Nerd Culture

Why TEDx Fountain Hills Speaker Olenka Cullinan Wants You to Stop Overpreparing

Courtesy of Olenka Cullinan
Rising Tycoons CEO Olenka Cullinan returns to TEDx, speaking about the advantage of starting a venture unprepared.
If the phrase “you’re trying too hard” sounds like a logical reason for failure, then the theme of Rising Tycoons CEO Olenka Cullinan’s TEDx may not seem counterintuitive at all.

Cullinan is one of four millennials in a lineup of seven scheduled speakers at the 2017 TEDx Fountain Hills event on Saturday, January 28, at Fountain Hills High School, 16100 East Palisades Boulevard. An educator by profession, Cullinan will expound on her premise that young people shouldn't wait too long for the “perfect moment” to begin their entrepreneurial ventures. Instead, they should jump in and begin, even if they feel unprepared.

“Truth is, all great innovators have the courage to enter situations unprepared because one cannot prepare for the unknown,” says Cullinan, who attributes her success to always starting unprepared.

Cullinan quit a teaching job at Gateway Community College and used $2,000 in personal savings to launch her company, a for-profit education and mentoring organization called Rising Tycoons. “I remember giving my first speech, and I didn’t have a business card or a website,” she says. “You don’t always have to be prepared at a perfect level.”

Rising Tycoons offers a leadership, entrepreneurship, and personal development program for high school students and young adults up to age 23. Cullinan, whose first TEDx talk was in 2015 at Thunderbird School of Global Management, will speak this year in an “Oprah-style” couch chat format with TEDx Fountain Hills organizer Alysia Dahir about her experiences since her first TEDx talk.

Since that time, Cullinan has worked with students from 21 countries on a teen entrepreneurship competition through a partnership with SAGE Global; expanded Rising Tycoons training programs into three additional states and plans to take the program nationwide this year; ran the first Phoenix Youth Entrepreneurship and Leadership Summit with Grand Canyon University; and co-authored the book Passionistas: Tips, Tales and Tweetables From Women Pursuing Their Dreams (available on Amazon in paperback and for Kindle), which was recently featured on Huffington Post. She now also serves as a national STEM entrepreneur accelerator director with partner organization Base 11, and mentors Venture Devils startups for Arizona State University.

"We often wait for that perfect moment in life — how we prepare for everything,” says Cullinan. “We want it to be perfect before we launch a company or start a new opportunity, but in reality, life is never perfect. So if you start first — start making decisions, stop waiting for the perfect moment, and jump into opportunities, that’s how your life changes. Not by sitting and outlining a perfect plan and perfect timing. For most of my life, including this company that I’m running, I’ve never started anything at a perfect time. I’ve never come prepared.”

Rising Tycoons Academy’s 16-week intensive program culminates in students giving three-minute pitches Shark Tank-style to local CEOs and other top executives. At the end of each session, one cash prize of up to $700 is awarded to support implementation of the winning student’s business idea.

click to enlarge CEO Olenka Cullinan attributes her entrepreneurial success to beginning unprepared. She explains at TEDx Fountain Hills Jan. 28. - COURTESY OF OLENKA CULLINAN
CEO Olenka Cullinan attributes her entrepreneurial success to beginning unprepared. She explains at TEDx Fountain Hills Jan. 28.
Courtesy of Olenka Cullinan
Cullinan hails from Tula, an industrial city in Russia. Her parents divorced when she was a freshman in high school, and to support the family her mother started a wine-making business, the family's sole source of income. Though she recalls frequently having nothing in the refrigerator but bread and milk during her teen years, Cullinan's mother paid for her to be tutored in English. By age 14, she was assisting her entrepreneur mother with the business, translating documents, and interpreting at negotiations. After high school, Cullinan says, she moved to the U.S. with $450 in her pocket that she borrowed from her uncle. She worked three jobs to finance her bachelor’s degree at Loras College in Dubuque, Iowa, then went on to get a master’s in Russian and Eastern European studies at University of Arizona.

“My brother and I wanted to do anything but be entrepreneurs,” says Cullinan. “He went into the army and I became a teacher.”

Still, entrepreneurship came back to claim Cullinan, whose coaching centers around what she calls “success skills.”

“If skills are learnable, then success is learnable, too,” says Cullinan. “I see success as a step-by-step process, where you apply a series of skills and take it from the dream to whatever you want it to be.”

For tickets and additional information on the 2017 TEDx Fountain Hills event on January 28, visit