YEC Member Spotlight: Joshua Dorkin, CEO of BiggerPockets

4 min read · 7 years ago


Joshua Dorkin is the founder and CEO of, the largest real estate investing community online. An entrepreneur, web designer, real estate investor and one-time realtor, Joshua was not satisfied by the online offerings of other real estate sites out there, and decided to build one himself. Mr. Dorkin’s vision for BiggerPockets has helped to propel it into becoming one of the top real estate destinations online. His vision for the site and its future has brought national press attention to both Mr. Dorkin and to BiggerPockets. Follow him @jrdorkin.

Who is your hero?

First and foremost, any list I make would be remiss without mentioning my mother, a self-made entrepreneur who succeeded in a male-dominated industry against the odds. Growing up watching her hustle allowed me to follow her trail to build my own business.

Beyond my mom, I’ve always admired Thomas Edison, one of the most important inventors in history. Despite the challenges he faced throughout his life (lost most of his hearing, tossed out of school, etc.), he became a self-made man by side-hustling. In his down time at work, he experimented and created; I followed a similar path through school and at early jobs, leading me to where I am today. Other influences include Gandhi, Ben Franklin, Elon Musk, Steve Jobs, Page & Brin (Google), and Yang & Filo (Yahoo).

What’s the single best piece of business advice that helped shape who you are as an entrepreneur today, and why?

The best piece of business advice was also the best piece of life advice I’ve received: “Do good by those around you. When you look back at your life while on your deathbed, you’ll have far fewer regrets.” I try to run my business and life by making a positive impact on those people that I come across. It is immensely gratifying to be able to run a company that helps so many people with their financial well-being.

While many may not find this to be an “actionable” tip, there are so many things that we do as entrepreneurs that can be shaped by the advice above. Whether you’re working with other companies or dealing with your customers, I’ve found that treating others well tends to generate more and more success. It can certainly be challenging, but so is business in general. Your reputation follows you forever, so be sure to shape it in a manner that you want others to remember you by.

What’s the biggest mistake you ever made in your business, and what did you learn from it that others can learn from too?

The biggest mistake I made in the course of growing my business was getting too caught up in the business to see the forest for the trees. For many years, I hyper-focused on all the details and became so caught up in the day to day that I was unable to focus on the bigger picture. I was unable to delegate and had to do everything to make sure it was done right. As a result, I delayed building a team, and for that we lost some momentum.

One day I realized that I was living Groundhog Day … I sought the counsel of a business consultant who helped me dig into my company and most importantly, he helped me see the importance of better planning. Ultimately, I’ve found that the big-picture planning requires far more focus for me. In order to overcome the inclination to just put my head down and work, I set time in my daily calendar to dedicate to it.

What do you do during the first hour of your business day and why?

While I recognize that most business coaches espouse the idea of working on the one “most important task of the day” before you do anything else, I’ve found that if I don’t catch up on email first, it always hangs over me. I now knock out my email first thing, and then turn my attention to making sure my team has everything they need to be successful at their tasks. If I can accomplish that in the first hour or so of the day, I’ve found that I’m far more free to move on and work on the tasks I’ve set for myself.

What’s your best financial/cash-flow related tip for entrepreneurs just getting started?

As someone who bootstrapped, I never had the comfort that comes from playing with other people’s money to grow my business with. I had to watch every penny, which forced me to find better, cheaper ways to accomplish different things.

While that can easily be taken to the extreme, one of the reasons I see most new companies fail is because they’re too loose with their cash — particularly those companies that have raised capital. It always breaks my heart to learn about a business that raised XXX dollars, but shut down months or a few years later because they had so much money that they didn’t know what to do with it and ultimately burned through it wastefully.

What’s ONE thing you recommend ALL aspiring or current entrepreneurs do right now to take their biz to the next level?

Continually poll your customers to find out how you can better serve their needs.

What’s your definition of success? How will you know when you’ve finally “succeeded” in your business?

I succeeded the day BiggerPockets helped someone other than me with their real estate investing. Since then, we’ve succeeded hundreds of thousands, if not millions of times.

That said, by traditional metrics, we’re also quite successful. Our traffic, membership and paid membership all continue to grow, our brand is top-notch, we’ve got a successful publishing business, our podcast tops its niche, and we’re a profitable company that has incredible employees. We’re also recognized by our peers and have had a significant impact on our industry. The goal now is to positively impact more and more people with the tools and content that we provide.

The Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world’s most promising young entrepreneurs. In partnership with Citi, YEC recently launched StartupCollective, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses.