Real Estate Investing as a Side Job for Pilots

9 Replies

Hi All,

This is my first post, so hopefully I have this in the right spot in the forums, but I have always been fascinated in real estate, especially in buy and hold and house flipping.  That being said, I am a pilot and while I don't have much free time on my hands in my current role, there a number of pilot jobs with pretty cushy schedules... 7 days on 7 days off, or on call 24/7 but you really only get called 15 days a month.  Are there any other pilots on BP that have been able to be successful in the real estate investment scene?  Or is that a bit of a pipe dream?

With that schedule its actually pretty easy. I started when I was a Federal Air Marshal.  I was in the air 5 days a week and sometimes on shot notice out of the country for a week or two.  

All you need to get started is an internet connection and parts of a team.  Actually all you need at the start is a RE lawyer. 

The super bonus is that you have plenty of time to read, and that is very powerful  

So click the auto-pilot switch and start investing

To your success


Hi Josh,

Thanks for the input! It's great to here that others in the same industry have been able to make it work. Truthfully, being able to read, learn and grow is probably one of the biggest perks to this kind of schedule. I am really excited to get started up on the whole REI thing and I have been soaking up every thing I can (forums, BP podcasts, recommended reading lists, etc). Thanks again


@Taylor Kitchens

  no difference than any other person who works and invests.. but as Josh suggests if your flying long haul you will have time to study... were I lived in the Napa valley we had about 30 plus pretty senior SF based guys most were very senior flying asia or transacon. and they had plenty of time actually would have to worry about getting their number of TO and Landings in  :) lest they have to go to the sim. ... they loved golf... So I became very good friends with many .. some had no interest in RE but I know a half a dozen who did very well with it.. buying commercial in Napa... some buying rentals in other states.. One thing you have the advantage of ( well little tougher now but being a pilot you can get jump seat) you can get to places for free were others have to pay.

Yeah, those guys who do the long haul international flights are definitely at the pinnacle of the flying career... decent money, decent schedule, live wherever you want... the trifecta :-)

@Taylor Kitchens

Always have a passion to help people who has a job and want to get involved in real estate investing (partially because that's how I started). Anyway, enough about me.

Will take a lot of time to map out the entire investment strategy, but here is one high-level advice.

You should always find a person (or couple people) who you can count on so that you can remove yourself from being onsite (since you might be at working ie. flying).  The rest are more "off-site" management where you can do it where-ever you are, whenever you can.  At the beginning you will have a lot of things that you have to do yourself, but as you systemized your work more and more, you create yourself more and more free time (or at least you become more efficient).

Good luck in your investing journey. 

@Taylor Kitchens

Welcome! Besides the information provided already, I recommend you to pick up the phone when you are not traveling and talk to a few people. To me, I think that the time spent on doing research and reading is part of your investment cost (as your time is valuable). Talking to a few people on the phone can accelerate this process much faster and this will help your ROI.

good luck!

Hey Taylor! Fellow(ette) pilot here. I don't fly commercial, I only do it on the side for fun, but I'm an instructor and have banner-towed and all that fun jazz. I instruct now on the side as my fun gig. How long have you been flying? Who do you fly for?

In terms of investing while flying, how it can be structured is completely dependent on what kind of investing you want to do! Rentals, flips, wholesales, etc. will all have completely different demand schedules (ranging from none to a ton), so that will determine how best to do it.

Hi Taylor:

You might want to google the name Pete Gauthier for some inspiration. I have read a little about him but have never met him. He apparently was a pilot who flew overseas routes. He got into wholesaling in the Baltimore area and has been very successful (not sure if even he flies anymore). 

Well wishes to you!

I fly for Dynamic Aviation actually. I have been flying for them for about 5 years.  I have taken a bit of a hiatus from a lot of the flying side of things and am in a managerial position right now, but the free time that comes with a lot of charter gigs and being freed up to pursue RE investing is very alluring.  

Truthfully, I have seen a few of my colleagues find charter gigs with a decent schedule who don't end up doing anything all that productive and I found myself wondering... is there something about that type of situation that isn't conducive to REI, or are people just not that driven? Good to hear that not only can it be done... it's not that uncommon :-)