The Monday Morning Quarterback: 8 Things I Would’ve Done Differently in Real Estate


Superbowl XLIX is history, and hats off to the New England Patriots. A pretty good game overall, one the Seahawks seemed to have wrapped up. Why Seattle would elect to run a pass play for the lead on second down mere feet from the end zone with 20 seconds left will be discussed and debated around water coolers, in break rooms and just about everywhere else today. We will all become Monday Morning Quarterbacks. We all love to analyze what could have happened if Seattle had just run the ball or if pass interference perhaps should have been called. It’s fun to play the role of the Monday Morning Quarterback.

Hindsight is, of course, 20/20. It is always easier to examine something, be it a football game or our own real estate career, after the passage of time. Looking back is not just fun, is in fact something that I think should be done. We have to look back and reflect upon what should have been done, or what would have happened if we had only done A instead of B. It is how we learn. It is how we process information so we can make better decisions going forward. So looking back on my own real estate career, what are some of the things I wish I had done differently?

Well, there are lots of things actually, but here is a short list I jotted down to perhaps save you the trouble I had.

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8 Things I Would’ve Done Differently in Real Estate

I Should Have Bought That Property

There have been several properties in the the past that were available, and for whatever reason I did not acquire. Today I drive by some of those properties and kick myself for not buying them. What was I thinking at the time? Did I not see what a great deal that was or the income potential? Did I not have my funding in place? Was my head wrapped around some other project? Likely, it was a bit of all of the above. I should have been more focused on my business and had my ducks in a row for when deals came along.

I Should Have Expanded My Horizons

When I started out, I was very focused on being a landlord. I bought properties to hold in certain areas and that was all I did. How much income did I pass up because a particular property did not fit these criteria? My field of vision was too narrow to see opportunities. Today, even if a property does not meet my particular criteria, I might try to do a wholesale deal or a retail flip. Those things are no longer something that I do not do.

I Should Not Have Borrowed As Much

Don’t get me wrong. I am a firm believer of using other people’s money. But I also think Dave Ramsey makes some sense, too. I would certainly love to have more properties completely paid for. It is just gives me peace of mind to know a property is truly all mine.

Related: Three Business Lessons Learned From the Seahawks’ Super Bowl Defeat

I Should Have Kept More Reserves

Reserves also give you peace of mind. It is comforting to know that there is a chunk of money sitting there in case I need it. And there have been times I have needed it. Things happen. Sewer lines collapse, air conditioners give out, roofs leak, fires break out, property taxes come due and it seems like it all hits at once. If you want to survive in this business, you will need reserves. How much? Whatever you are thinking, you should double it.

I Should’ve Developed Better Systems

Effective systems are one of the keys to any successful business. It took us a while to realize this. For the first few years, we kind of flew by the seats of our pants. And honestly, it worked for the most part. But I wonder how much better things would have been if we had some systems in place. How much money flew out the window because we did not? Plenty, I imagine. There is no process that is too small or insignificant to have a system. Plus, if you really want to extricate yourself from the day to day operations in the future, systems are the way to go. This is something we still work on to this day.

I Thought I Could Do It All

I used to think I could do it all. I could handle all the repairs and maintenance. I could do the paperwork. I could do the taxes. Plus, I thought I was saving money by not paying other people to do these things. But I was not saving money. I was losing money because I did not have the time to develop my business (see “I Should Have Bought That Property”). You will make more money by spending money to hire others to help you. That was a hard one for me personally to learn.

Related: 3 Real Estate Investing Lessons I Wish I Had Learned Earlier

I Shouldn’t Have Lowered My Standards

Every time I did, it always turned out badly. Whenever I had an apartment sitting on the market for a while and lowered my standards to get it rented, I wished I had not. The apartment always ended up trashed or occupied by a non-paying tenant and ended up costing much more in the end. Whenever I went with the cheapest guy, again I wished I had not, as the job often had to done over again the right way. Don’t lower your standards.

I Should Have Started Sooner

This is one that really gets me. I really wish I had started in real estate sooner. Where would I be today if I had started 10 or even 5 years earlier? Why did my younger self not listen to people? I have no answer. I guess I just have to blame it on youth.

So what about you? What does your Monday morning quarterback mindset say about your business? What would you have done differently?

Please share with your comments.

About Author

Kevin Perk

Kevin Perk is co-founder of Kevron Properties, LLC with his wife Terron and has been involved in real estate investing for 10 years. Kevin invests in and manages rental properties in Memphis, TN and is a past president and vice-president of the local REIA group, the Memphis Investors Group.


  1. Alex Craig

    1. I would have spent more on the front end. Many of my properties I used vinyl floors, cheap materials and carpet throughout, which made my rent ready cost a lot more expensive and ongoing maintenance higher. I made that coarse correction in 2011 and my properties while more expensive to get into, are providing higher cash flows.

    2. I have 5 properties that I wish I never bought and wish they would burn to the ground (of course, when they go vacant). Those $55,000 deals never work out as planned. I would have bought all B+ and A properties. Those are the ones that really make money in the long run and will not cause grey hairs.

  2. Mike S

    I can definitely say my one do over would be starting earlier in life. I did get my first rental at 30 but what if that had been 21 or 18

    My kids will have a much different education than I did concerning money.

  3. Rick Grubbs

    1. I would have developed a relationship with a local bank sooner. Having a sensible portfolio lender has paid off big time for me.
    2. I would have gotten out of property management sooner and focused more on buying good cash flow properties with creative financing. That has a very high hourly return for the time invested and can’t be delegated nearly as easily as mowing lawns.

  4. Shyreeta Cress

    Although I have yet to wholesale a single property, I still wish I would’ve started sooner. I earned a Bachelors in Finance with a Real Estate concentration back in 2009. I knew I wanted to be an investor long before then. I just thought the safest entry would be my college education. Now I feel like I wasted too many years

  5. As far as the big game day errors go I’ve said too much on Brandon’s side of this post already. So if you read it forgive me my opinion please, I might just have done the same or worse.
    On the business aspect I know I have done worse and only at this point do I start to get how the pro’s line their players up. I know a good many mistakes I have made that could have and can be avoided in the future if I can show well enough in tryouts to get on a team and play a position. Your post is great and yes I took notes and have and will in the future but being on injured (reserve) my rehab is my own responsibility. Keep writing, I’ll keep trying to read and learn.

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