The Transcript

How to Scratch Your Own Itch and Build a Successful Business

Jonny Nastor: Hack the Entrepreneur is part of Rainmaker.FM, the digital business podcast network. Find more great shows and education at Rainmaker.FM.

Voiceover: Welcome to Hack the Entrepreneur, the show which reveals the fears, habits, and inner battles behind big name entrepreneurs and those on their way to joining them. Now, here is your host, Jon Nastor.

Jonny Nastor: Welcome back to another episode of Hack the Entrepreneur. I’m so glad you decided to join me today. I’m your host, Jon Nastor, but you can call me Jonny.

My guest today is a real estate investor, one-time real estate agent, podcaster, web designer, and Internet entrepreneur. He built, as well as being the Founder and CEO of, the online real estate networking platform BiggerPockets. The platform now has over 330,000 members.

My guest is also the CEO of BiggerPockets publishing division and has co-written and published two Amazon bestsellers. He’s the co-host of the Bigger Pockets podcast, which is the most highly rated and reviewed real estate podcast on iTunes. The podcast offers both educational content and interviews.

Now, let’s hack Josh Dorkin.

I want to thank today’s sponsor, FreshBooks, for making my life easier. What is the one thing that I am no good at? I am horrible at staying on top of my bookkeeping and accounting for my business.

Now, rather than losing the receipts and handing my accountant this giant messy box of papers, FreshBooks has this amazing app for my iPhone and lets me instantly just take pictures of receipts and sort them by touching a couple of buttons.

FreshBooks is designed for small business owners like you and me. FreshBooks integrates directly with three things that I use every single day in my business: PayPal, Stripe, and MailChimp. To start your 30-day free trial today, go to FreshBooks.com/Hack, and don’t forget to enter ‘Hack the Entrepreneur’ in the ‘How did you hear about us?’ section.

Welcome back to another episode of Hack the Entrepreneur. Today, we have another very, very special guest. Josh, welcome to the show.

Joshua Dorkin: Thanks for having me, Jon.

Jonny Nastor: Absolutely. My pleasure. All right, Josh, we’re going to jump straight into this. Josh, as an entrepreneur, can you tell me what is the one thing that you do that you feel has been the biggest contributor to your successes so far?

Never Giving Up in Spite of Daily Setbacks

Joshua Dorkin: I don’t give up. I think, as an entrepreneur, you’re always going to be battling some kind of fire. There’s always a fire to put out. There’s always something going on, and it’s easy to give up at some point, especially for solopreneurs and small businesses. It could get really stressful. Being able to have the mental fortitude to fight through the hard times is really one of the keys to being successful.

If you talk to any entrepreneur, they’ll tell you that it’s not all flowers. There’s always going to be that downtime. The people who crumble — and a lot of people do crumble — are out of the game. If you can fight through it, survive, persevere, then obviously you’re going to be around.

Jonny Nastor: Excellent. There’s always a fine line between the fortitude to carry on and the self-awareness or realization when what you are pushing into is not working for a reason.

Joshua Dorkin: Sure.

Jonny Nastor: Do you have a way of deciphering between those two?

Joshua Dorkin: Oh, man. It’s going to be different for everybody. For us, in our business, we launch products on our platform whether we think that they’re going to be successful or users tell us that they’re going to be successful — and sometimes they’re not. An example, we have built this chat tool into our platform. Our users were ecstatic. They were like, “Oh my god. We’re dying for this thing. We want it so bad.”

We’re like, “It will add value. The users will love it. It will keep them around a little bit longer.” We were excited to build it. It didn’t cost us an insignificant amount of time and money. We put it together, and we realized that, lo and behold, nobody cared. All those voices shouting out, “Yes I want this!”? They didn’t use it.

That happens a lot, especially in tech and Internet companies. It’s really easy for people to tell you what they want. Sometimes you’re right. Sometimes you’re wrong. Sometimes your gut is wrong. Sometimes they’re going to give you the wrong information. At some point, you have to make a decision. It’s really hard to decide, but at the end of the day, you got to go one way or another.

A prime example would be this product I think we’ve heard of it. It’s called Google+, which just got separated from YouTube yesterday. They thought that was the right decision. They thought that was the Facebook killer. They were going for it. It didn’t work, and that’s fine. Google is going to be around tomorrow to fight another day with another product against another competitor and build another market.

For us, the same thing applies. The chat didn’t work out. Nobody really used it, so we decided to kill it off. It is what it is. For me, I’m saying it in this passé way because I’ve done it before. The first time I had to kill a product, I perseverated. This was days and maybe even weeks of just stress and like, “What do we do? We spent all this money to build this thing, and to kill it now would just be at absolute travesty.”

Over time, you learn there are things that you have to do. You have to chuck up the losses, get your head back on straight, move forward, and try and get the wins. You’re not going to win them all.

Jonny Nastor: Totally. Google, for everything to be said about Google+ — and I don’t know the ins and outs of it, obviously — but they pushed that for years. That wasn’t like, “Here, try it for a month or two.” They kept just pushing it. Everybody has a Gmail account. They instantly had users, but the adoption I guess.

It’s an interesting one because Google, typically, they’re notorious for coming out with new littler products and just dropping them. Just drop them, “Nope, nope, nope,” and that’s how they figure stuff out. Google+ was a big one.

Joshua Dorkin: They put a lot of energy into that one, and I think they very begrudgingly shut it down.

Jonny Nastor: I think so, too.

Joshua Dorkin: Or separated from YouTube.

Jonny Nastor: Exactly. That’s the first step.

Joshua Dorkin: It’s not going to be around for long.

Jonny Nastor: Exactly. So, Josh, there seems to be a time in every entrepreneur’s life when they realize one of two things. Either they want to make something big — they have this calling to make a difference in the world — or, as mostly seems to be the case of my guests, they finally simply cannot work for someone else anymore. Could you tell me which side of the fence you fall, on and when you discovered this about yourself?

Why Some Businesses Should Be Built for Selfish Reasons

Joshua Dorkin: From the beginning, I was always the entrepreneurial type. My family were all entrepreneurs. I worked for myself out of college. I was trying to find my place in the world just experimenting with different ideas and different things. I was in the entertainment business. I was a prop trader. I got a real estate license and was a Realtor — tried all sorts of stuff. Ultimately, ended up falling into a job. I fell into teaching. I got a sub teaching credential to do it just to make a couple of bucks on the side, got a gig, and that one-day gig turned into four years of teaching full time.

While doing that, I launched this business, BiggerPockets. At first, I didn’t build it with the intent of having the second thing you talked about, which is this passion to change the world, so to speak. It was really out of necessity. I was having a semi-failing rental business thousands of miles away, and I needed help. This business was designed out of complete selfishness to help me become more successful and stop losing money.

Nights and weekends, I was plotting away on it. Ultimately, I started to see other people getting value from it and realized, “Wait a second, there’s more here. This is not just something that is this selfish endeavor. I’m actually helping people, and if I continue to work at it, I’m going to help change people’s lives. I’m going to help them be more successful.”

We talked earlier about the stick-to-it-ness. I’ve been at this almost 11 years, and I’ve had many times where I’ve looked at it and said, “Wow, this is not going where I hoped it would go. This is really too hard, and I’m not making enough money. I’m working 80 to 100 hours a week. I got to stop.”

The thing that kept me going, personally, was the fact that I knew I was helping these people. I was getting emails and calls from people whose lives we were changing for the better. That’s really one of the big things that helped me through the really hardest times, the lows — and there were lots of them.

Jonny Nastor: Wow. So BiggerPockets, it helps people with real estate, forums, and such?

Joshua Dorkin: Yes.

Jonny Nastor: You had a selfish problem where you had an issue with real estate with a rental business?

Joshua Dorkin: Yes.

Jonny Nastor: How’d you start? How’d you make that connection to others doing that? What business were you creating yourself to selfishly help yourself, but then also helped others?

The Value of Building a Business That Helps People

Joshua Dorkin: I feel like I’m in this weird matrix of non-understanding your question — no, I totally understand your question. That was a hard question. I wanted to build a rental business on the side. I had a background in building websites.

When I looked at the landscape of the information space for real estate investor information 10.5 years ago, what I noted was there was not a lot of information that spoke to me. The information that existed was all the get-rich-quick real estate guru guys. They owned the landscape. They didn’t own every website, but every website, they were affiliate marketing and working together. So everybody was in bed together.

I feel like I want to shower when I deal with that side of things, the guru side. I said, “There’s nothing around here that I feel I believe in, I can trust, and I feel comfortable with.” I just built a forum. I knew enough about the Internet, and I had been around a while. I built a forum with the goal to help me help me up.

Over time, it started making a little of money. I had some ads on it and things like that. I realized that maybe there was something there. Now, granted, I’ve been told by lots of people in the early years, “You’re crazy. What are you doing? You should shut this down,” and I probably should have at the time. I probably should have, but we came to a few tipping points that really started to energize the business and grew it.

Today, we’ve got this business. We’ve got a social network that we built. We’ve got a forum. We’ve got dozens of writers who write for us every week, so we’ve got this pretty sizeable blog. We’ve got the top podcast in real estate. We’ve got a publishing company with three of the top 15 real estate books on Amazon.

We took this idea of helping Josh be successful with his real estate business and transformed it to, “Let’s build this vertically integrated company that has content, community, and tools to help people who are just like Josh was and help them become more successful.” That’s what we do. We do it in, what I believe, to be a pure way.

It’s not about the upsell. It’s not about getting people into these thousand-dollar boot camps and $50,000 trainings. It’s about, “Hey, anybody and everybody should be able to invest in real estate.” We wanted to democratize the information space, and I think we’ve done that. We’ve opened the books. There’s no secrets. There’s no such thing as a secret in real estate investing anymore. I think that’s the beauty of what we’ve done.

Jonny Nastor: Wow, that’s impressive.

Joshua Dorkin: Thank you.

Jonny Nastor: Short answer, you started literally from a forum to get answers for your questions.

Joshua Dorkin: Correct.

Jonny Nastor: That’s awesome. Then, at some point in there, you decided to change it into just helping you to integrate the company that is now a publishing company, a publishing house, a blog, a podcast. Wow, that’s impressive, a good transformation. Most people don’t go from solo entrepreneur to that. They get stuck in the day-to-day.

Why Not Being Good at Business Shouldn t Stop You from Doing It

Joshua Dorkin: I got stuck in the day-to-day. I was stuck in it for eight years.

Jonny Nastor: Oh, wow.

Joshua Dorkin: I was stuck in it for eight years. I was teaching special ed high school in Los Angeles. I was doing this nights and weekends for two years. Then I quit. Then I spent the next couple of years just building this. I wasn’t even building a business. I was just focused on like, “Hey, community. Let’s build this community and make it strong. I’m making money on the side, not quite enough to survive, but wife is working and making a lot of money, or enough money to keep us going.”

All of a sudden, years past, and my lifestyle business, which was this cool concept of like, “I’ve got my own business. I can work whenever I want, wherever I want” — and it was true — but I was now working 80 to 100 hours a week. It didn’t matter where the hell I lived. I was so glued to my job. That was my life. We had kids. I started to look inwardly and say, “Wow, this is crazy. I need to get out of this.”

I didn’t understand the working ‘in’ versus ‘on’ your business concept until I hired a consultant and said, “What’s going on here? What am I doing wrong? I’m busting my chops doing everything I’m supposed to be doing, yet I’m still working like a madman.” One of the things that he said, one of the many things, was, “This is not a lifestyle business anymore. You need to transform or die.” And that’s what I did.

I started to bring on the people I needed to bring on to lighten the load for me and to actually help scale the business and started to hire. That was almost a little over 2.5 years ago. Today, we went from me and a developer, which is all we had, we’re up to 19 people now.

Jonny Nastor: Wow, nice. So you hired a business coach?

Joshua Dorkin: I hired a consultant to look at the business. This was a short-term engagement to look at the business, help break down the business, look at me, help break me down, look at the website, and help break down the...