Real Estate Investing Basics

How to Overcome the 10 Biggest Obstacles Between You & Your First Deal

Expertise: Commercial Real Estate, Personal Finance, Real Estate Marketing, Business Management, Landlording & Rental Properties, Real Estate Investing Basics, Personal Development, Real Estate News & Commentary, Mortgages & Creative Financing
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What really stops first time investors from getting started? How do you get past those hurdles and limiting beliefs?

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In my previous article, I revealed the 10 reasons investors say they are held back from getting started. Now let’s look at 3 solutions to each excuse, so that you can get started on your way to that first deal.

How to Overcome the 10 Biggest Obstacles Between You & Your First Deal

1. Time it Takes to Get Paid

  1. Invest in rentals that are already throwing off cash flow.
  2. Wholesale properties.
  3. Begin part-time while keeping your day job.

2. Family

  1. If your family doesn’t support you, find a group of people who do (via a local real estate club, BiggerPockets, etc.).
  2. If your spouse doesn’t support you, practice some “togetherness” exercises surrounding real estate, and explain to them how you plan to invest wisely, showing them numbers, spreadsheets, etc. to give them more confidence.
  3. Let the results speak for themselves.

Related: Blogger Roundup: 21 Reasons Newbies Struggle to Close Their First Deal (& How to Overcome Them!)

3. Funding

  1. Find investment options that fit your current available capital.
  2. Partner up with other investors (know what you bring to the table — time, money, or deals).
  3. Tap into your inner circle, i.e. family, friends, former work associates (treat their capital as if it was your own in the event you go this route).

4. Saving Up Enough

  1. Invest first, then save a percentage of your returns.
  2. Pay yourself first out of every paycheck and invest that money.
  3. Leverage your savings with financing.

5. Finding Inventory Close By

  1. Check out new, upcoming neighborhoods that others might be overlooking.
  2. Look for deals in other cities.
  3. Look for out-of-state deals.

6. Intimidated by Large Dollar Amounts

  1. Set really big money goals, and understand it takes a lot of money to get there.
  2. Practice writing really huge checks to yourself.
  3. Choose non-recourse debt or syndications so that you aren’t taking on big loans on your personal credit.

Related: Newbies: You Should Focus on Your First Deal And Nothing Else. Here’s Why.

7. High Property Costs

  1. Go to markets with properties for sale that are more affordable.
  2. Invest with partners.
  3. Search for discounted distressed real estate.

8. Marketing Budget

  1. Use Craigslist or handwritten letters (when I first started out, I wrote all my letters by hand until I had more funds).
  2. Pick up the phone and call. Pull public records to find landlords that owns multiple properties, then give them a call. I use You’ll be surprised to find that most people still have landlines (Baby Boomers especially).
  3. Door knocking costs nothing but your time.

9. Having to Create a Team

  1. Lunch with a pro in every real estate segment next week.
  2. Choose a turnkey investment with a team in place.
  3. Run free job ads on Craigslist, Upwork, and Fiverr.

10. Yourself

Above are three solutions for each excuse for not getting started in real estate. They are all here served up on a silver platter. If you want more options, you’ll find them if you look. But the bottom line is that we each need to take extreme ownership of ourselves. If we aren’t getting what we want, it’s our own fault; no one else’s. Not the market, not your location, or the family you were born into. It’s up to you to take action.

Confucius once said, “The will to win, the desire to succeed, the urge to reach your full potential — these are the keys that will unlock the door to personal excellence.”

How are you tackling obstacles on the way to your first deal?

Let me know your story with a comment!

Sterling is an multifamily investor specializing in value-add apartments in Indianapolis and other Midwestern markets. With just under a decade of experience in the real estate industry, Sterling w...
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    Robert Ombres Real Estate Broker from Asheville, NC
    Replied over 4 years ago
    I’ve been analyzing local deals looking for ways to get started in REI. I’ve been looking into buy and hold deals. A problem I see is the investors I have in mind to help fund my deals (I’m starting with almost no saved funds) is their age and time it would take to recoup their investment, let alone profit with a buy and hold. This pertains to #3. I suppose a few ways around this (my problem) is finding younger investors who won’t mind the longer return on investment period or a more rapid returns method such as flipping. Anyway, great blog post!
    Sterling White Rental Property Investor from Indianapolis, IN
    Replied over 4 years ago
    Thank you for your input. Are you saying the individuals you have spoke to are wanting more of a short term investment i.e. providing a loan on a fix & flip deal
    Andrew Syrios Residential Real Estate Investor from Kansas City, MO
    Replied over 4 years ago
    Nice “cheat sheet” so to speak. Well done Sterling!
    Sterling White Rental Property Investor from Indianapolis, IN
    Replied over 4 years ago
    Thank you for the kind words, Andrew.
    Abner Coelho from Simi Valley, California
    Replied over 4 years ago
    Mr. White, thank you for taking the time to write this. I will refer back to this article when Im ready to dive in later this year.
    Sterling White Rental Property Investor from Indianapolis, IN
    Replied over 4 years ago
    You’re welcome. What’s stopping you from diving in now, Abner?
    Sedriah F. from Charleston, SC
    Replied over 4 years ago
    Hey, thanks for the article. I’m interested in getting started and have started reading Bigger Pockets blogs to get more information and advise before I start. One obstacle I see is finding contractors. I don’t know anyone to do the work to fix the houses I see. How do you find a good contractor? what do you look for? What do you ask? I hear horror stories on bad contractors and don’t know how to get started. Do you find all the contractors before you get started?
    Sterling White Rental Property Investor from Indianapolis, IN
    Replied over 4 years ago
    There’s multiple routes you can go to finding reliable contractors. Referrals are always good and I use Thumbtack as well. You can find very resourceful forums on here that go into detail on what to look for and questions to ask a contractor. Hope that helps.
    Sedriah F. from Charleston, SC
    Replied over 4 years ago
    Thanks, I will look for these forums. I will go to Thumbtack as well.
    Kenny Jones Real Estate Investor from Beaverton, Oregon
    Replied over 4 years ago
    Awesome read! I absolutely love saving money so it was good to see this on a few points. Feel like so many of my friends make a paycheck and then spend spend spend…mostly on restaurants and alcohol *facepalm* Thanks!