Meet Olenka Cullinan


Olenka Cullinan is the founder of Rising Tycoons, an organization that guides and inspires youth to become entrepreneurs and CEOs via leadership and personal development. She effortlessly inspires adult influencers and teens to collaborate and learn in fun environments that allow everyone to be themselves. Aside from coordinating exciting workshops and conferences, Olenka keynotes at school assemblies and hosts the 16-course Rising Tycoons Academy at various high schools.

What part of Arizona do you call home?

Surprisingly, I’ve lived all over the valley. I started in Phoenix and then Tucson while teaching for the University of Arizona, then lived in Peoria and Chandler, but finally settled in Scottsdale.

What was your very first entrepreneurial venture?

My mother pretty much forced me into having an English tutor since I was 7 years old. I disliked it greatly at first, but by the time I was 13 and translating documents for businesspeople in the area, I quickly figured out what a lucrative idea it proved to be! At 14, I was serving as an interpreter for my mother’s business and many other businesses in town, as well as being exposed to many incredible deals and business minds from different countries. At that time, I didn’t even realize the value of entrepreneurship or mentorship qualities I was receiving that would end up guiding my life into where I am today.

How did you come up with the idea for Rising Tycoons?

I very much wanted to be an educator, so I attended Tula Teacher Training University in Russia, and continued with my B.A. from Loras College in Iowa. I was working with teens all along, inspiring them to write poetry and to read great books. However, in my master’s program at UA, I did a study abroad course with the Diplomatic Affairs Academy in Moscow. Having met so many global business leaders and diplomats, I came back thinking about how I could inspire my students to succeed.

It was then that I saw a huge need for “success education.” Teens and millennials are not taught the step-by-step process of success; so many of them think that it requires super powers. In my opinion, you cannot teach youth entrepreneurship without teaching them the proper mindset that aids it. Neither entrepreneurship nor personal development are parts of traditional education. But if skills are learnable, success is learnable too!

What was the biggest challenge in executing this idea?

The biggest challenge is collaborating with schools. Sometimes we struggle due to the lack of funding in education, but often it’s the lack of vision and unwillingness to change. Education is a very old system, so it’s not always open to new ideas. In addition, we are always looking for companies who want to partner with our schools as educational sponsors, to expose these students to innovative, hands-on entrepreneurial opportunities. The reality is, these students are your interns today, employees tomorrow, and possibly bosses in the future.

What is your favorite part about running a business?

Freedom and ability to influence lives. I love being able to build my day and travel during the off-peak times. I always joke that entrepreneurship is when you are drawing out your next business move at midnight, but can also go get your nails done at 10 AM (#girlproblems). Plus, running my business allows me to influence lives, to have meaningful conversations, and to listen to and inspire the next generation of the next wave of entrepreneurs.

How long have you lived or worked in Arizona?

I have lived and worked in Arizona for almost 12 years. I’m so excited about how much entrepreneurial scene has developed here in the last few years. I remember going to “Fancy Fridays” with a bunch of my friends, all of us in early-stage startups—and look at us now! There’s nothing more exciting to see Phoenix, as a city, becoming the next entrepreneurial hub; we have so much talent and an amazing sense of community.

If you could only describe your city with one word, which word would it be?


What’s your favorite thing about living in Arizona?

Sunsets and the outdoors. No other place can beat Arizona’s sunsets!

What’s your least favorite thing about living in Arizona?

How spread out it is. Sometimes it feels like you are halfway to California, but you just drove from the west side to the east side of the city.

In what area do you think Arizona still has a long way to go?

Arizona’s education system is a hot topic for me. In a state with this much talent, we cannot ignore the fact that we are 47th in the nation for education. We cannot raise the next generation of talent in silos—schools cannot stand alone and work in silos. Continuing discussions of the 21st-century critical skills and employee talent gap need to cause action-driven plans that bring results. Education and the business community need a valid collaboration cycle to develop future workforce. While there are small strides in this area, Arizona has a long way to go. Truth is, the only way to change the next generation of leaders is to change their mindset and skills today.

The foodie scene is growing bigger and bigger by the day here in Arizona. What is your favorite place to get breakfast in your city?

I am a big fan of clean eating and great coffee, so Original ChopShop Co. in Scottsdale is one of my favorites. However, Pomegranate Café in Chandler is absolutely worth the drive: scrumptious and guilt-free!

What’s your favorite place to grab lunch?

I love FEZ. Amazing vibe, super fun people, fantastic service and few other places in town can top their salad choices! Not to mention the fact of how giving the owners are in the community!

Image by Richard + Bauer Architecture.

What’s your favorite dinner spot?

This question always leaves me perplexed, as it depends on my mood. Hero Sushi is probably the best dinner; it’s a small authentic Japanese restaurant with top-quality sushi and incredible chefs.

What’s your favorite place to work in your city aside from your office?

Altitude Coffee! I call it my “uber-productive” spot. Have you seen the view? I still write there at times, outside of simply doing work. How can you not get inspired by the waterfront, the birds and the possibly best quality coffee in town?

Best place for a meeting over drinks?

The Henry. I know it’s become the “it spot” for many, but they just have the vibe—vibrancy meets business.

What is your favorite memory from Arizona?

Outside of my daughter’s birth at Chandler Regional, the day Rising Tycoons was born. I was in Cartel Coffee with a friend, who came up with the name “Rising Tycoons.” I remember my feelings: the excitement, the disbelief, and the possibility that I felt in the air. I knew that I had just found my life’s mission.

What is something about living in Arizona that only a local would know of?

I would say there’s a misconception that it doesn’t get cold here. I know we are not NYC, but they do sell boots and sweaters here for a reason. And yes, I sometimes do look forward to wearing them.

Any tips for new Arizona residents?

Dive into the community! Meet new people, join groups, become a part of the #yesphx movement. That’s the beauty of the Arizona entrepreneurial scene: it’s young and pliable and has plenty of room for people to add new flavors. Explore the outdoors—there’s so much to do and  see. Don’t let the heat stop you from embracing the mountains and the parks.


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