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Beyond Barriers Podcast: Changing the narrative & challenging business misconceptions

by | Dec 19, 2023

Stephanie Nadi Olson

Originally posted on Beyond Barriers Podcast on December 13, 2023.


Does this sound familiar? You’ve been told to simply work harder and longer hours to achieve success in your business. But despite your efforts, you’re still struggling to challenge misconceptions and create change in your industry. This ineffective action might leave you feeling frustrated and stuck, unable to make the impact you desire. It’s time to break free from this cycle and discover the power of storytelling to overcome misconceptions and change perceptions, paving the way for meaningful transformation in your business.

Prepare to be captivated as we introduce the visionary force behind We Are Rosie, Stephanie Nadi Olson, whose innovative prowess as the Founder and CEO has woven a tapestry of possibilities in the realm of flexible talent. The We Are Rosie platform connects over 25,000 marketing freelancers to project-based work with renowned brands such as Microsoft and Delta. Get ready to delve into the vibrant world she has crafted at the intersection of talent and pioneering brands.

In this episode, you will be able to:

  • Challenge and overcome misconceptions about freelance talent to elevate your business.
  • Harness the power of storytelling in business to captivate and connect with your audience.
  • Learn the art of building relationships for entrepreneurial success and long-term growth.
  • Discover the impact of leveraging networks for personal and professional advancement in the business world.

Stephanie shares a compelling journey of resilience and determination that began in her childhood. It reflects a profound understanding of the complexities of inequality and a steadfast commitment to challenging societal norms. Stephanie’s compelling story serves as a testament to the transformative power of storytelling in dismantling misconceptions and fostering impactful change.



[00:00] Introduction to Beyond Barriers podcast

[00:35] Powerful Quote from Stephanie

[02:03] Early Life and Competitive Spirit

[04:31] Aware of the haves and have-nots from an early age

[06:09] Observing Resource Distribution

[11:26] Birth of We Are Rosie

[15:49] Overcoming Resistance to New Ideas

[22:13] Celebrating Small Wins

[25:06] Bootstrapping and Sacrifices

[28:31] Impact of COVID-19

[31:13] Balancing Work and Personal Life

[31:51] Embracing Seasonal Changes in Life and Work

[32:39] Building a Supportive Network

[36:45] Building Influential Relationships

[40:09] Lightning Round Questions

[42:42] Stephanie’s Parting Words of Wisdom



I set out to build a better way to work. – Stephanie Nadi Olson

I realized that there were a lot of people that were being underestimated and marginalized within the marketing industry, and I set out to build a better way to work and a way to allow people to be treated with dignity and respect regardless of what’s happening in their life. – Stephanie Nadi Olson

I personified the Rosies, which is what we call our freelance talent, and I did it through storytelling, which I think is so powerful when you’re trying to create change. – Stephanie Nadi Olson

I love helping people who are overlooked, underestimated, and marginalized. Those were the moments that I was just in love with life. – Stephanie Nadi Olson

The difference between you and the people that are achieving all their dreams is that they just went for it. – Stephanie Nadi Olson


Lightning Round Questions:

Q: What book has greatly influenced you?
A: “Discovering Your Strengths” by Donald O. Clifton and Marcus Buckingham

Q: What is your favorite inspiring quote or saying?
A: I had to make you uncomfortable, otherwise you wouldn’t have moved.

Q: What is one word or moniker you would use to describe yourself?
A: Restless

Q: What is one change you’ve implemented that made your life better?
A: I moved to the country.

Q: What power song would you want playing as you walk out onto a stage?
A: “9 to 5” by Dolly Parton



Stephanie Nadi Olson is an innovator and disruptor, aiming to change the world’s perspective on the future of work and what it means to be inclusive in the workplace. Olson, a former advertising executive, founded We Are Rosie in 2018, before the pandemic made remote and flexible work mainstream. She was the company’s CEO from 2018 – 2022, overseeing its rapid growth and influence. In January, 2023, Olson moved to Executive Chair of the Board of Directors to focus on propelling We Are Rosie’s mission and forecasting what’s next while leading the Board of Directors.

During her advertising career, Olson worked with big brands and major tech companies, including Microsoft and AOL, as well as start-ups. She developed a unique 360-degree view of industry practices and saw the need for transformation. Olson used this insight to create the foundation for We Are Rosie, a human-centered approach to marketing that celebrates diversity and facilitates work-life harmony, while creating access, opportunity and wealth for those who choose a flexible career path. In less than five years, We Are Rosie now works with more than 25 Fortune 500 brands, including Microsoft, Meta, IBM and Bumble, as well as all six major advertising holding companies. Its community of marketing talent (aka Rosies) currently stands at more than 20,000 and its reach is felt in all corners of the marketing world.

Last year, Olson was inducted into the American Advertising Federation’s Advertising Hall of Achievement and was an EY Entrepreneur Of The Year® 2022 Southeast Award winner. She was named to the Forbes Future of Work 50 list, was one of Atlanta Magazine’s 2022 Women Making a Mark and was named one of Atlanta Business Chronicle’s Most Admired CEOs. In addition, she was named a 2022 Aspen Ideas Festival Fellow. In 2021, she was named to the EY Entrepreneurial Winning Women class. In addition, Olson was named AdAge Visionary of the Year 2020, was recognized by Adweek in the 2020 Creative 100, was named World Changing Woman 2020 by Conscious Company, and was awarded Global Entrepreneur of the Year 2019 by the Stevie Awards. We Are Rosie was recently ranked #232 on the Inc. 5000 list of the fastest growing privately-owned companies.For more information visit

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