What is it like Giving Away $100 to a Random Person?

December 21, 2017

Build Family Wealth and Happiness.

Fill out this form to receive our free 39-page Family Wealth and Happiness guidebook. You'll also receive periodic updates from me to help you take your family to the next level.

Disclaimer: This post may contain affiliate links or links from our advertisers where we earn a commission, direct payment or products. Opinions are the author's alone, and this content has not been provided by, reviewed, approved or endorsed by any advertiser. Information shared on this site is for entertainment purposes only and should not be considered as professional advice.

Last week, I took on a giving challenge from Rockstar Finance. They supplied me with $100 and the guidance to “do some good” in my community.

I’m all about doing good, but I had no clue what to do with this money!

In my attempt to get some inspiration, I reached out to the Marriage, Kids and Money Community and asked for some suggestions. What I got back was incredible!

Here were a couple of the comments that spurred me into action:

Get totally out of your comfort zone…

Go all out, find someone who can't pay you back and bless him/her or them. I think you'll experience the most Joy and I'm sure they'll be happy too! Hope this helps.

Merry Christmas, Tre

Shortly after Tre’s email, I received this one from Peyton from Virginia:

I’ve always wanted to be one of those secret Santa’s that gives a random Wal-Mart shopper $100. If you can get others to agree to do it as well, I’d throw in $100 and be a local secret Santa in my community.  If it took off, this could multiply in a big way.


It was on!

Between Tre’s inspiration and Peyton’s specific instructions, we had the idea. Now it was time to make it happen!

Who Wants to Give For Fun?

At this point, Peyton was down with giving $100 of his money and our family was too.

In an attempt to get people to join us, I threw out a Hail Mary on Twitter, Facebook and even took my first foray into putting my mug on video!

The response has been incredible so far!

Over 100 social media comments have already come in encouraging our efforts. People have even chimed in about unique ways they like to give during the holidays.

Here are my 4 favorites so far:

You know what’s really fun? When you see an elderly person paying for one or two things with change you swipe and run!! Well, it used to be more fun when cards could just be swiped and then you could run. Now you have to wait for the stupid chip. But they usually don’t catch on until it’s paid and done. – Nikki

My husband and I were able to pay someone's mortgage for both December and January after an unexpected medical leave from his job.It felt so awesome knowing we really helped someone in a time of need. – Jen

I have a special police officer that I give a bunch of cash to at the beginning of December. He can hand it out to moms with issues that he sees in his community. I trust him to see some issues he can help. I also have some police in my area that know I have extra food and they can call me, pick it up and use for families or children in my area. Where I live is a bit rural. Some in need. They often call late at night. I’m ok with that. – Teresa

Planning to eat out and leave a super nice tip to some awesome waitress! One of my favorite things to do! Last year I didn’t get out of the restaurant fast enough because I ran into someone I knew and the waitress chased me down in the parking lot to thank me. She was in tears with appreciation. It made a big impression on my teenage kids! – Pam

We even got some folks to commit to joining us with our fun little challenge:

“I can’t wait to do this!” – Illyse

I gave 100.00 to a family in need.” – Elizabeth

“When and what time? We’re in!” – Safina & Sheraz

A couple we’re close to here in metro Detroit, Safina & Sheraz, helped us find the right place for our stealth giving adventure and brought their whole family along for the fun.

What Are We Supposed to Say When We Give the Money?

We arrived at the Salvation Army in Pontiac, Michigan on a chilly Saturday afternoon.

Salvation Army in Pontiac, MI

Salvation Army Pontiac mi

Once we got inside, we literally stood around for almost 15-20 minutes without taking action. Our feet were frozen to the floor. I didn't realize how difficult and awkward it was to just give someone some money!

My friend Safina went first with her $100. She approached a Grandmother with her 4 young grandkids and handed her an envelope with the money and wished her a blessed holiday. The grandmother gave Safina a big hug and the grandkids that surrounded her were all smiling and wondering what just happened.

After Safina's boldness, I got myself in gear. My wife pointed out a young mother with three small kids. I walked up to her and tapped her on the shoulder. She turned around and I handed her the $100 while wishing her a Merry Christmas. I told her that I hoped her and her kids had a great holiday and an even better 2018.

She was so happy that she asked us to take a picture with her. I was so happy/proud/nervous that I knew it was the right use for that $100.

BTW … It's Not For You, Andy

The last $100 we handed out to a father with two small kids in the parking lot. His reaction was priceless! I wished him a Merry Christmas and told him I wanted to have $100 for his family. He said “Thanks!” And then he walked away quickly.

It was literally as if he dropped a stick of gum and I was handing it back to him. That was the reaction I was preparing myself for when I went into this whole crazy challenge so it's all good!

When we first started planning this adventure, I was all concerned about the reaction we might get. But really it wasn't for me. It was for them. The second guy might have needed the money more than the first lady. Who knows, right?!

Here’s my reaction moments after it all went down:

Meanwhile in Virginia …

Peyton from Virginia (the guy who came up with this great idea) was doing the same thing last weekend!

Here’s how his story went down:

“After dropping the kids off for a parents night out, my wife and I stopped by our local Wal-Mart to look for someone we thought would benefit from this blessing. We walked around the store for a few minutes looking for a person or family and quickly decided to head to the toy aisle.

There were several individuals and families in the aisles and I quickly noticed a mother, grandmother, and about 2-year-old grandson looking at toys. I walked around the adjoining aisles a couple of minutes identifying a few other “targets” for this blessing. I saw two or three other individuals and families that I wanted to share this with as well, but I only had the one hundred-dollar bill, and wasn’t sure how I was going to approach just one family in a crowded aisle of many others.

But then I found myself right next to the first family again. As they walked around the corner, I pretended to look at toys in an aisle display. I was trying to figure out exactly how I was going to do this.  I thought, “this is the time.”

Go For it Peyton!

It was the first family I had spotted and they were right next to me now.  I turned around, the mother was pushing their cart and the grandma was holding the young boy.

I said “excuse me, have you heard of the secret Santa?” They looked at me with a little hesitation and said “yes”.  

I said “I’m part of a national secret Santa team” as I reached into my pocket and pulled out the bill. I handed it to them and said “Merry Christmas, please use this however you best see fit his holiday season”.

They both responded, the mother looked a little shocked and said “oh thank you” while the grandmother immediately started saying “bless you, bless you”.  I proceeded to say that all I asked is that they promise to spread some holiday cheer and good deeds before Christmas. With that I said “Merry Christmas”, turned around and we headed out of the store to go to dinner.

It seemed so quick and surreal for us. I wish we have had another four or five hundred dollars to do it a few more times, to share that blessing with all the families we saw on that aisle.”

Will You Join Us?

There are only a few days left before Christmas. We’d love for more folks to join us in providing some joy and happiness to neighbors in your community. If you decide to join in on the fun, I’d love to feature your name, where you’re from and your story on my podcast on Monday (December 25, 2017). Just email me and tell me about it!

Thank you Rockstar Finance, J Money, Tre, Peyton, Safina, Sheraz, Nicole, Zoey, Calvin and everyone who gives their money or time this holiday season. That’s what it’s all about.

Happy Holidays and Merry Christmas!

What is your favorite way to give during the holidays?


Andy Hill

Andy Hill is the award-winning family finance coach behind Marriage Kids and Money - a platform dedicated to helping young families build wealth and happiness. With millions of podcast downloads and video views, Andy’s message of family financial empowerment has resonated with listeners, readers and viewers across the world. When he's not "talking money", Andy enjoys being a Soccer Dad, singing karaoke with his wife and watching Marvel movies.


  • I read this just before Christmas on my phone one night, but just came back to watch your little clip. Honestly, I had tears in my eyes when I first read it, and how happy you and your family are in that video is just so infectious- I’m grinning from ear to ear!! 😀 Everyone has the opportunity to good for someone else. Definitely feeling inspired for the new year!!

    • I’m so glad to hear you enjoyed this Sarah! It was an incredible experience and it has opened me up even more to the joy of giving. Rockstar Finance is an awesome community. So inspiring!

  • Christmas Morning..I realize we have NO COFFEE..Fam on the way to the house..SH**..Head to Speedway and hope for K-Cups..Score K Cups..I walk up to the counter and I remember this post…pay for the coffee with debit card and hand the cashier a folded up 20 spot and say Merry Christmas…she gave a confused look but I pretty sure she was just stunned…I’m glad I can pass off a 20 to someone who is working and could use a break..THAT IS CHRISTMAS..

    • Thanks for including me in your “giving adventure”! Randomly surprising a neighbor in need with $100 was the highlight of our holiday.

  • This is great. I had the same trepidation when giving away the $100. What do you say to someone – oftentimes, there are so many issues related to money and shame / guilt, folks just don’t know how to react. Many often think there are strings attached to something like this. Cool to hear how you were able to overcome this and just give face-to-face.

    • Totally. It was awkward and awesome at the same time. We were lucky that the reactions we received we’re positive. It was a fun experiment.


Leave a Reply

Your email address will not be published. Required fields are marked *

Scroll to Top