Olenka Cullinan: Leadership Feature

leadership feature Nov 14, 2016

Olenka Cullinan is a CEO and Founder of Rising Tycoons. Teen expert, inspirational speaker, and teen success coach, Olenka has developed a “Backbone of Success”™ method that helps teen leaders become successful in school, life and the world. It combines three essential skills: leadership, entrepreneurship and personal development, which turn teens into mindful tycoons!

Having been trained by the top achievers such as John Maxwell and Darren Hardy, Olenka strongly believes that the pursuit of success with happiness is what creates goals, vision, and destination for the teens. Olenka has become one of the nation’s premiere motivational speakers and teen experts, as recently demonstrated by her speaking appearance at TEDxYouth. Olenka’s newest achievement with RT is Rising Tycoons Academy (RTA) in Arizona.

Olenka is a great example of what it means to be a MillenniaLeader. We had the pleasure of speaking with her about her leadership and her passions. Our conversation was very uplifting and inspirational because of her passion for developing young leaders.

Here is our full interview with Olenka Cullinan with commentary by Randall Garcia of MillenniaLeadership.


Q: Define leadership in your own terms.

Olenka: Leadership is action. It is the amount of impact that you create in the area you lead, and how you use your values to inspire others do and be better.

Randall: Yes, leadership must have action. You can't lead by sitting on the sidelines and watching. You have to be actively engaged in the lives of those you lead.


Q: What are your 5 core values as a leader?

Olenka: Authenticity (trumps everything), work ethics, resilience, desire to always grow, purpose (focus) and passion.

Randall: Authenticity is also one of my core values. As millennials, I believe we have the ability to see right through those who are fake. You must be transparent as a leader, people respect that!


Q: How can a leader fail? Tell me about a time when you failed as a leader (and what you learned as a result)

Olenka: A leader can easily fail by his/her inability to believe in people they work with. Obviously, when it’s your business/project you put your heart in soul into it. Best delivery, however, happens in collaboration. Your goal is to inspire people who work with you to become leaders in their own domain. Early on, when I brought my first assistant to Rising Tycoons, I struggled hard to let go. Then something ironic and funny happened. We were preparing for a large VIP event, and I asked her to personally follow up with our guest list. However, I insisted to follow up myself with 20 top leaders in the community. Imagine my surprise, when I received a call from my assistant the next morning, horrified, because while I was sending out my emails to the 20 VIPs, tired and unfocused, I never changed the names of organizations to customize the content. Probably the absolute best lesson of my life: as a leader your goal is to inspire others into action, not to lead for them!

Randall: We all have those learning lessons along the way. You can read books, listen to podcasts, and take mastermind programs, but nothing prepares a leader more than experience. Sometimes you have to learn the hard way and that's okay. As leaders, we have to realize that we won't be perfect, we have to learn and grow from our mistakes.


Q: What is the most difficult part of being a leader?

Olenka: One of the most important things as a leader, in my opinion, is to preserve your focus. I love meeting new people and learning of new opportunities, but often, as a leader you have to say “No.” The amount of “Nos” is almost as important as the amount of “Yeses”. I can think of plenty of times when I had to sacrifice all of my time for one-focused project, which means lots of people, events and opportunities did not make it on my calendar.

Randall: Yes! Focus is key! Without focus we can get distracted by projects and meetings that don't directly contribute to our mission. One of the biggest lessons that I have learned is the art of focusing in on one thing and giving it 100% effort. Your results will be so much better with full attention because your effectiveness improves with focus!


Q: How do you measure success for you as a leader?

Olenka: The amount of lives impacted is how I define legacy. Leadership is action. So I think success to me is to see more leaders being born who can go and turn their dreams into lifestyles. It’s not about publicity or being on stage or limelight – it is 100% about lives touched in a positive way.

Randall: We are here to positively impact our world, when we talk I can hear it in your voice. You have an absolute passion for leading others.


Q: Have you ever taken on a job that you were unqualified for?

Olenka: Yes, it’s called being an Entrepreneur! ☺ I was an interpreter for my mother’s company when I was 14. I remember how blown away I was being in the room, negotiating with some brilliant and ruthless business people. When I started Rising Tycoons, after working for educational institutions for almost 10 years, I remember meeting with CEOs, thinking, “I have no business of doing business with these people!” Luckily, one of my mentors, early on, advised me to always go after the biggest person in the room. “I would rather you get rejected by greatness, then be accepted by mediocrity,” stayed with me throughout all my career moves.

Randall: Wow, that is great advise. I love that. Yes, I have always told myself that I wanted to always be the "dumbest person in the room," not because I am dumb, but because I wanted to surround myself with intelligent people that I respect and want to be like. It really helps you sharpen your skills.


Q: How do you view the millennial generation?

Olenka: I think Millennials are resourceful, creative and vibrant independent thinkers who value life outside of work. Millennial generation is technology-oriented and is always on the lookout for how to challenge the status quo, how to do things in a smarter way and to propel to their goals quicker. With a fair amount of guidance, Millennials thrive in the workplace and become one of the most valuable team players or leaders. They have brilliant minds and are willing to inspire others because they are vocal about their needs!

Randall: I totally agree with your assessment. Millennials are different than any other generation and it is important for leaders to recognize the value in leading this generation.


Q: How do you think the millennial generation is perceived?

Olenka: There are plenty of stereotypes regarding the millennial generation: they have unrealistic expectations, they are not loyal to employers, they don’t value jobs and they have a sense of entitlement. And don’t forget the fact that some consider them self-centered. I personally think individuality is a strong value for our generation, which should not come as a surprise as we were brought up to question everything and are not smitten by authority figures.

Randall: It's unfortunate that people lump an entire generation into one category. As you and I are both millennials, we have definitely risen above these stereotypes and have done great work as leaders. One of the biggest reasons why MillenniaLeadership exists is to break these negative stereotypes and inspire a new generation of leaders. I believe there's a healthy anger within the millennial generation to prove everybody wrong.


Q: Why are you so passionate about leading millennials?

Olenka: Outside of being a millennial myself, which allows for experiential knowledge of dealing with misconceptions, I think that no other generation beats us out in optimism and appreciation for opportunity, regardless of circumstances. Millennials are flexible and resilient, and understand a sense of purpose! Millennial generation has an urge for disruption in them, and once given the proper tools, can inspire others into purpose-driven changes in the community and the world! Millennials can literally be the change-makers in the world, and have fun while doing it!

Randall: I can agree with you here. There is so much potential from within our generation and you see it! It's up to leaders like you to impact our generation in a positive way. Thank you for doing what you do and for contributing to the millennial cause!

One of our favorite things about Olenka is her passion for leading, but even better, she backs up her passion with super intelligence.

Be sure to follow her at @OlenkaCullinan and @RisingTycoons on Twitter and Instagram!

Websites: Rising Tycoons and Olenka Cullinan


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