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BEYOND 8 Figures Podcast: What Does the Future of Work Look Like with Stephanie Nadi Olson

by | Jun 4, 2021

Stephanie Nadi Olson on BEYOND 8 Figures Podcast

Originally posted on BEYOND 8 Figures Podcast, June 4, 2021.


Today, we talk about the future of work with Stephanie Nadi Olson, who is reshaping the marketing industry. The future of work is independent, flexible, remote, and non-hierarchical. Stephanie is creating it with her company We Are Rosie and joins us today to tell us all about it.

If you are interested in challenging the existing structures, and if you don’t want to be left behind in the past, tune in to today’s episode to find out how you can build a business that makes your employees’ and clients’ lives more fulfilled.

About our Guest:

Stephanie Nadi Olson is the founder of We Are Rosie – a network of 6,500 marketing freelancers who are currently experiencing the future of work. She started her business with $10,000 and turned it into a 7 figure machine.  When covid hit, she lost 80% of the business overnight. However, by staying determined and faithfully betting on the success of her team the company doubled in size by the end of 2020.

Check out the full episode here.


On the episode: 

  • How working at Microsoft helped Stephanie reimagine work. – 01:52
  • How she spent her time after quitting her high-paying job. – 03:16 
  • The moment she realized how she can change the way work is. – 05:48
  • How ignorance can be your best friend. – 07:03
  • 3 big challenges that agencies and brands must deal with (and how she solved them through We Are Rosie). – 10:00 
  • Why remote work is the right thing to do and why you should do it too. – 11:38 
  • How you can take inclusion further and how to avoid wage theft. – 13:44 
  • 3 things that stop traditionally employed people from becoming freelancers. – 15:06
  • If you want to run a global operation, listen to this first. – 16:40 
  • The mindset needed to move from $10,000 to a business that transforms the way work is – 20:18 
  • How COVID took away 80% of her business overnight, yet she doubled the size of her business by the end of 2020 – 21:44
  • The biggest challenge of business growth is about people management- 22:45 
  • The conversation about the future of work must center around THIS key issue. – 26:14 
  • Why Stephanie Olson’s company is called We Are Rosie and her vision for more humane work – 28:50 
  • How your responsibility and your legacy are tied together – 32:25 
  • Thinking of giving back as giving back to family – 34:03 
  • The future of We Are Rosie: Global Expansion and more – 35:28 
  • Are you freelance curious? – 37:49 
  • Amazing lessons from today: having beginner eyes – 38:30 
  • Amazing lessons from today: Leveraging challenging situations- 39:28 
  • Amazing lessons from today: Centering legacy around family – 41:50  

Key Takeaways:

  • Getting paid a high salary at a young age can be a curse and make you afraid of taking entrepreneurial risks. 
  • Building with ignorance, building without preconceived notions, can allow you to be more creative and forward-thinking. 
  • There is a massive mistrust between brands and agencies that runs both ways. 
  • People want to work in a more agile capacity. 
  • Remote work is inclusive. When you insist that people come into the office, you exclude lots of talent from your pool.
  • The foundation of how we insist work happens is very exclusionary. COVID-19 has proven that remote work is effective. This is an opportunity for companies to reconsider how they work. 
  • The biggest impediment to traditionally employed individuals who want to become freelancers is the consistency of pay, the consistency of work, and insurance. 
  • The operational lift required to run an equitable and inclusive business globally is heavy. For example, there are 1,800 laws in the US governing labor. Navigating this is a large challenge. 
  • The bigger you get, the more fear may play in your decision-making. 
  • Even if not everyone in your team agrees on the same thing, it is vital that everyone feels heard. In environments where people don’t feel heard, creativity and innovation will be stifled.  
  • When we talk about the future of work, if we are not discussing freedom of choice then we are not approaching it correctly.  

How ignorance can be a gift when building fresh ideas

“I used a lot of common sense to build this business. I know it sounds really simple but I didn’t have any of these kinds of ideas in my head about things that were immovable. Like, “we have to do it this way, and we have to scope this way, and the talent has to be structured this way, and this has to be billable, and all of these ideas. All the stuff I’ve learned about agencies over the last three years, I didn’t know!  Using the amazing gift of ignorance and being slightly naive to say, if I was going to build something to replace an agency or to be the next iteration of an agency today based on everything I know – what would that look like? And I got to just build it from scratch with none of these preconceived notions and I think there were some heavy learnings from that but I would say by far if you talk about our growth that we’ve grown so fast last 3 years I think it has to do with this idea of being able to build without having any ideas of what it should look like or even bias” – 08:28