Afford Anything - How I Grew BiggerPockets From 0 to 870,000 Members - with Joshua Dorkin

Episode Date: October 16, 2017

#99: Thirteen years ago, Joshua Dorkin's friends teased him about starting a website that seemed to have no future. "I would get calls from my buddies who would literally call me on my cell phone [and say] 'Hey Josh, we just walked past a penny on the ground. We were thinking about picking it up and mailing it to you." At the time, Dorkin had just launched BiggerPockets, a then-nascent website about real estate investing. "I was working a full-time job making no money as a teacher," Dorkin says, "... and then [I] quit that job, reliable income, to blindly create this platform for other people. And I was helping other people get rich, and I was broke." Dorkin spent the next 8 years working mostly as a one-man operation as he tried to monetize a fledgling website. "We were struggling and scrapping by on every AdSense check that we could collect," Dorkin says. "The business really wasn't making serious money for probably getting close to a decade." The story has a happy ending. Today, BiggerPockets has grown to more than 870,000 members. The podcast has almost 250 episodes and the blog features more than 8,100 articles. In today's episode, I have a heart-to-heart with BiggerPockets founder Joshua Dorkin about the blood, sweat and tears that's required to start a successful online business. What lessons did he learn along the way? What regrets does he hold? And what advice would he share with other aspiring online entrepreneurs? We don't talk about real estate investing in today's episode. Instead, Joshua and I focus on the harsh realities of growing an digital empire. Enjoy!   You can find more information in the show notes at http://podcast.affordanything.com/episode99 Learn more about your ad choices. Visit podcastchoices.com/adchoices

You can afford anything but not everything. Every decision that you make is a trade-off against something else. So what are you going to choose? My name's Paula Pan. I'm the host of the Afford Anything podcast where we explore these questions. And today, I am interviewing Joshua Dorkin, the founder of Bigger Pockets. Bigger Pockets is a huge real estate website and podcast. But Josh and I are not discussing real estate today because here's a thing.

Joshua is somebody who from scratch started a website and took it from zero to millions upon millions of users. So it actually surprises me when people want to interview Joshua about real estate because a lot of people invest in real estate, not that many people have the capacity or have the experience of growing a website from zero to so big. And so that is what he and I talk about today. We talk about how he grew an online business that is hyper successful. The first 20 minutes or so of this conversation, we kind of go into the weeds with business a bit. And then at around the 20 minute mark, I think you're going to find we go deep into the emotional struggle of working year after year at a business that you don't know if it's going to succeed or not and doing it alone. So this is one of my favorite interviews.

I really enjoyed it. With that said, I hope you do too. Here he is. Hey, Josh. What's happening? Not a lot. How you doing? It's been a while.

Yeah, man. It's been, what, a year since we chatted? Maybe. Were you? Maybe more? I wasn't at Think on last year, so it might have been a little longer. Okay, so it's been like two years since we've talked. Dude, that's a long time for people who both run real estate websites.

There aren't that many of us. Yeah, it's been a minute. I'm glad things are rock and rolling for you, though. Yeah, you too. So I wanted to chat with you today, but I have. have no interest in talking about real estate with you. Perfect. Let's talk about, I don't know, movies. What do you want to talk about? What I do want to talk to you about is I think this is probably the conversation that a lot of people miss having with you is you grew a website from scratch to,

I don't even know how big it is, a bagillion people. How'd you do that? Bajillion is officially in the dictionary now. So this is a fair question. Man, it was a lot of, you know, it's the same, same BS answer, right? It's blood, sweat, and tears, and that's the truth of it. I mean, I literally, so we are approaching year 13 now of bigger pockets. Whoa. Yeah, it's crazy, right? You know, I came up with an idea for a problem that I personally needed solved, right?

And that was, stop losing all my money in real estate. Stop screwing up, stop messing up. and I found a solution which was create a community of people who can help me solve my problem. So I just started building this thing out and really it's been a labor of love and hate, a lot of hate. A lot of love. I think the love has always come from hearing from other people that we're solving their problems. We're out there. We're helping them.

The hate is just, you know, it's a lot of work. And especially in the first, you know, eight years, it was really me. And I had no, I had no support network. I had no teammates. I had an individual contractor who had worked with me on code and things, and they were always fantastic. But, you know, I mean, I had all the other stuff I had to worry about. So how do I do it?

I mean, there was no book, right? I mean, 13 years ago, Pat Flynn didn't exist. I mean, there was no, you know, how to start an internet company blog. I mean, blogging was nascent. We didn't know what the hell we were doing with that either, right? So I just looked at other websites. I found a few web communities like WebPro World and I forget Webmaster World. They were all kind of wrapped around the same subject, but use those to bounce ideas off of people.

But really, it was all about experimentation. Just like, hey, what would be a great idea? Let me try this. And I would try it and it would fail. And then I would try it again. It would fail again. And try it again. And maybe on the fifth time it would succeed.

What are some examples of things you tried and failed, especially in the early days? You know, that's a long time ago. And I'm old, Paula, so I don't know that I actually can remember these things. Gosh, honestly, I'm trying to think back on what the original way that I used to get people to come to the site. And this was before the blog was even launched was I would go to other communities, non-real estate, because I thought it was shady to go to other, quote, competing sites and try and poach members. I just thought that was raw. So I would go to stock market communities or I would go to, you know, Webmaster community. Any community I could find and I would go and find their off-topic areas. And I would dive in off-topic areas. And I'd wait until I would find questions about real estate or personal findings. finance, I would jump in, I'd answer questions, and back in the day, most forums allowed you to have

a signature, so I would put a signature that talked about pockets real estate community. And the more I would do that, the more I would demonstrate that I knew what I was doing. I knew what I was talking about, and little by little people would drip through and come to the site from those signature links. And that was how I got the first set of people on the site. Failures. I mean, man, I think we've gone and cleaned up the blog and deleted all those old. posts, but like, my God, I didn't know what the hell I was doing when we started blogging.

I mean, I think the first article I ever wrote on the blog, and this was before again, anybody knew how they held to blog. It was something to the effect of CNN has some great commentary on what's happening in the market. And then I would quote two paragraphs from CNN that talked about what's happening in the market. That's what I did for the next year, because, you know, nobody, we weren't writing our own content. Bloggers weren't necessarily doing that.

We were making little bits of commentary on other people's journalism. And then over time, you know, you started to see people to take that risk and start to write their own stuff. And over time, that eventually kind of came together. So, you know, I would call that a failure, but it wasn't a failure, right? I mean, like everything you do is a learning process. I just think it sucked looking back. but hiring bad people, working with bad contractors, making stupid decisions.

I mean, God, we could do hours and hours and hours on all the failings of me in bigger pockets over the last 13 years. And then we'd need about, you know, five years to talk about all the amazing things that this website has done for other people. But blood, sweat and tears, really 80-100-hour weeks for eight years, didn't take a vacation for over, almost. eight years, like not a single day off even, just absolute commitment and absolute unflinching desire to win and not let anything get in my way. And you put all that together with, you know, hustle and, you know, striving to constantly learn and get better at anything and everything that I did or that we did as a business resulted in what we have today. Do you remember what the visitor growth looked like, particularly in the first few years? Do you remember how many monthly visitors

you would get you had at the end of year one or year two? Don't. We had a lot of hits. Hits. Hits. The hit counter, right? We all had a hit counter. I don't, honestly. I remember, at least in our community, I was excited, obviously, when I got our first member and our fifth member and our 10th member and our 100th member. And I remember we, you know, I'd be. You know, I'd be began to monetize it through Google AdSense. And so I remember my first, I don't know if it was the first check or at least the first like, hey, this is how much money you made on the first month. And it was like 27 cents or something ludicrous like that.

They're like, I'm making money. This thing's for great. It felt so good, you know, to be able to create an income stream, if that's what you would call it, from writing and getting people to kind of talk to each other. There was something great about that. Of course, my friends and family thought otherwise. You know, I would get calls from my buddies who would literally call me on my cell phone and be like, hey, Josh, we just walked past a penny on the ground.

We were thinking about picking it up and mailing it to you. Decided otherwise. You know, just cool, nasty stuff. You know, there was no faith. And that didn't stop with them. I mean, you know, I mean, I talked to money people, VCs and things like that, you know, a few years in and they're like, this thing just has no legs. It's not going to go anywhere. And I was like, I will prove you wrong.

I will prove you, you know, and I didn't really say that. But, you know, in my head you did. Yeah. Yeah. So, no, I don't, you know, it took years and years and years and years and years before it really started to pick up. I'm very lucky that my wife, girlfriend, when I started it, but wife was willing to kind of support me through all the crap in the early years because I didn't make any money. I was working a full-time job making no money as a teacher when I started it and then quit that job, a reliable income, to blindly create this platform for other people. And I was helping other people get rich and I was broke. That was really challenging. You know, everybody thought that we were somehow making all this money and we weren't. You know, we were literally just struggling and scrapping by on every ad-sinch check that we could collect.

I mean, the business really wasn't making serious money for probably getting close to a decade. Hmm. What kept you motivated through all that time? You? Oh, thanks. Yeah, you got it. No, it was. I mean, it was you.

It really was. I mean, you as representative of other people like you, you know, There were a lot of difficult moments, a lot of frustration and challenges. And the thing that kept me going throughout everything was stories that I heard from people who use this platform to help themselves with their business. And I think if not for that, bigger pockets would not exist today. So thank you, I guess, to all the people who emailed me and shared their stories on the site. Because, again, like, no joke.

Had it not been for that, there's not a... chance that I want to stuck this out. I have a few questions. I have a few other questions, but before we move on to that, I want to go back to those early days and ask you a little bit more about how you grew. You mentioned going to forums and participating in forums and having a signature link. How else did you find those first few readers? So that was one.

I think the blog was born about a year or so after. the site itself was born. Again, it was a similar tactic. The idea was, I need to become known as somebody who knows what the hell they're talking about. So I began to go to the personal finance blogs, the real estate blogs. I mean, there weren't thousands or millions of those. You know, there were dozens of people in the personal finance and real estate niche who were writing about this stuff. And we all knew each other. We all knew each other because we were all participating on each other's communities. I would jump in somebody's forum, and I, you know, everybody was kind of doing the same thing.

We were all like, hey, well, a great way to get to know other bloggers is to blog, is to engage with them. And, you know, you do it over and again, and they get to know you and you get to know them. And then they'll come on your site and they'll start to do the same thing. And back then, you know, I don't know that any of us really realized that we were kind of becoming this niche of influencers, right? influencing one another, and we created all these bonds between us. Who are some of the other major bloggers at that time? Oh, man. Because we're talking, what, 2004, 2005-ish?

I mean, you know, in the real estate space, guys like Todd Carpenter, who's now one of the top guys at NAR, Dustin Luther, Jay Thompson, who now run social media at Zillow, you know, some of the PF guys, I mean, all the who's who, right? Yeah. But, you know, they're the who's who because they've been around, they've been doing this forever, right? And there's newer bloggers who were fantastic, absolutely amazing. But again, back then, nobody else was doing it. And so like this kind of generation of bloggers became kind of the like, you know, the, what do you call them? Not the grandparents,

but the kind of like founding communities of bloggers. And it was cool. It was cool. How were you able to pull out of the blogger to blogger fish bowl? Like how are you able to expand past that. That's a great question. And I was very, I definitively did that. What happened in that stage, there were a number of years, I think, where this was really going on was bloggers, you know, again, this was a new medium. Nobody knew what they were doing. We were all trying to get traffic. We were all trying to do the stuff. And, you know, some folks went the way of, hey, we can get traffic because we all have built these audiences and we could kind of push traffic amongst other people and do contests and come up with this creative stuff. And I kind of said, all right, well,

I could do that and it will work. However, I don't think it serves my users. And so I step back. And it actually, I think it was very risky. And I think as a result, I actually lost some influence in the real estate and PF blogging world because I was being less, you know, call it giving. to speak, and more kind of introspective and more focused on, like, I'm just going to talk about real estate at this point. And so I wasn't less giving in that. I wasn't like, hey, I'm not going to link to good content. That's just selfish BS. But it was, I'm going to serve what I believe is the need of my, of my reader at this point. And my reader is not just, I wasn't only writing for other bloggers, which I think a lot of bloggers were doing.

at the time, I said, I can't do this. Looking back, I think we took a little bit of a hit as a result of that, but I don't regret it at all. And frankly, I still know and like all those guys and, you know, still friends with all those guys. I'm not as tight with them as other people. You know, there were these clicks that were created and clicks were formed. And, you know, clicks exist in much of the online world.

I'm kind of this outsider looking in within a number of clicks, I believe, because I always just kind of focused on my users instead of focusing on the other bloggers. And I don't know. I mean, it's interesting to look back and think about it. But I don't know. What would you say about that? So I will repeat what I think I heard you say in the answer, which is, it sounds to me like what you said is you formed an avatar of the person who would read your site. And that person is not a blogger.

That person is just an ordinary person who wants to invest in real estate. And then you always wrote to that avatar. I think that's fair. I mean, you know, I guess today we would call it persona, right? Persona, yeah. Decided on what the persona was and that's what the focus was versus the persona of, hey, I'm going to write to other bloggers. And how would you balance creating content for your users, creating content for your readers,

How would you balance that with what you yourself wanted to create? In order to kind of clarify that question, I recently had a conversation with a musician who kind of drew this Venn diagram, and he was like, look, there are the songs that I want to play on stage. And then there are the songs that my audience wants me to play. And, yeah, that Venn diagram overlaps in a little bit, but there are a lot of songs that I just have to play because my audience wants to hear it, even though I don't want to play it. and vice versa. There are songs that I want to play that they don't want to hear. Yeah. So you're talking about content specifically? Yeah. I guess I could open it up to anything, yeah, if that strikes you in any other way. This is not an absolute, but I think I primarily focused on the circle, on the Venn diagram,

that was, what do I think my users want? There's a different path for everybody. You know, you're 20-something female with X in the bank and high-risk tolerance. You're going to have a very, different path than the 40-year-old who's got three kids whose wife is really, really anxious about getting involved going to be very different than the 40-year-old who's single, than the 40-year-old who's got, you know, a lady on the side. I mean, there is not a single path for any one person. So that was what I espoused. That's what I pushed.

And that wasn't very popular for a very long time. but I think over time that caught on. I think over time repeating and repeating that, you know, different philosophies that bigger pockets and me, I've either come up with or other people within the community that I feel should be amplified. It wasn't necessarily what the industry or people out there wanted to hear, but I thought it was important that it be told and be heard and be said. And over time, history has proven that having that faith in those ideas was a good idea. And espousing things like, you know, be smart. Don't just throw your money and, you know, I call it investing in markets for appreciation gambling. Yeah. My phrase about that is

appreciation of speculation. Right. Correct. Well, but when I started to say that back in the day, I mean, people go crazy. People get so angry. They still do. Yeah. But. You know, I think more and more, you know, we've all come to realize that, like, hey, if you can go buy a property, we're not talking about real estate, by the way. We are not talking about real estate. But if you could buy a property, you know, with a solid cash flow, appreciation is a bonus. Exactly. Yeah. Right. I mean, any deal that will work without appreciation is bound to be a far superior deal than a deal that requires appreciation. Yep. Exactly. That's all I'm saying. is change your standard. That's all. Odds are you're going to get in a better deal. And so it's things like that. So I stayed true to who I was.

I stayed true to what I believed in. That was challenging. But over time, I think history has proven that that was a good call. What were some of the hardest decisions that you made in the 13 years that you grew the site? That's a good one. I think in the early days, creating forum rules was hard. most forums were free-for-alls. And so being a stickler for like, you can't talk about this in this way or you can't talk

about this at all on our platform created, I got a lot of angry mail from people, some threats and things like that. By year eight, again, I was working 80, 100 hours a week. I hadn't taken days off. That was a monster, monster mistake, not taking days off. Like, you know, I don't tell people that to brag. I tell it because I was an idiot. But the challenge was I didn't have a staff.

I had to do every job. And I felt like I had to be on 24-7-3-65, and I kind of did. I kind of created my own worst nightmare. I created a set of expectations that only a superhuman person could live up to. And I began to not be able to live up to that, obviously, because nobody could live up to superhuman expectations sustained over time. what began to happen was I just got worn out. I got worn out. A number of times I wanted to stop, quit, shut it down, just get out. You know, the worst of which was almost five years ago,

you know, just broke down, started crying to my wife. And I was like, I hate this. I hate bigger pockets. I hate everything I do. Why am I doing this? You know, I want to quit. She said, well, then you should quit. But there's other possibilities. What if you get some help? What if we, you know, what else can we do? And I looked at that and hired a consultant. Consultant helped me to see that I was so stuck in the business. I was so stuck focused on the day-to-day, the grind, the minutia that I wasn't thinking about where we were going and how to get there big picture-wise. I think that's one of the biggest mistakes. It's not a mistake. I think that it's one of the biggest, I'd say challenges that most small and growing businesses face is getting stuck in the day-to-day.

Eventually, that led to one of the best decisions ever, which was hiring Brandon Turner to come and be my first employee, and that began kind of the birth of this company, you know, because before that, you know, it began as a hobby, became a lifestyle business and, you know, a lifestyle business where I had no life. The transition, it's true. I mean, you know, why the hell we should, why have a business that you cannot enjoy the fruits of the rewards from? I was not. I had eight years where I was kind of, I might as well not have been alive. I mean, not saying it in a depressed way. I had kids. I had my wife and things like that. But like I wasn't there for anybody. I wasn't present. I was just so deep in this stupid business. And I say stupid because that's how I felt, right?

I mean, I was like, gosh, what am I doing? But I got to keep going. I got to keep going. Because at some point, can get me there. And eventually it did. However, it did so at the cost of a lot of years. And I can't get those years back. And so when I realized that, I was able to see the light after, you know, Brandon came on and I started to work, you know, 95 hours instead of 100 a week. You know, I realized, well, life is short, you know, and I wish I had read the Paula Pant blog well the hell before that, but, you know, life is short. And at least for me, work is not my everything. And work is a means to an end. There's, you know, what's your why, right? My why at the time was to make money. Well, I could have spent those eight years working on a nine to five job and would have had a

much better life than I did. But ultimately, you know, it's led to where we are. And I don't, I somewhat regret it, but mostly don't. You know, it was a means to an end. But now I live a different life, right? Today, I've built a company. Our culture is the way it is because I want to put family first. You know, I live my days in a way where I put my family first. And an example for that would be, you know, I get up in the morning, I take care, do some exercise, you know, take care of myself. And then my kids wake up and my wife wakes up and I, you know, make them breakfast and hang out with them and spend time with them and take them to school. And only when I get to work, am I actually working? I'm not in the phone working like I used to be. I would get up in my

box of shorts and go to work immediately, right? Now it's spent the time with the family. When I'm at work, I'm at work. But if there's something for my children, I'm there. You know, I'm going to go and I'm to take care of it. And then when work is over five o'clock, some days four o'clock, some day six o'clock, I'm not at work anymore. I'm now with my kids. I'm now with my family again until they are asleep, at which point I can then resume if I so desire going back to work again. But making sure that I put the important people and the important things in front of the job and the company, at least for me, was the right thing to do. I would rather have a great life. and be there for my kids and be a great dad and great husband, then be a be a beggilineer

because I worked, you know, hundreds of hours a week and, you know, grew this company X times faster. That, to me, is nonsense. I mean, what's the point if you miss out? And I think I missed enough time that I'm not willing to do that again. How old are you? 41. How old are your kids?

Got a four-year-old, a seven-year-old, turned seven today, and a eight-year-old. So. Nice. Yeah. How has that decision that you talked about, the decision to lead a more balanced life, how has that impacted your business? It hasn't. I don't think it's impact. Well, that's not true.

I think it has, because it's not only about me leading a balanced life, our core values, our first value is family above everything else. That is true for me today and it is true for my team. And so, you know, if my employees need to. Go to the doctor in the middle of the day. Go to the doctor. If you can't get the car appointment at 530, which who the hell can get a car appointment after work, go get your car taking care of during the day. You'll make it up in the evening.

You'll make it up on the weekend. You know, giving people, I think it's treating people like grownups, giving them balance, giving them the opportunity to live a good life for themselves. And at the same time, obviously, focus on work and helping them grow as individuals. it motivates people. It makes them happier and happy people work harder, happy people work smarter. And so, you know, we've got a fantastic team today of people who are doing an unbelievable job. And I think keeping them happy and focusing on how we can continue to do that is really important for the company and the company's growth. But look, I mean, do you sacrifice stuff? Yeah, maybe we sacrifice the rate at which

we're growing, I'm willing to sacrifice that. I've always been willing to be patient on that because, again, there is no rushing. I mean, look, I've never raised money, right? I've thought about it. I've talked about it. I have wanted to on and off many, many, many times. But I knew that doing that would come at a cost. And the cost for me would have been the cost of having a boss. Because once you take somebody else's money, now you work for them, no matter how much you want to think, you know, I work for my employees and I work for my users. That's who I work for. The second you're borrowing money, you work for your shareholders, you work for the bank,

you work for your investors. I never really wanted to have that monkey in my shoulder. Is that the right saying? Grilla on the back, monkey? I don't know. Yeah, that makes sense. I think monkey on the shoulder. We'll make that a saying.

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That's freshbooks.com slash p-a-u-l. You mentioned happy employees work harder, happy employees work smarter. Have you found that true in your own life in the difference between then and now? You know, that's interesting. I don't know that I can compare because, is, you know, today I have an infrastructure. Today I have a system. I mean, I have an assistant. You know, I've got a few dozen employees working for me doing all the stuff that I used to do. So I'm happier because I'm working less. I'm happy when my employees are happy. I'm happy when

they're succeeding and accomplishing cool things. But it's hard to compare them then and now because, you know, then it was me slaving away and doing all the little details. And frankly, not doing a great job of any one detail because I was spread so thin, but I was willing to work super hard in order to do it. Today, it's bigger decisions that I have to make. It's helping people make the smaller decisions, helping them solve the problems that they need to solve, helping guide them. So it's a completely different role that I have as CEO of a company with you know, approaching 30 employees and a company of one. As you empower your team to make decisions, have you found that they make decisions that are different than what you would have made?

And how do you kind of maintain that balance between empowering your team and leading your vision? That's very hard. That's actually really, really hard. Had a hard lesson on that in the past couple months. I think I allowed people so much freedom that they kind of went forth. And, you know, months later, I looked back and I was like, oh, I don't like the direction we're going. And not because they were making bad decisions, but because it was outside of what I saw in my own head as what I wanted. And what I learned was I needed to create a framework under which these people would work. Without that framework, you know, you're going to give intelligent people an opportunity to run with something. They're going to run with it. And that's what you want. The balance that I think most people, well, the balance that I learned is I need to give them a framework under which to work and give them the freedom to operate within that framework. But if I don't give them the framework, they're going to no matter what inevitably go outside of that framework.

And it's not their fault. It's just because they don't know what you want. Nobody can go in your head and know what you want, know what you see for your business. So you need to put pen to paper or finger to keyboard and write out, you know, hey, here's how I see marketing. Here's what our campaigns should look like. Here's how we talk about the user. Here's how we talk to the user.

Here's our philosophy on engineering. Here's our philosophy on support and service. And here are the guidelines under which you need to work. Because I had not done this before, I didn't know any better. I assumed, hey, smart people are going to figure it out and it'll be fine. And it was fine. But what I found was it just didn't feel right. It didn't represent me or my vision in the way that I wanted it to.

And so, you know, it took me hiring a coach to figure that out and to see it. But since realizing that, you know, reined in and created those guidelines in the framework, and it's created so much more clarity for my teams and my team leads, they know the bounds under which they need to operate. And that's extremely helpful. How do you make hiring decisions? And specifically I'm thinking about you've mentioned a consultant, you've mentioned a coach, These are very high value people.

How do you find and select them? And then evaluate them once you start working with them. Coaches and consultants are employees. Let's start with coaches and consultants. So the first guy I hired, I had known him for years. He was one of the original bloggers that I knew, knew everything about real estate. We had become friends. Wicked smart guy.

He was consulting companies. I said, I'm going to just give it a shot. I did. He turned out to be wicked smart and was really good. helpful. I hired another coach that was based on recommendations of some friends. I think that worked out well. We kind of outgrew each other. And then this most recent one, again, from my network, it was, hey, who do you know, just asking everybody, who do you know that does this? Who can I turn to? Got some recommendations. We met a bunch of people. Found one that seemed to get it and just went for

So that was how I've done that. Employees, very different process today than it used to be. Today, the philosophy of who we're looking for has now been passed along to my team, right? So unless I'm hiring a manager or a senior executive, I usually come into the process much later. And so, you know, we've created a process under which my head of HR and our department leads basically conduct a search. and they go and they do their thing. And, you know, I come in. I still interview every single employee, potential employee that makes it that far because I think it's important to ensure that I still have my stamp of approval on them. You know, they fit the energy that we're looking for.

They have not just the skills, but also the mindset of bigger pockets. And that's something that I think more and more other folks within the team are, able to pick out, but, you know, it comes with time. What about those first few employees? How did you find them? Well, Brandon was my first, and he came, he was a writer for Bigger Pockets. So he and I had known each other for a long time. Oh, that's right. His blog was Real Estate in Your 20s.com. Yeah.

He was writing for us, and we just became friends, and we started chatting. and he was pretty much retired at the time. It's like, hey, I'm living off my real estate and, you know, no man's land in Washington. And like, you want a job? I'm looking for somebody to help me with all these things and you're pretty good at it, it seems. You want to try it?

And we just kind of dated for a while, like talked on the phone every night for, you know, for hours and hours and hours. And I'm like, yeah, yeah, let's try this. My next, I don't know if Scott was number two. I think Scott was number two, or three, but Scott came, he was a fan of the podcast, and I was working in a co-work space, and he was touring the co-work space.

They'd walked, they were like, hey, this, you know, this is this, this is this, and this is bigger pockets, Josh, and he walked in, he's like, oh, my God, that was the biggest one of that's going on. He was so excited and was like, okay, weirdo, go away. Oh, he's scaring me, but super, you know, energetic, super cool, and, and I don't remember, I think he applied for the job. And afterwards, I don't remember all the details. He could probably repeat it.

But, you know, he just proved he loved the product. He loved bigger pockets. He loved who we were. He was super enthusiastic and he had a skill set I was looking for. You know, at that point, I had two contract developers that I had been working with. One of them recommended a guy who had lived in town because I was looking for an employee developer. So that's how I got my first full-time developer. employee. So a combination of just referrals and instinct and gut and, you know, a crappy screening

process. No, but I mean, the first few people were incredible. I mean, Allison and Hillary, who came on and they were incredible. You know, made a couple bad hires over the years and have since learned how to screen better for that. And how do you screen better for that? It's literally, little things, right? We had hired somebody who was very smart, great resume, very ambitious, but they job hopped. So every year and a half they had a new job. But I was so desperate for somebody that I was like, well, this person is absolutely qualified. They were qualified. But I allowed myself to overlook the fact that they were on their third or fourth job in five years, right said well maybe this time will be different and allowed myself to be convinced that this

time would be different of course you know as predicted in less than a year they were gone and in less than a year they were gone from their next job and in the next year or two they were gone from their next job and and i was right right uh my gut was right and so you know using that as as a means for screening so it's it's things like that right it's trusting the system for trusting your gut that like, hey, somebody who's going to job hop every year and a half to two years is likely to continue doing that, right? So it's those little things. I know that seems obvious, but it's not necessarily obvious, especially when you're desperate and trying to hire somebody. I mean, we just hired a front-in engineer. We started looking for that position in December.

It took us almost 10 months to hire this position because we refused to compromise as desperate as we were to fill that role, we absolutely refuse to compromise and fill that with the right person. Those are not easy decisions to make. But yeah, I mean, and we've got other cool stuff in our process. We've got, you know, a family interview, which is, you know, we bring in different stakeholders who may not necessarily be working directly with that person. And, you know, for us, if it's not 100% yes across the board for everybody who's in the room, then it's not a yes. If one person who may not even work with them see something that kind of troubles them,

we're going to trust their instinct. We're going to trust their gut that this person just may not be the right fit. Your background was you were a special education teacher, right? That was not my background. I did fall into that job, which is quite the job to fall into. But, you know, my parents were entrepreneurs, kind of grew up in an entrepreneurial household. I was always interested in business. I grew up in New York, so everybody's interested in money in New York, which eventually

I grew out of, even though I kind of do what I do. And then I was a prop trader for a while. In college, I finished with a marketing and political science. I was in the entertainment business. I've always just been kind of the school of work your ass off and figure it out. So bounced around. I mean, I just, I did a number of things. Okay.

So in everything that you've said, I don't hear anything that is highly technical. And yet now you're in this position where you are hiring engineers and developers, which means that you need to, at a minimum, be able to describe the job needed and describe, at least at a high level, the scope of work. How do you do that? how do you lead people in technical roles? And how do you deal with the fact that there will be cases in which you don't know what you don't know? Not a day goes by where I know what I'm doing at work. I think anybody that would say otherwise is probably lying or probably too comfortable.

I like people who on a given daily basis don't know what they're doing or don't know how to approach something. it means they're challenging themselves. In the beginning, man, I made so many mistakes working with engineers. I taught myself HTML. I taught myself web design when I hired my first engineer contractor. I mean, I knew design. I knew how to create a product. At least I had figured out how to do that.

But I didn't know necessarily the programming language that they were going to code the platform in. once I had hired them from there to forward. And it was risky. It was really risky. In fact, I made some really bad engineering choices in the early days of bigger pockets. I mean, my first engineering choice was to hire a consultant, a offshoreing contracting company. I was living in L.A. There was a guy in L.A. who was my contact, and they had a team in India, paid them a lot of money, and they were going to build this social network that I wanted to create, which was going to be the next MySpace for real estate investing, because of course MySpace was a hot thing back in the day. The problem was I couldn't evaluate their code.

You know, I worked not very close, but I worked kind of close with a couple engineers in India while they were doing their thing over Skype and this guy in California who was the go-to, the pass-through, whatever you would call them. But, you know, six, eight months later, I had spent, you know, 15, 20 grand on building out this platform and I got back a bunch of code that didn't work. And there was no process. I didn't know how to vet, evaluate, make sure that things were done in a manner that would not lead to failure. And so I got back, you know, a hunk of code that didn't work. It was horrifying. That was one of the many, many times where I was like, I, what am I doing? I quit. I'm done. I have no business doing

this. You know, stopped and said, how did I screw this up and broke it down? And, well, we took this project and instead of, we built, you know, this massive thing in one giant step. And there weren't, you know, milestones. And so let me try and break that down. You know what? Let me, let me go back at this. And instead of building everything at once, let me hire a guy. Instead of building a social network, we had a forum at the time. Let me hire a guy to just build out profiles. It was small. It was attainable. It was something that I knew enough to be dangerous.

I knew how to look at the database and make sure that it had the fields that it needed. I knew the design, what needed to generally be there. The functional code and how to make it happen, I didn't know how to do, but I knew enough that I could speak intelligibly about these little things, right? And so over time, I just got better and better. And one of the things I actually pride myself on, even today, and my guys don't really use me anymore for this. But, you know, when there's a problem, I love getting in there because oftentimes it's not a code issue. Oftentimes it's just a how you thought about something issue. So I could

diagnose and find problems in code without actually knowing the code itself because it's just problem solving, really. So anyway, over time, I just, I got better. I learned the language. I learned how to communicate and I learned to hire people way the hell smarter than me and know that they were way of the hell smarter than me and trust that those people that are smarter than me know what they're doing. Yeah, and now they're the ones who do the hiring. They're the ones who do the technical interviews. They're the ones who ensure that the people that we hire are up to speed. I like the phrase that you used, you knew just enough to be dangerous. Yes, I use that a lot. It resonates.

Joshua, this has been fantastic. Is there anything that I have not asked about that you would want to emphasize about running a business, about life, about work, about the journey that you've had in the last 13 years. I would love to talk about the podcast for a minute. Yeah. I love the, you know, hey, look, we're podcasting. It's fun. Yeah. And I don't know, whatever life, I mean, you know, I think, here, I'll throw my life thing out, which is, you know, we had talked about me looking at my life and making sure there was some balance. And I think it's one of the things I most enjoy about our podcast, which is talking to people about their life and seeing the process by which they came to a point of realization that they were not

just drones that were walking through life blind, which I'd say 99% of people do. And that's not an insult. It's unfortunately, like, we're taught from a very early age, you know, get up, go to school, college, get a job, work till you're 65, then you can enjoy the fruits of your labor a little bit, and Social Security is going to take care of you, and then you die, right? I mean, that's the life plan that we were all bestowed, and I think that's a bullshit life plan. You know, nobody can create your life plan. You know, you have to figure out what you want.

You've got to figure out what makes you happy and build a life plan around that. And you, you know, when we had you on the podcast, that was why people love that show so much. That's why people love you, right? I mean, that's, you're the epitome of somebody who has taken the reins of their own life and built a plan around it, lifestyle engineering, right? Thank you. No, you're welcome. I admire that.

I really do. And I guess I would say to anybody listening that it's so easy to say, I can't. It's so easy to say I can't do it. In fact, I just had the conversation with a friend of mine who was staying with me last weekend. It's got a job. And, you know, he's got a pension that's going to come up from that job. At some point in time, he's locked in, and they got him fooled. You know, it's like, hey, man, you got this pension.

So you quit your job. You're going to lose a big chunk of that pension, right? So stick around the next 20 years. Well, I hate my job. I don't want to stick around 20 more years. I want to do other things. But if I leave, then I lose my pension. And, you know, suddenly you're like your lockdown, right?

And, you know, not just him. I see it every single day when I talk to people. I think people need to realize that that's not what life has to be and there's other ways to do it and whether it's through online business or just finding a job that you love or real estate or I don't know. I mean following guys like Mr. Money Mustache, following, you know, Jim Wang and J.D. Roth and Paula Pan and, you know, these guys who are, you know, and the frugal people. There's countless different pathways that you can take to kind of building and engineering your life. but we have the ability to do that. And as scary as it is to stop what you're doing,

or at least change what you're doing, right? It's not just about quitting a job, but it's about having a job that you'd like in the first place. I think more people need to really just stop and look in the mirror and say, hey, am I happy? Is this the life that I really wanted for myself? And if I look back in 20, 40, 60 years,

am I going to say, you know, I wish I had taken those risks that I had thought about. I wish I had changed jobs when I thought it was time to change jobs. I wish I had done all these things. I think a lot of people go through life with too many regrets on stuff like that, and I don't want to be one of them. And I think we just too often do what we do for other people or other people's impression of us, and instead of figuring out who the true us is. So I don't know. I know. I was going to talk about podcasts. but I just got deep on you. That's perfect. That's beautiful.

Were you ever like that? Was there a turning point in your life when you broke that norm? Or have you always thought a little differently? I would say I've always walked my own tightrope. You know, back in high school, a good friend of mine had talked to me about life. And his big thing was live your life as if you were looking back upon it. as somebody in their deathbed and making sure to live the life that would be true to that person. I took heart of that.

I haven't always done it. You know, whether it was the teaching thing, look, I mean, when I taught, I don't regret having done the teaching thing. In fact, it was probably one of the most important things I've ever done in my life. I mean, working in special ed, the ability to influence kids and particularly kids who have a lot of stuff going on is so important. I think it was an honor to be able to have done that, but I didn't love that job. I didn't want that job. I fell into that job, but I did it. And when I did it, I gave it my all, right? But I couldn't quit, you know, and I couldn't quit for reasons like, you know, the school was owned by my mother-in-law, well, current mother-in-law, former mother of my girlfriend, who, you know, and, hey, well, I would be

letting them down, so I can't quit. I can't leave. Hey, I can't do this because I'm going to let other people down. I still do that. I still catch myself doing that. And it's the worst thing on earth. Doing things for other people is phenomenal, but doing things for other people at the cost of your own happiness, I think is a terrible thing. There's a balance. There's volunteering, that's giving back to charity. There's helping other people. That's great. But like, Don't work at a job because, you know, you think the company is your manager. If you leave, your manager is going to be screwed and everything, you know, is going to fall apart. They'll figure it out, right?

They'll figure it out. And that's not me talking about me. That's just like, in general, we all make these decisions. And I think we is most people where life decisions are made or not made out of fear of offending, or upsetting or letting down other people. And what people end up doing is letting themselves down. And I know I'm absolutely guilty of it. I still do it.

You know, when I look back and I'm like, ah, I've got to get a grip on this, right? I've got to do what I want to do. What's going to make me happy? I'm getting there. More and more, I'm making those decisions. And it's hard. I mean, you know, those decisions.

can be stressful. If you don't have a spouse on board, they can be really challenging or, you know, they can be financially risky. But at the end of the day, I mean, like, again, we were just trained that the world is about money instead of the world being about happiness.

And I don't know, I believe that I'm here to live a happy life, a happy good life. Money is a means to an end. I want to live that life. Perfect. Well, we're going to end on that note. And, I mean, the answer is obvious, but where can the listeners find you if they want to know more?

So if you want to learn anything about real estate, go to Bigger Pockets, check out the Bigger Pockets podcast, jump on the blog. We've got books and stores and online. If you want to reach out to me, Twitter tends to be my favorite place to connect with people. I don't know where we're not talking about real estate. I don't tend to connect with people I don't know on Facebook or places. I just try to keep that to people I know or want to know. So, yeah, that's it. I'm Twitter, J.R. Dork in and jump on bigger pockets.

And thank you so much for the opportunity to chat. Thank you, Joshua, for that extremely honest and heartfelt description about the realities, the harsh realities of what it takes to grow an online business. What are some of the key takeaways that we get from this? Number one, and this was never explicitly stated, but this is something that I really heard from what he described, don't do anything half-baked. You'll notice that Joshua was not simultaneously trying to grow three or four different

businesses. He picked one idea, one thing, which was this website, and he poured everything that he had into this. 80-hour weeks, 100-hour weeks, for eight years, never taking a day off, he poured absolutely all of himself into this one idea. Now, that's not to say that you should work the same 80-hour weeks. In fact, Joshua himself tells you that was not a good idea. But it is to say that 100% of your focus should go to one idea.

Because if you are simultaneously trying to tend to multiple businesses, you're probably not going to do that great of a job at any single one of them. It's kind of like, you know, if you're juggling, right? You imagine juggling balls. And you can keep maybe three balls in the air. But when you try to add a fourth ball, all of them fall. So you imagine yourself juggling, and one of those balls is life, because life demands some of your time and energy and attention. You know, life, family, health, like these are all juggling balls that you have. I realize I just named three already, and I haven't even gotten to work.

But that's exactly the point. You only have so much space for work. And so in order to do an effective job, just pick one idea and focus everything on that. So that's one takeaway that I got. The second takeaway that I got was a quote from Joshua where he says, I like people who on a daily basis don't know what they're doing. And what he means by that is that if you are constantly in your comfort zone, you're not challenging yourself, you're not growing.

Yeah, you may feel comfortable, but comfort is not necessarily what's going to get you to a satisfying life at the end. There's growth and benefit that comes from being at the edge of your comfort zone, from being just a little bit uncomfortable. So embrace that discomfort. Do it in athletics. Do it in yoga. Do it at work. Chief takeaway number three, live your life as if you were looking back upon it.

That was another quote from him that he said towards the end of the interview. And I really like that. You know, at the end of your life, you want to be able to look back and say, I had a good life. And a good life is a series of good months, good weeks, good days, good hours, good moments within it. Chief takeaway number four, do not make decisions based on fear of letting other people down. In other words, have boundaries, have strong boundaries. It's nice to help others, but not if you lose yourself in the process. And chief takeaway number five, don't try to martyr yourself on the altar of working a lot because that could actually end up being counterproductive.

You could end up getting burned out. And as Joshua himself described, when he scaled back and he started working less, it didn't actually have any negative impact in his business whatsoever. He's happier at work. And, you know, maybe his business is growing a little bit more slowly than it otherwise might. But heck, who cares? Business is still strong. It's still successful. And he is not working those crazy 80-hour weeks anymore.

Now he's got a very nice work-life balance. So those are the takeaways that I got from this conversation. I would love to hear what you think. Please head to Afford Anything.com slash episode 99, where you can leave your comments in the show notes. And while you're there, subscribe to get our show notes delivered to you by email. You can follow me on Instagram at Paula Pant. And of course, we will link to all of bigger pockets, the blog, the podcast, to Joshua Dorkin on Twitter. We'll link to all of that in the show notes as well.

That's afford anything.com slash episode 99. Coming up next week, we have episode 100 with a very, very special guest, which I cannot wait to announce who that is and what it is. So stay tuned for episode 100. Thank you so much for listening. My name is Paula Pant. I am recording this from Ecuador. This morning, I had breakfast with Vicki Robin, the author of Your Money or Your Life. So that was like, woo, really fun for me. So yeah, I'm going to sign off right now and enjoy my last afternoon in Ecuador. Thanks so much for tuning in. I will catch you next week when it's time for episode 100. See you later. What bothers me is when I'm out socializing and everybody wants to talk to me about real estate. Well, there's a reason. Why is that?

Well, because you're kind of a big deal. Aw. Yeah, it's like, you know, I'll be at a party and people want to talk to me about real estate. And I'm like, I don't go to parties to talk about this. Like, we can do this when I'm at work. That's cool. But we can do this Monday through Friday, like 9-ish, and we'll say 10-ish to 5 or 6. That's fine.

But if I'm like two martinis deep into the night, there's no way I want to have that conversation. And I have seen you two martinis in to the night, and you certainly are not qualified to be talking about anything intelligible two martinis in. Exactly. Let me tell you about cap rates. I'm excited something.