Coach. Speaker. Entrepreneur.


Maverick by heart and futurist by mind

I am on a mission to heal mental illness in the business world.

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A celebrated educator and a serial entrepreneur, Cherry Rose has educated Canada's richest families. It was here that she asked:

How can we create a legacy that matters?

Born to five generations of entrepreneurs, she inspires enterpreneurs to build a legacy that ignites the soul. As a Certified Transformative Coach, she makes Big Hairy Audacious Goals a reality.

Cherry Rose is an early investor of Paycase Financial, the bridge between traditional and crypto finance. The company is launching Canada’s first fully-compliant crypto exchange with TMX and BMO.

She has represented Canada at Columbia University's Klingenstein Summer Institute. She also holds a Master of Arts in Education and the Robert S. Lockhart Award in Psychology from the University of Toronto. Having three certifications in Special Education, the highest level possible, she has traveled and trained under the world’s top coaches.

With a decade in psychology, she is a mental health authority in the tech space. She values deep connection, delivering inspiring keynotes around the world. Her first book Parallels will be released in August 2019.

Her dream is to inspire one billion souls to live their true calling. She loves early mornings, dance parties, and epic moonshots.


Tell your heart that the fear of suffering is worse than the suffering itself. And that no heart has ever suffered when it goes in search of its dreams, because every second of the search is a second's encounter with eternity.

― Paulo Coelho, The Alchemist


My Story

I always knew I was different. My earliest memory of Canada was our very first apartment. Like other families who move to Canada, my parents dreamed of a better life for myself and my brother. They were committed to rebuilding our wealth.

Coming from an entrepreneurial family, my parents would share stories about my ancestors. My great-great-grandfather started our family’s first business. My great-grandfather started our philanthropic roots, creating scholarships for university students. Even though things were tough, starting a new life in a new country, I had these stories. I had the legacy, the knowing that we could do it again.

I knew from that point on that I wanted to be an entrepreneur.

There were dark times. I was bullied for six years, developing depression when I was young. With no friends, I spent hours reading books and playing video games with my brother. It was in those moments, sitting by the TV and sharing our dreams, that we made a lifelong pledge: to create company after company until we changed the world.

For 14 years, I shared the founder journey with my brother. We were persistent, failing and innovating in multiple industries: education, finance, technology, and more. We would spend hundreds of hours plotting our next move, dreaming the craziest ideas one could imagine. Between the eight businesses that we created, six of them failed.

Regardless, we had a commitment to excellence. I taught at the oldest preparatory schools in Canada, teaching billionaire families. I wanted to understand what went wrong, how we could do things differently. I was tired of the hustle-and-grind model that was hailed all over the media. I was watching every industry fall apart from burnout and stress. Surely there was a better way to do business, to play the long game.

Since 2014, it has been our honour to champion crypto. Mavericks by heart and futurists by mind, we saw how crypto could change the world. It led to the creation of Paycase Financial, launching Canada’s first fully-compliant crypto exchange with TMX and BMO. Serving as an early investor, the company now fights for the bottom billion.

Our dream has become a reality.

As a survivor, I am a firm believer that each person is here for a reason. I have watched my dreams come true, seen miracles happen for my family and for my clients. It is my life’s work to catalyze that aliveness and that brilliance in entrepreneurs. To ask the most important questions that ignite the soul, so we can create the legacies that we were meant to live.

What will your legacy be?

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