All entrepreneurs can remember their very first business endeavour – typically a humble beginning that starts with passion and determination and ends with lessons learned. The venture where founders can dip their toes into the pool of possibilities of entrepreneurship and get a bittersweet taste of what could be.

Many of these beginnings can be as simple as selling cookies for school fundraisers, but just taking the first step can be the gain the fuel one needs to rev up their entrepreneurial engine. One of the most common first steps many entrepreneurs can give credit to is childhood lemonade stands.

The OG driver of entrepreneurship, lemonade stands ignite a flame for aspiring business owners and opens their eyes to the possibilities of what a career as an entrepreneur might look like.

That’s why the DMZ is giving an ode to the lemonade stand and paying tribute to the founders who dared to be bold, making the squeeze without knowing what their futures would hold.

We asked some of our founders to share what their lemonade stand was and what humble beginning triggered their thirst for entrepreneurship.

What was your lemonade stand (first entrepreneurial endeavour)?

“My first lemonade stand was an actual lemonade stand with chocolate chip cookies. I also walked dogs, pet sat, ran group garage sales to buy a go-kart and more. But, I think the most interesting entrepreneurial endeavour was spray painting street numbers on curbs. When I was about fourteen I heard about an eleven-year-old in California who was making good money painting street numbers on curbs to make it easier for friends and emergency services to find houses in the dark. I thought it was a great idea and wanted to earn some cash over the summer so I recruited 2 friends and got to work. Most days that summer we would load up my red and black childhood wagon with reflective spray paint, street number stencils, sign-up sheets and change. Then we would go door to door in every neighbourhood we could walk to or sometimes get a drive to the more affluent neighbourhoods to sell our services. To be honest, it wasn’t super successful but we made some cash and it definitely trained us to handle rejection.” – Evan Sitler-Bates, XpertVR

“I sold maple syrup to international students going back home for the winter. Previous to that, I flipped items on the Runescape Grand Exchange.” – Hudhaifah Zahid, econommi

“I realized that I was an entrepreneur when I was 10 years old. My mom had cancer while I was growing up and I wanted to find a way to help her. She had taught me how to hand sew little pillows. I was so excited about this new skill that I decided to teach all the neighbourhood kids how to sew them too.⁣ A few days later I had an idea. With piles of hand-sewn pillows in hand, I instructed the other kids to stand at the side of the road with me. ⁣We sold the pillows to every car and person who passed by our street.⁣
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At the end of the day, we had made the local paper and $1000 to which we proudly donated to Cancer Research. That day I realized anyone at any age in any circumstance can make an impact. Everyone has the ability to become an entrepreneur and a changemaker. Even you.” – Sarah Rennick, Alli Therapy

Do you think you were born with the entrepreneurship bug? Who or what has fuelled your love for entrepreneurship?

“I like to think I was born with some sort of entrepreneurial bug. But I think three people/organizations really fueled it. Firstly, my parents. Growing up, my dad would tell me stories of running a wedding photography business or managing an apartment with my mom. And all throughout my childhood, I would help my mom and stepdad renovate the newest house they were flipping or watch as they started businesses ranging from interior design and deck building to RV rentals. Secondly and thirdly, throughout high school, I was a part of Junior Achievement and DECA. Both of these organizations have me a wealth of knowledge in business and how to work with large groups of people in a business sense.” – Evan Sitler-Bates, XpertVR

“I was born mischievous and always wanted to stand out but the entrepreneurship bug hit me on my first internship at peer-to-peer dog walking marketplace startup gofetch.ca.” – Hudhaifah Zahid, econommi

“Yes, I think it has always been there for me – though I didn’t recognize it until later in life. I didn’t understand why I was always the one coming up with the big ideas and organizing others during play as a child. My first business came to me at 18. I was on my first summer home from University. I had developed a passion for fitness. After picking up some personal training clients at a local gym I knew I could do it better. So, I went for it and opened my own studio. Within a few months I had a packed studio every day with patrons double my age. I realized from that experience that anything is possible.” – Sarah Rennick, Alli Therapy

Are there any lessons you learned when starting out on your entrepreneurial endeavour that have stuck with you?

“I feel like you learn new lessons every day you run a business but the main one that has stuck with me from the spray paint days is how to handle rejection. Doing door-to-door sales is gruelling so it engrained the idea that for every 100 no’s, you’ll get 1 yes. Then once you have that yes, understand what you did right so you can up your close rates.” – Evan Sitler-Bates, XpertVR

“You’re out there to measure the results, you have no control over them. Better measurements allow for a smoother journey, not the journey you planned.” – Hudhaifah Zahid, econommi

“Do something meaningful to you. You have to be able to see the bigger picture, it will be the driving force for you on the days that feel hard.” – Sarah Rennick, Alli Therapy

How would you describe your journey from your first entrepreneurial venture to today?

“A rollercoaster. It’s fun and scary at the same time but if you’re lucky have some awesome people riding alongside you!” – Evan Sitler-Bates, XpertVR

“I’ve learned that the journey is never linear. It is full of ups, downs and unknowns. I’ve learned to stay open-minded and to be willing to pivot. At the start of my journey I made most decisions on positive results but now, I make most decisions on data. I try not to become biased and to constantly challenge the results at hand. I’ve learned it’s really easy to miss things that aren’t working and data is the only factor that will give you that true result.” – Sarah Rennick, Alli Therapy

“Challenging and exciting. I derive joy and satisfaction with every milestone achieved.” – Abiodun Adekunle, SleekScore Inc.

What is or will be your first lemonade stand? Dare to take the jump, and who knows what you’ll end up with, whether it be a high-growth tech platform or a Grammy award-winning album!

Ready to quench your entrepreneurial thirst? Check out DMZ’s startup programs here.