Josh Dorkin Bootstrapped BiggerPockets to a Big Exit


Dan Daugherty interviews Josh Dorkin who founded BiggerPockets in his living room with $12 bucks. Josh tells his story of wanting to quit, having 3 nervous breakdowns, and eventually selling to a private equity company. Josh talks about what he did to get to a place of happiness and how big changes in his life became catalysts that helped him, his family, and the business grow. 

Beginning Transcript

Dan Daugherty - Welcome to this episode of The Big Exit. I'm your host, Dan Daugherty. And today I have a good friend, Josh Dorkin who is the founder and former CEO of BiggerPockets. Josh, thank you for coming on the show. 

Josh Dorkin - Excited to be here, man. 

Dan Daugherty - You know, I've got a lot of feedback from the listeners that said, Hey, big exits are great, but I noticed that a lot of the founders that you have interviewed have raised significant amounts of money, and I immediately thought of you because you've bootstrapped BiggerPockets from I remember your Washington Park house where we met to really a multimillion dollar organization. And I'm excited to have you on board to really tell the story of how you went from zero to an exit without ever raising a single dime of outside capital. 

Josh Dorkin - Well, if you put it that way, it sounds pretty good. Yeah, Yeah, I I mean, you know, you want me to just take it from the beginning, or..

Dan Daugherty - Yeah, let's start from the very beginning. I remember you and I met In, must have been, what? When did you found BiggerPockets? 

Josh Dorkin - Yeah. So it must have been 07, maybe that we connected and you and I were talking about, you know, you were thinking about buying different companies, and and we were just chatting about that. That didn't go well for me, but, uh, but yeah, no, it's been, um it's been a very, very long journey. Um, you know, like like any entrepreneurial story, lots of ups, lots of downs. And, um, inevitably, um, you know, really struggled through those those difficult times. But, you know, I think the key was just persevering through those in order to come out at the end. But, um, I I looked at the cycle as a multistage cycle. When I started BiggerPockets, it was I was teaching special Ed. I was teaching high school in Los Angeles. 

The company, by the way, is the largest real estate investing media company and community out there. We're all about trying to help people build wealth, learn how to build wealth through real estate investing. And so back in 04 I was living in Los Angeles, I was teaching special ED at high school, I bought a bunch of property, as a result of my brother encouraging me to do so. And, uh, you know, I thought I was a smart guy, I went to college, you know, all these all these things and bought property thousands of miles away, which would would normally be a challenge. But I didn't really do my homework. And so what happened was little by little, I found myself running into some problems and I didn't quite know how to deal with those problems. There were books, but like, you know, the books were pretty general. They didn't really say, What do you do when your tenant is stealing electricity from the building next door? What do you do when somebody is ripping the copper piping out of your vacant unit? You can't find that. And all that was out there were there were communities forums, but they were all kind of tied to or in cahoots with, I call them the Gurus that get rich quick crowd. Um and you know, the the issue I had with with those which led me to founding BiggerPockets, was I You know, I didn't like the idea of getting caught up in this this funnel where, you know, it's like, hey, come to our free course and the free courses. Just an ad for a free boot camp. You know, some kind of boot camp, which is a nad for a course, which is an ad for, you know, training.

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Episodes (8)

Episode 4 · 5 months ago

The Story of eBags from Inception to a $105MM Exit

Jon Nordmark, the co-founder of eBags, tells his story of risking it all to start an Ecommerce company, surviving the dot com crash and avoiding bankruptcy during 9/11. His company's resilience and magical culture helped them launch new products when they needed it most.

Episode 3 · 5 months ago

Lori Torres - Going from Borrowing Money to a $100+MM Exit in 4.5 Years

Lori Torres left a high-paying job, had to sell her home, and borrow money from her mom to get her company, Parcel Pending, off the ground. Due to her personal frustration and knowledge of where online shopping was headed, Lori saw a tremendous gap in the market for making it easy and secure for apartment residents to receive and collect packages 24 hours a day. She took her idea and turned it into a $100+MM exit in record time. This is her story.


The "Elf on the Shelf" moment. 

Culture and customer service that led to a $100MM Exit. 

Risking it all and believing in the idea. 

What does being an entrepreneuer mean to Lori? 

Sample Transcription

Dan Daugherty

Today, I have very special guest who I've known for about six years, all the way back to when she was trying to get her company off the ground, and since then she has built one of the largest companies within the package delivery space and last year in 2019 sold her company, Parcel Pending, for over one hundred million dollars. Lori Torres. Thank you so much for taking the time to speak with us today.

Lori Torres

Hey Dan, so happy to be with you. Thanks for having me.

Dan Daugherty

Well, I wanted to start this off with a two part question. The first is what is Parcel Pending? And I know you had a very lucrative job before you started Parcel Pending. What made you decide to leave that cushy job and take the leap into starting your own company?

Lori Torres

Yeah. So, first off let me tell you what Parcel Pending is. We do electronic smart lockers and so invision a bank of lockers that have technology in them and we put them in apartment buildings at office buildings, in retail and so couriers can come deliver the package straight into the locker. They find the recipient and then it sends a text, an email to the recipient, and now they get this text for email with the code and they can go to the lockers and pick up their stuff. It's a safe and secure way to get our packages and contact free in the world of COVID. So it's a great solution to a huge growing problem because everybody is shopping online and they want to get their stuff, but they don't want it stolen off their front porch. So that's what Parcel Pending is.

So let me tell you what happened was I was at a fancy corporate America job. I was in the apartment business running 44,000 apartment units with about 1,200 employees and my staff kept asking for more headcount and bigger package rooms because the residents were home in their pajamas shopping online and all of a sudden they were just inundated with packages and so I was like, we can't add headcount, that's an expense, it doesn't make any sense. So I thought, you know we could solve this with technology...

Episode 2 · 6 months ago

A Big Exit and A $150MM Mistake - Dave Borden and Selling Too Soon.

Dave Borden, who sold his first business for $19MM tells his story on what it takes to be a serial entrepreneur, selling too soon, and the definition of what "entrepreneur" really means.


Sample Transcription

Dan Daugherty

Welcome to this episode of The Big Exit. I'm here with Dave Borden who sold his company in 2006 for $19MM. I wanted to structure this episode a little bit differently and actually get into the psyche and the mind of serial entrepreneurs and Dave has built multiple companies throughout the last couple decades. Some have been successful and some have failed, but we will talk more about his story. Dave, thank you for joining me.

Dave Borden

Thanks for having me Dan, we'll talk more about the success hopefully, but yeah, there's probably a lot more to learn from the failures but the successes are obviously more fun. So..

Dan Daugherty

Well, let's start at the beginning, even in childhood, you grew up in Colorado Springs, correct?

Dave Borden

Yeah. I grew up mostly in Colorado, but yeah, probably from about sixth grade on I was in Colorado Springs.

Dan Daugherty

And did you always want to start a company, or were you influenced by your parents? Were they entrepreneurs?

Dave Borden

Yeah, from a very young age, I always wanted to have a business of my own and I didn't really know exactly what it was, but both my parents were, they were entrepreneurs and they still are. And so I grew up from about the age of five where my family never worked for anybody else, and they always were able to provide plenty of income and do well. So I guess I was never scared of starting a business and I've only worked for, other than my time in the army, in a very brief stint in corporate America, I've never never worked for anybody other than myself.

Dan Daugherty

Did you, you know growing up, even my mom actually ran Daugherty Construction and she also built pools. But one of the things I remember is that she was always stressed out about money. Did you see that at all with your family?

Dave Borden

Okay, a couple rare times? Yes, I will say, my dad. I love him to death. He's also one of the most frugal guys I know. So, he never had a desire for fancy stuff and he was always very good at saving. However, we did have a pretty rough time and I think it was early eighties, like eighty one, eighty two, we used to live in Steamboat actually and it was before the big ski boom. So they had, they owned a bunch of property in real estate and they've always been into real estate and investing but the market really went sour, nothing was selling and even though I know we had some good savings, I know it dried up pretty quickly and that's the point where we pretty much moved.

We were forced to move to Colorado Springs just because there wasn't any income there. I think my dad actually took a job at a hardware store for about six to twelve months just to pay some bills. We didn't really have many bills like I said, my dad was very frugal. That was a pretty rough time and I think they just decided that we needed to pick up and go somewhere with a little more opportunity.

Dan Daugherty

Subconsciously, do you think that helped transform your ideas, your ideals, and your thoughts about starting a company?

Dave Borden

Well, I think I was pretty young at that time. I'm 48 now. I think at that time, I was under ten, maybe eight or nine, maybe ten. Well. I don't know, sixth grade whatever that is, ten, eleven, twelve, something like that. I did see you can feel the struggle, even though my parents never talked about it, but we were okay and I don't remember ever a time with my parents that we, you know, had bill collectors calling or we were late on mortgages.

Episode 1 · 6 months ago

Going From an Idea to a $57MM Exit - A Discussion with Founder Justin Alanis

Justin Alanis took a personal frustration within the rental industry and turned his idea into a $57 Million all cash acquisition. In this episode, Justin shares his story on raising money, having less than 3 months of cash left, and what eventually led to a major acquisition by Real Page, a $7 Billion publicly traded company.

Justin describes how he went from an idea to getting his first $25k check from Sean Conway, his good friend, to help with getting things set up. He leveraged FOMO (Fear Of Missing Out] and salesmanship to sell the idea to customers before a single line of code was even developed. This led to his first $1.2MM seed round, which eventually led to raising over $20MM from institutional VCs and ultimately an exit. This is his story.


Transcription Snippet

Dan Daugherty

Welcome to the very first episode of the Big Exit, I'm your host Dan Daugherty and I'm very excited to have Justin Alanis as my first guest. Justin built and sold his previous company for $57 million in cash to Real Page in 2018. Justin, thank you for joining us.

Justin Alanis

Thanks for having me Dan, I did not realize that I would be the first guest, I'm honored.

Dan Daugherty

Well, thank you and, as you know, we go way back. For the listeners listening. I met Justin - Gosh, probably what seven or eight years ago when you first closed your seed round and we were at a conference - I think in San Francisco it was probably AIM or NAA and you had a small little booth. I think it was you and one other person and you and I hit it off. Fast forward eight years later and you having a really big exit to Real Page, which is a publicly traded company worth about seven billion dollars.

Justin Alanis

Yeah, it was an amazing journey now that you think back all the way back to that time. Probably when I met you, we probably didn't even have a product yet. Frankly, we were probably pitching vaporware at the time, but ultimately, as you know, we were able to build what our customers wanted and yeah did have a a relatively successful exit to Real Page at the end of the day.

Dan Daugherty

Well, let's start at the very beginning. why did you build Rentlytics? What challenges or problems were you solving for?

Justin Alanis

I think, like a lot of other entrepreneurs who don't come from the tech world or maybe even some that do come from the tech world, I was solving my own personal frustration in my previous job. I started my career in commercial real estate - private equity and I bounced around to a couple of different companies and started out as an analyst early on and then rose up to becoming a VP and partner at a large real estate private Equity Company.

All throughout my journey. I saw the same problems over and over again. The problem really revolved around data and access to information. It was crazy to me that I was running a multibillion dollar portfolio and yet I didn't have access to my information, except on maybe a monthly or quarterly basis.

The information was not that good when I got it. It made no sense to me that I could not get access to information in real time to be able to make more sophisticated and data driven decisions across my portfolio. So I I moved to San Francisco in 2010 to be with my fiance at the time, now my wife, and I saw my other friends in technology.