June 24, 2025

Josh Szeps | 'Uncomfortable Conversations' - A Journey Through Media Broadcasting, Podcasting, Writing, TV & The Career Of Australia's Best Interviewer

1 hour 27 minutes

Uncomfortable Conversations Podcast

Uncomfortable Conversations Substack

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Josh Szeps is a broadcaster, political commentator, and in my opinion, Australia's best interviewer.

He has, afterall, conducted thousands of them… and from many different pulpits. Whether it’s podcasting, Huffpost live, or radio, Josh has interviewed everyone from the biggest celebrities in the world, to academics, to geopolitics, to culture wars, comedy, economics and all the rest in between - it’s incredible how flexible Josh is and how well he can extemporaneously talk about or ask the right questions of, seemingly any topic.

He’s also someone who has been doing this for decades, and seen from the front row the two most significant disruptions to media over that time. I wanted to get something evergreen on Josh’s worldview and evolving timeline of a career…
Josh Szeps is the creator and host of one of my favourite podcasts, ‘Uncomfortable conversations’, and author of a substack by the same name.

00:00 - Who Is Josh Szeps
05:16 - Navigating Career Paths: Serendipity and Ambition
18:08 - Finding Aliveness: Reflections on Career and Life
22:34 - The Journey to New York: Opportunities and Challenges
33:19 - The Journey to HuffPost Live
37:39 - Memorable Interviews and Guests
39:20 - Preparation for Interviews
42:21 - The Importance of Collaboration
49:12 - Norm MacDonald & Joe Rogan
58:41 - The Joy of Media Engagement
01:00:02 - Navigating Life Changes and Career Transitions
01:10:50 - Alan Jones
01:11:52 - The Influence of Podcasting
01:12:35 - Living in Australia vs. the US
01:15:09 - The Future of Independent Media
01:21:40 - Innovating in Media Formats

...more