Sydney Robertson is a media industry veteran with over 20 years of experience leading high-performance sales teams at Twitter (now X), Google, AOL, and Yahoo. Currently a Video Partner Lead at Google, she is also the co-founder of Element, an organization dedicated to empowering women to invest and lead global change.

Sydney joins the podcast to discuss the reality of a non-linear career path. She opens up about moving from a traditional law background into the fast-paced world of digital media and shares her firsthand experience managing a team during the volatile Twitter acquisition and mass layoffs.

00:00 - Intro

04:58 - Inside the Twitter acquisition & layoffs

05:56 - Stepping up when leadership disappears

07:33 - Why you need to avoid Toxic Positivity

09:26 - Adapting to rapid changes at X Corp

11:16 - Creating mentorship opportunities for women

17:30 - How early-stage founders can get funding

19:19 - Letting go of external validation

21:25- Why rejection is actually redirection

Healthcare CMO Daniel Shearer reveals how Maple became Canada's #1 virtual care platform - and why Canada's aging population crisis demands urgent innovation in how we access medical care. From leading iconic campaigns like SickKids VS to scaling a healthcare startup, Shearer shares hard-won lessons on customer obsession, culture preservation, and building brands that solve real problems.

00:00 - Intro

00:49 - From Agency President to Healthcare CMO: Daniel's Journey from Cassette, Working with Google & SickKids, to Joining Maple as a Consultant Who Stayed

04:14 - Inside Maple's 10-Year Journey: The Three Founders' Story, Brett the Doctor-Consultant, Building Culture & Making Space for New Executive Voices

09:16 - Real Customer Impact Stories: Saving Trips to SickKids, 3AM Appointments, Doctor Shortages & How Maple Relieves Pressure on Canada's Healthcare System

12:01 - How Maple's Two-Sided Marketplace Works: The Genesis Story, Uber for Doctors & Patients, Not Hiring Doctors Out of the System & Managing Thousands of Providers

15:45 - Creating the Iconic SickKids VS Campaign: Making Kids the Heroes, When the Doctor Wanted It on His Scrubs & Raising $1.7 Billion by Disrupting Nonprofit Marketing

21:10 - Scaling Culture Without Breaking It: The 150-Person Rule from Taxi 2, Remote Teams, Rewriting Values in New York & Why "We Are a Team" Works Everywhere

28:20 - Marketing Healthcare Technology: Benefits Over Features, Customer Obsession Philosophy, Learning from Wealthsimple & Greenhouse & Why Users Don't Care About Your Algorithm

32:48 - Beyond Maple: Board Chair of The Bentway, G Adventures, The Power of BHAGs & How "End Poverty Through Tourism" Guides Every Single Decision

38:44 - Advice for Entrepreneurs & Founders: Solve Real Problems Not Fake Ones, Delight 100 People First, Don't Dilute Your Core Idea & The Right People Make Everything Work

43:03 - The Future of Canadian Healthcare: Staying in Canada For Now, Global Expansion Potential, The Demographic Pyramid About to Flip & Why the Next 20 Years Are Urgent

46:30 - Where to Find Maple: GetMaple.ca, App Store, 1.7 Million Five-Star Reviews & Creating More "Maple Aha Moments"

Jackie Prince shares how she built Guests on Earth from pandemic idea to retail success. Female entrepreneur tips, fundraising advice, DTC brand strategy, and work-life balance for moms in business.In this episode of Beyond Four Walls, host Natasha Penzo sits down with Jackie Prince, founder of Guests on Earth, a Toronto-based sustainable cleaning brand redefining the home care industry. From her background in brand strategy at agencies and TikTok to launching a product-based business with zero experience in chemistry or manufacturing, Jackie's entrepreneurial journey is packed with lessons for aspiring founders.

0:00 - Intro5:39 - Designing the brand and packaging11:38 - The reality of entrepreneurship and growth challenges14:39 - Evolving as a founder while scaling18:59 - Managing business and motherhood21:47 - Advice for aspiring entrepreneurs24:52 - Morning routines and daily life26:06 - Launching the laundry detergent line28:22 - Final Thoughts

In this episode of Beyond Four Walls, Natasha & Gabrielle sit down with Steph Gee, partner at Gee Beauty—the multi-generational beauty destination and product line with studios in Toronto and Miami. We talk about building a family business, the operations + HR systems behind a high-touch brows, facials, and makeup studio, and how the team keeps every touchpoint cohesive while expanding. Steph shares recruiting and onboarding lessons (no gatekeeping), why over-communication preserves brand standards, and how setting boundaries actually creates room for team growth.We also get into product development for Gee Beauty’s skin prep line—primers, eye care, a new mist—and how the brand balances retail partnerships (Nordstrom US, Holt Renfrew Toronto) with an in-studio, community-first model. Plus: Steph’s morning routine, faith, content workflow, and what’s next for Toronto & Miami studio expansion.

In this episode of Beyond Four Walls, host Natasha Penzo sits down with Ally Mamalieder, President and second-generation founder of Organic Traditions. We cover her leap from corporate communications to leading the family business, the rebrand (what to keep vs. evolve), and how she turned single-ingredient superfoods into everyday blends people actually use.

Ally breaks down “blends over trends” product strategy, tips for kid-friendly smoothies, and the brand’s push into U.S. retail while scaling e-commerce. We also get raw about motherhood + entrepreneurship, training for 29029, hitting 100KM after injury, and the mindset shifts that power founders through setbacks.

00:00 Intro01:23 Leaving corporate → joining family business04:28 From ingredients to blends + rebrand challenges08:50 Founder wellness, motherhood & leadership11:09 Trends vs efficacy + superfoods for kids14:19 Retail growth in Canada & U.S. expansion16:16 Signing up & training for 2902920:29 Community, resilience & mindset lessons24:59 Day 3 injury, 100KM pivot & business parallels32:08 Biggest takeaways + what’s next for Organic Traditions

Choosing the right school for your child can be really stressful, especially after everything families have been through in recent years. In this episode, Natasha talks with Jessica Diamond, founder of Diamond Education Consulting, about how to make school decisions easier and more thoughtful.

Jessica has worked in education for over 16 years, and now helps families figure out what kind of school is the right fit, public, private, or something in between. She shares practical advice on what to look for in a school, how to prepare for interviews, and what really matters when it comes to helping kids succeed.

https://www.instagram.com/beyondfourwallspodcast
https://www.instagram.com/thehomekin
https://www.instagram.com/thepenzoteam
https://www.instagram.com/urban_blueprint

00:00 Intro

05:12 Learning struggles after COVID

06:08 Common mistakes parents make

09:03 When to start looking at schools

10:27 Do kids need to start early?

11:22 Why switching schools isn’t always bad

13:59 What to expect in private school interviews

18:08 Is private school really better?

19:45 How to get help in public school

21:35 What an education consultant does

26:54 Final thoughts

Kate Taylor Martin didn’t set out to be an entrepreneur. But when her work in hospitals opened her eyes to a broken food system, she followed a calling into holistic nutrition and eventually launched Nutbar, a superfood café rooted in quality, care, and healing.

In this episode, Kate shares how she opened Nutbar while pregnant with her first child, scaled her business through COVID, and stayed grounded in her values while building a growing wellness brand. She talks candidly about what real leadership looks like, how her morning routine keeps her regulated as a mom of three, and why “filling your cup” isn’t just a metaphor....it’s her business philosophy.

👉 Follow Nutbar: @nutbar.co

📌 Penzo Group:
https://www.instagram.com/beyondfourwallspodcast
https://www.instagram.com/thehomekin
https://www.instagram.com/thepenzoteam
https://www.instagram.com/urban_blueprint

00:00 Intro

07:11 Creating a Superfood-Focused Menu

13:07 Naming and Trademarking 'Nutbar'

20:11 Soft Power and Heart-Centered Leadership

27:04 Kate’s Wellness Routine as a Working Mom

34:59 Wellness Myth-Busting

36:18 Where to Find Nutbar

Hana James co-founded Greenhouse Juice Co. and turned a single Toronto shop into one of Canada’s most iconic wellness brands. In this episode, she shares how she built a multi-million dollar business while staying true to sustainability and health.

We talk about what it really takes to start a wellness brand from scratch, the truth about “healthy” juice, scaling a company without selling out, and how Greenhouse became a household name — one glass bottle at a time.

🔗 Learn more: https://greenhouse.ca
📸 Follow Greenhouse: @greenhousejuice

—

💫 Follow the Penzo Group:
@beyondfourwallspodcast
@thehomekin
@thepenzoteam
@urban_blueprint

00:00 Intro04:08 Building a Health-Conscious Brand08:32 Expanding Nationwide and Beyond12:37 Innovations in Juice Production15:35 The Founders' Unique Skillsets17:52 Building a Strong Team28:23 Incorporating Wellness at Home

Anna Morrison left a high-stress career producing luxury photo shoots to start something that brought her and others closer to what matters: time, connection, and unforgettable travel memories with family.

She’s the founder of AM Travel, a luxury travel business that curates personal, meaningful trips for families and individuals looking to enjoy the world without the overwhelm of planning it all.

In this episode, Anna and Gabrielle explore:

• Why parents shouldn’t be afraid of long flights or kid-friendly adventures

• The biggest misconception about luxury travel (especially with kids)

• The truth about “TripAdvisor overload” — and how to avoid it

• How to build trips around your stage of life, not just your dream board

• Why Canada deserves a glow-up on the global travel map

🌐 Learn more at amtravel.ca

💫 Follow the Penzo Team:

• @beyondfourwallspodcast

• @thehomekin

• @thepenzoteam

In this episode of Beyond Four Walls, Gabrielle Chapman sits down with Olivia and Luca Penzo to discuss their journey of transforming their home into a family sanctuary. They share their insights on renovation planning, making bold design choices, and balancing family life during the construction process. They reflect on their neighborhood's charm and offer advice to families facing similar decisions about staying, renovating, or moving. Tune in to hear about their inspiring story, thoughtful design solutions, and what makes a house truly feel like home.

Stay connected with all things home, design, and wellness by following:

• The Penzo Team: @ThePenzoTeam

• Urban Blueprint: @Urban_Blueprint

• Homekin: @TheHomekin

If you enjoyed this episode, don’t forget to follow, download, and subscribe on your favorite podcast platform. Leave us a review and share your thoughts—it helps others discover the show! Catch video highlights and full episodes on YouTube, and make sure to like, comment, and subscribe to our channel for more inspiring conversations.

Thank you for your support, and we’ll see you next time on Beyond Four Walls!

00:00 Intro

03:58 The Big Move and Major Renovations

14:00 Design Choices and Inspirations

21:07 Navigating Renovation Challenges