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Driven & Co. Ep: 26 – When the Teacher Becomes the Master – One Entrepreneur’s Journey to Educate Real Estate Investors

Joshua Dorkin is the founder and CEO of BiggerPockets. This week host Justin Gray welcomes Josh on to talk about the biggest real estate mistake he ever made, how it inspired him to start a company to educate and empower real estate investors, and what it was like to be a solopreneur for eight years before scaling his team.


What is BiggerPockets?

BiggerPockets is the leading real estate investing platform community – it’s where you go if you want to learn how to become a real estate investor and reach financial independence. We have an amazing community of more than 800,000 members. We’ve got some incredible content – podcasts, videos, blog articles – and we put together tools to help real estate investors succeed.

What’s an average day for you look like?

For the first eight years of the business, I never raised money so I did everything from sales, marketing, customer service – even product design. Today, we have a different structure. We have team leads. We have folks in charge of product, marketing and engineering. My days are spent guiding the strategy, making sure people have the tools and resources they need to be successful and accomplishing what it is that they want to accomplish. Frankly, I spend a whole heck of a lot of my time learning, reading, listening to podcasts, talking to people, and trying to learn how to do this job.

What did you want to be when you grew up when you were a kid?

I wanted to be an actor, a scientist…probably a veterinarian. As for how I became interested in real estate, my college roommate and I had rented an apartment and didn’t really think too much about it. But then one day we were like, “Why we paying this guy rent? Why do we continue to make this guy rich? Why don’t we buy this building and pay ourselves rent or have somebody else pay us rent?” That’s why I do what I do now, because I want to take folks who have that thought, or think it’s impossible, and show them it is possible.

You’re the son of two entrepreneurs. How critical do you think that is to influencing one’s entrepreneurial mindset versus someone who grew up in a more traditional household?

It is helpful. The thing that I got out of living in a house of entrepreneurs is I saw how hard my parents worked. They knew the harder and the smarter that they worked, the better the opportunity would be for them and the family. Now I’ve got three little kids and we talk about entrepreneurship. I teach them about the value of hard work. We introduce them to entrepreneurs. We talk about business and things like that. My kids are likely to be entrepreneurs, or at least, they’ll have an entrepreneurial mindset wherever they end up doing. Anybody can get this mindset. I don’t think it’s born with you.

How did the idea for Bigger Pockets come about?

Post-college I had a handful of careers. I was in the entertainment business. I was a stock trader. I got a real estate license and sold real estate. And ultimately, I ended up as a special ed teacher. My brother had picked up a bunch of property where he was living in the Midwest, so I flew out and looked at his properties. I did the math. I knew the numbers were great and I was gonna make money. It was that easy. Right? Well, yeah. Except that I lived 2,000 miles away. I couldn’t go and visit the property. I couldn’t go and look to see what my property managers were doing. I had to trust people that I didn’t know. And I bought properties in bad, transitional, but mostly bad neighborhoods. I made a handful of mistakes. Very quickly, despite what the numbers said in a spreadsheet, reality smacked me in the face. And I started to lose money on properties I should have been making a lot of money on.

I realized that something needed to change. How do I get answers? What do I do? How do I solve this? I looked at the landscape and all I saw were the get-rich-quick guys. I didn’t buy into it and thought, “I’m going to create a website that helps me get the answers to my questions in a way that I feel comfortable with, in a way that I don’t feel like I need to take a shower.” I started building this community to help me to find the answers to my own questions.

And how long did that take to become your full time gig?

After two years, I quit my job and went full time. At the time, I was probably making less than $10,000 a year from the business. My wife was doing well and she said, “Hey. I’m gonna support you in this and let’s see what we can do with it.” That gave me the ability to kind of slog through the lean years and get to a point where eight years later I was making a pretty decent living, but I had no employees and was working 80 to 100 hours a week. I was burnt out and miserable. At that point, I sought out the expertise of people smarter than me and decided to start scaling it into a real business from this lifestyle business that I had created.

To find out more about Joshua Dorkin and his journey to becoming an entrepreneur, including what he looks for in new hires, click here to listen to the entire interview. Plus, visit BiggerPockets.com, find Josh on LinkedIn and tune into his BiggerPockets Podcast here.

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