BiggerPockets Podcast 100: The 1st Deal, Management Drama, and the Birth of BiggerPockets with Joshua Dorkin

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For the 100th episode of the BiggerPockets Podcast, we bring you the interview that you’ve been asking for since the beginning: the story of Joshua Dorkin, CEO of BiggerPockets and host of the BiggerPockets Podcast.

Learn about Josh’s journey from real estate investing newbie to BiggerPockets founder — and all of the obstacles he had to overcome along the way. Get insider information on topics from starting your own business to property management and HOAs. And leave inspired to tackle your own hurdles and get your real estate endeavors off the ground!

For BiggerPockets fans old and new, this is an instant BiggerPockets Podcast classic you won’t want to miss. Get ready to learn more about the man behind the BiggerPockets curtains!

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logo_c04f5f61-f5d8-4333-a2b7-a12a07d8bfd3_mediumWe just wanted to give a shout out to our podcast sponsor on today’s show: YellowLetters is a full service marketing company that helps hundreds of BiggerPockets members find more deals and make more money.

Learn more by visiting

In This Show We Cover:

  • How Josh got started in Real Estate
    BiggerPockets-Podcast-Cover 300 300
  • The ins and outs of beginning your own business
  • Thoughts on getting your real estate agent’s license
  • How to get into Real Estate without any prior knowledge about it
  • The importance of properly assessing a property
  • What you need to know about HOAs
  • Josh’s thoughts on appreciation
  • Lessons regarding investing from a distance
  • How BiggerPockets got its start
  • Why BiggerPockets is hard on real estate gurus
  • Why you should be authentic when using BiggerPockets
  • The importance of building relationships online
  • And MUCH more!

Links From the Show:

Books Mentioned in the Show

Connect with Josh

About Author

Thanks for checking out the BiggerPockets Real Estate Investing & Wealth Building Podcast. Hosts Joshua Dorkin & Brandon Turner strive to bring top-notch educational content and interviews to our listeners -- without the non-stop pitch prevalent around the industry. With over 180,000 listeners per show, the BiggerPockets Podcast has become the biggest real estate podcast in the world. But don’t take our word for it. We’re the top-rated and reviewed real estate show on iTunes — check it out, read the reviews on iTunes, and get busy listening and learning!


  1. Ben Leybovich

    What a great show you guys! So many pieces worthy of notice!

    1. Josh is hiring Ben Leybovich, and Brandon is worried…anyone want to fill me in…?!
    2. HOA/Assessment – wow! I’ve passed on many deals due to exactly this kind of thing.
    3. Plastic people in LA…what?! Oh, yeah
    4. Better lucky than good – that is a real thing…
    5. Managing people = managing property; folks need to understand this!
    6. Detroit is the place to be! Yeah
    7. Brandon Turner – property management – climbing on roofs – poor Heather -Oy vey
    9. Brandon Turner is such a GURU!
    10. Josh – never apologize. I’ll just say it – you are smarter, and you piss us off cause we are jealous – done…
    11. Thank you, Julie!
    12. You must give, in order to receive – it’s Biblical. Not sure what’s confusing to folks about that…

    Great show. One of the best. In fact, I can only think of 2 shows that were better – 14 and 61 🙂

    P.S. To my BFF – nicely done! I could do it better, but nicely done 🙂

  2. Carolyn Lorence

    Josh and Brandon – what a great show! Josh – your story is priceless! Brandon – good job keeping the interview on track. 🙂 As I listened today I just kept thinking how lucky we are to have BiggerPockets and how much I personally appreciate you! This forum has really provided so much value and a credible platform to learn and participate in the real estate investing arena. I am so proud of where you’ve taken your business – and that you really do have the backs of your members. Your vision, values and integrity are recreating the real estate investing culture for the better.

    So, THANK YOU! I DO love BiggerPockets!! If I may quote Josh: Right on, right on! 🙂

  3. Olivia Aubry

    Loved the podcast, it was nice to get a bit more information on the mysterious Josh. Sadly, I’m one of those ghost members who listens to every podcast but never posts. I’ll definitely be using the site more.
    Keep making great shows and congratulations on your 100th podcasts!

  4. Jon Lafferty

    This was a great podcast guys, definitely top10. Josh its great to know where you have come from and what has helped shape this great community. By the way you and Brandon had me cracking up towards the end of the podcast, you guys have a great dynamic. Great job!

  5. Steph C.

    Congrats on 100 episodes! I’ve learned so much from all of these podcasts.

    I liked hearing about the origins of the Bigger Pockets name, very interesting! I also liked the reasons why Joshua started the site. I think when you set out to help people, good things will always come back to you in return.

    Back in the day, I joined a lot of those other (pre-Facebook) forums/group sites and learned from them, but I always came back to BP to learn from the investors here. Anyone who asks me about REI, I tell them to join BP and just read the forms to get started – it’s free and you’ll learn a lot. Now, I tell them to listen to the podcasts, too.


    PS – Weren’t we supposed to have those SNL skit links in the show notes? 🙂

  6. Michael Faulk

    Than you for sharing your story with everyone and thank you for the community that you founded. I am proud to say that I am a member of Bigger Pockets. I look forward to what the future holds for BP and it’s members.

    So… we have checked off the list of hearing the background of BP and Joshua Dorkin. The next item on the list is to announce the dates for the BP Summit 😉

  7. George Stewart

    Congratulation on 100 th show . Ever since i found your podcast i got hooked after listening to it. Other people would charge for the things i learn by just listening to your podcast. Thank you for BP . You Joshua Dorkin and Brandon turner are doing a great job.

  8. Jonathan Makovsky

    100 shows and you keep bringing the heat. My quick take-aways:

    1. Josh, if not for those mistakes and BP, I almost definitely would not be doing what I am today. I am incredibly thankful for what you created.
    2. Brandon, amazing job hosting. (Shameless PLUG: Today Amazon books are 20% off so pick up your copy NOW of BT’s book.)
    3. Josh is your pose from the podcast picture the same one from your “mipper” days?

    Looking forward to the next 100.

  9. Bevla Reeves

    Great show guys!!! Thank you for FINALLY sharing Josh’s story! I was on the verge of searching for it on Google, now I don’t have to! 😉

    Thank you Josh for your tireless contribution to your fellow investors, I know I couldn’t have made it this far without BP! You’re the BOMB!

  10. David Krulac

    @Brandon, just got your book, plan on reading possibly this weekend. Sent you my book, did you get it?

    @Josh, great show, you might want to read the original Walter Mitty by James Thurber, an under appreciated author. Enjoy my book.

    Thanks for the great show and the great site, continued success. I did listen to the entire show btw.

  11. What a brilliant podcast for this important milestone! Josh, you are one seriously talented, interesting and funny chap! I’ve pretty much replaced listening to music in my car, and there’s no better reason to do so. Bigger Pockets podcasts are compulsive listening. #100 was bound to be a big one, and it certainly was. The time actually flew by, and I didn’t want it to end. Two previous podcasts that have really stood out for me were Jonna’s, because the content, information, pace, and host / guest chemistry was so great; and Engelo’s because he was so hilarious, and full of energy. Josh’s story makes up my top 3 of the first 100. I certainly hope that these go on for years to come! (Oh, and when Bigger Pockets starts selling t-shirts, I’d love one with “There’s a hooole in the flooor!!”) ?

    • Joshua Dorkin

      Gavin – That’s actually not a bad idea for a t-shirt . . . I’d love to see some concepts! Otherwise, thanks for the feedback. I’m glad you enjoyed the show and I really appreciate the complements. Thanks for listening and being a part of BiggerPockets!

  12. Rich Cee

    Fellas, I just joined BP a few months ago after becoming interested in REI. I did not come across the “opportunity” of paying a guru and BP is the ONLY REI training and a knowledge source that has ever been i front of me. After this podcast I now realize how blessed and lucky I am, timing wise, to have this free resource and never having to pay a guru. Thank you gents!!!! Happy Holidays and Merry Christmas to yous both and all the BP!

  13. jerry johnson

    In this podcast you stated that a person should stay in their own backyard. Do u feel that a newbie will be okay if they go out within a two hour drive? (Example: I live between Baltimore and Philadelphia with is about an hour from each.)

  14. Julia Rowling

    OK…. I think I’m in love. What an amazing interview! I am totally inspired and know I have found a kindred spirit in you, Josh. Authenticity, honorable intentions, value-based business approach, anti-guru philosophy – you’ve got it all! Have you thought about a donate button? I would totally vote for BP with MY dollar!

    “I want the answer to the question that I asked!” Favorite quote

    • Joshua Dorkin

      Julia – Thanks for the awesome feedback. It really does mean a lot to me. We do have the ability to donate. That said, if you want to give back to BP, stay active and consider a Pro or Plus account first. Not only does it help support us, but it also gives you additional tools to assist you. Otherwise, do consider uploading a personal profile pic so people can better find you as you navigate and participate on the site. Good luck!

  15. Andres Piedra

    I liked discussion on crapy PMs. I totally agree that they need to be fired sometimes. However, they seem to be well aware that they suck, as they put in a protective clause in their agreements in that you, the owner, have to pay them X number of dollars if you fire them. It is quite amazing. I fired a PM firm who seemed to make the wrong choice 100% of the time. They were just terrible at every turn. When I fired them, they took whatever they were to make for the rest of our contract out of the tenant’s security deposit that I had to evict. How does one get around this? Yeah, they need to be fired, but how do you do it without congratulating them for their unethical and shoddy work by paying them even more?

    • Joshua Dorkin

      Andres – That sounds illegal — neither you nor a property manager can mess with a security deposit for reasons other than damages to a property, from what I understand. That money is not yours, it is the tenants. I’d probably talk to an attorney about that. I’m sure it is ok to have a penalty clause, but I don’t think they can raid security deposits to get “what’s theirs.”

      That said, it is EXTREMELY important to read your contract with a PM and if there is something you don’t like, you should negotiate it or move on and find another company.

  16. Roy C.

    Awesome podcast, Josh. I actually listened three times already! As a fellow former educator, I understand what you went through, and how teaching can be both extremely rewarding and frustrating at same time. I was always curious about how BiggerPocket was found, and I was very inspired by the principle you guys go by. As a newbie in REI, this site has been extremely helpful, and I really thank you for creating such a wonderful community, Josh. Keep up the good work!

  17. John Kubala

    I just finished listening to this podcast and I wanted to say thank you Josh for being unswerving in your commitment to honesty and integrity. Seriously. I believe that these qualities are the reason for your success and the reason I keep listening, reading, and telling others about this site.

    Thank you!

  18. Geoffrey W.

    Thank you, Josh and Brandon! Well, mostly Josh, but props to Brandon for being the personality that he is and wearing the host hat for the day (#BenLWasRight). I realize my reply is late, but still catching up after the holidays.

    Somewhat seriously, though, how many properties / units do you own now, Josh? Are they SFR, multis, commercial? Are you managing all of them yourself? I know you’re focusing on BP, but curious how far you’ve come with your RE portfolio. Sorry if I missed this in the podcast…or possibly forgot if it was in the first hour of the show rather than the second! …or perhaps the host forgot to ask these questions! 🙂

  19. Mark Bommarito

    Josh, you are so great at getting us all motivated!! I am not a frequent poster here on bigger pockets even though I joined almost a year ago. After listening to your podcast I am going to make it a point to post here on BP as much as possible so I can get involved more. I have been interested in real estate investing for years and never seemed to figure it out how to get started but feel after listening to you guys each week that Bigger Pockets will be the connection that will actually get me started. I am very glad you started bigger pockets, thank you!!


  20. Chris Tabish

    Just listened to this podcast. Josh, I REALLY appreciate your philosophy on looking out for people and providing great information. I truly believe this is what will keep Bigger Pockets differentiated and growing. I love the podcasts in general for the information they provide but now I’m a total evangelist because of the philosophy. Well done!

  21. Wow, great to hear your story Josh!

    It’s so true in life about our paths changing. Sometimes we think we are going one way when in reality we go another. One thing I’ve learned about real estate investing, it has its ups and downs — it’s definitely been a roller coaster!

    It’s great to see how BP has changed and grown. I do miss the old days sometimes but it’s also nice to see what’s new. Great episode! I see you have a sidekick now. 🙂

    p.s. I completely hear you about HOA. Nowadays, they seem to have a lot more power. I knew one person who bought a home in an HOA only finding out after they moved in how strict the restrictions were — they could not even have pizza delivered to their own house!

  22. Suzanne Beninate

    Josh, I applaud your firm commitment to staying true to your vision. Thank you, and thank you Julie.

    I’ve only been a member for a short time, but have been like a sponge! Thank you for creating content that is real, meaningful and just what I need.

    End of last year, I found myself at one of those invitations to attend a weekend event. And because I had made the decision to return to RE investing but with education. I said “yes” to the big package. While I often find myself disappointed with the decision to take a huge gamble, if I wouldn’t have done that, I wouldn’t be here. Thankful for the journey, albeit bumpy. Look forward to sharing and creating victories with my new BP family. Thanks again for creating a safe place to learn and connect.

  23. Deshawn Jennings

    Great Podcast!

    Thanks Josh for sharing your start-up experiences. Very helpful! I’m about 2 weeks in to being a BP member and have to say that this site has provided me with so much information. I’m ready to finally pull the trigger on RE investing after years and years of classes, reading and much much apprehension.

    Thank you again for this site and for sharing your story!

  24. Nathan Rice

    I’ve been listening to the podcasts from oldest to newest. Thank you for bringing Josh on as a guest. Maybe Brandan could be next…

    One of the things I really appreciated on this podcast was the detailed explanation of Josh’ condo and his reasoning for disliking HOAs. That was very helpful.

    I’d like to hear more about Josh’ investing strategy and types of investments that keep him going in real estate investing.

    Great show and thanks for opening up, Josh.

  25. Preston Johnson

    Wow, Josh really sound like a guy who built this site to help out the guys who are really trying to come up in Real Estate. I’m currently in the process of buying my first property and will be more active to show support. Thank you guys. You all are true Players in this game!

  26. Kim Stofan

    I’ve been listening through all the podcasts and just finished show 100. Thank you, Josh, for creating Bigger pockets! The site has changed the course of my life and has given me something to get really excited and passionate about. I admire and respect everything you have accomplished and I loved hearing how your journey has brought you to this point. Thanks again!

  27. Don Spafford

    Darn, the SNL link doesn’t work anymore. Guess I’ll go back to watching Dancing with the Stars. Seriously @JoshDorkin thank you so much for starting this site and not wanting to be a guru with it to let normal people be able to get valuable information to help better our lives. I am forever grateful. I just wish i could have found it years ago to have started off better.

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