Jayne McCaw

Founder, Jayne’s Cottages

Finalist, Start-Up Award, Central


Jayne took inspiration from her love of cottage living and enjoyment of curating unforgettable family vacations to create Jayne’s Cottages — a full-service, luxury Muskoka cottage rental and concierge company. Starting with just a handful of cottages in 2014, her business has seen rapid growth. Today, she has over 60 employees and they manage almost 200 of the finest properties in the region.


My first job ever was… working at Tim Hortons. 

I decided to be an entrepreneur because… I always felt that I could offer so much 

more if I had more freedom and authority to act on my own thoughts and impulses than I could as an employee for someone else. I always felt stifled and constrained and thought I could do a better job for both my employer and the customer if I had the ability to do so. That being said, for most of my career, I enjoyed working for others and learning from my mentors and eventually giving the experience and courage to pursue entrepreneurship. 

My proudest accomplishment is… how the company has grown less than 5 years to employ 70 people – 50 people who live year-round in Muskoka, 20 seasonal employees from outside the region. Also, we now have 10 year-round employees.

I surprise people when I tell them… that my business is only 5 years old as it is now a fixture in Muskoka and is a large employer in the area. 

My best advice to people starting up a business is… utilize all the resources available to small businesses (grants, small business funding, college entrepreneurship courses, local employment and government agencies to support small businesses, chamber of commerce etc). I was not aware, and don’t think other small businesses are aware of how beneficial these resources could be and they have been very helpful to get me where we are now. 

My best advice from a mentor was… to listen to others and plead for understanding. Work with your stakeholders so everyone understands all sides. 


“I stay inspired by the joy I get from my employees who now have a stable job with our business and we can provide a fulfilling future for them in their home community.”


My biggest setback was… losing great staff during the summer season as they quit to accept year-round positions. 

I overcame it by… hiring my best staff on a year-round basis and not laying them off after the summer season even though I did not really have the income to support year-round employment. I feel responsible for their livelihood in this community where there is little year-round employment. I know that they are very committed to my company just as I have shown my commitment to them. 

I stay inspired by… the joy I get from my employees who now have a stable job with our business and we can provide a fulfilling future for them in their home community and continue to add more employment opportunities as we grow. 

If I had one more hour in the day… I would spend it with my 4 children and partner. 

The future excites me because… I love what I do and what I have achieved and know I can continue to grow with the help of my new software platform and my network of global property managers. We have the formula now to help more guests with great vacation experiences and more owners with safe additional income and look forward to growing this formula into other markets. And most importantly the future is exciting as we continue to expand our home base of this travel/tech company in the Muskoka community as we grow outside of Muskoka while providing employment and economic growth through our business success to our region. 

My next step is… doing what I do in Ontario in other popular global travel destinations. With an over 50% repeat guest rate and guests repeatedly putting their faith in Jayne’s Cottages for very expensive vacations, I am now working through my network of property managers globally to connect with and entrust these property managers with my guests who can guarantee a great guest experience. This will be facilitated by the launch of my software that will allow new property managers to easily onboard and market their properties to anyone associated with Jayne’s Cottages such as a hotel with properties, property manager with properties, real estate company with properties or a single property owner. 

Related Posts

Recommended Posts

As the Senior Vice President of Business Development at AscendantFX, Shemina ...

Learn more

    Despite the business case for diversity, or perhaps because of it, ...

Learn more

Jacqueline Thorpe is Bureau Chief for Bloomberg News in Toronto, where she wrangles a team of ...

Learn more

Christine Laperriere is a seasoned expert on helping leaders and teams reduce internal ...

Learn more

Andrea Weinberg is the founder and CEO of The ANDI Brand, a line of functional fashion that ...

Learn more


Sign up for Monday Motivation!
This dose of inspiration at the top of each week is just what you need to start your week off on the right foot. Expect quotes, profiles, and actionable advice, plus something fun to get you feeling good until Friday.
You're in!
We respect your privacy. Your information is safe and will never be shared. You may unsubscribe at any time.
Don't miss out. Subscribe today.
Sign up for our Entrepreneur E-Newsletter!
Do you own your own business? If your answer is 'yes' it's time for you to join Canada's largest community of female entrepreneurs.
You're in! Now just confirm your email address and you're all set.
We respect your privacy. Your information is safe and will never be shared.
Don't miss out. Subscribe today.