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Stacy Maynard — Co-Founder TLMA · Speaker · Operational Architect
Co-Founder & COO · Speaker · Operational Architect

Stacy
Maynard

Fay had the vision. Stacy built it. The Co-Founder and COO behind Too Late My Ass™ — and the operational architect who turns great ideas into scalable, running reality.

Book Stacy to Speak
Stacy Maynard — Co-Founder TLMA, Speaker, Operational Architect
BSc · Dalhousie University Certified Professional Speaker Speaker of the Year CEO · City Media Group
The Story Behind the Work

She turned a crisis into
a superpower.

When Stacy's son was diagnosed with autism, everything changed. The systems she'd spent years building for other people's businesses suddenly became personal — a framework for navigating a world that wasn't designed for how her family lived. She learned, with absolute clarity, that the right architecture changes everything.

That experience became the lens through which she built a 15-year career helping hundreds of entrepreneurs, creators, and organizations build the machine behind their vision. Production systems. Content workflows. Speaker programs. Digital platforms. Not just what launches — but what actually scales.

In 2022, Fay Chapple had the vision for Too Late My Ass™. Stacy made it real. As Co-Founder and COO, she built the operational infrastructure, the tech stack, the content systems, and the production workflows that transformed a bold idea into a global reinvention ecosystem serving thousands of people 50+.

"I take visions and make them operational. I build what scales — not just what launches."

Her background in Psychology and Sociology (BSc, Dalhousie University) makes her unusually effective at this work. Tech overwhelm, content paralysis, visibility fear — she recognises these not as tactical problems but as identity problems. And that distinction changes everything about how you solve them.

The Work

Two companies.
One mission.

Too Late My Ass™ — Co-Founder & COO

Stacy leads the operational infrastructure behind TLMA's entire ecosystem — the Inner Circle membership, podcast production, content engine, tech stack, and the challenge and launch systems that run week over week without burning anyone out.

Inside the Inner Circle, she leads the Tech Implementation Lab — a dedicated training system that removes tech fear from midlife creators so they can actually execute on their second act. She also co-hosts the TLMA Backstage members-only podcast series alongside Fay.

City Media Group — CEO (Founded 2011)

For over 15 years, Stacy has worked with thousands of business owners — through courses, masterminds, and one-on-one coaching — helping them build content systems, podcast infrastructure, and digital platforms that actually hold.

City Media Group specialises in podcast production, digital media strategy, and systems training for entrepreneurs and organisations ready to scale their content presence without the chaos.

Areas of Expertise

The reinvention expert
people over 50 actually need.

While Fay provides the strategy and direction, Stacy provides the architecture. Together, they cover every dimension of the second act — from identity and neuroscience to implementation and infrastructure. Stacy's speciality is making transformation not just inspired, but operational.

Operational Strategy & Systems

Building the infrastructure behind reinvention at scale. From content engines and membership operations to tech stacks and launch systems — Stacy designs systems that sustain transformation long after the inspiration has worn off.

Podcast Production & Digital Media

As producer of the Too Late My Ass™ podcast and CEO of City Media Group, Stacy has built and scaled content systems for hundreds of creators. She trains entrepreneurs and organisations on podcast production, digital confidence, and visibility strategy for second-act professionals.

Tech Implementation for 50+

Tech overwhelm is an identity problem, not a technical one. Stacy's Tech Implementation Lab inside the TLMA Inner Circle removes the paralysis and replaces it with a working system — one skill, one tool, one win at a time.

Autism Advocacy

Stacy is a committed advocate for families navigating autism — drawing on her personal experience raising a son with autism to speak to the intersection of identity, resilience, and the systems thinking that transforms challenge into capability.

Keynote Speaking

A certified professional
speaker of the year.

Stacy Maynard is a Certified Professional Speaker and Speaker of the Year who brings the same operational precision to the stage that she brings to every system she builds. Her keynotes are practical, strategic, and built for audiences who are done being inspired without being equipped. She speaks globally on operational strategy, digital confidence, podcast production, and the systems behind sustainable transformation.

KEYNOTE 01
The Architecture of Change: Building Systems That Actually Stick
Why most transformations fail — and the operational framework for building change that lasts beyond the initial inspiration. For organisations serious about sustainable results.
Keynote · 45–60 min · Workshop available
KEYNOTE 02
Scaling Without Burning: Operations for the Second-Act Entrepreneur
The systems, structures, and operational intelligence that let entrepreneurs and small teams build movements without burning out the people running them.
Keynote · 45 min · Entrepreneurship & small business track
KEYNOTE 03
Your Podcast, Your Platform: Digital Confidence for the 50+ Creator
How second-act professionals can build a podcast and content presence that establishes authority, grows community, and creates income — without the tech overwhelm.
Keynote · 45 min · Podcast, media & creator tracks
KEYNOTE 04
Behind the Movement: Building Too Late My Ass™
A case study in co-founding a reinvention movement — the operational decisions, technical architecture, and strategic frameworks behind TLMA and The Long Game app. Best delivered as a joint keynote with Fay Chapple.
Keynote / Fireside · 30–45 min · Joint presentation available
Certified Professional Speaker Speaker of the Year Author · One Red Lipstick Host · Podcast for Success BSc Psychology & Sociology · Dalhousie Co-Director · Mastermind City 15+ Years · 1000s of Clients
About Stacy Maynard
Stacy Maynard
Co-Founder & COO, Too Late My Ass™ · CEO, City Media Group · Certified Professional Speaker
Stacy Maynard is the co-founder and COO of Too Late My Ass™ and the CEO of City Media Group, a podcast production and digital media company she founded in 2011. The operational architect behind a global reinvention ecosystem for people 50+, she has spent 15+ years building the systems, infrastructure, and content engines that turn bold visions into scalable, running reality. Author of One Red Lipstick. Host of Podcast for Success. Speaker of the Year. Autism advocate.
BSc Psychology & Sociology · Dalhousie University  Â·  Certified Professional Speaker  Â·  Speaker of the Year  Â·  Author · One Red Lipstick  Â·  CEO · City Media Group

Book Stacy to Speak

Available for keynotes, workshops, corporate retreats, conferences, and podcast production training globally.

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