Joshua Dorkin built BiggerPockets. Then he made room for a life.

Joshua Dorkin’s friends had a joke about his business. They would ring him after passing a penny on the pavement and offer to mail it over. The founder of BiggerPockets was helping people think about getting richer; his own enterprise could apparently use the loose change. A dependable salary had gone, a website had taken its place, and his friends had acquired material.

Years later, the joke reads rather differently. By October 2017, BiggerPockets had more than 870,000 members. Yet the penny belongs in the story. It preserves the awkward stretch before the numbers became impressive, when other people could see an unpromising website and Dorkin could see a reason to keep answering questions.

That distinction runs through his career. He has tried acting, teaching, property investing and publishing. He built a business around people sharing what they knew, then handed its daily operation to others. The ambition changed shape along the way. So did his definition of a good day.

A landlord in search of an answer

The future founder grew up in New York among entrepreneurs. His mother ran a retail business; his father was an electrical contractor. At Washington University in St. Louis, he studied marketing and political science. Business ownership was familiar territory, even if his route towards it resembled a collection of diversions rather than an itinerary.

In college, Dorkin and a roommate considered buying the building where they rented an apartment. Their rent was about $450 a month between them. Why keep paying somebody else? It was an appealing question with several inconvenient follow-ups. They lacked the knowledge and money to carry the idea through, and the proposed landlord careers remained theoretical.

After college came a short spell trading stocks, followed by entertainment work in New York and Los Angeles. Dorkin acted, produced, worked around talent representation and helped find scripts. He also obtained a real estate license. Selling property failed to hold his interest. A substitute teaching credential eventually led to a full-time classroom job.

His brother encouraged him to look at investment properties. Dorkin bought small apartment buildings far from his California home and discovered that ownership came with questions that enthusiasm could not answer. He wanted practical help. The online communities he encountered seemed too interested in selling him the next expensive course.

He already knew some basic HTML and had experimented with websites in college. So he gathered useful resources, learned more and built a forum. BiggerPockets began in 2004, while he was teaching. The premise had the plainness of a good classroom question: could people with experience help people who needed it, without every conversation ending at a checkout?

“I had property. I had questions.”Joshua Dorkin, BiggerPockets Podcast 100

The name had already auditioned

Even the company’s name took a detour. Dorkin recalled hearing an actor in a film struggle to pull a wad of cash from his trousers and complain about needing bigger pockets. The phrase stayed with him. He initially used it for an entertainment-industry community, an idea he abandoned before putting the name to work in real estate.

It is a pleasing piece of entrepreneurial recycling. A name intended for actors became attached to rental properties, discussion threads and deal analysis. The acting ambition did not have to succeed for something useful to survive it. Dorkin’s history contains several such unfinished experiments; he has never presented himself as someone who chose correctly at every junction.

For two years, he worked on the site around teaching. Then he left the classroom, married, moved to Colorado and committed to BiggerPockets full time. Advertising brought in small amounts. His wife, Julie, supported the household during the early years. A founder may own the website, but the household still has to finance the faith.

No sales table at the back

By April 2012, the community had 85,000 members and roughly 300,000 unique monthly visitors. Discussion ranged from the modest problem of replacing a shower head to the considerably less modest problem of investing across state lines. A deal-analysis forum let members put prospective purchases before other investors. The usefulness was often in the particulars.

The site earned revenue from advertising and paid memberships alongside free basic access. It was already a business, with the ordinary need to cover costs. Dorkin’s objection concerned how education was delivered and what people were being led to expect. He wanted a place where getting an answer did not require submitting to a procession of sales pitches.

He carried that preference into a 2012 investing summit in Denver. Speakers had to sign agreements prohibiting upselling. Teaching was the assignment; a sales table at the back of the room was outside the brief. It was a practical rule, easier to inspect than a stirring statement about putting the customer first.

Eight years to make room for someone else

Dorkin describes Brandon Turner as his first full-time hire, eight years after the founding. Together they developed the BiggerPockets podcast. A forum gives people somewhere to ask; an interview gives them someone to listen to. The conversations brought the experiences of individual investors to people who might never have met them otherwise.

The long wait to hire was also a mistake Dorkin later acknowledged. He had become absorbed in details and reluctant to delegate. A consultant helped him think about planning, and he began setting aside calendar time for the larger questions. Getting through the work and deciding which work mattered required different habits.

His business advice could be refreshingly unceremonious. Ask customers how to serve them better. Watch the cash. Treat people well because a reputation travels. He also admitted to clearing email first, despite the familiar advice to start with the day’s most important task. Apparently even a founder’s inbox is unimpressed by management literature.

Publishing extended the enterprise further. In 2018, Dorkin and Turner released How to Invest in Real Estate, a beginner’s guide built around different approaches rather than a universal prescription. It included more than forty investor stories. The choice of strategy depended on a reader’s resources, goals and circumstances, an appropriately untidy answer to a subject often sold as a formula.

The founder and the job parted company

Growth changed Dorkin’s working life. He enjoyed making products, experimenting with marketing and building the community. As the organization expanded, more of his time went towards managing people who did those things. The company could be doing well while his own job became less appealing. Recognizing that took him time.

By his departure, BiggerPockets employed more than forty full-time staff, with additional contractors. In November 2018, the company announced a partnership with McCarthy Capital. Scott Trench was CEO, and Dorkin remained an investor and board member. The announcement put membership at nearly 1.2 million. The business had acquired a scale that its early advertising checks scarcely suggested.

Looking back, Dorkin identified a preference for smaller organizations, perhaps around fifteen employees, where a founder could still participate directly in making things. That is a useful admission from someone whose company had grown beyond it. Success had not abolished personal preference. It had made the mismatch harder to ignore.

In his 2022 anniversary reflection, he described his involvement through occasional calls and quarterly board meetings. He took pleasure in the company developing a life beyond his daily attention. For an enterprise built around sharing knowledge, sharing responsibility was a fitting, if considerably more personal, next lesson.

More room in the day

Dorkin moved to Maui in 2020. His interests there include surfing, paddleboarding, tennis, hiking and gardening. He is building a permaculture food forest, a project with a rather different timetable from a publishing calendar. Family time and adventure feature prominently in how he describes the life he wants.

He also kept an interest in other people’s ideas. In January 2020, he launched Undeniably Curious, a long-form interview podcast whose archive remains on YouTube. His later work includes mentoring entrepreneurs, advising startups and seeking opportunities to contribute on boards. On LinkedIn, he has publicly discussed advising Invelo, the real estate software business founded by Justin Silverio.

In October 2023, Dorkin announced that Threads would become his main place for online conversation. He warned readers expecting a steady stream of property advice that his interests had broadened: technology, sustainability, angel investing and startups were among the subjects occupying him. The founder of a real estate community had given himself permission to discuss other things.

BiggerPockets continued its own expansion. In August 2024, it announced a majority investment from The Chernin Group and more than three million members. Those are milestones in the company’s later history, beyond Dorkin’s tenure as CEO. They also give substance to his hope that the thing he started could continue without requiring him to steer it every day.

On the site’s nineteenth anniversary, he remembered the opposition that greeted his decision to leave teaching. He encouraged people to try the ideas they kept postponing. The advice has more texture coming from someone who spent years waiting for a business to pay him properly. He knows that taking a chance can involve an uncomfortably long interval before anyone congratulates you.

The penny joke has survived that interval. So has the original usefulness of putting people with questions in touch with people who might answer them. Dorkin now has space for other conversations, other founders and a garden. A business called BiggerPockets has, at last, made room for a few things that will not fit in a pocket.