

Ashkan “Ash” Karbas Fruchan explains how he bootstrapped WatchMojo from 2006 to a ~26M-subscriber YouTube channel, the legal/strategy bets behind its “Top 10” format, the personal debt required to survive the “dark years,” and how that experience shaped his later bid to bring MLB’s Montreal Expos back.
Born in Iran; father worked for the Spanish embassy. Family moved to Spain, then Montreal. Finance degree (1999) during dot-com/9-11 downturn. Worked many jobs including bank customer service, early search engine “Mama,” and men’s site AskMen (he owned ~2%); later founded WatchMojo with a wife/cofounder.
He avoided raising investors for ~15 years; relied on DMCA takedown rules and fair use; treated YouTube as a “revolution” in quality/celebrity; used second mortgages and didn’t fire staff; turned down offers (e.g., ~$64M cash) to protect team and deal terms.
WatchMojo started with ~$250k in 2006; ~1M losses; paid himself ~$32k/year; second mortgage signed with his wife; sold 25% in 2020 for $90M CAD (net worth estimated $100–$250M).
Written by AI. May contain mistakes.
Explaining the concept behind the Moneywise podcast and the Hampton community.
“What they made, what they spend, what they own, and the stuff they'd never post about online.”
A detailed introduction to Ashkan, his background, and his journey.
“He graduated with a finance degree in 1999, which he'll tell us a little bit more is the worst timing possible for a finance degree for Ash.”
Ash discusses his path to entrepreneurship and the challenges he faced.
“Today, I have a very special guest, Ash Kan.”
Ash shares insights about his childhood and family financial background.
“The question is you as an entrepreneur, how do you make it inevitable?”
Discussion on Ash's various jobs and the moment he decided to start his own venture.
“And I saw a LinkedIn post you had written at one point where you had 31 jobs.”
Ash describes the decision-making process and vision behind starting WatchMojo.
“And I worked at a tech company, a search engine.”
Exploring Ash's financial gains from previous ventures and their implications.
“But before that, you had some amount of stake in Ask Min when it sold to IGN, right?”
Ash reflects on the early days of YouTube and the creation of WatchMojo.
“A lot of people skip this in startup stories.”
Explore the shifts in media and the importance of focus in content creation.
“So, you know, the best investor, but also entrepreneur is a social scientist.”
Learn about the challenges faced while building a content company in the early days of YouTube.
“But like our four big bets, YouTube lists, relying on fair use, and the whole pop culture, geek culture vertical.”
Discover the financial hurdles and the importance of support from family in entrepreneurship.
“And I'm not being stereotypical, but I've always said like a condition of success as an entrepreneur is a supportive spouse.”
Exploration of the growth and evolution of the business from inception to peak revenue.
“But I also understood that it was revolutionary because of things like TrueView, skippable ads, you know, and it was like revolutionary because of many other things.”
Discussion on building a strong team and company culture during growth.
“Like you're hiring bright young kids who, unfortunately, because of many reasons, don't have that many options.”
Insights on the decision-making process regarding acquisition offers and company valuation.
“let's go out there and recruit from those companies.”
Discussion on balancing growth with sustainability and avoiding pitfalls in business.
“I'm saying it wasn't the three and a half.”
Explanation of EBITDA and how it affects business valuation during negotiations.
“And also I'm in finance, so I could point to the, it's not like an emotional baby.”
Reflections on how the pandemic affected business operations and growth strategies.
“And then not a mistake because it worked out.”
Learn about the valuation journey of a company from initial offers to a successful deal.
“It was like, again, it was like, you know, the numbers were matching our best years, but it was also showing that like, yes, when we reinvest, we can grow again.”
Discover how personal wealth is managed and the importance of investing wisely.
“What was the deal amount that you struck?”
Explore the decisions around real estate investment and lifestyle management after a big financial win.
“And that was like back to back investments or how long was that time period?”
Understand how achieving financial security impacts mindset and decision-making.
“I call it, I don't care, which is the extent of how crude I will be.”
Gain insights on perseverance, investment strategies, and the importance of knowing your worth.
“I want to bring the plane in for a landing and ask you, what is one thing about your money that you typically just don't share with people?”

Get the gist, explore an idea or ask about something said.
On Moneywise, what are the key points of this episode?
Automatic transcript. May contain errors.
0:00Ashkan Karbasfrooshan: Ash built one of the biggest channels on YouTube, almost 26 million subscribers, and he did it without raising a dollar for almost 15 years. Then the offers started showing up. One of them was$64 million in cash. He said no. By the end of this episode, you'll know what that cost him and what he's worth now. And I'm not really sure if he knows whether saying no was the right call. I'm Daniel Burke, and this is Moneywise. Every episode, I sit down with one founder or exited founder and go through their actual money.
0:27Moneywise Hosts: What they made, what they spend, what they own, and the stuff they'd never post about online.
0:32Ashkan Karbasfrooshan: Some quick context on why people even tell me this stuff. Money Wise is a Hampton show. Hampton is a private community for founders, and it's full of people who already talk real numbers with each other behind closed doors. So when they sit down here on Money Wise, they'll say that number out loud with me on the show. And that's the whole deal. You come to the show, you talk about your spend, your net worth, all the ways that you really have your personal finance broken down. We know that personal finance is so much more personal than it is finance. That's what this show is about. My guest today is Ashkan Karbas Fruchan.
1:00Ashkan Karbasfrooshan: He goes by Ash. He was born in Iran, and his dad worked for the Spanish embassy there. And after the revolution, the family went to Spain, then Montreal. He graduated with a finance degree in 1999, which he'll tell us a little bit more is the worst timing possible for a finance degree for Ash. And so then he ended up working a bunch of jobs. Bank customer service, early search engine called Mama, then a men's site called Ask Men, where he wrote, sold, and did interviews. Really, whatever needed to be done. He owned about 2 % of Askman when it sold, and that check became his whole starting bankroll.
1:30Ashkan Karbasfrooshan: He tells you the exact number. In 2006, he put roughly$250 ,000 of his own dollars into WatchMojo. If you've ever watched a top 10 video on YouTube, there's a decent chance it was theirs. Today, it's close to 26 million subscribers and something like 18 billion views. The reason I wanted Ash on the show is to figure out how he paid for all of this. There was no investors, and six years before the company made actual money, he was in the red. a second mortgage on his house. He paid himself$32 ,000 a year. Then around 2017, with a company worth something like$80 million on paper, he started turning down offers.
2:02Ashkan Karbasfrooshan: And today he's trying to bring Major League Baseball back to Montreal with the Montreal Expos. Ash goes over a lot of the details of his story. He'll get through Hurst, Hugh Hefner, Donald Rumsfeld in about 90 seconds. I'm going to jump in a few times with context because I think it's just going to help you understand some of the story, some of the complexities, and understand a little bit more about what makes Ash, Ash. Welcome back to another episode of Money Wise. Today, I have a very special guest, Ash Kan. He goes by Ash, and he told me I can say Ash to introduce him. So I'm going to do that.
2:32Ashkan Karbasfrooshan: Thanks so much for joining Money Wise today, Ash. Thank you for having me. Can you, for just 60 seconds, give me a quick rundown of what you're trying to do with the Montreal Expos?
2:40Moneywise Hosts: Sure. So in today's era of sports ownership, it's no longer just one like multi-billionaire that writes the check. It is usually like, yeah, there is an anchor investor and then you have like a private equity or two. You might have like a strategic. And so I've spent the last 298 days lining up all of the ingredients. And after 100 days, we address capital. And then the second thing that MLB cares about is a stadium. So right now I'm just literally like looking around for land that is fair to everybody, that is like close to downtown, that could fit a stadium and like a district for entertainment.
3:13Moneywise Hosts: and then MLB to wrap it up, MLB ultimately cares about the size of the market and Montreal, given its history, legacy and all that, if I could.
3:21Ashkan Karbasfrooshan: Well, next pose, we're in the MLB up until 2006, if I'm not mistaken. So it's not, it's not, okay. 2004, it's not an unheard of idea. It's really bringing back what already existed. Yeah.
3:32Moneywise Hosts: And I think what they just want to see is you have the ownership and you have a stadium that befits, you know, baseball. Exactly. And that's what I've been working on. And I would say after two, I mean, it's funny, the parallels of WatchMojo starting with a clean slate, nothing, people thinking you're crazy, good luck with that business pal. They always believed in you, buddy. I'll say this, entrepreneurship literally is living a few years of your life like few people can or want so that you could then live your life the way few people can, right? So that's, it's just, it's a trade-off between satisfaction today versus satisfaction in the future.
4:12Ashkan Karbasfrooshan: And then ultimately though, I think, yeah,
4:14Moneywise Hosts: like my favorite line now is just, there's no limit to what you could accomplish if you don't let others set the barrier and the ceiling for you. So when I started WatchMojo and when I started the Expos, a lot of people thought it was impossible. I said, no, it's improbable. The question is you as an entrepreneur, how do you make it inevitable?
4:32Ashkan Karbasfrooshan: Ash, I was digging into your background. It looks like you were born in Iran, lived in Spain for a while, and now you're in Montreal. I'm curious, what was money like in your household growing up?
4:44Moneywise Hosts: that's a great question and it's all relative you know my dad um came from a large family but his mom passed away when he was two and his dad 15 so he really like his definition of sacrifice uh just for survival was very different than like mine um but he also then you know was pretty successful and was supporting his siblings um you know but it wasn't like he came from this like super wealthy family you know the first ones that fled uh when the revolution uh happened in 79 my mom's family overall was maybe a bit like also well off but her dad died when she was seven or eight um so neither were like you know uh wealthy in any sense and then when we came you know we left i'm very lucky because my dad worked for the spanish embassy even though he was iranian and it's Iran, not Iran, but that's okay.
5:44Moneywise Hosts: It's fine. But so we were very lucky. Thank you for that. No, it's fine. It's all good. There's a great Matt TV skit, but let's move on. But so he worked for the Spanish embassy and the Spaniards were kind of grateful for his service post-revolution. So they're like, you can go anywhere you want, if you want to work at a consulate or embassy anywhere. And he looked at many places, but he wanted to be an entrepreneur. He didn't want to work as a diplomat. And he wanted to come to North America and he wanted us to speak French. So he said the only place that's really going to be possible is Montreal.
6:17Moneywise Hosts: And then growing up, I would describe us as like middle, upper class, meaning obviously relative to a lot of my classmates early on, we were fine. You know, we had a decent house. We had a decent car. No, not at all like wealthy. But, you know, I always look at it as even this myth of like the self-made man, which is a myth. Like, okay, I didn't inherit Watchmill Joe. I didn't have a wealthy uncle. But, you know, without my dad, without my older brother at a period when, you know, he was, I was in college and I lived with him and many other things, you know, everybody stands on somebody's shoulder.
6:52Moneywise Hosts: So money, I would say, you know, there was enough where we had a roof on our head, food, but yeah, not like that. It was plentiful where, you know, we traveled opulently or anything like that, but it's relative to me. I always felt like the richest, luckiest kid in the world.
7:10Ashkan Karbasfrooshan: Okay. That's helpful. And I saw a LinkedIn post you had written at one point where you had 31 jobs. And I'm curious at what point, well, correct me if I'm wrong, right? No, no, it's true. Was it 31 jobs?
7:22Moneywise Hosts: No, no, no. Well, it's like one of those jobs could have been like interviewer. You know, I interviewed Joe Montaigne. That's fine. But it was like when I worked at a job where I was also the VP of sales guy, you know? So, yeah. Yeah, but yeah, if you count waiter, customer service rep, as I was enumerating -
7:39Ashkan Karbasfrooshan: Most people would count those. Yeah, well, they were definitely jobs, right?
7:42Moneywise Hosts: But I mean, I didn't have 31. I had 31 rolls. Like I wore 31 hats.
7:49Ashkan Karbasfrooshan: When in that journey did you decide, I got to start something of my own here?
7:57Moneywise Hosts: So I was a reluctant entrepreneur. at best. I had developed into the, in my twenties as an intrapreneur. Um, so I joined an online men's magazine called ask, but so let's go with when I was in school, I actually studied finance, even though I was more interested in history psychology, I, I, I stayed in business and finance because of optionality, which is really critical as an entrepreneur, right? So business finance just gave me more career paths to pursue. But the reality was that I graduated in 99. The dot-com bubble burst, NASDAQ crash, 9-11, Ashcan Carbos Roushan. Wall Street is not rolling out the carpet for anybody named Ashcan Carbos Roushan.
8:39Moneywise Hosts: Born Muslim, you could be as secular atheist as you are. You know, I'm a white male straight guy, so I'm not claiming prejudice. But yeah, trust me, if you start your career, then. So I had to pivot. So I wanted to go in consulting or banking. It wasn't going to happen. I was working at the bank in customer service. one of those 31 jobs. And it became clear, a paradox, that when you're really good at something, sometimes you're like shackled. So the bank said, look, we're not going to transfer you to like our version of Goldman Sachs or our version of Morgan Stanley or Merrill Lynch. You're going to stay here.
9:16Moneywise Hosts: And I didn't mind. I was loyal. But I said, OK, that means I got to change. And so then I kind of just went straight into the startup world. And I worked at a tech company, a search engine. And this was before Google had started to totally eat up the market.
9:31Ashkan Karbasfrooshan: That was AskMen?
9:32Moneywise Hosts: No, this was Mama. So Mama was a meta search. It was one of the first handful of search engines that started in the late 90s. So at Mama, I realized I love the startup world, but I felt tech was two zero sum. And I felt that to win, sometimes you had to either cut corners or be a bit too like abrasive to staff or, you know, like - Were you burned by tech at some point or what
9:57Ashkan Karbasfrooshan: brought about some of that conviction?
9:59Moneywise Hosts: No, I wasn't burned by tech in that sense. I just realized that, you know, I was more of a writer. I was a storyteller. You know, I studied finance, but I never grew up reading books, but I was like, yeah, I read a lot. And I had this insane amount of knowledge and information that I thought everybody had, but that was just because I was a curious kid reading encyclopedias and a lot of magazines. But so after Mama, I went to Ask Men and Ask Men is where I found my voice. I started to write. I worked in sales partnerships, a bit of everything, interviewer, had a great five-year run. But that's where I said, you know what?
10:31Moneywise Hosts: My boss is fine. Okay. He has his flaws. Everybody has his flaws. But I said, if you really, really want to treat stakeholders, like we talk about stakeholder management or servant leadership. But I was like, if you really, really believe that, and it's not just a tag, a hashtag or like a buzzword, then you really do need to be the decider. And if you want to be the decider, if you're not going to inherit your dad's business, if you don't have an uncle to give you a check to go do something, you got to become an entrepreneur. So I was really not an entrepreneur, an intrapreneur, a reluctant entrepreneur, but I'm also a bit big on numbers.
11:05Moneywise Hosts: So I was like, Hugh Hefner started Playboy at 27. Like there's a lot of stories of like entrepreneurs at 27, and just got and married, no kids at the time. And I said, you know what? There's this revolution brewing called like YouTube and online video. And I said, I think I have the skill set to build a world-class business.
11:23Ashkan Karbasfrooshan: And I want to hear more about the world-class business with WatchMojo. But before that, you had some amount of stake in Ask Min when it sold to IGN, right? And then that sold to News Corp. Tell me what you personally made from that and what that structure and payout looked like.
11:40Moneywise Hosts: Sure. So I own 2 point something percent. Only quotation. It was still not bad because the company only had 500 ,000 of seed funding. So that company got acquired for about 15 million, one five, not huge. And my pay cut was like, literally, I remember the check in USD, 282 ,500. I went to the law firm, got a check. That's a good check right there. Not a bad, but the thing was, again, life is relative, right? Like this glass, is it half full or half empty? It's up to you to look. But so that was not like enough to do many things, especially in New York or San Fran, even in 2005. But to me, it was ample.
12:18Moneywise Hosts: To me, I was like, you know what? I could be like a Swiss Army C-level CEO, CFO, CRO, culture, HR, partnership, you know, janitor, bottle washer. And then I'll just hire basically people who have a skill set that I don't have. So I basically made like a quarter million there. And then, yes, we got options. So then when a few months later, News Corp, Fox, Interactive Media bought IGN, I got probably like, I want to say another$150 ,000. So, you know, with about less than half a million Canadian, and then there was not a lot of taxes because we had capital gains tax exemptions. So, you know, it was to me ample, you know.
12:57Moneywise Hosts: And I really had started to, even though I was, everybody's insecure with one way or another, even though I was pretty confident, you know, I won't lie. I was like, I have no idea what I'm doing, but you ultimately have to bet on yourself.
13:08Ashkan Karbasfrooshan: Ash owned about 2 % of a company that sold for around$15 million, and his check was$282 ,500. A few months later, News Corp bought IGN for$650 million, and his options paid out roughly another$150 ,000. A lot of people skip this in startup stories. His first exit was under half a million Canadian all in, and he treated it like a seed round that he wrote himself. Sometimes the exits that people get in early stage startups are not as big as you'd expect them to be, particularly when the headline is hundreds of millions of dollars. Yeah. And I mean, at the time, let's call it a quarter million. You're 27 years old if I did my math right.
13:43Ashkan Karbasfrooshan: And YouTube is still sort of like no man's land. No one knew what it was, really. There was probably a couple thousand videos on it at that point. I mean, you out of the blue decided I'm going to start doing YouTube videos. I'd love for you to tell me that story. What about it at that time enticed you to start this now dynasty, if you call it that, of WatchMojo?
14:06Moneywise Hosts: So, you know, the best investor, but also entrepreneur is a social scientist. You know, they do look at trends. They do look at history, psychology, sociology. So already by now in the 2000s, I had a good five years of experience working online, but I had like 10 years of experience just studying business. You know, I was a bit like, you know, before chat GPT, there was an Ash GPT. Like I really just would read business week sports. I mean, I read business week, like people read sports illustrated. I read them both. You know, I would read fortune, the economist, you know, imagine you're like 18, 19 bored on the subway going to school.
14:40Moneywise Hosts: And I would be reading like the financial times. Right. I mean, it was kind of a, it wasn't normal in that sense. And I just thought it was interesting. I thought companies were teams. I thought executives were athletes. You know, it was kind of like, that's how I looked at it. But anyway, so mid-2000s, even though I was like a prolific writer, you know, and ironically, I was probably one of the most well-read writers in the early 2000s, just because Ask Men would syndicate content to MSN and AOL, two of the biggest portals. But so recognizing all of that, I said, you know what? Let's be honest, to quote Jack Welsh, if you're not going to be number one or number two in a market, get the hell out.
15:12Moneywise Hosts: and I was like I'm not going to reinvent the wheel and build a world-class media company around text and articles but I said there is this revolution and it's wild wild west it's kind of like burning the boats I said just you have no plan b your goal is not to build like a gawker you know or like a Conde Nast your goal is kind of like figuring out what the next MTV or ESPN looks like I was sitting in New York at a bar with an exec from Hearst, and incidentally, Vice's Shane Smith, they both said the same thing. They're like, it's impressive what you've built, but you're all over the place. We're having beers, and I remember vividly eating chips at the bar.
15:51Moneywise Hosts: And I was like, what do you mean? And he was like, you're all over the place. He's like, how the hell do I know what to expect from this brand if you got pet videos, and the next day you got Batman? That scenes.
16:01Ashkan Karbasfrooshan: Okay, picture YouTube in 2006. It's barely a year old and it's mostly pirated TV clips. Google buys it that October for$1.65 billion. And a few months later, Viacom sues them for a billion dollars. Two legal things matter for the rest of Ash's story. So here's the fast version. The DMCA is a 1998 law. It says a site like YouTube isn't automatically on the hook for what users upload as long as it takes stuff down when the owner complains. Without that, YouTube probably doesn't exist. Fair use is what lets you show short clips of a movie or a show if you're commenting on it, reviewing it, or ranking it.
16:33Ashkan Karbasfrooshan: These are your typical reaction videos. Watch Mojo's whole top 10 format lives on fair use. Every Batman clip in one of those videos is Ash betting the law Holt. In this episode, he talks about those laws like both you and I already know them. I didn't, and so I looked them up, and now we do.
16:48Moneywise Hosts: And I was like, but we focus on video. He's like, no, no, no, no, no. You know, as he's like tossing back pines. He's like, no. In media, focus means automotive, fashion and style, travel. He's like, that's how advertisers think. And I was like, yeah, but that world is shifting. I said, because of programmatic, because of audience targeting, I was kind of skating to where the puck was, but I came back to Montreal and literally to quote Donald Rumsfeld, I was like, you don't go to war with the army you want. You go to war with the army you have. And I looked around, I said, I know what our strengths are.
17:20Moneywise Hosts: And I said, we're not going to out authenticate, you know, like the grandma from Italy was making an amazing lasagna. We could go Italian chef to come here and make it. It won't pass the sniff test. That yaya is going to kill us. That nonna, her sauce is not comparable to ours. And so I was like, let's skate away from user-generated beauty tips. That 16-year-old girl or that 22-year-old guy that's showing you how to cough. And I was like, that's where the world is going. We're not going to compete with UGC. So the team was like, uh-oh. I said then, I kind of process of elimination. But I also said, yes, we are all very passionate about movies, TV shows, music, sports.
18:03Moneywise Hosts: But we're also good at it because I said ultimately WatchMojo is like a think tank. It's like a research group. You know, like I myself being finance trained, I'm an analyst, right? So we make mistakes. Humans make mistakes. But our focus is to get things right. And I start off by saying the best investor and entrepreneur is a social scientist. the main epiphany was not just that YouTube was going to do to everything what the internet did to TV and what cable did to network. I just said, look, the bottom line, yeah, okay, I joke that top 10 commandments, Moses, everybody's always like the good list.
18:38Moneywise Hosts: But it was more that I understood that, you know, geek culture was going to overtake pop culture. It was very clear to me that the kids that were reading comic books were now ruling Madison Avenue, Silicon Valley, Hollywood, and Wall Street. So I was like, oh wait, Bob Iger is now buying Lucas Pixar Marvel. So again, you got to as an entrepreneur look for these signals and patterns. So I was like, well, they're not buying the Star Wars franchise to bury it in the back, like next to my own. They're going to double down on this and this will become really, really mainstream. So we were already covering all this, right?
19:17Moneywise Hosts: So it wasn't so much that we -
19:18Ashkan Karbasfrooshan: And that started in 2006.
19:20Moneywise Hosts: Yeah, 2006. But like our four big bets, YouTube lists, relying on fair use, and the whole pop culture, geek culture vertical.
19:29Ashkan Karbasfrooshan: Yeah.
19:30Moneywise Hosts: That was probably 2011 and 12. And it's also because we had exhausted a lot of stuff. We had done bios and profiles of A-list and B-list actor. But at some point, we were like, you know, doing the life and times of Pee Wee Herman. God rest his soul. But my point was top tens was really something we gravitated to. We were always doing it. We doubled down on it. And then, yeah, then from 2012 onwards, we caught lightning in a bottle. And, you know, then we had our hockey growth stick years.
19:58Ashkan Karbasfrooshan: And let's talk about the lightning in a bottle. I was reviewing your P &L ahead of the call. And, you know, it looked like cumulative losses of about 820K by 2011. And so early years were, I would call them the dark years. I mean, I would love for you to kind of walk through. it sounds like you took a second mortgage at some point. How deep did the hole actually get before you started seeing a massive return on this big bet you took?
20:24Moneywise Hosts: I was in China. I was digging. I was like, why am I on the other side of the earth? No, I mean, look, so if you do the basic back of the napkin math, I had about$250 ,000. And yeah, we racked up. I think the number was like 850 or like, let's just say a million in losses. So the balance -
20:41Ashkan Karbasfrooshan: And were you fully bootstrapped from that? Fully bootstrapped. Fully bootstrapped.
20:45Moneywise Hosts: Like I literally took, you know, let's say I sold, like I used$50 ,000 of cash, which was liquid. But then I sold$200 ,000 of not just stocks. In Canada, your 401ks are RRSPs, which if you get penalized, oh, I went through those. And then I went out and I took a mortgage. And that's the funny part in my mindset. The thought of like firing the team never crossed my mind. You know, it was kind of like, you know, when you're a quarterback, you got two minutes to come up with a win. You're never thinking I'm going to take a knee. Like, you're like, how do I get in the end zone? Am I going to run it?
21:20Moneywise Hosts: Am I going to throw it? I will eat this ball to get it in the end zone. So I think in hindsight, yeah, I'm just not wired that way. So it was just like to me, it was like, yeah, obviously I'll go get a mortgage. And then, yeah, what happened basically, I also didn't pay myself. To me, I never considered giving up. It was more, I won't lie, I'm in a hole. and I'm so in debt and I'm personally liable for it that if I give up, then I'm forever indebted. You know, even if I -
21:47Ashkan Karbasfrooshan: Giving up is not even an option.
21:49Moneywise Hosts: So yeah, it was like giving up was like, you know, death almost. So then I was like, no, no, we'll just go at it now. It's funny. I literally would sleep every night, wake up dreading and fearing payroll. You know, I even purposely made payroll. I mean, it was the same salary, but I made payroll twice a month. So 24 times instead of every two weeks, 26 times, because I wanted those two less -
22:16Ashkan Karbasfrooshan: Tiny bit of extra runaway.
22:17Moneywise Hosts: I just wanted like 24 anxiety incidences and not 26. No, that's as ridiculous as it was.
22:25Ashkan Karbasfrooshan: And second mortgage, we hear this term thrown around all the time. We're talking a literal second mortgage. I would love for you to walk me through. Like I was going to be homeless.
22:33Moneywise Hosts: I had this nightmare scenario where I -
22:35Ashkan Karbasfrooshan: So it was the second mortgage.
22:36Moneywise Hosts: So the second mortgage -
22:37Ashkan Karbasfrooshan: Like how many months of runway did that buy?
22:40Moneywise Hosts: Look, there was so many. Like in the end, it was like late 2000s, so 2009 or even maybe 2011. I think it might've been 2011, the second hurrah. It was like, I remember sitting at some notary and going like, this is a scene. If they ever like fictionalized, say like the social network, like social network was Facebook. but let's say if somebody wanted the YouTube story and I'm developing, it's called Countdown and through like a fictionalized version of WatchMojo. But my point is I was like, there's going to be a scene where there's this guy signing away and you don't know if he ends up homeless or makes it, let's say.
23:16Moneywise Hosts: And I remember going, my wife, who was one of the co-founders, I was like, what a saint because most spouses are like, honey, why aren't we taking a trip? Where's my ring? And I'm not being stereotypical, but I've always said like a condition of success as an entrepreneur is a supportive spouse. But so the second mortgage was a bit like the equivalent of like a float, meaning it was like more of like a debt facility, you know, like an extra credit
23:43Ashkan Karbasfrooshan: because by then we had revenue.
23:46Moneywise Hosts: Okay. And the main thing I want people at all, like an entrepreneur to be like, never give up. This is it. No, I was in a, in an environment where like the macro fundamentals were all headwinds.
23:58Ashkan Karbasfrooshan: I love this moment that he talks about his wife because I personally think that nothing I do in life would work without my amazing wife. And he talks about a second mortgage and a spouse who signed next to him at the notary. Inside Hampton, that type of stuff gets talked about all the time because in Hampton, there's a room full of people who have also signed those papers and many of them have spouses or partners just like that. A lot of this show starts as conversations long before they ever become an episode. And if that's the type of room that you resonate with, highly recommend going to check out Hampton at joinhampton.com.
24:28Moneywise Hosts: Well, Andy, you were kind of doing something
24:29Ashkan Karbasfrooshan: that hadn't been done. There was no playbook. Someone goes and wants to start a million dollar YouTube channel right now, there's a playbook. There's a playbook, yeah. You go, you look at who's done it, you talk to the people who've done it 10 times, you go and do it. Obviously, I'm oversimplifying, but in 2006, this had never been done before. So you were creating something from scratch.
24:49Moneywise Hosts: Absolutely. When I would be writing for TechCrunch about startups, financing, and for media posts about advertising and the world of publishing and all that, I wrote an article like 2010 saying YouTube has gone from the pariah to the bell of the ball. In 2020, when COVID was happening, the LA Times wrote an article with the exact same headline. The exact. Like I have it. I posted this. I'm not like I told you so. Just more for people to understand. Sometimes you as an entrepreneur think you're late, but you're really early. And you want to be like a little bit early. You don't want to be so far early.
25:25Moneywise Hosts: Like Quibi and Jeff Katzenberg.
25:27Ashkan Karbasfrooshan: you know there was a lot of structural rest in peace quibi quibi but quibi i watched one show on quibi and there you go because you weren't on a train you weren't going anywhere you were at a
25:37Moneywise Hosts: home you're like that's right yeah you're like this terrible timing terrible timing for a for an eight out of ten idea yeah well so but but so timing is a big part of it but uh yeah by the time that last mortgage came you know like i kind of knew we would eventually be successful but it was like every time i thought we're at the end of the tunnel the oncoming light was really just an oncoming train.
25:58Ashkan Karbasfrooshan: It was just - Well, and eventually the growth curve did start. I mean, by 2011, you were profitable doing, I think, 35K in profit. I mean, what was the first year where the numbers were just stupid? I mean, I know you eventually went from five to six to seven figures in profit. And now today, I would love to hear kind of the breakdown.
26:18Moneywise Hosts: Sure, sure. So the thing is, YouTube is disruptive for many reasons. Like Netflix is evolutionary because it changes like the user experience. It's convenient, but it's not, I stopped short always of calling it revolutionaries for the simple reason that it's the same programming. It's long form scripted, you know, shot like this. You got a director, a showrunner. It became even more bloated. And I love Netflix. I'm a shareholder. I mean, this is not a knock, but it kind of wanted to disrupt, but that was evolutionary. With YouTube on the consumer side, it was like revolutionary because it changed the definition of quality.
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28:06Moneywise Hosts: But I also understood that it was revolutionary because of things like TrueView, skippable ads, you know, and it was like revolutionary because of many other things. so for us it was like a godsend because i didn't need to hire like 20 sales people
28:20Ashkan Karbasfrooshan: you know i didn't need the cost basis didn't go up at the same rate as actual revenue and profit what was what was revenue let's say 2012 for example no so i think what happened was like
28:31Moneywise Hosts: looking at the the table we went like you know 800 but then it was like a million three million five million ten million or eight million ten million and then it kept growing after oh and And then we, okay, before we'll call it, you know, company life stages. We've gone through four full cycles. We have to avoid debt, but that's part of it. If you're like an entrepreneur, that is part of it, right? But so in those years from 2012 to 2016, we were still hiring quite a bit. Like we went from less than 10 people to like 50, 60 people, but it wasn't like we were bringing in until 2016, like the super duper expensive C-level types.
29:11Moneywise Hosts: It was young people who, frankly, did not have a lot of options. And we were giving full-time jobs, employment status. It's not like we're hiding coders who get like a gazillion dollar signing. Like you're hiring bright young kids who, unfortunately, because of many reasons, don't have that many options. So if you just create a good culture and you treat them respectfully and you give them like stable jobs, stable income, paid vacation, health, like you could recruit the cream of the crop, right? So that wasn't hard. but because our revenue blew up we didn't even have time to go like invest at the same commensurate rate so like one year we had like 60 70 80 percent like EBITDA margins right it was just like our yeah yeah it was like it was but false modesty aside that was because i was like your whatever you would pay a ceo cfo a council like that was you were hiring executives yeah i was basically and i was i still paying myself like not a lot of money right it was like mid-2000s where i was like
30:09Ashkan Karbasfrooshan: oh you could pay yourself what were you paying yourself let's say uh let's say 20 2019 right before you i believe you sold a minority then i was paying myself still below like i wasn't a
30:20Moneywise Hosts: higher gun ceo i was paying myself a fair rate but let's start i was paying myself on the books the first five six years 32 000 but not even deducting sorry and then i was deducting benefits to keep it kosher and legal with the government but i wasn't steady salary 32 32 32 32 it didn't go off. And then it was like 40, 60, 50. And then I was probably like at a hundred. It was like never crazy salaries. Like to be honest with you, I didn't. Because Montreal is not that expensive to be candid. And I'm not like flashy and we could talk about that. I'm sure you want to dig in. But what ended up changing the profile of the company was, yes, I joked, we want to go from being the Montreal Expos, we now think we're the New York Yankees.
31:02Moneywise Hosts: So I went out and I started to recruit. I felt like I had developed my team quite a bit, but even I myself, you're always coachable. You could learn, your team can learn. So I was like, you know what? If we want to build the next MTV, let's go out there and recruit from those companies. So we brought like a chief operating officer from like, let's say Time Warner. We brought in like a chief revenue officer from like The Onion. We brought in like a CMO who had worked at Digitas and all these like amazing people. I love them. If I see them, like I don't burn bridges with anybody. So, but after two, three years, oh and i by at this point i hired them after turning down 80 90 million dollar valuation lois
31:42Ashkan Karbasfrooshan: so when i said why i mean through this time what what's going through your head of 80 90 million
31:48Moneywise Hosts: offers why not so so as in 2012 below a dallas-based company wanted to buy us before we took off like our rocket chambers they offered three and a half million plus like an earn out of six. So like three and a half could be 10. I was going to accept it because I'm not driven by greed. At that point, I was like, I just need a partner. And I was like, these big Americans who have the big ambition. So let me ask a question there.
32:17Ashkan Karbasfrooshan: Not driven by greed. I believe you, but you're wearing five, six executive hats.
32:24Moneywise Hosts: But that's out of necessity. But it was out of necessity.
32:26Ashkan Karbasfrooshan: But you had to have been, it had to have been some type of appeal to, oh, I can stop doing this and get$80 million out of it, that'd be pretty appetizing though.
32:35Moneywise Hosts: But let's explain. Let's explain. So in 2011, I'm like super indebted. It's relative. It's like a gas water in the desert. I'm saying it wasn't the three and a half. It was the change in setting. If I now go and become some VP at B-Low, watch World Joe become some unit, there's guaranteed employment for my team because we're not a big team. What are you going to go lay off? I could no longer do 10 roles. I know what I'm like the Michael Jordan. Yeah. What I'm really good at. So that was like a positive. Now think of what happened from 2012 and then they got acquired by Gannett. So I got a call one day and they're like, we're not going to move forward.
33:14Moneywise Hosts: And I was relieved because I knew that this hockey stick period was coming, but I didn't want to be greedy and stupid knowing finally I have a home for myself, for the team. Now for five, six years, the company, this isn't the number, but let's say the company generates$50 million in EBITDA. It was probably a bit lower, but it was still a sizable number that I was like, okay, you pay taxes, you pay this, you pay that. You're good. So now all of a sudden when people came and they're like 40 million, 50 million, 60 million, it's just the number, you know, like it's a bit like, yes, as a quarterback, you want to win the Super Bowl.
33:48Moneywise Hosts: You want to throw 50 TDs. You want to terrorize like you're the safety, you know, don't dare, you know, like try to stop this ball. I'm going to expose you, but you just want to win. You care about that. So to me, it was no longer about the money, but I was not enjoying it. You know, like I was just like, go, go, go, go, go, go. Now, 2016, 17, after a decade, my third book is called The Ten Year Overnight Success, because all success, overnight success, a decade in the making. It's as if like the world woke up that there was this well-run professional media company on YouTube that they could acquire.
34:25Moneywise Hosts: Not like a Mr. Beast or PewDiePie where, okay, without him, what are you buying? so we went from like not really having a lot of interest to always having a lot of interest but not everybody really getting over the fair use or usually just content frankly so all of a sudden we had like you know it started one company called me they said we want to acquire you then another one then i would like i literally and how what are the numbers they're giving you 100 million 200 million so the numbers no the numbers and this will use multiples and then you could just it would just so like the multiples would usually start off with like let's say oh you know like six, eight times, but we always commanded 10 times EBITDA.
35:02Moneywise Hosts: And also I'm in finance, so I could point to the, it's not like an emotional baby. We're worth a billion. It's like, well, we're this multiple because of these reasons. And I taught.
35:11Ashkan Karbasfrooshan: So six, eight times EBITDA at what valuation in let's say 2016?
35:16Moneywise Hosts: So let's go now to what happened in 2017. 2017, when we started the year, let's say we were at four or five billion of EBITDA. And then as the year crept up, we were growing quite a bit. So at one point, a big fund in Canada wanted to invest. And I think they wanted to invest 25 % at like a 75 million valuation. They were great. Still talk to them, no ill feelings. And then at the same time, we had the largest media company in Canada wanting to buy us and their CEO and myself kind of hit it off, developed a bit of a bromance because he used to run, And he used to run Universal Music Canada. So like he and his team, they kind of found Shania Twain, Brian Adams, Justin Bieber, The Weeknd.
36:03Moneywise Hosts: So for me, it was interesting. He was like, when I was asking him, like, well, why do you want to? He was like, look, he's like, I definitely like WatchMojo and like what you've built on YouTube. We need digital. But he was like you. He's like, you're an animal. He's like, in a good way. He's like, you're a machine. He's like, we'd love for you to come and help us figure out a lot of these stuff because we have a ton of assets, but we need like your energy. We need the way you see the future. And that was great. And one day he called me and he was like, yeah, you know, we'd like to buy you at 10 times 8 EBITDA, which was our trailing 12 month.
36:34Moneywise Hosts: And he was like$80 million, but we'll buy 80%.
36:38Ashkan Karbasfrooshan: People like Ash throw around EBITDA in these episodes all the time. Many of the listeners likely know what EBITDA is, earnings before interest, taxes, depreciation and amortization. But I wanted to just break it down anyways. Think of it as the cash the business throws off in a year before the bank and the accountants take their cut. When someone buys a company like WatchMojo, they usually pay a multiple of that number, EBITDA. Ash says buyers would open at six to eight times and he held out for 10. So 8 million times 10 is 80 million. It's that simple.
37:04Moneywise Hosts: So again, I'm like 64 million cash of clothes. It's a good outcome. You've done this now for 11 years. Don't be greedy. And then not a mistake because it worked out. But I was like trying to please the media company and the local investor and effectively kind of build a menage a trois, for lack of a better word, where I could not decline either of these two behemoths in my backyard. I've turned down these paper offers in the 70, 80, 90 million valuations. Now, I've saved a bit of money, so don't worry about me.
37:40Ashkan Karbasfrooshan: But you did sell some portion of it in 2020. And for how much?
37:46Moneywise Hosts: I'll get that. But here's what happened in those four years. We invested so much, and I was like a drunk sailor at a bar saying yes to everything, every expansion, every event, every initiative. Our EBITDA fell by more than half. So all of a sudden, whereas we were being valued in like the five to eight EBITDA at a 10 multiple, all of a sudden your revenue is hitting a wall because everything after a few years of growth eventually matures and it can decline. You have to avoid that. But now we were not growing hockey curve. So our multiples fell and our EBITDA was down. So when I would have conversations, people were no longer floating the 100 million range, they were like 30, 40, 50, whatever, 60.
38:33Moneywise Hosts: Like the numbers, understandably as a finance guy, I wasn't like, this was crazy. I was like, yeah, I get it. And it was hard because a lot of people now were in my ears saying, why did you turn it down? Why did you turn it down? Those initial deals.
38:49Ashkan Karbasfrooshan: Why did you turn it down?
38:50Moneywise Hosts: Well, because I felt in one, if the media buyer at the time wanted to buy 55 % and get a call option to buy the rest, but not issue me a put option to sell them the rest. And as much as I think they're a great company and they're not a dinosaur, but they view themselves as like old legacy. I said their tendency is there is a chance they kill this business. Like they could take a bunch of money losing departments, put it under ours to make the numbers look better. All of a sudden our EBITDA falls artificially because of the losses in their other divisions. And then they come like, now we're going to buy you.
39:28Moneywise Hosts: So I knew like not being a novice, I understood like how deal making works. It wasn't greed. It was just like, well, I didn't kill myself to save my team for you guys to come a year later, financial engineer us into, you know, destitute and fire my team. Yep. So I like I was just like, give me a fair deal. But and it wasn't that they were acted in bad faith at all. It was just it made sense to walk away. Like, that's the beauty of.
39:53Ashkan Karbasfrooshan: So then eventually to move along to the numbers, what ended up happening in 2020? And then what majority stake you own today? How much is that worth? Where does that bring your actual net worth today? Liquid and illiquid.
40:08Moneywise Hosts: So after the period where we went down, we in 2018-19 had embarked on this initiative called WatchMojo WM 2020, like 2020 vision, but also where we want to be in 2020. There was a lot of investments that reduced our EBITDA, but a number of those paid off. One was the MissMojo channel, one was our channels on Snap. so we could see that our revenues were starting to grow again, which is the key if you want to come in.
40:39Ashkan Karbasfrooshan: To what? What was revenue at that time?
40:41Moneywise Hosts: Well, revenue now was getting back to where it was. So whatever it was. What? It was like if we had like, I'm not around. Let's say if we had hit 10, 11, 12, because we were always high margin. It wasn't like our revenue.
40:53Ashkan Karbasfrooshan: So 12, let's call it 12 million. Yeah.
40:56Moneywise Hosts: But let's say it was always flat, then all of a sudden it was like we could see it was going to start growing again. You could just see the metrics and the momentum. But so we in that moment got an offer to sell for like 30, 40 million to Ziff Davis. When COVID hit, obviously it was ironic because for a decade, everybody was in my ear saying, what about copyright risk? What about platform risk? These are all real risks. And in the end, knock on wood, none of those things happen. So as entrepreneurs, you worry about stuff that usually doesn't even happen. But then there was this externality, a pandemic, which tragically affected like half the world, hospitality, travel, leisure.
41:33Moneywise Hosts: So all of a sudden, private equity had half the targets to go invest in. So one day, we're now again crushing it and our numbers are back to where they were in the 2016 range and growing very quickly. Which was like the five to eight of EBITDA over like 10%. 1012 of revenue and not flat revenue or two or three million of EBITDA. It was like, again, it was like, you know, the numbers were matching our best years, but it was also showing that like, yes, when we reinvest, we can grow again. So I got a call from one of my advisors and formal named Peter Horan, former CEO of ask.com, about.com, briefly president of answers.com.
42:20Moneywise Hosts: And he was advising a PE fund called Star Mountain Capital started by a Canadian. and it's funny all of their like managing partners had worked like the u.s offices of like canadian banks so they kind of understood canadian culture and all that as well yeah and we chatted from like june of 2020 and same thing it was always basically at about a 10 times ebda so that deal and i'll tell you was uh we valued us at 90 million canadian so even higher than those offers we had received like in 2017 from the others. Now, what made the difference, even though I absolutely did not need the money is, and people are going to go, yeah, sure.
43:06Moneywise Hosts: But I'll tell you, I had built a really, really good team, you know, VP of finance control, you know, like it was a good system, but I was like, if God forbid tomorrow I get hit by a bus, yeah, payroll will be made, but there's no real like ongoing true succession planning. Like I I could have a CEO in mind, but I'm like the CEO, the secretary, the CFO, the, you know, the, it's just, I go, there's way too much concentration from a governance and administrative sense on me. So fine, we'll make payroll because it's automated. But in a year, who's filing our statements? You know, I go, I, okay, I have like heirs, but like, they're not going to run it.
43:49Moneywise Hosts: And then I was like, yeah, that would suck, you know? And I go, I am really alone because if there's an externality where like Donald Trump goes, I'm shutting down YouTube. Yeah, that would affect us. Right. So when the P came, I explained that to them. I said, look, you tell me what you're like, not deal breakers, but like what your parameters are. I'm not going to waste your time. Enumerate what you look for. If they would have come a bit like Vice and TPG or TVQ, whatever, and been like, we want a 3X liquidation preference and we need that. I would have been like, thank you. Bravo. Go elsewhere.
44:27Moneywise Hosts: So we struck what was a fair deal. Like I could have in peak COVID gone out and sold a stake for like 150, 200 million because there was just nowhere to put money.
44:40Ashkan Karbasfrooshan: What was the deal amount that you struck?
44:42Moneywise Hosts: The deal amount was$90 million. We sold 25%. And you made personally what that day? Well, I owned 90 % of the business.
44:51Ashkan Karbasfrooshan: So you made$80 million.
44:53Moneywise Hosts: Well, no, but I didn't sell. This is the difference between net worth. I sold 25 % of the business.
44:59Ashkan Karbasfrooshan: You sold 25%. I thought you sold 80%.
45:01Moneywise Hosts: No, no, no.
45:02Ashkan Karbasfrooshan: So where does that bring your net worth today?
45:04Moneywise Hosts: My net worth could be anywhere, if you include my investments, from$100 to$250 million.
45:09Ashkan Karbasfrooshan: And what is that in? Is that mostly in public stocks?
45:12Moneywise Hosts: Yeah. So basically I had started - Break that down for me.
45:15Ashkan Karbasfrooshan: What's the pie? What percent is in public stocks? We're going to get there.
45:18Moneywise Hosts: So my stock portfolio, there is, let's say if the stock portfolio is 100%, one third of the equity, public equity is managed by the pros, exactly where it should be. Banking, retail, some mine plants that I -
45:35Ashkan Karbasfrooshan: Conservative long holds. Conservative, boring, like kill me, but safe.
45:41Moneywise Hosts: So that has not appreciated the way my portfolio has, but it also, like it was a 10. That's fine. You know, in 22.
45:48Ashkan Karbasfrooshan: And then what about the other two thirds?
45:50Moneywise Hosts: The two thirds, yeah, that's public stock, which I manage and, you know, like crowds.
45:55Ashkan Karbasfrooshan: And you're calling that a hundred million in public stock?
45:58Moneywise Hosts: The combination, the combination with other liquid stuff that I have, that would be that stuff.
46:04Ashkan Karbasfrooshan: And let's talk about your monthly spend and your burn and what that comes out to. What are you using your money for in a day-to-day life?
46:13Moneywise Hosts: I remember watching Scott Galloway go on and he's like, I spent$400 ,000. And I was like, brother, more power to you. That's crazy. So this is not the video where something goes viral because I'm a prolific spender. My lifestyle is pretty chill. So my monthly expenses are like whatever. I mean, the only expensive thing I did after the deal, I sat down with my wife and I said, look, I go, you're very smart. You didn't study finance. So let me just explain the rationale. I said, we have a beautiful house. We paid it off. It's like in a great. How much was your house? No, the first one was like Montreal is very cheap.
46:48Moneywise Hosts: Whatever numbers I throw out is batched. Like I bought a house for. I'm just curious. No, like the house that I bought in 2011 was maybe like$600 ,000. dollars. But that house was the neighbor.
46:59Ashkan Karbasfrooshan: And the house you're in now.
47:01Moneywise Hosts: Slightly more. I don't, I don't mind the ballpark, but the point is that house was 800, but it needed TLC. But all I had was, you know, with a mortgage. But then when we started to make money, the first thing I did was just pay off the mortgage because I didn't really like a mortgage. So that house was paid off. I didn't have a driveway or a garage. And during COVID working from home, I was getting tickets and I could see my daughters were like teenagers. I was like, okay, we need maybe another bathroom. So I sat down with my wife. I said, look, I go, we literally just transacted. We have this cash that I have to deploy.
47:31Moneywise Hosts: Like we'll pay our taxes and this and that, but I have to deploy. So I said, I'm going to invest in some startups, but that's like pissing money away because it's illiquid. Most of them go to zero. How many did you invest in? I invested in a lot because I wanted to help entrepreneurs. Let's say - Like five? No, 15. I invested in 15 startups.
47:50Ashkan Karbasfrooshan: I invested in - Total money toward that approximately?
47:55Moneywise Hosts: five million, not a insane number.
47:57Ashkan Karbasfrooshan: And that was like back to back investments or how long was that time period?
48:02Moneywise Hosts: So my private is like 15 companies of which five have probably died or should die. Power law in effect, five that are still managing and doing okay. And five that are doing really, really well. And then, but I also invested in five, um, like investors, you know, like, uh, you know, uh, you know, just people starting their first fund and me being like, like, okay, why not? Because I wanted to see if investing through building a fund-to-funds approach. And then I invested in a handful of pre-IPO SPVs, just to, again, understand, as I was doing the public. And I love working with entrepreneurs, but that has proved more frustrating because I realized I am a pretty good operator and a pretty good problem solver.
48:44Moneywise Hosts: And if you just write a check, random example, 2%, 200 ,000, what impact do you really have? That's good for people that really just are like passive. Anyway. But so I sat down with my wife and I said, we now have like a large sum of cash, which is liquid. And I got to figure out what to do with it. And I know what I want to do with it. But before I said, it would be really, really smart because we retained 70 % of WatchMojo and that's a digital media company. Look at what COVID did. You know, I use the Donald Trump shuts down YouTube example. I said, we should have more exposure in a different asset, such as real estate.
49:24Moneywise Hosts: I said, I don't think you or I want to be like some slumlord owning a number of, you know, that's not who we are. And I can't, like the second your toilet breaks, I can't fix my toilet. I would be there with a wrench, you know, so it's just, it's not really, I'm not wired that way.
49:38Ashkan Karbasfrooshan: But I said,
49:39Moneywise Hosts: why don't we just buy a bigger house with the driveway in a nicer neighborhood? And then that house, if random example, if our first house was worth 600 ,000 or whatever, could be worth 10 times more or three times more or whatever more, but let's buy that cash, never have to worry. But if whatever happens, if there's like a nuclear strike on all YouTube infrastructure, and hopefully that doesn't happen, you have a house that's paid off for, right? And still have all your stock and all that. But otherwise, nothing opulent. Sure, maybe you travel, you don't necessarily think twice about that first flight that's earliest, that's like$40 cheaper.
50:21Moneywise Hosts: And it's a reminder every day of your privilege and your hard work. But I also realized at a point that I'm like, yeah, if you're not like going to be splurging, and you know, you're already going to leave your kids a decent size, then you just start to kind of not sweat it. And to me, first of all, I hate the term F you money. I call it, I don't care, which is the extent of how crude I will be. But like, to me, the benefits of I don't care money is you can take your time.
50:47Ashkan Karbasfrooshan: Do you feel like the acquisition in 2020 for 25 % was life changing for you? Or was it just another day in your journey? Did it make you happy?
50:57Moneywise Hosts: It was mindset changing and it took time. It wasn't overnight. You know, like when you're like the difference between frugality and cheapness is there's many, but frugality at most, it affects you like, Oh, I'll take that early flight. I'll pick the middle seat instead of business class. You know, cheap is your decisions affect others and it harms. Right. So like, I'm always been like, you know, I mortgage my place or I don't think anybody would accuse me of that. But you yourself as an entrepreneur, if you're not like a third generation wealthy guy who wakes up with like, you know, eating caviar and you think that's like the default mode, it is hard for you to change and go, Hey, wait, like I'm not the same guy who was struggling with payroll.
51:37Moneywise Hosts: I'm not the same guy that had to use a cash advance to pay my mortgage or whatever, you know? So more mindset changing than life changing.
51:44Ashkan Karbasfrooshan: I understand that. That's a good response. I want to bring the plane in for a landing and ask you, what is one thing about your money that you typically just don't share with people?
51:54Moneywise Hosts: That's a good question. I mean, everything I've said on this call are things I usually don't share you know like i i legit only took after five years i even referenced the pe deal because i didn't want people like as a distraction being like oh this guy's coming asking us for money because he's like struggling you know um and now with the expos um it's more just showing people that like yeah you don't have to be necessarily the person with the ultimate solution but if you can help reach the desired outcome, you should, right? That's a good question. I mean, look, I'm a pretty transparent person, but I would say everything I said on this interview were usually the things that I didn't share, you know?
52:44Ashkan Karbasfrooshan: Yeah, well, I appreciate that. And the Montreal Expos acquisition, you know, bidding, whatever you want to call it, that's an interesting part. That's exciting. well, I'll be keeping my eyes peeled for a potential MLB team joining from just north of us on the East Coast. And good luck to you, Ash. Thanks for joining Money Wise. Everything about Ash's story says don't quit. He has a second mortgage and he didn't quit. Personally on the hook for the debt, not quitting. No plan B. And for him, it worked. But there's a study from the 70s by a researcher named Barry Stahl. He had business students make investment calls and the people who poured the most money back into a losing project were the
53:20Moneywise Hosts: ones personally responsible for the first bad decision that the project had.
53:24Ashkan Karbasfrooshan: The short story in that sense is that being on the hook makes you double down. Sometimes that's grit and sometimes it's just not wanting to admit that you are the one on the hook and that you're trying to really get past that to make your story a success story. There's another study from the 80s. About 3 ,000 new business owners were asked their odds of success.
53:42Moneywise Hosts: 81 % said 7 out of 10 or better, but a Third, said 10 out of 10.
53:47Ashkan Karbasfrooshan: Ash knows this, and it comes out in the way that he talks about his story and really about continuing to double down because there was no other choice. My read is the lesson isn't just to never quit. It's know why you're not quitting. Ash had been writing publicly for years about where YouTube was going before anyone understood what he was talking about or agreed with him. Ash had a very good read on the market. So if you own a business, take 10 minutes this week, pull your last 12 months of profit, multiply it by a boring multiple, then write down the price where you'd say yes on the phone. Then write down what would have to happen for that number to get cut in half.
54:21Ashkan Karbasfrooshan: For Ash, it was one expensive year of hiring. If an offer ever comes in above your number, you want to have already made the decision back when you were calm whether or not you're going to accept the offer at that number. If you want the other side of this, watch my episode with Tebow. He took a deal, sold for$8 million, and then tells me he regrets it. If he were to go back and do it all over again, he wouldn't sell. Ash, on the other hand, didn't sell and watches the offers drop. Between the two of them, you get the entire problem and a lot of what we deal with on this show. Last thing, if you run a company doing at least$3 million in revenue, and you want to be in the room where founders talk through stuff like what Ash is talking about before they ever get onto a show like this, that is Hampton.
54:59Ashkan Karbasfrooshan: It's where this show comes from, and it's where a lot of these conversations happen before they're on Money Wise. Go check it out at joinhampton.com. Thanks, as always, for listening to Money Wise. If you got this far, please go ahead and hit subscribe, and I will see you next week. Thanks again. Thank you.
We're still surprised people did this but... 50+ founders worth $10M to $4B reveal their personal finances. Here it is: https://joinhampton.com/mw-wr
Why do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.
He took a second mortgage to keep WatchMojo alive. Today he's worth over $100M and is trying to buy a baseball team.
Ashkan Karbasfrooshan is the founder and CEO of WatchMojo, one of the largest media companies ever built on YouTube. He started it in 2006 with a $282,500 check from the AskMen sale, racked up roughly $1M in losses by 2011, sold his retirement savings, took a second mortgage, and paid himself $32,000 a year for the first five years. Then the top-10 format hit, revenue went from $1M to $10M+ in a few years with EBITDA margins as high as 80%, and he turned down offers at $75M, $80M, and $90M valuations. In 2020 he sold 25% to Star Mountain Capital at a $90M CAD valuation. He still owns most of the company, and puts his net worth between $100M and $250M.
This episode gets into what it's like to sign a second mortgage at a notary with no idea if you'll end up homeless, why he moved payroll to twice a month just to have two fewer panic attacks a year, the real reason he walked away from an $80M offer (it wasn't greed), and how saying yes to everything cut his EBITDA in half. We also go deep on how he actually invests now — $5M across 15 startups, two-thirds of his stock portfolio self-managed — why he still takes the $40-cheaper flight, and his current mission to bring the Montreal Expos back to MLB.
Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you are a founder, apply here: http://joinhampton.com/mw
Timestamps:
00:00 — Ash's background: born in Iran, raised in Montreal, and why "the self-made man is a myth"
02:50 — 31 jobs and the reluctant entrepreneur: "Wall Street is not rolling out the carpet for anybody named Ashkan"
07:03 — The AskMen exit: a $282,500 check at 27, plus ~$150K when News Corp bought IGN
09:18 — Why he bet on YouTube in 2006: "You don't go to war with the army you want, you go to war with the army you have"
14:23 — The dark years: $1M in losses, selling his RRSPs, and the second mortgage
16:14 — "I made payroll twice a month instead of every two weeks because I wanted 24 anxiety incidences, not 26"
18:24 — Being early vs. being too early (and the Quibi problem)
20:37 — The hockey stick: $1M → $3M → $5M → $10M revenue, 67-80% EBITDA margins
23:25 — Paying himself $32K a year for the first five years
24:59 — The 2012 offer he almost took ($3.5M + earn-out) and why he was relieved it fell through
28:32 — Turning down $75M, $80M, and $90M valuations in 2017
30:36 — "I was like a drunk sailor at a bar saying yes to everything" — EBITDA falls by half
31:39 — Why walking away wasn't greed: the call-option trap he saw coming
32:58 — The 2020 deal: selling 25% to Star Mountain Capital at $90M CAD
37:54 — Net worth reveal: "anywhere from 100 to 250 million"
39:03 — Monthly spend, paying off the house, and $5M into 15 startups
43:37 — Was the deal life-changing? "More mindset changing than life changing"
44:34 — What he never shares about money
45:34 — The Montreal Expos comeback plan: "It's not impossible, it's improbable"
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