Be Honest.. What Challenges are you having in this business?

[Rob Gillespie]

I am writing this post more for the seasoned Investors.

It is very easy to see the results that everybody shows online, flying in private jets, not working, building hospitals in third world nations, but I want to hear the REALITY of what life is like for the seasoned investor out there!

I will begin by saying I am over 23 years in the business and full time form over 20 of that.

I work at it every day, there are always problems to solve from tenants, to banks, city inspectors, CONTRACTORS (LOL), etc...

I am blessed enough to have so many connections in my market that I can maintain deal flow of great off market properties with equity and not have to spend a ton on marketing. This allows me to offer great deals to my investment buyers around the world that like to invest in the Cleveland market. 

I never missed any of my kids events (unless I wanted to, LOL)

I have made a TON of connections which has opened up many business opportunities for me because of real estate. 

I am able to travel to Florida every month and still run my Cleveland Real Estate Operation. (I fly private on my big jet with 300 of my closest friends and allowed Spirit to wrap it for marketing purposes :-) )

My biggest challenge is that I believe Residential Real Estate can provide an amazing lifestyle, better than most surgeons, but it is not scalable enough alone to take me to the next level. 

My internal debate is should I move on from what I know so well after doing more than 1000 deals and start swinging for the fences on repurposing shopping malls or something, or stick to what I know and do well. (NOT LOOKING FOR AN ANSWER, JUST GIVING EXAMPLE OF MY OWN DILEMMAS AS A SEASONED INVESTOR)

Let's hear how REAL LIFE REAL ESTATE INVESTING is going for you and what can make it better!

Looking forward to responses!! Thanks!!!

[Account Closed]

Originally posted by @Rob Gillespie:

I am writing this post more for the seasoned Investors.

It is very easy to see the results that everybody shows online, flying in private jets, not working, building hospitals in third world nations, but I want to hear the REALITY of what life is like for the seasoned investor out there!

I will begin by saying I am over 23 years in the business and full time form over 20 of that.

I work at it every day, there are always problems to solve from tenants, to banks, city inspectors, CONTRACTORS (LOL), etc...

I am blessed enough to have so many connections in my market that I can maintain deal flow of great off market properties with equity and not have to spend a ton on marketing. This allows me to offer great deals to my investment buyers around the world that like to invest in the Cleveland market. 

I never missed any of my kids events (unless I wanted to, LOL)

I have made a TON of connections which has opened up many business opportunities for me because of real estate. 

I am able to travel to Florida every month and still run my Cleveland Real Estate Operation. (I fly private on my big jet with 300 of my closest friends and allowed Spirit to wrap it for marketing purposes :-) )

My biggest challenge is that I believe Residential Real Estate can provide an amazing lifestyle, better than most surgeons, but it is not scalable enough alone to take me to the next level. 

My internal debate is should I move on from what I know so well after doing more than 1000 deals and start swinging for the fences on repurposing shopping malls or something, or stick to what I know and do well. (NOT LOOKING FOR AN ANSWER, JUST GIVING EXAMPLE OF MY OWN DILEMMAS AS A SEASONED INVESTOR)

Let's hear how REAL LIFE REAL ESTATE INVESTING is going for you and what can make it better!

Looking forward to responses!! Thanks!!!

I am becoming worried about the huge cultural shift against landlords.  Not just the moratoriums and cancel rent, but social media has become an echo chamber of anti-landlord rhetoric.   I have been attacked out of the blue on social media, yet I have some of the nicest homes, most tenant-friendly policies (except for very strict screening policies) and very few evictions and code complaints over my years doing this. I give back to my community and actively participate in it, but lately people just get mad that I exist. 

It doesn't affect the actual operation of my business YET, aside from the moratorium, but I know politicians are listening, and I see how the winds are changing. I am not afraid of nationalization or any other conspiracy theories, but I am getting worried about the reactivity and vindictiveness of the average nutcase (which do exist on both ends of the political spectrum).  I've always just held my property in my name and easily discovered LLCs, but on my to-do list now is how to get them into an anonymous ownership entity without upsetting my mortgage companies or insurance company.   I do like the newer PC term "housing provider" but the angry people will always revert back to "landlord" just because it sounds so evilly Victorian. 

Just crazy times.