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!!!

@Rob Gillespie I want to keep striving to get better and continually learn so I can help others.

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!!!

Great post, Rob! I've had my share of ups and downs with the grind of investing in residential real estate, but have had pretty solid success with it overall (continuing to take 3 steps forward and then one or two steps back keeps on moving you forward as long as you stay in the game and keep learning along the way). 

It has definitely been a gradual process, slowly adding a property or two to my portfolio each year, but eventually getting to the point where I am now, with a reasonably substantial portfolio (mostly in Cleveland, like yourself). I am starting to explore other markets as well (mostly in TX and FL), likely following a variation of the same model that has worked well for me in Ohio... assembling a team of sorts, adding a property or two at a time. 

But like you said, there is a lack of scalability in continuing to grow by buying a property or two (or even 3 or 4) at a time. The phrase 'what got you here won't get you there' comes to mind. This is why I am pursuing or exploring other arenas now too. For one thing, I am focusing a lot on investor education (and already getting my feet wet), and the opportunities that can come with that stuff; there is definitely a scalable factor when it comes to that, via things like YouTube, course creation, etc. Secondly, I am starting to consider getting into development (or re-development) in this decade. Whether that takes the shape of developing/subdividing land for residential or industrial purposes, doing some new build projects (say, a development of a dozen new construction SFRs to sell off), or repurposing an old mall or warehouse (or whatever) remains to be seen... but I am currently in investigation mode and the wheels are spinning on the topic for sure!

Originally posted by @Rob Gillespie :

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 :-) )

Oh, I got a chuckle out of that.

As you know, here on BP we get a lot of people selling FOMO, the fear of missing out. The fastest way to get to a million dollars in real estate. The best states to invest in. Listicles all day with titles like, TOP TEN MISTAKES YOU'RE PROBABLY MAKING.

My Christmas Eve was spent lying at 30 degrees trying to breathe normally due to COVID-19 pneumonia. In the evening, I got a series of texts from a newly inherited tenant whose refrigerator had just died, to the point where she felt the need to mention, "IT'S ON YOU TO REPLACE IT." I got up off my COVID sickbed on the 28th and she got a new fridge, hauled into her apartment personally by yours truly.

But when her first month's rent was due, well...

"Hey, I've got my roommate's rent and $60 for my own rent and you're just going to have to wait until February for the rest of it."

Why do we rarely, rarely ever talk about these realities of running a self-managed C-class rental empire around here? No, no, it's passive income and boom-boom-boom and use-your-creativity to live a wonderful, magical life where all the pieces always fall in place and no one calls you during the holidays about busted appliances and when you make heroic efforts for them, tries to screw you over at the first opportunity.

Working with inherited tenants in the time of COVID-19. That's my challenge right now.

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.  

I think you illustrated many of the issues in your posts.  Those of us that have been doing this for a long time understand that this is a game of solving problems.  Every deal and every flip has unique problems that need a solution.  THIS is why I have trouble when those who are new are talked in to spending $20-50K to buy a guru's system.  There is not a system out there that can tell you the answer to every problem we come across

Originally posted by @Jim K. :

Originally posted by @Rob Gillespie:

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 :-) )

Oh, I got a chuckle out of that.

As you know, here on BP we get a lot of people selling FOMO, the fear of missing out. The fastest way to get to a million dollars in real estate. The best states to invest in. Listicles all day with titles like, TOP TEN MISTAKES YOU'RE PROBABLY MAKING.

My Christmas Eve was spent lying at 30 degrees trying to breathe normally due to COVID-19 pneumonia. In the evening, I got a series of texts from a newly inherited tenant whose refrigerator had just died, to the point where she felt the need to mention, "IT'S ON YOU TO REPLACE IT." I got up off my COVID sickbed on the 28th and she got a new fridge, hauled into her apartment personally by yours truly.

But when her first month's rent was due, well...

"Hey, I've got my roommate's rent and $60 for my own rent and you're just going to have to wait until February for the rest of it."

Why do we rarely, rarely ever talk about these realities of running a self-managed C-class rental empire around here? No, no, it's passive income and boom-boom-boom and use-your-creativity to live a wonderful, magical life where all the pieces always fall in place and no one calls you during the holidays about busted appliances and when you make heroic efforts for them, tries to screw you over at the first opportunity.

Working with inherited tenants in the time of COVID-19. That's my challenge right now.

Bruhhhhhh......You went into this chick's house while you had covid?

i guess that's one way to make sure they don't contact you on holidays anymore......

@Rob Gillespie

I recently bought my first property in Cleveland, SFH, in June. I rehabbed it, rented it out and I waited six months to do the refi but after I paid for the appraisal and was ready to sign the doc for the loan this Tuesday, I was told they can't do the loan now because the repair cost were paid outside of closing. I was told I have to wait to June to do the refi. So my challenge is learning the process but I am not discouraged. I will keep on trucking on.

Originally posted by @James Wise :

Bruhhhhhh......You went into this chick's house while you had covid?

i guess that's one way to make sure they don't contact you on holidays anymore......

 

Following CDC guidelines:
-----

You can be around others after:

• 10 days since symptoms first appeared and
• 24 hours with no fever without the use of fever-reducing medications and
• Other symptoms of COVID-19 are improving*

*Loss of taste and smell may persist for weeks or months after recovery and need not delay the end of isolation​

Most people do not require testing to decide when they can be around others; however, if your healthcare provider recommends testing, they will let you know when you can resume being around others based on your test results.

Note that these recommendations do not apply to persons with severe COVID-19 or with severely weakened immune systems (immunocompromised).

-----

Jim, I'm sure you know what it's like to get someone else to deliver a fridge between Christmas and New Year. 

@Jim K.

Damn Jim. I am still trying to recover from pneumonia after covid, and if I had to go pick up a refrigerator and haul it into a tenants house someone would probably be picking me up off the floor! Then getting stiffed on the rent...

My biggest challenge is the interference of government into my private affairs, essentially giving my deadbeat tenants carte blanche to squat for 12-15 months for free. 

It's INFURIATING.

Originally posted by @Jim K. :

Originally posted by @Rob Gillespie:

Working with inherited tenants in the time of COVID-19. That's my challenge right now.

Jim that is spoken as a REAL investor! So sad, but unfortunately I know how true that is! 

I hope you feel better soon!  

Originally posted by @Nicky Reader :

This is a real issue for our business for sure! The culture has shifted to anyone  making their own way being the villain. 
Unfortunately Property owners are perceived as greedy and opportunistic. 

Could possibly be a good future topic on how to overcome this public label. 

Originally posted by @Nicky Reader :

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.  

 All this happened in my country and it destroys the bussiness. Because if you cannot raise rent, you cannot evict, you cannot make people  fulfill the contract  (or at least governament doesent help you to do so) in the end return rates go down.

My country went from 5-6% ROI to 1.5% ROI currently. A disaster. And its all fault of the left wing media that convinces poor and low middle class that everything should be free (except left wing politicians obviously, those must be expensive)

Originally posted by @Gail W. :

@Jim K.

Damn Jim. I am still trying to recover from pneumonia after covid, and if I had to go pick up a refrigerator and haul it into a tenants house someone would probably be picking me up off the floor! Then getting stiffed on the rent...

Yeah, the holidays were less than ideal this year.

Originally posted by @Jim K. :

Originally posted by @James Wise:

Bruhhhhhh......You went into this chick's house while you had covid?

i guess that's one way to make sure they don't contact you on holidays anymore......

 

Following CDC guidelines:
-----

You can be around others after:

• 10 days since symptoms first appeared and
• 24 hours with no fever without the use of fever-reducing medications and
• Other symptoms of COVID-19 are improving*

*Loss of taste and smell may persist for weeks or months after recovery and need not delay the end of isolation​

Most people do not require testing to decide when they can be around others; however, if your healthcare provider recommends testing, they will let you know when you can resume being around others based on your test results.

Note that these recommendations do not apply to persons with severe COVID-19 or with severely weakened immune systems (immunocompromised).

-----

Jim, I'm sure you know what it's like to get someone else to deliver a fridge between Christmas and New Year. 

I moved down to Fort Lauderdale from Wooster, Ohio ten years ago. I feel your pain...mine was the weather lol. I've been in real estate for almost 50 years and it is different now and, I believe, about to get much more different. The good news is that we're able to do much more now than ever before, largely due to technology, which opens up a lot more possibilities than just landlording. The whole country is available to us. 

The economy is changing and we have to change with it. Here's how I did it This has only been feasible for the average person within the past 10 years or so. It offers diversification and a national reach.

@Edwin Rivera Hi,what does it mean repair are outside of closing. New here.

Originally posted by @James Wise :

Originally posted by @Jim K.:

Originally posted by @James Wise:

Bruhhhhhh......You went into this chick's house while you had covid?

i guess that's one way to make sure they don't contact you on holidays anymore......

 

Following CDC guidelines:
-----

You can be around others after:

• 10 days since symptoms first appeared and
• 24 hours with no fever without the use of fever-reducing medications and
• Other symptoms of COVID-19 are improving*

*Loss of taste and smell may persist for weeks or months after recovery and need not delay the end of isolation​

Most people do not require testing to decide when they can be around others; however, if your healthcare provider recommends testing, they will let you know when you can resume being around others based on your test results.

Note that these recommendations do not apply to persons with severe COVID-19 or with severely weakened immune systems (immunocompromised).

-----

Jim, I'm sure you know what it's like to get someone else to deliver a fridge between Christmas and New Year. 

 

Wife's Russian. I'm Greek, Jim.

There should be more of these kinds of posts on BP!!! 

"(I fly private on my big jet with 300 of my closest friends and allowed Spirit to wrap it for marketing purposes :-) )"

This made me laugh so hard 👆👆👆

Look, I totally agree with you about how hard things can get especially when building and scaling. I think the appeal of REI is the freedom it allows for average people and not so much the high life we see on Social Media of the rented, sorry private jet and red sports cars. I am still fascinated by the allure of everyday folks to these Lambo-driving characters. I guess it is aspirational? 🧐

For me, personally, apartment syndication is a different animal with different moving parts requiring multiple team members. All of what I am saying is so fresh as I am literally closing on an apartment building tomorrow. I was talking to my engineer friend, who is very quantitative and I told him I think I've probably received close to 1,000 emails as a data point relating to this deal in the last 60 days. 

I make this reference to say that it can be a lot of work that many people just don't realize until they realize it! A lot of work many normal people don't want and who can blame them. Yes, I also consider myself not normal lol 

Couple of challenges:
1. Raising equity to take larger deals down
2. Having enough time in the day for a young family and all the other competing priorities all of which are demanding my attention. 

So, I totally agree with you that just real estate may not take one to the next level. However, that next level has to be defined. For me, I am very interested in tech startups and proptech, so as I get older and acquire more assets, a lot of my wealth will also go into funding the next tech unicorns. Financial Diversification is never a bad thing. 

@Aasim Ali I am new too but my guess is that I needed to put money aside in an escrow account for the future repairs and document that in the closing documents of the purchase. My lender is now telling me I have to wait a full year to do my refi. I will reach out to other lenders to find out.

@Rob Gillespie getting capital to fund my acquisitions. So many great properties and not enough capital. I’m working on finding capital partners but that’s not an easy task.

My biggest challenge is finding plenty of off market deals. I have been growing, slowly, for the past several years. I have recently increased my available purchasing power but am having a tough time finding deal!

@Rob Gillespie

Working on making my first deal, sorting through lenders trying to find the right one for my situation. Getting started is tough but staying active on BP helps with maintaining motivation. Your accomplishments sound very impressive, congratulations. Looking to become a mentor? 🤷🏼‍♂️😁

@Rob Gillespie it is to me Rising cost of maintenance and repair I feel I didn’t sign up for. Construction labor is at least 30% higher than 5 years ago and I know materials are creeping up fast as well.