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In 2022, I realised I was a context expert after discovering what I knew was unknown to others. Within MasterJack, this was a part of the plan – to become content marketing experts. At the time, it felt like a BHAG (big hairy-arsed goal), and I set the intention to say ‘yes’ to any opportunity that acknowledged the goal.

What followed were speaking engagement opportunities as the content marketing expert at a few high-profile conferences. And now, in 2024, I find myself a podcast host. Even my inner voice says ‘wow’. I want to say I don’t know how I got here. But I do. It’s because I said yes. Sure, I’m dealing with imposter syndrome on the inside, but that voice is getting quieter the more I, well, do it.


The first important thing is that you don’t say yes to everything. You say yes to what aligns with your goals. For example, saying yes to what makes you uncomfortable because the goal is growth or trying new things.

So here I am, with guidance from a speaking coach, hosting a podcast when I’ve never been a guest on one. And so far, I’m enjoying the ride – well, honestly, the enjoyment part comes and goes as you deal with stress or nervousness – but it came down to just doing it. It is not perfect; just done. So, I’m sure we’ll look at the first few episodes once we’re down the track and likely cringe a little. But it doesn’t matter because we started. And we know we’ll get better and better.

The first lesson I learned is that most of the guests, so far, are dealing with a little bit of imposter syndrome, too. They also didn’t know that what they knew was valuable.

The second lesson is that the gold is always in the follow-up question. It’s the same when I interview a client for their content. Even if I pre-send the interview or podcast questions, the good stuff happens after that first answer. Here’s a crude example:

What do you do for a living? And the answer is straightforward. It’s almost a boring answer. But whatever their answer is, the follow-up question would be:

Why did you choose that? And then comes the gold. Either they don’t know why, and now I’ve unwittingly begun their mid-life crisis, or you get the story of their experience and how they came to value what they do. And when people hear that part of the answer, they can align with it.

And that’s how you get the people you want around you: clients, suppliers, listeners, etc. Because they’ve connected with something you said, it’s not about how good your product or service is; it’s about the stories behind the why.

This podcast is called ‘Boxers & Briefs’ and is produced by Gilligan Sheppard. It is aimed at business owners, managers, and decision-makers. We’re not trying to sell anything, and it’s genuinely trying to provide value to make businesses better.

Why ‘Boxers & Briefs’, I hear you ask? Boxers, because Gilligan Sheppard has a reputation for standing up for what’s right. Briefs, because it’s a snippet of information that informs someone. It’s a podcast with real-life business stories.

As with every piece of content, it should finish with a CTA; with this one, you have a couple of choices. You can listen to the podcast on  Spotify or Apple Podcasts. You can call me to arrange a time to interview you to get the gold from your business.