That Digital Take with Torri Webster

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 ex...

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 relationsh...

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 spe...

What if everything you thought you knew about PR was already outdated?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

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 ...

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...

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 top...

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 pan...

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 gues...

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 ...

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...

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...

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 ab...

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...

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 ...

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 h...

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 persona...

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...

✨ 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, ...