The Journey of Olenka Cullinan, CEO and Founder of iStartFirst

Helping Women Achieve Balanced Success

Meet Olenka Cullinan, a remarkable entrepreneur and advocate for empowering women to reach their full potential in both their personal and professional lives. Olenka is the Chief Sparkle Officer and founder of iStartFirst, a company designed to help women reclaim their time, scale their businesses, and elevate their mindset. She firmly believes that women approach business differently from men, emphasizing the need for a balanced approach to success. Olenka’s journey is deeply rooted in her personal experiences, growing up in Eastern Europe and witnessing her mother’s challenges in maintaining a work-life balance. Inspired by her own story, she has dedicated her career to supporting women in their entrepreneurial endeavors.

In this exclusive interview, Olenka shares insights about her background, the driving force behind her work, and her commitment to helping women find fulfillment and success without sacrificing their lifestyle. With a focus on manifesting positive change and fostering a supportive community, Olenka’s message and mission are inspiring countless women to “sparkle up” and redefine their paths to success.

Join us as we delve into Olenka Cullinan’s incredible journey and her unwavering dedication to empowering women to create a harmonious life filled with achievement and joy.


Can you start by telling our readers a bit more about you and share anything not already known from your online presence?

Certainly. I am the CEO and founder of a company called iStartFirst. It’s designed for women to fully embrace their potential, reclaim their time, and elevate both their businesses and mindset. 

I believe women approach business differently from men, often getting overwhelmed with various responsibilities, losing track of time, and forgetting their initial motivations. I built my business to be what I needed as a woman business owner when I was younger. I was raised in Eastern Europe, where my mom ran a company for 37 years.

 I vividly remember writing a letter to Santa when I was five, asking for more time with my mom. Despite her being an inspiring role model, she struggled with work-life balance. I didn’t truly connect with her until I was 14 when my brother and I joined her in the business, traveling across Europe, negotiating multimillion-dollar contracts. We didn’t build a mother-daughter relationship until later in my life. 

When my daughter was born, I committed to being proof that women can balance life and business differently. I embarked on this journey to help women scale their businesses while enjoying joy, fulfillment, and success without guilt. I’ve been coaching women for over 10 years, working with hundreds of companies, giving TEDx talks, and writing Amazon bestselling books. I started with a simple message: all you have to do is start, emphasizing that women often delay taking action, seeking perfection before launching. Building a business is like childbirth – messy and unpredictable, yet we deliver beautiful results.


Can you tell us about any special talents or hidden facets that people might not know about you?

While many know me for one-on-one coaching with professional and executive women, I also consult with large companies, focusing on gender intelligence. This involves bringing men and women together to optimize team dynamics. Additionally, I used to ghostwrite for CEOs. I’m passionate about writing and public speaking, which was my initial path before building my business.

That’s intriguing. If you could offer advice to your younger self, what would it be?

I’d advise my younger self to ask for help. Women often struggle to say, “I need help with,” fearing it makes them appear weak. Yet, successful individuals typically have a team of supporters, mentors, and coaches. Asking for help isn’t a sign of weakness but strength. It’s also a valuable lesson for children, teaching them it’s okay to be strong and ask for assistance.

That’s a valuable lesson, indeed. Can you walk us through your current offerings for women to join your programs and courses?

I have three main offerings. First, I work one-on-one with women, including business owners, female founders, and C-suite executives, to help them become the best and happiest version of themselves, whatever that means for them. 

My largest offering is the ‘Live for Livin’ Mastermind, a year-long group program designed to help women create a balanced lifestyle while scaling their businesses. It includes monthly group sessions, mentorship, accountability partners, and quarterly one-on-one sessions with me. Lastly, I consult with corporations, training their teams to foster female leadership and gender intelligence.

What’s the key message you want women to take away from your work and courses?

The main message I want women to retain is that they don’t have to sacrifice their lifestyle, relationships, or well-being to achieve business success. It’s possible to have fulfilling success with balance.

That’s a powerful message. Do you have any daily or weekly rituals or practices that set you up for success?

I have a morning and evening routine, which I consider my bookends for the day. I meditate and focus on gratitude in the morning. I avoid touching my phone first thing in the morning and engage in meditation. In the evening, I read, journal, and reflect on the day. I practice the law of attraction and manifestation, helping me stay present and grounded.

What are you currently manifesting?

I’m currently manifesting the expansion of my ‘Live for Livin’ Mastermind to reach thousands of women all over the world. I want to help more women create balanced lifestyles without guilt, burnout and overwhelm, while scaling their businesses.

Do you have any non-negotiables that contribute to a brighter life?

My two non-negotiables are avoiding negativity and staying in the present moment. I always focus on finding the silver lining and maintaining a positive attitude. I continually remind myself to be present here and now, as it’s easy to get lost in the past or future.


For more information, visit her offers here.

Follow @OlenkaCullinan on Instagram.

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