Conscious Entrepreneurship: May I introduce Kristi Herold

Demee Koch
5 min readNov 30, 2020

A born entrepreneur, Kristi Herold was struggling to meet new people after a move to Toronto in 1996 and she took the opportunity to combine her passion for sport, business, and community in founding the Sport & Social Group (SSG) — adult recreational sports leagues, providing an incredible physical and mental health benefit to over 1.3 million participants since inception.

Conscious Entrepreneurship — May I introduce: Kristi Herold

Kristi has grown the SSG to be one of the largest organizations of its kind in the world, with 35 full-time and 300 part-time employees and 150,000 annual participants across 9 cities in Canada and the US. Kristi’s vision is to get 1 million people playing annually.

Kristi is passionate about giving back, having led the launch of SSG’s foundation “Keep Playing Kids” providing free sports programming for underserved children in SSG communities and engaging SSG members to volunteer as coaches. The SSG also has raised over $300,000 for international charity “Right to Play”.

SSG has been forced to stop sports play during the Covid pandemic, however they have stayed true to the purpose of connecting people through play as Kristi has led her team in the creation of JAM — a new venture helping global corporate teams stay connected through fun remote games and events.

Kristi was awarded the Governor General’s “Queen’s Diamond Jubilee” award in 2009, in recognition of her contribution to community. She was thrilled that the SSG received a “Great Places to Work Certification” in 2019. And in 2020 Kristi was proud to be recognized as a top 3 finalist in the Canadian Women Entrepreneur Awards.

CONSCIOUS ENTREPRENEURSHIP — What meaning do you give this term?

Conscious entrepreneurship means pursuing a business opportunity that the entrepreneur is passionate about and can find purpose in — something that makes it exciting to get out of bed each day!

MENTORS — We all need a little help along the journey. Who has been an invaluable mentor for you? Can you share a story about how they made an impact?

My father — an entrepreneur who always put family first. He has always been my inspiration throughout my entrepreneurial career.

TO THRIVE — When you see yourself thriving: Do you see yourself opening up opportunities for others along the way to participate in your success, and how?

Yes — when I started the SSG — I took care of everything by myself. Over the years as the organization has grown, it has been exciting to be able to create work opportunities for thousands of employees as well as get to witness smiles, friendships and love stories occur in the lives of over a million customers. This is a business that is easy to wake up and be passionate about on a daily basis!

CAUSE — What are the causes close to your heart, and you are supporting right now? Can you share a story how you got involved? How did it make you feel?

I’m passionate about the physical and mental health benefits that come from continuing to play as adults. I’m also passionate about ensuring children have the opportunity to keep playing — thus the reason for the creation of our foundation “Keep Playing Kids” — funding free sports programming for vulnerable children in our communities.

THE FUTURE — How do you see the face of entrepreneurship in 5 years? How do companies /brands need to adapt to secure their place in the future?

More than ever — passion and purpose are key. In order to build a great organization/brand your team must be passionate about what they are doing and in order for that passion to exist they must feel driven by the purpose and the vision.

ADVICE — What kind of advice would you like to give to an aspiring entrepreneur who feels limited due to their background or lack of resources?

Don’t hesitate to reach out and ask others for help. I am always thrilled to be the ‘dumbest person in the room’ — I ask a lot of questions in order to better learn and understand how to get something done — and I keep asking questions every step of the way. Everyone who has had success in their life has had help along the way — don’t be afraid to ask for help and experience sharing from those who have gone before — more often than not people will be willing to give you some time and share some experience in order to help you along the way — knowing one day you’ll be paying it forward as well!

DRIVE — Do you sometimes feel bad for “wanting more out of life”, and if so, why? What is your personal motivation that leads you through the hardships of entrepreneurship?

I’ve been called a ‘never give up kind of girl’ — somewhat innate within me I suppose. I have had many ups and downs throughout my career. This 25th year of running my business has been the most challenging due to the pandemic — yet I refused to give up and out of this year we have created a brand new venture “JAM” connecting corporate teams through play. It is important to always lean in, say ‘Yes’ and try new things as you never know what will happen. Never give up!

CHALLENGES — Entrepreneurship is very challenging. We each have our own coping mechanism. Mine is humor. What is yours? Can you share a story?

I’m a big believer that we create our own luck. When most people would shy away from asking a question, afraid of hearing ‘No’, I lean in — with the attitude that “the worst they say is No…and what if they say Yes!”. I recall one day walking through an airport — knowing full well my ticket would not allow me in to business class lounge, I had lots of time on my hands and thought I would “just ask”…the woman at the counter said “sorry, your ticket doesn’t allow you in here” and as I turned to walk away, a businessman behind me said “I can have one guest for free on my card, you’re welcome to use my guest pass.”. I believe this is a great example of ‘creating our own luck’ in life!

YOU — Is there anything you would like to share that we have not asked you here?

Nothing makes me happier than connecting people through play — whether it be connecting people through sports leagues — or more recently by connecting corporate teams with our playful remote events — it brings me so much joy knowing the work I do every day is making people smile and positively impacting their physical and mental health. It is easy to get excited about my work when I’m pursuing what I am most passionate about.


Connect with Kristi Herold on LinkedIn

Demee Koch about the MEDIUM interview series on CONSCIOUS ENTREPRENEURSHIP:

Conscious entrepreneurship for me is about building a sustainable business that values and respects the resources used and makes an effort of giving back to society.

I believe we need entrepreneurs to really get involved in the causes close to their heart.

This is why I reach out to entrepreneurs that aim for more than generating profit. With this interview, I aim to share entrepreneurial purpose-led passion to inspire others.

Looking forward to learn from you. Reach out to me via LinkedIn.
Demee ❤︎



Demee Koch

Entrepreneur & Board Advisor in the health & beauty industry. Introducing purpose-driven founders and beautiful minds here on Medium.