The Funniest Picture That Has Ever Been Posted on BiggerPockets.


My wife and I are attempting to sell our house.

It’s kind of crazy we’ve been in real estate for almost a decade, but we’ve never actually put our house on the market. Anyway, I’m a tight-wad and am hating all of this money we are spending.  Note, this is why I love rentals…

My wife say’s it’s a good ROI (return-on-investment.) We put our house on the market and everyone wants to see our house painted. Despite the fact that the paint is only 4 years old.

I digress.

My wife is now in-charge of the whole-thing and hired some painters. Standard sub-contractor drama ensues: late, slow, every excuse under the book.

Then it-happened.

She texted me while I’m at work the following:


He’s Asleep!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!

Not just nodding off, but this guy was straight-up asleep on a freaking ladder painting!

Hope you guys enjoy the humor.

If you have a funny contractor story, please share in the comments.

Photo: Bill Gracey

About Author

Jimmy Moncrief is a bank underwriter and real estate investor. He blogs at where he talks about all things real estate. He also is the creater of free evernote templates for BiggerPockets members to learn how to better organize and automate their real estate investing.


  1. Jimmy – great for a laugh first thing this morning! Did you wake him up by shaking the ladder (but only a little)? Hopefully he was insured in case he fell off the ladder, but I bet you had made sure he had insurance before you hired him:)?

  2. Unfortunately this is getting to be the typical hire in the contracting business. With the generous welfare system in place i.e. 99 weeks of unemployment, good hires are far and few between.

    Just a heads up in my industry (hvac) 53% of the present work force is over the age of 50 a large portion of those are 5-8 years from retirement. If you have a son or daughter who after graduating from college are going to have little chance of getting a job, I highly urge you to direct them into the mechanical trades.

    Any young tradesman with a head on his shoulders, good work habits and lifestyle habits (unlike your painter) will be able to write their own ticket in the next 5 years.

    If we continue at our present situation where government underwrites college but not the trades, finding contractors in the near future will be on the order of your painter as typical.

    People today look at labor as something to avoid, the better role is to attend college learn a skill set that in this world will be worthless by the time they graduate. I apply the 90-10 rule, 90% of the college graduates are worthless in the market place when they graduate most never use the skills they majored in.

    Let me close with something that was told to me at my first interview 30 years ago.
    “There are no good mechanics unemployed, unless they want to be.”

    • Dennis, I hear you loud and clear and you’ve touched on a very sore subject for me. I’ve been in financial aid for over 28 years and can’t tell you what a dilemma it is for trade schools to stay in business. The affect it is having on students who want to attend these types of schools is horrible. They want to gain a skill and get a job in the field as soon as they graduate, which usually takes about a year. Proprietary trade schools generate the largest number of students with trade skills and we have government officials, such Senator Harkins (Iowa) that has been doing everything he can and has been for years, to get rid of all proprietary trade schools. Google him and you’ll see exactly what I’m talking about. There are others in office just like him and Obama isn’t helping either – the government is squeezing trade schools out of the educational industry by imposing restrictions that are literally going to force all of them out of business and Obama is supporting the changes. Yes, there are schools out there just in it for the money to make their stockholders happy and line their pockets, but there are also schools that are legit and make students their #1 priority, pouring the profits back into teaching tools and equipment. They will go down with the rest of the bad apples”. I could write a 20 page article on this very subject.
      If you take a look at the education system in a country like Australia, they do recognize the value of students with trade skills and the government has set up a joint effort with employers to hire apprentices and their system is very successful.
      As far as needing students with these skills, my own son graduated trade school this past July and can’t get a job in the field. He can’t find any HVAC companies that are willing to hire apprentices – they all want someone who has been in the field at least 3 – 5 years, so the students who are graduating are pretty much out of luck.

  3. Dennis, great point about a shortage of tradesmen. I also agree with your age comment re HVAC. I only know old HVAC guys.

    Someone in the local REIA posted a string of you can’t believe it pictures. Urinals on adjacent walls practically touching each other, driveways off the garage at a 45 degree angle down a 10′ drop to the road. Obviously yet another case that the mantra that money knows it’s best use is NOT true. LOL Here in the South over development and dumb development used to be rampant. Now those local banks are bust. Good thing everyone got their commission and bonuses though.

  4. Had a woman yesterday ask me if I wanted her son-in-law’s phone number because he is an out of work contractor. I asked her why he is out of work as CA construction has picked back up. She said she doesn’t think he’s been looking for work. Had to toss that phone number in the trash.

    • Aaron Yates

      I think it’s a ‘painter’ thing. I had to fire a painter a couple months ago. He messaged me while at a Black Sabbath concert on a Tuesday night asking about work on Wednesday. I told him everything but the kitchen will be ready for paint.

      Wednesday morning arrives, I’m there… 7am, 8, 9 10, 10:30 I finally call him. He says he can’t make it to work unless I give him some gas money.

      I told him don’t worry about it. I’ll find somene else. He responded, no I’m on my way. I said nope. You’re done.

      You see I had taken the day off work to make sure he could come in and just flow right through the house and get it done. But instead I lost a day of pay and he decided he didn’t want to work because basically he must have spent all his money at the concert the night before.

      I used to be a flooring contractor in the housing industry. I have done window cleaning, some painting. I am now a contractor in the auto industry. I will never understand these guys who want money up front or then demand money immediately the day the job is done before allowing me to verify their work.

  5. Out of state home owner asked if we could help with a sub contractor or a handy man to fix few things before we put the home on the market.

    Same story, late for work, really slow on the job, made extra trips to home depot. You have to wonder why he didn’t get everything needed for the project first time? Excuses and more excuses! Long story short got the job done and didn’t get paid for the extra visits to HD.

    Both photos are too funny, possibly has a hangover from too much partying the night before ? haha!!

    Has he seen this photo?

  6. I hope you made sure that the contractor’s certificate of insurance showed workers comp coverage, because your homeowners insurance probably won’t pay if he falls off the ladder.

  7. I’ve never had a sleeping painter but I’ve had a drunk painter. He was fine in the morning but once he got into the beers everything went down hill. By the end of the day his cut-ins were a wavy disaster. I cut him loose and found a new guy. This one had full-blown OCD which is actually a great quality in a painter, as long as they’re not working hourly.

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