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From SilverSpoon to a Silver Dollar 

Written by Storyteller: Adara Bernstein   Comments: 2


Ross Hamilton grew up entitled. Privileged, good looking, wealthy, connected – all the world seemed to be at his feet. Ross was also, in his own words, ‘an a-hole’.


“When I wanted something, all I had to do was ask for it. Actually I didn’t even ask; I demanded.” Cars, electronics, vacation spots, toys, whatever he wanted, he was granted. “My parents were ridiculously lenient with me. They were both pretty involved in their own lives, and like many typically wealthy parents, they assuaged their guilt by buying me things.” His father, who passed away two years ago from a heart attack, brought on, Ross believes, by a stressful life, was an executive at a large company. His mother was and still is involved in many non-profit causes and devotes her time to fundraising and socializing.


It was Ross’s father’s death that jolted him into a more realistic world. That and the friendship of a friendly ice-cream scooper named Clara.


Ross attended private schools his whole life. He partied with royalty and heirs and heiresses. His life seemed to be laid out before him – party hard in his younger years, get a well paid, easy job from one of his father’s connections, and live the good life.


“When my father passed, very unexpectedly, I got the biggest shock of my life. My father had not left me much of anything in the will. He gave me a ‘stipend’ of living expenses of $50,000 per year. I was used to spending fifty grand in the matter of a couple of weeks.”


Upon the reading of the will, the executor, the long term family lawyer, apologized profusely to Ross, whom he’d watched grow up and felt very kindly towards. Both the lawyer and Ross’s mother were shocked. Apparently Ross’s father had altered his will without consulting the family lawyer or his wife.


At first Ross’s mother told Ross not to worry, that she’d take care of him. There would be no substantive change in his lifestyle. However, as they read through more of the legal language, they discovered that allocating fund diversions to help their son could amount to a forfeiture of her own access to the family fortune.


“To say I was dumbstruck would be an understatement. My mother’s tone changed, for her to be ‘punished’, as she put it, because of my father’s feelings towards me, was unthinkable.


“I also quickly learned who my real friends were. As soon as the word got out that I was cut out of the will, many of my so-called friends started drifting away. No one outright shunned me; hell, for all I know they just felt bad and wanted to not make me feel awkward by not being able to pay my own way in fancy hotels and trips,” Ross shakes his head in amusement.


But then, it was far from humorous. Ross hadn’t really been given “real world survival skills.” He certainly had his connections, albeit through his father, but had never so much as written a rent check let alone be responsible for his own finances. He was used to getting a handout from his parents whenever he needed it.





“Ross Hamilton grew up entitled. Privileged, good looking, wealthy, connected – all the world seemed to be at his feet. Ross was also, in his own words, ‘an a-hole’.”



The resentment against both his parents ran very deep. He was angry at his father for blindsiding him like that, and for his mother for not supporting him. This anger gnawed at him until no one wanted to be around him and his unpleasantness.


Ross started hanging out in the strip mall nearby his modest apartment. In this row of old storefronts there was a small ice-cream store that had free wi-fi, so he’d often take his laptop and buy a root beer float and spend the day surfing the internet, trying to figure out how the “real world” lived.


“I cannot tell you how eye-opening that first year was. At first I completely panicked- froze. I had no idea how to function, even where to begin. I couch-surfed at my rich friends’ houses until they got sick of me. I of course resented them and my overall anger was driving everyone away. I was a miserable human being.”


Eventually Ross got an apartment and learned to put together a resume. When he reviewed it, he realized that the “internships” he’d done were all jokes – things he’d put down as his father’s colleagues allowed him to use their names that he’d done “investment” and “consulting” when in fact he’d show up for a couple of lunches and rounds of golf. He never so much as lifted a pencil or opened a spreadsheet.


Ross enrolled in a technical training program and taught himself how to learn many of the business applicable software applications. “My Art History major wasn’t going to land me a job. I needed some real skills.”


While sitting in the ice cream parlor he began noticing a young girl who worked there after school. She’s bring his rootbeer float with a smile and always seemed in a good mood; no matter how much Ross scowled at her, she’d always ask him how he was doing and seemed genuinely interested. They began to talk and Ross learned that she was 17, working afternoon shifts so that she could take care of her baby in the mornings (her boyfriend, also 17 and very unhappy about being a father so young, worked the night shift) and she was hoping to pass the test to get her GED.


Clara’s situation, even where Ross sat, looked depressing and hopeless. 17, already a mother, struggling at a minimum wage job and working towards her GED? He realized though that they weren’t really all that different when the outer trappings were stripped away. “She was braver than I was. Here she was, living a crappy life, or seemed crappy to me, and yet she was always so happy! I never saw her down, never heard her complain.”



Ross and Cara, friends for life



Clara encouraged Ross to find something he was passionate about. It was in these late afternoon conversations, when business was slow, that Ross realized he wasn’t passionate about anything, “except maybe spending money as fast as I could.”


Eventually Ross found that he had a real passion for computers. He learned coding, gaming, and basic graphical element design standards. From this, an idea began to germinate. The only problem? He needed some start-up capital.


Ross went to his mother, and told him her idea. She agreed to a small fund to get him started. The lawyers approved it all, and he hired a couple of developers he’d met in school and they are working on a start-up company.


“If my company takes off, I will have done it on my own. Finally, finally I will understand why my father did what he did. I have a lot of respect for him now. My old lifestyle is gone. I will be successful, some day, but it will be on my terms. There is no greater legacy he could have left me.”


Ross smiles, a charming smile that could get anyone to open up their pocketbooks, but Ross is determined to make it by spending as little money as possible. There is one thing he will splurge on though, when he is successful – a new car. “That, and I’ll do something really nice for Cara, since she inspired me to believe in myself and showed me that the world isn’t a crappy place.”

And he has promised to let Story of My Life do the first interview of him when he's reached his first million.


Thank you Ross, for sharing your Story with us.


Our Stories and pictures are the sole copyright of their Authors and may not be reprinted or used without their permission.

© 2009 by Adara Bernstein and Story of My Life

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Member Since
Aug 2007
Archibald Sharron said:
posted on Jul 28, 2009

Mr. Ross, this was a lovely example of how shining human beings can be when shown a mirror.

You'll go far.

With regards,
Archibald Sharron

Member Since
Jul 2009
Sarah Tuskow said:
posted on Jul 29, 2009

VERY inspiring!