All Forum Posts 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!!!

Looks like ya put a lot of time into research which is great!

Best advice I can offer is to TAKE ACTION! I see a lot of analytical folks getting caught 

up in paralysis of analysis. (not saying that is you, just telling ya what I have observed)

as I always say....

"Nothing works unless you do"

Good luck!!! You can achieve whatever you set out to do with the right plan and steam!

@Mario Cuartas

The biggest thing that eats up cash flow on low end properties  Is payment default. Cap x is not Bad on cheaper properties because you were doing the bare minimum to make it clean and safe.

It is cheaper to work on a Honda Civic then it is a Mercedes S class.

That is why I like section 8 for inner city because they have already inspected it and I know that it’s clean and safe.

As with any property, they need to be maintained. Beginning with a bucket of paint and keeping it cleaned up outside makes a world of difference in the perception of the condition.



@Mario Cuartas

Hey Mario,

I have done quite a bit in lower income neighborhoods throughout the years and I do understand your thought process about giving them a better property so perhaps they will treat it better.

That is a gamble that sometimes works out and sometimes does not.

The first thing to ask yourself when walking through the property is what makes it so bad? Is it lack of repairs, or is it lack of cleanliness?

On those properties I’m a believer to make sure the roof does not leak, the water runs through pipes and through drains, outlets are safe and the heat works.

I am currently selling a section 8 house that I just bought in one of those areas that is obviously safe, but not someplace that I would want to lay my head at night. With that said, there are plenty of people that would love to take over $800 per month in government pay for a $25,000 investment and could care less if the people did the dishes, LOL

I can talk about this all day and actually I may you a blog post on it because there’s a lot more insight I have.

I am sure it will work out for you if you buy in those areas and you’re involved in your properties. Best of luck!



@MarieChele Porter

I can understand your concern, however unless there was a pattern of things happening recently I would not worry about it.

As far as liability goes, anybody can sue anyone else at any time for anything, LOL

I am definitely want to give second chances to people trying to get their life in order.

In short, I would rent to them, however I would definitely tread lightly if there’s an eviction and not be the one to deliver the three day notice, LOL

Good luck!

Hi Ruben, 

There are plenty of options for that formula to work. 

If I were to go to North East Ohio  for those numbers, I would go out in the country outside of Cleveland. There is a much higher retention of tenants and fewer options for them to move. Less city inspectors (if any at all). 

I currently am getting ready to sell a property that is section 8 rented over 800 per month for 25k. This is NOT for everyone though, this is for a local or someone with boots on the ground to keep it going.The numbers may look good, but you will be EARNING that money every single month! IF you are living 1500 miles away and you want something more hands off, I would go to small country towns. 

Just my 2 cents. Hope that helps!

Hi Oscar, 

sounds like a straight forward finance from a local bank. Not sure where the property is, but it is unfortunate that some lenders still redline and will not make loans in certain areas. Depending on your score and money down, I could point you in a few directions. Feel free to PM me with details of the address and deal if you do not want to post them publicly. 

Good luck!

Hi David, 

Maxing out on lenders is a common problem. 

We are aligned with a few different lending sources that we offer investors that we do business with. We have Non Recourse lenders that are 9% at 65% LTV. sometimes our investors have 35% down, other times we carry a portion of that or have a gift of equity. I have a portfolio lender that is more credit based and they will go 70-75% LTV, but they are 30 year term, no balloon and 6-7% on the rates. They will also lend to Foreign Nationals, which is a big deal.

Just like a car lot, they can sell more cars because they make it easy to get the money. As an investment property provider, I find it necessary to have financial connections to get deals done. 

I am not saying to deal with me, but when looking at investment properties, always ask if the seller can help you get the money to do the deal. 

Heck even ask em to finance you! Keep in mind most landlords are not selling because they do not want cashflow, they are selling because they are tired of the tenants toilets and trash! Offer them to keep the money they love without the headaches! You would be surprised how many will say yes!

Good luck!! 

@Fang Underhill that completely depends on the market.

If you’re investing in a strong market that has great appreciation then you can pay market value for it.

If you’re in the market like Cleveland Ohio that has minimal appreciation then I do not believe you should be into it for more than 70% loan to value. The properties I sell to my investors usually have more equity than 30%.

Also take into consideration the terms you’re getting and the cash flow.

Best of luck!

@Sean Mooney It is never too late to start!

This all just depends on your strategy and goals.

Clearly I would not take out a 30 year mortgage and operate at break even Until it’s paid off, LOL

Depending on how cash heavy you are, I would buy some rental properties below market value and sell them off to your tenants and hold them as short term rentals with a nice upside.

You may even consider a self-directed retirement account to buy and sell with because you’re old enough to take distributions and you’re creating a tax free environment for your properties.

Good luck!