I Raised $1 Million, Bet Everything - And Lost It All | Gary Rathbone скачать в хорошем качестве

I Raised $1 Million, Bet Everything - And Lost It All | Gary Rathbone

What happens when conviction outruns reality? In this powerful episode of Cheers to Failure, Gary Rathbone unpacks one of the most consequential failures of his life: walking away from a senior executive role, betting everything on an ambitious pan-African sports media vision, raising $1 million, relocating his family across continents, and ultimately watching the venture collapse. Gary reflects with rare honesty on hubris vs humility, the danger of mistaking a great idea for a viable business, and what it really means to exceed your own limits. He speaks openly about losing investor money, the weight of responsibility to his team and family, and the long emotional aftershock that follows financial failure. Threaded through the conversation is the quiet but powerful influence of his grandfather. A figure of strength, integrity, and restraint, his grandfather’s values become a moral compass Gary returns to when confronting shame, responsibility, and the question of how one lives after losing everything. This is not a story of overnight redemption. It’s a story about living with the consequences, staying in the arena, and choosing humility over bravado when life doesn’t reward your courage. In this episode of Cheers to Failure, Gary discusses: ◽ Betting everything on a single vision ◽ Raising and losing $1 million in investment ◽ Leadership responsibility when things fall apart ◽ The cost of hubris and the value of restraint ◽ Legacy, integrity, and the influence of his grandfather ◽ Why failure teaches more than success ever could This episode is about accountability, perspective, and learning how to stand again without pretending you didn’t fall. 00:00 Opening the conversation on failure 01:20 Why failure is more defining than success 04:15 Understanding limits vs chasing ambition 06:00 Leaving a senior role to bet on a pan-African vision 10:20 Raising $1 million and relocating his family 14:30 Where the business model started to crack 19:40 The moment reality didn’t match conviction 25:45 Losing the investment and facing responsibility 31:00 Hubris, humility, and the lessons that stayed 36:40 The influence of his grandfather and legacy 41:20 Living without revenge or redemption fantasies 47:30 How failure reshaped how he makes decisions today 50:40 What parents must teach children about failure Hosted by Nontokozo Madonsela Follow Cheers to Failure: Instagram –   / cheerstofailure