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How I Got Money From a Homeless Person

Real Estate Agent with Progressive Realty (Boise Idaho) www.Progressive-Realty.info DB-17066

ActiveRain's December Challenge is about sharing Love and Joy this holiday season.  I had a very humbling experience a few years ago while visiting Portland, Oregon.  We were playing tourist and stopped at VooDoo Donuts since it is a legendary stop.  While waiting in line, a disheveled man approached me asking if I had any change I could spare.  I am not used to being asked for money from strangers and am not used to just giving my money just for the asking.  I responded that the parking meters took all my change.

To my surprise, he reached in his pockets and handed me the entire contents, $1.37.  He said, "Here buddy, you need this more than I do!" and then he walked off.

My son was impressed.  He said, "Dad, you are the only person I know that can convince a homeless guy to give you money!"

When we were served, I tried to find him again to give him a few donuts and $5; however, he was gone.

Another time, a homeless guy asked me for $0.65 since it was a nice day outside and he was $0.65 shy of being able to buy a quart of beer to drink while listening to a concert.  I appreciated his honesty and gave him $5.  He tried to stop me saying he only needed $0.65.  I acknowledged it and told him I appreciated him being honest and to buy a six pack and share with a friend or two.

Years ago, I was in Las Vegas for a real estate conference.  Patty Luther and I took the city bus to Old Town so she could get a feel for the locals instead of taking a taxi.  The man sitting in front of us smelled of urine, vomit and alcohol.  She asked him if someone gave him $100, what would he do with it?  He said he would go buy more alcohol.  Had he said almost anything else, she would have handed him $100!

Another time, I was talking with a real estate client of mine about homelessness.  He had been homeless in the past.  I asked him how to determine which people actually need the money and which ones don't.  His response shocked me . . . "If you have to ask, you are not worthy to give."  I still struggle with that answer to this day.

Back in my college days, I qualified for a national competition in Chicago.  At that time I met my first entrepreneur of the worlds' oldest profession.  I was so clueless that when she propositioned me, it went right over my head.  She made her way around the block and asked again, and I decline her company a second time.  Finally, the lights went off and the bells rang in my subconscious mind and I figured out what she was really asking.  I caught up to her and admitted my ignorance and asked if I would walk with her to learn more.  She said I was cute and asked if I could pay to talk?  I admitted that is what I needed to talk about since I was ignorant.  I ended up walking with her to a coffee shop, bought her a bagel and coffee and discussed her business model; then tipped her generously for her time. My fiancé at the time was sure shocked when she asked me about my trip and I told her I paid for (leased / rented) a hooker!

As I look into my goals and objectives for 2024, I think I will go back to that process when someone asks me for money.  I will offer to take them out for a meal (or bring one to them) and then donate to them afterwards. At least this way, I will see them as human beings, not just as a statistic.  I would much rather give to people and try to give them a hand up verses giving them a hand out. I would much rather donate money personally to those in need instead of through organizations that spend 50% or more on administrative overhead and salaries!

I have a friend that does a lot to help the homeless here in Boise.  I have already told him that I want to stand beside him and help him in 2024 so I can personally learn more about the people he so unselfishly gives his time and heart to. I intend to give away $20 a week to people that he identifies as "Caught being good".  Ironically, that equates to $1,040 which is the number on my tax forms that I might be able to put it on for a tax deduction as well.

What are your plans for charitable giving in 2024?  Will it be time, money, love, or ?

If we all do a little, we can accomplish a lot!  


Michael Jacobs
Pasadena, CA
Pasadena And Southern California 818.516.4393

Hello Jim - I like the path you took with this month's challenge.  And the question you asked of your previously homeless client will have me pondering for a while about his response.  That's worth the price of admission in my opinion.  

Dec 27, 2023 08:02 AM
Jim Paulson

Thanks Michael Jacobs.

I had another previous client that I was able to get into a new manufactured home in a park developed by the City of Boise many years ago.  I was friends with the housing director at the time and asked how to fill out the application for his address since he was literally homeless at the time.   He has income from his VA disability to cover his mortgage obligations.  He became President of their HOA a few years later. That was one of my smallest paychecks in real estate but it paid the largest yield!

Dec 27, 2023 09:06 AM
Nina Hollander, Broker
Coldwell Banker Realty - Charlotte, NC
Your Greater Charlotte Realtor

Leave it to you, Jim, to provide us with such a fun and fascinating series of stories! I've travelled all over the world and couldn't come up with any experiences like this! 

Dec 27, 2023 08:13 AM
Jim Paulson

Nina Hollander, Broker I give credit to my international travels for teaching me to getting outside my comfort zone is perfectly acceptable and forces me to grow and empathize. I need start doing more international travel again so I can appreciate what we have here in the US again.

Dec 27, 2023 09:09 AM
Kathleen Daniels, Probate & Trust Specialist
KD Realty - 408.972.1822 - San Jose, CA
Probate Real Estate Services

Hello Jim Paulson - this was a fun and funny read yet filled with kindness and love. 

"If you have to ask, you are not worthy to give."  Wow - I struggle with that as well.  

Good thing when you "paid for talking" the gesture was not witnessed by someone who may have handcuffed you in the least expected way. 

My plans for charitable giving in 2024 are to continue donating to the charities I have donated to for years as well as the new one I discovered this year T2T.org. I will also start to buy more food for strangers which feels better to me than giving them money. 

Thank you for participating in the December Kindness Challenge. 



Dec 27, 2023 09:42 AM
Jim Paulson

I can definitely relate to being careful when paying for certain "services".  Another fun story was on a trip to San Francisco, one of my friends wanted to walk over and watch the action at the nearby "red light district".  On the way over, two extremely attractive blond ladies walked by; one in a leather miniskirt and the other in tight leather hot pants.  That confirmed we were walking the right direction!

Walking back about an hour later, the same two ladies walked past us the opposite direction.  If either of my friends would have had a cell phone camera back then, I would be have been arrested for solicitation because I know for a fact I would have asked "How much" and before I could have finished my sentence "... for a photo to send home to my wife?" I would have been in (non-fuzzy) handcuffs since they were undercover (no pun intended) cops!

Dec 27, 2023 10:08 AM
Debe Maxwell, CRS

I had that same concern, Kathleen Daniels, Probate & Trust Specialist - why do you think he said that, Jim Paulson - I'm curious why" you are not worthy to give?"

Jan 07, 2024 12:29 PM
Myrl Jeffcoat
Sacramento, CA
Greater Sacramento Realtor - Retired

"If we all do a little, we can accomplish a lot!". . .That's a very important message!  

Dec 27, 2023 10:56 AM
Jim Paulson

Myrl Jeffcoat I came up with that sentence a few months ago and it now one of my favorite Jim'isms.

Dec 27, 2023 12:07 PM
Patty Luther
RE/MAX Rock-n-Roll Realty - Lewiston, ID
Lewiston ID Real Estate, Idaho-Washington

I remember that Bus Ride!  Happy New Year Jim   😘

Dec 27, 2023 02:07 PM
Jim Paulson

I will never forget it Patty Luther.  I will never forget the ride the owner of the company we worked for took everyone on either.  That story is even worse. Oh well, moving on!

Dec 27, 2023 03:03 PM
Lynn B. Friedman CRS Atlanta, GA 404-617-6375
Atlanta Homes ODAT Realty - Love our Great City - Love our Clients! Buckhead - Midtown - Westside - Atlanta, GA
Concierge Service for Our Atlanta Sellers & Buyers

Jim -

What a great response the person gave to you! 

I asked him how to determine which people actually need the money and which ones don't.  His response shocked me . . . "If you have to ask, you are not worthy to give." 
All the best - 

Dec 27, 2023 07:42 PM
Jim Paulson

I had some amazing conversations with him Lynn B. Friedman CRS Atlanta, GA 404-939-2727.  I knew he was ex military and after only about 15 minutes together I asked if he was in Special Forces.  He was perplexed asked how I knew.  I told him people as smart as he is don't end up with the masses.  He probably killed more human beings in close range than any hunter I know has killed big game; yet he had the most gentle heart.  He appreciated life and would literally tear up if we drove past a squirrel or cat that didn't survive the trip across the street.  He told me that the United States government spent over a hundred thousand dollars to make him an effective killing machine; however, they never "untrain" you! 

Dec 28, 2023 04:40 AM
Kat Palmiotti
eXp Commercial, Referral Divison - Kalispell, MT
Helping your Montana dreams take root

Another fantastic entry into this month's challenge. I love all the stories and your 2024 goals. Thank you for sharing. Carol Williams - a suggestion for 2nd Chance Saturday!

Dec 28, 2023 04:48 AM
Jim Paulson
Progressive Realty (Boise Idaho) www.Progressive-Realty.info - Boise, ID

Thank you Kat Palmiotti .  I think I will buy a new website domain and have a blog specifically to give shout out's to the recipients in an effort to generate interest in others doing the same random acts of kindness.

Dec 28, 2023 05:26 AM
Carol Williams

I love that idea, Jim Paulson 

Dec 28, 2023 08:00 AM
Brian England
Ambrose Realty Management LLC - Gilbert, AZ
MBA, GRI, REALTOR® Real Estate in East Valley AZ

Don't parking meters take credit cards these days?  I don't carry coins with me, so I would be stuck, haha.

Dec 28, 2023 05:46 AM
Patty Luther

not back then!  

Dec 28, 2023 10:57 AM
Jim Paulson

I am so frugal that I hit the button for my free 20 minutes and set a timer on my phone to use the app to buy more time.  

Dec 29, 2023 01:06 PM
Kathy Streib
Cypress, TX
Home Stager/Redesign

Hi Jim- I'm glad that you take the time to see people for who they are and learn about their situation. Often we lump people into categories. My friend's son who'd already survived 2 heart surgeries before he was in his teens was broadsided by (if I remember correctly) a drunk driver. His heart survived but he was left with neurological issues. I remember his mom saying that were it not for their ability to support him financially he would be one of the people we saw on the street. 

That opened my eyes. When we are approached for money Larry's of the opinion that they need it more than we do. 

In Delray Beach, an older woman lived on a street corner. Her home was a makeshift "tent" of large beach umbrellas.   Every day people dropped off water and food. I'm not sure what happened to her. 

I give to others not for what I'll receive in return or what I might gain. I give because it's the right thing to do.                             

Dec 29, 2023 12:18 PM
Jim Paulson

You are a great human Kathy Streib!

This post got me thinking and I bought a new domain so I can create a website to donate money through to people that do good for others.  I will write a blog about it in January as I get it launched.

Dec 29, 2023 01:09 PM
Wayne Martin
Wayne M Martin - Oswego, IL
Real Estate Broker - Retired

Good morning Jim. Stephen Covey said "seek first to understand". Kudos to you for doing just that for the disadvantaged. Most either give blindly or decline. You offer a valuable lesson. Thanks! Enjoy your day.

Dec 30, 2023 04:47 AM
Jim Paulson

Thanks Wayne Martin.  I actually just bought a new domain to do some fun give aways to people in my community that do good for others.  I think I can create third level domains for others to use to do the same thing.  It will be a fun and personally refreshing experience.

Dec 30, 2023 05:56 AM
Dorie Dillard Austin TX
Coldwell Banker Realty ~ 512.750.6899 - Austin, TX
NW Austin ~ Canyon Creek and Spicewood/Balcones

Good morning Jim,

Just reading your post as Carol Williams featured your post. What interesting situations you have encountered. I'm anxious to hear more about your new domain to do some fun and reward good deeds. 

Dec 30, 2023 06:44 AM
Jim Paulson
Progressive Realty (Boise Idaho) www.Progressive-Realty.info - Boise, ID

Thanks Dorie Dillard Austin TX 

Hopefully that domain will grow into an opportunity to expand in other cities/communities as well.  I selected the amount of $20 for each donation hoping maybe others will join in an annual "membership donation" since $20 a week x 52 weeks just happens to correspond the 1040 which is the IRS form to claim the donation.  I will have to get it set up as a non-profit next which I will.

Dec 30, 2023 06:57 AM
Leanne Smith
Dirt Road Real Estate - Golden Valley, AZ
The Grit and Gratitude Agent

Your entry was unusual and thought provoking. I have in the past offered to buy food for homeless individuals and the response is they want money even though they said they were hunger.  So I donate food to local food banks, etc. that way I know the donation truly is helping someone.

Dec 30, 2023 10:11 AM
Jim Paulson

Leanne Smith I agree that is a shame that people say they are hungry but then turn down food.  I have offered to buy them a sit down meal with me so I can learn more about how I can help them and none have ever taken me up on it. I also have turned toward donating to specific people or causes.

Jan 13, 2024 08:06 AM
Leanne Smith

I as well have limited what causes I donate to. Yes it is a shame.

Jan 14, 2024 06:51 AM
Sheri Sperry - MCNE®
Coldwell Banker Realty - Sedona, AZ
(928) 274-7355 ~ YOUR Solutions REALTOR®

HI Jim Paulson - What a great read.  I love how you included so many unique situations.  But, let's face it, when a homeless guy hands you money saying you need it more than him.  That takes the prize.  It is a shame that he disappeared before you could respond back to him with kindness.  You made your son's day though.  Haha

Dec 30, 2023 11:24 AM
Jim Paulson

Thank you Sheri Sperry - MCNE® I just got back from the Consumer Electronics Show in Las Vegas.  One common practice there is to have young ladies in Showgirl outfits soliciting money for a photo with them.  I told two sets that people usually pay for photos with Santa so can we each take a selfie and call it a trade? Neither time worked.  Next time, I will have to bring my Santa Hat and try again.

Jan 13, 2024 08:09 AM
Ed Silva, 203-206-0754
Mapleridge Realty, CT 203-206-0754 - Waterbury, CT
Central CT Real Estate Broker Serving all equally

Had a needy person given me money I would have felt so low as to look up to a shoe sole. The rest of your good deeds bear witness to charity and a bit of naivety.

Dec 30, 2023 12:11 PM
Jim Paulson

Ed Silva, 203-206-0754 I loved "so low as to look up to a shoe sole".  I had never heard that phrase before.  You also have me thinking of creating a "Naivety Scene" for next Christmas!

Jan 13, 2024 08:14 AM
Endre Barath, Jr.
Berkshire Hathaway HomeServices California Properties - Beverly Hills, CA
Realtor - Los Angeles Home Sales 310.486.1002

What an interesting historical recollection of your good deeds and also enjoyed the comments especially Kathleen Daniels, Probate & Trust Specialist  back and fort with you, Love your noble goals curious  about your interest of the Red Light District in San Fran:)Endre

Dec 30, 2023 03:03 PM
Jim Paulson

Endre Barath, Jr. the last time I was at the Red Light District in SF was when we were staying near there for a Coldwell Banker conference.  One of my friends wanted to go show it to us so we walked over.  Two stunningly beautiful women approached us walking the opposite way and they asked us if we wanted to party.  We cordially declined.  On the way back, they asked again.  I am grateful back then we didn't have cell phone camera's because I would have been arrested for solicitation when I would have asked "How much for " before I finished my sentence "... a photo to send home to my wife".  Our broker was with a number of other agents watching these two ladies since they were undercover (no pun intended) cops.  If we had said yes, the white "happy van" was actually the booking station so people.  We watched them arrest quite a few that night.  I am glad to say, the time in Chicago is the closest I have ever been to paying for a ladies time / services.

Jan 13, 2024 08:25 AM
Dr. Paula McDonald
Beam & Branch Realty - Granbury, TX
Granbury, TX 936-203-0279

Taking the time to help those who are less fortunate is notable. Love all of these memories that you've shared with us.

Jan 02, 2024 06:38 AM
Jim Paulson

Thank you Dr. Paula McDonald.  I am a firm believer in "You get more when you give."  

Jan 13, 2024 08:28 AM
Debe Maxwell, CRS
Savvy + Company (704) 491-3310 - Charlotte, NC

Oh, I love this and believe it or not, tried to comment on this last weekend! I happened upon it again today and realized my comment didn't take! UGH! 

I love your son's comment and really, I don't know anyone who could get change off of a homeless person. You really are amazing! 

Jan 07, 2024 12:26 PM
Jim Paulson

 am in Las Vegas for the Consumer Electronic Show and just shake my head at the women of the night here. They call themselves professionals and part of the world's oldest profession and yet none of them had a printed price list of options available of their services, resume, nor tell me how many 5 star ratings they had. 😜

Jan 07, 2024 02:02 PM