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All Forum Posts by: Bob Wilson

Bob Wilson has started 4 posts and replied 49 times.

Post: Successful Short-Term/Airbnb Rental Investing Out of State

Bob WilsonPosted
  • Rental Property Investor
  • Chicago, IL
  • Posts 51
  • Votes 31

My business partner and I have been in sales for 15+ years so we scoured social (online) and real businesses and pitched them for 1-2 years (2017-2018)

Once we got 1-2 major contracts (minor league hockey team & health care company), word of mouth and reputation did most of the work. 

We still jump on zoom calls every week pitching and selling though, it’s what we like… the chase. 

Now we have companies calling us daily for housing needs, and we turn away 90% because we never have availability. 

Goal now is to scale so we can start saying “yes” more then “sorry, we are 100% occupied”.

In short, every company has corporate housing needs. Think about it, they all use hotels. We didn’t create anything new. We simply redirect their attention to a better product and value for their $

Sales 101


Post: Successful Short-Term/Airbnb Rental Investing Out of State

Bob WilsonPosted
  • Rental Property Investor
  • Chicago, IL
  • Posts 51
  • Votes 31

We are not investing out of state yet, but are setting up the guidelines and infrastructure as we speak. 

Be nice to hear from others on this. 

Our goal is to build out Chgo over next 18 months, then test a new market in 2023, and go big in 2024 with franchise type opportunities across other markets. 

We do corporate housing though, so less volatile. Average stay is 5-6 months and all contract based so professional folks. Backed by their companies. 

Just from local experience, I’ve learned, you will need a point person on ground, someone you can trust and who won’t bail on you when the “work” hits them. 

All else can be figured out, but you need that rock on the ground for ya. 

Post: Hiring Lawn Care Personnel or....

Bob WilsonPosted
  • Rental Property Investor
  • Chicago, IL
  • Posts 51
  • Votes 31
Originally posted by @Crystal Smith:

It looks like. you're getting great advise. One of the things I love about BP is learning about new companies/startups that are trying to solve a problem. We proposed LawnLove to our management company who use to have in house people cutting the grass & we've proposed it to clients we represent on listing where the homes are vacant. $35 every other week for a normal size lawn seems like a good deal. 

Thanks Agreed! Great advice (mostly), and I now have a solution :)

Post: Bookkeeping Software Recommendations

Bob WilsonPosted
  • Rental Property Investor
  • Chicago, IL
  • Posts 51
  • Votes 31

I don’t have automation, but we use QBO 

My wife is the automation lol 

Seriously though, I actually like reviewing transactions, we learn so much more about what’s happening behind the “financial scenes”. 

I just told her last week, I want to use quick books for our personal accounts starting January for the same reason. Easy to catch things when you have to file each transaction away somewhere. 

Post: Hiring Lawn Care Personnel or....

Bob WilsonPosted
  • Rental Property Investor
  • Chicago, IL
  • Posts 51
  • Votes 31
Originally posted by @Joe Norman:

It sounds like the hassle is in the weekly billing, which is understandable. Will the lawn care companies invoice you on a monthly basis? Thats what my lawn guy does and it works just fine for both of us. I don't require proof that the yards have been cut but I've never had a complaint or any inkling that they aren't getting done.

Another option, as others have stated, is to have the tenant take responsibility for the lawn.

 We do monthly as well. 

We have had a couple complaints over the last 1-2 years, and we have been invoiced for something "not cu", which we found out through our cameras and tenant feedback. 

Post: Hiring Lawn Care Personnel or....

Bob WilsonPosted
  • Rental Property Investor
  • Chicago, IL
  • Posts 51
  • Votes 31

@Allan C.tell me more…

I tried a company called “lawn starter” and they were a joke. Couldn’t find people to handle the job, unbelievable. Is that company running on a different model or what do you know.. 

Post: Hiring Lawn Care Personnel or....

Bob WilsonPosted
  • Rental Property Investor
  • Chicago, IL
  • Posts 51
  • Votes 31

@John Clark @Aaron Gaffney



Concentrating in a few towns doesn't generate $6,500-$7,500/monthly, spreading out is how we dominate our industry John. 

Aaron, I agree, but since grass is present, I'm just looking for other options then working with 5 companies at once. I get it, not a easy solution aside from sticking with these crews and perhaps switching to bi-weekly schedule.

Post: Hiring Lawn Care Personnel or....

Bob WilsonPosted
  • Rental Property Investor
  • Chicago, IL
  • Posts 51
  • Votes 31
Originally posted by @Joe Splitrock:

We have only single family homes and require the tenant does lawn care and snow removal. I am assuming that is not an option for you, but thought I would put that option out there. 

In my experience, $30-35 per cut is a fairly good rate. You may see 15 minutes of work between two people, so it looks like only 30 minutes. The total time is probably over an hour when you include travel time and breaks. Travel time is a huge cost in that business and it is why none of them will do all your properties.

Forcing them to upload pictures is really micromanaging and it is probably wasting extra time for your wife. I would consider other ways to streamline payment. One way would be to contract at a monthly rate. Tell the mowers you will pay $120 per month for weekly mowing and you will send payment on X date each month. My company used to do this at our facility for lawn and snow, so we had a fixed monthly rate. 

I am not sure it is practical to hire an employee to do this:

1. This is only a part time and part of the year job. The type of person taking work like this is more prone to quitting or not showing up. Any decent employee will want year round full time work. Maybe you could find a partially retired person or college kid to do it, but otherwise I see issues.

2. You are calculating 5 cuts a day and thinking that is five hours, but don't forget maintenance time, travel time, breaks and allocation for bad weather. I could see 5 cuts a day becoming a near full time job. 

3. As others mentioned, you have to worry about vacations, sick employees, people just quitting, work injuries, etc. You will also have equipment maintenance and purchase cost. 

4. Even though you have less contractors to manage, now you have an additional employee to manage. Someone needs to make sure they cut the lawn and do a good job. You have the liability aspect which means you need insurance coverage.

My advice is negotiate a monthly rate and pay it on the same day every month. If your systems allow it, set it up as a recurring payment that is automatic for the mowing season. If you are worried about them not mowing, you could ask them to just just send text every time they mow or install cameras at the property. Depending on property size, security cameras may not be a bad idea anyways. 

 We have exterior cameras at all units. ok, so forget the pics, I get it. 

Our tenant pays $6,500-$7,500/monthly, so while we can "require" them to mow lawn, in my opinion, it's something we should handle for that cost. Good feedback though, thx.

Post: Hiring Lawn Care Personnel or....

Bob WilsonPosted
  • Rental Property Investor
  • Chicago, IL
  • Posts 51
  • Votes 31
Originally posted by @Colleen F.:

@Bob Wilson   If the hassle isn't worth it forget the pictures, if you have established relationships that is a bit much.  Have them submit their invoices. Trust buy verify doesn't mean you have to check on them every mow. 

Another thought is if you hire someone  it is not a really attractive job.  They would have to want to work only part of the year.  They would have to have a truck set up for towing a trailer.  They would need to be insured. It is too much time commitment for a part time job for some retired person but not enough for full time and its only part of the year. And they would have to be reliable and not want vacation during the summer. 

Great points! 

Post: Hiring Lawn Care Personnel or....

Bob WilsonPosted
  • Rental Property Investor
  • Chicago, IL
  • Posts 51
  • Votes 31
Originally posted by @John Warren:

@Bob Wilson I feel your pain. I am at 82 doors now, and all of my properties are close together in Berwyn, Cicero and Lyons. The main issue with trying to in source is that you could easily create an even bigger problem. What happens when your guy goes on vacation for two weeks in the middle of the summer? What happens when your guy quits in the summer? What happens when your guy takes longer than he should to do the work and you are actually paying more than you were before? 

It all comes down to opportunity cost. It sounds like you are doing a great job building out a portfolio. You also are a real estate agent. Make sure you are not spending your time chasing pennies instead of earning dollars. 

Great questions, I don't have all the answer, yet. :) 

I wouldn't go this route without investing in the trailer/machine as a company, that way we can have our assistant property mgr. assist when the primary person is on vaca or sick. It's a deal breaker otherwise, because to your point, that will happen.

As far as taking longer, that also could happen, but 5 lawns a day shouldn't take more then 5 hours. We both know, professionals take 15 min to hit a yard. Contract will have to be specific of course. And perhaps hourly isn't the best option vs salary. Many things to consider.