What I Learned by Jumping Into Real Estate Full-Time (& Failing Miserably)


Nearly two years ago around Christmas time, I found myself working as a worship leader at a high profile church with tens of thousands of members, preparing for Advent and a total of seven Christmas services, all the while flipping seven houses at the same time. It was crazy trying to keep up with the guys on the job sites while understanding and meeting the needs of my church music team. The balance of home life and everything else was nonexistent.

Something had to give.

Although I loved my church family dearly and had spent three years growing my team of amazing musicians, I was feeling an incredible pull to step out of my role at the church and to dive back into my real estate business. The fog of the ’08/’09/’10 years was still very present in my mind, and the colossal meltdown and failure of our personal real estate business into bankruptcy and a complete financial failure and restart were constantly on my mind. We basically lost everything, and it was awful.

I knew what it was like to jump off the cliff, experience some success, and then fall completely and utterly on my face.

Fast forward nearly a decade through some small-time real estate investing. The past two years have been a combination of difficult learning, constant personal growth, incredible successes, massive wealth-building opportunities, pain, suffering, and incredible joy and pleasure. Looking at our business from the early 2000s to what it is now, there have been many significant experiences that have helped me grow — and a few that have made the most impact on me, both positive and negative.

A hinge point here has surrounded around not thinking as an individual but a business. We’ve come up with a series of systems and implemented them for our team. It’s very easy to do a few rental houses and a couple flips a year. It’s a total different animal to have 25+ active job sites at one time, a growing staff, a business partner, and a budding operation in transaction from small business (owner run) to a real business that operates with sophistication, operations, and systems. I can easily tell you with no pause that growing a business is the hardest thing I’ve ever done in my life. And I wouldn’t change it for anything.


Fail in a Massive Way

If you are going to screw up something, do it in a big way. Don’t be afraid; either way, it’s going to happen. I can attest. You will definitely screw up more than once. You will. Your partner will. Your team will.

This year, I’ve made mistakes big and small in every arena from running a team, hiring, and construction to operations and systems. You name it, we have completely blown it more times this past year than I can countd Like Ricky Bobby’s Dad says in one of my all-time favorite movies, Talladega Nights, “If you ain’t first, you’re last.”

I love to win. I love to be right. But you can’t win all the time. And just like Ricky, sometimes you crash and burn, but still have to get back out on the race track.

Related: How to Fail 90% of the Time and Still Be a Wildly Successful Real Estate Investor

Get Up and Grow Up

I easily have read 20+ books this year, from Tim Ferriss’ The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich to Jocko Willink and Leif Babin’s Extreme Ownership: How U.S. Navy SEALs Lead and Win, and just this past week, Rocket Fuel: The One Essential Combination That Will Get You More of What You Want from Your Business by Gino Wickman and Mark C. Winters. If you are already running a business and have at least a few staff people, and you haven’t read Rocket Fuel, go get it. That’s my current life, business, and game changer.

Here is the point: No one is going to teach you like you learning yourself. Let me make this point clear, though. That doesn’t mean you don’t need a whole team around you. You need a coach or a mentor, as well as contractors, attorneys, a great CPA, and a colleague or two who understands where you are, where you’ve been, and where you are going.

Growing up is hard — much harder as you start to realize what you don’t know. When you don’t know something, you are vulnerable. You may be scared — or perhaps the opposite. Instead, might run through whatever brick wall or tall tower it takes, sometimes discovering it wasn’t the right wall or tower in the first place. I know because I’m wired that way.

This yea,r I’ve made more money in a month than I made in a year just a few years ago. I’ve lost more money in two real estate deals this year than the first two years out of college. Our team has made more hiring mistakes than I’d like to think about. We’ve had construction failures, team failures, and personal failures. I have failed my partner and my team. It happens. We all screw up. Get up. Dust yourself off and get back after it.

As a new friend out of the East coast said at a recent real estate mastermind, “This isn’t practice.” It certainly isn’t. This is real life.


Who Will Influence and Mentor You?

I can’t speak enough on having a mentor. In the early years of my real estate investing (now more than 10 years ago), there were a number of guys I sought out, harassed, begged, or took to lunch — whatever I could do to pick their brains and ask the best questions I could muster. You don’t know what you don’t know. Some of the most important conversations were not about money. They were about systems, people, and processes.

Find someone who you connect with, who has similar interests in real estate, and learn with them.

Personally, I have a small group of people I trust and reach out to for specific things I need. I desire to grow as a leader in my business. I’m learning how my partner and I work together, how his skills are different than mine, and how we can both use our skills and talents to the very highest and best use. Just a week or so ago, I had the pleasure of attending a mastermind with some of the biggest and most sophisticated investors on the planet in the single family space, and we talked openly about our businesses — things that are working, things that aren’t.

No matter where you are, who you are, and what you are doing, there is someone out there you can learn from. Don’t be afraid to learn. Seek it out and make it a daily practice.

Learn About Your Strengths and Weaknesses — and Exploit Them

While reading the latest book in my library, Rocket Fuel, my partner and I both had an epiphany within our business. We took a face to face look at our personalities and skill sets within our business as laid out in the book, and then we took some operational direction to implement action and roles around those personalities. If you can’t understand what type of person and leader you are, how could you possibly succeed long term? I know there are a lot of businesses out there with owners who don’t think about this, but I’m also aware of a lot of unhappy employees stuck within a business where they are tied to the whim of the owner’s actions, misunderstandings, and poor leadership.

One of the massive takeaways from the book has been defining the roll of the visionary and that of the integrator. It happens that I got very lucky in my partnership, as we have wonderful communication, diverse skills, and we just happened to be a duo of both a visionary (me) and an integrator (him). The visionary has the big picture ideas, but is not good in the details. The integrator in this instance is also good with the big picture ideas, but has a real gift for implementing systems and running the day to day management of those. I am not good at that role at all. I’ve often wondered why I got so frustrated with employees who weren’t doing what I wanted, and now realizing for more than a decade, it had been my fault the whole time.

I didn’t know how to integrate my ideas into actionable steps and processes to follow. It’s easy when it’s the one man show. It’s a whole different thing when you ask someone else who wants concrete steps, a process, and a clear path to get there before they do it. Boy, have I blown it so many times! And now, what a massive opportunity to — you guessed it — fail, get up, and learn.


Related: 5 Ways Failure Can Help You (Not Hurt You) While Cash Flow Investing

Be a Leader and Own Your Space

If you aren’t leading your business, someone or something else is.  If you don’t think for a second that is your responsibility, you are wrong. You have to lead. People need to know where they belong. They need to understand their role. Your staff wants confidence in what they are doing, in the people they work with, and in the community and values of your business. Take the time to listen to your people as you grow your business. They are there to help you. Make ideas and roles within your business clear, and understand what you are there to do and why.

At the recent mastermind, Darren C., an incredibly successful and personally motivating speaker, used the line with his people, “Own your space.” I love that. It makes perfect sense. And in order to own your space, you have to know what to do! Have a set of guiding principals and steps to follow, and then have clear benchmarks on how to operate and measure. Lead your team, show them where you are going, understand the steps to get them, and let them go get it.

Final Thoughts

Owning my own business is one of the most wonderful and rewarding things I’ve ever done. It’s also been one of the hardest. Don’t take the opportunity lightly. Prepare mentally, financially, and emotionally that everything will not come together immediately. Have a great team of people around you. Understand who you are and where you should fit on your team. Build the team around key leaders as they come into your business. Don’t be afraid to fail — embrace it. Decide the outcome now, and visualize it and write it down. Have a massive “why” beyond money. And go get it.

If you jumped into real estate full-time, what has the experience been like? What have you learned?

Let me know with a comment!

About Author

Nathan Brooks

Nathan Brooks is a dad, husband, worship leader, and real estate investor in the Kansas City market. Foodie. Coffee addict. Crossfit junkie.


  1. Randy Evanchyk

    “We should not look back unless it is to derive useful lessons from past errors, and for the purpose of profiting by dearly bought experience,” I love this quote by George Washington!

    As they say, mistakes are not the problem. Not learning from them is.

    • Nathan Brooks

      Hi Desiree … I believe it does as well. The failure leads to learning, which leads to wisdom. I think it’s profound and necessary to have the failures to work through problems, understand how obstacles become lessons/learning opportunities … and then breakthroughs from them.

  2. Nancy Emineth

    This article was informative and helpful. I appreciated your wisdom and honesty. Throughout my journey it has been a lesson in not only skill, ability, and willingness to fail. You are 100% right “the path will be difficult but the end results will be worth it.” Thanks it was a good read.
    From Nancy

  3. Derrick Atkinson

    Hello Nathan, great article, I actually stepped out on faith to go full time in REI 2 years ago, and I can truly identify with learning from mistakes, it feels like I’m making one once a week but what I try to do is document the lesson learned. I have grown my portfolio since the start of my business but my biggest challenge also is finding a mentor and learning how to automate my business, I believe once I find the right mentor, process, and reliable team my business will soar undoubtedly.

    • Nathan Brooks

      Derrick … its faith, its belief in yourself, and then its taking massive action. We believe, and turn that belief into our internal dialogue and even in the hardest or most difficult times, we get after it. You will find that right mentor and you will continue to grow, learn, and get processes in place for your business. It’s so important no matter where you are to have those guys who have been there to help you through. Best of luck my brother, you will get it.

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