Freelance AF Podcast By Sean Kelly & Michelle Elliott cover art

Freelance AF

Freelance AF

By: Sean Kelly & Michelle Elliott
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About this listen

Freelance AF is a cheeky peek behind the curtain into the world of being your own boss! Join freelancing friends Sean Kelly (owner and founder of Barrel to Basket, a wine and cider tasting event company) and Michelle Elliott (professional brand photographer, and owner and founder of MEE Photography) as they dive into the nitty gritty of owning a small business. These intrepid hosts cover a range of topics - like crucial steps to starting your own business, the importance of developing your brand, and how to stay organized - all while laughing and drinking, and never taking themselves too seriously. From the corporate world to becoming entrepreneurs, Sean and Michelle share their successes and struggles to help you find your own path to freelance freedom. Whether you're an established business owner, or just starting on your journey, their hope is to impart some semblance of wisdom on you - or at the very least show you what NOT to do! Episodes release weekly and occasionally feature guest interviews with friends and fellow business owners.

So hand in that key card and hit 'send' on your sassy resignation letter, and prepare to be Freelance AF!

Copyright 2025 Sean Kelly & Michelle Elliott
Economics Leadership Management & Leadership
Episodes
  • Episode 20: Bakes for the Memories with Karna Brennan
    Jul 8 2025

    Hope you're hungry, because this episode is baked to perfection!

    This week, your fave podcast duo is serving up something extra sweet with Karna Brennan of the oh-so-fabulous Brennan Baking Co. Karna’s spilling the (brown) sugar on baking the treats people actually crave, sharing family recipes, and finding that cozy, magical joy in homemade pies. We’re also getting into the juicy stuff, like hitting the sweet spot in business growth, the perks of being your own boss, and why there’s truly no place like home (especially if it smells like cookies).

    Oh, and did we mention? Karna brought the baked goods. And Sean, being the overachiever he is, paired them with cider. Four of ‘em, to be exact! As Michelle wisely puts it, the way to our hearts is through our stomachs...so basically, we’re in a committed relationship now.

    This special episode features the following totally drool-worthy Ontario ciders - Thornbury Craft's Wild Blueberry and Elderflower Cider, Heeman's Cellar's Strawberry Rhubarb Cider, Lost Craft's Apple Cider, and Shale Ridge Estate Winery and Cidery's Peach Apple Cider!

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    1 hr and 6 mins
  • Episode 19: Canada Day, Eh Eff
    Jul 1 2025

    O Canadaaaa… you better believe we’re celebrating!

    It’s Canada Day, and your favourite Freelancers are raising a glass (not a double-double) to the Great White North with a proudly semi-accurate dive into some fun Canadian business facts! From oddly American-sounding company names to a shocking number of world-changing inventions, we’re spilling the maple tea on what makes our biz scene so iconic.

    Regardless of our factual accuracy, one thing’s crystal clear: Canadian entrepreneurs are tough, creative, and full of grit – and we’re so here for it.

    So a very happy Canada Day to all, and remember that the amazing people who live here are what’s truly great about our country.

    This week’s pour is Muskoka Lakes Farm and Winery’s super tart and delicious Cliff Jump Cranberry cider, made in Bala, Ontario!

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    29 mins
  • Episode 18: Proud AF (and Older, too)
    Jun 24 2025

    It’s a glitter-soaked, confetti-filled kinda week on the podcast as your favourite Freelancers throw a double celebration: Pride Month and Sean’s birthday!

    That’s right, Sean’s another year older (but no wiser), and Michelle’s putting him in the hot seat with all the hard-hitting questions. Like which Fab Five member does he emulate? What really matters when you're celebrating your birthday? And how has being a gay man shaped his journey as a boss-level biz owner?

    Spoiler alert: it’s all about leading with love, embracing your sparkle, and never saying no to glitter, especially on your birthday.

    So pour yourself something strong (because hydration is cute, but cocktails are cuter), throw on that feather boa, and join us for laughs, honesty, and a whole lotta Proud AF energy.

    This week’s pour is Loch Mór Cider Co.’s Sour Cherry Cider, from Prince Edward County! This cider was a recent winner at the 2025 GLINTCAP Awards!

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    30 mins
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