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 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 the industry pivoted away from media, and the #1 mistake she sees women make when building a personal brand online.

We also dig into the line between authentic self-expression and strategic brand building, how to stand out in a saturated coaching and creator niche, rewiring your relationship with money and pricing your worth, and her honest day-one advice for anyone starting with zero following and zero budget. Plus a rapid-fire round, Instagram vs. LinkedIn, overrated business advice, best investment in her own brand and a custom "Iconic or Not Iconic" lightning round you'll want to hear.

If you're a founder, creator, coach, or marketer building a brand online, this one's a masterclass in visibility, personal branding, and turning attention into actual business growth.

🎙️ That Digital Take with Torri Webster, now on iHeartRadio, Apple Podcasts, and Spotify. New episodes every Monday.

Topics covered: personal branding · building a brand online · creator economy · women entrepreneurs · digital magazine · business coaching · personal brand strategy · visibility · pricing your worth · Instagram vs LinkedIn · founder mindset · content strategy

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," "protecting your peace," and "removing toxic people" — and there's truth there. But real business asks for something harder: negotiation, emotional regulation, compromise, and the ability to separate intent from impact. The strongest people aren't the ones who avoid conflict; they're the ones who navigate it without turning every disagreement into a war.

We also get into ego management (because most conflict escalates when both people just want to be right), why long-term thinking beats emotional reactivity in creator culture, and the personal vision exercise that's been reshaping how I lead and connect. My challenge to you this week: find one place in your life or business where you can create a win-win — and share it with a friend.

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 from the ground up. #paid has now paid over $50 million to creators, and Riv has been evangelizing the space globally since before most brands knew what an "influencer" was.

In this episode, we get into all of it: the difference between influencers and creators (and why it matters), the Virgin Voyages x TikTok creator cruise that generated 108 million views, the Creator Calendar and why brands are now "upfronting" life milestones like weddings and pregnancies, what the 2026 Creator Signals Report reveals about shifting content trends, and how AI is reshaping every layer of the industry.

We also talk about what it's like to be a founder who's not the CEO, why Riv is also an ordained minister and children's book author, and what he'd whisper to any founder entering this space today.

Topics covered: Creator economy infrastructure · Brand education · Creator-first payment models · Forbes 30 Under 30 · Creator Calendar · Swan Beauty viral moment · AI and synthetic influencers · First-party creator data · Founder life post-Series B · The future of #paid

Connect with Riv: [#paid / LinkedIn / Instagram @hashtagpaid]

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 like in practice, and how brands can cut through the noise in a world drowning in content.

In this episode, we cover:

• Why press hits and impressions are the wrong metrics to chase
• How to introduce a product or idea people don't have a reference point for yet
• Why influencers should be treated as co-creators, not distribution channels
• The danger of over-indexing on founder-led content (and when to create distance)
• How AI is making communications more human, not less
• What to do when you have no budget and everything to prove

Whether you're a founder shaping your first narrative, a marketer rethinking your PR strategy, or a brand trying to build genuine trust online — this episode will change how you think about communications.

Connect with Ashley Orfus: [ALAB Group]

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 deals actually get made, and the very real ways creators are leaving money on the table right now.

She also gets honest about what makes a creator genuinely bookable in 2025 — and it may not be what you think. What you'll learn in this episode: → The real role of a talent manager (and what it's NOT) → How brand partnerships actually get negotiated → Why creators consistently undervalue themselves — and how to fix it → The subtle red flags that make managers and brands walk away → What makes a creator easy to sell to brands right now → How AI is changing contracts, negotiation, and strategy → Setting competitive rates — is there a real benchmark? → What types of creators will win over the next 1–2 years

Plus: a rapid-fire round covering the most overrated creator metrics, underrated revenue streams, and whether vloggers are actually making a comeback. Whether you're a creator looking to level up your brand partnerships, or just curious how the business side of the creator economy really works, this one is packed. Subscribe to That Digital Take wherever you listen to podcasts.

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creator economy, talent management, brand deals, influencer marketing, digital strategy, Toronto creators, content creator, tips podcast

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 most talked-about wellness spaces, and what it looks like when high-performance biohacking meets embodied, soul-led practice.

Whether you're deep in your wellness journey or just starting to ask bigger questions about your health, this conversation will shift how you think about your body, and what feeling well can actually look like.

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 you've ever thought "is this even working?" — this episode is your answer.

Topics: podcasting milestones, content creation, creator economy, staying consistent, iHeartRadio, digital media growth, hosting events, work-life balance

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, not stored.

In this episode, we get into the rise of permanent jewelry, why dainty gold layering has taken over (looking at you, Sabrina Carpenter), the quiet luxury aesthetic, women buying their own fine jewelry, and what record gold prices actually mean for shoppers right now. We also tackle lab-grown vs. mined diamonds, the vintage jewelry resale boom, and why the best jewelry is the kind you never take off.

Plus, Jess gives her honest advice to anyone shopping for an engagement ring, and we close it out with a rapid-fire round you won't want to skip.

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 joins host Torri Webster to talk about the catch-22 of breakthrough success, what it actually felt like to go independent, and why the demo version of a song sometimes hits harder than the polished studio cut. The full studio version of "Growing Down (Into The Roots)" is out March 20th, and Robyn performs at the JUNO Kickoff Concert in Hamilton on March 26th.

We get into:
• Why "F-150" was both the best and worst thing that ever happened to her
• What "growing down" actually means — and why she thinks it's better than growing up
• Posting a raw, unproduced demo and watching it explode
• Leaving a major label and rediscovering her creative identity
• Turning 30, writing confessional country, and building a career entirely on her own terms
• Her relationship with TikTok, algorithms, and staying authentic in a changing industry

If you've ever felt like you were chasing a version of success that didn't quite fit — this one's for you.

🎵 "Growing Down (Into The Roots)" — out March 20
🎤 JUNO Kickoff Concert, Hamilton — March 26
🎧 Follow Robyn Ottolini: https://www.instagram.com/robynottolini/ 

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, and the real reason DTC isn't dead, it just grew up.

In this episode, we get into:

• The mindset shift from corporate marketer to founder (and why your instincts can work against you)
• How she scaled Noteworthy to $12M+ and what she'd do differently today
• What "luxury" actually means in 2026 — and why the word is dangerously overused
• Whether Instagram and TikTok can build real premium brands, or slowly kill them
• The truth about influencers: are they elevating luxury or quietly diluting it?
• How Zero Collective is carving out a niche in fashion without the designer price tag
• The JFK Jr. / Carolyn Bessette Kennedy nostalgia wave — and how to manufacture desire in an algorithm-saturated world
• What separates the brands that scale past $1M, $5M, $10M from the ones that stall

Plus, a rapid-fire round on DTC vs. retail, TikTok vs. email, AI in marketing, and the one brand actually doing luxury right in 2026.

Whether you're a founder, a marketer, or a brand-obsessed creative, this one is packed with the kind of strategic thinking that usually stays in the boardroom.

🎧 Listen now and subscribe so you never miss an episode of That Digital Take.

luxury branding, DTC marketing, brand strategy, founder story, fashion marketing, Unilever, fragrance brand, premium brands, digital marketing 2026, brand building, consumer goods, TikTok marketing, influencer marketing, CEO interview, Canadian entrepreneurs, Zero Collective, Noteworthy, Ashley Boyce