Episode 9 - Letting Go To Grow:
An Entrepreneur’s Leadership Evolution

Join Aaron Burnett as he sits down with Kara Roberts, founder of Pepper’s Personal Assistant, to explore what it truly means to design a business that supports your life — not the other way around.

What began as a creative solution during her son’s half-day kindergarten has grown into a 25-person team serving busy executives across Seattle. Along the way, Kara evolved from accidental entrepreneur to confident leader, implementing EOS, building a trusted leadership team, and stepping fully out of the day-to-day.

Today, she runs her company while traveling the world — living proof that entrepreneurship can create both impact and freedom.

This podcast features real entrepreneurs sharing real challenges and solutions. No pitches, no sales - just honest conversations about the moments that shape successful businesses.

Aaron: I am very interested in your story. You used the word nomadic on your website. You had a life of adventure that led you to this business. Tell me that story. 

Kara: Yeah, so actually the Nomad journey is new. I've been traveling full-time for about a year now. My story begins as a stay at home mom and ready to get back in the workforce when both my kids were, in school. And my son ended up getting half day kindergarten, which I thought was the end of the world at the time, but launched where I am today. Because I had to get creative and think about, what I could do in that two and a half hour chunk of time why he was at kindergarten. I just started, doing it myself helping people, everything, that came at me returning shoes to Nordstrom, doing expense reports and things like that. And about two years in is when I decided to start hiring and employees and now. We have a team of, I think around 25 PAs and a great leadership team and management team.

So it's grown a lot over the last 13 years. 

Aaron: So you started your business 13 years ago. Give me a sense of the trajectory of the business. Did, was it a success right out of the gate and you had the. Perfect linear growth, 

Kara: right? Yeah. That nice hockey stick. No, it was a side hustle. The first five years, I was focused more on my boys and raising them and about the five year mark was when I was like, it's time to grow this business and.

Try to make it profitable and not, just some spending money on the side. So that was when I really started learning more. I call myself an accidental entrepreneur 'cause I really didn't think it would ever get to where it is today, when I first started it. But luckily there's a lot of people in Seattle that need our help and we were able to grow.

Over the years. So 

Aaron: tell me about that business. First of all, the name of the business, and then tell me about the services you provide and the sorts of people you serve. 

Kara: The business is Pepper's personal assistant. 13 years ago, the iron Man movies were really popular and Pepper Pots is Iron Man's pa.

That's where the name comes from. We do household management. Helping really busy executives, business owners run their household so that they can focus on their career, on their self-care, on their family. And we take care of all the fun stuff behind the scenes in their homes. So 

Aaron: you used the name Pepper from the Ironman movies?

Yeah. That was a one-to-one relationship. That assistant was. With him just about all the time. Is yours a similar model or do you assign a personal assistant to multiple families? How does that work? 

Kara: Most of them are just with one family. That's a big part of our success is that we put a lot of effort into the matching process.

So it's a one-to-one relationship where they can get to know the home really well and. Take that mental load off of the client. So most of our PAs are about 15 hours a week. So it's a great part-time option for people that don't need full-time help in the home. It, we can do a lot in 15 hours. So anywhere from 15 to 30 hours is our typical client.

Aaron: And what typically, if there is a typical, maybe this is a situation where there's no typical, if there is a typical. What typically happens in those 15 to 30 hours? 

Kara: Yeah. I would say our most popular tasks are laundry. People love that we come in, get it started, get it finished, get it hanging up and folded.

It's like they always say it's like a little fairy has come in, magically put everything back. Another one is vendor management, getting the gutters cleaned and the furnace. Serviced and getting all the quotes and, we have , a vendor list that we've been building for 13 years, so it makes it really easy for us to get trusted people in the home.

We have people that do meal prep, a lot of pet care, taking the dog to the groomer and for walks and all those things, that. You have to do, taking the Amazon returns back and going to Costco and all that fun stuff, you know that, that adds up. Sure.

Aaron: And do you have a typical client?

Kara: Yeah. Most of our clients are, C-suite executives. We have a lot of lawyers doctors business owners. 

Aaron: What sort of people. Are the assistance, is there a typical to that? 

Kara: There really isn't. We have a wide range, male, female, young, old. They have to have had some, kind of experience running a home.

But we've found, after 13 years, the biggest thing is that there's a value match their, people that share our core values that really wanna make life easier for people that can figure things out on their own and be independent. We actually just did a survey of our employees recently and the best thing I read was somebody said they feel like they work with peppers, not for peppers.

And that's exactly the kind of culture that we're trying to build of just great people that wanna do great things. 

Aaron: You mentioned the word independence. I can only imagine how critical that is that the assistant doesn't become another person who needs a lot of 

Kara: aggression. Exactly, yeah. Our goal is to take things off their plate, not add to it, and there's a lot of things they can lean on the team, for questions as well, which is really nice.

Aaron: Do these tend to be long-term relationships? Does an assistant work with a client over a number of years? 

Kara: I think our average is about two years, but we still have clients that have been with us, five, seven years. The idea is ongoing support, until life changes to where they don't need it anymore.

Aaron: So there are any number of. Virtual assistant companies that are hitting my inbox every day and all sorts of marketing out there for virtual assistants and other sorts of assistants. What differentiates your company and your service and your assistance from other competitors in the market? 

Kara: Pretty much most of our competitors are virtual, where they're just doing, maybe like birthday party scheduling and doing some shopping and stuff.

We're very much in the home. Pretty much, 95% of the time is spent in the home actually doing the tasks that are needed. So that's one thing that people really love about us. 

Aaron: Are there competitors around, or are you becoming unique because you actually have people who do physical things?

Kara: There's a few people in the space in the Seattle area, but they're just solopreneurs. So we often refer people to them that, may not be a good fit for us and vice versa. So it's a nice little community. We've all gotten to know each other and all wanna help. People, however we can. Yeah.

So yeah, it's an unusual business model. It's not an easy one, so I've seen people come in and out of the space over 13 years trying to be successful and you really have to know what you're doing and do the hard work to get through some of the challenges. So 

Aaron: what makes it so challenging?

Kara: Our PAs are our employees. They're W2 employees, so we're the middle guy, and we're trying to keep the client happy and the employee happy and retain everybody. And over the years, we've made. Mistakes that we've learned from of, making sure people are set up for success and it's very hands-on.

We have a great management team now that is doing a really great job of training and supporting everybody. So we've got it figured out now, which has been really great. 

Aaron: So you are. Traveling. You said you've been traveling for a year now? 

Kara: Yeah, a little over a year. 

Aaron: Where in the world are you today?

Kara: Today I am in Belfast. I'm at a great coworking space right across from City Hall. It's beautiful. So in Northern Ireland. I've been here for about almost two weeks now, and yeah, it's a really beautiful country. I've enjoyed it a lot. 

Aaron: Have you traveled continuously for that year? 

Kara: Yeah, I don't have a home anymore, so I've been doing kind of a combination of.

Airbnbs and house sitting and hotels and staying with friends and family a little bit too. So I've moved out over a year ago, so living out of a suitcase. It's been a lot of fun. 

Aaron: That sounds like an adventure. 

Kara: Yeah, 

Aaron: I did that for just about a year. But much younger in my life. 

Kara: Right. 

Aaron: Yeah. And it was great.

It would be very different to do it now. 

Kara: I know it's way more fun now that I can afford it, not having to eat Ramen every day. 

Aaron: Before we continue, I want to tell you about the community that made this podcast possible. The Seattle chapter of eo, that's Entrepreneurs organization.

It's not networking, it's not selling to each other. It's real entrepreneurs sharing real challenges and solutions. If you have a business that does at least a million a year in 

revenue and you're curious about joining a community that gets what you're going through. Check out EOCF. 

What led you to this decision that, obviously an unconventional, very adventurous decision.

What brought you here and what has the experience been like? 

Kara: That's a long answer, but the short story is that my youngest went off to university last year when I started my journey and I had recently gotten divorced and was like, I don't want another house payment. I have this opportunity now, like I'm completely free.

I've always had an adventurous spirit. I've always loved traveling. My ancestors were big travelers and I think it's just in my blood to, to go explore the world. So I feel really. Fortunate that I'm able to do it, 

Aaron: what are maybe one or two high points and one or two low points of the trip? 

Kara: I've seen so many places.

It's been really amazing. I think my favorite part is I have friends all over the world and. Being able to go visit, my friend in Germany and friends in England, and when I was in Mexico, a friend just happened to be there at the same time. And so we spent the day together and that's been a lot of fun.

Just connecting with new people and then getting to know the culture. I try to stay in a place, for a little longer. I've done a mix of it, but I definitely prefer when I'm somewhere for a while and I like here in Northern Ireland, they say so many funny things and I'm like, that is definitely getting added to my vocabulary now.

Just learning. They're like, oh, I can't be bothered with that. That's one of my favorite now we're, not wanting to do something. So that's been a lot of fun and the world is just such a big, beautiful place and. With amazing people. So I think some of the challenges it is a little hard traveling a lot because, there's some mornings where I wake up and I'm literally not sure where I am, where it's like, what country am I in?

So my sleep, I think, has been disrupted a little bit, moving around so much. Which I really value my sleep, but I'm making it work. 

Aaron: I would assume that a part of this is traveling to places that you've not visited before, 

Kara: right? 

Aaron: What parts of the world. Have surprised you?

Kara: Switzerland was definitely one of my favorites. I hadn't been there before and it was like every train ride I went, there was just incredible scenery. Grocery prices are much different everywhere around the world. Yeah, like that's been pretty fantastic. Portugal in particular, Mexico, it's expensive for them and that's the hard part.

Is you learn to keep your opinions to yourself. 'cause it's all relative, with housing and groceries.

Aaron: In particular, as an American traveling, it's often very good to keep your 

Kara: opinions. Yes. It's so true. 

Aaron: Tell me about your experience with eo. When did you join eo? 

Kara: Yeah, I was thinking back on this and I can't, I feel like I heard about a OA, the accelerator program through.

Maybe somebody that I met at BNIA long time ago. I was in a place where my team was growing. I was having a lot of leadership struggles. Trying to grow into that role was very difficult with very little experience. And the community I was in, most of them were solopreneurs or maybe had a couple of consultants, that they were paying and so they couldn't really relate.

To the problems that I was having. And so yeah, I joined EOA, I ended up being in EOA, I think for four years. 'cause the pandemic happened. I was supposed to graduate. I was on that trajectory and then the pandemic happened, and so I got to stay in all the learning days a little bit longer, which are so great.

Like you learn so much. But after four years I was like, okay, I'm ready for the big kids table when I graduated. To eo. That was a whole new experience as well which was great. But I really feel like EOA was the foundation for me that I needed. One of the things, I think it was around 2018, I learned that less than 2% of women make it to a million dollars in revenue.

Women owned businesses. And it just, it really fueled me to ask, why am I not? Even considering that, right? It just, I was just growing my business slowly and I had to think about why not me? And then had to question like what was my motivation, and doing that. And so it just really helped having peers and understanding why that was important to me in growing my business.

So I think the other really great thing is you learn. That, I had I think three mentors that were EO members and that was so eye-opening because some of them were in business 20 years, had $10 million businesses and they had the exact same problems I did. It kills you, but also you're like.

Oh, you have this light bulb moment of that's what being an entrepreneur is you're solving problems every day, all day, sometimes the same problems, at different levels and so it just really helped me get clarity and understanding of. I was doing and realizing that it really is a journey.

It's not a destination, and it's just so great being an EO and having, people that are going through the same things you are. 

Aaron: It was surprising and reassuring and also just a little bit of a letdown to find out that there are no entrepreneurs and there's no business size where people feel, oh, I got it.

I've got this all figured out. 

Kara: Yeah. 

Aaron: Yeah. 

Kara: It's so true. 

Aaron: Obviously you did scale your business and you now have a very good leadership team. You are in many ways, living the entrepreneurial dream. You're often doing whatever you want to do, and you're traveling the world while you have a successful and well-functioning business at home.

What have you learned through EO that enabled you to do that? 

Kara: Yeah. Definitely don't think I would be here today without eo. I think there's several things that got me here. One was, I remember at the chapter retreat meeting somebody and he was telling me about, I think he had two businesses. He wasn't working in the day to day, and I was like, that's.

Possible. Like it never even entered my mind, it was like, oh, you have your business, you work in it every day until you decide to sell or retire, that was super inspiring. So I should thank him because it definitely planted a seed where I was like. I wanna do that. How do I do that?

So I think that, and then finding out about EOS, the Entrepreneur operating system, I started implementing that almost two years ago now. And that's what's allowed me to have an amazing leadership team and get out of the day to day. When I came to the UK in August, we were like, all right, let's experiment.

Let's see if I can work. Four hours a week. I'm available to them Tuesday, Thursday, five to 7:00 PM my time, nine to 11 and let's see how it goes. And they're doing amazing. Like my director of operations, she runs the business better than I ever did, and I am so grateful for her. It really has been life changing to have that.

Aaron: We also run on EOS at a leadership team level, and that's been a game changer for us. 

Kara: Yeah. Yeah, it's wonderful. Yeah. 

Aaron: You joined EOA, so at that point, the qualification is you must have at least $250,000 a year in revenue but less than a million. And now you're EO qualified, and you have been for several years and you're off traveling the world.

Tell me about your inner monologue when you joined EO. A. And how different it is today. 

Kara: Oh gosh. I'm a completely different person. I remember thinking, oh, this is a really big investment, which now it would be like the easiest check to write, but at the time it was like, can I afford to do this?

Is it gonna really help? And now you know people that I know that. Are in that space. I'm like, join EOA, because it really is so eye-opening. You have the accountability groups and I learned so much in those two. There was somebody in my group who I just was in awe. Of like the audacity that he had to like just go for it.

And he was doing like these amazing, huge things and it just gave me a lot of confidence to be like, oh yeah, you can do this stuff. And now I feel like I'm at a place where, like you said, we never fully figure it out, but I feel really confident in helping other business owners that may be in a space that I used to be in.

One of my favorite things with EO two is. The experience sharing and the role that, like you don't tell people what to do with their business, right? You can share with them of I've experienced that before and here's how I dealt with it. And because, one of the things I think in other groups, it's like you lose your voice, you lose, touch with yourself, your values.

If somebody's constantly you should do this because you're the one who knows your business, your values, are, is it a lifestyle business? You're not necessarily wanting to grow it to, a hundred million dollar company, but you have this wealth of information from other people that are sharing their journey and the highs and lows as well.

I really value that a lot in EO 

Aaron: is the experience of being a woman in EO different than being a man in eo. 

Kara: Yeah, it definitely is. And that's another thing I really love about eo, the Women's Group. I get emotional thinking about them, like it is just such an incredible group of women.

And also there's a lot of allies in eo, when we have the women's events, the men that show up, that value, the perspective of women is always so appreciated. And I went to the women of eo conference in Montreal last June, which was Global Women from all over the world, and it just was incredible, the energy in that room and everybody was just.

Having a great time getting to know each other and sharing their experiences from around the world, and it was really great. I really loved that.

Aaron: What would you like people to know about you? 

Kara: Ooh, that's a really interesting question. I am, I think a very outside of the box person, kind of everything in life. I don't really go with the flow. I love the make your path kind of way. And I think that EO has really helped me with that, of figuring out, oh, I don't have to do A or B, there's 26 letters in the alphabet, which one, do I wanna do?

Yeah, sure. So I would say that sums me up pretty well, that concept.

Aaron: Yeah, I can see that it, it's been very helpful and enlightening to me to be around people who do things in so many unconventional ways. Yeah. It really broadens the world of possibility. 

Kara: Yeah, it does.

One of the other things where I was like, where else would you get this experience if you weren't an EO member? Last spring, there was a design year exit workshop where like the night before it was a panel of four EO members sharing their. Story of how they sold their business and kind of the mistakes they made, the things that went really well, super creative, ways of structuring the sale and the exit.

And I just was like, where else would you get that? It's not something you could watch on YouTube and understand. And it's funny 'cause I was at a place where I was like, oh, I'm thinking about the future, but not. There yet. And I was like, I'm just gonna go to this just to start learning, about everything.

'cause I know nothing you know about selling a business or that sort of thing. And it just opened up this whole new world where, suddenly I was. Like, oh, maybe I do wanna do this, and what would that look like? And I hired, a m and a advisor to help me, look at my business and see what I needed to do to sell it someday.

And she came back with, I could have seven buyers tomorrow with this price. And I was like, what? I was literally, I met her the morning I was flying to London to come here for three months and. I'm on the plane going wait, I could do this. I'm not going to, not to tell the end of the story, but I'm not ready for that yet.

Yeah. And my wealth manager isn't either. He is let's hold on a little bit. But it was exciting, right? To be like, you're so proud of what you've. Built right. We all put so much time and energy and effort into building businesses and to have somebody excited to sell it to other people that may be excited to buy it was pretty amazing.

It was a really great feeling. And had I not gone to the design your exit workshop, that wouldn't have happened, right? Like I would still be sitting on that. So it's pretty cool.

So I'm in the UK for three months and I am trying something new where I applied for a bunch of house sitting jobs through Trusted House sitters website, and I just booked my plans around the jobs that I got. So it's been really interesting 'cause I'm seeing parts that, as people here, like I was in Northern Wales and I went to the pub and this really nice couple were chatting with me and they were so confused.

They're like, why are you holiday? Holidaying here in, this tiny little village, but it's so great 'cause you get to see like real life, you get to meet the locals and I just really enjoy it. To answer your question, I have a week unplanned when I'm done with. This house sitting job and I'm deciding I might just wing it and maybe go to Scotland.

And then my next house sitting job is in Nottingham area in England.

Aaron: And are you a person who chases the sun? Will you head south as winter? 

Kara: I, yes. I'm going to Mexico City for the winter, so I'm very excited for that. I haven't been there before, but yeah, I was in Puerto Vallarta last winter and I felt bad 'cause when I came back to Seattle, everybody was like, oh, the winter was so terrible.

And I was like, sorry, I dunno, 

Aaron: not yours. 

Kara: I was like, I was on the beach swimming every day. But yeah, 

Aaron: I really enjoyed this. Thank you for spending the time. 

Kara: Yeah, it was great chatting with you and I hope you too, people will join EO 'cause it's a really great organization.