Written by Jason Myers

Passion. Zeal. Fanaticism. All of these adjectives easily describe how Josh Dorkin, founder and CEO of BiggerPockets feels about real estate investment. That passion was live and on display, at times almost palpable, at the January edition of the Denver Founders meet up.

The guiding idea behind BiggerPockets is that anyone can build their own source of wealth through real estate investment. Doing so takes hard work, but BiggerPockets provides the resources and educational materials necessary to put people on the path to success in the real estate realm. Oh, right. All of the content that BiggerPockets produces is free, too.

Today BiggerPockets consists of a social network with over 440,000 members, and its forums average between 2,500–3000 posts per day. There are BiggerPockets groups that meet regularly all around the world, sharing tips and ideas, and learning from each other and the broader BiggerPockets community.

How does a company go from one guy in his basement blogging, to having 200 acolytes in South Korea that meet monthly as a result of the BiggerPockets network?

That question has already been answered: With passion. “If you don’t have passion about your startup you should stop right now,” said Dorkin. You’ll notice that the ways in which that passion manifested itself, the steps along that yellow brick road, if you will, are revelatory in their own right.


Dorkin, who has an option of doppelgangers as he bears a striking resemblance to comedian Jimmy Pardo or musician Adam Levine, entered the real estate world in a roundabout way. Admittedly a man who tried his hand in an eclectic range of professions, Dorkin found himself with a substitute teaching license. His first assignment was in a special education class at a school in California. In a twist of fate, that same day the teacher he was substituting for, quit. Dorkin remained in that position for the next four years.

While teaching, his brother, who had, at that time, recently acquired some investment property for himself, encouraged Josh to do the same. So he looked into the idea. Among other things, Dorkin had obtained a real estate license previously, but didn’t end up enjoying that particular corner of the real estate world.

Nevertheless, he ended up buying some property thousands of miles away from his home, and relied on local managers to oversee his property. Things went south quickly, and while hemorrhaging money on the investment, he started to look for help on turning things around.

Unfortunately, there wasn’t any good, free information available for anyone trying to educate themselves on real estate investment. Sure there were plenty of scams and pyramid schemes that promised to help you unlock the mysteries of the industry, and although a sucker may be born every minute there’s no point in unnecessarily perpetuating that maxim.

So Dorkin dug in, like he did with every new job or opportunity he pursued in his life, and took matters into his own hands, educating himself from the ground up on what was what.

Attracting Users

Dorkin had a bit of web development experience and started out by spending his nights and weekends creating a website and phpbb forum of real estate investment resources. Dorkin also spent time on internet forums, typically in the off-topic sub-forums answering questions about real estate when they cropped up. Sure enough, people started to click on the link to his website in his forum signature and the traffic on his website started to grow.

He began blogging about real estate investment back in 2004, while he still had his day job as an educator. While blogging is ubiquitous today, it wasn’t in 2004. Dorkin noted that the only notable blogger at that time was Wil Wheaton of Star Trek, and later The Big Bang Theory, fame.

So Dorkin dove headfirst into an emerging medium with the goal of creating useful content. If that sounds familiar it should, because nowadays we call that content marketing.

As the site progressed, Dorkin wanted to build a professional site so he outsourced the web development work to a shop somewhere across the Pacific Ocean. Thousands of dollars later, what he got for his money was a crappy site that didn’t work. He never even activated it.

This proved to be one of several Rubicon moments for Dorkin. By this point he was several years into the BiggerPockets project and had recently left his teaching job. In other words, the timing wasn’t great for a derailment like this.

He’s not the first to say “I was too stupid to quit” and certainly won’t be the last, but a couple of things spurred him forward: his passion for BiggerPockets, and dogged pride.

Playing a Two-Man Game

In sports the “two-man game” is a game within the game, like the movie Inception, where teammates have an innate understanding of what the other is going to do and can improvise around each other for successful outcomes.

Dorkin’s two-man game involved him and a developer. Instead of doing everything all at once like he did previously, Dorkin changed his tack and opted to build things piecemeal. (Here’s another example of a lean startup before that was even a thing.) The developer crushed it at adding features to the site. They started with user profiles and built out from there. This was around 2004 before social networking really existed. (Remember the halcyon days of MySpace? Bueller?) They also transitioned the site from a Frankenstein mishmash of code to a stable Ruby on Rails-based site right around the time Ruby first emerged.

This left Dorkin doing everything else: marketing, advertising, public relations, and most importantly, creating content. Now there’s a certain appeal to working at home, and Dorkin had that in spades at this point, but to working to the tune of 80–100 hours per week is an unsustainable pace. But after eight years it became clear that BiggerPockets needed to change, if for nothing else Dorkin’s sanity as his lifestyle business became a life-consuming business.

Making the Leap

To avoid getting burned out, in 2011, Dorkin hired a consultant to help him make sure everything was properly structured and organized. With this external perspective it became clear that he needed to narrow the focus of the company, but also whether the right move at that point was to either shutter the company or try to sell it. A man’s well-being was at stake here after all.

Once again, Dorkin’s dogged determination wouldn’t let him hang up his spurs so the next question became what to hire first? This proved to simultaneously be one of the scariest and best moments for company, but upon reflection Dorkin said that that first hire was when it really felt like a company.

His first non-technical hire took over content creation and virtually fell into his lap. He was a forum member who had successfully amassed enough wealth through real estate investment–thanks to BiggerPockets­ that he didn’t need to work. So Dorkin got a unicorn employee right off the bat: someone with deep experience in the industry, an evangelist for his product, and someone who wasn’t in it for the money. Most critically, his passion matched Dorkin’s and now they’re two of the most important and relevant people in the real estate space.

A Meteoric Rise

Since making that first hire, BiggerPockets moved out of Dorkin’s basement and hired more employees. The company currently has a staff of twenty employees and continues to grow. All of this was accomplished with a grand total of $0 in investment dollars and over the entire life of the company, BiggerPockets has only spent a few hundred dollars on advertising.

Dorkin experienced a professional shift almost overnight. He shifted from being the jack-of-all-trades, the guy doing everything, to the role of CEO where he manages and delegates. He admits to being an extremely self-reflective individual, and has jumped into the water of learning how to be an effective CEO with the same vim and vigor as everything else he does.

The same passion that propelled Dorkin through every watershed moment in the company’s history continues to fuel him and BiggerPockets. Without passion you won’t survive, “if you’re not passionate about that which you’re getting into you’ll be miserable”

Instead of relying on a single revenue stream, BiggerPockets focused on diversifying its delivery channels. The company has added its own publishing wing in addition to dominating digital content (these books are the only content the company charges for). The BiggerPockets podcast is in the top 10 business podcasts on iTunes and just on the cusp of the top 100 overall podcasts on the entire platform. The need to provide the absolute best content in the real estate investment space spurs Dorkin onward. By creating killer content in every medium the company touches, BiggerPockets has been able to expand its reach and build its brand. By spending years understanding his users and what they needed, Dorkin was able to create content that people wanted to read. A cliché as it sounds, users simply followed the great content.

Given the unpredictability of the financial future, Dorkin sees real estate investment as a stable option to safeguard against financial doom down the road. With almost half a million people who agree with him, it looks he’s really on to something.

Jason Myers
Jason Myers is a skilled technical writer and editor with background in data analysis and research design. A proven performer in the creation, composition and evaluation of documentation and web-based content for technical and non-technical audiences. He is experienced in cultivating brand voice through written content and utilizing digital technologies (such as SEO) to increase reach and conversions. Visit his website http://contentdoctor.net/.