Newbies: You NEED to Overcome Your Fear of Asking Questions (& Looking Dumb). Here’s Why.

3 min read
Marcus Maloney

Marcus Maloney is a value investor and portfolio holder of residential and commercial units. Marcus has been named the “Equity King” for his impressive ability to find real estate opportunities with massive amounts of equity.

Marcus, a high school dropout, went from G.E.D. to M.B.A. Although his education has a major impact on his investment philosophy, the real impact came from his upbringing.

Marcus thrives on completing successful transactions. As a young kid, his parents and grandparents faced many challenges; as a result, it made him think of ways he could help. His mother and grandmother were avid investors—not in the market but in people. Marcus was a recipient of those investments. And his early years were hard work growing up on a farm.

Marcus was a strategist at an early age. To relieve the burden of his family buying him clothes when it was time to return to school, he decided to make a small investment that paid big dividends. Marcus decided to purchase a small piglet at the beginning of summer, feed it until it became fat, and then sell it to a local farmers’ auction before the school year started. This was one of his first transactions and the beginning of his adventure of finding equity in every opportunity.

Marcus’ hard work continues today: He has completed over $3.3 million in wholesale transactions. Currently, Marcus is a licensed agent who wholesales virtually in multiple states while building his investment portfolio. Although wholesaling provides great money, he saw the opportunity to buy some of the deals he found and convert them into cash flowing rentals.

Marcus currently holds seven rentals, two of which are commercial units. He’s also done the unimaginable and purchased a school, which was converted to a daycare center. Again, he turns what is a marginal profit into a significant equity position. He leverages the equity by using the BRRRR (Buy, Rehab, Rent, Refinance, Repeat) strategy to increase his portfolio without any money out of pocket.

Marcus has been featured on numerous podcasts, such as the Louisville Gal Podcast, the Best Real Estate Investing Advice Ever podcast, FlippingJunkie, and many others. He’s currently a featured blogger for BiggerPockets, the largest community of real estate investors in the world.

Along with completing transactions and working to build his portfolio, he provides mentorship to aspiring investors. This is done through one-on-one interactions and through his successful YouTube channel and blog.

Marcus does utilize his M.B.A. for more than real estate. As a consultant for a successful non-profit institution south of Chicago, he uses his expertise in the development of human capital. His philanthropic efforts help existing stakeholders develop in their capacity to serve those in need of assistance.

Marcus completed his M.B.A. in 2011 from Olivet Nazarene University.


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I often write articles to appeal to the newbie investor. I do this because it is important that we continue to inspire those who have the ambition to face all their fears and persevere. I remember the many challenges I faced and hearing the stories of others who were willing to defy the external and internal odds to see their desires materialize. There are many challenges newbies encounter, such as financial constraints, lack of guidance and information overload. There is one thing that I noticed along my journey and which others stated was difficult to overcome. It was the fear of asking TOUGH questions.

For some this may not be a challenge at all, but for others understanding the importance of asking tough questions is essential.

Have you ever engaged in a conversation with your peers and someone makes a statement and it seems as though you’re the only one who does not understand or has limited knowledge of the subject matter? Sure you have, but what did you do? Most people will remain silent and try and figure it out along the way and be fearful to ask a question. I’m sure this has happened to you, but the truth is that those who are afraid to ask tough questions miss a great opportunity to learn.

Related: Newbies: These 3 Simple Steps Will Prepare You For Your First Deal

You may be asking, “Ok, what does this have to do with investing?” A lot!

Overcoming the Fear of Asking Tough Questions

Here are a few reasons you may be afraid to ask tough questions and what you are missing by letting this fear overwhelm you.

It is human nature to be non-confrontational. Because of this innate trait, we are limited in our opportunities to grasp a deeper understanding from those who we are doing business with.

Here is a real estate example: When speaking with sellers, most sellers have the demeanor of being confrontational (if you haven’t run into this, you’re obviously not speaking to enough sellers), and because of this demeanor, your natural instinct is to assume they don’t want to sell and they are tire kickers — and you think, let’s just get through the call. Due to your perception of the seller, you limit your conversation to a minimum and you do not ask the tough question. By not being consistent and asking all the tough questions, you miss an opportunity to get to the real reason why the seller is calling. I do understand some sellers just call to cuss you out, but if they are willing to engage you in a civil conversation, try and learn from them.

One of the hardest questions for me when speaking to a seller was asking them, “How much do you owe on your house?” In the beginning that seemed a little intrusive. Who would tell someone they don’t know what they owe? To answer your question, the majority of the sellers do not mind giving that information. It all depends on how you frame the question.

How about this approach? “Mr. Seller, do you have any liens or mortgages on the property? If so, are you current on your mortgage? If you don’t mind me asking, what do you owe on the property because I’m aware that the values of the property in that area fluctuate, and I want to make sure we are not going to have any issue with giving you the correct value or a fair offer.” A totally different approach, but you will still get the same result.

The Importance of Asking Questions as a Newbie

Another reason it maybe difficult for some to ask tough questions is because there is a fear of being judged or feeling you are in a place of vulnerability. Yes, that’s right. If you are a newbie and you are in a room full of seasoned investors, this can be a little intimidating.

I was talking with a new investor and he was stating that he has nothing to offer to the group, and he did not want the other investors to feel as though they were wasting their time working with him.

In a situation like this, it is important to ask as many questions as possible. Do not let the fear of being judged by others limit your possibility to learn from those who are willing to teach. I’ve read a ton of leadership books and one recurring quote that I’ve read in many different books that helped me tremendously is,“If you are always the smartest person in your group, you need a new group.” You cannot learn if you are always teaching.

Related: Everything Newbies Should Know BEFORE Seeking Out a Real Estate Mentor

Asking tough questions can help you greatly. By asking tough questions, you minimize your mistakes, you save money because you minimize those mistakes, and you can travel along your journey a lot faster.

Challenge yourself by asking tough questions to the following people: contractors, agents, sellers, buyers, brokers, accountants and escrow officers.

Try this and see what you learn. Just as with making an offer on a property, you never know what you may get if you don’t ask.

What are the most valuable questions to ask when you’re learning real estate?

Weigh in with a comment!