It is always interesting to see what kind of things come up when you search for yourself online.

In my case, the two things most searched are my net worth and why I left BiggerPockets.

I already dove into the former.

Why I left BiggerPockets is a little more complicated…

The company is one that I founded almost 18 years ago and left back in November 2018 after undertaking a recapitalization via McCarthy Capital, a private equity shop out of Omaha.

The Hobby that Turned into a Lifestyle Business

When I founded the company I was teaching full time at a special ed high school in the Los Angeles area. I had purchased a few rental properties and needed some help dealing with all the questions I had, but couldn’t find a place where I could get answers without having to deal with solicitations and promotions of these self-proclaimed gurus who dominated the scene at the time.

While teaching, I began to build a directory of resources and a forum which were the roots of today’s community and platform. For two years I taught and in my free time I coded and built this budding hobby into something that trickled in tiny advertising checks.

After two years, I quit my teaching job, got married, moved to Colorado and began working full time on BiggerPockets. Keep in mind that full time in this case means 80-100 hours a week, with no days off, no vacations, no respit. I kept this pace up for over 8 years . . . something that I used to think gave me hustle street cred, but today I realize was just a formula for burnout.

From Lifestyle Business to Company

Six years later and a full eight years after I founded the company, I hired my first full-time employee, Brandon Turner, who helped me create our podcast and was crucial in the next stage of growth of the business from lifestyle business to full fledged company.

We grew the platform and its offerings. We grew the community. We build tools, our content, our social presence. We launched a book business. The list of accomplishments goes on and on, but with this growth came the need to hire, and that we did.

By the time I exited, we had over 40 full time employees, and around a dozen contractors - close to sixty people working for the business. It was a lot to manage and with it came all the headaches that come with growth.

There were personality clashes, bad hires, and everything else you could imagine.

The days of building product, building community, marketing, growth hacking and being creative were replaced with days managing people.

This is the dream.

Almost everyone that builds a business wants some kind of growth, but as much as I loved seeing my brainchild thrive and grow, I was having less and less fun doing it.

I LOVED the first few years of hiring and scaling. It was a blast, but by year 12, 13, 14 my job changed. Instead of getting my hands dirty building product or testing some new landing page or campaign, I was overssing someone else that was.

My excitement for the company and brand never waned, but I really stopped loving going in to work, but didn’t know it. This ultimately led to me having several panic attacks which really should have been a sign to step back.

As always, I charged on despite my body and subconscious screaming as loud as possible to stop.

Tragedy Strikes

In November 2017 one of my daughters went through a terrible trauma that was initiated by a surgery - something called conversion disorder. For us, it manifested in my little girl becoming neck down paralized amongst other things.

There are few things worse than seeing your child suffer and this period was easily the worst of my life.

I immediately stepped back from the day to day at work and handed charge to my number two at the time, Scott Trench in coordination with Brandon.

I remember the exact phone call that I made to the two of them to tell them what was going on. It was brutal. While they sat in shocked silence, I wept for what seems like an hour as I tried to explain what we were dealing with - barely getting the words out — mostly just crying out loud uncontrollably.

The two of them promised me that they would take care of the company in my absense and they certainly did that and I am of course, eternally grateful.

Days and weeks of not knowing what was to come with my daughter eventually led to glimmers of hope that we’d see a recovery. I spent countless hours caring for her full time - feeding, moving, and working with her to accomplish tiny wins like the movement of a single finger or opening an eye. It was excruciatingly slow and frustrating, but we never let up. Along with a team that we put together including physical and occupational therapists, we began to see the wins rack up and by February/March of 2018 she had progressed from her wheelchair to walker to finally walking by herself.

Hope

This terrifying situation broke us, but didn’t defeat us.

I began to feel hopeful and knew at some point we’d all be able to move on - no matter the outcome.

Of course, it took many more months of work and ultimately several years for her to get back to 100%, but with time, energy, an amazing team, and unlimited love, she has since fully recovered from the incident.

We’ve climbed mountains, traveled, explored and journeyed, surfed, skied and have never stopped seeking out a full and rich life.

Deep Contemplation and Happiness

Over the months and months that I spent caring for her, I had something I had never previously had in my adult life - time. I had time to wonder, time to wander, and time to contemplate my life and my happiness.

I realized that over the past fourteen years as CEO and sole founder of BiggerPockets, I sought out success, fame, fortune and accolades, as most people do, but despite achieving all of those things, I just wasn’t fully happy.

Of course I was happy to have an amazing loving family and a successful business. I was happy to have three amazing children, food on the table, and a safe place to live.

I wasn’t, however, happy with what I had spent my time doing.

I was no longer happy as CEO of my own company.

That’s a really weird thing to say, especially since I loved the company. Separating the job from the company took a lot of time for me to do, but the realization set me on a path to where I am today.

Once I realized this, I instantly knew what I had to do. It was time for me to step down, bring in partners, and move on from the day to day running BiggerPockets.

We engaged an investment bank, initiated a process, and ultimately found ourselves at a successful deal with our aforementioned partners.

Leaving BiggerPockets was very difficult - probably similar to sending your child off to college, but I did so both because it is was I had to do, but also because it was what was best for the company.

I love being an entrepreneur, but I simply prefer working at a smaller company - the sweet spot for me is probably up to 15 employees or so. It is big enough that you’re not doing everything, but small enough that you can still get your hands dirty when you want.

Transition

Post close, I joined the board of directors, but no longer was involved in the day to day decision making at the company.

Of course, this was an extremely difficult transition for me, but I believe that several years later, I have become a highly valued board member that contributes immensely to the business and I’m hopeful that I can find other opportunities to do the same for other companies.

I get to advise Scott and the current leadership team alongside some incredible partners.

BiggerPockets has grown quite a lot since I’ve left, and I’ve enjoyed watching it take on a life of its own without me steering the ship.

As a father, this is what I’m excited to see happen for my kids soon, and as an entrepreneur, I can’t imagine being more proud than building something amazing that can live on beyond me like BiggerPockets has done.