CC020: bootstrapping the world’s largest real estate community to over 1m members // a Coffee Chat with Josh Dorkin (BiggerPockets)

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Josh Dorkin 0:00

I one day went to my wife, I was in tears. It was year eight of the business. And I was like, we’re done. This is over, I’m shutting it down. I could not leave. I couldn’t go anywhere and I couldn’t do anything. I built the business up to such a level that it truly required probably eight to 10 people, but I was doing all those jobs.

Jay Clouse 0:22
The startup investment landscape is changing. and world class companies are being built outside of Silicon Valley. We find them, talk with them and discuss the upside of investing in them.

Welcome to upside.

Hello, hello. Hello, and welcome to the upside podcast the first podcast finding upside outside of Silicon Valley. I’m Jay Clouse and I’m accompanied by my co host, not co-producer himself, Eric Hornung.

Eric Hornung 1:02
I thought we came up with a alternative title for me since I am not the co-producer of this show.

Jay Clouse 1:07
What’s the title for someone who’s in apprenticeship?

Eric Hornung 1:10
executive producer. That’s what we’ll go with.

Jay Clouse 1:12
AH, I don’t know about that. I think executive producer’s top of the hill.

Eric Hornung 1:16
Yeah, that’s fine. It’s like, Hey, I don’t do all the dirty work. But I still get the producer title assistant producer. I think co producer sounds kind of nice. Because I don’t really produce anything where photos spelled FA UX.

Jay Clouse 1:28
You could at least transfer your own files.

Eric Hornung 1:30
I did transfer my own files, like two weeks ago.

Jay Clouse 1:34
That one time. Well, we share a lot of titles in this effort, Eric, but producer is not one of them.

Eric Hornung 1:41
No, it’s yours, man. It’s all you do I get any of my own titles or everything I have just co

Jay Clouse 1:46
you could be head researcher, head mathematician.

Eric Hornung 1:50
And those are like the lamest titles.

Jay Clouse 1:52
Chief mathematician. Now the lamest title is CFA.

And you’ll have that soon enough.

Eric Hornung 2:00
Thanks, man.

Jay Clouse 2:02
Let’s so let’s Oh, you know I had a secondary nickname

Eric Hornung 2:05
you had to you had two nicknames for one episode. I had a hard time choosing Did you know which one you were going with when you started saying hello? Hello. Hello? I did. I’ll give you a little insight into my noggin. Often I don’t really have a nickname when I start saying hello. Hello. Hello. And by the time I get to Mr. I just whatever’s there kind of comes out.

Jay Clouse 2:26
I got so excited about this one that I forgot to add the Mr. In the title. Yeah,

Eric Hornung 2:31
I heard that. You also kind of sprinted through the opening. It was a whole there’s a whole different cadence.

Jay Clouse 2:37
I don’t know it was a sprint but it was a different inflection. I was like let’s mix it up. Let’s make it a little bit more friendly. Nothing wrong with that. The other Title I thought about going with was Mr. Smaller Pockets himself.

Eric Hornung 2:46
Are you calling me poor?

Jay Clouse 2:49
No, but you rent.

Eric Hornung 2:51
I do rent. I have a guest bedroom that we don’t rent out to anyone. So I’m probably spending too much money on rent. that’s a that’s a good point.

Jay Clouse 2:59
That’s okay, I am the beneficiary of that guest bedroom from time to time and I appreciate it.

Eric Hornung 3:04
Yeah, so far, like two nights a year, which is definitely worth the increase in right. You’re welcome Jay do we get to write that off as a business six months by the way?

Jay Clouse 3:10
We do not.

Eric Hornung 3:11
okay.

Jay Clouse 3:12
Are you consolidating our books that you’ve been doing the day of the month? No, no, you haven’t.

Eric Hornung 3:16
I didn’t get the title of CFO.

Jay Clouse 3:19
you volunteered to do that work though.

Eric Hornung 3:21
That’s true. I really should get titles before I volunteer to do stuff. Yep. And you’re paying for the software. I am paying for the software. Man. I guess I know what I’ll be doing after this recording.

Jay Clouse 3:29
Love it. Our guest today is Mr. BiggerPockets himself, Josh Dorkin. BiggerPockets is the nation’s largest and most active real estate investing social network designed to simplify and enhance networking, dealmaking data valuation, education, marketing and transactions for investors, consumers and professionals. Josh is the founder of BiggerPockets, formerly CEO of BiggerPockets, which was founded in 2004. And he lives in Denver, Colorado,

Eric Hornung 3:55
I found out about BiggerPockets through our friends who we actually do know, I’m just gonna start calling everyone our friends, even if we don’t know them. But we we did meet in Omaha Preston Pysh of the investors podcast. And that was the first podcast I really started listening to when I graduated college. And Josh happened to be on that podcast and how I found BiggerPockets. And I ripped through. You know, I think it was like 150 episodes in a couple weeks, and I was hooked. And I really enjoy what they’re doing over there.

Jay Clouse 4:27
Yeah, I’ve just started listening to it full disclosure, but you were the one that brought it to my attention. I thought BiggerPockets was just a podcast, which started in 2013. But come to find out that the company itself started in 2004, and was really moving along and humming by the time they had the podcast started. So excited to hear about the retrospective from Josh in this. The podcast itself is one of the top investing podcasts. If you look at iTunes, and search for upside, we’re in the investing category. It’ll say top investing podcasts. And it’s in the top five there, I think, the top 150 podcasts overall on iTunes. So really awesome to have Josh on the show today.

Eric Hornung 5:05
What’s our angle here? Why is Josh on? I mean, it’s cool. He’s a big name. He’s someone who I’ve come to know as like a virtual mentor. But how does he fit into upside?

Jay Clouse 5:14
Well, a couple of ways. One, you know, we love to explore the fringes. And I wouldn’t say that real estate is necessarily the fringes of investing, but it’s a little bit of a fringe for our show here. He also bootstrapped BiggerPockets, which is something that we’ve taken an interest in here as of late on the show, and at the level of scale they are now it’ll be fun to talk about what bootstrapping a business like that looks like.

Eric Hornung 5:37
I guess it’s worth it to just mention that we found Josh. Well, we told you how I first heard about him. But we found Josh for this specific interview, after we published our earnest capital episode. And on Twitter, we were interacting and Josh kind of popped in talking about founders and entrepreneurs. And somehow through the magic of Twitter, Joshua up in our inbox.

Jay Clouse 6:01
love it. So if you guys aren’t joining the party with us here on Twitter yet, you can go to at upside FM join in on the episode releases and the conversation there would love to hear from you. As we go through this interview. If you have any thoughts on the show, you can tweet at us at upside FM. Or if you have something a little more longer form or private. You can email us hello@upside.fm. I’ll get to that interview with Josh right after this.

David Sherry 6:23
Hey, what’s up everyone? This is David from the new money podcast where we discuss investing opportunities for everyday people. If you’re interested in startups in tech, each episode of new money show explores a different financial product or opportunity that anyone can invest in. These are websites and apps like betterment and wealth front and acorns, the types of companies you’ve heard even advertised on podcasts like these, we break down the pros, cons and trends that we see emerging in this new world of FinTech in bite size shows that you can listen to every week. So just search new money in your podcast player and you can tune in. Thanks

Jay Clouse 7:00
Josh, welcome to the show.

Josh Dorkin 7:02
So nice to be here guys.

Eric Hornung 7:03
Really cool having you on having listened to over 150 episodes of the BiggerPockets podcast and now having you on upside our podcast.

Josh Dorkin 7:14
Yeah, that’s, that’s weird. Are you the guy who emailed us about listening in the shower?

Eric Hornung 7:19
I’m not,

Jay Clouse 7:20
but I’ve been copied on a lot of emails Eric has sent with that approximate.

Eric Hornung 7:25
I usually send that to other podcasts Real Estate’s more of a sauna experience for me.

Josh, we like to start on upside with a background of our guests. Can you tell us about the history of Josh?

Josh Dorkin 7:40
Well, when I was a little boy, my mom used to massage me. No, I I grew up in New York. You know, parents are entrepreneurs, went to school. I got to visit my parents. My mom had had a shop, she was a Furrier, very successful, very Arshad built this business from nothing. And I got to go in and watch her work. And that was, that was always a blast. I think, seeing the creativity that she brought to her work. Just always got me kind of jazz. In fact, she was like this crazy marketing genius. I don’t know if you guys remember Cabbage Patch Kids, you guys remember?

Jay Clouse 8:19
Oh, yeah.

Josh Dorkin 8:20
I know you had a few….Actually, I think I see one in the back there.

Jay Clouse 8:24
Absolutely.

Josh Dorkin 8:24
Yeah Jay nice.

Jay Clouse 8:26
Right next to my Raggedy Andy doll.

Josh Dorkin 8:28
That’s, that is legit. That is legit. So during the the craze, which was I think like 85 she was this lady who started making fur coats for Cabbage Patch dolls in order to get media attention. And she ended up getting all this me that she was on Lifestyles of the Rich and Famous National Enquirer she like all this stuff, because she had come up with this crazy idea. And it brought a ton of business anyway. So growing up under that, you know, creativity was was certainly at the forefront of world’s media attention in 95 had to have been like print magazines, probably wasn’t emailing these people. How is she even getting that attention? You know, that’s how did it start? I think it started with like the local news. They picked it up. I mean, she was on like, Joan Rivers show, I mean, just all this crazy stuff. But yeah, it was. It was amazing. And like you said, incredible. There’s no vitality at the time, right? So to be able to do that was was very impressive. Anyway, so growing up with that, when I became a teenager, I would walk to the bookstore and became fascinated by this magazine, Forbes. And they they had this list, as you guys know, the richest, whatever it was 100 500, nationally and internationally. And I don’t know, I just saw one day and I opened it up and I and I started looking and I saw these little tiny snippets. And it would talk about, you know, this guy named Warren Buffett, who bought this company, and then started using that company to acquire other companies. I’m like, oh, wow, okay. And this, this farmer guy who, you know, had a potato farm. And he met a guy named Ray Kroc and did a deal and he became a billionaire because of the potato business. And I was fascinated. I was like, wow, you can create anything. And if you’re smart, and if you stick with it, you could turn it into something huge. And that was just exciting. So every year, I couldn’t wait for the new issue of the, you know, riches to come out because it was just inspiring to read those stories. But you really didn’t care about that early.

Jay Clouse 10:32
Oh, no, we do

Eric Hornung 10:32
We care about everything. Yeah.

Josh Dorkin 10:34
Wow.

Eric Hornung 10:34
Start wherever you want to start. Wherever your brain takes us. That’s where we’re going to go. Be careful. You already talked about your mom massaging us so we really can’t get much more careful.

Josh Dorkin 10:45
She didn’t really massage me. Okay. Let’s just you know, let’s just put it out there. Alright, so, I guess college comes around. I went to wash you and St. Louis. And that was what is it? 1994. I was a freshman. Rewind this tiny bit. My brother is a couple years older than me. He went to university Rochester. And when he went to school, when I visited him, I saw this thing that blew my mind. And yes, it was college girls. No. It was this thing where you can go on the computer, and you can look up the weather in other university, other universities around the country. And it would give you this text display. And it was the coolest thing. Right? Holy cow. How do you Yeah, I was playing I used to play on BBs is, you know, back in high school I would. We had a dial up modem and I would you know, download all these games.

Jay Clouse 11:37
I don’t even know what BBS is.

Josh Dorkin 11:38
Yeah. Don’t What do you like? 12?

Jay Clouse 11:41
Approximately more or less?

Josh Dorkin 11:42
Yeah, there you go. So BBS a bulletin board service. So the pre internet was when you would have a modem. And you would literally dial in if you go and watch war games with Matthew Broderick. And he hacked into government computers. But the more legal way of going around and doing things slightly not okay was to call into other people’s computers where they had all this hacked software, and you would download video games and play them. But then there was this and it was like, Wow, you’re connected to all these other computers almost instantaneously. So that got my brain going. And then when I was a freshman in college, Mozilla, the initial graphic browser was born 94 ish. And I was like, blown away, absolutely blown away. So I just started playing around and hacking away at it and teaching myself HTML, and building websites just for fun. Because I was like, intrigued by this thing, I had no experience. And there was no, like school of coding, because we were all kind of hacking.

Jay Clouse 12:44
What were you building in? What does building websites at the time look like?

Josh Dorkin 12:47
Oh you going to text browser and you just enter some code and save a file? And then look, upload the file via FTP?

Jay Clouse 12:54
Yeah, like pure HTML?

Josh Dorkin 12:56
Yeah. So I built, I was building websites for perfect masseurs. I was just building random sites. I ended up building the site was called g you web. And ultimately, I think I changed the name to simply because I thought the name was cool. And g web was global university web. And it was this, I wanted to create, like this massive directory of universities around the world. So I literally spent hours and hours like finding every university creating this platform. And at the time, there was this like budding site called Yahoo, which was super cool. And I was like, you know, Yahoo, is starting to do all this cool stuff there. They’re building these links in these directories. I could do the same but catered towards college kids, and then high school kids. So I started making partnerships with different websites and doing all this stuff. And it was great, you know, and getting traffic and starting to create this business. And I didn’t know what I was doing. Nobody know they were doing, ultimately, senior year of college came and I had this thing I had been spending countless countless hours on, and I met a girl. And it’s like, internet What? She’s hot. Okay. So it it just died this natural death, which was sad, and in retrospect was quite stupid, because I had a serious leg up on lots of other platforms.

Jay Clouse 14:22
Wow. wasn’t even a pause. It was just a death.

Josh Dorkin 14:24
It just died. I was like, Whoa, this is what everyone was talking about in high school. Okay. Yeah, I’m gonna keep doing this. I’m going to stop doing that the geeky nerdy stuff. So yeah. Yeah. So it died. Post college. I ended up becoming a stock trader. I was fascinating. fascinated with the stock market in high school. I was, I worked at a stockbroker identical sorts of random stuff lasted not that long, because it was very hard on the eyes to literally stare at a screen for eight hours and not blank. Yeah. Massive headaches.

Eric Hornung 15:03
What kind of trading were you doing?

Josh Dorkin 15:06
I was a, it’s called a prop trader. So you know, I put up I think it was like 25,000 bucks, which I’d made and saved and built up. And over the years, I never really liked spending money. And was when I was working for that stock brokerage, I ended up taking what money I had and turning it into a whole hell of a lot of money. That’s awesome. For at least for somebody at my age, right?

Eric Hornung 15:28
What kind of fees? Were you paying on that back then?

Josh Dorkin 15:30
Oh, my God.

Eric Hornung 15:31
It had to be insane.

Josh Dorkin 15:32
Well, if I don’t know it, was it a penny a share? Maybe nickel a share, penny a share…I don’t remember to be honest. All I remember one thing, which was one day I traded one 10th of the volume of this company called EMC, which was a New York Stock Exchange company. And I personally had traded one 10th of the volume of that stock. And I was like, What the hell am I doing? I’m literally I’ve lost so much money in fees, and made nothing. And I was like, this is just crazy. I’m not good at it. You know, I’m getting headaches. The people I knew who are successful, you know, they started getting successful after about a year or two. And I was like, I just didn’t have the patience to continue to lose money. So I left that and went into a career where I was going to make a whole hell of a lot of money, which was independent film.

Eric Hornung 16:23
That’s where everybody on the Forbes list is works in, right?

Josh Dorkin 16:26
Yes, yes. Well, you know, you when you lose some. So I moved back home with my parents. And I started, you know, as a kid, I wanted to be an actor. I was like, let me let me try this out. And so I started auditioning going into New York City. And realize that I would need to I really wanted to learn every part everything about the business. So where do you learn about the business, independent film? And where do you really learn about the business student films? So I started applying to be extra on student films. So talk about being the garbage man.

Jay Clouse 17:02
Yeah, that has to pay quite a bit.

Josh Dorkin 17:04
Yes.

Eric Hornung 17:05
Jay, weren’t you a clown once in a student film?

Jay Clouse 17:07
That was a 48 hour Film Festival, not even a student film, a pure amateur film of people who have no business doing film, and yes I was.

Josh Dorkin 17:15
That’s awesome. So I show up on the set. And I was like, This is awesome. Like, I got it. And so I started doing everything I could to volunteer and learn about independent film. Every time I could be on a set, I’d show up on a set. And what was funny was, the kids at NYU, the kids at Columbia all thought I was a film student, because I was on all these films, we were casting films, I had met a guy on the first film that I had done. And we just became the hustle brothers. And we just hustled and hustled and hustled, I mean, here’s a great example, we, we knew that film festivals were a great way to meet people a great place to meet people. So we would get the book, this is pre you know, again, pre super internet, we get the book for the festival the night before, then we go home, most of these were in New York, we go home, and we’d stay up to like five in the morning. And we would fill out envelopes with letters to every director and every producer who was going to be at the festival, and we put our picture in as well. And so the next day in New York, like you would send something at midnight, it would show up at like one in the morning, their mail is very efficient. And these directors and producers would all know who we were when the festival started. So we’d walk around, and we’d be able to talk to all these folks. And they’d be like, Yeah, we got your stuff. And it created the beginnings of this kind of networking relationship. So we just worked our butts off. But ultimately, I bounced around, I ended up moving to California, realize that California was kind of the stab you in the back versus stab you in the chest, which I fully prefer getting stabbed in the chest, except by the crazy people and realize that it was time to leave the business. So I bounced around every I, for production company, I recruited writers, I worked for an agent, did everything, learn the business backwards and forwards. But I had had enough.

Eric Hornung 19:09
You hear so many of these stories by people who made it through that business about like, the good old days when we were at second city and oh, remember when we were both at Second City together? We were both working on these films together. Did you meet anyone who went on to be extremely successful in the entertainment space when you were kind of hustling around?

Josh Dorkin 19:26
Oh, yeah. Yeah, lots of lots of people. Yeah, I’ve got I’ve got a lot of friends who are doing great things still. And it’s awesome. I mean, they, you know, they work their behinds off again. It’s the quote, overnight success. It’s always funny when those people finally get recognized, and they’ve been working for 15 or 20 years in the industry. But that’s what it takes. You know, there’s not a lot of overnight successes in that or in any other industry whatsoever, despite what the media tells you.

Jay Clouse 19:52
Seems like every overnight success is a 10 to 15 year “overnight success.”

Josh Dorkin 19:58
Absolutely, absolutely. So after that, I bounced around.

Eric Hornung 20:01
So we got internet, we got stocks, we’ve got entertainment, we haven’t got to real estate yet, which is probably what you’re most known for. What happened help us close that gap.

Josh Dorkin 20:10
I’m getting there. So so hurry up man, to everybody who’s sleeping. I apologize. I gotten a real estate license. While in LA, I was like, Hey, you know, it’d be great to maybe make some money, got a real estate license. Did that for like 10 minutes realized, either I was really bad at it, or I hated it, or both. So I got out and then bounced around, I ended up getting a substitute teaching credential again as another way to make some money. And I met a girl I started dating her and her mom, it started this school, many, many years before, and she was working there. She was pretty much running the school at this point. She went from teacher work your way up. So we’re dating and one day they say, Hey, we need to sub i was like, Oh, sure. I’ll do it. I never asked questions about the school and more like, all right, you’re a teacher. Cool, great. Yeah. Well, my first day I walk in and the I go into the classroom, and the first kid walks in, he’s like, yeah, runs up, and there’s a water cooler in the classroom. And he starts mounting the water cooler. And I was like, what, what just happened?

Jay Clouse 21:20
What a response.

Josh Dorkin 21:22
He was very excited to see me obviously. And I realized what I had signed up for, it was a special ed school. And so you know, there were kids who had lots of behavioral and other issues. And and it’s a school, it’s a type of program where burnout is beyond off the charts for teachers and everything else. So I lasted for years, because the day that I started the sub, the guy I was subbing for quit, and my, my girlfriend was my boss, and I can’t balance while I’m dating. My boss. So I was in, I was locked in. Anyway, two years into that I get a phone call from my brother. He’s talking to me about life and and mentions that he had started to acquire some properties where he was living in St. Louis. And I was like, Oh, that sounds really cool. You know, he was telling me about the numbers, the numbers sounded great. And I was like, wow, all right, yeah, I could do this, you know, I still got some cash on the side. So I flew out, his wife was an agent, you know, we started looking at properties. And I was like, Oh, this is this is this is a no brainer. And, you know, things were just dirt quote, unquote, cheap. So I ended up buying a couple buildings, and went back to LA to teach and I was going to be rich, I was very excited. And lo and behold, I hadn’t quite thought the whole thing through. Because I was 2000 miles away, I had to rely on property managers and other folks and contractors who I couldn’t oversee. And little by little this, this whole grand dream of becoming this real estate magnate quickly began to heal. And I found myself dealing with all sorts of dilemmas. Well, how do you get answers to questions, you know, you go on the internet, right? You go to the library, you go to the bookstore. So I went to the bookstore, I found a bunch of books, and they were great. You know, I went to two magazines, and they were interesting. And then I went online, and everything I was coming across, I was finding, you know, the hairs on the back of my neck were kind of standing up a little bit, and I couldn’t quite figure it out. And then I realized that these platforms, business model was not just to educate me, but it was really to give me little bits of information, with the hope that I get sucked into this funnel, where they can sell me more information and more information and more information, and maybe never even actually give me the info that I actually needed. And by the way, that information is not like 1520 bucks, 50 bucks, 100 bucks. I mean, that information is 997. Yes, there’s a seven there, because, of course, that does better to sell a product that 97, the 99. And the $997 course, was really a up sale for some, you know, $5,000…$4,997 bootcamp, which was upsell for a 25,000 24,997 or $49,997, private one on one training up to $100,000. Private, I mean, just out of this world. And I said, There’s got to be a better way. And I looked around and there wasn’t a better way. And I was like, Okay, you know what, I know how to build websites, I’m going to just build a website, put all these resources together that can help me with my real estate. And you know what, I like web communities, I found these forums that were interesting. And I was like, I’m going to create a forum. So I had to teach myself PHP, this new language, to code it and work with databases. And suddenly, I’ve got this quote, unquote, platform. So I’m teaching special at high school lunch break, free periods, nights, weekends, I’m probably working 40 hours a week on my new hobby, while working a 40 hour job. And building up the beginnings of this hobby business that wasn’t really a business just kind of like a hobby, but I needed it to help me stop screwing up as a real estate investor.

Jay Clouse 25:19
These different disparate pieces of information you were looking for at the time for your own real estate knowledge…How much of that was web based versus in these more print mediums?

Josh Dorkin 25:29
Yeah, none of it. I mean, the main media, were giving you that as they would have to the really basics, right? I mean, you, if you were to write a book about every question that ever existed, you would have BiggerPockets, I will platform with millions of pieces of him for millions and millions of posts. That would be a really heavy book. You know, remember the old Encyclopedia Britannica? Yeah, it would look something like that, or bigger.

Jay Clouse 25:56
So how did you in the beginning, get your first online users for this thing, because that’s even hard for people now, and a lot of times the advice is go launch in an existing community, but you’re saying there was not an existing online community,

Josh Dorkin 26:08
there were a few my issue was a I didn’t like their model and be, I thought it was shady to go and try and poach users from somebody else in the space. That’s like walking into McDonald’s for the, you know, Burger King ad, you know, just not cool. You know, nobody’s gonna stand for it, nobody’s going to be happy. So I didn’t want to do that. So I liked going to web web communities. So at the time, there was like web pro world site point forums, there were a couple others. And I would go to the off topic areas. And I found that in the off topic areas, people were chatting about everything that was not the basis of that community, including finance, money, real estate. And what I would do is I would go and I’d answer whatever questions I could about personal finance money in real estate. And I created a little signature, which had a link back to BiggerPockets. And little by little people would start showing up, you know, and then they show up, and there would be this empty community. And so of course, there was me chatting with myself, and lots of clones of myself with different names for you know, the first.

Eric Hornung 27:17
How aware of…this is like 2004, 2005 area we’re talking about right now?

Josh Dorkin 27:22
This is…Yeah, it’s about ’04 or ’05. Yep.

Eric Hornung 27:24
So we got the launch of Facebook happening in parallel to the launch of BiggerPockets, how aware where you have the opportunity to talk to VCs being on the west coast.

Josh Dorkin 27:37
So I’d say by year two, so year, two of the business, I had seen this MySpace, MySpace was hot Facebook, nobody heard of nobody really knew about even though it was you know, I mean, if you didn’t go to Harvard, which I wasn’t at, nor would they have let me in, for many reasons. But…

Eric Hornung 27:54
you just you do seem like a Harvard guy, to be honest. You could you could really rock the Crimson

Josh Dorkin 27:58
Well…you know, it can do pretty well, from time to time. That I’m not going to rip on Harvard, my father in law was a Harvard guy. What am I…

You just did. You literally just did that.

I did not! I did not. Your ears are betraying you, obviously. So what was your…did you ask a question?

Eric Hornung 28:17
I did. I asked VC as an opportunity when you’re launching this community being in the West Coast.

Josh Dorkin 28:22
I wasn’t even thinking about it. Well, I wasn’t, I didn’t think about it at all. I was in LA, I there was no intention for this thing to become a business. It was a hobby, right by by year two, I had quit teaching got married, we moved to Colorado. And you know, I was I was working away making pumpkin making nothing while my wife was supporting us. And I started to think about it because I didn’t really know anything about it before. And being in Colorado, the Denver boulder community, particularly boulder at the time, guys like TechStars. And and, you know, Brad Feld and Foundry, we’re really working hard to establish a community for entrepreneurs. So I heard about this because I was like, Hey, I’m in a start up now. Cool. Let me you know, see if I can learn a thing or two about what that means. And so I went from kind of hobby business at that point to lifestyle business. Now, I had this tech company, and I was living a lifestyle business, which I had no life, I was working, you know, 100 hours a week, every week forever.

Eric Hornung 29:24
Great lifestyle, just plenty of free time.

Josh Dorkin 29:27
Yeah. But I had met with those guys, you know, I said, these guys are experts. Let me sit down and meet with them. And I got meetings. And many, many folks that said said, What are you doing this thing doesn’t have any legs, you should find a model that actually is established and works. And I was like, well, the smartest guy in the room just told me I should stop. Cool. I’m gonna keep going. Did you sounds like you didn’t from the beginning. Think of it as a business. Do you remember when you started thinking of it as something that could be a sustainable business? I’d say when I started to make enough money to potentially offer what my wife was doing. So you know, maybe when I was surpassed my teacher salary by year three or four…

Eric Hornung 30:07
What was the business model? How are you making money early on? If you weren’t thinking about it as a business.

Josh Dorkin 30:11
Google AdSense. Actually Textlink ads, Google AdSense will text link ads was fun, because, you know, it was this cool model. And we all used it and and and then suddenly, you know, this Google, which had taken over the world at that point, was like, You can’t pay for text links. And everybody I knew was doing it. And they literally just like slap massive penalties. And everybody and all our rankings fell and we all lost traffic. And we’re like, what do we do? You know, we we’ve got about down to the Google overlord. And that actually taught me by the way, that I need to build a Google proof business, because at any point, Google could slap me down. And many, many times thereafter, they did not because I did anything wrong, but because they’re like, Hey, we’re gonna change your algorithm, cool. Boom, you know, hey, we’re going to do this boom. And as anybody who grew a site in that era, knows, yeah, it was tough. It was tough.

Jay Clouse 31:04
Now, it’s Facebook in this in a similar way, or Instagram. Yep. Who were your peers, or people you were looking to to model after when you were building an online community like this, at this time?

Josh Dorkin 31:14
I would say those old web forums were the guys that I was looking to, because it was they were well run, they had great information, I very quickly learned in building a forum that you have to have very strict rules, and you have to be willing to enforce those rules. Because if you don’t, people are going to, they’re going to take over, they’re going to dominate and you’re not going to be able to do it. So you know, established a bunch of rules, lay down the law and laid the smack down. And that, you know, brought lots of strife running an online community, I would say is probably below being a politician in terms of being fun. There’s literally very, yeah, I mean, it’s, you know, at least in those early days, right. I mean, it was, it was not fun. It was not fun. I had a lot of angry people yelling at me all the time. And it well, they yelled at us because I spoken wheeze because I needed this company to look bigger than it was. And I did that, for the first eight years before I hired my first employee, a bigger BiggerPockets, something like that.

Eric Hornung 32:16
I kind of want to speed through these 14 years and kind of get to more of a reflective note. But I think that when you see a company grow, in retrospect, it can look like a smooth line. But generally there are catalysts up and catalysts down. Can you kind of talk about maybe 1-3 of those kind of big catalysts that really changed things?

Josh Dorkin 32:36
Sure. I would say every time Google yelled at me, those were downs, the day that my web host, I paid for a dedicated host, we had a bunch of boxes and the day that a drive controller went bad, right around Christmas. And we had web c forgotten our backup protocol for you know, call it a month or three. And I was shut down for three days. And, you know, at that point, I had this thing, it was fairly well established. This was this was how I was making my living and supporting my entire family. My wife had quit her job, we had babies. I mean, this was one of the scariest times of my life, it was really, truly horrifying. But thank goodness, we were able to get a spare part out of I think it was Mexico. And you know, my guys save the day. So thank goodness, but that was that was a that was a bad one. I would say in the early days, when MySpace was hot, I said, Hey, we’re going to build this quote, my space type thing, I had hired a outsourcing firm when I was in LA, to build it, the whole team was in India, and I didn’t really know how to deal with that. I didn’t know how to manage a team, I didn’t know how to handle any of that. And so like six or eight months after, you know, dropping, I think like 15 or 20 grand on this thing. I got back a chunk of code that didn’t work. And I had no money. And I had no working website. And so again, I probably could have quit, probably should have quit. But I didn’t quit. You know, many, many of those along the way. I’d say on the positive note, the day that I realized I didn’t have to participate in the community anymore. For it to thrive, the community began to police itself at a certain point, that was a huge, huge one. I’d say that one of the biggest was was hiring my first employee, Brandon Turner, about six years ago. From there, you know, instead of working 100 hours a week, I was now working 95 and I had all this freedom. It was awesome. That was a laugh moment. But okay.

Jay Clouse 34:40
You need to you need to give us the sign that say, like, “clapping.”

Eric Hornung 34:45
When you make it when you make a bad joke, you got to make sure that you let us know.

Josh Dorkin 34:48
Alright…

Jay Clouse 34:49
I’m so desensitized to bad jokes working with Eric on this.

Josh Dorkin 34:54
Yeah, I get it. So then he came on board. And then you know, all of a sudden, I had this like partner in crime. I had this dude who is as enthusiastic about the business as I was, he was actually a success story, BiggerPockets. And, you know, he was this crazy, creative dude, similar to me. And we just like we just went off. I mean, it was just like, Hey, here’s, like 8000 ideas, let’s keep trying different ones, which I was doing independently. But when there’s somebody else, and you guys like each other. I mean, it’s, it’s fun. And so we launched the podcast, which was I think, ranked 143 in the world. Today, we launched a publishing business. I mean, we started to build these tools and products and all this stuff. And and, you know, suddenly, we’re making it, but by the way, I paid him terribly, because I could not afford him. And and the impetus for that, by the way was I one day went to my wife, I was in tears, it was your eight of the business. And I was like, we’re done. This is over, I’m shutting it down, I could not leave, I couldn’t go anywhere. And I couldn’t do anything. I built business up to such a level that it truly required probably eight to 10 people, but I was doing all those jobs. And so I was on massive burnout. I hadn’t taken a day off in seven years. You know, I was really miserable, broke down, cried, and we ended up hiring a consultant to come in and look over the business and helped me realize that the big, big, big gotcha was, I am in the business. I’m not working on the business. And that was that was huge. Why did you wait so long before hiring Brandon or a first employee in general, I didn’t have money, and I didn’t want to go into debt. So you know, I, I was paying for our lifestyle, which wasn’t a big one. We had one car, you know, we had a baby. But you know, we were comfortable at this point. But all I did was work. I mean, I woke up, I would gotta you know, crawl out of bed and my boxer shorts, went across the hall and started working. And you know, 10, 11, 12 o’clock at night, I went to bed.

Eric Hornung 36:54
Did anyone ever offered to invest to kind of alleviate that burden?

Josh Dorkin 36:58
I had people, users who are very interested. And throughout always there were users who were interested. And I always second guessed it and never thought about it. I’d say I’d never really had I had a few non institutional people in those early in those first eight years to reach out. But that really picked up after, you know, a couple more years at which one, you know, by by year 13. I mean, we were getting hit up every couple weeks

Jay Clouse 37:25
Was “bootstrapping,” or “bootstrapper,” or a term that was used when you were essentially bootstrapping?

Josh Dorkin 37:31
I’m sure it was I probably didn’t know what it was until later on. But eventually, I knew what it was. And I was like, Oh, yeah, this is what I’m doing. This is this is cool. There’s some honor and being a bootstrap. And I was like, screw those VCs, those guys suck. They don’t know anything. And while I’m like, Oh, please give me some money. Somebody, please give me some money screw them,

Jay Clouse 37:51
Was…and benchmarking to the point where you mentioned, you know, as eight years in and you went your wife and you’re saying we shut this down? Because I’m burned out. I don’t necessarily have the money to hire an employee. Do you have a rough estimate of how many BiggerPockets users there were at that point?

Josh Dorkin 38:05
I mean, there were probably hundreds of thousands of users at that point.

Eric Hornung 38:09
Do you have a not at the time, but retroactively now, you went through all this agony of bootstrapping, your life could have been a lot easier if you would have taken some VC money, maybe not on the back end on the exit and everything. But do you have a general philosophy for bootstrapping versus VC? And how do you feel about it now, besides that little dichotomy that you had going on the two shoulders, Angel and devil right there?

Josh Dorkin 38:33
No, but by the way, you know, I mean, for probably the first 10 years, everybody, well, at least in the first few years, everybody gave me crap. Like why don’t you get a real job once you get a real job? And then I turned 29. I was like, Oh, my God, like, what am I doing? This is crazy. All my friends are like, you know, they’re getting close to that six figure job. They’ve all got families, they’ve got all this stuff going, everybody’s got things going for them. They’re all happy. And I was like, I was so envious. And then, you know, you’re eight, just absolutely envious. I was living a good, you know, I was finally making the money that they will had eight years earlier. But I was working for myself. And what I started to realize where all those friends had jobs that they kind of hated, you know, and after the first bunch of years of like, You’re an idiot, here’s a penny, I just picked it off off the street. Let me mail it to you, because it will help you with your business, which Yes, somebody actually said to me, yeah, that was pretty effed up, I realized that that independence, like, I just I thrived on it, I really enjoyed it. I hoped for the day that I can really start to turn into a business and figure that out. And so that was amazing. Now, now to your question about bootstrap versus Angel. My philosophy is this. I think the media is doing a drastic disservice to young people today, or anybody today who’s contemplating the idea of starting a business, particularly a tech business, you know, by, you know, I look, we should celebrate Salesforce, we should celebrate Microsoft, and Facebook and Insta and all these, you know, radical unicorns. I mean, like, the odds of these things happening are infinitesimal. But that’s the problem. The media doesn’t tell you that, you know, the media tells you, you too, can be one of these guys. And so everybody comes with an idea on the back of a napkin is like, Hey, I’m going to be a billionaire. And they’re all fooling themselves. And, and it’s a shame, because, you know, had they stopped and thought about the idea. So many amazing businesses have died, either because the person went and tried to get money and couldn’t get money, went and tried to get money, got many the VC killed the business or completely transformed what the business was, because they needed to make the return that they said they have to make on this investment. So like, you know, they forced a pivot that the the initial entrepreneur didn’t want to do, and eventually fired the the entrepreneur, which happens constantly. I mean, there’s all these scenarios that play out, and it’s an absolute shame. So, you know, from my perspective, I think VC is great, I think it’s absolutely a great means to an end, I think what needs to happen, more and more is a the media really, really needs to share the people who are crushing it without raising money. I think people need to get their head screwed on and realize that, you know, building a business that doesn’t million dollars in revenue is awesome. building a business that does 10 million revenue is even more awesome. And you know, if you could get to 50, and 100, and a billion Good for you.

Jay Clouse 41:36
It’s actually kind of interesting, because the people who are running those types of business and crushing it on their own, they don’t even want to be found, you know, a lot of times they’re like, this is going really well, I’m going to stay out of it, I’m going to stay out of the limelight, and the media is kind of looking around and almost organizationally, they get contacted by people who want the limelight, and they’re those people who are using PR as a marketing play. So it’s it’s an interesting organizational design challenge.

Josh Dorkin 42:00
Well, we were doing that I mean, you know, we kept our heads down, when when the business really started to grow, we just kind of kept kept her head down. Like I, I didn’t want the drama that might come with more media, I didn’t want to deal with that chaos. And we actually ultimately, a couple years ago, try PR were like, this is such a waste of money. Because I done my own hustling getting PR over the years, I’ve gotten a lot lots and lots and lots of PR, what I realized was PR was bogus, like most PR gets you, at least for us got us nothing. You know, it was an ego trip. It was cool. I could share it on Facebook and tell my friends that I’m famous and successful. But like, it didn’t drive users, like, you know, I’m already getting millions and millions of users like, you know, what’s an article? I mean, we had a great article in the Denver Post full page with my picture and everything. Yeah, I got like, you know, 40 new users. I mean, it’s not worth the time.

Jay Clouse 42:52
What was your real estate portfolio, like when you’re in the heat of building this? And how did you prioritize getting that attention?

Josh Dorkin 43:00
That’s a great question. So I got to a point where I realized I had to get off the pot. I had I, I either was going to build this business. Or I was going to build a real estate business. And I had to I realized I was incapable of doing both my own persona I I knew that if I was split between these two things, they were both going to suffer. So I ultimately ended up selling my portfolio. And this was, I think, oh seven so good timing. I still lost my shirt, and ended up focusing full time on BiggerPockets.

Eric Hornung 43:36
Did that feel at all hypocritical?

Josh Dorkin 43:38
No, I A lot of people ask me people have asked me that countless times you’re a friggin hypocrite And my response my clever responsive It was very clever was you know can Mark Cuban own the Mavs and not be a professional basketball player. I mean, what’s hypocritical about it, I think further further by the fact that I was never purporting to be the expert. And that was a different one of the differentiators between BiggerPockets and all these other people in the industry was like, I was not the quote unquote, Guru. I didn’t want to be the guru. Like I, I’m just, uh, I’m here to learn, like everybody else, I could certainly answer. You know, I’m an academic, I can learn. I can answer, you know, 99.9% of your questions. But, you know, I’m not out there purporting to be this expert, like, all these other dudes are, in fact, that was the idea was like, let’s bring in actual people who’s, you know, who are getting their hands dirty. And let’s allow for the democratization of information in the niche. And so that’s what made BiggerPockets so successful was it wasn’t about me, I didn’t matter I was meaningless. And, and by the way, that, that, that shows up further, as we talk about, you know, when I ultimately brought in partners when I went through, you know, all this drama, familiar, familiarly, and had to step away from the business and like, there was, there wasn’t a blink, nothing happened. Because I built this business. That was not only Google proof, but it was also Josh proof.

Jay Clouse 45:07
You hired Brandon as your first employee. What changed that allowed you to now have a large team, like when did you start getting to a point of cash flow that you could hire these people?

Josh Dorkin 45:17
So hired Brandon, give me a really crap salary. And he didn’t need to work for me. So he’s like, Yeah, I’d love BiggerPockets, let’s play. And so we played and played and literally, like, you know, being able to have the bandwidth of, or at least having one person focus on one thing versus one person focus on, you know, 27 allowed that one thing to improve, right. And so that was his job became focus on content, focus on community, and focus on writing and producing that kind of stuff. And then I can focus on the business side, right. And that allowed for our revenues to drastically improve. And I think, yeah, I had, I believe I doubled revenues the year before he came on, and every year thereafter, we doubled and doubled, doubled and doubled. And, you know, the business was just began to explode. So, you know, once he came on, you know, revenues jumped dramatically, I was able to pay him better and hire the next guy, you know, and then within a year, you know, I could hire two or three more people for more people, and suddenly, you know, it just it snowballed.

Eric Hornung 46:20
It was pretty easy for you to leave g when you saw one hot girl and like ran away. How hard was it to leave BiggerPockets? Leave the trenches of BiggerPockets?

Josh Dorkin 46:30
Ironically, trench is the man running BiggerPockets.

Eric Hornung 46:33
You like that? You like that?

Josh Dorkin 46:34
Well played. I hope you knew that.

Eric Hornung 46:36
I did. Yeah.

Josh Dorkin 46:37
Okay.

Jay Clouse 46:38
Seriously?

Eric Hornung 46:39
Yeah.

Jay Clouse 46:39
Oh, wow.

Josh Dorkin 46:40
Nicely done. Yes. So let’s kind of rewind. So currently, we’re talking it’s, it’s, it’s what, April 2019, right, November 2017. And I went through this horrible thing, my daughter got a normal surgery turned out to develop an infection, she ended up going through all this trauma, and, you know, became pretty much knocked down paralyzed for a period of time. And so as soon as that first surgery happened, and you know, I went in with her to the surgery, and I never went back to work. Now, I’ve got to rewind a tiny bit, because in the preceding call, a year or so, I was going through a pretty dark period of BiggerPockets. Personally, the business was doing great, the team was good. I started to wonder if I was loving what I was doing still.

Jay Clouse 47:31
And this was like, 12 years in, right?

Josh Dorkin 47:33
This was 12 years in, you know, a lot of people had told me, hey, there’s there’s two types of personalities. There’s the guy who builds the the business, and then there’s the guy who scales the business. And I was like, okay, but I could do both. Sure. Right. And by the way I can, and I have, and I did, but I think, you know, whether it was, you know, personality wise, or whether it was I was just so burnt out over all those years, I was having a really hard time, I wasn’t particularly loving management, I wasn’t loving that I wasn’t getting my hands dirty. And I was, you know, I was becoming a bureaucrat. And that, to me, didn’t feel authentic, it didn’t feel right, something wasn’t right, I hired a coach, Coach worked with me, I got better at what I was doing, I started to like it a little bit. And then I stopped again, hired another coach went through it again. And same thing, and I was like, I can’t keep doing this. And I was just torn. You know, we had had some private conversations, myself and a couple other close friends, you know, hey, is it time? Is it time is the time the company is doing? Well? If we were to kind of have an exit? Yeah, I’d be okay. And should I do this? Well, this thing happens with my daughter, I have to step away. And, you know, within a week of it going down, I call Scott, my then was the VP of ops and Brandon my confidant, closest confidant at the company and said, Guys, I mean, it was an hour of me babbling in tears. I mean, I, I couldn’t get the word out, I was just so distraught by everything that was going on with my family, I said, you guys, you know, take care of it. I can’t even possibly concentrate on the business or think about it while I’m going through this. So several months past, they’re running it, you know, I’m getting periodic updates, things are going well. And come call it April ish, April mash. It was like, I had a lot of time to think a lot of time, you know, I’m the first time in 13 years to really think about myself and my life and not, you know, I mean, going through something like that and feeling you know, I mean, there were periods, I thought I was gonna lost my lose my daughter, you know, there’s nothing worse, there’s nothing worse than and there’s nothing more important, at least for me, I realized nothing mattered more than my family, nothing. This thing I put every ounce of blood, sweat and tears in for, you know, 13 plus years, didn’t matter it all to me at that very point. And I was like, Okay, well, that that might be a sign. And so I started to read about things like how happiness was like, you know, am I happy? Am I miserable? What’s going on here? What am I dealing with? And, you know, start to realize that I think I was semi unhappy through a lot of these periods. And, and, you know, maybe who knows what the reason was, but maybe it’s time to start fresh. And so, you know, I had a lot of really tough, very, very difficult conversations with my my team and and decided, you know, what, I’m gonna bring in an investment bank. And we’re going to put the the business on the market. So we did that. And, you know, call that March, April, April, May. And November six of 2018, we did a recap recapitalisation of the business, we brought in a private equity shop, they took a piece of the business. And I took took my number to Scott. And we promoted him to CEO, the company, we kept everybody in place to this day, everybody’s barring the one guy who left for another job, but we kept everybody in place. And the company has, you know, been flawlessly been executing and continuing to, to beat expectations and crushing it.

Eric Hornung 51:09
Scott’s young. He’s like, 28, 29?

Josh Dorkin 51:12
baby.

Eric Hornung 51:12
yeah, how come he was the right guy?

Josh Dorkin 51:15
Scott was the right guy, because, you know, he was the right guy, because Brandon wasn’t, and that’s not a dig on Brandon, Brandon is that that creative guy who’s got his hands and all the creative forces of the business, Scott was the guy who came in with the intention of kind of being the back office, you know, right hand man. And he was and he knew that company, he he knew how to run the company. You know, my loyalty would have been to Brandon if there was a choice. But you know, frankly, Brandon didn’t want to deal with the management didn’t want to deal with the chaos of that. And Scott thrived on it. And so Scott was also a success story of the company, and a massive, massive fanatic. In fact, you know, when I met Scott, I was working in this co working space. And he was getting a tour of the CO working space and somebody walking through and they’re like this, this company’s this, and there’s BiggerPockets. And like, I heard it overheard it while I was sitting there, and like, his mouth drops. And he was like, oh, BiggerPockets, BiggerPockets, you know, lost his mind. Super ecstatic. Ultimately, I ended up hiring him. That’s a whole story behind it, but a huge fan of the company. And he had what Brandon and I didn’t have, you know, he had this cold, not not in a bad way, like this calculating ability to organize and run and, you know, deal with metrics and deal with all this stuff that, you know, I didn’t love doing. You know, I did it. That was okay at it. But he loved doing it. So that was a big question like, hey, can this young kid 2728 run this company? You know, and I think we thoroughly convinced our partners, that he was the right guy. And I think he continues to prove that he is the right guy. You know, Scott, fantastic. The staff respects him, loves him, the community loves him. And yeah, I think the board is very happy with him. So I’m quite pleased. And I know, my partners are.

Eric Hornung 53:11
Jay and I have this idea that we’ve been tossing around the last two months about, is this an entrepreneur’s masterpiece? Or is this just a business that they’re going to crush? And it seems like you have been a serial entrepreneur throughout your life? Yeah, I mean, we talked through all the different places you’ve went, the things you’ve built…

Josh Dorkin 53:27
Failed at.

Eric Hornung 53:28
Failed at, yeah. You know, well, I was gonna leave that one out. Josh, I was gonna give you a little bit of love there.

Jay Clouse 53:33
I’m talking about…what is it, UGweb? UBweb?

Josh Dorkin 53:37
GUweb.

Jay Clouse 53:38
GUweb.

Josh Dorkin 53:39
You know what the power of…

Eric Hornung 53:42
he was persuaded.

Josh Dorkin 53:43
persuasion. Yeah, there. Yeah. Yeah.

Eric Hornung 53:45
So I guess my question is, what’s next for Josh Dorkin? And is this the masterpiece? Are we done? Or is there something more?

Josh Dorkin 53:52
I mean, this is a pretty serious masterpiece. I mean, you know, it’s funny, I’ve had a lot of time to think and look, BiggerPockets isn’t a billion dollar business, I actually believe it can be you know, I think the thing that gives me the most pride the most joy in this baby that I built was, there’s very, very few companies out there that you can think of that you can name that have a fundamental impact on people’s lives for the positive, right? My my company me BiggerPockets. We’ve changed the lives of millions and millions of people and and have helped improve these people’s lives for the better help teach them financial wellness, teach them how to build money. I mean, we’ve taken people who hate their jobs and have helped them find a pathway to leave to quit and build their own mini little entrepreneurial empires in this in the space of real estate. And, I mean, there’s nothing like it. I mean, I continue to get emails and texts and tweets and all this stuff from people, that that I’ve fundamentally changed your life for the better. And so from that perspective, I don’t know that there’s any going up, I think the only way for me to do better than that is potentially to run for office and change the world, which I toyed around with, by the way, but I think from a business perspective, I think it’ll be a serious challenge, in terms of, you know, what’s next, I would say, I’m 98% going to launch my own podcast pretty soon in areas of interest to me, you know, you know, not being restrained by the business and not wanting to damage the reputation of the business by opening my mouth. And because, you know, loose lips sink ships, I, you know, I want to talk about ideas, I want to talk about health, I want to talk about happiness, I want to talk about entrepreneurship, I want to talk about things that intrigued me. I’ve been I’ve got a notebook, where I’m writing ideas, you know, the issue is, I think it’s too early for me to dive in on something. So you know, I’ve got all these ideas, and I’m like, Oh, my God, this is the one This is amazing. This, this can be a billion dollar business. You know, this could be here just can be successful in this can really be helpful to a lot of people. And then I stop and I say, but do I really want to run it? And and so, you know, I’ve been talking with a lot of people, I’m certainly looking to advise young companies hoping to help startups, that’s something I definitively want to be doing, looking to do some investing. So looking for opportunities to whether it’s startups or anything else get involved in things like that. I’m toying with writing a book right now about what I’ve been through my experiences, and there’s a whole hell of a lot more that we didn’t talk about, and playing around with different things, you know, I stopped and I just think, how can I better this earth? How can I better this world? You know, I’m toying with things like, Hey, you know, can I come in there? Can I come in and help try and sell hunger? I mean, legit, these are like, the crazy ideas that I have, can I solve hunger? Can I help solve the food desert problem in America, in our cities, and, you know, get good food and, and, and fresh produce to folks who currently can’t get access is to, to that that kind of thing? You know, can I solve all these? So that’s what I’m doing a lot of brainstorming a lot of networking, trying to meet people looking for opportunities, and the podcast will see, you know, I don’t know, I don’t know what tomorrow is going to bring. But you know, hopefully, I’ll find it.

Jay Clouse 57:13
it seems like you have a very healthy division between Josh Dorkin the person and the business that you had built. Did you always have that divide? Because we talked to a lot of entrepreneurs, or at least I talked to a lot of entrepreneurs, who very much feel consumed by the business, and they are the business and a point like this, where you are, you have to have that division to really move forward as quickly as you are.

Josh Dorkin 57:35
So I was the business. Absolutely. The business, I wasn’t the guru, right. I wasn’t the guy. But I was the business. And, again, in everything that I you know, I tried to be very thoughtful, and how to create a sustainable growing business, you know, the podcast allowed us to become less reliant upon Google launching the publishing business allowed us to become less reliant upon advertising, you know, there’s all these things, created this conglomerate that a lot of people said was crazy. And they’re like, well, you’re gonna have a lower valuation for your company, because nobody understands it. And nobody understood it. I talked to a lot of people, they’re like, we don’t get it. We don’t really understand it. The people who did, there were few. And ultimately, the folks who ended up partnering with me certainly got it and, you know, they get it this business is sustainable. But in so doing that, over the course of call it the last five years, there was definitively a methodical approach to getting Josh the hell out of the business. And a lot of by the way, was Scott Scott, just saying, you know, hey, Josh, you know, well, I think the first thing was Scott said to me, Josh, you need to take money out of this business. And I because I was literally plowing everything back back in and he’s like, there’s a reason you’ve worked so hard all these years, you know, like, you should reap the benefits of what you built. And we argued, like constantly about that. And he eventually won. And I was like, Oh, you know what? Now looking back. I’m like, Damn, I wish he had one earlier.

Eric Hornung 59:04
That’s some game…That’s some Game of Thrones stuff right there. He’s forcing you out, manipulating you, Scott trench.

Josh Dorkin 59:09
Yeah, he ended up winning. Interesting. How that works out. But yeah, so the idea was like, how do we make the business Josh proof? And I look a lot of companies and businesses from friends of mine, I’m like, you know, gosh, I, you know, like, I really want to see them do that. You know, I think we took the approach of I’ve got to get out of this thing. But yeah, the podcast was instrumental in captivating people and and reaching people’s imaginations. You know, it’s one thing to read, it’s one thing to watch a video, I heard this great talk. And I think it was at podcast movement, this this great podcasting conference, where somebody had talked about why podcasting and why the radio was so powerful. And what happens when somebody is talking is your brain is just spinning, you know, you don’t have the visuals provided for you. So you create the visuals in your head, you create the visual story. And so there’s been all these psychological tests on advertising and things like that. And it turns out that that podcast advertising is so much more powerful, because the trust and the connection to these podcasters at least on Good, good podcast, which I hope we have, and you guys might have here, and and…no, this is great.

Eric Hornung 1:00:22
That was so close to a compliment that was so close.

Josh Dorkin 1:00:25
The show is awesome. You guys are awesome. It’s just so much fun. But anyway, yeah, that’s I’ll shut up.

Eric Hornung 1:00:30
This is a great show. I have one last question. What’s the purpose of the new podcast? Is it just Josh discovering What’s next? Or you said that the purpose of the last podcast was to inspire people and obviously it worked well with the business. But what’s the purpose of the new podcast?

Josh Dorkin 1:00:46
I think it’s both I think it’s I’m bored. No, that’s not true. That’s not the reasons the launch of podcasts. Come on. Stop it.

Jay Clouse 1:00:52
It’s the reason a lot of podcasts are launched, though.

Josh Dorkin 1:00:54
Yeah, no, it is

Eric Hornung 1:00:55
It’s the reason a lot of podcasts are garbage.

Josh Dorkin 1:00:57
It is. I, you know, I have I have a ton of questions. I have not lost my curiosity. In fact, by the way, speaking of curiosity, there’s an amazing book about curiosity by Brian Grazer, if you’re looking for an interesting part, I’m Curious George is that it’s not it’s not curious. George Would you stop? Oh, my God, Brian, you Brian Grazer was like mega mega mega producer in the in the film business, you guys will look it up and share it. It’s, it’s it’s fantastic. So it’s curiosity. And I think it is partially trying to help people, because I think I’m in a privileged position today to not being forced to work at this moment. You know, at some point, I will if I’m not smart, and I want to, because I’m going to lose my mind if I don’t. But in terms of the trauma that I went through with my daughter, and the stuff our family went through, just really had my head spinning. I think I’m blessed that I had the opportunity to look back upon the previous bunch of years running the business and realize all those things I would have done differently. And and now, I can do that I can examine what I did, right, what I did wrong, what changes I would have made, and a lot of those were not necessarily just business entrepreneurial, things, those were lifestyle things, you know, I should have eaten better way sooner, I should have taken care of my body way sooner, I should have stopped and thought about happiness sooner. You know, we all become so consumed with our lives we all you know, I I think I was not the only one guilty. The reason I was miserable at your eight and cried to my wife and brought in this consultant was I was in the business, right. And I think what I’ve discovered and what I believe in may or may not be true, but I believe it to be true is that the vast, vast, vast majority of people and by the way, everybody I talked to almost everybody I talked to falls into this bucket is so stuck in their lives versus working on their lives. So again, in the business versus on the business, once I change that changed my life for the better. The same applied for my life, once I started working on my life versus being stuck in my life and and being a prisoner of my own life, things changed dramatically. And and so I want to explore that I want to talk about that I want to meet you know, experts in all these different fields. And you know, just talking about the things that interest me, I think it’d be fascinating and I think hopefully if I can help you know somebody who’s you know slaving for their boss and step away from that or somebody who’s just been miserable with maybe it’s their home life or maybe it’s their career or maybe it’s some other piece of their life I can help them with that then I’m winning so you know what when that happens I’ll announce it on on my Twitter which is @jrdorin plug. But yeah, that’s it.

Jay Clouse 1:03:46
well you just plug I was going to get the opportunity to plug so to follow along the journey go to at jrdorkin on Twitter anything else that people should do if they want to follow along and get the news on this podcast or anything else that you’re up to?

Josh Dorkin 1:03:58
Right now it’s Twitter Insta probably need to launch a personal website which I will announce and or link to from both sites. But yeah, I you know, I like not having all the connections I shut my LinkedIn down. I like just kind of like keeping you posted on the deal a little bit here. But you know if I’m gonna launch a podcast, I probably need to pick it up a bit.

Eric Hornung 1:04:21
All right Jay. Man, that was a fun one. We just talked with Josh Dorkin of formerly BiggerPockets. And now who knows…What do you think?

Jay Clouse 1:04:32
A lot of fun Dorking around on this interview.

Eric Hornung 1:04:34
Oh my gosh…that was, did you plan that one?

Jay Clouse 1:04:36
I did in my head just now. But as of like, 30 seconds ago. Yeah, different energy to this lot of fun. Something that if you listen to the BiggerPockets podcast will feel familiar from Joshua style. And I recommend if you guys enjoyed this conversation, to go back and listen to something I already visited today, Episode 100 of the BiggerPockets podcast, which is another interview of Josh but several years ago when he was still in the thick of running the company. But Eric, now Josh, moving on to a different challenge, a different calling. And I’m excited to see what’s next.

Eric Hornung 1:05:08
Likewise, I think it’s going to be fun watching him discover what’s next. And I’m sure whatever podcast he puts out will be fantastic. He mentioned that there will be a co host I’m curious to see who that is in the comments to his tweet or Instagram. He said it won’t be Brandon. So I’m, I’m wondering who that will be what this podcast will be about what it will find and I definitely will be subscribing.

Jay Clouse 1:05:31
I wish we had another hour because I had lots of more in the weeds questions. A lot of friends. I mean, if we were just looking at Josh, as a founder, we’re talking about nearly 15 year business journey that was bootstrapped. I had a lot of questions about that. selfishly, I had a lot of questions about building a media company in a community because that’s something you and I aspire to, but really had to rock it through the 15 year journey itself, although we really hit some highlights and he shared some really insightful moments from the time he went to his wife eight years in and, and said, you know, it’s over, We’re shutting it down to this most recent, familial, familial, it’s a hard word to say it is a hard word to say. familial struggle that has brought some new clarity and direction for him. A lot of rabbit holes, we could have gone down.

Eric Hornung 1:06:18
Oh, yeah, this is this could easily be Tim Ferriss style three plus hour podcast, talking about all the ups the downs, the feelings, the emotions, the decisions, the almost the what ifs, and we still managed to cover a lot of those. But it definitely could have been longer.

Jay Clouse 1:06:34
Something we didn’t get into. But the pattern that I’m starting to put together on a couple of episodes of BiggerPockets I listened to today is co host Brandon mentioned when he got his real estate license, his wife was his sugar mama for a little bit of time so he can get his legs under him. Josh mentioned that his wife supported them for a while in the early days when he was starting the business of BiggerPockets. I was literally sitting in my girlfriend’s apartment yesterday, and thinking about how having her supporting me makes me like a superhero. And some of the things that I’m doing right now because she takes care of a lot of things for me that I don’t ask, I don’t expect, but she she’s just really good to me. It seems like for people in this entrepreneurial journey, it’s often a lonely, hard time. And sometimes, you know, a layer of people’s success that may not get the credit that it should or the whether it’s a significant other or not the people around them really supporting them and helping carry the load.

Eric Hornung 1:07:28
I wonder how often we as men fail to be supportive in that same capacity when the tables are turned?

Jay Clouse 1:07:35
Probably constantly.

Eric Hornung 1:07:36
Yeah, probably constantly. Well, that’s sad I guess

Jay Clouse 1:07:39
That’s a bummer. any big themes that came out of this interview that you wanted to touch on?

Eric Hornung 1:07:45
I guess for me, it was cool hearing a lot more depth from Josh. I mean, I’ve listened to I don’t want to misquote the number, but it’s definitely over 200 episodes of BiggerPockets. It’s either 250 or 300. I think they’re at 350. Now, so I’m pretty close to that. Which means that I have like, learned his story over time. And I think when we got off the mix, I told him it was like talking to an old friend. Because we’ve talked about this before when we had Melbourne and this whole idea of I have spent so much time with this human being and kind of listening to their conversations, but I haven’t had the actual conversation. They don’t know who I am. So it’s just a weird dynamic that I think we’re going to get more and more on this podcast. And once we get Seth Godin on here for you one day, I’m sure that’ll be the same way.

Jay Clouse 1:08:34
Time will tell you know, here’s a fun fact, Eric, what Tim Ferriss interview, or interviews do you think are my favorite? You know, I’ve never listened to the Tim Ferriss podcast ever really? Right. Yeah, there’s some gold there. I’m sure there is. It’s not the scarce information of some of the lesser known podcast, you and I have talked about seeking out? Well, it was it was a trick question. My favorite Tim Ferriss interview views are actually the interviews of Tim Ferriss that are not on his feed, I found in multiple cases, it’s only coming to him right now. But the pattern exists in my brain. I found in multiple cases, when somebody creates content, and is the interviewer or is the voice behind the brand, it’s often more interesting to hear their voice on a different outlet, because they’re less concerned about their brand alignment with that specific audience or community. And I felt that a little bit in this interview.

Eric Hornung 1:09:30
a little bit of inside baseball here for the listeners Jay and I tried to record co host interviews here on the podcast, and I felt a little uncomfortable. Whereas I feel like I would have been more comfortable if it wasn’t on my own podcast. And I think I specifically said that at the opening of the interview. So definitely, you get some more insight you get people in of space that feels that they don’t feel constrained by hopefully. What about you Jay, do you have any big takeaways?

Jay Clouse 1:09:59
Something that struck me at the time that he was starting to build his community, you know, I asked him specifically Who were your peers, or the people you modeled after when building this. And he mentioned other forum communities, but nobody specifically. And he was an early mover in this online community media space even said that a lot of the people he spoke to just didn’t understand the business even to this day. And I think that’s the case for a lot of bootstrapped founders, or people who are really at the fringes, it’s hard for them to even find peers to share best practices with because they don’t exist yet. And I guess that’s kind of the story of entrepreneurship to like, there’s no blueprint for it, or you wouldn’t be doing it. But often you have some peers, you know, you have the indie hackers community who are all about people who are, you know, bootstrapped founders making SaaS products for the most part, or informational products, that kind of struck me as something that was surprising. He also mentioned, you know, up to your eight, he wasn’t making money enough to hire somebody. And to our interview with Kevin and Tyler, they mentioned, you know, this kind of training off in the SaaS space or in the bootstrapped founders journey of this period of time, where you just aren’t quite there yet, and aren’t quite making the revenue. But you know, at this point, millions of users on the BiggerPockets, community 58 million downloads, they published eight print books, and they’ve sold almost 350,000 copies in the last five years. So some remarkable success. But I think people you know, listening to this, when I asked Josh, you know, benchmark me at that eight year mark, how many users do you think he had, and he said, hundreds of thousands, growth takes time. It’s hard. And sometimes big numbers don’t necessarily mean or equate to giant financial success.

Eric Hornung 1:11:40
Yeah, I thought it was amazing how quickly things turned in the story, when he kind of had that revelation to not work in the business, but on the business and when Brandon came on board, and I think that I mean, you are way more qualified than me to talk about this with unreal and what’s going on there. But I think that that’s probably something that a lot of founders feel.

Jay Clouse 1:12:00
Part of it is. And if you listen to Episode 100 of the BiggerPockets podcast, when I interview, Josh, you mentioned as part of this is they take very strong stances on what they will and won’t sell to their users, they really try to make everything available for free, as far as information knowledge goes. So I do not doubt that he could have been making lots of money by year eight with that user base, if he was not as altruistic in the way he was approaching that. So that’s a choice that I applaud, I think is better for the business in the long term, certainly better for building the community long term. But all those decisions are very important decisions that somebody in his business position had to make.

Eric Hornung 1:12:42
Yeah, really elongates your thousand day rule there, huh?

Jay Clouse 1:12:45
Yeah.

Eric Hornung 1:12:47
It’s like a 3000 day rule. All right, Jay, well, if people want to interact with this episode, if they want to interact with us, where should they go?

Jay Clouse 1:12:56
As always, guys, we’d love to hear from you and hear your thoughts on this episode. You can tweet at us at upside FM, where you can email us Hello at upside down FM. We’re always looking for people on the fringes. We’re looking for new guests, we’re looking for people with interesting stories, feel free to send them our way or tag them. And of course, if you enjoyed this episode, we’d really appreciate a rating on your favorite player. Maybe the only platform that actually allows that is iTunes. So if you enjoyed this, please leave a five star review on iTunes. Tell us what you think it helps us bring on more high quality guests like Josh to the show. Thank you, and we’ll talk to you next week.

Interview begins: 07:00
Debrief begins: 1:04:20

Josh Dorkin is the founder and former CEO of BiggerPockets. BiggerPockets.com is the nation’s largest and most active real estate investing social network, designed to simplify and enhance networking, deal making, data evaluation, education, marketing and transactions for investors, consumers and professionals.

As of January 2019, the BiggerPockets podcast had amassed over 58 million downloads and was the top real estate investing podcast on iTunes. Their publishing arm, BiggerPockets Publishing, launched in 2013, has published 17 print books. These titles remain near the top of the real estate charts since launching, selling almost 350,000 collective copies in just five years.

BiggerPockets was founded in 2004 and based in Denver, Colorado.

Learn more about BiggerPockets: https://biggerpockets.com
Learn more about Josh: https://www.joshuadorkin.com/
Follow Josh on Twitter: https://twitter.com/jrdorkin
Follow upside on Twitter: https://twitter.com/upsidefm