What Does the Future of Work Look Like with Stephanie Nadi Olson, We Are Rosie

What Does the Future of Work Look Like with Stephanie Nadi Olson, We Are Rosie

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 Stephanie Nadi Olson: 

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. 

What is the future of work?

The future of work is changing dramatically as it turns toward two major aspects: working remotely and non-hierarchical structures. These changes are reshaping traditional workplace interactions and creating a new landscape for how we approach and experience work.

Remote work has arisen as a key trend in recent years and continue to accelerate as technology and communication advances. Working from anyplace, whether at home, in a co-working facility, or while traveling, has grown more viable and accessible. This shift to remote work provides various benefits, including increased flexibility, work-life balance, and access to a worldwide talent pool. Businesses are recognizing the benefits of remote work, not only in terms of cost savings and expanded talent options, but also in terms of employee satisfaction and productivity.

Similarly, future of work is shifting away from strict hierarchical systems and toward more inclusive, collaborative and positive company culture. Non-hierarchical arrangements encourage a flatter organizational hierarchy with decentralized decision-making and more evenly distributed authority. This strategy encourages employees at all levels to contribute ideas, take ownership of projects, and participate in meaningful decision-making. Non-hierarchical structures encourage a culture of cooperation, open communication, and shared responsibility, which boosts creativity, innovation, and employee engagement.

As the future of work evolves, the integration of remote work and non-hierarchical structures will be critical in building work environments that are adaptable, innovative, and inclusive. Accepting these changes can open up new opportunities for businesses and individuals alike, allowing them to thrive in an ever-changing environment.

On today’s 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


What do you think is the future of work? What do you do in your business to join the future of work? Tell us in the comments and don’t forget to say hello if you would like to share your entrepreneurship story on our podcast. 

Connect with Stephanie Nadi Olson:

Also mentioned this episode: 

Design Pickle: Website

Connect with A.J.Lawrence:

Follow Beyond 8 Figures:


[00:01:38] A.J. Lawrence: Hi Steph! Thank you so much for coming on the show. It’s such a pleasure to have you here today.

[00:01:43] Stephanie Nadi Olson: I’m so happy to be here. Thank you for having me.

[00:01:46] A.J. Lawrence: As I was telling the audience about your amazing background and all the cool stuff you’re doing, I would love to hear, and I know our audience would too, a little bit about what led you to start We Are Rosie and the background you had that led you to that.

[00:01:59] Stephanie Nadi Olson: Yeah. So I went to school, a university here in Atlanta, at Georgia Tech, and when I graduated I was kind of dropped into the marketing and advertising world. I got my first job at Microsoft right out of school, which was pretty cool. Everyone thought I was going to be an engineer there because I went to a technical university, but I was actually the first person that they hired to work on their college hire programs. So it was a really cool moment where they were re-imagining work and it set the path for my career to have these incredible experiences that really big companies like Microsoft and AOL and startups. And I really got startup itch actually, ironically when I was working at AOL and Tim Armstrong, our CEO at the time, was acquiring startups I mean almost daily. It was really difficult to even keep up, but it was such an incredible time. I look back so fondly on that time because things were changing so quickly. The digital media ecosystem was evolving so fast as people got online more and more and more. They’re started consuming content on their cell phones. It was a pretty exciting time and I had the privilege of getting to meet all of these startup, some founders, some early employees, that had gotten acquired by AOL. And I just got that startup itch and further down the road, after several other experiences, I was so ready to start my own.

[00:03:16] A.J. Lawrence: So did you go directly to starting We Are Rosie or was there a couple of companies or a couple of ideas that you attempted first? How did that sort of play out?

[00:03:25] Stephanie Nadi Olson: It was hard. So I was the breadwinner for my family and I totally had golden handcuffs. The media business is a lucrative one and I was making great money at a very young age. I mean, irresponsible money for somebody at that age.

[00:03:40] So it was really difficult, you know, I was chasing money and I was chasing kind of the next title for a lot of my career. And so it was hard to even consider stepping out of the treadmill or hamster wheel to do something kind of revolutionary and try something new. And so when I left AOL, I did go work at a startup. It wasn’t tiny, tiny, but it was pretty small. It eventually sold to Yahoo. And that was an incredible experience. I worked with the coolest people. I really respected the founder. And then I went to work at another startup after that. And it was really that experience that I feel like the stars really aligned for me.

[00:04:15] I had recently given birth to my second daughter and I think that gave me a moment to pause, even imagine what it would be like to get off the treadmill, which was something I wouldn’t even have given myself the space to do previously and think about what am I doing with my life? What kind of legacy do I want to leave my kids? How do I want to spend my time on this earth? And it was a bit of like a crisis for me. And it actually resulted in me, it may not sound like a big deal to some people, it’s an incredibly big deal for me because stability is very important to me, but I quit my job. And I was unemployed for the first time in my life.

[00:04:49] I’ve been working since I was 14 years old. I’ve had like two or three jobs at any given time, all throughout college and all of a sudden was unemployed. And my husbands said, _’All right Steph, we can do this. We’d saved up enough money and you can go explore what makes sense for your life for six months and see if you can make something’._

[00:05:08] And I was like, okay, I’m super goal oriented. So I was like, okay, six months, I can do this. And I spent the first, just few months talking to people, A.J.. so like as soon as I quit my job, everyone was like, _’Are you okay?’_ Anyone that knew me was like, _’Is everything all right? What’s going on?’_ I got a lot of phone calls. I said, I just want to do something different with my life. I don’t know what it is.

[00:05:28] And people, I always say there’s angels everywhere, and people started making introductions to me. So they would say, _’Hey Steph, you should meet Joe. He just quit his job at Google and started this new thing to follow his dreams and follow work that was more fulfilling for him’._ And then it would be, you should meet this person and they would make another introduction.

[00:05:48] And so I’ll never forget during that time, it probably went on for about two months. And me being a very Type A person, I was like, am I accomplishing anything? Or am I just having these amazingly mindblowing conversations with all of these entrepreneurs and solopreneurs? And I remember my husband coming home and saying like, what’d you do today?

[00:06:07] And I was like, honestly, like nothing super tangible. I can’t say I achieved any goals, but I had the most incredible conversations with other people who quit their jobs to follow their dreams. And that was the beginning of me realizing there were a lot of us out there. They needed community, they needed access to opportunity. They needed clients. And those were all the seeds that were planted during that two month. It was like speed dating that eventually led to me starting We Are Rosie.

[00:06:34] A.J. Lawrence: That was agency, digital agency craziness, and kind of going up. And as I used to say, I used to make millions and millions of dollars and get tens of thousands of dollars bonuses from doing that for people. It was like, why am I doing this again? But like I left because of my second daughter. So that’s funny because I think children do become that kind of crux around which like, wait, why am I doing something around that? I can’t wait to talk a little bit about how important it is.

[00:07:01] What’s interesting is in those conversations, as someone who built and sold a couple of agencies, I sold part the last one, because I was getting frustrated with the move to go higher and bigger, and we had to keep going into larger and going after bigger companies and my talent was getting more and more expensive. Any good talent I was building was getting poached right away. Like I had friends at big agencies like we love you, you’re a great farm team.

[00:07:26] Stephanie Nadi Olson: Yeah, definitely.

[00:07:28] A.J. Lawrence: But you approach something. The benefit of agencies is not the agency model, but the outside thought that kind of consultative approach to problem solving. And I love what you did with it. How did you decide to make something a little bit, cause you were kind of jumping into this, but We Are Rosie is not a very straightforward, typical agency or you’ve created something that’s this beautiful hybrid that I’ve seen attempted before, but I don’t think I’ve seen as well-structured and as fast growing.

[00:07:57] Stephanie Nadi Olson: It’s such a good question. And I’ll say we’re not an agency. And the truth, like the very straightforward truth is I’ve never worked at an agency. And if someone asked me today, I could, but three years ago, if somebody said _’Steph, here’s a million dollars, start an agency’_. I wouldn’t know what to do. Like, I wouldn’t know where to begin.

[00:08:14] So it’s funny because we as a bootstrapped company and as a founder who has never worked in the agency space or the consulting space, I mean, I’ve worked at Jason, right? Like I’ve called on agencies my whole life. I’ve just never worked inside them. I had to use a lot of common sense to build this business.

[00:08:29] And I know it sounds really simple, but I didn’t have any of these kinds of ideas in my head about things that were immoveable. 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 these stuff I’ve learned about agencies over the last three years, I didn’t know. So a lot of it was just this 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 is you talk about our growth and we’ve grown so fast over the last three years. I think this idea of being able to build without having any ideas of what it should look like or even bias, right. Just the bias of, well, this is how it’s done at WPP so it should be similar. Like clearly they figured it out. I just didn’t know. So I literally just built it all with common sense and with really smart people on my team.

[00:09:33] A.J. Lawrence: What I find so interesting looking at it is having gone off into the wilderness and selling and been a, some virtual CMO work, a lot of advising, you seem to have approached it more from well, what do they need to get done? How does this really work? Because I’ve heard this time and time again, _’Oh, I don’t really need that’_ or _’problem with aging_’, _’Why am I always being sold this when I only need that’, _you have it nicely structured. Did that kind of go in, you were talking with different people about who had this amazing talents, but were you also talking to people looking for solutions or how did that.

[00:10:08] Stephanie Nadi Olson: For sure. So this is the blessing of me kind of growing up in sales. I sat between agencies and CMOs for my entire career for over 10 years before I started the company. So the big trend that I was seeing is that there was like massive mistrust between brands and agencies, which is so unfortunate. And it was just like, it wasn’t even a secret. Like we all just talk about it pretty, fairly openly and it runs both ways, right? Just too it can be a bit of a mess at times. And then the other big thing I was seeing was that agencies weren’t able to respond to the rise of project-based work, the way that brands needed them to, and then the big light bulb for me and all of those conversations I had in that two months where I was unemployed was people want to work in a more agile, flexible capacity. The talent wants to work this way. The agencies haven’t figured out how to enable that and the brands need talent to work in that way. So we just came in and said, we’re going to be the hub that connects people who want or need to work in a more flexible capacity to the brands. And now there are agencies who want work done in a flexible agile capacity using on-demand expertise. So I just kind of saw that big gap there. And the big moment for me was like, we make so many excuses for why we can’t do work in this way, but if we could figure it out, the talent would be more fulfilled. The people doing the work would be happier. Our industry would be more inclusive and we would be able to get work done in these sprints or project-based capacities that the brands are really like, you’re not competitive if you can’t work that way anymore right now.

[00:11:37] A.J. Lawrence: Let’s talk a little bit about how this was before things changed the past year. I dabbled, but never went as full as you did. I dabbled in like, okay, let’s part-time hiring of women on maternity leave or people who live far outside the city centers. And it seems you went full in, was that sort of the intention that you were going to be finding this overlooked geographical talent or is it just local and kind of expanded?

[00:12:03] Stephanie Nadi Olson: Yes, so we’ve been a remote first organization out of the gate. So even pre-COVID, about 95% of our work was done remote and our clients had have a really good reason for why they wanted somebody in office. And one of the big conversations that we were having pre-COVID was remote work is inclusion.

[00:12:20] And frankly, even at these big progressive media companies that I spent my career at, remote work was challenged. I’m in Atlanta, I’m not in New York. And I have been passed up for promotions. I have been straight told to my face, like, we’re not going to give you this job because you won’t move to New York.

[00:12:36] And so I had a chip on my shoulder about that. But then it went further, right, to recognize like when you’re insisting that people come into the office, what does that mean for people who have disabilities, who it may be really added an extra burden for them to have to commute daily? What does it mean for people who have mental health challenges who may want to work remotely for those reasons? What does it mean for, we have veterans in our community, who have been in combat and have PTSD. So like going into an office, it’s just not something that they can do. So we’re saying we want inclusion, but just the foundation of how we’re insisting work happens is very exclusionary. And that was a big conversation that we were having with all of our clients and they were open to it.

[00:13:16] We’re having to have a lot of conversation about it, and we had to sell it through to multiple stakeholders, but really COVID has given us the chance to say this way of working is possible. We’ve all seen that now. Like the cat is out of the bag on that front. Now the responsibility of every leader and every organization, I don’t care what department you’re in, their responsibility in this moment is to reconsider the way they’re allowing and encouraging and supporting work to be done on their team. To be more inclusive, now that we all know remote work is possible.

[00:13:44] A.J. Lawrence: What I find very interesting, kind of having dug around a little bit, you’re taking inclusion a little bit further because I’ve heard of other people who say, _’oh yeah, we hire, we allow people, we put people on projects’,_ but you’re not taking them on per se as contractors, but it seems you do go a little bit further.

[00:14:02] Stephanie Nadi Olson: Yeah. So we call all of our talent "Rosies" because there’s just so many connotations. Like it’s such a load, you’re right, like there’s loaded language for freelance and contractors and all of these different things and we’re trying to really get people to reimagine what you can do with flex talent.

[00:14:16] So our Rosies are most often W2 employees of ours. For the duration of their project, we pay them weekly. We give them full benefits so medical, dental, and vision, and these things are a big deal for us, particularly as a bootstrapped company. But it’s really important. I don’t want people working for We Are Rosie that are suffering from what I call wage theft, right? Where you have met 90 payment terms. So we’re going to use all of our power and influence that we have as a rapidly scaling organization to get the most favorable payment terms from our clients. But regardless, we’re paying our Rosies every week. I don’t need them worried about paying their rent or buying groceries. I want to make sure they’re really well taken care of so that we’re starting to dismantle some of the barriers that are put in place for people to be able to work in a more flexible capacity as well.

[00:15:05] A.J. Lawrence: I like that a lot because I know from my own experience, just the difficulty of when you’re a small, running payroll with such a craziness. I had team who wanted it every two weeks and I wanted it and it took me a long time to realize I was looking at my frustration levels of it, running it, not in paying people, but in writing it.

[00:15:23] But the team was like, we need our money faster. And I was like, _’Oh, yeah, that’s right_’. So I love that you’re doing this weekly. And was that something you were doing early on or how did that kind of

[00:15:34] Stephanie Nadi Olson: We added it. Probably we couldn’t have done it out of the gates, right? Like I started this company with 10 grands. We didn’t have the bank account to facilitate that with our accounts receivable. So we added it probably about a year and a half ago, and it just came from our internal conversations and we’re always trying to push ourselves, right? We have a million ideas we haven’t done yet, but like, what are the ways that we can better support our Rosies? And also through our conversations, we have 70, almost 7,500 people in our community.

[00:16:01] We’ve spoken to so many of these people and a lot of the people in our community are people that are sitting in a traditional full-time job who are saying, _’I want out of here. You get me a six month project and I’m gone’_. But the biggest impediment for them is consistency of pay and insurance, right? That’s not surprising. But inconsistent work, right, like just knowing that they will have additional opportunity, it won’t be a one six-month project and then the well dries up. So we’re constantly taking this feedback and from our Rosies, so we have a very high touch model and we’re in constant contact with both our working Rosies and our Rosies that we’re looking to put to work. And so we take that feedback and want to add it in, in any way we can to create a better experience for the talent.

[00:16:39] A.J. Lawrence: With that kind of approach to it, how are you looking? Or are you looking at global X town? Cause I noticed your offices or your nexuses are all pretty much US-based, but with what’s going on globalized talent, it’s no longer just the VA talent level out there. There is some significant talent level.

[00:16:58] Stephanie Nadi Olson: Yeah, there is. I completely agree. So it’s been interesting for us. So I think to your point earlier about how difficult it is to just run payroll, right, running We Are Rosie with 7,000 freelancers with the benefits that we offer, with the weekly pay, with the high touch model, one of the things that I think it’s impossible to appreciate unless you’re sitting inside this organization, is the operational lift required to run this business and scale this business. I didn’t appreciate that at the jump, right? If someone had told me when I started this company, _’Hey Steph, you’re getting into this territory where there are 1800 laws just in the US governing worker classification’_, I wouldn’t have done it. I would have bailed. I’m like, this is insane. How will we ever? So I say this because there are 1800 worker classification laws on the books, in the US and if you violate them, the IRS is the one coming for you, which nobody wants to happen. And they’re different. They’re federal, they’re state, they’re local, and they’re often conflicting and they are constantly changing.

[00:17:54] So just navigating that to be set up to do business with Rosies in all 50 states has been an absolute operational beast and a thousand percent worth it because now we get to have Rosies in all 50 states. But as we look to expand globally, you can imagine that that adds an additional layer of complexity.

[00:18:11] We actually have a waitlist of clients that want global Rosies or talent from We Are Rosie outside of the US. We’re eager to make it happen and we’ll do it as soon as we can do it in a way that ensures we can be compliant with global worker classification laws. And also that the experience of our global Rosies will be on par with what we can offer here in the US.

[00:18:30] A.J. Lawrence: That’s interesting because with your sales background and your obvious knowledge of marketing, was it sort of your own growth in operations? Cause I always joked, as we grew with my, the agency I sold, we got to about 7 million things, got choppy and fell down somewhere around 5 million. I stopped doing anything other than operations.

[00:18:48] It was like get me out, but it sounds like a very well-oiled machine to use that phrase, but it does seem like you’re building a very deliberate structure in your operations. Was it someone, did you bring talent in?

[00:19:01] Stephanie Nadi Olson: Absolutely. So. I got lucky, right? So I think about this line guy, Roz question about it, _’Was it luck or like, did you work really hard?_

[00:19:08] And this instance, I got really lucky. One of my, I think she was my third hire, is an operational genius. She’s actually a fantastic example of nontraditional talent. She doesn’t have an operations background. She has a marketing background, but she was an early employee and we’re all hands on deck, everybody’s taking the trash out and she leaned in and she has absolutely rocked it for us. I mean, without her, I don’t know. We would not be where we are today. The other thing, and I’m really thankful for this is, I’m not afraid of operations. So I went to an engineering school to be an engineer. I spent my first two years of undergrad, I was going to be a biomedical engineer. So I love data. I’m not afraid of spreadsheets. I love systems thinking. I love thinking about the interconnectedness of things. And so I actually think that background has come in really handy as we think about all of the data we have on 7,500 Rosies and how to ensure that we’re operating, running a business smoothly in support of them.

[00:20:03] So I think that that experience has really come in handy, but honestly, it’s just been this team and we just hired our first ever COO. And then she’s been here for about two months and she has just been rocking it for us too.

[00:20:14] A.J. Lawrence: Congratulations. Yeah. It is fun because that’s a big transition now. Was it sort of just from the size of the business or was it from a revenue point? Was it planned to kind of do that? Cause that’s a big transition point that I think as someone who failed at that transition.

[00:20:30] Stephanie Nadi Olson: It happened really quickly for us. So this business did over a million dollars in our first nine months. And at that time it was me and my nanny, who I had completely bamboozled into starting a company with me. And we knew that we were onto something, right? For her to be working part time and just, I mean she – another angel, right? She still works here. She’s absolutely incredible at just about anything you put in front of her. And for the two of us to kind of like, get this thing off the ground with that speed, I knew we were onto something and I never wanted this to be a small business, A.J.. When I quit my job and when I found the idea after having all those conversations with all those brilliant people, many of them in marketing who had gone independent, I sat down with my husband and said, _’__Honey, I don’t half ass anything.__ I am swinging for the fences. This is not a lifestyle business. This is a business that is going to transform the way work happens in marketing, and it’s going to be tough.’_

[00:21:24] And so that was the mindset, right? The mindset was always massive scale. Like how many lives can we touch? How many people can we put to work? How can we normalize this way of working? And so we were constantly placing bets ahead of ourselves and making, you know, what some people would consider like risky bets, but I always, I’ll always bet on this team and we even did it during COVID. But when COVID first started, we- it started March and April, May those are the three months that I probably slept like 10 hours in total. We lost 80% of our business overnight and it was scary. Cause we had just made a new round of hires, but we run a really financially sound business and we made a bet. So I got together with my leadership team and I said, however this shakes out ,our business is going to be more needed than ever and I’m willing to bet on this team. And so we used those three months where it was very quiet, crickets for awhile to work on our strategy, work on our operational goals, and we doubled the size of our team. So we went into the coffers and we bet on some new hires. And by the end of 2020, we had more than doubled the size of our business even with that three months slump.

[00:22:32] A.J. Lawrence: That must’ve been insane for you.

[00:22:35] Stephanie Nadi Olson: Yeah. I think, I think last year took probably like 10 years off my life. I’m going to have to do like all sorts of therapy to try and get some of that time back because it was rough.

[00:22:45] A.J. Lawrence: In looking at that type of transition. That is a very, very difficult mindset change. Was that the most difficult you’ve had with Rosie or has there been other things? What were some of the biggest challenges deciding where to go?

[00:22:59] Stephanie Nadi Olson: Yeah, the bigger you get, for me at least, the bigger this company gets, the more I find fear playing a role in some of my decision-making. And what I mean by that is when I started this company, I was so happy to not be working for people I didn’t respect anymore. I’d had like a pretty rough experience. I was like, I’m only going to do the right thing. And the right thing is always so easy to know because there’s four people that work here.

[00:23:26] And so it was very clear, like, how do we take the best care of this team? How do we make sure we’re an inspiring place to work and people can share ideas. We’re now more than 40 people and you can’t make everybody happy all the time and you can’t have this free love kind of environment. That was really how we got this thing off the ground.

[00:23:46] And so that has been a challenge, right? In trying to figure out how, even if people don’t all agree that everybody in the organization feels heard and that we don’t create an environment where people don’t feel heard because that will stifle our own innovation and creativity as a company. And so that’s been a big transition because it’s happened so fast.

[00:24:05] It was less than 18 months ago that we were under five people or under eight people maybe. And now we’ve got maybe 45. So it’s happened so quickly and making sure we’re keeping up with everything from a cultural standpoint and from a process standpoint and all of a sudden like damn, we need to write this down.

[00:24:22] We’re onboarding new hires in groups now. It’s not like one every year like it used to be. So I think those kinds of scale challenges have been really interesting. And I think our growth has been the growth of a venture-backed startup without venture. And there’s no playbook for that. That’s the tough thing, right?

[00:24:39] Like I don’t have a blueprint for, okay when you raise your Series A, this is what you do when you raise your Series B, this is what you do. We are paving our own way. And there aren’t a ton of businesses that I can look to that have done this and that have grown in this way.

[00:24:54] A.J. Lawrence: I kind of think back on things like Design Pickle, which now is doing about 12 million annual, and that was all bootstrapped. But they’re are different model, but close. Then you have some of the SAAS’s, some of the micro, the little personal bootstraps not as big. From a talent organization to do that with the moving parts, it’s like you’ve decided that you’re going for the high degree of complexity. You’ve decided, all right, I’m going to be scored. I want to be scored on a curve because all the difficulty of just growing a business and I’ve had it.

[00:25:25] Stephanie Nadi Olson: Yes, and COVID right. It’s a wild time. Yeah, no, I totally agree. We are, we are doing the most over here.

[00:25:32] A.J. Lawrence: It is. Yeah. Cause like I got to about 35 people and I couldn’t keep in touch with everyone on regular basis anymore. And I had so build my management style around that, that it took a falling back down to, you know, it was like, all right, I need a different type of business model. So I love that you would have that structuring. You’re able to take that consideration and I think a lot of people in the audience, I know are hitting these different inflection points in seeing internal talent, when you bring in talent to kind of help you and how you think about it. For marketing space. I remember my experience when I was a kid all the way to like where I see things now and talking it’s completely different. But more importantly, what are you finding what’s really interesting to you that you are excited to incorporate into We Are Rosie? What’s out there right now that you really are excited about?

[00:26:25] Stephanie Nadi Olson: Yeah. I think like additional ways to care for talent. And this notion that when we talk about the future of work, if we’re not talking about freedom of choice, then we’re not thinking about it right. So I want to continue challenging us to consider how are the ways that we can support talent, really to get people out of full-time jobs that they hate where they’re miserable and to have a fulfilling life and career because I don’t think we fully can appreciate how much having so many people who are working jobs every day, that like, do not resonate with them and do not even make sense for the life that they have, right? That are just like swimming upstream every single day when you go to work and the idea that using technology, we can allow these people to engage in the workforce in a way that is really meaningful for corporations and people that need talent but also for those people to have a more fulfilled life.

[00:27:20] I mean, we’re getting closer to the actualization of talent, right? In many ways we aren’t, if you look at like Maslow’s hierarchy of needs, people don’t even have security. Like we’re not even at the bottom, we’re not even doing well. And we’ve tricked people into thinking that they have it, working these full-time permanent jobs where they can be let go at any moment. But how do we allow people to really do work that they care about? And how do we give them the freedom of choice to opt in to work that lights them up every day. And then what is the, what is the ripple effect of that? How does that impact their family, their community, their friends and the world at large, when we start aligning people better to work that will allow them to be a fuller version of themselves.

[00:28:00] A.J. Lawrence: I always like to say, it’s like this infrastructure, the difficulty of providing an infrastructure so someone can just do the things they like. That becomes so much of this overhead craziness. I am happy American, but living abroad and the times I studied abroad when I was younger, I have to say public health systems are just the most amazing things ever.

[00:28:23] Folks, the doctors usually get paid more than the doctors in the US and they pay 80% less in bureaucracy to their medical costs, but pay socialism.

[00:28:35] Stephanie Nadi Olson: I totally agree. Oh my God. If we were able to have the backing of public health and not have to provide it on our own, our Rosies would be better for it. The quality of care would be better. I’m a fan for sure.

[00:28:48] A.J. Lawrence: Having worked with and known people in some large agencies over the years. I know people who are still there who would love to leave in a heartbeat, but it’s the insurance that is such a major thing. That’s really cool. I like that you’re diving deeper and looking at that.

[00:29:05] One of the things I found so cool, as I had mentioned earlier, I started my last agency because my wife was pregnant with our second child. She was working at a big consulting firm and I was rising up through an agency and like, okay, I’m on a plane 24/7, barely seeing my little boy all the time. Now, we have a daughter at one, something that I can control more of that.But I think you took it even further. Can you tell us a little bit about why you name your firm We Are Rosie?

[00:29:34] Stephanie Nadi Olson: We talked about it a little bit when I had that sit down conversation with my husband and said, I am swinging for the fences. This is, I’m not going to have any regrets after I try to start this company. And I knew how hard it was because I had worked at startups and I knew that it would be even harder because I’m a female founder and because I’m a mother. And I wanted the company to have a name that would always remind me of why I’m doing this so that when times get really hard, I kind of have that like always in my face reminder of this is why this work is important. And I named the company after my younger daughter, Margo Rosie, because I wanted to remember if we do our job right at We Are Rosie, both of my daughters and your children and their children are going to be higher up on that Maslow’s hierarchy of needs, right? They will be able to have a higher propensity of being able to do work that lights them up, that is aligned with who they are, that gives them the flexibility to be a human, that doesn’t necessarily want or subscribe to a hierarchal career path, but to really just get to explore life and explore a career that is more aligned with who you are at the different seasons and phases of your life.

[00:30:41] A.J. Lawrence: I love that. I had a conversation with a corporate advisor who works with firms more of the 10 to sort of 50 million range and we were talking about some goals setting things that, you know, I’ve struggled with in the past. And I know some of our listeners have discussed when I’ve talked with them and he said, you’ve taken it a step further. He says, choose one of your children or someone important to them and pick a day either right after, or right before their birthday to kind of set up where are we doing as it aligns with what I’m hoping to do for this person?

[00:31:12] Not that you’re running the company for them but just to do it and I love you’re taking it even further. And every day you say your daughter’s name, which is so cool.

[00:31:23] Stephanie Nadi Olson: She’s five now. So she was two when we got this thing going, I think she’s into it. I think she’s the most into it now because she’s realized it bothers her sister.

[00:31:37] That is a conversation we have had at the dinner table. I didn’t think about it. Like I’ll say in my defense, the reason I named the company after my younger daughter and not my older daughter, Ingrid is I had had a rough experience where my manager told me that I wasn’t allowed to go to leadership meetings until I stopped breastfeeding my youngest daughter and I was so pissed. Like I was so, like, it was just one of those jaw on the floor moments. And I was just like, never again, like now I am going to go do my own thing and build a life where I don’t have to deal with stuff like that. And so that was really why I honed in on her as I thought about she better not ever have to deal with that. And if she does, she better have options to just say I’m out, right? It goes back to that freedom of choice.

[00:32:24] A.J. Lawrence: You’re building this company. How do you think of the legacy you’re creating? I know legacy is a kind of a loaded term for me. It’s one I’m able to do for my children, not to give them a life, but to give them the tools and capabilities and hopefully the enthusiasm to create the life they want.

[00:32:41] How do you think of this legacy you’re building with We Are Rosie and your journey as an entrepreneur?

[00:32:48] Stephanie Nadi Olson: Yeah, it’s a big question. I don’t think about it often, to be honest. For me, it’s just kind of one foot in front of the other. What’s the next right thing or closest to right thing I can do today. But really for me, as I kind of reflect on it now, the generational difference between the lived experience of my parents and me is so, so stark, right? So neither of my parents went to college. My father spent his childhood in refugee camps in Palestine. My grandfather was a wealthy farmer and had his farm taken away from him and was put in jail and then a refugee camp. And so when I think about just how much things have changed, right, with me, my brother and my sister being first gen American first gen college grads, and the incredible opportunity we have, I don’t want to squander that, right? And so when I think about the work that I’m doing every day, I think I have an obligation to make the most of my privilege because my ancestors and my parents sacrificed so much for me to have that opportunity.

[00:33:46] I want to create more opportunity for my kids. And I hope to instill that sense of responsibility in my daughters too, through the example I’m setting that we have to use our privilege to make the world a better place for other people who may not have as much privilege or opportunity as we do.

[00:34:02] A.J. Lawrence: What are some of the things you look at for giving back? Obviously We Are Rosie and giving back to talent, but what else is important to you?

[00:34:10] Stephanie Nadi Olson: Yeah, it’s really important for me to take care of my family and I want my parents to be amazing, like they deserve everything. I admire them so much and I want to make sure that I’m taking care of them. I’d like to go back and support some of my family members in Palestine and Jordan who have had a really rough existence. And I want to be able to support causes that are important to me and my husband and my family, and have the freedom both intellectually and financially to be able to do these things because this is something that my ancestors couldn’t have imagined. And for me, the most tangible expression of my success as an entrepreneur is the children that I’m raising in the midst of this and how they’re going to look back. When I was younger, I didn’t go to summer camp. I would go work with my mom in the summer. And part of it was financial constraints. And part of it was, I loved working and I loved creating things and learning new things. And I was just super curious and I hope to instill that, that kind of sense of wonder in my daughters so that they can go explore the world and really figure out what lights them up and do more of that.

[00:35:18] A.J. Lawrence: I can’t wait to see that. So what do you see next for Rosie? And then for you on your journey as an entrepreneur?

[00:35:26] Stephanie Nadi Olson: We are going to continue growing and my goal is for We Are Rosie to be the defacto source for flexible talent in the marketing industry and to support CMOs and all of their agencies in becoming more agile and inclusive.

[00:35:39] So we’re on track for pretty rapid scale this year. We will probably three and a half X after two and a half X-ing last year. So we’re trying to keep our head down and hold on to our horses at the moment. But you know, longer term kind of picking my head up, we absolutely will expand globally soon, right? And we’re, it’s just constantly, we’re constantly in triaged mode in terms of our priorities and taking really good care of our customers that we have now and our Rosies. And so we’ll continue to do that. Longer term, I’m certainly looking at other verticals that need this level of disruption. I think actually all of corporate America needs this level of disruption so the field’s kind of wide open. If we want to take everything that we’ve learned in the marketing industry and apply it elsewhere, but I’m just really excited to be able to continue doing this work.

[00:36:25] And for me as an entrepreneur, this business is my heart and soul. I tell people, this is exactly where I meant to be at this moment in my life, I have no doubt about it. I don’t have a wandering eye. I don’t have another idea. I don’t have the next We Are Rosie idea, but I know that I will, like I feel it in my bones. I know that when the time is right, I’ll have that, that next idea. And I will be inspired to do this crazy thing again because it is a journey for crazy people, for sure.

[00:36:56] A.J. Lawrence: Yeah. No, I definitely agree. It’s sort of like having done a few agencies and been like, ah, and now all of a sudden it’s like, okay, I took a summer retirement now play. I hope it’s in good time because it sounds like you’re having a lot of fun with We Are Rosie, but down the road, it’ll be very, very cool to see what the next and maybe it’s We Are Ingrid.

[00:37:17] Stephanie Nadi Olson: It will, I think it will have to be A.J..

[00:37:19] A.J. Lawrence: I know. There will be some serious issues.

[00:37:24] Stephanie Nadi Olson: We’re building our tech right now. I was trying to convince my team to call it Ingrid.

[00:37:29] A.J. Lawrence: Oops. Sorry. Well, thank you so much for coming on the show. I can’t wait to see what you guys do. I mean, this has been great. I think the audience learned a lot from having you on. I noticed that you do look for talent. Should people go check out the site?

[00:37:45] Stephanie Nadi Olson: Yeah, please join us. If you are an independent marketer or would like to become an independent marketer, we call it freelance curious over here, you can join We Are Rosie by going to our website, wearerosie.com. You can join our community wearerosie.com/join, and you can follow us on all the social channels. We’re everywhere and then my personal favorite social handle is my Twitter. I’m @StephanieNOlson.

[00:38:10] A.J. Lawrence: Well, thank you so much, Steph. I can’t wait to have you back on. This has been great. Thank you.

[00:38:16] Stephanie Nadi Olson: I’m so happy to have been here. Thank you for having me.

[00:38:18] A.J. Lawrence: Wow. That was a lot, lot of fun for me to talk with Steph about what she is doing with We Are Rosie. I am incredibly impressed. If I can speak, she’s building an amazing company and I think as entrepreneurs when we listened to her and we listened to where she came from and what she’s trying to do and where she’s going with the company, there’s so much we can learn. I think definitely in looking at how she used beginner eyes. She wasn’t really a marketing person, but she’d been around it. She had this great background in sales. She understood media. She knew the space and she dove in and kind of brought in this need to find answers for businesses’ problems, but without the jaundiced view of this is how it’s done. And I think so often I know I’m like, well, I’ve done it a gazillion times, let’s just do this.

[00:39:12] When maybe that practicing new eyes, beginner eyes, that’s something we can all use as entrepreneurs. Two, is this, yes, it was COVID but her, if you listen to the way she’s talking about how she’s built the company and where she’s going, there’s a high degree of complexity that is occurring in this business fraction, not the complexity that she’s did. I literally had a break, not break down, but very, very close. She has built it. And the way that is very interesting is early on she used her existing talent and gave him an opportunity to grow. That is something that is very difficult. I know for many entrepreneurs, it is a little bit of luck, but it is also this idea of creating the right environment for your talent, for your team to grow.

[00:40:02] Yes, you won’t be able to say, if I create this open environment, then Y will occur. But the nice thing is by putting the time, putting effort building this inclusive environment, that she really put from beginning into everything, she created this foundation that allowed these great things to occur.

[00:40:21] So that took her so far. But then in using the situation around COVID to reevaluate what was going on in the business, I don’t think many of us take that deep dive enough into our business. Yes, we talk about planning, we do all sorts of things, wherever we want to go, but in really reevaluating what’s going on and especially in the face of something like COVID where she was losing so much of her business and deciding that core concept of where she wanted to go was true and worth reinvesting into, to doubling down into, is really impressive because she used that situation to increase her talent pool. She was talking about her new COO, other people, other talent that’s coming on.

[00:41:03] Those are things that I found difficult to the entrepreneur. And speaking with other entrepreneurs, they found difficult of like, _yeah, yeah, we can kind of get by_. She decided not to get by. She decided to overemphasize their talent level to then rocket ship on a bootstrap, which is different mindset. You’ll always see all the stuff from the VC backs, but she did something based on her belief of her own bootstrapped business that I think more of us should take into consideration and to emphasize.

[00:41:31] I know I’m going to be talking more with my team as we plan for how we’re rolling out our new products and new offerings too. Like, how can we go deeper? How can we more re-invest in ourselves? And then lastly, her legacy, how much it is about her family, her children, what her parents went through to bring her to this opportunity that she’s had and then she’s done so much with and where she’s expecting to go. It’s not something she’s spending a ton of time on, but it is something that I think is another thing that we, as entrepreneurs, can take into consideration and learn from, is this idea of like, _why we do this_? Because for me, I did not have as elegant of a reasoning as Hartsburg, but for me it was my children and the expectation that I want to provide them – for them to create their own lives, not to give it to them, but for them to create their lives. And I know that helped me deal with a lot of the craziness that we all deal with with entrepreneurs. Steph has this amazing background, this dedication and if you listened to like working for mother as a little child, working from 14, all these things she’s built into her structure, her ability to be an entrepreneur.

[00:42:40] It’s built upon all these things together. So it’s like when we look and we think about why we are going to do something, it allows us to have that extra bit of effort, willpower and a little bit more of I don’t care if it’s not going to work, I’m going to make it work. I used to just always make sure that whatever I needed to get done got done.

[00:43:02] She used the phrase, take out the garbage and that was something I used to use early on in my last company. We’ll do anything. We’ll even take out your garbage. So, yes. Think about your legacy. It’s not going to be the end all, but just by really, really framing it well and why it’s important to you to do something. It will give you that little bit of extra energy, that little bit of mindset that helps you when everything gets difficult.

[00:43:26] So again, everyone, thank you so much for listening to another episode. Details about Steph and We Are Rosie and how to join their talent pool, join their community, become a Rosie, will all be below in the show notes.

[00:43:38] And as always go check out our social media. Those links will be below and you’ll get to see me and my collection of Hawaiian shirts and crazy hair. Thank you for listening. I can’t wait to talk to you again. I hope you have a wonderful day. Goodbye.

[00:43:58] This episode of Beyond 8 Figures is over, but your journey as an entrepreneur continues. So if we can help you with anything, please just let us know. And if you liked this episode, please share it with someone who might learn from it. Until next time, keep growing and find the joy in your journey. This is A.J., and I’ll be talking to you soon. Bye bye.

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