Evolving Entrepreneurship

What if your optician felt less like a clinic and more like the Muppet Theater? Two friends left jobs that were turning into numbers and built an eyewear shop in Stratford.

Nicole (the Coles) and Nikki (the Keys) of Coles and Keys join Janis and Holly this week. The two started in the optical industry the same year, 2012, but only met after years of family connections and "you two have to meet" nudges. Their first phone call in October 2020, was so good neither wanted to hang up. Then a joke about "if we ever had our own optical" became "when."

You'll discover:

• How the pandemic, with its plexiglass, masks, scrubs and 15-minute appointments, pushed them to build a warmer, more human kind of optical
• Why they call glasses "wearable art," and why they pitch a new pair as your next chapter, the face people will remember in your photos for the next two to five years
• What it's like to open on York Street, where neighbors chat on the sidewalk and every shop is curated with intention
• How the whole process works if you've never bought frames outside your eye doctor's office: bring your prescription, talk through your real visual needs, and get lenses from a lab in London, Ontario, cut in-house by the shop
• The aftercare that makes the shop feel different: lens warranties, unlimited adjustments, tune-ups every six to eight months and free cleaning spray refills

The conversation also covers what it takes to run a business with your best friend, why independent makers matter, and what's next for the shop. That includes new lines inspired by the Silmo show in Paris and some things they're excited to share in 2027.

Both guests are Starter Company alumni. Nicole is the licensed optician, and Nikki is the certified optometric assistant.

Perfect for small business owners, anyone considering a partnership with a friend, and anyone who has ever felt out of place in a space that was supposed to serve them.

Find them at colesandkeys.ca, on York Street in Stratford, Ontario, and on social media at Coles and Keys Optical.

Collaboration can make solo entrepreneurship less lonely. Holly and Janis talk with three Starter Company alumni: Gabby Fortune (Cuyuni Creates, Gal Society), Lisa Hartman (Hartman's Coffee and Tea) and Sam (the Kin Cabin). They cover how to choose and pitch collaborators, when to say no, and which partnerships turned out better than expected. They also talk about looking after your mental health as a business owner. Community over competition.

• 0:33 Introductions: Gabby, Lisa and Sam
• 3:12 Walking into the program: nerves, welcome and community
• 5:55 Fears and positive experiences with collaborating
• 10:49 Contracts or word of mouth?
• 11:41 Was collaboration always a priority?
• 14:08 Different levels of collaboration
• 16:21 Pitching versus spontaneous teaming up
• 20:13 Saying no to a collaboration that doesn't fit
• 23:00 Collaboration and feeling less alone
• 23:58 Unexpectedly amazing collaborations: Hive & Honey, Hartman's Little Gallery, and friends who helped through a business pause
• 28:56 Asking for help and mental health
• 31:11 Coping tools: a snuggie, friends, art and a specific "fun list"
• 36:02 Where to find the guests:
  • Sam: thekincabin.ca and @thekincabin
  • Gabby: back in November
  • Lisa: Hartman's Coffee and Tea, 2 Ontario Street
• 39:33 Alumni meetup plans and community over competition

In this episode, our guest, Rebecca Northan, shares her journey from improv artist to entrepreneur, exploring how artistic practice informs business success, the importance of spontaneity and curiosity, and navigating challenges like menopause and perfectionism. And how she adds some of her own SPICE to continue to grow her empire.

In this episode, Chelsea Steenbergen shares her journey of starting Apple Bottom Orchards, discussing the challenges and rewards of diversifying their farming business. She highlights the importance of trying to find some sort of balance to her family life, work, and the demands of running a farm while also exploring agritourism and cider production. Chelsea talks about her version of entrepreneurship, emphasizing the balance between planning and spontaneity, the significance of mental wellness, and the role of family in farming. The discussion also highlights the joy of engaging with the community through her cider production and the personal growth that comes from overcoming challenges.

Takeaways

• Diversification in farming is key
• Balancing work and family life Embrace uncertainty in entrepreneurship
• Mental wellness is crucial for success

Chapters

• 00:00 Introduction to Chelsea Steenbergen
• 03:00 The Journey of Apple Bottom Orchards
• 05:55 Cider Production and Future Plans
• 07:58 Educational Background and Career Path
• 10:52 Balancing Family, Work, and Farming
• 16:10 Building a Seasonal Team
• 17:49 Agritourism Experience at the Orchard
• 20:59 Challenges in Starting a Business
• 23:25 Navigating Entrepreneurship Without a Plan
• 26:11 The Importance of Mental Wellness
• 28:55 Family Dynamics in Farming
• 34:38 Passion for Cider and Community Engagement

Episode Duration: 52 minutes

In this week’s podcast episode, Naomi Clement shares how she turned a passion for pottery into a sustainable business through teaching, community, and creativity and by building a repeat and recurring revenue stream with her own membership space.

If you're in the arts and culture space, her journey will inspire you to think differently about how you grow.

About Our Guest:

Naomi Clement is a Canadian artist and educator who explores ideas of home and belonging through the powerful lens of functional ceramics. She received her MFA from Louisiana State University in 2017, and her B.F.A from the Nova Scotia College of Art & Design University in 2003. Naomi has participated in residencies, given lectures and workshops, and exhibited her work across Canada and the United States. She served as a board member for the National Council on the Education for the Ceramic Arts (NCECA), and was named a 2017 Emerging Artist by Ceramics Monthly magazine.

In 2019, Naomi was a Summer Artist-in-Residence at the renowned Archie Bray Foundation for the Ceramic Arts, in Helena, Montana. After spending many years as a pottery nomad, working and travelling across North America, Naomi has recently established a home studio in Stratford, Ontario.

Find Naomi at: https://naomiclement.com/

Episode Duration: 35 minutes

In this bonus episode of Evolving Entrepreneurship, we chat with Intern Meredith about her time at the Stratford Perth Centre for Business, her time managing the Summer Company program and her thoughts on entrepreneurship from a Gen Z perspective.

Stratford Perth Centre for Business

The Centre offers complimentary consultation and resources for new and established small businesses, including:

Episode Duration: 59 minutes

What if you led your hospitality business with transparency and values? From staffing to growth, Shelley Windsor of Windsor Hospitality Group has seen it all and led through it all. In this week’s podcast episode, we sit down with the trailblazing entrepreneur to explore:

Her leadership approach to managing a large team.

How she manages cash flow in a seasonal industry.

How do her roots show up in her business.

Whether you’re in food service or any service-based business, this conversation is packed with lessons on resilience, people-first leadership, and long-term vision.

Shelley Windsor is the co-owner of Windsor Hospitality Inc., a Stratford-based management and consulting firm whose portfolio includes Mercer Kitchen & Beer Hall, The Prune Restaurant, Events@151, Foster’s Inn, and several Best Western properties, including the newly opened BW@Home in Walkerton. 

She oversees financial operations while actively staying involved in day-to-day operational performance, human resources, and the strategic use of technology to streamline processes, increase revenue, and operate efficiently. 

Guided by a philosophy of staying relevant, giving back to the community, fostering exceptional workplaces, and prioritizing customer experience, Shelley is committed to both operational excellence and meaningful community impact.

Find Shelley here: https://www.windsorhospitality.ca/

Episode Duration: 49 minutes

This week on Evolving Entrepreneurship, we sit down with Marian deWever, broker, owner, and leader, to talk about building a brokerage rooted in values, integrity, and genuine care for families.

Tune in as Marian shares how she’s redefining success in real estate beyond sales, toward service and community.

Home And Company: https://www.homeandcompany.ca/marian-dewever/

The real estate market and the business of real estate are constantly evolving and in 2013, after 23 years working for major franchise companies, Marian, finally, took the leap of faith to build Home & Company Real Estate.  She is driven by her confidence and determination to make a positive impact in the real estate market, in her community and provide better services to her clients.

‘‘As Realtors we have the most awesome privilege of being involved in a family’s journey to find HOME. This relationship deserves our enthusiasm, patience, skilled guidance and our very best efforts, always.’’

As a Certified Real Estate Brokerage Manager (CRB) – the most prestigious credential in the industry, conferred by the Real Estate Business Institute (REBI) and endorsed by the National Association of REALTORS® – Marian exemplifies a commitment to professionalism, innovation, and success.

Stratford is home to Marian, husband and business partner, Robert and 2 cats with dog like personalities. They are proud parents of their suddenly adult children, Emma and Maklane.  When not working, time spent travelling, a bit of cycling or hiking, or relaxing with friends, makes life complete.

If you are seeking a real estate partner who dares to be different, Marian deWever is a name to trust. Her pursuit of excellence and dedication to providing the utmost in service has earned her a sterling reputation among savvy clients who recognize the value of working with a true industry leader.

Episode Duration: 40 minutes

This week on the podcast, we’re joined by Janis Antonio, owner of Dunny’s Source for Sports in Stratford & St. Marys.

Janis shares what it’s like to step into a long-standing community business, lead a multi-generational team, and navigate the unique challenges of managing Gen Z employees, all while honouring Stratford’s deep sports legacy.

Whether you're running a local business or navigating workplace change, this episode is packed with insight, heart, and real-life leadership lessons.

Dunny's Source For Sports: https://www.sourceforsports.ca/pages/dunnys-source-for-sports-stratford

Janis Antonio from Dunny’s Source for Sports, a locally owned and operated sporting goods business proudly serving Stratford and St. Marys, ON. Born and raised in Stratford, the Dunny’s family has deep roots in the community and is active in local sports both on and off the ice. Specializing in hockey, baseball, and custom team & corporate apparel, they’ve become a go-to for athletes, teams, and businesses alike.