Unmasking Generosity: A Wealthy Man’s Quest to Transform a Community

Apr 21 / Tamera Stewart
If you remember last week's story, Jerry decided to go undercover as someone without a home in order to decide where to best donate the millions he amassed during his life but had no one to leave it to. When his favorite barista of 20 years passed away, he was struck to find out that she was homeless. It made him realize that he had spent the better part of his 76 years judging people and treating poorly the ones he decided were not up to his standards. But after 35 years as a successful ad man for a major media outlet, it was he that was alone. All the money in the world hasn’t changed that.

Beyond the Facade of Charity

On the 4th day of his journey he left the downtown area of glitz and glam nonprofit buildings where he 
originally believed he would find the best home for a sizable donation to do good to help those like Susan, his favorite barista. Just a few miles away from where he was forced to leave after holding a door open and wishing well a young executive for a large nonprofit who’s online presence made them look as if they had a staff of kind people doing amazing things, he came across a small, 2-story brick building with a malfunctioning neon sign reading “The Hope Chest”. He remembered how his realization that you can’t judge a book by its cover had brought him to this moment and decided to go in with an open mind. The result couldn’t be worse than being thrown out of the place for being kind, right?

The Humble Abode of Hope

As he opens the heavy door leading to the small reception area with two old couches and a small table and chairs, he is greeted by a young lady who’s name tag reads ‘Assistant Manager’ with the name ANNIE in block letters below it. She seemed so young to him, but she had a deep understanding of how the world really worked in her bright blue eyes with a smile that revealed she had been through more than her share of rough times for her age. She was dressed for the office but clearly not in a $1000 custom made suit like the young executives downtown sported, as the suit was just a bit oversized for her small stature. Her long golden brown hair swayed back and forth as she walked towards him with an outstretched hand. Her welcome was warm as she asked Jerry if he would like some water or coffee and a soft place to relax as she would like to learn how they can help him. He was so taken aback by the stark difference in his reception that Annie thought she had done something wrong by the look on his face. She quickly asked if he was okay and if they could continue their conversation on the soft sofa, sensing by his face he had something he wanted to say. Jerry said he would love a cup of coffee and he sat down on the sofa as Annie went to the kitchen area to get it.

From Useless Fortune to Fulfilled Purpose

Jerry sat there feeling conflicted. Since the movement of print media onto the internet, he had looked into the online presence of a company before dealing with them, since that is what he spent the last 15 years of his corporate life creating - deciding what to show online in the ads he ran for his company and who to partner with to further enhance their overall presence. But he hadn’t found this organization online, he found it via a faded flyer in a park he walked past where many of the local homeless community stayed. Jerry was conflicted because every part of him was screaming to come clean to her that he could help them instead of him being the one needing help. But to do so without doing any of the research that made him so good at his executive job felt like something was wrong. But he again remembered it was doing things the way he had always done them that led him to being alone and in this place to begin with, so he trusted his gut for the first time in decades.

When Annie returned with his coffee, she asked Jerry again if he was okay. He turned to her with a smile on his face and began to tell her who he really was. That he was not there in need of their services but was looking for a way for his money to do the most good since he knew it wouldn’t do him any good once he was gone. Annie began to cry once the shock and excitement died down a bit. It warmed her heart knowing their little organization would be able to afford to help more people than ever with the basic items so many with homes take for granted, such as socks and warm blankets and clean water. She revealed to Jerry that money was not their only urgent need. Annie explains their biggest need is for volunteers, as it doesn’t matter if their warehouse is full, if they can’t get resources to the people who need them. She invited Jerry to join them as a volunteer, she was sure they could find a place he would fit in. 

This led to Jerry revealing an even bigger surprise...

A New Chapter for 'The Hope Chest'

Jerry got excited. He hadn’t thought about helping in any way outside of a large donation, but his skills from his corporate life could help ‘The Hope Chest’ create a plan for their online presence to rile up supporters to begin volunteering their time. He left there after this emotional meeting knowing how he will spend the time he has left…once again using his connections and talents from before he retired. His skills in building an online persona and digital ads will easily convert into creating a digital advocacy plan which will ensure this organization will never again struggle to find people willing to help, with their time and money. 

As Jerry embarks on his mission to amplify the voice of 'The Hope Chest' through his wealth and his knowledge within the digital realm, it serves as a reminder of the power that each of us holds in the digital age. If Jerry’s story has inspired you to harness your own skills for a cause close to your heart, we have an opportunity that awaits. Our upcoming EchoBreaker Bootcamp is designed to equip you with the same impactful methods Jerry will be utilizing—strategies that can turn a whisper into a roar for any initiative you are passionate about. Visit our digital learning page to unlock the potential of your passion and become a beacon of change in your community. Together, let's move from inspiration to action, and from individual effort to collective triumph.