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How to Turn a Hobby Into a Booming Business (Then Get Your Life Back)

The BiggerPockets Business Podcast
61 min read
How to Turn a Hobby Into a Booming Business (Then Get Your Life Back)

If you think you know Joshua Dorkin’s whole story… think again.

In the debut episode of the BiggerPockets Business Podcast, the BiggerPockets founder reveals exactly how he bootstrapped a hobby site into the world’s biggest online community of real estate investors. He also discusses how he worked 100-hour weeks in his basement (and in his boxers), and how somewhere along the way, it dawned on him that he’d built a “lifestyle business” that left him with no real life.

Joshua traces the business back to the days when MySpace was hot. He offers tips for building an online community that will resonate today and into the future. He describes a few moments when he almost quit ($15,000 for a website that didn’t work?!) and reflects on why he waited eight years to make that game-changing first hire (Brandon Turner!).

But for as many lives as BiggerPockets has touched, this episode is about something more profound than one company’s growth. You’ll learn what that is when Joshua reveals why he’s been out of the public eye lately and the reason he stepped back from day-to-day operations just as BiggerPockets began to reach new heights.

This show will give you a lot to think about—whether you run your own business or you’re just thinking about taking that leap. It’s a perfect jumping-off point as we launch the BiggerPockets Business Podcast with the intention of helping one another make a real, positive impact on the lives of our customers, our teams, and our families.

Listen now, and make sure you’re subscribed so you don’t miss an episode!

Click here to listen on iTunes.

Listen to the Podcast Here

Read the Transcript Here

J: Welcome to the BiggerPockets Business podcast.

Carol: This is show #1.

“There were various phases of this business. It went from hobby site to lifestyle business. Now, mind you, I did not have a lifestyle business because I had no life. And then I got to the point where I hired my first employee and it became an actual business. And then the final phase was where I brought on a partner and this business was now in full rocket ship mode”.

Welcome to a real-world MBA from the School of Hard-Knocks, where entrepreneurs reveal what it really takes to make it. Whether you’re already in business or you’re on your way there, this show is for you. This is BiggerPockets Business.

J: Hey there, everybody. I am Jay Scott. I am your co-host for the BiggerPockets Business podcast and I am here with my other co-host, my lovely, amazing, beautiful, smart, and awesome wife, Mrs. Carol Scott.

Carol: Wow. You are like—what are you digging for there, honey? Do you want something later?

J: No, I was told I was supposed to be nice to you on the show.

Carol: Oh, that’s a really, really good idea, producers. Good call on that. Anyway, I’m having a really good day, honey, how’s your day?

J: I am doing well. What’s going on in your life or our lives?

Carol: Our life is ridiculously good right now. I don’t mean to be all braggy but I’ve got to tell you, honey, in like 16 years that we’ve known each other, there have been few times that are just like this where there are so, so many good things all going on at the same time.

We’re getting ready to sell the house. We’re doing a big move to Florida. We’re starting another business. We’re starting this podcast. It’s so much good stuff all at once. A little overwhelming, I can’t lie—but it’s a lot of good transition and it’s a really good time right now.

J: I absolutely agree, and speaking of transition, we have a really great first episode today. We have a guy named Josh Dorkin. Many of you may know him and he’s someone who’s going through a whole bunch of transitions in his life, both personally and professionally. For those of you who don’t know Josh, Josh is the founder of BiggerPockets.com.

BiggerPockets is the #1 online investing resource for real estate investors and real estate investing, and Josh has grown BiggerPockets to a community of nearly 1.5 million people over the last 15 years.

But, when Josh first started, BiggerPockets was basically just an idea in the back of his mind. He started like many business owners, trying to figure out how to grow the business, how to scale the business, how to grow his community, and he’s here today to tell us about all the struggles, all the trials, all the tribulations that he experienced while trying to grow BiggerPockets into what it is today, a company that has over 30 employees, dozens of contractors.

So I am really interested in digging into this show with him and learning about how BiggerPockets started. Honestly, the story is a lot like how a lot of businesses start, so I think our listeners are going to take a lot away.

Carol: So here are the specific things you’re going to learn in this show. So Josh is going to tell us what actually sparked that idea in the first place for BiggerPockets. He’s going to give us some really good tips for building an online community. So if you are out there building an online community, he’s going to tell you exactly how it’s done. Here’s something to keep in mind. It doesn’t, by any stretch, happen overnight.

Now, he’s also going to tell us how he took a big, gigantic step back from the company, but that ultimately led to him growing it in ways he never knew were possible in the first place, all right? And one thing you’re going to really love—make sure you stick around until the end because dude quotes Jay-Z. Yep, for real, can’t make this stuff up. So make sure you listen all the way through. You’re going to love it.

J: Okay, well before we jump into our episode with Josh, let’s hear a quick word from our sponsor.

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J: Thanks so much to today’s sponsor. Now, without any further ado, let’s bring on Joshua Dorkin, the founder of BiggerPockets.com.

Joshua Dorkin, welcome to the first ever BiggerPockets Business podcast and I promise that will be the last time I call you Joshua.

Carol: I may call you Joshua once or twice. I can’t lie.

Josh: I hope you call me Joshua. Hey, Jay. Hey, Carol.

Carol: Hey, Joshua. It’s good to see you, Josh.

J: It is great to see you. I have not seen you in a while.

Josh: Yeah, great to see you guys.

J: So Josh, this is not the first time you’ve been on that side of the microphone for a BiggerPockets podcast, but it’s the first time in a while. So let’s start with, what’s new? What’s going on with you? I want to jump into your backstory but first, I want to know what’s going on today. Why haven’t we seen you much behind that microphone in a while?

Josh: Sure. So you guys haven’t heard from me in a while or seen me in a while because I’ve stepped back from the business. After 14 years. We had what we might call an event and I stepped away November 17. We had gone through some pretty serious family stuff. My daughter had a routine surgery that resulted in lots of complications and required an emergency surgery.

Afterwards, all in all, the chaos and I don’t know—being nine and going through all that is pretty horrifying. And so she developed something called a Conversion Disorder as a result. And it’s kind of like a PTSD response, but in her case, that resulted in her being essentially paralyzed from the neck down.

Carol: I’m sorry.

Josh: Yeah, yeah, yeah. So starting the end of November, and I think this might be the first time I am actually probably talking about what specifically happened here, but you know, after the first surgery, I went to surgery with my kid and things just weren’t normal the next day. So I never went back to work. And for the next months, my job was to care for my daughter. And she was just nine, a 60-pound kid. My wife couldn’t carry her around and take care of her. I mean, she could but we had to physically move her around and do things and so that really became my job of rehabbing her and being there and helping, you know, my wife and being there for my family.

So, the reason I disappeared from public view was the first core value of BiggerPockets, which is family above all else. So I had to step away. Thank God, call it February or March, we started to see her begin recovering pretty dramatically. Yeah. And two weeks before the end of school, she was actually physically walking into school. I mean, she had gone to school in a wheelchair and walker and all this stuff, but yeah.

And since then—that was about a year ago, we’ve been focused on continuing to rehab her, getting the family kind of back together. Really just trying to reacclimate everybody, because I have two other kids. But as a result of that, everything we went through, I think any sane human being would reevaluate their priorities. It’s just, what’s important to me?

J: I want to talk all about that because there’s a lot to unpack there. I mean, there was your family life. There was your business life, and I know the horrendous stuff that went on in your family life. Looking back, I know I’ve seen pictures of her on Facebook recently and she’s looking great. She’s looking like she’s getting healthy again, so there is certainly the bright side of she’s recovering, which is fantastic.

But there is also a lot of some bright sides in the business and some changes in the business as well that affected you. I want to get to that. But there are probably some people on this podcast right now that maybe didn’t start with BiggerPockets. They are maybe not familiar with what you’ve done and the business you’ve grown, at least not as familiar as some of us are. So if it’s okay with you, I’d love to take a few minutes and step back and then kind of build to what specifically happened. Is that good with you?

Josh: This is your show, man. I’m not going to hijack it.

J: Excellent. So let’s—

Josh: All right, back to the show—

J: So let’s start with, for those who aren’t familiar with, Joshua Dorkin—Josh Dorkin, who are you and where did you come from and why are you here with us today?

Josh: Sure. I think I’m here because of my charming persona.

Carol: Absolutely. Without a question, Joshua Dorkin, that is why.

Josh: No, I’m here, I believe, because I created BiggerPockets. And to those who are unfamiliar to BiggerPockets, it is the greatest collection of real estate investors in the world. You know, I’ll rewind and explain really what that means, but about 14 years ago—I had been floundering around. I was in the entertainment business. I was a failed actor. I’ve failed a lot of things. Failing is good. If you failed, it means you’re trying. I went to college in St. Louis, Wash U. I grew up in New York. My parents were entrepreneurs.

J: What did your parents do?

Josh: Mom had a retail shop. She was in the fur business. Dad, electrical contractor. So I grew up watching these people, and then aunts and uncles and everyone else was kind of doing their own thing as well.

Carol: So you were all in that similar mindset.

Josh: Oh yeah. And you don’t have to tell somebody, go and be an entrepreneur. If they grew up in it, I think it becomes almost innate. So, post-college, I became a stock trader. Burnt out pretty quickly on that. Became an actor because I always wanted to do that as a kid. I ended up digging into that business and exploring every component of that business. I was in the casting side. I worked in production, in management, in agents—I worked on all sides of that business, mostly in crummy roles, but you know, at the very least, I was exploring it and learning it because I wanted to know as much as I could.

I think the idea of being a janitor is how you learn a business. You start at the bottom and you work your way up. So I did that. Entertainment brought me out to California. In California, I decided I was going to quit that business because frankly, there’s like this differential between California and New York, in the entertainment business. In New York, they’ll tell you eff you to your face. In California, they’ll smile to you and as soon as you turn around, they’ll stick a knife in your back.

J: Now, before you quit the business, I need to mention, I’m going to do my absolute best—

Josh: To dig up all the—

J: So Josh has a clip out there somewhere of him as an extra on Saturday Night Live with Jerry Seinfeld.

Josh: Oh yeah. It’s out there.

J: So I’m going to dig that up and put it in the Show Notes.

Carol: I’m so putting that in the show.

J: Everybody check the Show Notes.

Josh: I’m glad you know about that clip so you won’t dig up the others.

J: Yeah, I’m on a mission.

Josh: So, I’m in California. I was in and out of the business, was looking for ways to make some money, knew that back in college, I was into real estate, and went and got my real estate license. Didn’t love it. I didn’t love the sales side of the real estate business for lots of reasons, but went through two different stints just doing that. Just looking for some cash.

I ended up getting a substitute teaching credential and one day, I happened to be dating this girl, whose family was running a school. Her mom had started the school and she had worked her way up. My girlfriend at the time—and they needed a substitute teacher. So she knew I had the credential, called and said do you want to come in and work? And I did. The day I came in, the teacher that I was subbing for quit. And I was dating this girl so I couldn’t say no when she said, want a job?

Carol: It wasn’t exactly an option. But I just want to point out something that I think is fascinating, that the girlfriend, of whom you speak, happens to be your wife now, correct? Fast forward.

Josh: She is my wife.

Carol: And isn’t it an interesting coincidence that her mom, did you say, started the school?

Josh: It is.

Carol: So, Julie comes from an entrepreneurial background, too. So that sounds like she gets it, right? So I am hopeful that we can get into later as we talk more, how important that was in supporting this whole entrepreneurial journey.

Josh: Oh, I mean. It’s insane. She put up with so much garbage, it’s not even funny. So yeah. We’ll talk about it. And now I’m a full-time teacher and one day, my brother calls me up. And he says, hey Josh, I’ve been buying property and I think you should look at the numbers. And I was like, wow, this looks great. Very exciting. I had always, again, been into real estate but never had the nerve to do anything.

So I got on a plane, flew to where he was in St. Louis, and I started looking at property. And it was like, wow, these are really cheap properties, because they were. And I was like, you know what, I’m going to buy some. So I had been saving money. I had a couple of buildings. And I was ready to get rich. I was excited and I was teaching and I had these properties and got managers to help me out, and little by little, problems started popping up.

I was 2000 miles away and the ability for me to deal with those problems from 2000 miles away was a serious challenge. So I found myself in a position where I’m like, what do I do? Hey, some tenant just stole copper out of a vacant unit. Now, what do you do? So you go to the bookstore and the books don’t really talk about that.

You go online, or at least I went online, and I found there were a few communities that existed, but I felt that the business model of those communities was not to necessarily help me to be successful but was to put me into a funnel to buy some kind of expensive materials—courses, bootcamps, webinars, seminars, and all these things that were going to drain my pocket instead of actually helping me out. So I said, I’m not going to do that.

Well, what am I left with? I don’t really know any real estate investors other than my brother. He can’t necessarily answer all of my questions. My agent that I talk to doesn’t know anything because most agents don’t know anything about real estate investing. So I was in this position where I’m like, what do I do? Back in college, I started building websites for fun. Just, the internet was beginning to blossom then.

The internet was in the beginnings of the graphic web when I was a freshman in college in ’94. And so I had some experience and I said, you know what? I’m going to start to gather as much info as I can online about real estate investing to help me. I started to put together tools, resources, and then I was like, you know, it’d be really cool if I could create some kind of community. So I didn’t really know how to program beyond really basic web programming and something called html.

So I was like, I might as well learn. I learn everything else I know. So I went and I found some software that I can build out to create a forum, so like an online community, and that was kind of the beginning. That was the origin. I had this cool domain name, BiggerPockets, and now I had to go and find people to help me answer my questions about real estate and then I had to figure out how to attract people to stick around and thus began the quandry, the dilemma of like, how do I build this business?

And by the way, it wasn’t designed to be a business. It was literally this hobby site on the side to help me stop failing as a real estate investor.

Carol: So, you had this need. You had this idea of building a community at a time when they are really—I am trying to think back to that, when there really wasn’t that many online communities at the time, right? So you said you went out and talked to other people, found other online resources. Do you recall where you went or how you went about gathering these people to the community?

Josh: So, the resources were easy. I just Googled every—well, did I Google? I don’t even know if I was Googling. I might have used Meta Crawler or Dog Cloud, but you know, I found those. That was easy. Getting people to come was the hard part. And I didn’t—there was no manual. There is no like, today there are sites like Pat Flynn and all these entrepreneurial websites to teach you how to build a community. Back then, there were communities of people who built websites.

And a lot of them are still around, Site Point, Web Pro World, and so I would go to these communities, just learn what other people were doing and I realized that they allowed you to create—it’s called a forum signature. So at the bottom of all your discussion posts, you can—call it a mini-blurb, right? And so what I did was I wrote, “BiggerPockets, Real Estate Investing Community”, and I put a link.

And I noticed by looking at my statistics, as I posted in these places and asked questions, people would show up to my site. And I was like, oh, okay. That’s cool. Well, what if I went to—they all had an area called “Off-topic”. So you know, if you’re nerding out on web design or if you’re nerding out on something else in a community, typically there’s an “Off-topic” where you can just ask a random, post a random question, comments. So I would go to the “Off-topics” and I noticed that there were discussions about money and finance and randomly, real estate.

And I was like, oh, I wonder if I answer these questions, if these people will see my signature and then be enticed to then come and visit my community and then participate there. And so I started to do that. So, little by little, that worked. That, in combination with maybe there was kind of a fake user or ten talking to each other in the very, very, very beginning, asking and answering their own questions—eventually, there were people that were not me—

J: I think something a lot of people don’t realize, if you’ve never built a community or if you’ve never really thought about communities, there’s this thing called “Network effects”. And network effects is basically, until you have some level of critical mass, until you have enough people writing questions and answering questions, you don’t get that organic growth.

So if you walk into a community, there are five other people, you’re not going to post anything because you don’t expect a good answer. And if there’s only five other people, you’re not going to answer a question because you’re wasting your time. And so, all communities are either going to get to that critical mass, that tipping point where they are self-sustaining, there are enough people to draw other people and they continue to grow where they don’t get to that point. Or they shrink and they go away.

So it’s real easy, and I’ve seen a lot of community developers over the years who will start a community and if in three or five or ten months, they don’t have critical mass and they’re not growing, they just give up. So can you take us through the growth of BiggerPockets? I know it wasn’t quick.

Josh: It took forever. It was a very long time. I think that first eyeball to the site, that first user that came independent of me telling my mom and brother to show up and they laughed at me. And my friends, who also laughed at me. My parents didn’t really laugh at me. They just said, what the hell are you doing? Find a job. So I’d say, the first time somebody posted on the forum, that was not me posting questions, was exciting, right?

Carol: You were like, yes, finally. I got this.

Josh: Yeah, and then the first time somebody posted something and somebody else answered it, other than me going and researching the answer and answering that question from somebody was also magical. But it took two to three years, probably, before we got to the point where I didn’t have to be involved in every conversation for it to continue, maybe even more. Again, I don’t remember when we got our first moderator, but one of our earliest users was a guy named John Holdman, who is a moderator of the community today, 14 years later.

Carol: That’s awesome.

Josh: He fell in love with what we were doing. And what we were doing was special and the reason people came was, there was nothing else like it online or off. There was no place where you can go post questions, get answers, and not have somebody sell you something, right?

And to this day, still, if you go to most communities, you have a question—how does an ARM loan work? Which is an Adjustable Rate Mortgage loan—how does that work? What you’re going to get is maybe one or two people answering, and then a lot of people saying, hey, I can get you an ARM loan. Or I can get you an ARM loan. In other real estate communities, that’s just how it worked.

So we established a set of rules that a lot of people really didn’t like. It pissed people off because nobody else was doing that before, and it angered people who thought they were entitled to do that anywhere they wanted to. And we said, no you’re not. This is not how it works here and do that, and you’re gone. Now, everyone else was like, holy crap! This is amazing.

I can go actually ask my questions and not be afraid that somebody is going to pitch or sell me. And, there’s no stupid questions. I can ask a question as dumb as possible and I’m not going to get made fun of. You know, so we took all these ideas that I had in my mind and said hey, let’s go apply this rule set to what BiggerPockets is. And then turned it into something really, really special. And over time, this thing—we got to the network effect point.

This is four or five years, and this is a really important point that I think we need to drive home. Anybody that’s on Facebook these days, anybody in the marketing community, the real estate community, were constantly bombarded with the message that if you get up at 3:00AM, if you work hard for 20 hours a day, if you don’t have a social life, you’re going to be rich in 6 or 12 months. And maybe the gurus don’t actually say those words but that’s basically the message that’s in your head, that if you work hard, you’re going to get rich quick.

And as you saw, that’s just BS. I mean, we have this generation of budding entrepreneurs who are terrified of working their butts off for five or ten years because they think if they haven’t gotten rich in the first three or six months, they are doing something wrong.

But that’s not just their fault. But at the end of the day, and you said, gurus. I mean, that’s the venture capitalists. That’s the angel investors. That’s the tech media. That’s the press. Everybody’s pushing this idea that Facebook and Insta and all these things, yeah, they grew from nothing to mega-billion dollar companies.

And if you create a business that, hey, you know what, if I go and create a business that makes a million bucks or if I create a business that creates $100,000 from my family for a year, that’s unsuccessful. That’s what’s happening today and that’s horrifying because I go into rooms with entrepreneurs and I see these people saying, well, I’m going to build a billion-dollar business. And if they don’t, they think of themselves as a failure.

Carol: Those first two or three years, you were teaching as well as being so involved every second of every day when you weren’t teaching, on BiggerPockets. Is that accurate? So for those first two, three, four, five years, realistically, how many hours a week were you working?

Josh: So I quit my job teaching after two years. Two years after I started with BiggerPockets. So when I quit after two years, I was not making money of even remote consequence. Right around then, I also got married. And my wife was willing to put up with me making bupkiss, really. And supporting us and I always had saved my money. I never spent it on you know, dumb things.

But to the other part of your question, I was working—I would get up in the morning. I would start working then we’d leave, we’d go to work. Whenever I had a free period, I was working. On a lunch break, I was working. So I was probably putting in 40, 50-hour weeks concurrent with my 40-hour or so teaching job, on BiggerPockets.

Carol: And then after two years, you finally quit. Once you quit your full-time job, let’s see, did you cut back in your hours? I have a feeling the answer to that is a big resounding no. Not even close. It’s always, let’s go and make this happen, right?

Josh: Let’s go and make it happen. And mind you, I was probably in the first two years making a penny an hour, maybe. Or less. And you know, that did not drastically change immediately. I mean, it took a long time for that revenue, that income to grow for the platform. There were various phases of this business. It went from hobby site to lifestyle business, which was kind of when I quit my other job.

And now I had this lifestyle business. Now, mind you, I did not have a lifestyle business because I had no life. And then I got to the point where I hired my first employee and it became an actual business. And then the final phase was something that I know we will get to which was, November of last year, where I brought on a partner, and this business is now in full rocket ship mode.

J: I want to talk about the first hire a bunch but before I do, I just want to touch on something that I’ve always wondered. I’ve been a part of BiggerPockets. I’ve been a part of the community for over a decade now, and something that has always stuck out—

Josh: Thank you for that, by the way.

J: Thank you. So if I do my quick math, basically what I get to is you were in this business for about 10,000 hours before you were making enough money to even say, I can quit my job, maybe even longer before you were making the same amount of money.

And you made the early decision to kind of put your personal values that we’re not going to have gurus, we’re not going to have people selling on the site, we’re not going to sell out above your profit. You made that decision. And it probably would have been, and I know later, like 2010, 2012, 2015, after BiggerPockets started to explode, it would have been really easy to sell out and just make quick money. But you never did that.

Josh: It never crossed my mind to do it.

J: Really?

Josh: At no point did it cross my mind. Now that’s not to say that there was not a struggle. I think the struggle was where’s the line? So what’s the black, what’s the white, and where’s the gray? Because you know, we have to turn this into a viable business. So how do you make money without crossing any kind of line?

And that was the struggle that I dealt with and we dealt with and you know, the company will hopefully forever deal with. Is that line well-defined? I’d say there’s a definitively a fuzzy gray, and my rule has always been, stay the hell out of the fuzzy gray. I think there is a difference between values and pivoting on tactics and strategies. I believe that you establish your core values, who you are, what kind of business person you want to be, what kind of business you want to run, and you stick to that. Look, core values create culture.

By the way, I thought all these words were bullshit, five, six years ago. Like, I didn’t get it. I didn’t understand it until we got to a point of scale where we got 20, 30 people working at the company and all of a sudden, chaos and potentially people who weren’t good fits were working at the business and I’m like, why? So those, you cannot—I believe you can’t shift from in terms of strategy, tactics, like hey, you know, we tried this, and it’s not working. Okay, we’re going to change. That’s cool.

Like hey, we’re going to build out a book business but it’s floundering and failing. Well, hit it from a couple of other angles and give it your all. And by the way, today most people is all like, I’m going to give it a week or two and if it’s not working, I’m going to quit. Or a month or six months. I don’t think people realize that you’ve got to try. That’s not trying. That’s baloney.

Most people who start a podcast quit after five or ten shows. They have three listeners and they’re done. But guess what? The 11th show was the one where you were actually going to be successful.

J: You touched on something. You started talking about culture. You started talking about building teams. I want to jump ahead a little bit. And this is something I know a lot of entrepreneurs struggle with. I’ve struggled with it. I was there when you were dealing with it so I know you struggled with it, too. And that’s making your first big hire. You started the business in 2004. I’m going to kind of do a spoiler here. You didn’t make your first big hire until what? I think it was like 2012?

Josh: ’12 or ’13.

J: I was there. We were having discussions when you were talking about hiring Brandon, and you were talking about, oh—I have to carve out equity. I need to get somebody really vested in the company, somebody whose goals are aligned with my goals, aligned with the company’s goals. And to do that, I have to do more than just pay a salary.

I have to give him equity. I have to give him stock. And I remember, that was a struggle for you. So can you walk us through a little bit about how you decided it was time to make that hire, the struggle you went through to make that hire, and ultimately how it led to where you are today with 30-40 employees?

Josh: I would say, the struggle was, I again never started this with the intent of building a business, right? It was a hobby and then the hobby began this lifestyle business. Now, I ended up needing contractors because I was a hack of a coder. So I needed contractors to help me code. By year twoish, year and a halfish, hired a team of contractors. They sucked. I mean, it was terrible.

Carol: When you say terrible, tell me how terrible.

Josh: I mean, I paid like—total of $15,000-$20,000 for this outsourced shop. I was living in L.A. to build out—when we went from forum to build it into the “MySpace” job. Hey, MySpace was hot. So I was trying to build the MySpace of real estate investing and I blew $15,000-$20,000 on the development of this and I got back a chunk of code that didn’t work. It was garbage.

And I had never worked with a team like that. I didn’t know how to do milestones and make sure that things were working—I just waited until the end and got back a product that was broken. And my money was gone. I was like, okay.

Carol: Wow. Not a good day.

Josh: No. One of the many bad ones. And that was the day where probably 98% of people would have quit.

Carol: Why didn’t you quit?

Josh: Because as Jay-Z said, “I’ve got only one rule. I will not lose.” I don’t like losing. I don’t like having other people be the cause of my own failure. I can’t let you dictate my success or my failure. I am going to be the only one to dictate my success or my failure. So I was like, okay. Put your big boy pants on and find another way to do it.

Now, I had no money at the time so I had to go back to zero, start building up money to be able to do something and I came in with another strategy, which was instead of building this massive MySpace-like thing, I’m going to take one tiny piece of it, hire somebody to build that tiny piece, and little by little, piecemeal by piecemeal, we’re going to build it up.

By the way, there is now a word for that. That’s called lean startup. I didn’t know what lean startup was. The word didn’t exist. But I had no other way to go about doing things. 

Carol: And what an amazing learning experience, right? That’s what we talk about as entrepreneurs. We take those things that can be seen as the big failures and frankly, for whatever it’s worth, Jay and I, we talk to our kids about this all the time. Around the dinner table.

We’re like, okay, what was your favorite part of your day? What was the best thing that happened today? And most importantly, we really hammer out, and the teachers freak out about this—you say those words to your eight and nine-year-olds? We’re like, yeah, we do. What did you fail at today?

If they can’t come up with anything like, you have to go out there and make a mistake and then tell us about it. Because it helps you learn so much, right? Look into ways of doing stuff.

Josh: Yeah, absolutely. I know there was something else I was supposed to answer in there, but you know—

J: I want to talk about Brandon. You hired Brandon?

Josh: Oh yeah, yeah, yeah.

J: I remembered that took months because you were struggling. So tell us a little bit about that.

Josh: So I had the experience with these contractors and so the hiring of Brandon came at a very interesting point inn the business. You guys have asked a lot about this long journey—so there were a lot of days in those eight years where I was just miserable. I was like, why am I doing this? This is just stupid. I’m not making any money. I had met with VCs. I had gone and met with angel investors. Never like seriously I’m going to go raise money but like, hey, is it possible? What can I do about this business model, blah blah blah.

And throughout it, they are always like, you’re crazy. This is not a viable model for continued success. Maybe there are other ways to go make money. I was watching my friends who graduated from college with me, making very good livings, doing very well. And I’m 30-years-old. 29, 30, 31, 32. And I’m really struggling. I mean, I’m barely making any money. I’m barely. What’s worse than a teacher’s salary? Mine.

Yet, I’m continuing through it because I see that I’m helping people. I know, in my soul, that these things are going to be successful. I’ve just got to figure it out. And so, I got to a point on year eight where I just, you know, I turned to Julie and I just started bawling. I mean, absolutely bawling. I was miserable. I went seven and a half years without taking a day off.

By the way, this is not like, I’m not bragging about this. This was stupid. I went seven and a half years—I didn’t take a day off. When my kids were born, I brought my laptop and I worked. When I travelled to see my family, I took my laptop. I never had a vacation because I worked every single day for seven and a half years, which is very stupid, by the way. Don’t ever do that if you’re listening. Days off are very important. I felt trapped.

So the reason I was bawling and crying to my wife was, I was beyond burnt out. I was trapped. I could not escape my business. I became a prisoner to this business. And I didn’t know what to do so I ended up hiring a consultant, a guy I knew in the real estate industry who was just a wicked smart guy. And I hired him to look at this business. Tell me, should I quit? Should I just shut it down? Should I sell it? Or should I move forward, and if so, how the hell do I do that?

I never wanted to take on debt. I never borrowed money to start the business. I started the business with the six dollars it cost me in hosting. That was it. And my sweat equity. I mean, I invested $6 to build, you know, a company of huge magnitude and that’s all it took, was just hard work. So when he came over the course of a couple of weeks, looked at the business, and broke it down, realized that I had kind of gone off the rails on certain parts of the business we had built, what we call a feature bloat.

Too many features that weren’t very successful and we didn’t have the management to kind of handle them because I was the management. We were the management. I always use ‘we’ when I talk to people about the business. ‘We’ was me. That’s how I looked big. I had people thought we were dozens of people. We were one people but—

And he said, he was like, Josh, you can do any of the above but given your model, I think this thing has legs. You’re now making, after year eight, enough money where you can probably squeeze out somebody. You’re going to have to eat some ramen noodles for a while. And so, we went from—we found Brandon and I was very scared. After eight years doing it by myself, trusting somebody to come in was scary.

But we kind of dated. Brandon was writing for BiggerPockets. He was an author on the platform. We became friends, chitchatted for a while. Then he became a contractor for a little while and then he became an employee. He lived across the country. But he and I immediately began working, continuing to work 100-hour weeks, but it was like this exciting, exciting phase. He got paid very poorly. Making up for it now.

But he took a risk. He didn’t need to work for me, was the thing. So I got lucky. I found a guy who was a success story of my platform. BiggerPockets allowed Brandon to become financially independent at the point at which I hired him. So he didn’t need a job. He wanted the job. He loved BiggerPockets and so what better person to bring somebody into your company than somebody who loves—

Carol: That’s the ambassador you could have asked for right, somebody so involved, somebody who has made so many connections on this site, somebody who has truly built this livelihood as a result of the hard work you put into your site, is the best brand manager you could ever ask for to go out and sing to the masses, come to BiggerPockets, come to BiggerPockets, come to BiggerPockets.

Josh: I know a couple of other people like that.

J: Let me point out that I think this is actually one of the biggest reasons BiggerPockets has been so successful. The way you’ve fostered your relationship with your members, there’s this mutual benefit between you, the owner, the site. Everybody that’s running the site, and the people that are contributing. And there are several members, Brandon is one. I’m certainly one. We’ve literally built our brand and our livelihood and our careers on the back of BiggerPockets.

You don’t often see that with other social networks. Sure, people can carve out a little name for themselves in forums or whatever, but literally, I can name a half dozen people on the site that have built their brands because of BiggerPockets. And the mutual benefit between the company and its members, I believe, is a large portion of its success.

Josh: I agree.

J: Yeah, and you deserve full credit because you’ve been so giving with allowing your members to come in and you ask a lot of them and you give a lot back. And it’s that synergy, that symbiotic relationship between you and the company and the members that has made both sides tremendously successful.

Josh: I agree. And by the way, you can think of a half dozen, I can think of dozens and I’m sure there’s thousands. Which is crazy.

J: Absolutely.

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Carol: You brought Brandon on, and when you brought Brandon on, would you say it was one of those moments where the sky opened up and you were like, there’s a light at the end of the tunnel. Was it that hire, or was it at another point where you’re like, wow, I can really take it somewhere else and maybe contribute a little bit differently and see where this thing can really go?

Josh: So it was that hire. Brandon, for me, was that person. You know, I look at all the people I’ve met in my career, you guys included. And Jay, you’re one of the smartest people I’ve ever met. I mean, you are absolutely brilliant and I have more respect for you than I think you will ever know and there are a lot of people like you out there that I know. 1If I did not hire Brandon, I don’t know that BiggerPockets would be what it is today. 

Carol: Awesome. Major shout-out, Brandon.

Josh: I mean, well—he’s such an amazing complement to who I am, which is I think why it worked. I only wish I had found him when I started, but I wasn’t trying to build a business at the time. So the two of us would spend countless hours, like teenage kids on the phone brainstorming. Talking, being creative, and just chitchatting about ideas forever and ever and ever, and which is why we are as successful as we are.

First, we did that. Then, we would actually try the ideas. Half of them would fail. The next one would be successful. We’d push at it and then we’d do the next one. And then we’d keep going. And so he allowed for me to step back a little bit. I went from 100 hours a week, every single week, to 90 hours a week. I mean, free time like there’s no tomorrow.

Carol: Wow. Good for you.

Josh: It was amazing and really, I would say, that’s when BP went from a lifestyle business to a company, right? I would say, the next hires, and there were a few of them—Hillary and Allison and Scott and Rob, I really kind of lump those guys in the next phase together. That began like this small core of a company.

But the willingness of people to take a risk on something like BiggerPockets. The willingness for folks to take a risk and work for a small company. Not just tech but like any kind of small company is not to be understated. My brother’s been laid off I think four or five times from tech companies, and he keeps going because it’s fun, it’s exciting, it’s new. Right? You get something out of the lack of stability at these companies. Some people like it and some people like big companies, but I’m very grateful to all those people who were willing to take those risks.

But eventually, I’d say, Scott Trench who is CEO of BiggerPockets today, host of the BiggerPockets Money Show, author of Set for Life, and an all-around amazing guy—he brought something that Brandon didn’t bring, which was, get a goddamned life, Josh. Brandon is like me, willing to slave away countless hours for little reward, hoping for future rewards. Scott really started—he’s the guy who yelled at me to take a day off. Scott would repeatedly say to me, this is your money, Josh. Why don’t you take some money out of the company? Years later, when we started to make real money. And I said no, it’s the company’s money. And we literally would argue and fight. And he’d say, dude. This is why you’ve worked for 12 years, 10 years, to be successful. I needed somebody to actually explain that to me because I felt I was wronging the company by actually withdrawing the money, not reinvesting every single penny back in the business.

Carol: When Scott came along and you started hiring the second wave of people to really start ramping things up even more to the next level, how are you feeling personally, as a founder of this thing, relinquishing so much of that control? Like, I remember, for example, back in the day when I had to go to a job that wasn’t our own business.

When I built out big teams, there were so many things that I miss about the day-to-day being in the business, but I realized that for my team to be successful and to grow our function, that I needed to work on leadership and development. But at the same time, I kind of was bummed that those guys got to do all the cool stuff. So how did your thought process work kind of emotionally when you were really—you were so in it every day, every little aspect of it and then giving some of that up?

Josh: So that, it was definitely hard. I think the real challenge came when, I don’t know at the very moment that it happened but, we got to a point where I was managing, I think like 11 people or 12 people or 13 people or something. I was the only one. Like, we need to change this. I started learning hey, you can’t manage 13, 15, whatever it was, people successfully and run the company, you know.

So we went and we created this management layer. And that was very hard for me. That was way harder than handing off part of customer service to somebody or blog editing to somebody or the finances to somebody. That was actually pretty hard, the finances. But handing that off and creating management was very, very, very challenging.

And I think we did our best at it. I think it took a while for us to get good at it, all of us. And I definitely struggled with it. I would say, after that, there was yet another wave of hires where I think we slightly stepped away from our core. Hiring is a huge thing. I’ll admit, I was like an education snob for a while. And so I said I’m never going to hire anybody who doesn’t have a great degree from a great school and then I kind of had to shift that because that’s hard to do.

I’ve found that some of my best hires actually did not have a college degree when I hired them. We have a few people who finished those degrees while working for us. All in all, what I’ve learned is, people who are passionate about your business are going to be your best hires. And you know, I’ve gone and hired people from Ivys who turned out to be terrible hires. They were super smart and knew everything. Yes, they were. They were actually very smart and yes, they knew a lot. However, they didn’t know how to work for us. They didn’t care about who we were.

J: I think in the big company world, there are these things—in the tech world, they have these employees where when companies get to 20,000 or 30,000 or 50,000 people, they start hiring these people in the tech world that are called evangelists. In the non-tech big company world, they are often called brand ambassadors. People whose jobs it is to basically go around and be seen wearing the clothes of the company and do good things, kind of make the company look good on a grass roots level.

And I see these too many companies where they wait until they get to 30 or 50 or 70,000 people before they start really encouraging these employees to be brand ambassadors or evangelists. BiggerPockets is filled—I mean, 30-40 people right now, and it’s filled with 30-40 people who are the company’s evangelists, the company’s brand ambassador. Everybody in that company is excited to be there. When you see them at conferences, when you see them at seminars, when you talk to them on webinars or whatever, everybody is excited to be a part of BiggerPockets.

So when you say that you were just as focused on hiring people who were excited to be part of the company versus having the education, it seems to me that that’s even more important. People can learn the job. People can learn the technology. People can learn the business. You can’t learn enthusiasm. You can’t learn love of company. I think that’s part of why BiggerPockets has been so successful is because you’ve hired the type of people that are going to make everybody else fall in love with the company.

Josh: And that’s part of the hiring process. You know, that comes through in the hiring process. My philosophy has always been, I want to hire people. Like you said, I want everybody at my company to be the people who are at the conferences, who are capable of leading sessions on the area of expertise that they are in. And I want to encourage them to do that because frankly, a lot of people are afraid to get their people out there. A lot of people are afraid to train their people.

What I say is, if I knew, if I help make you successful, if I help build your personal brand within your own field of expertise. If you go and you decide you’re going to lead BiggerPockets, you’re going to go and be successful. And you’re going to look back and you’re going to say, you know what? That was a great time in my life. That was a great company. And you’re still going to recommend us, right?

So I think that has worked. I think that has been successful and for me, there’s so many people out there. Why be selfish? Just be good and good will come back to you and that’s always been how we’ve run the biz.

Carol: Clearly, it has served you very well. And I feel like, through all this journey, it’s really come full circle because now we’re talking about, you’ve hired all these great people that really breathe BiggerPockets out of every pore of their body, right? And they are out there recruiting more and more people, building the business over and over so it’s self-perpetuating to a point where, back to the beginning of the conversation where this horrible thing happened with your daughter, you were able to take a back seat because you knew that BiggerPockets, this baby that you had built from the very first iota in the socket of the back of your mind because of a need that you needed to solve, you know that it’s in good hands and you were able to focus on your family. So it’s nice that you built this brand that really focuses on family first and you hired in such a way that enabled you to put your family first. That’s a beautiful thing.

Josh: Thank you.

J: Let’s jump forward a little bit and we get to 2017. You step away from the business for family reasons and then your daughter starts to get better and you chose not to come back. Can you talk us a little bit through what you were thinking there? I think some of us expected, okay, your daughter is getting better. He’s going to come back to BiggerPockets podcast. He’s going to start running the company day-to-day again. But you decided not to do that. So what was your thought process? What happened in that time?

Josh: Sure. This is that whole Jerry Maguire thing. I’m not going to cry. I’m not going to cry. So, rewind about, call it two years from then. I had talked about the bad hire. It was the mismatch hires. I mean, again. Not bad people. Good people, just mismatch. It created a lot of tension at the company. It wasn’t fun working there for me. I got to a point where I was questioning myself a lot. I know I love the company. I love BiggerPockets, but do I love my job? I am CEO of a big company.

I had talked to a lot of entrepreneurs before, tech guys especially, and gals, and everyone had said, just be aware there’s two phases and two types of people out there. There’s startup people and then there’s growth people, right? And scale people, really. And you know, I was like, you guys are full of it. I don’t get it. It’s the same thing. What’s the difference? So I loved zero to call it, eight, ten people. I mean, I love that phase. It was very fun, it was very exciting. Thereafter, I really did start to stop loving that phase of my job. And then scaling and management and dealing with that. Management meetings versus like get your hands dirty and do it, right? That, I did not like as much.

Not to say I wasn’t good at it. I wasn’t great at it—I got better at it. So I started hiring. I hired a coach. Worked with a coach. I think he was fantastic. Helped me out. Learned a lot. We kind of outgrew each other and then I ended up hiring another coach. And she was fantastic and really helped me think through a lot of things I was dealing with and worked through my challenges. Ultimately, I’d say, if I were being honest with myself at the time, and I was with the second coach, the first day I sat down with her, I started crying. Bawling, tears. I cry a lot, obviously.

With this woman I had just met, really. And I was crying because I realized that I was unhappy. And I didn’t really want to face it. I hadn’t wanted to face it for a while. And this was after—we had scaled and all this and I was like, well, does this make me a bad person because I love my company but I don’t like what I’m doing, necessarily. Well, let’s find a way to make you like what you’re doing. So we tried all this stuff and did all these things. Ultimately, I liked what I was doing more and more.

By this time, I wasn’t working 100-hour weeks. I was working 40-50 hours a week. I started taking my Wednesdays out of the office instead of being locked in the office. I was now networking on Wednesdays and using that time to think and plan and to strategize. So I was at home or out, which by the way, I recommend to everybody. Most business owners don’t put enough time in to think about the business. Thinking is work. Working, it was not just doing e-mail and responding, and dealing with people. Sitting down for an hour or two hours, four hours, a week, five hours, whatever—like that’s actual work. Thinking about what you’re going to do is work.

So I was doing that. I love that time. I love the big picture strategy stuff, but I just was not—I wasn’t super happy. So all this trauma happened and you know, Scott and Brandon, along with the other managers, Dave and Rob, were running the business. And I had to be real with myself. I had been away from the day-to-day for a while. I had a lot of time to reevaluate my life. I realized, as a human being, I was not happy.

And the challenge I faced was, I felt like a fraud. I felt like a fraud because my entire existence, my entire job for 14, 13 and a half years up until then, was to help other people be successful and find happiness, right? I talked to hundreds of people on the podcast about if you don’t like your job, start figuring out what you’re going to do next. And I never had the guts to do that.

And so that was where I felt like a fraud. It was really, really, really difficult. And mind you, I’m dealing with some heavy emotional stuff at the time. I mean, crying every single day, miserable. But finally willing to say, what can be worse than this thing that I’m going through right now? Like, if I’m going to be brave, look at what my kid’s doing, man. Now is the time to be brave. And I was like, okay. I don’t like what I do. I love my company but I don’t like what I do.

Carol: I’m sorry—that’s a big revelation but also, I think big to just admit it. Say it in your out loud voice, right? When you’re—I’d be like, I just don’t like this.

Josh: Yeah. That’s not to say that I don’t like being CEO. That’s not to say I don’t like the managing people. I think it’s a combination of a whole hell of a lot of factors. Fourteen years is exhausting. I think in that 14 years, I like to say I did 35 in 14. I probably worked about 35 years in that 14. It was about that time. So I chatted with Scott and Brandon and some of the other folks who I really, really trusted and said, what’s next? How do I transition? How do I get out of this? What do I need to do?

So we went and we hired an investment bank. I interviewed several and I hired an investment bank instead of a broker because the business had grown into the size at this point where you don’t just use a business broker. It was a pretty big business.

J: So just to clarify, a broker is somebody that would help you sell the business to somebody else. An investment banker can help you do more complicated scenarios where you don’t necessarily sell off the whole business. You can sell part of it and stuff like that, right?

Josh: Yeah, we could look at lots of options. There’s various possibilities from what you can do and you don’t necessarily limit those options. You kind of present who you are and you see who’s interested and what they potentially might want to offer to you, right?

So we hired a bank and you do what’s called a process. And the process is another word for a business proctology exam. It’s hell. It’s really, really hard. And it’s particularly hard when you have a 14-year-old business. It’s also particularly hard when you’re not building a business with the intent of an exit. So if you build a business with the intent of an exit, you’re going to do certain things in your administration and your paperwork.

You’re going to be organized in certain ways, which by the way, if you’ve got a business and you’re listening, or you’re thinking of building a business, you need to be as organized as you can with every ounce of paper forever. If you ever intend to sell because you will need to find every ounce of paper and everything that you’ve ever built out. E-mails, you name it. That’s the stuff. You need to know everything about every iota of your business.

J: This is part of the downside of you never taking outside investment. So you were never accountable to outside investors. Nobody ever asked you to prove the books or to validate every dotted I or crossed T. This is the first time in 14 years, basically, you’re going back and you’re auditing 14 years of your business for the first time.

Josh: Well, so we had done it before that because we just—I’m anal retentive. I’m Boy Scout and everything was on the up and up. However, it’s just like a process is literally like having your lawyers look at a contract written ten years ago and saying hey, is that contract kosher still?

So go through the process, looked at—had lots of folks interested in the business. You do these things called management meetings where your management team goes and they present and pitch the business to folks who are interested in the company after going through, signing non-disclosure agreements—it’s all a big—you can do shows on this whole thing.

But eventually, as part of the process, we met an equity group who expressed interest. And we really, really liked the team. We liked their philosophy. We liked who they were—

J: For those that are listening that don’t know, what is a private equity group?

Josh: A private equity group is, it’s a business of folks who invest in businesses. Their job is to invest in businesses and they invest, typically, large amounts of money in businesses. And their intent on a PE deal is typically, they want a return on their investment within typically call it five years. So if they invest x amount of dollars, they want some kind of return and they’ll tell you or not tell you what that is, but it’s generally several multipliers of what they are investing in a five-year period.

So we did what was called a recap. And a recap, for those people who don’t understand, it’s a recapitalization of the business and essentially, what it means is, they’ll go and they’ll invest some money in the business. Acquire a percentage of the company and the business will continue onward. They did not buy the entire business. I still own a significant piece of the business. They came in and they are now my partners.

J: They’re not a real estate company. They’re not like looking to define the direction of the business. Your team, the BiggerPockets team is still kind of driving the business. They are just kind of a silent investor who is saying hey, just make sure we get our money back and we hold you accountable. But they are not making the day-to-day decisions, are they?

Josh: So, since I am not in the day-to-day, I can’t necessarily answer that question. What I can say is, we picked this team because we felt that they were going to be very, very hands-off. And they were going to let us run the business the way that we wanted the business to be run, the future vision that I had for BiggerPockets.

Concurrent with that was the decision for me to officially step down as CEO of BiggerPockets. So, Scott, who was acting President at the time—he was President at the time, got promoted to CEO. I stepped down and stepped away 100% from the day-to-day of the business and my role became as guide and advisor to our management team, as now I call it, “The Godfather” of BiggerPockets, so to speak. And as a member of the board.

So in our case, it could be any range, basically, with a PE shop. You may have a PE shop who come in and they are very aggressive. They want to dictate every detail. And then there’s others who say, you know, do whatever the hell you want. In our case, they are pretty hands off and it’s great and the business is doing fantastic and exceeding expectations and it’s very, very exciting. But we closed in November of 2018.

J: So it’s been about six months.

Josh: We’re getting there. And that was horrifyingly scary. As much time as I put into my baby, being able to see it controlled was frightening. But I knew that the people that I had in place as my management team believed in the company the same way that I believe in the company and treat the business the way that I wanted it treated.

So at the end of the day—and finding a PE shop, who we’ve been very happy with, McCarthy Capital out of Omaha, who I believe has the same vision for who we are and what we should be. So I was willing to take a chance because like, we had met other people who didn’t necessarily have the same beliefs. And they did.

So again, it was very exciting, and thus began the next phase of BiggerPockets, which was professionalizing this business, bringing in the people who know how to scale the company, who have been there, bringing in advisors, and thus begin the next phase of BiggerPockets. It’s very exciting to watch as the company grows and I am forever an advocate of this company. I love BiggerPockets.

It’s my baby and I want it to be successful, not just because I still am an owner of the business, but there’s very few companies on the planet that are like this company. There’s very few businesses that changes people’s lives legit. And this is one of them. I mean, it’s amazing. So here we are.

Carol: I’m just sitting here and I am so grateful you are our first guest, because your whole story, your whole journey is so inspiring. I know BiggerPockets really well. I feel like I know you really well, but to hear it encapsulated like this and to just be taken through your whole entire journey from the very beginning through how you’ve grown it, how you went through your struggles and kept persisting, and how it’s on the trajectory, is now to hear it directly from you. It’s so inspiring and it’s just amazing being on this side of the podcast is cool, and I really think our listeners are going to be as inspired, if not more. It’s a phenomenal story. Thank you for sharing.

Josh: What’s cool is, I believe in my heart at some point down the line, this company is changing lives and it’s fun to watch.

J: BiggerPockets has achieved this one metric for success that a lot of time we don’t think about. You went from—you ran this company on your own for eight years. Then, for five years, you had a team of between one and 40 people. And then, for the last six months, you had a private equity firm that came in and is kind of managing it as a big business.

And yet, from the outside, as a user of BiggerPockets, all I’ve seen is continuity. When I came along in 2008 to what I’m seeing here in 2019, it’s the same company. It’s the same site, it’s the same quality, it’s the same giving back and so, people don’t know that for a long time, you were a single-person business and now you’re a big business.

And the fact that you can make those business transitions without your customers even realizing it’s going on behind the scenes, that’s an amazing thing. You’ve really kept true to your original vision and you have been successful with that vision. And a lot of founders can’t say that.

Josh: Well, you know, and I think one of the things that allow for that is, because of the origins of BiggerPockets being a place where it wasn’t about gurus, it wasn’t—for a minute there, at the very beginning, personality—I mean, I was the face of BP forever, right? We realized that was a risk. I didn’t want to just be the face. I wanted other faces. And then Brandon became the face. And he and I were concurrent—he’s still a face, the face, but you’re a face. We want this business to be personality-proof.

We want this business to be Google-proof. We want this business to be recession-proof. We’re trying to build a business that has legs. So when all this happened, it’s not about me. I’m not like hey, hey, hey—this is happening. We put out a release and let it go. I mean, the business doesn’t change. Who we are doesn’t change. We are the exact same company. We just have different ownership. Same management, but different ownership and pretty damn similar philosophy on where we want it to go. So why should anything change?

Now, that’s a successful transition, I believe. Many businesses where things could have ended—and I think there’s a lot of reasons that can happen but I’m grateful that in our case, we managed to really do it pretty seamlessly.

J: So what’s next for you?

Josh: Oh, man. Well, I’d say the first bunch of months were really transition months, working with the team on things. I’ve really been able to, I’d say over the last couple, to finally maybe take a breath. I still don’t think I’m necessarily there. In fact, we just got back from Hawaii. I went and visited Brandon, which was fun, the whole family. And I think I had the first moment, I mean, probably in decades where I just sat back, took a breath, and was like whoa. I mean, I truly—I would say maybe even in the last week alone, I’m not fully there but I am probably as calm as I’ve been in probably 20-30 years.

J: Well, they say, you should take a week’s vacation for every two decades you work.

Josh: I’m getting there. I’m getting there.

J: That’s awesome. Okay. This was great. Honey, do you have anything else?

Carol: Just thank you. Thank you for sharing. Thank you for being so open and it’s so funny that you recognize that you’re more calm than you’ve been in 20 years, because I can feel that from you. You’ve just got this air of, I’ve got this. I’m like sitting back, I’m watching the joy. I’m enjoying the hard work that I’ve put in and it’s kind of ‘me’ time. Your energy has changed. Your energy was great before but you’ve just got a different, more calm and confident energy. It’s awesome. Really nice.

Josh: And Jay, you did ask what’s kind of next. I mean, beyond just the relaxation and trying to figure out happiness, I think one of the things that I’m struggling right now, which I think a lot of people—it’s crazy. Since I’ve started thinking about this, it’s game-changing.

So last year, because of everything, I started thinking about happiness. It’s like, what is happiness? What does it mean to be happy? I’ve spent a lot of time thinking about it. I think I’m getting closer to that but also think about, what I like doing. And I’ve been asking my friends, hey, what do you like doing? And what’s funny is, most of them don’t remember.

Carol: You forget. You get caught up in your day-to-day.

Josh: 30-40, you’ve got kids or whatever, what brings you joy? We all stop thinking about that. Not everybody but a majority of people stop thinking about it. So I want to challenge anyone listening, take a few minutes and think about it and if you don’t know the answer, you better figure it out because I’m sitting here sadly, and I’m trying to figure it out. I know skiing brings me joy, my kids bring me joy. But like, what do I want to do? I just bought a guitar. It’s like, hey, I’ve always wanted to play guitar. So I’ve been teaching myself guitar. That’s pretty fun, actually.

Carol: That’s great.

Josh: You know, I’m looking at potentially launching a podcast of my own at some point. We’ll see. I’m thinking about it, trying to put it together. I’m looking to potentially advise non-real estate startups. I think I can use a little break from the space for a while. So look to do some advising of startup businesses. That’s kind of exciting for me, just the premise of doing that. You and I, Jay, have talked about that. I love that idea. And I’m also potentially—I’m looking at diving back in, because I took a break for so long, from real estate itself, to focus on BiggerPockets. I’m potentially looking to kind of dive back into my own investments.

J: If you’re ever looking for some real estate investing resources, I can recommend a few.

Carol: Yeah. I think we may have an idea on where to find some people who just might be more than happy to help you out. So all kinds of exciting possibilities ahead.

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Carol: So now, Josh, we would like to have you be the answerer of our first edition of what we are calling Four More. This is our version of the Famous Four questions that we ask every guest every week, okay?

J: Okay, question number one of the Four More. Josh, what was your worst job ever and what lessons did you take from it?

Josh: Worst job ever—there’s two that come up. So worst job ever was either I worked at a bagel shop. I did not last a day. I had to go between the freezer and the scalding temperatures of the summer, in and out, and like my body wanted to collapse after an hour. I was like, I can’t do this. I’m done.

Or, while living in Los Angeles and needing some cash—

J: This is going to be good.

Josh: I was a doorman, scrawny old me, for a Church of Scientology meeting. And there happened to be—I was just helping my buddy out, and that day, there was an earthquake. So I’m like standing at the door and that was the first earthquake I had ever felt.

Carol: At least you were in a doorway.

Josh: The windows, I’m outside of a glass building and things are shaking and like, scared the living bejeezus out of me and I like was on the ground and everyone else was looking and laughing at me and I’m like, I can’t do this, I’m out of here. So how about that?

Carol: That’s an awesome answer. So I want to ask, what is the defining moment where you realized you had the entrepreneurial itch?

Josh: I’d say there were two things. I didn’t realize it but when I was like 10 years old in my mom’s first shop and I was telling her how to run the business, it might have been the first inkling that I was going to be an entrepreneur. Or just an asshole.

Carol: We’ll go with option number one.

Josh: But you know, I would say, I really think I realized it at every job that I always had. I was never happy just doing my job. I always wanted to give input to the people who were bossing me around, my managers, and tell them how they can better improve the things that they were supposed to be doing as well. And I realized, I’m going to have a hard time working for somebody for the rest of my life. I probably need to work for myself.

Carol: Excellent.

J: Okay, this one goes back to my biggest pet peeve. There’s a whole lot of bad advice in business. We all hear bad advice all the time. What’s the worst piece of advice you’ve ever either been given or you’ve heard, and how would you correct that if you were to give that advice?

Josh: Oh, man. That’s a really long list. I would say, it’s all about the hustle. It’s all about the grind. And don’t get me wrong, I believe hustling and grinding and working your backside off is necessary, but I also believe that what I did was stupid, right? So I took the hustle grind mentality to the extreme. I didn’t take time off. I didn’t think about myself. I didn’t take care of myself. And that’s a bad thing.

So I would say, there’s balance. And part of the core values of BiggerPockets today are a result of that imbalance. Putting family—somebody at the company, for example, the only time you can get things done in a lot of industries is in the middle of the day. Shops close, things close, right? You have to get your car fixed. Go at 11 o’clock and take care of it and you’ll make it up later.

Like, a lot of companies, you can’t go and get your car fixed until 5 o’clock. But if at 5 o’clock, you’re picking up your kids, you’re dealing with dinner—it’s unreasonable, at least in my mindset. Anyway, I mean, we can do hours and hours and hours of the bad advice that I got or that I’ve heard. But that’s the quickest one that comes to mind.

Carol: That’s a great one. So I have a fourth question. I like to spend money, so my last question is, what’s something that you’ve splurged on? What’s been totally, totally worth it?

Josh: Man. I’m like the anti-splurge. I don’t like to spend money on myself. I don’t mind spending money on my family or other people. I really don’t like to spend money on myself. So, I would say my Jeep. I bought a Jeep after everything went down. I didn’t have a car because the company car was my car. I needed a vehicle. I got this bright orange Jeep I’ve been driving the last couple of days until today, with our pending blizzard, with the top down. It’s been a blast. Yeah, that’s it.

J: That was the Four More. So now I’m going to ask you for more. Where can our listeners find out more about you?

Josh: Find me on Twitter @JRDorkin. That’s probably the best place. I’m on Instagram, Twitter. I’m not on LinkedIn anymore. I may not be on Facebook anymore. We’ll see. I’m on there but barely hanging on. So Twitter is probably the spot. But yeah.

Carol: Do you want to give a shout-out to your book, by any chance?

Josh: Well, can I give a shout-out to my company?

Carol: Absolutely.

J: Have we heard of them?

Josh: So I’ve got this company that I own a piece of, it’s called BiggerPockets. It’s amazing. So really quick, for those of you guys who are listening who don’t know what BiggerPockets is, beyond, it’s a community, it’s resources. We’ve got several podcasts, including this one. We’ve got a publishing business. If you want to change your life, if you want to better your financial well-being, not just necessarily through real estate, just in general—check out BiggerPockets.

Listen to The Money Show. Check this show out. The BiggerPockets real estate podcast. Check out some of our—I don’t know where we’re at—16, 17 books on topics from money to real estate. It will definitely change your life. And get involved because there’s amazing people like Jay and Carol and all the various people who give up themselves to try and give back and help other people be successful.

J: And hold up your most recent book. Thank you. And this—

Josh: How to Invest in Real Estate: The Ultimate Beginners’ Guide to Get Started, written by myself and Brandon Turner. It’s pretty much the first book. If you want to buy a book on real estate, this is the first one to pick up. If you want a book on estimating the costs, you buy Jay’s book. If you want to buy a book on flipping houses, you buy Jay’s book. We’ve got rental property. We’ve got books on every topic in real estate. Check out BiggerPockets..com/store if you want to check it out.

Otherwise, you guys, I’m so excited for you. This is going to be a lot of fun. You guys are amazing and this was a great experience.

Carol: You are amazing. Thank you so much, Josh. You story is beyond phenomenal and I’ve enjoyed every last second. Thank you so much.

Josh: Thank you guys.

J: Josh, this was fantastic. We are so glad that your daughter is on the road to recovery and that you have found new purpose since then. And we wish you good luck with everything you do in the future. I hope you’ll come back on Show 500 and give us a recap.

Josh: Oh, man. When I’m even grayer than I am today, sure.

J: Thanks so much, Josh.

Carol: Thanks so much, Josh. See you soon.

J: Bye.

Josh: Bye.

J: Wow, what a great episode. I think a lot of us are familiar with BiggerPockets as a real estate investing website but I think very few of us think about what went into building a company like BiggerPockets. And it’s amazing thinking back, Josh started this company 15 years ago. It took him years, nearly a decade to start getting traction. And just to see what he’s built in the last few years or how he’s scaled in the last few years is just amazing. How did you think about this episode, Carol?

Carol: I thought it was just awesome and I especially thought it was so powerful how he really broke it down to a very personal level and shared so much with us. And talked about the things that he had to do in taking a step back, realizing he wasn’t happy. Admitting those things that are really hard to admit. And just finding a way to move forward and grow the business to what it is today. Just really powerful all around.

J: Absolutely. I don’t think I was expecting the personal story in there and I think it was pretty touching and great to hear everything is going well for Josh and his family.

Okay, guys. Well, that wraps up this episode but before you go, we want you to be a guest on this show. And if you want to be a guest on the BiggerPockets Business podcast, here’s what you’re going to need to do. I want you to go to BiggerPockets.com/BizGuest. That’s BiggerPockets.com/BizGuest. And fill out the form there.

Carol: Okay, everybody. Remember to subscribe so you don’t miss an episode, got it? Subscribe right now.

J: Thank you everybody for listening. We are Carol and Jay.

Carol: Now, go share some of your expertise today.

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In This Episode We Cover:

  • Joshua’s eclectic career path before founding BiggerPockets
  • His first disastrous foray into long-distance real estate investing
  • The void he sought to fill when he launched BiggerPockets
  • How he attracted members to the site by providing value in other online communities
  • The moment he broke down and almost quit
  • How hiring a consultant led him to hire his first full-time employee Brandon Turner
  • Why employee “fit” is more important than impressive credentials
  • Why sticking to his principles (no gurus, no upselling) was good for long-term business
  • Why he decided not to return to day-to-day operations after taking a leave of absence
  • How he negotiated a partial exit from the business by bringing on a private equity firm
  • And SO much more!

Links from the Show

Books Mentioned in this Show

Tweetable Topics:

  • “Failing is good. If you fail, that means you’re trying.” (Tweet This!)
  • “I only have one rule. I will not lose.” (Tweet This!)
  • “I can’t let YOU dictate my success or my failure.” (Tweet This!)
  • “People who are passionate about your business are going to be the best hires.” (Tweet This!)
  • “Be good and good will come back to you.” (Tweet This!)
  • “Thinking is work.” (Tweet This!)

Connect with Josh

Note By BiggerPockets: These are opinions written by the author and do not necessarily represent the opinions of BiggerPockets.