Empowering women to stand up, show up, and take action

The guest I am bringing you this week is someone incredibly special, a woman who can scale any business and shows up real, raw, and vulnerable. Olenka Cullinan is an entrepreneur, corporate speaker, author, life coach, and badass founder of Rising Tycoons, as well as iStartFirst. Throughout this episode she shares her journey to success and how her family and upbringing shaped her, her mentality, and her drive to become everything she put her mind to. 

Listen to this episode to hear the story of how one woman uprooted her life in Russia, paved her own way to success in America (with no support or money), and how you can be empowered to do the same with your own business.

A leader goes first 

Olenka Cullinan was raised to believe that any good leader has to go first. Her mother was a die-hard entrepreneur who worked 80 hours a week and her dad was a very conservative government official. At a young age she learned how to develop a strategy for success based on minimal resources, and after her parents’ divorce, was uprooted from Russia and forced to move to Iowa with her family. 

Teaching the skills to succeed

Olenka shares how she moved to school, met a girl on the plane, and with borrowed money built a home and worked three jobs to get through college. She talks about her journey to becoming a teacher, the job she took in Phoenix teaching at a county school, and the impact the children made on her—forever changing her life. During her time teaching there, she realized the skills that students needed to learn to succeed were outside the regular curriculum—and decided to teach them. 

Scaling her first business

She discusses the beginning of her first company, Rising Tycoons, and the children she worked with that grew from a few to 10,000 within three years. As she continued to evolve and speak at conferences around the country, she began to realize the few women who were present at each one. That needed to change.  

Empowering women leaders

Today, Olenka is the founder of the iStartFirst event, workshop, mastermind, and business. She teaches women the importance of embracing both their feminine and masculine sides and to use inherent strengths to their advantage to make their dreams come true. 

Olenka Cullinan

Olenka Cullinan is a CEO and Founder of iStartFirst. She empowers women to up-Level their business and mindset via on-line Bootcamp, iStartFirst Women’s Summit, and delivering keynotes and workshops for companies nationwide & globally. Olenka has developed a “Backbone of Success”™ method that helps female leaders to take action, get paid their worth and show up like a BOSS-Babe. 

Olenka’s work globally, combined with humor and personal experiences led to her recent appearances at TEDx (twice) and made her into one of the nation’s premier consultants. She has worked with startups, corporate leaders and some of the top organizations in the country: e.g. GAMA International, Lincoln Financial, Chambers of Commerce, etc.


“I knew intuitively that if you give anybody skills, then success is learnable too.” 15:00 -Olenka

“I believe that when people are seen, heard, and understood, the possibilities are endless for what they’re capable of.” 19:00

“Part of the reason I think our education is so boxed up is because we don’t teach them compassion, we don’t teach them understanding of what the real world is like.” 22:25 -Olenka 

“To me, it’s big time figuring out what you want, because not every woman wants a 7 figure company and we have to stop driving that.” 29:30 -Olenka

“I know women who just want to be the goddamn best stay at home mom and that’s her drive, let her freakin have it, but also be a mom that’s a badass.” 29:42 -Olenka 

“There is brilliance in putting no judgement on someone.” 31:11 -Olenka

“How do I add value to you and it becomes adding value to me in the process, and then truly teaching them that that kind of collaboration is how you rise together.” 32:43 -Olenka 

“Whatever it is, you don’t have to be perfect to gain momentum and create the life you want.” 34:50 -Olenka 

“The point is not to be beautiful and amazing then do it. The point is do it in your lowest moments when you want to quit and lock away.” 38:08 -Olenka 

“We think that all those things that happened in the past disqualified me to lead, and it’s actually those things that make me more qualified to lead.” 39:03

Please follow and like us: