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‘Is this worth it?’: The difficult questions the Shameless founders have had to ask each other

For Zara McDonald and Michelle Andrews, both in their 20s, the building of their Shameless Media business came with challenges that men their age rarely face.

By Gyan Yankovich

Zara McDonald (left) and Michelle Andrews (right) have not only built an impressive media business, but also a solid friendship. Both wear Luuda shirts, $460, and pants, $460.

Zara McDonald (left) and Michelle Andrews (right) have not only built an impressive media business, but also a solid friendship. Both wear Luuda shirts, $460, and pants, $460.Credit: Hugh Stewart

Sunday Life’s most popular cover stories of 2023See all 11 stories.

Nine years ago, Michelle Andrews and Zara McDonald were both 20 and working entry-level jobs in Melbourne at women’s media company Mamamia. Covering late shifts, often on weekends, they’d regularly share an Uber home. A friendship soon grew out of their shared love of pop culture.

“We’d be watching the same TV shows and listening to the same podcasts,” says Andrews, now 29. Their back-seat chats eventually led to an idea: Shameless – “a pop culture podcast for smart people who love dumb stuff”.

The story of how they came to leave Mamamia – after having their idea rejected at the final hour – has been told many times. But these days, it’s not a moment they think of often, unless they’re asked about it in an interview.

“It ended up being amazing for us that they didn’t want the show,” says Andrews. Fast-forward to today, and the women are now well known as the “Shameless girls” – co-founders of Shameless Media, a company built out of their passion for smart conversations about pop culture.

“We feel so far removed from that time,” adds McDonald, 29, reflecting on their start. Since launching Shameless Media – the home of not just Shameless but also the Everybody Has a Secret, Shameless Book Club and Love etc. podcasts – in 2019, the company has gone from strength to strength. Today, it has 1.1 million followers across social media, plus 1 million unique listeners and 2½ million podcast downloads a month.

Michelle Andrews (left) wears Venroy linen knitted cross back dress, $200. Zara McDonald (right) wears Venroy draped jersey top, $160, Venroy draped jersey skirt, $200. Both wear  Converse shoes, $130, from Hype DC.

Michelle Andrews (left) wears Venroy linen knitted cross back dress, $200. Zara McDonald (right) wears Venroy draped jersey top, $160, Venroy draped jersey skirt, $200. Both wear Converse shoes, $130, from Hype DC. Credit: Hugh Stewart

For the first 10 months, Shameless was a weekend project, the podcast researched and recorded around the pair’s other jobs. In those early days, McDonald and Andrews were self-funded, buying their own podcasting equipment and spending just $70 to print advertising flyers. Even now, McDonald and Andrews have never taken on any outside investment. Profitable from day one, Shameless Media now has 11 staff.

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On the Sunday Life photo shoot in Sydney, the two friends’ support for each other is as obvious as it is genuine. Together, they discuss outfit choices and every comment from either woman about not being able to make a particular item of clothing work is enthusiastically refuted by the other.

The respect they have for each other is clear, and it’s why they work so well together. Since launching Shameless, their lives have been entwined.

Since meeting, they have been through break-ups, engagements and now weddings. When Andrews tied the knot with her long-term partner Mitchell Rees last December, McDonald was a bridesmaid. Now, McDonald is planning her own wedding, to partner Oliver Keogh, which will take place next year.

Years ago, when discussing when, or even if, they each wanted to have kids, it was a conversation they knew they needed to have not just as friends but as business partners.

“How do we do this and have a family if the whole business is relying on us showing up together at the same time?”

Zara McDonald

“I hate that we had to do this, but it was like, how do we have kids?” says McDonald. “How do we do this and have a family if the whole business is relying on us showing up together at the same time?”

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The only way to ensure it wouldn’t be an issue was to create a contingency plan. In their case, that plan involved expanding Shameless Media by growing the team and up-skilling junior employees. While neither Andrews nor McDonald sees kids in her near future, they found it reassuring to work towards a solution.

Regardless of the topic of conversation, whether it be personal or work-focused, the two try to be completely honest with each other. “We realised with every honest conversation we had, our relationship was so much better – it was far more intimate,” says McDonald.

The relationship McDonald and Andrews have with Shameless listeners is also based on trust. Their podcast episodes are meticulously well-researched, book recommendations are solid and the advice given via their Ask Shameless newsletter aims to always hit the mark.

Michelle Andrews wears 
Friends With Frank “Marlowe” blazer, $549, and “Sabine” trousers, $399. Veja shoes, $240, from Hype DC.

Michelle Andrews wears Friends With Frank “Marlowe” blazer, $549, and “Sabine” trousers, $399. Veja shoes, $240, from Hype DC.Credit: Hugh Stewart

In many ways, the relationship between Shameless Media and its audience is much like that between the friends. It began with a shared interest in celebrity gossip and TV shows, before moving into more personal recommendations of books and podcasts, until eventually reaching the stage where life’s most personal questions can be asked and answered.

Ask Shameless, which lands in more than 64,000 subscriber inboxes each Friday, answers reader questions about work, dating, friendship and more. The best of these advice columns have been published in a new book, 4am: Answers to the conundrums that keep you up at night.

Andrews and McDonald’s second book feels markedly different to their first, The Space Between. Published in 2020, it looked to explore the complications of life in one’s 20s.

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“We wrote it when we were so young,” reflects Andrews. “We truly had internalised this belief that for our words to be worthy of attention, they had to mine the deepest, darkest events that have ever happened to us.”

This feeling is one Andrews has spoken about before, referring to an essay she wrote for the book which included details of her sexual assault. “I wish I’d just saved that for myself,” she says, adding that while she wouldn’t take back the essay, she would take back some of the details.

Zara McDonald wears Luuda shirt, $390, and shorts, $290. Converse shoes, $130, from Hype DC.

Zara McDonald wears Luuda shirt, $390, and shorts, $290. Converse shoes, $130, from Hype DC. Credit: Hugh Stewart

Says McDonald, “If I was to psychoanalyse us, I’d say we felt guilty for having that platform that young.”

But that imposter syndrome is nowhere to be seen in 4am, in which Andrews and McDonald are happy to take their rightful place as agony aunts to young Australian women. In it, readers trust Andrews, McDonald and other Shameless columnists with their quandaries on everything from infidelity to sibling rivalry.

The book comes at a time when many young women have trust issues. TikTok is serving eating-disorder content to those already struggling, influencers and celebrities post undisclosed advertisements, and algorithms work to push everything from egg-freezing to injectables. Everywhere young women look, someone is making money off them.

Zara McDonald (left) wears Venroy mini dress, $200. Michelle Andrews (right) wears Venroy shirt, $280, 
and pants, $280.

Zara McDonald (left) wears Venroy mini dress, $200. Michelle Andrews (right) wears Venroy shirt, $280, and pants, $280.Credit: Hugh Stewart

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Only five per cent of the letters submitted to the Ask Shameless inbox are published. But after reading hundreds of requests for advice in the past three years, Andrews and McDonald are in touch with the most prevalent issues plaguing women today. One of those, says Andrews, is that “a lot of young women do not receive the basic level of affection, attention or love from their male partners”.

While there are questions the pair don’t feel qualified to answer yet – such as when to have kids – there’s also a kind of magic in the fact that Shameless listeners have access to McDonald and Andrews while they’re still in the thick of these struggles themselves.

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Building a brand on trust is both a big achievement and a risk. How worried are they about getting it wrong? Turns out, not very. Andrews and McDonald know what good advice looks like, and how to give it.

“I think the best advice is often not a statement – it’s a question,” says Andrews. “It’s listening to what someone’s dilemma is, then posing a question that helps them re-frame.”

As two women who are constantly being asked for advice, what are the questions they ask themselves?

“What’s the next thing?” says Andrews, without hesitation. “I’m constantly wondering, what’s the next show that isn’t out there.”

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McDonald is a little more introspective: “This will sound negative, but it’s actually not. I will constantly be asking myself: is this worth it?”

Building a business comes with weighty decisions and a huge amount of responsibility – as does catering to a big audience. According to McDonald, asking whether the stress is worth it not only ensures she’s looking after herself, it’s a constant reminder that yes, it is all worth it – for now. Until the answer to that question changes, McDonald and Andrews will keep shooting for the moon.

“We chose a route that has ended up being the most incredible path, but by far the most difficult path,” says Andrews. “But it’s the most rewarding, for sure. And it’s the best one for us.”

4am (Penguin Random House) by Michelle Andrews and Zara McDonald is out October 17.

Fashion editor, Penny McCarthy; Photographer, Hugh Stewart; Hair, Darren Summors using Oribe; Make-up, Annette Mckenzie; Fashion assistant, Jaya Prisco.

Stockists: Hype DC; Friends With Frank; Luuda; Venroy.

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Original URL: https://www.theage.com.au/lifestyle/life-and-relationships/is-this-worth-it-the-difficult-questions-the-shameless-founders-have-had-to-ask-each-other-20230926-p5e7sv.html