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Josh Szeps | From Olly The Kookaburra To 'Uncomfortable Conversations'

New Pod: Josh Szeps - 'Uncomfortable Conversations'

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A Circuitous Journey Through Media Via Broadcasting, Podcasting, Writing, TV & The Future

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

What makes him the best interviewer? Charm, wit, research, but also experience… he has, after all, conducted thousands of them, and from many pulpits. Whether it’s podcasting, HuffPost live, radio, or one of the many other platforms Josh has hosted, he 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. 

Navigate to the interview here, via the timestamps…

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

Consider sharing this interview with a mate, colleague, brother, sister, whoever you think might be interested in this as well.

Here is a transcript of the opening exchange from the conversation…

Josh
What if every single sip is like this?

Ryan
auditory pleasure for the audience?

Josh
Yeah, there are probably people who get up there someone someone is furiously masturbating right now

Ryan
So you wanted that for a cold opening.

Josh
Exactly, I know what I'm doing.

Ryan
All right, Josh. So what I would just want to know is how a fellow from Australia made a big in New York and now pretty much lives on his own terms, writing, producing really whatever you want. Polish father Holocaust survivor, Australian mother. You studied media and law at university. foreshadowing by winning the best debater at UTS.

And then this is sort of where the timeline starts now in 2000 you're 23 years old and you're the voice of oliver kookaburra at 2000 Olympics

Josh
I was a voiceover actor, voice artist in my teens. When I was in my early teens, my dad, was a successful actor in Australia, got a call from his voiceover agent. They said, you know, do you know any young voices? And he asked if we, if my brother and I would be interested in doing voices. And so throughout my teens, back in the Halcyon days when before, but you could just hop online and get a random person in a random country to do a voiceover for you for 50 bucks. When it was unionized, you'd get 350 bucks or something, which in today's money is probably $800. Right. And, you know, yeah, for a kid, I mean, it felt like it was a million dollars a week every time I would do that. And I became one of the most, yeah, one of the most heard voices. partly as a result, and partly because I was a precocious show off, I got good at doing character voices as well. And so I didn't just do the...

Ryan 
Yeah, and thousands of dollars for a kid.

Josh
get us this magazine or something like that. It would also be funny, silly voices. And yeah, one of those it was actually it's actually an instructive anecdote how I got the Olympic the voice of the Olympic mascot. I should say I was never in a suit. Like I wasn't that person. They had the voices. They put dancers in the suits and they put voice people in the booth.

I was the only voice of this character who there was Sid, Millie and Ollie and Ollie was the kookaburra and it was pretty late at night by this stage I still lived with my parents I was yeah 20 maybe 20 when they were casting this I think no I must have turned 23 at the end of the year 2000 so they would have been casting this in the

Ryan
to what you're 23 in year 2000.

Josh
mid 90s. So I would have been in my mid teens. So I would have been maybe 15 or something 16 and It was late at night and I was doing either university work or high school work and I was exhausted and I remember it was very hot in the attic and I was just recording a demo for what I thought that the kookaburra mascot of the Sydney Olympic Games should sound like. And he was inventing this kind of like laugh where he would always be like, it's amazing, you know, that kind of thing. And, and I just thought this is exhausting. I want to go to bed. I'm over it. And I texted my agent and said, this

‘Show me the incentive and I’ll show you the outcome’ - Charlie Munger (goat of pithy quotes)

I want to grow this newsletter and I want to grow this podcast. Typically, fellow creators in my position will offer you (my dear reader/listener) some reward whereby, if you refer x amount of people I will send you y reward.

For every 5 people you bring to the newsletter, I’d send you custom merch (or something along these lines)

Now, as you know, I work full time at Quartr which means after a long days work, I am booking, researching, recording, editing and publishing a podcast plus (everything on this newsletter), and therefore only left with a few minutes for everything else that makes up a life.

And as such, setting up some type of rewards program hasn’t eventuated. BUT with that being said, I would nonetheless try to do something to incentivise you to share the show.

For the sake of transparency - about 5000 people follow the podcast across both Spotify & Apple, and several hundred subscribe to this newsletter. Not everyone listens to every episode, but so far in a 4 year lifetime I’m extremely chuffed with every new person - and I notice every. single. new. person

To get to the point where things are monetised I’d say tripling both of those metrics is necessary.

But for now, all I can offer is camaraderie - if you are reading this now you are, and will remain the most important viewership I will ever get… and this is because you are the early adopters. So all I can do is ask… if you enjoy this and if you know anyone who think might enjoy it as well - share it with them one at a time and share it on your socials to the masses. Follow the podcast wherever you listen to it and subscribe to this newsletter and bare with me, not everything will be directly interesting to you, but I endeavour that some of it definitely will be.

So pump your juice, send this to all your mates - and one day you’ll be able to say you were onto all this ‘Curious Worldview’ stuff from day 1.

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