Sean Kelly & Michelle Elliott
Freelance AF
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 ser...
Author
Sean Kelly & Michelle Elliott
Category
Podcast website
Latest episode
Jul 7, 2026
Where to listen?
Podcasts in the app Replaio Radio Coming soonPodcasts are coming to the app soon. Install now and be the first to see a whole new take on podcasts
Episodes
Episode 16: Thanks, I Hate That Advice 07.07.2026 21:36
Have you ever been given unsolicited advice that made you want to launch the person giving it directly into the sun? Hey, us too! This week, Sean and Michelle are diving headfirst into the wild world of entrepreneurial advice, both the kind you ask for and the kind that gets dropped into your lap whether you wanted it or not. From productivity hacks and money mindsets to social media "must-dos" (S...
Episode 15: A Terrible Case of Comparisonitis 30.06.2026 26:35
Ever have one of those days where you're feeling pretty good about your business until you open social media and discover that apparently everyone else has doubled their revenue, launched a new offer, hired a team, bought a lake house, and achieved inner peace before breakfast? Amazing how quickly confidence can evaporate when you start comparing your behind-the-scenes footage to someone else's ca...
Episode 14: Still Somewhere Between Panic and Profit 23.06.2026 33:48
Last time, Sean and Michelle talked about the Messy Middle, that magical stage of entrepreneurship where you're successful enough to have problems, but not successful enough to hire someone else to deal with them. This week, they're answering the obvious follow-up question: how the heck do you survive it? From building systems and finding your people to redefining what progress actually looks lik...
Episode 13: Somewhere Between Panic and Profit 16.06.2026 22:19
You know that point where you’ve survived the chaotic beginning but still haven’t arrived at smooth, effortless success? Yeah, that one. The place where you've been grinding away for months (or years), wondering if you're making progress or just collecting new items for your stress-induced bingo card. This week, Sean and Michelle are diving into the Messy Middle; that stage of entrepreneurship whe...
Episode 12: No Name Tags Required 09.06.2026 25:06
We’re ba-aack! Like that one browser tab you swear you’ll get around to closing, your favourite freelancers have returned from hiatus. Are they refreshed? Debatable. Reinvigorated? Unlikely. Ready to share more questionably sound entrepreneurial advice? Absolutely. Does networking make your skin crawl? Does the phrase "elevator pitch" trigger your fight-or-flight response? Would you rather fake a...
Episode 11: Intentionally Different with Shantalle Gregory 12.05.2026 50:23
Hold onto your butts, Freelancers, because the interview we’ve been manifesting since last season is finally here. This week, Sean and Michelle sit down with Shantalle Gregory, owner of Pebbles and Pine, certified wonderful human, and quite possibly Freelance AF’s number one fan. Pebbles and Pine is a made-to-order apparel brand based in London, Ontario, built around belonging, inclusivity, and cr...
Episode 10: Viral Isn't The Flex You Think It Is 05.05.2026 31:45
Hey Freelancers! Remember when going viral was the dream? Yeah...we need to talk about that. Because as a small business owner, a viral post doesn’t automatically mean your inbox is blowing up with dream clients. Awkward, right? This week, Sean and Michelle are diving back into the socials to break down the difference between content that gets views and content that actually converts, and why post...
Episode 9: Confidently Competent 28.04.2026 25:20
Pop quiz, Freelancers: what actually makes you more successful, confidence or competence? Trick question! You need both. This week, Sean and Michelle are breaking down why being good at what you do isn’t enough if no one knows about it, and why confidence without the skills to back it up will only get you so far. Because let’s be honest: at some point in your business, you’ve probably been heavy...
Episode 8: Stop Taking It Personally 21.04.2026 27:26
Call us a broken record, because yep, we’re talking about social media again. That’s right, Freelancers; following up on our last episode, we’re diving into how to separate your marketing from your actual identity. Because when you are the boss, the marketing team, and the social media manager all rolled into one chaotic human, that line gets REAL blurry. One minute you’re posting content, the nex...
Episode 7: Sharing Ain't Always Caring 14.04.2026 28:02
Ever written a text or email in the heat of the moment and then thought, “Erm…maybe I shouldn’t send that…”? Yeah. This episode is for you. Social media’s been around for decades, and somehow we’re still figuring out how not to absolutely spiral on it. Sure, it’s a powerful tool for marketing and self-promotion, and yes, people want the real, relatable version of you. But there’s a fine line betwe...
Episode 6: Everywhere All at Once 07.04.2026 19:34
Freelancers, you should take this advice to heart… Yeah, Sean cringed a little, but that doesn’t make it any less true. The pressure to show up on every social media platform is real. And so is the guilt when you don’t. But trying to be everything, everywhere, all at once is a fast track to burnout. Trust us, we’ve been there. Here’s the good news: you don’t have to do it all. This business world...
Episode 5: Success Era 31.03.2026 20:54
Strap in, Freelancers; we’re about to get a little introspective. Think back to your baby adult era. We know, terrifying. But go with us. What did success look like back then? All cash and flash? Or did it already have a little more depth? Now fast forward to today. Where do your priorities actually sit? Is it still about chasing the bag, or has your version of success evolved into something with...
Episode 4: Build It or Bill It 24.03.2026 28:09
To DIY, or not to DIY…yeah, that’s the question. Because Freelancers, this one? It actually matters. Sure, doing it yourself can save you money, and when your margins are looking a little *ahem* humble, that’s a big deal. But on the flip side, hiring someone who actually knows what they’re doing can save you from expensive mistakes, mental breakdowns, and a few “why did I think I could do this?”...
Episode 3: What it Costs to be the Boss 17.03.2026 28:59
Buckle up, Freelancers, because today’s episode is all about cost. Don’t worry, you won’t need a calculator. We’re talking about what you give up to be a small business owner: things like winding down after hours, free weekends, and having a predictable social life. Of course, it’s not just about what you lose; it’s also about what you gain when you’re the one calling the shots. Think creative...
Episode 2: From Hot Mess to Progress 10.03.2026 20:04
Plot twist, Freelancers: we learned something! You know how people say hindsight is 20/20? This week, Sean and Michelle are strolling down Memory Lane, making a quick detour onto Reflection Avenue, and unpacking the biggest lessons from Season 1. Because here’s the thing: reflecting on what worked (and what absolutely did not) is one of the best ways to grow. Not just as a business owner, but...
Episode 1: Sassy B*tches Say What? 03.03.2026 24:13
Freelancers…we’re back! Season 2 of Freelance AF is officially in session and we’re coming in hotter, sharper, and slightly more self-aware. Double the strategy. Double the sass. Double the tangents. And we’re kicking things off with a spicy little word that most business owners are allergic to: no. Because saying yes to everything is cute, but it’s also how you end up exhausted, underpaid, a...
Episode 40: That's All Folks (For Now...) 25.11.2025 42:45
Holy moly, this week marks the Season 1 finale of the Freelance AF Podcast! Sean and Michelle are strutting down memory lane, spilling tea, and cackling their way through the highs, lows, and utterly unhinged tangents that made their very first season what it was. We’re reliving our favourite moments, discussing behind-the-scenes chaos, and handing out a few delightfully fake awards nobody aske...
Episode 39: Motivation Makeover 18.11.2025 43:47
Feeling tired, run-down, or like your motivation packed its bags and ghosted you? Good news; this week we’re serving up a full-on Motivation Makeover! Motivation might be our ride-or-die, but wow does it love to play hard to get. It’s not magic; it’s a muscle. And we’re talking how to grow it, flex it, and keep it from tapping out when life gets a little “nope.” Sean and Michelle are diving into...
Episode 38: Flag on the Play! 11.11.2025 49:22
This week on the Freelance AF Podcast, your favourite duo is lacing up their metaphorical cleats and diving headfirst into the world of red and green flags – and calling in a surprise new colour off the bench! From dream clients who make you wanna pop champagne to collaborators who make you wanna fake bad Wi-Fi, every interaction in business comes with its own set of signals. But here’s the kicke...
Episode 37: Advocacy in Bloom with Jodie Buttigieg 04.11.2025 59:44
Class is officially in session this week on the Freelance AF Podcast. And our teacher? The brilliant Jodie Buttigieg! Jodie’s the director and lead educator at Neubloom London, a neuro-affirming school shaking up the “one-size-fits-all” education system and proving that learning should actually fit the learner. She’s spilling the tea on what it really takes to build a school from scratch, the hi...
Episode 36: Spooktacular AF 28.10.2025 40:48
It’s that time of year when the veil is thin…and so are our boundaries when it comes to oversharing! We’re getting Spooktacular AF this week and digging up the skeletons in our freelance closets – the tricks we’ve learned, the treats we’ve earned, and the fears we’ve had to face in the dark corners of small biz life. Along with the usual unhinged rhetoric, Sean and Michelle are serving up chil...
Episode 35: Ghostbusters! 21.10.2025 34:03
This week on the Freelance AF podcast your favourite hosts are slipping on their proton packs and gearing up to battle every entrepreneur’s nightmare: ghosting. Ghosting is all-too common, with over half of Canadians saying they’ve been ghosted at least once in the past year. And for small businesses? Depending on the industry you’re in that could be even higher (think 60-70%). Whether you blam...
Episode 34: Dream Big or Go Home with Candice Neufeld 14.10.2025 1:02:24
This week on the Freelance AF Podcast, we’re kicking back with our girl Candice Neufeld; entrepreneur, coach, and literal ray of human sunshine. She showed up with good vibes, big dreams, and energy so contagious we’re honestly still rockin’ the high! Candice gets real about what it’s like to peace out of your biz’s physical space, and how sometimes walking away is actually the most badass move y...
Episode 33: Lost in Translation 07.10.2025 36:05
This week on the Freelance AF Podcast, your favourite freelancers are diving headfirst into the wild world of professional communication for the bold and scrappy small biz owner. Here’s the thing: the way you communicate says everything about how you do business. And let’s be real; some people (not Sean, nope, never Sean, absolutely not Sean…) get majorly turned off if your vibe isn’t hitting ri...
Episode 32: Talking to Ourselves...Again 30.09.2025 32:17
Do you hear that? Oh, it’s just us…Talking to Ourselves. Again. Yep, we’ve said this before, but some advice is too good not to put on repeat. These are the nuggets we wish we could whisper to our past selves when we were just getting started, whether that was 9 years ago or, let’s be real, 18 months back. This episode is jam-packed with the pep talk every entrepreneur needs: be patient, trust...
Similar podcasts
Replaio is not a podcast publisher; show names, artwork and audio belong to their authors and are distributed through public RSS feeds.