Christopher Tufford

Chris is a serial entrepreneur, a poker enthusiast, ex-professional superbike racer, Toronto Maples Leafs fan, husband, and father. Always on the lookout for new adventures has often meant he’s taken the road less travelled or made a new one for himself. He was born in Canada and has lived there his entire life. His family has roots in Canada dating back over 150 years, meaning before it was officially a country.

Chris left college after two years to start his first business in property management with a childhood friend. He followed that with a pioneering startup in telecom that became a casualty of the dot-com meltdown. He then founded and thoroughly enjoyed a decade running the largest amateur poker tour in Canada under license to the world’s largest poker brand, the WPT. Afterwards he created a guest Wi-Fi business for restaurants that became his second business to get crushed by larger economic forces when it got wiped out by lockdowns during the pandemic.

His newest business, Green Apple Pay, is also his most passionate. It is a digital fundraising platform for organizations like charities, nonprofits and other community based groups to generate new recurring revenues from spare change and cashback rewards from their stakeholders’ everyday spending. It works like a rewards program for organizations that fundraise.

Where did the idea for Green Apple Pay come from?

After being involved in fundraising for my son’s sport-karate competition team, his school fundraisers, and watching my wife organize events for Sick Kids hospital, I had the realization that there was a better way.
Most of the fundraisers I had attended and hosted were old-fashioned, parent-run events like t-shirt sales, BBQ and bake sales, raffle ticket sales, used clothing & electronics drives, and in-person events that have been used for many decades.

I knew there were digital platforms that helped young, tech-savvy generations automate savings and cashback rewards for themselves so why wasn’t there one that helped organizations rather than the individual? Like I had previously in my entrepreneurial career, I realized that if we combined two unrelated things, we could make something bigger than the sum of its parts. The answer was merging the automated solutions that were being used by individuals with the organizational need that existed to create a new business that solved for the need of the collective many rather than the individual one.

What does your typical day look like and how do you make it productive?

I’ve never been a morning person so I’m up in time to get my son breakfast and ready for school. Beyond that, there’s not too much structure to my day as each is different from the rest depending on video meetings with various stakeholders. I would be lost without my calendar to help track when I’m free to focus on the next pressing matter alone or in meetings with sales and marketing, product development or with investors or advisors.
While I may not be an early riser, I do put in long hours and I’m often likely still at my desk at 8 or 9pm and all day Sunday. Once again, being able to block off time when needed for my son’s hockey or karate schedule in my calendar allows me to be productive when required but available as Dad too when needed.

How do you bring ideas to life?

Mostly through sheer force of will, drive, determination, and not knowing how to use the word “quit.” I have always been good at identifying opportunities and new business ideas and then making them a reality by figuring out how to do it. Most of the time, they involved my innate business acumen and sales and marketing abilities to get them at least most of the way and then filling in rest using hired help where needed.

One of the other tricks is knowing when to trust your instincts and finding one or more trusted confidants that will provide you an unvarnished truth of your idea and how rational or ridiculous it sounds. For instance, I’ve had lots of new ideas over the past decade, but my instincts told me to get a second opinion.

That person for me is my friend Darren, whom I met and worked with at the WPT, when he owned and operated some territories. He thought some of my ideas were not scalable or not viable, one that was stupid (my idea for a Toronto radio station format that provided 24hr traffic updates) and a couple that had real merit; the first one became our short-lived Poker Minds venture and Green Apple Pay.

What’s important to remember as an entrepreneur is that you need to get feedback from people who will tell you what they really think and not what you want to hear. Don’t be afraid to seek out and listen to negative feedback. If you don’t have that natural entrepreneurial instinct and don’t have that confidant either, then there are lots of places that help entrepreneurs now that can walk you through the process of becoming one step by step.

Step one of that process is asking if they think your idea has real market potential. If they’re unclear, they’ll know how to research it to add more context to answer that question better and if they immediately don’t think it is, why not. It is better to be told early that “Catbook” is a bad idea and that most cat lovers simply socialize through groups on Facebook before you spend months of your life and a lot of money on your new feline social media platform.

What’s one trend that excites you?

One trend that excites me is that the two young generations of Millennials and GenZ are both very socially active and engaged. My excitement is two-fold, so I’ll explain:

First, the fact that two generations of digital natives are more engaged even when it often appears that they are disengaged is heartwarming. Older generations (Baby Boomers & GenX) have this default assumption about these younger generations, due to the fact that they are buried face-first in their phones and social media, that they are disconnected from society in general. But the facts these past few years don’t bear that out. #MeToo and Black Lives Matter are the result of an engaged population that decided that enough was enough, and they were going make their voices heard and stand up together for what was right.

Second has more to do with Green Apple Pay and its chances for success. The combination of a technologically savvy and digitally embracing population combined with their innate socially active personalities creates the ideal conditions for a software platform like ours to experience viral growth and adoption. That makes me excited about what the future holds!

What is one habit of yours that makes you more productive as an entrepreneur?

I think it’s a combination of being committed to putting in long hours when required but keeping your head up, eyes and ears open through the process. It’s easy to “put your head down” and get stuff done but harder to do it and continue to pay attention to what else is going on around you. There’s times when you miss important opportunities if you are not keeping an eye on things while your head is down.

What advice would you give your younger self?

There are two things that are connected but seem opposite to one another:

Make the most of your time now and don’t wait for tomorrow. I’ve often taken my foot off the gas with the expectation of something that was supposed to happen the next day or the day after or soon. Don’t do that. It’s better to be busy with too much work than not enough. Don’t leave your schedule open for something expected, fill it with something definitive.

Things always take longer than expected. It’s a frustrating thing when you want to accomplish something right now but you’re waiting for something else before you can. Like my advice above, don’t open your schedule anticipating when you’ll be able to start, make yourself free when the job can start because it will almost certainly be longer than you’re expecting.

Tell us something that’s true that almost nobody agrees with you on.

I believe entrepreneurs are amongst the bravest of careers. Most people would choose police, firefighters, soldiers or something similar but I don’t agree. Neither do I include in my definition people that buy franchises or similar pre-formatted business that simply require money to open. They are on par with doctors, lawyers and dentists. All of these people have my respect but none of them have risked everything to forge a new path, create or transform an industry.
True entrepreneurs look to make significant disruptions or advancements to an industry with little more to help guide them then their own wits and instinct. True entrepreneurs are modern-day Pioneers who ride into the sunset searching for new adventure and opportunity with no safety net or maps to guide them. They figure it out and make it happen or they lose everything. That is my definition of brave.\

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Don’t quit at No. I spoke earlier about trusting your instincts and/or finding someone you can trust to provide feedback about your business idea. Once you’ve completed that process and embarked on your business adventure there will be no shortage of people that tell you No. Many people will tell you that it’s a bad idea, it won’t work, you won’t be successful and the rest. It’s mostly just noise and a test of your willpower. Listen, absorb real feedback where you think it helps make improvements but don’t otherwise let it deter you. Moving past No is a learned skill. Keep moving forward and it will get easier.

What is one strategy that has helped you grow your business?

Ask for help. Don’t be afraid that just because you’re an entrepreneur, you’re supposed to know everything. Open yourself to learning and self-improvement. It will enrich your experience, grow your network and improve your odds of success. Our entire civilization is built off the hard work and knowledge gained by those before us. Use that whenever you can to your advantage.

Connected to this, is to surround yourself with smart people and empower them to succeed and make decisions. I once read that you don’t hire smart people to tell them what to do, you hire smart people so they can tell YOU what to do.

What is one failure you had as an entrepreneur, and how did you overcome it?

In the late ’90’s with UTN, my vision for changing the way telecom services would be provided, it required a significant investment to make it a reality. This was before young tech titans like Mark Zuckerberg became a reality. I met and pitched a lot of investors and VCs and they told me I sounded credible and my idea had lots of merit but they weren’t going to invest $10M in a kid that just turned 30. To overcome this I needed to start my team building early and more specifically, find a new face of the company for these types of meetings, an older more mature face. So that’s what I did. I found an experienced executive, a 50 something ex-telecom VP named Robert. Then we went on together to raise the $10M that we needed.

What is one business idea that you’re willing to give away to our readers?

Well you can have the 24hr traffic updates radio station in Toronto idea – that’s a real thing in Vancouver BTW and Toronto has worse traffic then Vancouver does! It’s not really that crazy!

The pandemic has caused an obvious spike in the food delivery business and now ghost kitchens have had a similar growth but for me the problem with food delivery has always been (including pre-pandemic) is getting it in time that’s it still warm. A couple follow-on business ideas:

Develop/invent a better container for keeping the food warm during the delivery process – something to place the soft food coolers they put the takeout bags in, in while driving to keep them warm – a heated box that plugs in and runs off the car?

Invent a new food delivery service that actually prepares the food while in transit. I read about a company that has pizza delivery trucks that cook the pizza while they’re driving and use Ai to plan routes, deliveries and cooking so they finish in unison. What other well-known fast food products could be done this way? That would be interesting…

What is the best $100 you recently spent? What and why?

I spent almost double that much last summer to subscribe to the MotoGP app to watch the world championship motorcycle races. They weren’t going to be broadcast via the usual TV channels and the only way to watch in Canada was via subscribing to their app for coverage. Never thought I would spend that much directly for something that specific that I used to get for “free” but glad I did as it was an amazing season! Fortunately F1 is still broadcast via my regular sports TV channels…

What is one piece of software or a web service that helps you be productive?

Well it’s a boring answer but video meeting software like Zoom and Google Meet. Traditionally I’d prefer face to face meetings but I’d much rather do a video meeting then a phone call. Honestly, it’s possible to get more done this way too as you can schedule back to back to back meetings with people you could never have done previously when some basic travel, like driving to their office, was involved.

What is the one book that you recommend our community should read and why?

I’ve been reading many CEO biographies the past year or so like Elon Musk, Jeff Bezos, Marc Benioff and Phil Knight. Aside from the interest in their stories about how and why they did it, there are always little nuggets that stick with you that you mold into your own reality. One is a quote from Bezos: “the laws of physics are fixed and cannot be changed; everything else is open for discussion”. I use that with my own team to make sure they understand that I encourage them to speak up and challenge ideas then they see a need.

What is your favorite quote?

As much as I like it, Bezos’ quote isn’t my favourite. My favourite is the famous one from Desiderata. I discovered it my early 20’s and have had a copy on my home wall ever since. It’s nearly 100 years old now but still relevant. It’s also a bit long but I’ll share it anyway:

GO PLACIDLY amid the noise and the haste, and remember what peace there may be in silence. As far as possible, without surrender, be on good terms with all persons.
Speak your truth quietly and clearly; and listen to others, even to the dull and the ignorant; they too have their story.
Avoid loud and aggressive persons; they are vexatious to the spirit. If you compare yourself with others, you may become vain or bitter, for always there will be greater and lesser persons than yourself.
Enjoy your achievements as well as your plans. Keep interested in your own career, however humble; it is a real possession in the changing fortunes of time.
Exercise caution in your business affairs, for the world is full of trickery. But let this not blind you to what virtue there is; many persons strive for high ideals, and everywhere life is full of heroism.
Be yourself. Especially do not feign affection. Neither be cynical about love; for in the face of all aridity and disenchantment, it is as perennial as the grass.
Take kindly the counsel of the years, gracefully surrendering the things of youth.
Nurture strength of spirit to shield you in sudden misfortune. But do not distress yourself with dark imaginings. Many fears are born of fatigue and loneliness.
Beyond a wholesome discipline, be gentle with yourself. You are a child of the universe no less than the trees and the stars; you have a right to be here.
And whether or not it is clear to you, no doubt the universe is unfolding as it should. Therefore be at peace with God, whatever you conceive Him to be. And whatever your labors and aspirations, in the noisy confusion of life, keep peace in your soul. With all its sham, drudgery and broken dreams, it is still a beautiful world. Be cheerful. Strive to be happy.

Key Learnings:

● Chris is a serial entrepreneur, a poker enthusiast, ex-professional superbike racer, Toronto Maples Leafs fan, husband, and father.
● Gen Z and Millennials’ use of technology in their everyday lives has changed how non-profit organizations should communicate their mission to their donor base; entrepreneurs see challenges in their daily lives as opportunities to be creative
● Entrepreneurs should surround themselves with smart people and empower them to succeed and make decisions. They shouldn’t hire smart people to tell them what to do, but rather, hire smart people so they can learn from them
● Entrepreneurs should know when to trust their instincts and when they should find one or more trusted confidants that will provide them with unvarnished feedback about the idea