Interested in starting your own entrepreneurial journey but unsure what to expect? Then read up on our interview with Glain Roberts-McCabe, Founder of The Roundtable, located in Toronto, ON, Canada.

What's your business, and who are your customers?

The Roundtable is a group coaching company that specializes in helping high-performing mid-level and senior leaders navigate change, disruption, and growth by building the core behaviors they need to be successful. We offer group, team, and individual coaching to Fortune 500 companies both virtually and in person around the globe.

Tell us about yourself

In early 2001, I was the managing partner of a consulting firm specializing in leadership development. I noticed there was a gap in the market for how top talent was being developed. CEOs had access to peer forum coaching groups, and yet for mid-career leaders, the choices were between 1:1 coaching or full-day classroom experiences. I created The Roundtable specifically to help high-performing leaders cultivate their leadership by learning from each other and accelerating their capability to manage and adapt to the rapidly changing workplace environment. What I love most about the work we do is that we work with incredibly smart, committed, and talented individuals who are driven to bring their best selves to the job of leadership. As leaders, we have this incredible opportunity to impact the lives of those who work with us in a meaningful and lasting way. I feel like when we help one leader get better, we create positive ripples across organizations, families, and communities. It's very rewarding.

What's your biggest accomplishment as a business owner?

When I started The Roundtable, my first focus was on building a sustainable business. Now that we're 15 years into the journey, we've grown past seven figures, won multiple awards for our work, and have a roster of highly respected clients, yet my biggest accomplishment occurred this summer when I was able to take a two-month sabbatical from my business thanks to the incredible team that we have here at The Roundtable. I'm so proud of the culture we've created and the team members I have who care about the business as much as I do. It's truly a Founder's dream come true.

What's one of the hardest things that come with being a business owner?

The hardest thing for me over the years has been finding the right talent and learning to let go when I do find it. As a business owner, you have to create space for others to bring in their ideas and help you shape the business to the next stage of growth. Learning to let go and create space for others continues to be a growth opportunity that I focus on.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. Really clarify your niche and focus on being the very best that you can be in that area. When I started the business, I was offering multiple products that I felt I needed to have to 'be legit.' Once I started to focus my message on one core product (our signature group coaching program), our business took off.
  2. Hire slowly; fire fast. In the early years, I felt grateful that people were willing to join my start-up and often hired 'too much, too soon' or kept people for too long whose talents had become out of step with the needs of the business.
  3. Build a network of supporters. Over the years, I've been a part of many entrepreneurs groups, hired coaches, and worked with mentors to help me evolve my thinking about the business and clarify where I want to take it, plus be a much-needed sounding board on those days where I felt like I was losing my mind. Entrepreneurship can be very lonely, and no one really understands the pressures you face as you worry about payroll, talent, and letting go of control like a fellow entrepreneur will. Don't try and go it alone.

Is there anything else you'd like to share?

One of the key secrets to being a great entrepreneur is knowing how to lead. The best thing you can do for your business and your team is to work on yourself. Understanding your own strengths, biases, and blindspots will help you make better decisions, lead more effectively, and have more joy in your business.

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

Turn your craft into recurring revenue with Subkit. Start your subscription offering in minutes and supercharge it with growth levers. Get early access here.