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From spreadsheets and Facebook ads to storytelling, studios, and a top-ranked business podcast.

In this special studio-recorded episode, Maggie sits down with her mentee, Alexander Whitfield, founder of Whitmedia Studios in Oshawa (Greater Toronto Area), ON, Canada, and co-host of the Hustle Over Everything podcast.

Alex shares how he went from running Facebook ads and staring at spreadsheets all day in corporate marketing… to building a purpose-driven media studio and a top-ranked business podcast that’s hit #1 in Jamaica and top 20 in Canada.

In this conversation, Maggie and Alex talk about:

• How a simple student project and curiosity about entrepreneurship evolved into a full podcast and then a studio
• The childhood “massage hustle” that hinted Alex was always meant to be an entrepreneur
• Why he walked away from corporate roles where his value felt tied only to performance metrics
• How podcasting lets him hear real stories, serve entrepreneurs, and “reward his inner child”
• The role mentorship played in uncovering blind spots, systems, and stronger foundations
• The fine balance between short-term “band-aid” fixes and long-term strategic solutions in business
• Practical tips for starting a podcast and then leveling it up with video, YouTube, and smart promotion
• His bigger vision for Whitmedia Studios, education, and workshops in storytelling, public speaking, and community building

If you’ve ever wondered whether it’s possible to build a business that feels meaningful, creative, and sustainable—not just profitable—this episode will inspire you to choose purpose over paycheque and design work that truly fits you.

Resources & Links

• Whitmedia Studios (Oshawa) – Podcast & media studio founded by Alex
• Hustle Over Everything Podcast – Alex’s entrepreneurship & culture podcast
• Connect with Alex on Instagram: @247hustler
• Book a complimentary consultation with Maggie - https://www.stairwaytoleadership.com/

Timestamps:

• 00:00 – Introduction & recording in a professional studio
• 00:40 – Meet Alex: founder of Whim Media Studios & Hustle Over Everything
• 01:20 – How a student project evolved into a podcast and then a studio
• 02:20 – Childhood “massage hustle” and early signs of entrepreneurship
• 03:30 – Maggie’s daughter’s nail business and TikTok success
• 04:00 – Why Alex left corporate marketing and Facebook ads
• 05:00 – Feeling disposable in corporate and craving purpose
• 06:00 – Maggie’s burnout story and losing her sense of purpose
• 08:00 – The beauty (and difficulty) of building your own business
• 09:00 – How mentorship supports entrepreneurs and reveals blind spots
• 11:00 – Maggie’s framework: when to fix problems now vs. later
• 13:00 – The origin story of Hustle Over Everything podcast
• 14:00 – Breakthrough moments: David Mullings, Jamaica, and Paul Brunson
• 16:00 – Posting daily: the challenge of a podcast-a-day for a month
• 16:30 – Advice for starting a podcast from scratch
• 18:00 – How to level up an existing podcast with video & YouTube
• 19:00 – Working with platform editors and podcast promotion
• 20:00 – Alex’s bigger vision for Whim Media Studios & workshops
• 21:00 – Upcoming workshop on public speaking, storytelling & community
• 21:40 – Where to find and follow Alex online
• 22:00 – Closing and thank you