Freelance AF

By: Sean Kelly & Michelle Elliott
  • Summary

  • 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
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Episodes
  • Episode 9: A Day in the Life
    Apr 22 2025

    Guess who's back to spill the entrepreneurial tea? Sean and Michelle are pulling back the curtain and letting you sneak a peek at what really goes down in the wild world of boss life. Spoiler: it's way more than just vibes and vision boards.

    Think freelancing is just chillin’ in your PJs, sippin’ mimosas while the money magically appears? We wish! Our hosts kick off their days with caffeine, obviously! Then Michelle’s breaking a sweat while Sean’s off channeling his inner spa day. After that, it's go-time: emails, social media deep dives, and big-brain biz ideas. Sprinkle in some serious skill-stacking - Sean’s all about that "liquid learning" while Michelle’s earning her degree from YouTube U. Throw in photoshoots, tasting events, admin days and voilà! they’ve officially outworked your average 9-5. Freelance AF? More like Fierce And Full-time.

    This week's cider pour is Porter's Perfection from our homegrown hero, Heeman's Cellar, right here in good ol' London, Ontario!

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    38 mins
  • Episode 8: Mythbusters
    Apr 15 2025

    Throw on that lab coat, grab your safety goggles and get ready to bust some myths, freelancer style! This week, your fabulous neighbourhood hustlers are channeling their inner MythBusters – sorry, no Bigfoot or aliens here (though we’re not ruling out intergalactic side gigs). That means diving into the wild, wacky world of entrepreneurial myths. You know, the kind people love to whisper about behind their lattes, and, even more dangerously, the ones entrepreneurs believe about themselves.

    Think you have to be rolling in dough, grinding 24/7, or under 30 with a ring light to make it? Think again. Sean and Michelle are calling BS on those tired clichés. They’re breaking it all down, from the “I must do everything myself” delusion to the “success should be instant” fantasy. And don’t even get them started on the obsession with social media followers.

    Believing a myth now and then? Totally human. Letting it steer your business? Major red flag. Stay sharp, freelancers – these streets are no joke, but with the right mindset (and a handful of sass), you’ve got this!

    This week’s pour is Reif Estate Winery’s Drea’s Dornfelder, a deliciously smooth and fruity red wine from Ontario’s Niagara wine region!

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    39 mins
  • Episode 7: Community Totally Slays Competition
    Apr 8 2025

    Oh, it's that time again! Your favourite freelancer squad is back at it, sipping cider and throwing down the real talk about community vs. competition.

    After Sean gives Michelle a lesson in "equidistant" (yep, it’s a word), and Michelle takes a victory lap for being the only one who did the homework, the hosts dive into the juicy stuff – why building a solid community of fellow entrepreneurs is EVERYTHING. We’re talking real, no-strings-attached connections, endless support, and finding those ride-or-dies who vibe with your values. Plus, they get real on how even a simple social media interaction or client referral can make a world of difference for a small biz, and how sticking together is the secret sauce to leveling up. Strength in numbers, baby!

    So grab a zesty drink, kick back, and let’s get into how Community Totally Slays Competition!

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    22 mins
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