From Entrepreneur to CEO: An Upside Foundation Breakfast - Upside Foundation of Canada

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From Entrepreneur to CEO: An Upside Foundation Breakfast
May 31, 2017


An opportunity for Upside members to learn, reflect and connect.

You have the DNA of an entrepreneur. 90% of the time it serves you well. What about when the nature of your contribution needs to be different? These moments challenge entrepreneurs. Everyone is watching. Can you slide into the role of superstar CEO? Should you? Your funders are watching. Your employees are talking. And deep down, your inner critic is on overdrive. How do you want to show up? The best new CEOs embrace the honest uncertainty that comes with their new title. They get to work designing their own unique leadership style.

On May 19 in Toronto, The Upside Foundation welcomed Brent Lowe as a guest speaker. Brent is The Scale Coach for Founder CEOs, helping entrepreneurs conquer the steep learning curve that comes with rapid growth. At our breakfast, Brent shared how some entrepreneurs are redefining the role of CEO and reinventing their startup in the process. Great discussions were had by the leaders in attendance around leadership styles and key decision points organizations face.  We’ve captured the key questions Brent posed during his talk below, along with links to relevant material.

7 Questions Founders Should Consider on the Journey from Entrepreneur to CEO

1) Will I lead from a place of authority (protecting the organization) or a place of power (controlling others)?

2) How will I establish social contracts (relationships and agreements) with my team?

3) What role will purpose have in the every day leading my organization?

4) What role will pay play in my organization?

5) How will decisions be made in my organization?

6) How transparent will I be?

7) How will I structure the organization to align with my leadership beliefs?

Recommended Resources 

We hope you can leverage these insights as you reflect on and proactively plan for the kind of leader you will be as you progress along your leadership journey.

“An organization cannot evolve beyond its leadership’s stage of development.” – Frederic Laloux, Author, Reinventing Organizations

Thank you to Brent Lowe for lending his expertise to Upside Foundation members. To recognize Bren’t’s contribution, a donation was made to Beautiful World, a charity that provides scholarships for girls across sub-Saharan Africa.

Thank you to Bennett Jones for hosting us in their space.  Hugo Alves and Ranjeev Dhillon have served as The Upside Foundation’s lawyers since our inception, providing legal services to Upside pro-bono and to our members at a reduced rate.  Ranj and Hugo offered 3 hours of free legal services to the next 3 companies who joined The Upside Foundation- an offer that was quickly seized.

Interested in participating in similar events in the future? Take the pledge today to ‘share the upside’ and reap the benefits of being a company that cares!


Brent Lowe is The Scale Coach for Founder CEOs. As a coach and author, Brent helps entrepreneurs conquer the steep learning curve that comes with rapid growth. His speciality is working with founders on the journey from kitchen table to 200 employees. Many of his clients are focused, in big and small ways, on solving problems related to the UN Global Goals for sustainability.   Brent is the author of Reinventing Startups, a practical toolkit for founders and leaders.


The Upside Foundation of Canada is a registered charity. The Foundation provides an innovative corporate philanthropy platform to help Canadian startups and high-growth companies “Share the Upside”. Since startups’ cash is scarce, as is time, the Foundation makes charitable giving quick, easy and cash-free.

The model is powerful: Earlier-stage and high growth private companies pledge stock options or warrants to the Upside Foundation. When the company has a liquidity event (e.g., IPO, acquisition), the Foundation monetizes the options and donates the proceeds to registered Canadian charities selected by the donors (and approved by the Foundation).

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