That Digital Take with Torri Webster

Canadian fashion designer and entrepreneur Tanya Taylor joins host Torri Webster on That Digital Take to talk about the business of creativity and what it takes to build a fashion brand women truly connect with.

Since launching her namesake label in New York City in 2013, Tanya Taylor has built an internationally recognized brand. It’s known for vibrant colours, hand-painted prints and inclusive sizing, and it’s been worn by Michelle Obama, Beyoncé, Taylor Swift and Ariana Grande. In this episode, Tanya shares how she went from studying finance at McGill to fashion design at Parsons, what she l...

What does it really take to turn a great idea into a brand people love?

This week on That Digital Take, Torri Webster sits down with Lauren Levy, the co-founder of Odd Cookie Snacks, the Canadian snack brand turning bite-sized, crispy cookies into a nationwide business.

After building successful careers and businesses of their own, Lauren and Devin found themselves asking one big question: What's next? Their answer? Starting something completely new, together.

From launching in a single Toronto retailer to expanding into 800+ stores across Canada, we're getting into the realities of entrepreneurship...

Fall is officially here, and that means cancelling plans, getting on the couch and committing to something good.

This week on That Digital Take, Torri sits down at TIFF with Summer H. Howell and Alison Thornton, stars of Mike Flanagan’s Carrie on Prime Video. This new version of the Stephen King classic is set in high school today, with social media, group chats and viral moments. Summer (Carrie White) and Alison (Chris Hargensen) talk about:

Why are some creators landing $30,000 brand deals while others with bigger followings can't book a campaign? Sara Koonar, founder and president of Platform Media, one of Canada's leading talent management and influencer marketing agencies, reveals what's really happening behind the scenes. This week on That Digital Take, Sara pulls back the curtain on the business of the creator economy.

After a decade of building Platform alongside the industry, and launching Platform Social, Canada's leading influencer marketing conference, she knows exactly what brands and managers are looking for. In this episode:

What happens when a broken ankle turns into a global fitness empire? This week on That Digital Take, Michael Ramsey, co-founder and CEO of STRONG Pilates, shares how a frustrating recovery on the reformer sparked the idea for a workout with more strength and cardio, and how that idea grew from one Australian studio into an international brand with locations across Canada and around the world.

Michael gets honest about what it really takes to stand out in a saturated fitness industry, why the Pilates algorithm is such a volatile space, and what he makes of the...

Anna Lambe, award-winning actor, filmmaker and star of CBC/ Netflix North of North, joins That Digital Take for an honest conversation about what a working acting career actually looks like.

Anna opens up about wanting to give up "all the time," the black box of self-tapes and casting, and why the glitz and glamour people imagine around film and television doesn't match the job. She also gets into shooting North of North through three straight weeks of blizzards, working with Inuit showrunners from the North, how she memorizes a script, why Emma Stone is a guiding light...

It's been a while since a solo episode, so this is a proper catch-up, and it ends somewhere I wasn't expecting.

First: D23 as a first-timer. Sneaking onto the grounds early thanks to friends in high places, the celebrity sightings, and Disney laying out everything they have coming. Then one perfect day at Disneyland with Adam.

Then the main event, the bachelorette. Thirteen girls, planned entirely by me from January on: transportation, villas, menus, every moving part. JSX down to Cabo to meet the bachelor party, a welcome day at a villa that genuinely blew...

While Torri is off for Labour Day weekend, we’re pressing replay on a very special That Digital Take episode: Torri’s first-ever guest, best friend, and longtime content creator Jaclyn Forbes.

Before we’re back with brand-new episodes next week, revisit the conversation that helped kick off TDT’s guest era.

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Jaclyn Forbes has been creating online since the early days of YouTube — and in this episode, she joins Torri to unpack what it really takes to build a lasting career on the internet.

The best friends get into Jaclyn’s evolution as...

Most people in the creator economy build the audience first, then figure out what to sell. Mel Grauds did it backwards, and it worked.

Mel founded Melrose Training in 2020 with virtual classes, one-on-one clients and no following. Six years later she's running three Toronto studio locations, Yorkville, Rosedale and King West, plus virtual training and LIFT, her new small-group strength class. Along the way she's partnered with alo, Knix, Under Armour, Formula Fig, Revlon and Healthy Planet, and was chosen by Sporting Life to lead the official stretch at the Sporting Life 10K.

In this...

Mark Gaetano — Snarky Marky — is seven years into a career most creators don't survive two of. 4.9 million TikTok followers, 380 million likes, and he's doing it full-time from Toronto.

Host Torri Webster sits down with the creator behind the teacher POVs, the cafeteria monitor and "the volume inside of this bus is astronomical" to talk about what's actually changed in seven years — and what it takes to keep up.

Mark is refreshingly specific about the craft. When he started, a video was one continuous take, 15 to 60 seconds, no cuts. Now the hook is everything, and he explai...

Follower count vs. craft. The three things she looks for before hiring a creator. The contract and rights mistakes she sees over and over. And why brands will keep paying humans as AI-generated travel footage gets better.

Every travel brand is now expected to publish authentic creator content everywhere — social, paid, web, email, booking platforms, partner channels. Almost nobody built a content operation designed for that volume. CrowdRiff calls it the creator content supply chain problem.

Abby Yew, Head of Growth for Creators at CrowdRiff, joins That Digital Take to explain how they solved it: a...

Torri Webster goes inside the Ted Lasso Season 4 world premiere in Los Angeles with exclusive carpet interviews, plus a behind-the-scenes look at what covering a Hollywood premiere is really like.

This week on That Digital Take, Torri travels to LA with Apple TV+ for the world premiere of Ted Lasso Season 4, and this one's a hybrid episode.

First, exclusive conversations from the carpet with Hannah Waddingham (Rebecca Welton), Jeremy Swift (Higgins), and Juno Temple (Keeley Jones) about returning to the world of Ted Lasso, what fans can expect from the new season, and why the...

This week, psychiatrist Dr. Lesley Kirkpatrick joins That Digital Take to unpack why our brains won't switch off, and whether the same technology that helped create the problem can be part of the solution.

Dr. Lesley specializes in OCD, burnout, and Acceptance and Commitment Therapy, and is the founder of mindcomb, a psychiatry-led, audio-first wellness app built to support people between therapy appointments. She shares the story of building it, from spotting the gap in care to figuring out how a doctor becomes a tech founder, and where she draws the ethical line on what an app...

Sarah Nurse is one of the most recognizable faces in Canadian sport, a three-time Olympic medalist, Olympic gold champion, and record-holder for the most points scored in a single women's Olympic hockey tournament. Today she plays for the PWHL's Vancouver Goldeneyes while continuing to represent Team Canada on the world stage.

In this episode of That Digital Take, we go beyond the ice. Sarah became the first hockey player to front a major beauty campaign with Revlon and has built a thriving business as a content creator and entrepreneur, turning her athletic career into a personal brand...

Spin Master co-founder Ronnen Harary built a global entertainment empire, PAW Patrol, Bakugan, Air Hogs, and hundreds of toys that shaped childhoods worldwide, with, in his words, no experience necessary. In this episode of That Digital Take, host Torri Webster sits down with Ronnen to talk about his first book, No Experience Necessary, and the philosophy underneath the billion-dollar business.

This is less a conversation about toys and more about becoming: why inexperience can be a competitive advantage, why curiosity, wonder, and optimism are underrated superpowers, and why success is often more of an identity shift than...

Personal branding isn't about visibility, it's about legacy and leadership. This week on That Digital Take, host Torri Webster sits down with Taylor Buckley, founder of Golden Hour Collective, a social-first consultancy built to elevate female founders and entrepreneurs. With over a decade in social media, PR, and brand strategy, and appearances on Breakfast Television and Style Canada, Taylor breaks down where personal branding and the creator economy are actually headed next.

We get into why the internet stopped rewarding perfection and started rewarding authenticity and storytelling, whether audiences really trust creators less than they used to...

PR insiders Megan Taylor (SVP, Faulhaber Communications) and Rob Loschiavo (Partner, Pomp & Circumstance) return for PR 101, Part 2: the no-hedging, behind-the-curtain conversation on where PR and the creator economy really stand in 2026.

This week they get into the stuff most brands won't say out loud — why your relationship with a brand matters more than your follower count, how "different levels of access" can be built on purpose without making anyone feel like a second-class guest, and what earned media actually means today. Megan and Rob also break down how to launch a creator career from a standing start wit...

Before "content creator" was a real job, Nitsan Raiter was already building online. A decade later, she's grown an audience of hundreds of thousands, partnered with some of the world's biggest brands, founded the creator-education business Mind Your Business, and become one of Canada's most respected voices in the creator economy.

In this episode, Nitsan opens up about what it actually takes to build a sustainable creator career—and why followers alone were never the goal. We rewind to the early blogging days and her come-up alongside creators like Emma Leger and Sophie Suchan, then trace her ev...

Erica Hill rose to fame on Big Brother Canada, but in this episode of That Digital Take, she reveals how she turned reality TV exposure into a thriving full-time creator business, a loyal online community, and a sustainable career in the creator economy.

Erica gets refreshingly transparent about creator money, including why she publicly shared how much she earns as an influencer and content creator, the brands investing in queer creators, and the stigma around talking about income online. We dig into building a personal brand, navigating a public relationship, and her engagement to fiancée Cheyenne, p...

This week on That Digital Take, Torri kicks things off with a Summer Favourites segment covering the return of Love Island UK Season 13. From first impressions of the Islanders to early villa predictions, she shares why the reality series continues to dominate internet culture every summer.

Then, Torri sits down with viral food creator and creator economy expert Pushpek Sidhu. Known for his viral food rankings, internet debates, and highly recognizable content style, Pushpek shares how he built one of Canada's most recognizable creator brands and turned content creation into a thriving business.

Together, they...

What actually separates an iconic personal brand from one that just goes viral? This week on That Digital Take, host Torri Webster sits down with Jennifer Leigh, founder and CEO of Becoming Iconic, Editor-in-Chief of Iconic Magazine, business coach, and the brand strategist behind nine figures in sales.

Jennifer has helped countless women go from invisible online to completely undeniable, and in this episode she breaks down exactly how she did it. We get into defining what "iconic" really means in the creator economy, why she doubled down on launching a digital magazine while the rest of t...

We're on Crave! 🎉 This week kicks off in New York for the Dutton Ranch premiere and a stay at The Plaza, then it's off to San Francisco for a wedding, a trip into wine country, and an unforgettable F1 weekend in the Paddock Club — Disney-style. Behind all the glamour, though, this episode gets honest about something nobody warns you about when you go self-employed: how emotionally complicated business becomes when relationships are on the line.

The topic of the week is how to create win-wins in business, especially after conflict. The internet loves to romanticize "cutting people off,"...

The Creator Economy's Quiet Architect: Adam "Riv" Rivietz on Building #paid, $50M in Creator Payouts, and What Brands Still Get Wrong

What does it actually take to build the infrastructure behind the creator economy, not just talk about it? This week, I sit down with Adam "Riv" Rivietz, co-founder and Chief Strategy Officer of #paid, one of North America's leading creator marketplaces, and a Forbes 30 Under 30 honouree.

Riv has spent over a decade turning creator marketing from a "free product" side deal into a legitimate profession, with real payment terms, USD payouts, and tools built...

What if everything you thought you knew about PR was already outdated?

Ashley Orfus, founder of ALAB Group, left a high-profile career in luxury fashion and entertainment to build a communications firm designed for the way modern audiences actually discover and trust ideas. Over 13 years, she has helped category-defining brands across tech, food, hospitality, and culture do more than earn press, she helps them shape how their ideas are understood, adopted, and believed.

In this episode of The Digital Take, Ashley breaks down why traditional PR models are failing founders, what "performance-driven communication" actually looks...

What does a talent manager actually do, and what are creators completely getting wrong about the role?

This week on That Digital Take, host welcomes Kristen MacLellan, founder of Yesterday Agency, a Toronto-based talent and digital management firm she built from the ground up in 2021. Kristen has worked closely with creators, negotiated directly with brands, and built a sustainable business doing it which means she understands all three sides of the creator economy better than almost anyone. In this episode, Kristen pulls back the curtain on the creator-manager relationship: what managers do behind the scenes, how brand...

In this episode of That Digital Take, host Torri Webster sits down with Louise Upperton, sound meditation practitioner, somatic movement guide, Reiki practitioner, and Director of Programming, Partnerships & Content at Supernatural Toronto, to explore what it actually means to build a wellness life rooted in prevention, not reaction.

From breathwork and sound healing to cryotherapy, hyperbaric oxygen chambers, NAD+, and VO₂ Max testing, Louise unpacks the science and the intuition behind modern longevity, and why your nervous system is the foundation of all of it. They also go deep on The Portal at Supernatural, one of Toronto's mo...

Podcast consistency, creator growth, and the moment most people quit! That Digital Take hits 60 episodes and lands on iHeartRadio. In this milestone episode, host Torri Webster gets real about what building quietly actually looks like. Plus the London trip working with Robert Pattinson, hosting the Gillette Venus event, Coachella, life moving faster than you can process it, and an honest wedding planning confession.

This week's topic: The Quit Point — why most creators abandon their goals right before momentum hits, what the "quiet phase" actually builds, and how consistency compounds when no one is watching.

If yo...

What does it take to turn a childhood spent in a diamond shop into a thriving luxury jewelry brand? Jess Fried, founder of Toronto-based Dainty Diamond, joins That Digital Take to answer exactly that.

Jess grew up in her family's jewelry store, earned a Master's in Media and Journalism from Western University, built a career in media,  and then came full circle to found Dainty Diamond in 2020, right in the middle of a pandemic. Today, the brand is redefining luxury jewelry in Canada with custom gold pieces, permanent jewelry activations, and heirloom-quality designs built to be worn, no...

What happens when a viral country song gives you everything, and then you walk away from it?

Robyn Ottolini is the trucker's daughter from Uxbridge, Ontario who turned a TikTok moment into a platinum record, a Warner Nashville deal, and a spot opening for Shania Twain and Tim McGraw. Then she left her label, switched management, and quietly started over.

Out of that uncertain chapter came one scribbled notebook line — "I guess I'm growing down" — a home-recorded demo she posted with zero rollout strategy, and 20,000+ fan-made videos that followed.

In this episode, Robyn join...

What does it really take to build a brand people can't stop talking about, and can't stop buying from?

This week on That Digital Take, host Torri Webster sits down with Ashley Boyce, luxury brand strategist, former Unilever portfolio lead, co-founder of $12M DTC fragrance company Noteworthy, and now CEO of Zero Collective, for a masterclass in brand building at every stage of growth.

Ashley breaks down what nearly two decades inside the world's biggest CPG machine taught her that most founders never learn, why she walked away from billion-dollar budgets to bet on herself...

Brandi Leifso started Evio Beauty from a women's shelter at 21 with a bootlegged Photoshop. Now she's in 460 Shoppers Drug Mart locations and has a debut book. This is what Fearless Choices actually look like.

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What does it look like to build a globally recognized beauty brand from a women's shelter with nothing but a laptop and a borrowed idea? This week on That Digital Take, we sit down with Brandi Leifso, founder of Evio Beauty, impact entrepreneur, and author of the debut book Fearless Choices: How to Reclaim Your Power One Decision at a...

What if the hair you've always wanted could change the way you show up in the world?

In this episode of That Digital Take, host sits down with Natalie With-Seidelin, founder of the award-winning Brush Beauty Bar Inc. in Burlington and creator of Brush'd The Label, a luxury hair extension line known for its revolutionary Invisi-Weft method and ethically sourced Slavic K-Tips.

This isn't just a conversation about hair. It's about identity, confidence, and the psychology behind transformation.

We get into:

What does it actually take to build a fitness brand from scratch... no gym, no studio, just Instagram Lives and pure energy? This week on That Digital Take, we sit down with Toronto fitness founder Liv McIlkenny, the force behind Liv Sweaty, to talk about the real business of wellness, building community in the digital age, and what no one tells you about turning your passion into a paycheck.

Liv went from a 7-minute lockdown arm series on Instagram Live to full Zoom classes, park workouts, sold-out challenges, and one of Canada's fastest-growing digital fitness communities. Before...

Welcome back to That Digital Take

In Season 3, Episode 2, Torri Webster sits down with Jay McCauley, one of Canada’s most influential Gen Z leaders reshaping philanthropy, corporate strategy, and political engagement in the digital age.

Jay is a strategic communications advisor, philanthropic strategist, and changemaker who has:
• Helped raise over $20 million for community causes
• Served as the youngest board member in Canadian nonprofit history
• Advised CEOs, political leaders, and major nonprofit boards
• Built a reputation for bridging Gen Z culture with legacy institutions

This episode dives deep into Gen Z lead...

Welcome back to That Digital Take and welcome to 2026.

In this first episode of the year, I’m catching you up on where I’ve been, what this season of life looks like right now, and why the podcast is entering its next era.

January was supposed to be a mental reset… but somehow it turned into Miami slow living, early wedding planning, Vancouver film sets, Whistler influencer trips, and an Apple TV press day in LA brushing shoulders with the stars.

We’re talking:

✨ my “soft launch” into wedding era (engagement par...

In this Year in Review episode of That Digital Take, host Torri Webster reflects on the lessons, mindset shifts, and defining moments that shaped her life and career in 2025. From navigating growth in the creator economy to redefining success, boundaries, ambition, and self-trust—this episode is about what to hold onto, what to release, and how to move forward with intention.

This isn’t a highlight reel. It’s an honest breakdown of what worked, what didn’t, and the truths Torri is carrying into 2026.

✨ In this episode, Torri covers:

The biggest lessons learned in...

In this powerful episode of That Digital Take, Torri Webster sits down with beauty founder Haley Bogaert to unpack how makeup became more than just a career. It became a tool for healing, confidence, and rebuilding after profound personal loss.

Haley shares how developing a daily beauty routine during one of the hardest seasons of her life gave her structure, grounding, and a renewed sense of purpose. What began as a deeply personal ritual eventually evolved into a mission: helping others feel seen, strong, and confident through beauty.

We dive into:

How makeup...

From mixing DIY skincare in a kitchen to building one of Canada’s fastest-growing women-led beauty brands, this episode of THAT DIGITAL TAKE goes deep with Connie & Laura, co-founders of Three Ships Beauty.

In this candid, founder-to-founder conversation, we unpack how Three Ships Beauty disrupted the clean beauty and natural skincare space with transparency, science-backed formulas, and truly accessible price points. Connie and Laura share the real story behind bootstrapping the brand, raising ~$3.5M CAD in institutional funding, and navigating hyper-growth in a crowded beauty market.

We also explore the human side of entrepreneurship, including how...

✨ I’M ENGAGED! The FULL Behind-the-Scenes of Our Proposal, My Ring, and All the Sparkly Details ✨

This week’s episode is extra special, I’m finally sharing the entire behind-the-scenes story of my engagement. From how Adam planned the proposal, to my reaction, to the meaning behind my dream engagement ring, I’m taking you through every emotional, magical, sparkly moment.

If you love engagement stories, proposal planning, diamond details, ring shopping tips, or wedding content, this one is for you. 🤍💍

In this episode, I’m opening up about:
💍 How Adam planned the surprise proposal

How social media rewired our idea of modern romance!

This week on That Digital Take, Torri opens up about 10 years of love in the era of soft launches, hard launches, aesthetic romance, and algorithm-approved relationships. We’re diving deep into how social media has completely reshaped modern love, and what a decade-long partnership really looks like when your career lives online.

From the pressure to curate picture-perfect moments to the rise of relationship comparison culture, this episode breaks down the realities behind the aesthetics—and the unexpected ways content culture can strengthen (or strain) your conn...