Sam White: The CEO Who Fired Herself

It’s safe to say that firing yourself is a rather unique experience in business. But this is an entrepreneur that has made a career of challenging the norm and thinking differently. Whether it’s taking on the male-dominated insurance industry or questioning the culture of high company valuations (AKA “Ponzi schemes”), she’s not afraid to blaze her own trail.

With refreshing honesty and unwithering self-reflection, in this conversation with Sam White, Founder of Freedom Services Group & Stella Insurance, we cover being “unemployable”, leading teams across the globe, raising funding as a woman, and much more.

Here's what we discussed:

• If we listed your achievements to date to a younger Sam White, what would her reaction be? (00:23)
• Were you an entrepreneurial person from a young age? (01:03)
• Could you give us an overview of your career to this point? (02:17)
• You describe yourself as “unemployable”, is that something you notice in your peers too? (05:28)
• You started a psychology degree at university, you have a podcast called “Human Business”, where does your fascination with the mind and what makes people tick come from? (07:20)
• You’ve fired yourself as CEO – could you tell us about that story? (10:16)
• You’ve always been a disruptor with your businesses, but as this disruptive native always been within you and how did it manifest itself? (13:43)
• Did you find that leading teams in the US and Australia were different to ones in the UK, and if so, how did you adapt your leadership style? (15:21)
• What has your funding journey been like? (19:25)
• You touch on female funding in your own podcast, have you been shocked at the stories you’ve heard on the podcast and in the female entrepreneurs you come across? (23:10)
• Have you noticed an improvement since you first started fundraising to now? (25:41)
• Do we need to change the relationship and view of failure, and did you notice a difference in the attitudes towards failure between the US and elsewhere? (31:47)
• What are your thoughts on the trend of companies raising a lot of money, with wild valuations, before even turning a profit? (37:48)
• The Good News Postcard: What is the hardest challenge you've ever faced as a business? (42:06)
• What makes a great business leader? (43:28)

Thanks to Oscar from the Jill Dando News for bringing us The Good News Postcard this week. Get your dose of positive news by visiting The Good News Post, a website collated by hundreds of young people aged 8 to 18 in the UK. They've written real-life “news that’s good for you”, covering people, animals, stories to cheer people up, and tips to make lives better.

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