and then after that, if you ask me right now, yeah, I'm dying to start a company, but, uh, when I left Nannigans, I was dying to get a job in ad tech. And I was out interviewing and I met this guy from the MIT Media Lab and he told me something really helpful. He said, whatever you do, give yourself a few months. He's like, you've been looking at the world through this super narrow lens for the last five years. Because I spent five years in ad tech in Nanigans. He said, just so. He's like, so anything you think about doing next right now is going to be viewed through that narrow lens. He's like, just spend a few months, broaden your perspective and just explore and then decide what you want to do. So, uh, though I don't necessarily want to take six months off now or it's not a desire. I think if and when my time at Rocket kind of comes to a close, take six months and then decide what I want to do next. But if you ask me today, yeah, I'm itching to start a company.
Speaker B: Okay, well, we'll look out for it then at some point.
Speaker A: Thanks for your time. Really appreciate going deep into your full story.
Speaker B: And that was great.
Speaker C: Yeah, thank you so much.
Speaker A: I hope you enjoyed that interview with Yaya Moktarzada. M. I had a lot of fun doing that one. I love the billion dollar stories. I always pay Extra attention to what is the difference between a company that you know can do well, make a million dollars a year, 2, 5, 10, but the companies get to 100 million plus in terms of run rate, how much revenue they make and that valuation of over a billion dollars. Those are unique.
Speaker B: That's why they're called unicorns.
Speaker A: So I always love to have a chance to speak to a unicorn founder, especially a CEO as Yaya is, and just hear what was it, what was the business model, what was the marketing, what was the initial test idea and rolling out new features and how do they turn on their premium pricing in this case with truebill. So lots of really cool insights. If you also love insights like this, I invite you to look at the back catalog of Vested Capital. There are other billion dollar founders as well as lots of other entreprene in the back catalog and some people who work more in other forms of investing. There's some M real estate investors, some crypto people, crypto startups, some online marketing. Lots of different types of entrepreneurs are in the back catalog of uh, Vested capital. And you can get them all right now for free just by subscribing to Vested Capital. Wherever you get your podcasts or going to my blog at Yaro Blog, hit the podcast tab and you'll be taken
Speaker B: to the archive of all the episodes
Speaker A: of Vested Capital and and the 50 plus episodes of my previous podcast called the Yarrow Podcast and before that the Entrepreneur's Journey podcast. So all the episodes that are there are available for free for you to dive into the archives. One last plug too. The sponsor for today's episode is my company Inbox. Done. It is an email management executive assistant service that basically provides a human being. In fact, we give you two human beings who will take over managing and replying to emails as well as keeping you up to date on all the most important things you need to know about. Whether it's scheduling, your calendar, letting you know about important clients, opportunities that hit your inbox, anything you think that's vital and critical that you don't want to miss out on that gets into your inbox, your assistants will make sure you know about it and they'll keep everything else away from you. So all those things that are basic to do, lists, time suck, tasks that don't move the needle forward for your business or your life. Your assistants will handle that. Your assistants will reply to those emails for you, manage those conversations, keep things going without you being involved whatsoever. They also work with your team, work with any existing software that you use within your company. And we have over four years now, plus, in fact, we're pretty much over five years now of running this company, servicing all kinds of clients, whether you're a real estate agent, a venture capitalist, an online coach, you own a retail store. We're working with pretty much anyone who has too much email. So if that's you, head to inboxdone.com and book a discovery call. We'd love to talk to you and, uh, possibly work with you to get you free from that inbox. Okay, that's it from me. My name is Yarrow. Thank you for listening to this episode of Vested Capital, and I'll talk to you on the next episode very soon. Bye.
Speaker B: Bye.
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