Enterprenuer
Chris is a serial entrepreneur and a poker enthusiast. He’s also a Toronto Maples Leaf fan and husband.
He is always on the hunt for new adventures and has often taken the less-traveled route or created a new one.
He was born in Canada and has lived there all his life. His roots in Canada go back more than 150 years. This was before Canada was even a country.
After two years of college, Chris decided to leave the university to open his first property management business with childhood friends.
Then he started a telecom startup that was a pioneer in the field, but it fell apart during the dot-com crash.
The WPT, Canada’s biggest poker brand, licensed him to run Canada’s most prominent amateur poker tournament for a decade.
He enjoyed every minute of it. He then started a guest Wi-Fi business for restaurants, which was his second business to be crushed by more considerable economic forces during the pandemic.
His most passion is his newest venture, Green Apple Pay. It is a rewards program that organizations can use to reward their fundraisers.
It’s a digital fundraising platform that allows charities, nonprofits, and other community-based groups to create new recurring revenues using spare change and cashback rewards.
From where did the idea of Green Apple Pay originate?
After helping my son with fundraising and his school fundraisers and seeing my wife organizing events for Sick Kids hospital, it dawned on me that there was a better way.
Many of the events I hosted and attended were traditional and run by parents.
They included a t-shirt and baked sales, raffle ticket sales, and used clothing and electronics drives.
Many digital platforms could help young tech-savvy generations save money and earn cashback rewards.
So why didn’t they make one that was more beneficial to organizations than individuals? As I did in my previous entrepreneurial ventures, I saw that two seemingly unrelated things could be combined to create something more significant than the sum of their parts.
I realized that the best way to solve the many problems was to combine the automated solutions people use with organizational needs.
How do you make your day more productive?
I have never been one to wake up early, so I get up on time to make my son breakfast and get him ready for school.
My day is not structured as each meeting with different stakeholders has meant that there isn’t much structure.
My calendar helps me track when I can focus on the following urgent matter or meet with sales and marketing or investors or advisors.
Despite not being an early riser, my work hours are long, and I am often still at my desk from 8-9 pm every Sunday.
I find it helpful to schedule time for my son’s hockey and karate events in my calendar so that I can be productive when necessary and available to my son as a Dad when he needs me.
How can you bring your ideas to life?
They used my business acumen, sales, and marketing skills to get them at least part of the way.
Then I hired help to fill in the rest. I always could identify opportunities and make them a reality through determination, drive, and sheer willpower.
Another trick is to know when you can trust your instincts.
Find trusted confidants who will give you the unvarnished truth about your idea and whether it is rational or absurd.
I know that my intuitions have been right over the years and gave me a second opinion.
My friend Darren is that person. He was the one who introduced me to the WPT and helped me manage some territories.
Some of my ideas weren’t scalable or viable. He also thought one was stupid, such as my idea for a Toronto radio station that would provide 24-hour traffic updates.
There were a few that had real merit. The first one was our short-lived Poker Minds venture. Green Apple Pay was the result.
As an entrepreneur, it is essential to seek out feedback from others who are honest and will not tell you what you think.
Do not be afraid to listen to and seek out negative feedback.
Many places will help you become a successful entrepreneur if you don’t possess the entrepreneurial instinct or don’t have a confidant.
Step one is to ask them if your idea has any market potential.
If they are unsure, they will be able to explain it better.
And if they don’t believe it is, they can always research it.
It’s better to tell them early that “Catbook” is not a good idea.
Most cat lovers socialize through Facebook groups before you spend months and a lot of money on your feline social media platform.
Which trend is your favorite?
I find it exciting that both GenZ and Millennials are very active on social media and engagement. This is why I am excited.
It is heartwarming to see two generations of digital natives be more engaged than their older counterparts.
The assumption that these younger generations are disconnected from society is shared among the Boomers and GenX generations.
The facts of the past few years do not support this assumption.
#MeToo, Black Lives Matter, and other movements result from an engaged community that decided enough was enough and was ready to make their voices heard and fight for what is right.
Green Apple Pay’s chances of success and second have more to do than just that.
A tech-savvy, digitally-aware population and their natural socially active personalities make it possible for software platforms like ours to grow virally and be adopted. This makes me excited for the future!
Which habit makes you more productive as an entrepreneur than another?
It’s a combination of being dedicated to working long hours and keeping your eyes, ears, and head open.
It is easy to put your head down and do things, but it’s much more challenging to keep an eye on what’s happening around you and accomplish the tasks.
You might miss out on essential opportunities if your head is down.
What advice would your younger self give you?
Two things are connected but appear to be opposite one another.
Don’t wait until tomorrow to make the most of your moment.
Sometimes I have put my foot down and hoped for something to happen tomorrow, the next day, or the day after. Do not do this.
It is better to be too busy and do too little work than too much.
Please do not leave your schedule empty for something you don’t expect, but fill it with something meaningful.
Sometimes things take longer than you expected. It can be frustrating when you want to do something but wait for something else.
As I said, don’t plan for when you can start. Instead, set yourself up to be available when the job is ready.
It will almost certainly take longer than you expected.
We need to hear something you believe is accurate and that nearly everyone agrees with.
Entrepreneurs are my favorite career. Many people would prefer to be firefighters, police officers, or soldiers, but I’m afraid I have to disagree.
My definition does not include people who buy franchises or other pre-formatted businesses that only require money to open.
They are just like doctors, lawyers, and dentists. They all have my respect, but none would risk everything to create or transform an industry.
Modern-day Pioneers are true entrepreneurs who set out on their own, seeking new opportunities and adventure.
True entrepreneurs strive to create significant disruptions in industry or make advancements.
They have little else to guide them than their intuition and wits. They don’t have any maps or safety nets.
They either figure it out and make it happen or lose it all. This is what I consider brave.
What is one thing that you recommend to everyone as a successful entrepreneur?
Don’t quit at No. Trust your instincts and find someone who can give feedback on your business idea. I mentioned this earlier.
Many people will tell you No once you have completed the process and started your business venture.
Many will say to you it’s a bad idea. It won’t work. You won’t succeed.
It’s mostly noise and a test of your willpower. Listen and take in the feedback when you feel it will help you improve, but don’t let it stop you.
It is possible to move past No. It will get easier if you keep moving forward.
Which strategy has been most successful in growing your business?
Ask for help. Do not be afraid to ask for help. Learn and improve yourself.
The hard work and knowledge of those who came before us have shaped our entire society.
You can use it whenever you want to. You will be enriched by it, your network will grow, and your chances of success will increase.
This is connected to surrounding yourself with intelligent people to empower them to make good decisions and succeed.
It is impossible to hire smart people to tell them how to do things, but wise people are hired to help you do it.
How did you overcome that failure as an entrepreneur?
My vision to change the way telecom services were provided was realized in the late 1990s by UTN.
It required significant investments to become a reality.
This was before tech giants such as Mark Zuckerberg were a reality.
I met and pitched to many investors and VCs. They said I sounded credible, my idea had lots to offer, and that they wouldn’t invest $10M for a 30-year-old kid.
This made it difficult for me to build my team early and, even more importantly, find an older, more mature person to represent the company at these meetings.
That’s precisely what I did. Robert, a former VP of Telecom, was an experienced executive.
We then worked together to raise the $10M we needed.
Which business idea would you be willing to share with our readers?
You can still have the 24hr Traffic Updates Radio Station in Toronto. It’s a thing in Vancouver.
However, Toronto has more traffic than Vancouver. It’s not so crazy!
Although the pandemic caused a noticeable increase in food delivery, ghost kitchens also saw increased business.
However, the main problem with food delivery (pre-pandemic and post-pandemic) was getting it to you in time, so it’s still warm. Here are some ideas for business continuation:
Create/invent a better container to keep the food warm during delivery.
This could be something that they place in the soft food coolers and then drive to keep them warm.
Invent a food delivery service that prepares food in transit.
One company has delivery trucks that make pizzas while they drive.
They use Ai to plan their routes and deliveries and cook in unison.
This could also be used to deliver other fast-food products. It would be fascinating…
Which was the most expensive $100 you spent recently? Which and why?
To watch the MotoGP world championship motorcycle races, I paid almost twice that amount last summer.
These races were not going to be shown on the regular TV channels.
The only way to see them in Canada was to subscribe to their app.
It was a season that I never thought I would pay that much for.
F1 can still be seen on my regular sports TV channels…
Which piece of software or web service can you use to help you be more productive?
It’s boring, but you can use video meeting software such as Zoom or Google Meet.
Although I prefer face-to-face meetings, I would rather have a video conference than a call.
It’s possible to do more with this method. You can schedule back-to-back meetings with people that you couldn’t have done before if you could drive to their offices.
Which book would you recommend to our community? Why?
Over the past year, I have read many biographies of CEOs like Marc Benioff, Jeff Bezos, and Phil Knight.
Apart from the fascination in their stories, you will also find little gems that will help you shape your reality.
Bezos once said that the laws of physics cannot be altered and could not be changed.
Everything else is up for debate. I share that quote with them to make sure my team understands that.
I encourage them not to be afraid to challenge their ideas when they feel necessary.
Which quote is your favorite?
It’s not my favorite quote, no matter how much I love it. The famous Desiderata quote is my favorite.
It was a book I found in my 20s that I loved and have kept a copy of it on my wall since.
Although it’s almost 100 years old, it is still very relevant. Although it’s a little long, I will share it anyway.
Be calm in the midst of the chaos and haste, and remember the peace that can be found in silence.
Be on good terms with everyone, as much as possible, and without surrender.
Talk your truth clearly and quietly; listen to other people, even the dumb and ignorant. They, too, have a story.
Avoid aggressive and loud people. They can be a burden on the spirit.
Comparing yourself with others can lead you to be bitter or vain. There will always be more and less than you.
Take pride in your accomplishments and your plans. Keep your career alive, even if it’s modest. It is an essential asset in the changing fortunes.
Be careful in your business dealings, as the world is full of tricks.
This should not blind you from the goodness that exists.
Many people strive for high ideals, and life is full of heroism.
Be authentic.
Don’t pretend to be in love. Do not be too sarcastic about your passion.
It is as perennial and resilient as the grass, even in all its aridity.
You can take kindly the wisdom of the years and gracefully give up the possessions of youth.
To protect yourself from sudden misfortunes, nurture your spiritual strength.
Do not let dark thoughts get in the way of your happiness.
Fears can be triggered by loneliness and fatigue.
Be gentle with yourself, and not only do you need to be an excellent example of discipline.
You are no more minor a child of God than the stars and trees; you have the right to be here.
It doesn’t matter if it’s evident to you or not. The universe is working as it should.
Be at peace with God. No matter what, you believe Him. Keep peace within your soul, no matter what your hopes and dreams may be.
It is still beautiful, even with struggle, pain, and broken dreams. Keep smiling. Be happy.
What could the Key Learnings “Christopher Tufford” offer to Enterprenuer readers?
Chris is a serial entrepreneur and a poker enthusiast.
He is also a Toronto Maples Leaf fan, husband, and father.
Gen Z and Millennials’ use of technology in everyday life has changed how non-profit organizations communicate their mission to donors.
Entrepreneurs see challenges in daily life as opportunities to be creative.
Entrepreneurs need to surround themselves with intelligent people who will help them succeed and make the right decisions.
Instead of hiring smart people to tell entrepreneurs what to do, they should hire smart people to learn from them.
Entrepreneurs need to know when to trust their intuitions and when to find trusted confidants who will give them honest feedback about their idea.
