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.
You have recently been writing about the toll that being a founder took on your physical and mental health; can you share more about that here?
Since I moved into an Exec Chair role a few months ago, I’ve been telling people that I am currently in Founder and CEO recovery. Not to take a single thing away from my entrepreneurial journey- it has been absolutely joyous and life-giving and exciting for me these past several years, but I also want to be really honest about the toll it takes to build a business as quickly as we did at We Are Rosie. We bootstrapped the company from an idea to a partnership with a Private Equity Firm in less than four years. This meant a whole host of “CEO illnesses” that came along with the personal, physical, and emotional sacrifice it took to accomplish that success.
We talk a lot about seasons of life and career at We Are Rosie, and how we need to normalize having seasons. I am in my wintering phase- recovering from the previous seasons and gathering all my energy for whatever comes next.
I mean, at a national level, the U.S. was “founded” by folks who set sail to find a better future- hustling for a better world, literally. Globally, we have historically been the place people can go for opportunity and new beginnings. All you have to bring is a work ethic! It’s so ingrained into our culture, our ethos, the media we consume here. And I think everyone likes to see people getting after it in that way. It’s fun to cheer for people who are actually putting in the work.
Also worth mentioning, I think that people really love this narrative of “hard work can get you anywhere” in America. It’s true, to an extent, but it holds far more true for people who aren’t marginalized and discriminated against at every turn.
Get real about what it will take to achieve your goals, and get real about what sacrifices you can and cannot make to get there.
I am really lucky that I had the foresight to know that building We Are Rosie would be an absolute slog at times. I wanted to bootstrap, I wanted an exit, I wanted to grow quickly, I wanted to touch thousands of lives. This was never intended to be a small endeavor. One of the smartest things I did was sit down with my husband at the very beginning and make sure I had him on board. We talked about how he would need to be the primary caregiver for our children for a few years, how I wouldn’t be able to go to doctor’s appointments for the kids, manage the house, etc. We really talked through it all. And bless this man for saying, “Steph, go do it. I’ve got you.” He is absolutely a stakeholder in this business as he enabled me to do all the crazy things you need to do when building a business.
I also built an advisory board in the early days- people who had knowledge that I was missing and some people who had bootstrapped big tech companies before me. These folks kept me focused, on track, and from having a complete meltdown more times than I can count. Building a community of people who have your back is so important.
I am still in it, but it’s getting way better. When I was building the company and trying to maintain some (oftentimes pathetic) semblance of being a present mother, I would wake up at 4 or 4:30 a.m.every day. This gave me time to get work done before my email, DMs, texts, and calls started blowing up for the day. It allowed me to clear my head before the kids woke up- and getting that jump start meant that I could often be present at the start of their day. This went on for years, and eventually my body learned that 4:30 is wake up time.
I’ve had to get really serious about setting proper conditions for sleep in order to change this pesky habit. I’ve cut out caffeine, alcohol, and tv before bed. I am basically unwilling to let anything get in the way of sleep- and it feels so wonderful. I walk around now like “Is this how other people feel every day? Rested and not struggling to hang on?? I love this life!!”
If you don’t take the break you need, your body will eventually do it for you. And I promise you it won’t be convenient.
I admire Linda Yaccarino, as she’s just taken the CEO role at Twitter. I’ve had the pleasure of getting to know Linda the past couple of years. She’s a powerhouse, of course. And she’s a wonderful, empathetic leader. It’s a shame that so many women only get the CEO (or other leadership) opportunity when the shit is hitting the fan and the chances of failure are so high, but I have so much faith that if it can be done, Linda can do it. She was really courageous to give this role a try. And if it doesn’t work out, I sure hope she gets a job as CEO of a company that is prepared to thrive and not simply looking to survive.
Lately, my Oura ring! I have some sensory issues and apple watches are too clunky for me, so I’ve never had one. As I am deep into my CEO-recovery journey, I love the data I get from my Oura ring about sleep and readiness as I wake up each day. I also move my butt so much more when I have this thing on. I feel like the robots are watching and I better hit that steps goal!
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. Its community of marketing talent (aka Rosies) currently stands at more than 25,000 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 anEY 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 www.wearerosie.com.
