If I Started My Real Estate Business Again Today, THIS is What I’d Change

by | BiggerPockets.com

As the saying goes, hindsight is always 20/20. I would modify that to: Hindsight is 20/20 if you learn lessons from your past and implement them into your present and future. It’s one thing to look back and critically assess what you have done, but it’s another step to move past feelings or ideas you perceive. The subjective statement “I did _____ [well/not well]” doesn’t paint the picture, the facts, or the result. Did you start with clearly stated goals in the beginning? Did you hold yourself and your team accountable to those goals? And did you make adjustments based on the data?

This morning, I found myself contemplating the question, “If I started over today, what would I do differently in my business?”

Just to be clear, I am not someone who advocates the “woulda-shoulda-coulda” mindset. But learning from our past and from others requires us to review it, understand it, and then grow and execute from it.

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My Biggest Successes & Mistakes Thus Far

  • My Positives  
    • Built an eight-figure business that fix and flips 150+ houses a year
    • Helped hundreds of turnkey clients all over the United States and internationally build wealth and freedom through real estate
    • Creating rental portfolio north of 100 houses
    • Built a retail real estate team this year on pace to sell over $20M in gross sales our first year of business and a target of $100M in sales in five years
  • My Negatives
    • Lost $50k in just ONE real estate deal
    • Blew it a dozen plus times on hiring key staff
    • Made the same training and process (or lack thereof) mistakes with staff over and over
    • Went over budget on construction projects—with one last year $30k+ over budget
    • Haven’t given clear direction or had systems to produce a consistent construction project or give the construction team the tools they needed
    • Consistently (to this day) underestimate what kind of time, training, attention, and care every single new and seasoned staff person requires

Related: The 3 Dumbest Mistakes Buy & Hold Real Estate Investors Make

6 Questions That Could’ve Helped Mitigate My Mistakes

  1. Do I have clear yearly, three-year, and five-year goals?
  2. Where am I relative to my goals?
  3. Do I have mentors in my life helping, pushing, and guiding me in all areas of my business life?
  4. Do I understand what success looks like within my business?
  5. Am I leading my team, helping them achieve both their personal goals as well as my own?
  6. Do I have the right people on my team, and have I set clear expectations for them, trained them, held them accountable, and given them autonomy to grow and execute in their positions?

Mentoring & Education

One major thing I would change in my real estate career would be to seek out a mentor early in my business. I could have made so many fewer mistakes in my business and probably saved myself from a lot of pain. I could have set clearer goals earlier and put many things in motion that we have now. I would have read more books and found more opportunities to speak with likeminded people.

This is not to say you need to go to a bunch of guru events or hire an expensive coach. But it does mean you should surround yourself with folks who are doing what you want to do in the future. Learn together, allow each other to make fewer mistakes, and be sure to meet at least every few months. Talk deals, problem solve, and hold each other accountable.


It’s one thing to know how to paint a wall, price out a house to buy or sell, or rent and manage a cash flow rental house. It’s another thing to have a clear system around construction, acquisitions, rate of returns, and decisions on what you should or shouldn’t be buying. I cringe when I hear new investors say, “I’m not that big. I don’t need systems like you have.”

On one hand, this is true to a point. There are different problems that come up flipping 10 properties a year, as opposed to flipping 40, 80, 50, or 600 a year. But that doesn’t mean that having systems in place is any less important.

In some cases, not having systems with a small business could be even more catastrophic. Say you don’t have clear buying criteria, and you buy a flip that loses money. In our business, we can absorb a loss on one deal because we might have 10-15 others closing that are profitable. It would be much harder for a new investor to do so. Plus, effective systems help you hone in on what works and what doesn’t so you can constantly improve how your business runs.

Related: What I’ve Learned (Good and Bad) From the Various Mentors of My Career

Team Members

This has been a massive, painful learning curve. There is an awesome book called The E Myth: Why Most Businesses Don’t Work and What to Do About It by Michael Gerber. I you have a real estate business—or really any business, for that matter—you need to read this book.

In the book, Michael talks about that point an entrepreneur can’t do it themselves anymore, so they make their first hire. This is all well and good, except have you created a plan for this hire? Do you have a job description? Is there training to teach them your way of doing things?

One piece I neglected for quite a while was the culture within the organization. Do you understand what you want your business to be? How do you go from just you to a team, a business partner, a full staff with layers within an org chart?

This can be a huge source of constant pain. As business owners, it’s time for us to stop hiring folks without a clear plan. We need a strategy for every step of the hiring and on boarding process before the person is hired. We have to be clear on their goals and our expectations for that new team member. We need to provide them the training, the feedback, the accountability, and the space they need to succeed in that spot.



I’ll tell you this. CEO sits behind my name—and it means absolutely nothing (at least by itself).

What we have learned in our organization is that leadership is not given. It’s earned, learned, and taken over time. It comes with experience and clarity on how your business runs.

Only when you’ve completed the following can you truly be an effective leader within your company:

  • You’ve mentored with likeminded people, read everything you can get your hands on, and learned about yourself and your business.
  • You have clarity on your goals—your why.
  • You’ve laid out systems and structure on how to do the things you do in your business.
  • You’ve created a road map on how you train within those systems, and you refine them over time.
  • You’ve hired staff who are the right cultural, positional, skill, and talent fits for their positions.
  • You constantly talk about, train on, refine, and hold yourself and your team accountable for the tasks and systems around those tasks that you as a business are responsible for.
  • You don’t promote yourself or any other team members without first being sure of ability to be accountable.

Final Thoughts

If you take away one thing from this post, I hope it’s to reflect on what you are doing in your own business. If you are brand new, what do you want it to look like? If you are on your first few flips, wholesales, or rentals, do you have clarity on basic systems and structure in your business? And if you have a larger organization or are doing 20-30+ deals a year, where are you within the spectrum of the business structure? Do you have clear processes, targets, and a team that understands those goals? Are they held accountable? It’s time we take the next step in our positions as leaders, and use those skills, talents, and dreams to build incredible businesses doing amazing things.

Where are you on your journey of building the business of YOUR dreams? Where are you stuck, learning, growing, or in need of help?

Weigh in below!

About Author

Nathan Brooks

Nathan Brooks is the co-founder and CEO of Bridge Turnkey Investments, a Kansas City-based company renovating and selling more than 100 turnkey properties per year. With over a decade of experience in real estate, Nathan is a seasoned investor with a large personal portfolio and a growing business portfolio. Just last year, through Bridge Turnkey Investments, he helped investors add over $12 million in value to their real estate portfolios. Nathan regularly produces educational content to fuel his passion for helping other people learn about and find success in real estate investing. He has been featured regularly on industry podcasts such as the BiggerPockets Podcast, Active Duty Passive Income Podcast, Freedom Real Estate Investing Podcast, Fearless Pursuit of Freedom Podcast, Titanium Vault, The Real Estate Investing Podcast, The Best Real Estate Investing Advice Ever Show, the Good Success Podcast, FlipNerd, Wholesaling Inc., The Real Estate Investing Profits Master Series, Flipping Junkie Podcast, Flip Empire podcast, Think Realty Radio, and more. He is a sought-after speaker and writer and can be found on stage regularly at events across the country.


  1. Barry H.

    Excellent recap on key items, especially 1 3 5 year plans. I too lost $35K on a $150K flip investment (my very first) and will now probably never flip again.

    You have nailed what I perceive to be perhaps the most critical variable to success, the investment in other people. After 15 years in RE investing, even with some mentoring, I cannot find team members who are invested in success, especially in a market outside your hometown.

    Based on your article, I will give more consideration to pre-vetting potential team members on future projects.

  2. Rob Cook


    Good article. I think one issue many of us face, is that we are often entrepreneurs, not managers. That was my case in our $7 Mill a year residential remodeling firm. Very different skill sets and even personality types often. So recognizing this potential divergence is important, and stepping aside and hiring managers is a good move.

    As for construction management, we struggled for 20 years to try to get a grip on this, and never have. I chose to make 3 times as much money, working in chaos, as opposed to making 1/3 as much and being well run! It worked, and I am talking about a difference of anbout $600K a year net. We did the same volume with 7 office staff, that competitor firms did with 22 office staff. And trying to manage field employees is a never ending mess. If they are good enough to really act as “Lead capenters” they they cannot be managed closely or you will run them off. And without $20K of detailed plans per job, they have to managed closely! Again, systems, but all those costs have to be weighed against what your planned outcome is. Mine was making the most money with the least headaches. Since we could pull it off, due to our own personal dilligence, we never learned to really back off and “Manage” properly. Instead, we were able to do 3 peoples work each and keep the additional money. Stressful? Yes. But trying to make a lot of money with a huge staff would have driven me out of the business.

    So we pick our poisons. This same type of small thinking carried over into my RE investing, and again, I have made a lot as a result, albeit working a lot too. And I probably have limited my potential long term as a result. So what. I am 59 and still at it! And now without any employees to deal with. Well, one now, a young laborer working on my rehabs so I can take it easy most of the time.

    • Nathan Brooks

      Rob – I really do agree, its what kind of problems do you want, and what kind of problems are you willing to solve. Construction management is a BEAST!!! And it takes a special kind of person with a special skill set to do this very well.

      I know for me, I’ve learned I can’t do it all on my own because I’m just not that good at the daily activities of management and the real in-detail issues that come up during the given work day or project. Instead, I can use the leverage of building processes and asking questions to build those systems and instead find awesome, highly skilled, and culturally right, to get after it with us. Good luck!

  3. Jerry W.

    Thank you for writing this article. It really hits home. I am only at the 30 rental stage, but need to set up systems. Do you have a system, or book you recommend? I have read EMyth. I am also interested in getting into a good support group or accountability group. Let me know if you have any recommendations please.

    • Nathan Brooks

      Jerry – Thanks so much for your words here sir. 30 is a great number, and nothing to be ashamed of. I’d suggest first asking that question “what does it look like when it’s done?” Are you going to use a property manager? Are you self-managing, do you need someone on your team for tenant relations or maintenance?

      Support group wise I’d suggest you post on the forums here at BP and get several folks at the similar level of rentals, and problems … you guys can bounce ideas off each other and grow together in that way. Do a call once a month or so. Also check out the book Traction, it’s been a huge help to us. Thanks Jerry! Best of luck sir … I know you will get after it.

  4. Robert Antonie


    I appreciate your article. You mentioned that you have struggled with finding the right people for your team. I suggest you read the book, “The Ideal Team Player”, by Patrick Lencioni. He defines what the perfect person is, Humble, Hungry and Smart (People Smart). The book should be well worth your time. I wish you continued success!

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