From Sleeping On A Park Bench To Speaking On Stages In New York And Geneva | Iris Fynn

She went from sleeping on a park bench in Johannesburg to speaking on stages in New York and Geneva. But some of Iris Fynn's hardest lessons came after she found success. In this episode of Cheers to Failure, Nontokozo Madonsela sits down with Iris Fynn for an extraordinary conversation about homelessness, family, marriage, leadership, grief and the hidden cost of always being the person everyone depends on. For years, Iris opened her home to her extended family at Christmas, cooking for as many as 100 people. Then she lost her job, her marriage fell apart and money became tight. That Christmas, not one family member invited her and her children for a meal. The experience forced her to confront an uncomfortable question: when you're always the one giving, does anyone notice when you need help? Iris also speaks candidly about the biggest regret of her marriage. She put the needs of her extended family ahead of her husband, even when he pleaded for time alone together. Looking back, she wishes she had understood the importance of boundaries before it was too late. And in one of the episode's most startling moments, Iris recalls dismissing a pregnant employee after concluding that the working relationship could not continue. She says the woman then threatened to blow up her car. It's a revealing story about the difficult decisions leaders sometimes have to make, even when they lead with empathy. She also shares what happened when she was held at gunpoint with an AK-47 after running out of petrol in Johannesburg, why her greatest fear in that moment was for her children's future, and how losing loved ones changed her understanding of grief. Iris's story is not about pretending to be strong. It's about learning when to give, when to ask for help, when to protect your peace and how to get up again after life knocks you down. IN THIS EPISODE: ◽ From homelessness to international speaking stages ◽ Growing up in a large family with a Zulu chief for a father ◽ Learning resilience from a mother raising 13 children ◽ Receiving devastating family news before addressing 5,000 people ◽ What to say, and what not to say, to someone who is grieving ◽ Why strong people struggle to ask for help ◽ Hosting Christmas for 100 people, then being left out when she needed support ◽ The boundaries she wishes she'd set in her marriage ◽ Being held at gunpoint and confronting her financial planning ◽ Her approach to buying and renovating property ◽ Finding her voice as a woman in the boardroom ◽ Giving colleagues credit for their work ◽ Firing a pregnant employee and facing a frightening threat TIMESTAMPS 00:00 Defining failure: getting back up 01:13 Growing up with a Zulu chief as a father 02:43 A mother raising 13 children 03:49 Choosing joy after difficult days 04:06 Learning of her sister's death before going on stage 05:28 Why grief looks different for everyone 07:51 The worst thing to say to someone who's grieving 10:43 Why showing up matters more than saying the right thing 11:47 Why asking for help is so difficult 14:17 Friends who showed up without being asked 16:33 Hosting Christmas for her extended family 17:08 Losing her job and marriage, then being left out 20:49 Confronting her family about Christmas 22:50 From a park bench to stages abroad 24:44 Forgiveness, revenge and the woman who took her husband 25:55 The marriage regret she still carries 29:10 What vulnerability really means 33:30 Held at gunpoint with an AK-47 35:45 Fearing for her children's future 38:40 How the experience changed her planning 41:41 Buying, renovating and selling property 45:45 Responding to criticism 47:16 Earning your place in the boardroom 54:42 Why leaders should share the credit 57:33 The reality of corporate politics 01:02:36 Calling out disrespect at work 01:04:33 Rebuilding broken trust 01:06:34 Firing a pregnant employee 01:07:37 Quick-fire lessons Content note: This conversation discusses bereavement, violent crime and threats of violence. 🔔 Subscribe for honest conversations about failure, resilience and the courage to begin again. Follow Cheers to Failure: Instagram:   / cheerstofailure   Hosted by Nontokozo Madonsela. #CheersToFailure #IrisFynn #NontokozoMadonsela #Leadership #Resilience #WomenInLeadership #SouthAfrica