Questions That I Should Ask a Possible Mentor

10 Replies

Hello everyone,

I recently discovered that an individual that I know personally from performing music is in the business of flipping houses. He is a contractor so he is pretty much active in almost the entire flipping process, including construction. After a brief discussion, I asked if he would mind talking about his profession one day because I was very interested in the business. He gladly agreed. I finally got the courage to send him a message and ask if he would mind sitting down with me for lunch or dinner one day and we could go over some details of flipping houses. Once again he agreed and we should be having that meeting within the next few days. He doesn't know this yet but I plan to ask him to mentor me. I also plan to make it worth his while by offering to help with acquiring the properties, making phone calls, picking up materials, and even helping with construction. I will be compiling a list of questions to ask him about his business to better understand what all is needed to successfully complete a flip. I already have a few questions thought up for the meeting, but I was wondering if anyone may have a few other important questions that should be asked that I may not even think to ask. I will list my original potential questions below. Please note that these will not be asked in this order.

How many flips, on average, do you complete in a year?

What types of properties do you look for?

Do you have your own real estate agent?

How did you get started in this business?

Which areas/neighborhoods do you look to buy in?

Would you like to do more flips per year or are you happy with the amount that you are doing now?

How many people do you have working for you?

What parts of the rehab are you not capable or comfortable doing?

I will most likely think of some other questions but of course I would love to hear what you all believe I should add so that I can maximize the content of our conversation. Any help is greatly appreciated!!

I wish you the very best on the new endeavor!! Ask if he has a proforma or excel deal sizer he uses to determine ROI, expected costs, etc... Having a deal sizer on hand makes quick work when going through so many deals. Ask what, if any, lenders he uses and why. Need a couple HMLs in place for scale-ability purposes unless pockets are deep of course. If he is experienced you may not be able to get the same leverage from an HML he would get until you've done a couple deals yourself so when sizing out your deals be sure to account for lower leverage possibility since you're newer to the space. Again, I wish you the best! Have fun getting your feet wet!

@Bryan Dumesnil . My personal opinion is to. It ask people to “mentor” you. Just be authentic and ask good questions like you listed above. The relationship will grow naturally and you’ll learn a ton, just don’t call it “mentoring”.

After your meeting, ask if you can go by one of his job sites and see this stuff in action.

I get asked all the time to meetup and discuss this stuff with people. I am usually open for it, but I don’t want to be called anyone’s “mentor”. I’m just a guy, doing some real estate stuff.

@Bryan Dumesnil

Hello Bryan, awesome that you're taking the step to reach out!  I know it's not easy, it takes humility, I've been in the same position.

I agree with Caleb about using the word "mentoring".   It might make him feel like he's on the hook for something.   If you just come at him with a genuine appreciation for him taking the time to talk with you, that will show him that you're eager and want to learn from him.     Sometimes less is more. 

A couple potential questions:

What are some of your goals?   This way you can help him reach them.   You help him reach his goals, he will be more apt to help you, and you will show him value.   I heard a cool saying on one of the podcasts "Rising tides raise all ships". 

Why are you a RE investor?  What's driving his "why".   There could be dozens of reasons.  Good to know what drives people and another way of seeing if you can meet a need.

I think one thing you can do  bring to the table to make it easy for him is to make a list of your strengths.  At least have 2 or 3 so he knows what he can come to ask your help with. 

Also check out BP Podcast #323.  There was a portion in there about reaching out to potential mentors.

Wish you the best!


@Joe Nizdil Thank you for the advice. I'm hoping to be able to offer something that he needs that will make me valuable. I have been listening to the podcast from front to back and I am about in the middle but I believe I will skip over to the episode that you mentioned so that I can be prepared as possible for this meeting.

@Jeff Seal Thank you! It was the best picture (in my opinion) that I had at the time and I figured someone else here was interested in the same hobbies as me, so that's the picture that I went with. If you ever find yourself on the gulf coast with your bike, look me up and I will try to make a ride with you.

Just to update everyone, I had the meeting with my "mentor" in the middle of last week. He invited me to his home and we sat on his patio and spoke about real estate investing as well as other topics for about 2-3 hours. I was amazed by how much he knew and how much he was able to help me in understanding the flipping process. He gave me suggestions on local contractors to use, where he would suggest buying, and how he manages his flips. He even put me in the direction of a local home in our neighborhood that he would suggest flipping. He added that he would have liked to buy it but he just recently purchased another home and he only does one flip at a time. He offered to walk through the house with me if I decided to take a look at it, so I took him up on that offer. He and I, as well as my wife took a tour of the home and he pointed out areas that he would repair and how he would do it. The whole experience was amazing!! My wife and I are currently thinking about putting in an offer on the home in hopes of completing our first flip. Hopefully with the help of my "mentor" I will be able to do just that with as little stress as possible. Thank you guys for all of your help!! I really appreciate it!

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