Making Your Enemies Work For You

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Early on in my real estate investing career I came across a fork in the road in which I had to decide what kind of investor I wanted to be and what kind of business I wanted to run. On one road you adopt the larger than life Donald Trump persona and muscle your way to success – knocking down others along the way. No one loves you but, instead, everyone fears you. Used skillfully, fear and aggression can be an important tool towards real estate success.

The other road is the exact opposite and entails using love and kindness as the building blocks of your business philosophy. Both methods are not mutually exclusive and you can argue that a mixture of both is needed to be successful in real estate. Both methods also have their own advantages and disadvantages and many investors have found success leaning towards one of the methods. As for me, I simply chose to follow the path that most resembled my own personality. Since then I’ve already started to reap the benefits.

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“You Can Catch More Flies with Sugar and Honey Than with Vinegar”

On one of my recent flips I had an interesting situation occur. We had just put a house under contract and was set to close three weeks later. Everything was going fine except around the last week it became clear to me that for whatever reason, one of my private lenders would not have the money available to transfer upon the closing date.

This was fine with me as the worst case scenario was that I would pay out of pocket and be reimbursed with the lender funds a few days later. But, being the investor that I am, If I can prevent coming out of pocket even for a few days then I’m all for it. So, naturally, I started inquiring with the listing agent about extending and outlined my predicament.

Her response: “NO, THE SELLER IS READY WITH DEED AND TITLE AND THEY WILL NEVER APPROVE AN EXTENSION.” Hmm, Feisty, I thought but in the end what did I expect – I was asking for something that was pretty unreasonable. After that scathing response I informed her that we were set to close on the original date, sorry for the inquiry, can’t wait to get this house started, have a nice day, thank you!

Fast forward to closing day and it was the listing agent running around frantically asking me for an extension. As it turns out, the seller was not ready with the deed and title and in fact it sounded like it would take another week before everything was set to close. Obviously the urge to rub matters into the agent’s face was extremely high and my own agent even recommended mentioning the fact that an extension was propositioned by my party a week prior. In the end, after much deliberation I decided to take the high road and simply smiled, agreed to a one week extension and opted not to bring up the past.

After the addendum was signed and sent off there was simply silence, no thank you, no response. Thankfully, the rest of the closing went off without a hitch and like clockwork we closed on the house a week later – needless to say it wasn’t the most difficult closing I’ve had but it sure was frustrating working with a less than cooperative listing agent. In my earlier investing career I would have simply left it at that and went about my way. But, as you learn a few things about real estate investing you find out that it truly is a people business. So, my next step was something I think the realtor NEVER expected.

Love Thy Enemy

Sometimes the best kicks in life are from doing something nice and unexpected for people who may not deserve it. It’s fun to sit back and see the magic that can arise from a simple gesture such as a thank you card. In this listing agent’s case we took it a step further and sent her a personalized thank you letter along with a small gift card to a local eatery. We thanked her for her help with closing on the particular house and that we hoped she had a good experience and would consider working with us again in the future.

For a while we received no response and we simply forgot about it. We send out quite a few thank you cards in an effort to try to personalize the interactions we have with everyone we come in contact with. So, to not receive a reply was not unusual for us – we just chalked it up to her being a lost cause and moved on. But, to our surprise, the listing agent called us about three weeks later and ecstatically thanked us for the “wonderful” gift card and for being “easy” to work with on the last house. We made such an impression that she even took down the type of investment properties we were looking for and promised to get back to us if anything popped up. Since then she has sent us a few pocket listings and we’ve even made a few offers through her. Although we have yet to close a deal with this particular agent, she has followed up with us on occasion and I suspect we are getting close to completing a deal sometime in the near future.

What Did I Learn?

Life is too short to burn bridges and hold grudges over petty things. Also, making it a point to be vindictive is, in the long run, never as gratifying as taking the high road and trying to befriend your enemy. From my interaction with this listing agent I was able to focus my energy on being happier as opposing to stewing in my anger and resentment. I also like to think that I was able to change her life at least in how she deals with potential clients. Since the thank you gesture, her interactions with me and my team has always been very easy going and pleasurable. She’s gone from all caps, one sentence e-mails to rapport building phone calls and even commenting on my Facebook page. When I call and request info on a particular listing or need access to a house she makes a concerned effort to meet my needs and oftentimes I’ve been prioritized in her busy schedule.

So, how have you been building your local reputation? Are you seen as the high flying Donald Trump, controversies and all, or are you the good willed real estate investor who works to build relationships by finding common ground and reaching out? There are advantages of both but let me hear your story.

Photo: FadadoFogo

About Author

Glenn is the founder of Fresh Start Homes, a real estate investment company in Hampton Roads, Va. that focuses on eco-friendly rentals and rehabs. He also owns and operates BundleBaths, an online bathroom supply store catering to real estate investors.


    • Robert,

      Funny you say that. When working with some contractors my project manager and I play a sort of good cop, bad cop type of thing. They know that if I show up at the project site, something’s not right and I’m not leaving until it is… so, if they want to do it the easy way they’re better off solving issues with my project manager because he’s much more understanding!


  1. Great post, Glenn. It’s often easier to let fear and aggression take over in tense situations, than to take the effort to stop your way of thinking in its tracks, and remember that love and generosity go a FAR longer way than getting angry and losing out on opportunities.

    This article will be a great reminder of that if / when I come into a situation like that!

  2. Melodee Lucido on

    What a beautifully written article. The way you handled this, my young friend, is why I feel you are destined for greatness. You lead from the heart and yet your pocketbook is doing well also : >

    In answer to you inquiry about what works for us: I have been called the Pollyanna investor by some of my investor buddies (I thought of putting up a blog by that name) and if it’s true then so be it. We work best when we are being ourselves.

    I have sellers regularly apologize profusely that they can’t sell me their house at “that price” and tell me that they’ve enjoyed the process tho. lol. Sometimes people call me months later after we talked and say they kept my number because I was so pleasant.

    My style is to lead from the heart.

    Thanks for the heartwarming post Glenn. Blessings to you and yours : >

    • Trevor,

      On my first flipped I fired 9/10 of the contractors I had hired (not kidding). Although at the end of the day I made a good profit and the job was done fast, I wasn’t making any friends with the locals handymen.

      Running around like a Donald Trump wannabe came back to bite my in my butt on my second flip. I found that it was much harder to find new guys and that some of the guys that I had fired on my first flip were actually pretty reasonable people compared to the new guys I found. A few of those guys on my first flip, in hindsight, were actually diamond in the rough type contractors that I was pretty lucky to have found. I let my ego get ahead of me and let little issues escalate without ever attempting to reach out and solve them mutually.

      Nowadays my policy has changed and I’ve found that my projects are going smoother and most everyone is happy (at least half the time) 🙂


  3. VERY GOOD ADVICE. I am beginning my real estate investing and EVERY newbie should read this blog. EVERYONE, as a matter of fact.

    Thank you so much for a very, very good piece of advice. My mother told me that quote as well, ” You’ll catch fly’s with honey instead of vinegar.” 🙂

    Mark Gould

    • Mark,

      Glad you liked the article and thank you for your comment. Please share it to everyone and anyone you think could benefit from it.

      The reason that quote has been around for so long is because it is simply true.


  4. Great article Glenn.

    I like to think I am honest, some times brutally honest. As with you I try to invest with my personality as the style template. I love to help others but also have a win for myself as well. Knowing myself, I don’t think I would have handled that situation the same way. I know that it might have left opportunity on the table but I also could not help myself from addressing the issue if we were to work together going forward. I would have most likely granted their request and been cordial and just not worked with the agent going forward. If I did work with the agent going forward, I would need to address the rudeness. If they blew it off or didn’t understand what I meant after an explaination, I could not move forward. If they stated that they were having a bad couple weeks or even better didn’t realize their tone and additude, I could see a way forward. My only reason for this is that I am a small operation and have more opportunities than I have the resources to close currently so I don’t have a great need for such a contact. But more importantly without corrective action, I would not feel comfortable with a “professional” acting that way with my customers, guests, or other members of my team. Too risky for me.

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