By Mandy Holmes
Photos by Claudia Johnstone
Olenka Cullinan is passionate about empowering women to level-up their businesses and mindsets via her 30-day online challenge-style bootcamps, speaking engagements, and #iStartFirst Summit. As a best-selling author and success coach, Cullinan has dedicated the majority of her professional career to helping people, especially millennials, develop the skills needed to succeed in entrepreneurship, leadership and business.
The mindset that drives Cullinan has been with her for many years – when she was 14, her mom gave her a card that said, “Always play by your own rules” and she never stopped doing just that. After moving to the U.S. from Russia at the age of 19 with $450 of borrowed money in her pocket, Cullinan quickly learned the value of hard work and perseverance. While working three jobs with no financial aid or scholarship to pay for college and basic living expenses, she maintained her position on the dean’s list every semester and graduated with several degrees, including a master’s in European studies.
With entrepreneurship in her blood thanks to a mother who built a wine-making business, it was only a matter of time before Cullinan started her first company. A mom herself, Cullinan launched Rising Tycoons when she saw that high school and college students were struggling with the basic life skills that would enhance their business trajectory.
“They were being trained to pass tests, but not provided the tools to spring them forward in their careers,” she says.
Rising Tycoons was started as a youth-driven company for teens that taught them skills through entrepreneurship and leadership training. In 3 1/2 years, she helped more than 10,000 teens and 1,500 educators through the program, but she knew she could do even more.
Around the same time, Cullinan noticed the glaring gender gap in the business and leadership worlds and turned her focus to helping women step into the spotlight.
“While I wanted to fix the gender gap in business, I knew nothing about working with women,” Cullinan says.
After creating and implementing the hashtag #iStartFirst into her female-geared speeches, the hashtag’s popularity grew like wildfire. Soon, the inaugural #iStartFirst Summit took place, followed by online bootcamps limited to 20 ladies at a time and in high demand today.
“I realized that if we, as women, are willing to go through bootcamps for diets and exercise, we can most certainly go through one for business and mindset,” Cullinan says. “And to do it in a collaborative and safe environment, in competition with yourself only and no judgment, I could create something that would make the business map easy.”
When Cullinan was invited to co-author her first book, Passionistas: Tips, Tales and Tweetables for Women Pursuing Their Dreams, it solidified that working with women is what she was meant to do.
“I met the most incredible group of talented, brave, passionate and brilliant ladies, and I realized that I had to inspire more of them,” she says, noting that a large part of her philosophy is to teach women to stop preparing for the perfect moment and start doing instead.
Cullinan has always had the natural ability to help and inspire people, and that’s how the #iStartFirst Summit evolved. The summit is a one-day transformational event of workshops, tools and strategies to empower women into action. Watching women succeed and build their dreams is what fuels Cullinan, who explains, “It’s truly never about the spotlight; it’s always about the impact.”
As a woman in business, Cullinan believes there is still so much to unlearn from our past, our parents’ pasts, and society’s rules. She feels honored to facilitate this authentic, raw and vulnerable female movement and considers it to be a learning process, as each gender leads and runs businesses very differently.
“Women are nurturing by nature. They are givers and often need to learn to put themselves first,” Cullinan says. “When I see another woman come into her powerful self, shining her light – and I’m a part of her journey – that fills me with joy.”
Call it a superpower if you will, but Cullinan is categorically good at believing in women’s best versions of themselves before they can see it in the mirror.
With two best-selling books and two TEDx talks under her belt, the young girl from Russia with a few hundred bucks in her pocket turned business mogul is on the road to global domination.
“2019 is the year of expansion for #iStartFirst. I’m looking to bring bootcamps to other states and to launch the summit in one more city outside of Phoenix. This brand is truly a legacy for me; it’s not about me, but about the incredible tribe of women who are ready to set their journeys on fire,” Cullinan says. “On a personal note, I want to be able to have the freedom to travel and meet other inspiring women globally so I can show my daughter that she, too, can always play by her own rules.”