Interested in starting your own entrepreneurial journey but unsure what to expect? Then read up on our interview with Olenka Cullinan, Founder of iStartFirst, located in Scottsdale, AZ, USA.

What's your business, and who are your customers?

iStartFirst is a women empowerment brand with a twist. Our goal is to empower women into action: how to take your life, avoid burnout, and maintain or scale your business. We help women realize that they can have the "so-called" elusive balance and joy while growing the companies and impact that makes them feel fulfilled. We do that for different levels of female-founded companies:

  1. Executive Women peer Mastermind "Live for Livin" - a virtual invitation-only small peer-based model group for executive women with an executive coaching add-on. It's a place to feel safe to vent, unwind, recharge and grow.
  2. 1-1 Coaching - a virtual 3 or 6 months coaching program for mid-size and up-female-founded companies to hand-hold their scale to the next 6 figures with weekly accountability check-ins and monthly expert calls.

Tell us about yourself

I am a multi-business owner, a global consultant, and a mom. I have transformed thousands of clients since I began coaching and speaking in 2010. Focusing on what makes life balanced and joyful, I love helping women build a life on their own terms. I help companies globally implement Gender EQ strategies, innovate strategic planning and optimize productivity.

I have been named Top 10 Coaches in 2021 by Yahoo News. I have worked with top companies globally, delivered 2 TEDx talks, published 2 Amazon bestsellers, was nominated Top 100 Women to Watch by Women's Business Journal, and appeared on CBS, ABC, Yahoo Finance, and Huffington Post. My clients gross six to nine figures and I empower you to believe that success can be fulfilling and balanced!

What's your biggest accomplishment as a business owner?

I love helping women regain their time and scale up their life and business. I've helped hundreds of women-founded companies grow 22-41% yearly with the execution plans I created for them. Everyone gives women advice, but so few show them how to execute it step by step!

What's one of the hardest things that come with being a business owner?

Time. Most people are so concerned about cash flow and don't value their time. Business owners spend time on things that don't move them forward (negative productivity) and don't treat their time as a currency. Time is irreplaceable.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. Get a mentor early on - we all have blind spots, and mentors hold us accountable and provide shortcuts and advice from experience.
  2. Start before you are ready. Starting a business is like having kids; you are never in a perfect position to do it.
  3. Your company's scale will always be as you as your systems. When you don't have systems in place, even the best team cannot sustain the growth.

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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