You Can’t Win the Game Unless You Get in the Game. How to Overcome Procrastination and Fear on the Path to Buying Investment Real Estate

You Can’t Win the Game Unless You Get in the Game. How to Overcome Procrastination and Fear on the Path to Buying Investment Real Estate

In my two decades of investing in real estate, I’ve known so many people who wanted to buy but never, ever did.

  • Some were waiting for the market to crash (It did! From late 2006 to 2011, there were numerous opportunities yet so many people didn’t buy something because they were waiting for the market to go even lower.)
  • Some needed to know every detail about the property, from what needed to be fixed, the costs to renovate, the After Repair Value, to the projected rents. By the time they got more certainty about the property, someone else had already bought it.
  • Some wanted to wait until interest rates came down to where they once were. Interest rates for investors – investors! – were at 3.5% or less in 2020 and even 2021, yet many people didn’t go buy something. Why? They were waiting for interest rates to go even lower!
  • Some wanted to wait until they had attended more seminars, built a bigger network of people in the industry, and read more books on real estate. They were preparing to prepare to learn about preparing to invest.
  • Some wanted to wait until the kids were a little older and the salary a little higher. Yet prices and rents continued to appreciate, outpacing their wage growth.
  • Some said that before they buy, they wanted to start off as a wholesaler. They said that after they made tens of thousands of dollars in wholesaling fees, then they would graduate to flipping houses. They said that after they made hundreds of thousands in flipping profits, then they would graduate to owning rental properties. Unfortunately, they never made any money in wholesaling. Buying a property with little to no money down is actually simpler (not easy, but simpler) than many people think. They could have started off by buying a property and not bothered with the wholesaling.
  • Some wanted to find the absolute perfect deal in the completely perfect location at just the right time. They wanted to hit a grand slam home run on their first at-bat.

You can’t win the game unless you get in the game. When you decide to buy a property that isn’t perfect, you learn. You make mistakes and learn lots from those mistakes. You develop skills. You build a deeper and better network of people who can help you. You learn about depreciation and saving on taxes. You learn business skills. You become a better negotiator. Each deal you do teaches you so much. With some deals, the lessons you learn are worth MORE than the profit you make. People who play the long game make more money and build more wealth than those looking for a quick deal.

If you know you want to invest in real estate, then figure out how to do it and who to do it with. It’s okay to make lots of little mistakes. With the right team around you, you probably won’t make any big, costly mistakes. Get your financing together, find the right Realtor, and go shopping. Make offers. Be decisive. Rely upon a home inspector’s report and a general contractor’s opinion.

Get out of your own way. See this as a lifelong journey, not a one-time trip. My business school classmate Elon Musk talked about accelerating your rate of mistakes to accelerate your rate of learning. You want to increase your rate of making mistakes so you become an expert at finding, negotiating, and managing deals. Successful people make more mistakes than unsuccessful people, and then successful people apply their newfound knowledge. Unsuccessful people seek to stay within their comfort zone, yet success lies just outside of your comfort zone.

If you aren’t good at renovating, then hire contractors. You’ll figure out quick who is reliable and who you should never use again. If you feel that tenants may give you headaches, hire a professional property manager.

Right now in your town, someone younger and more ambitious than you is buying properties. They are collecting rents, enjoying price appreciation, and utilizing multiple tax advantages. They are increasing their passive income every year. They took the risks and are enjoying the rewards. I know many people with little to no formal education who own dozens, even hundreds, of investment properties. They are their own boss, and they live life on their own terms.

Bet on yourself instead of betting against yourself. Everything you’ve learned in your life has led you to this very moment, and you’re worth betting on. Feel the fear and do it anyway. I’m not saying to be reckless and just buy anything at any price; I’m telling you to do just enough research, networking, and financial preparation to move forward. Be decisive. Once a decision is made, you’ll feel a sense of peace. Then get to work. You have profits to make.

In 10 years, your future self will thank you for buying today.

Tai DeSa is a graduate of The Wharton School of the University of Pennsylvania.  He became a full-time real estate investor in 2004 after serving in the U.S. Navy.  Tai made colossal mistakes in investing (and learned some things along the way).  He has helped hundreds of homeowners avoid foreclosure through successful short sales. Check out Tai’s books on Tai may be available for coaching and speaking engagements on a variety of real estate topics.  Send an email to

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