--- title: The Weight Of Winning- Inside a Rich Life Built from Nothing description: Glenn Toby’s story reveals how childhood homelessness shapes mental health, resilience and purpose, offering hope and support for vulnerable communities author: Dr Marina Nani (Editor-in-Chief) date: 2025-07-15T08:06:27.000Z updated: 2026-02-26T22:05:16.636Z canonical: https://richwoman.co/article/the-weight-of-winning-inside-a-rich-life-built-from-nothing image: https://cdn.nanimediahouse.com/6jyoil2ghvk.jpg categories: Philanthropic Minds content_type: Profile region: New York City publication: Rich Woman Magazine --- The eight-year-old boy walked down the street towards his Brooklyn home, carrying his school bag and the lightness that comes with not knowing everything can disappear in an afternoon. But then he saw it: all of his family’s belongings dumped on the pavement. Furniture, clothes, the small things that make a house feel like home, all scattered across the concrete. His mum stood there, looking at their life spread out in front of strangers, searching for answers she didn’t have. That image stayed with Glenn Toby. Not as motivation or inspiration, but as something deeper, a fear that lived in his body, a memory that would follow him through decades of what others would call success. The shock of losing everything in a single moment doesn’t just teach you about resilience. It teaches you that safety is temporary, that the ground beneath you can shift without warning. Glenn’s mum had lost her job. The landlord had acted quickly. There was no time to prepare, no chance to soften the blow for a child who didn’t understand why their things were now public property. They ended up in a bin bag, carrying what little they could salvage, walking away from the only home Glenn had known. ## What Stays Behind The thing about childhood homelessness is how it rewires your nervous system. [Research shows that experiencing homelessness in childhood leads to increased psychological distress in adulthood](https://bmcpsychiatry.biomedcentral.com/articles/10.1186/s12888-021-03142-0), with the earlier the onset, the higher the likelihood of lasting mental health challenges. For Glenn, that day on the street wasn’t just a temporary setback – it became a permanent resident in his mind. The fear didn’t leave when circumstances improved. It followed him through foster care, through the instability that marked his childhood years in New York. Even as he built a career in entertainment, working with artists like LL Cool J and guiding Olympic athletes, the eight-year-old who lost everything was still there, waiting for the next catastrophe. Glenn has spent his adult life in rooms with successful people – celebrities, athletes, leaders who trust him with their careers and their fears. But he carries his own private terror of losing it all again. Like [Sharon Rosenbloom’s journey through grief and adversity](https://richwoman.co/article/sharon-rosenbloom-a-single-mother-s-triumph-over-grief-and-mental-health-struggles), the trauma doesn’t disappear because you achieve professional success. In his recently released [TEDx Wilmington talk](https://www.youtube.com/watch?v=ENeSh6kVtcc), Glenn frames his story as a change story: ‘Your pain has a purpose. And your story has the power to change lives, starting with your own.’ But the reality is more complex than that neat narrative suggests. His pain didn’t change into purpose – it became the foundation for everything he built, including the parts that still hurt. When Glenn founded [The Book Bank Foundation](https://thebbf.org) in 1997, it wasn’t just about giving back. It was about being around people who understood what it means to lose everything. The foundation serves communities affected by homelessness, providing books yes, but also mentoring and support for people living the life Glenn once lived. The foundation has grown beyond its original mission of promoting literacy. It now addresses abuse, hunger and homelessness directly, working in communities where children carry the same fears Glenn carried. [With 1.3 million children under six experiencing homelessness each year in the United States](https://campaignforchildren.org/resource/policy-brief-child-youth-and-family-homelessness-in-the-united-states-undercounted-misunderstood/), Glenn’s work reaches into a crisis that affects millions of families. ## The Weight of Winning What the success stories don’t tell you is how hollow victory can feel when you’re waiting for it to disappear. Glenn has built Glenn Toby Enterprises, advised global leaders, shaped careers that span entertainment and sport. But success doesn’t erase the muscle memory of loss. It doesn’t stop the part of your brain that scans for threats, that never quite believes safety is permanent. There were moments in Glenn’s career when professional wins felt empty because they couldn’t touch the scared child inside. There were setbacks that brought the old fear flooding back – not just the fear of failure, but the specific terror of having your belongings dumped on the street whilst strangers watch. The late actor Lance Reddick, whom Glenn advised, once spoke about the complexity of success after struggle. Athletes like Olympian Samyr Laine, who trained under Glenn’s guidance, understand that achieving your goals doesn’t automatically heal what broke you first. Glenn’s work with these individuals wasn’t just strategic – it was personal. He recognised their fears because he lived with his own. ## Living with What Happened Glenn’s story isn’t about overcoming trauma – it’s about learning to [live with it](https://richwoman.co/article/breaking-the-cycle-of-trauma-how-childhood-trauma-survivors-find-healing-through-storytelling). [Research on childhood homelessness reveals that the toxic stress experienced during these periods disrupts brain development](https://www.acamh.org/blog/homelessness-impacts-on-children/), creating lasting emotional and cognitive challenges. The eight-year-old who lost everything doesn’t disappear when the adult achieves success. Some days, Glenn still feels that old fear. A cancelled meeting, a delayed payment, any small sign that things might be shifting – and he’s back on that Brooklyn street, looking at his life scattered on the concrete. The difference now is that he knows the feeling, recognises it as a visitor from the past rather than a prediction of the future. His work with The Book Bank Foundation isn’t charity in the traditional sense. It’s communion with people who understand what it means to rebuild from nothing. [ Gelnn turned his own experience of homelessness into a currency for helping others](https://richwoman.co/article/stacey-ellis-homeless-and-addicted-to-helping-others) and is mentoring homeless children not just by offering guidance, but by sitting with the part of himself that never quite stopped looking over his shoulder. Glenn’s TEDx talk delivers a message of hope: ‘Your pain has a purpose. And your story has the power to change lives, starting with your own.’ But for people like Glenn, purpose doesn’t cure pain – it gives it somewhere to go. The scared eight-year-old is still there, will always be there, but now he has company. The foundation continues to serve communities affected by homelessness, working in the spaces where children carry bin bags full of belongings and mothers search for answers they don’t have. Glenn’s success isn’t about leaving that world behind – it’s about building bridges back to it, creating the kind of support he needed when his own world collapsed. Three decades after founding his foundation, Glenn understands that his story isn’t unique. Millions of children experience the trauma of homelessness, and many carry those fears into adulthood. [Finding purpose within adversity](https://richwoman.co/article/finding-new-purpose-imani-blackmon-s-mission-to-help-athletes-write-their-next-chapter) is how you live with what happened – not whether you overcome it, but how you let it shape the person you become. For Glenn Toby, every day is still touched by the day he lost everything. But now, instead of running from that memory, he works alongside it, using his success to create the kind of safety net that wasn’t there when he needed it most. The bin bag full of belongings became the foundation for a life dedicated to making sure other children don’t have to carry theirs alone.