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July 25, 2022

#336: Josh Dorkin of BiggerPockets, on Building One of the World’s Top Business Podcasts and Real Estate Communities, Trusting your Gut, and Knowing When to Exit

Josh Dorkin is the Founder, former CEO (2004 - 2018), former podcast host, and current board member of , a complete resource for learning and succeeding in real estate investing, bringing education, support, and tools together in one place. Aspiring and experienced investors alike can tap into the knowledge of more than 2 million members, and learn from content spanning across podcasts, blog, webinars, videos, virtual bootcamps, and more.


Josh Dorkin is the Founder, former CEO (2004 - 2018), former podcast host, and current board member of BiggerPockets, a complete resource for learning and succeeding in real estate investing, bringing education, support, and tools together in one place. Aspiring and experienced investors alike can tap into the knowledge of more than 2 million members, and learn from content spanning across podcasts, blog, webinars, videos, virtual bootcamps, and more. BiggerPockets’ mission is to help people find personal freedom and financial flexibility through real estate investing.

Josh created the platform in 2004 to create a place where investors could learn, network, market and make deals in a safe online environment. Growing, bootstrapping, and exiting BiggerPockets after 14 years taught him innumerable lessons. He overcame the countless challenges and learned how to build a nationally recognized brand, launch products, build teams, create partnerships, remain profitable (every year since launch), fail fast and pivot, challenge the status quo, and much more, ultimately helping to transform how real estate investors connect, collaborate, partner, and learn via best in class web, mobile, audio, and video content.

Topics Covered by Josh Dorkin in this Episode

  • Josh’s background and why he originally started BiggerPockets in 2004
  • The journey from almost quitting to growing and scaling to a successful exit
  • Why Josh waited 8 years to hire his first employees and his advice for other founders
  • Hiring his first employee directly from the BiggerPockets community
  • The evolution of creating engaging content and expansion into different media platforms
  • The “chicken or the egg” challenge of building a thriving community and being selective about partnerships
  • What drove Josh to persevere throughout a decade of challenges even when he wanted to quit
  • The tipping point Josh came to once he hired middle management and began to establish infrastructure within the company
  • What Josh attributes BiggerPockets’ success to
  • Josh’s thoughts on investing in the current real estate market
  • Josh’s perspective on defining success
  • How and why Josh got involved in startup investing

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