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Posted about 7 years ago

How to “Sell Your Face Off” as a Real Estate Entrepreneur

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As real estate investors, we are entrepreneurs – we are creating the same thing that the typical entrepreneur create, which are businesses; therefore we are entrepreneurs. Kolby Kay, who has built, sold, and advised over 20 startups that have generated over 50 million dollars in revenue, has a lot of successful entrepreneurial experience in many different industries. In our recent conversation, he provided insider insights on how to successfully target, identify, and understand your audience.

How to Approach Uncovering and Fulfilling a Need

Kolby finds that there are two main aspects to approaching customers. First, you need to put yourself in their shoes. After you’ve done that, you need to understand what their pain point is.

Kolby says, “you need to be putting yourself in the shoes of somebody who is your customer and understand what it is their pain points are and not selling by features, because that is what sales people do. They try to talk about ‘look at my widget. Look at how great my stuff is.’ But people don’t care.”

What do they care about? The are about “what problem are you solving for me today and then do you have social validation that you’ve done it with somebody who looks and acts and feels like me? In other words, it’s all based on a need and somebody fulfilling that need.

Kolby breaks it down further into a four distinct pillars that he follows for all of his business deals:

  • “The first is identifying a group of people with a problem or a need”
  • “Second piece is coming up with creative way to solve that problem, whether that’s a product or service”
  • “The third piece is validation
  • “The last pillar is what I call ‘sell your face off.’

Kolby finds that a lot of people skip pillar three: validation. “This is the piece that many young entrepreneurs or even seasoned entrepreneurs will forget. Just because you found somebody that will buy something and you think you’ve found a problem, have you done due diligence on validation? Meaning, you’ve gone back to that group of people that you’ve identified that have a problem that you can supposedly solve and ask them: [does this] specific widget or software or service solve your specific problem AND are you willing to actually pay for this specific solution? That last piece of ‘is it something you’ll pay for?’ is very very important.”

How to Sell Your Face Off

When Kolby “sells his face off,” this is when he puts himself in the shoes of the person he’s trying to sell to and attempts to uncover what’s most important to them. This means asking questions instead of talking about what it is he does. The most important question that Kolby asks is, “What are the problems you are facing?” After leading with that question, examples of other questions would be:

  • What’s keeping you up at night?
  • What are you doing today?
  • Why are you doing it the way you are doing it today?
  • What would you change?
  • What would you keep?”

By asking about their problems and needs, it will allow you to gather enough information and get a feeling of what’s important to them so that you can turn it around and position/sell yourself.

When positioning yourself, Kolby recommends that you “touch on the points that they said were important to them vs. telling people how great [you are at approaching the] problem that you’re trying to solve. Taking a look from the side of the customer and positioning the problems your solving in their vernacular is key.” In other words, Kolby likes to follow the Art of Selling, which is “listen, ask questions, and then…regurgitate what the client is telling you vs. telling them how great you think you are.”

Kolby provided an example dialogue that a real estate investor or agent would have with a customer after identifying their needs: “What you told me was important was having a property that was in an up-and-coming development, that had not just amenities, but there was other developments that were happening. [Well, in this area,] you have a mini-mall happening. You have a school that’s happening. You [also] told me that schools were important based on the investment property you’re coming into. Let’s talk about that. How many kids do you have? What types of schools do they go to? Why is that important?”

As you can see from Kolby’s reply, he responded directly to what the customer stated as important, rather than babbling on about himself or things the customer wasn’t interested in.


When we are thinking about how to approach our audience or client audience, we need to put ourselves in their shoes and understand what their pain points are, rather than selling them a feature. People don’t care about features. They care about what problem you are solving for them today, as well as what social validation you’ve gotten from other clients that look, act, and feel like them. It is all needs based.

More specifically, Kolby has a 4-step approach to uncovering and fulfilling client’s needs:

  • 1.Identifying a group of people with a problem or need
  • 2.Coming up with a creative solution to solve that problem or need
  • 3.Providing validation
  • 4.Selling Your Face Off

When you are “selling your face off,” you must put yourself in the customer’s shoes and ask a ton of questions. In doing so, you will gather enough information to uncover what’s truly important to them so that you can turn it around and position (or sell) yourself using their language. In other words, you are following the art of selling, which is listening, asking questions, and regurgitating what the client is selling you.