camryn pickworth leader assistant podcast

Camryn Pickworth is the founder of The First Pick VA Group, a successful virtual assistant business.

In this episode, Camryn shares her story of launching her virtual assistant business in the middle of a pandemic – and at the age of 21. She also talks about setting boundaries, ethical “freelanceship,” team building, and overcoming childhood trauma and shaping it into a successful future.


You don’t lead by pointing and telling people some place to go. You lead by going to that place and making a case.

—Ken Kesey


At 21 years old (in the height of the covid pandemic) Camryn founded her company, The First Pick VA Group, that within two years has expanded into a six-figure business, signed over 50 clients nationwide, and is ranked among the top 1% of virtual assistants in the country. Camryn created an updated freelancing experience for her clients by granting them access to virtual assistants who receive continual training and mentorship.

Camryn believes in the importance of a stranger’s kindness and strives to bring the values of compassion and support into her leadership style. She puts an emphasis on “ethical freelanceship” – to make the workplace a safe, inclusive, and welcoming team environment for all.

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Camryn Pickworth 0:00
Hi, I’m Camryn Pickworth and my leadership close the day and from Ken Kesey, you don’t leave by pointing and telling people someplace to go you lead by going to that place and making a case.

Podcast Intro 0:17
The Leader Assistant Podcast exists to encourage and challenge assistants to become confident game changing leader assistants.

Jeremy Burrows 0:32
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Camryn Pickworth 1:32
Doing very well. Thank you excited to be here.

Jeremy Burrows 1:35
Yeah. What part of the world are you in?

Camryn Pickworth 1:37
I’m in Salem, Oregon. Just a little bit south of Portland.

Jeremy Burrows 1:42
Very nice. And are you from that area?

Camryn Pickworth 1:44
No. I’m actually from the Midwest, the Columbus Ohio area.

Jeremy Burrows 1:48
Ah, lovely. That’s where my wife is from? Callbacks. I was gonna say her dad is in the Ohio State Hall of Fame. He was a hockey player, hockey coach. And yeah, so I can do a couple tailgating gatherings at The Ohio State University. So spent a little bit of time in Columbus before they retired and moved away. But what she went to I think it was Pickerington High School. Yeah, I

Camryn Pickworth 2:20
had a lot of friends from the Pickerington area. Oh, nice, small world.

Jeremy Burrows 2:23
So how did you end up in the on the West Coast then?

Camryn Pickworth 2:29
Yeah, so I, my sister moved out here to go to naturopathic school. So that’s like natural medicine person. And I really fell in love with the area. And so I decided to make the trek out here for college.

Jeremy Burrows 2:41
Cool. And how did you end up in the assistant world?

Camryn Pickworth 2:47
Yeah. So around my freshman year of college, I went to Willamette University, I was looking for a way to make money as most college kids are. I’ve worked in the restaurant world since I was about 13 really young. And I just knew that I didn’t want to keep doing that. So I was looking for alternative options. And I kind of stumbled upon the virtual assistant world. And I really fell in love with it. I fell in love with working with clients, I fell in love with maintaining efficiencies and systems. And so over the course of my college career, I just kind of continued to pick up on it. And in combination with my communications degree as I got into my senior year of college, and I was really starting to have to make that decision about what did I really want to do with my future? I kind of had to choose between was I going to go into corporate communications and go that route? Or did I want to try to start something on my own and go go that route? So I did open up my own business, my senior year of college, and I just continued on with that. And we’ve been able to grow ever since.

Jeremy Burrows 3:46
Wow, that’s amazing. So you said we How many people did you start with? Was it just you at the beginning? And how many people are on your team now?

Camryn Pickworth 3:55
Yeah, so I was mostly me to start, I worked with my clients on my own for probably about two or three years. And then I did start bringing in other team members. So that’s why we’re an agency. Now I have a small team still have seven who I personally train and mentor throughout their virtual assistant journey. Some people come to me a little bit more experts, some people are pretty new. So it’s a good mix. And then I also say we because my partner was very involved and encouraging and helping me kind of get to where I am. So he was a big part of helping with that as well.

Jeremy Burrows 4:27
Very nice. And how did you get, you know, when we talk about virtual assistants and when I talk to full time executive assistants like myself who you know, their day in and day out full time, quote unquote, normal assistant job, and they think you know what, I kind of want to work from home flexibility. I kind of want to start my own thing. But I don’t know where to get clients. How did you how did you start off getting clients?

Camryn Pickworth 4:59
Yeah, so I Started on the major platforms. So Fiverr Upwork, those types of places. And I really did start by building up a strong profile I really committed early on to doing and being kind of an excellent worker for my, for my clients. So I, I was able to work up in about two years to getting over 55 star reviews on up work. And I think that really, really helped kind of jumpstart that. And through all those clients, I now work almost completely referral base. So I don’t have to continue to maintain too much of a present presence on those platforms, I can really just continually get clients from the amazing clients that I’ve already built.

Jeremy Burrows 5:39
That’s great. And then how did you find other assistants to help with as you get more clients?

Camryn Pickworth 5:46
Yeah, so I have a pretty, pretty vigorous process, I, you know, I really want to provide excellent service to my clients and their associated people. So I go through a whole system, I find them traditionally. So whether that’s like, indeed, places like that, like traditional recruiting sites, I do it all myself, I vet them all. I have interviews with them, I test them on their skills. And then once I’ve kind of decided that somebody is at least in a great place to be molded, like, I don’t need anybody to be perfect when they come to me, none of us are perfect. So that’s not what I’m looking for. But I am looking for people who are moldable, and going to be at least invested in trying to provide good service. So I go through that. And then we start the training process from there.

Jeremy Burrows 6:32
Wow. So are you hiring on a regular basis? Do you kind of go into in seasons?

Camryn Pickworth 6:41
Yeah, we do go in season. So one thing that’s really important to me at my agency, and this is a little bit different across different verticals as agencies is that we don’t have any sort of competition as part of our structure. So I never want my assistants to feel like they’re competing with other members of our team for clients. So I’m pretty choosy about when and how I hire so that the team really fits together, and we have a really diverse set of skills. So then nobody has to feel like they’re competing too much for clients.

Jeremy Burrows 7:10
Okay, awesome. And then how does your model work? Is it are your assistants contractor, part time? Are they full time with benefits and everything? How does that work? I know different VA firms I’ve talked to do it differently.

Camryn Pickworth 7:26
Yeah, right now we’re all contractors. I am hoping to start being able to offer full time benefits, all that type of stuff soon. But we are just at the beginning of our third full year. So we’re still looking to grow a lot in the next couple of years.

Jeremy Burrows 7:41
Okay, cool. And then I see on your website, which is first pick P IC K I see some of the clients you’ve worked with pretty impressive. Sounds like you’ve had some good success. What would you have any fun stories of maybe you or your team? Providing a little bit of a miracle? Working magic working, whatever you want to call it superhero work for one of your clients? And in a tough situation?

Camryn Pickworth 8:17
Oh, gosh, that’s so such a good question. I work with so many amazing clients that that we do, we juggle so much for all of them. One thing that comes to mind initially was I was working with one of my clients, and I did I was doing mostly their kind of billing and invoicing type stuff. And they had this one particular client who just could not pay their invoices on time, and they were a big client. So we’re talking about, you know, 50 plus $1,000 per invoice, and they just would not pay these invoices on time. And they kept backing up and they kept backing up. And at one point, my client came to me and they said, Cameron, you know, can you just get them to pay these, like, we’ll do anything if you can just get these people to pay these invoices. And so it took quite a while and I had to talk to probably 30 people in that company to get these invoices paid. But finally after think 10 months of them not paying these consistently, really large invoices. We got them to pay them all at once. And it was just completely off the plate for my client. And that was such a win across the board. Because so many people had been trying to get those invoices paid. And it took quite a while. So that was definitely one that had a real tangible effect for the company.

Jeremy Burrows 9:29
Wow. Yes, that’s literally affecting the bottom line.

Camryn Pickworth 9:33
Yes. Very much affecting the bottom line.

Jeremy Burrows 9:36
Nice. So what about a couple a couple topics that you brought up as we were chatting about being on the show and topics you’d be interested in? You’re you started pretty young. You started this business pretty young. I believe you were 21 when he started is that right?

Camryn Pickworth 9:57
Yeah, that’s when I officially launched the So I’ve been doing virtual assistant work since I was 18. But I officially started the business at 21.

Jeremy Burrows 10:06
Okay, and so that was during COVID. Was that right? Yep. Wow. And so you’re a young entrepreneur? What? What’s something that you would say to those listening who are either young, just speak to the young entrepreneur, world, but or just simply people who don’t see themselves running their own business? Or maybe they’ve thought about it, but they just can’t quite get over that hump of, of taking a risk and trying it out? What are your thoughts on just from your young entrepreneur? Experience?

Camryn Pickworth 10:48
Yeah, one thing I like to say to young people and young people that I talk to you, especially people from my schools that I’ve gone to, that I don’t feel like entrepreneurship is an option that is talked about for young people, when we talk about entrepreneurship, we’re talking about people primarily in their 30s 40s 50s, people who have had a career and now don’t want to have a career. And this is something I feel very passionate about as somebody who’s actually the very top of the the Gen Z group. And for all Gen Z’s that are going to come after me, I think that we’re looking for a different type of work. And I think that entrepreneurship gives people that option to not have to go corporate not have to go into these traditional career paths, where they can actually really build something that’s unique to them in the life that they want. And I don’t think that you have to wait till you’re in your 30s 40s 50s, I think you can just say, Hey, I have a passion for this, I have a skill for this. I’ve built a little bit of you know, knowledge around how to be the best I can at this thing. And so I’m going to go off on my own and see what I can make of it. And if I fail, I fail. And that’s part of entrepreneurship and part of life. So don’t be afraid of that failure. Because in the long run, it’s really going to help you succeed with your goals.

Jeremy Burrows 12:03
Well said, was there speaking of failure, was there a moment when you’re like, Oh, this is not going to work? I’m coming up against an obstacle that I don’t know if I can overcome.

Camryn Pickworth 12:15
Yes, definitely. I think at multiple points I’ve, I’ve always been more entrepreneurial, I had entrepreneur parents, I have eight aunts and uncles, and six of them are entrepreneurs. So it a little bit runs in my in my gene pool. But I would say that as I was getting older, like late high school, early college, I tried a lot of different things. So like I wanted to go into psychology, that’s what I thought I was going to go into school for. And I wanted to start a interior design business, I wanted to go into real estate at one point. And I tried all these little different things, to see what really clicked and it wasn’t until I landed on virtual assistant work that it really felt like it clicked for me. In addition to that, when I as I’ve been working as a virtual assistant, and working as an EA, virtually for lots of clients, there were a lot of times where you get really bad impostor syndrome, especially if you are working with so high tier clients, because I was 21 working with, you know, multimillion dollar CEOs and thinking to myself, like, I don’t know if I belong in this room with these people. And then, and then reminding yourself that they wouldn’t have you in the room if they didn’t want you there. So that’s, I think, a really important reminder for young people that you that imposter syndrome is going to happen. And there are going to be moments where you try things and they’re not the thing that’s for you. And that’s okay. Just keep keep on keeping on. And try your best. And at some point, you will find something that that really clicks.

Jeremy Burrows 13:43
Yeah. So what about balance, work life balance, as you know, you’re doing freelance work. I know, from experience in my career, if you have multiple executives you’re supporting as a virtual assistant. You know, it’s there’s like that perception of this glamorous life or I’m just sitting on the beach getting my work done. But then the reality is like, oh, you know, instead of just having one boss that I answer to, I had, like, multiple bosses, all hours of the day, bugging me. So how do you keep keep balanced and create the lifestyle you want?

Camryn Pickworth 14:21
Absolutely. Great question. I think that it takes practice I do. I don’t think that I’m into it and be great at setting boundaries. And I really think that’s such a big part of whether you’re any virtual assistant working with multiple clients or you’re an in person or full time EA who’s working with one client setting boundaries in this type of profession is so important. And I really struggled with that as somebody who was young and in college and not super, I didn’t have as many responsibilities. Then as I did. Now. I was very giving with my time, and I wouldn’t do things like work with clients super late into the night even though I didn’t really want to do I’m tired, I had a test the next day or things like that. And it as I got older and more responsibilities got put on my plate, both in my personal life and as a business owner, I really had to, I was kind of forced to learn how to set those healthy boundaries, which, for me looks like shutting off around 5pm, I really try very hard not to be on call after five. Especially because as a business owner, I have to do that portion of things as well, and what would traditionally be my free time. And I love to hike, and I love to do things on the weekends like that. And that time is for me, and it’s for my family. And, and that’s really important time. And I cannot be the best assistant, I cannot be the best part of someone’s team if I don’t have that time for myself.

Jeremy Burrows 15:44
So how do you help your team do the same?

Camryn Pickworth 15:48
Absolutely, we spend a lot of time talking about boundaries, we have a whole section of our training about it. And it’s something that I’ve talked about routinely, with my with my team is just how important it is not just for you, but for the relationship that you have with your client to maintain healthy boundaries. If you’re burnt out, if you’re tired, if you’re not focused on the work, because you’ve been overextending yourself, then you’re not going to be able to serve them as best as possible. So it really is beneficial not just to the individual, but also to the client themselves. And that’s something that I remind clients of also that boundaries are not there to, to indicate that somebody doesn’t want to work hard. Just because you want to have time with your family at the end of the night does not mean you’re you’re not a hard worker. And I think that’s a really important thing for clients to also know as they’re getting started with somebody.

Jeremy Burrows 16:40
Yeah. So how, keep on the subject of team building? Yeah. How else have you worked with, you know, remote culture, team building culture, for your team? As you scale? And I know, it’s often a referral based industry, the VA world so you, you definitely want happy clients, happy team members. So those referrals can keep coming in. But yeah, what what’s, uh, some good remote work team building tips?

Camryn Pickworth 17:15
Absolutely. I think that one of the most important things when you’re working with a team, especially, especially a virtual team, is as as my I call myself a team lead. I don’t like the term manager, things like that, because we’re just not a traditional team by any means. I think one thing that I find that super valuable for my team is just being available for them. You know, they know I have clients that I work with, they know that I’m essentially running on my own, and they, they are still a priority for me, and they can reach out to me anytime any day. If they have a question about something if they’d have a concern about a client, if they just aren’t quite sure how to handle a situation I’m I’m there for them, and the rest of the team is there for them. And I think that’s a really important piece of it is we’re not a traditional office, we’re not a traditional group of people that come together every day and work the same hours and are available at the same times, we’re just kind of a core group of people who do a similar thing to the point of being able to have relatable experiences that that really impact our our ability to do good work. So we because we can be a strong team because we can be together because we can bounce ideas off each other and get advice. We’re better workers for our clients. And I think that that’s really important for our team that it’s it’s not about physically working the same hours or being physically together. It’s about this sort of mental agreement that we’re all there for each other, and kind of common common camaraderie together.

Jeremy Burrows 18:53
Love it. Love it. What you mentioned one of the topics ethical freelance ship, which I think you’ve made up the word potentially, which is awesome. I like making up words as well. What do you mean by ethical being ethical freelancer?

Camryn Pickworth 19:08
So I call this term ethical freelance ship. I have noticed a trend and I’ve seen this both in my team and kind of across the virtual assistant world specifically is, as this younger newer generation is coming up, they are looking for those unique opportunities to work independently and not feel like they’re being pushed into some sort of corporate or traditional job. And that is really materializing in that so many young people are going into freelance work and they’re learning skills just like 5060 years ago, somebody would have become a technical work or they would have become like a plumber or something like that. A lot of those people are now getting college educations. And they’re they’re realizing that even though they have this college education, they don’t want to go into a traditional career path. So freelance work where they can learn a technical skill but also kind of manage their themselves in their own business is really beneficial for people. And as that is happening, I think that we need to be conscious as a society that we cannot treat freelancers how we have in the past, which is traditionally very kind of short and and like they’re not a part of a team, like they don’t matter because they’re freelancers. And I’ve experienced that. And almost every Freelancer that I’ve ever experienced, has experienced that negative interaction with a client where you just don’t feel like they respect you, because you’re not a full time member of their staff, even though they really do value and need your work. And so one initiative that I really valued when I practice this, in my business with my team, is the idea of ethical freelance ship where we both demand and give respect as if we were full, full team members, we don’t expect to be treated even though we’re part time members of a team, we we want to treat our clients like they’re our full responsibility, like they’re our full time when we’re with them, and we expect them to treat us the same.

Jeremy Burrows 21:09
That’s great. Well, Cameron, this has been a lot of good insight. And it sounds like you’ve got a great team and a great business going congrats on your young business career and sounds like you’re having fun. Absolutely. That’s what it’s all about. So what what do you kind of the there’s two more topics that I wanted to touch on? One of them is if if there are assistants listening, and I even had an assistant reach out to me earlier today, that just said, Hey, I’m looking for a 20 to 30 hour a week virtual assistant role if you know of anything, what what do you recommend for those assistants? In that situation? They’re like, I just want to 2030 35 hour week remote assistant job, where should they start?

Camryn Pickworth 22:07
Yeah, so I think that they have two primary options. If they feel comfortable getting started on their own, getting onto a freelance platform, and kind of being their own advocate, then I would say get started there. If they want a little bit more hands on somebody who’s going to help them find clients who’s going to vet clients, who’s going to make personal connections based off of their experience, then an agency might be better for them. But I will say that I have had a lot of assistants in the past who have a very negative experiences with these huge assistant platforms. So both both the like SAS platforms like Upwork, and things like that have their own challenges, but also bigger agencies. So agencies that have 1000s and 1000s of assistants across the whole world, there isn’t that personalized aspect to it. So if you have the opportunity to chat with a boutique agency, which is more like what we are, that’s going to be the most personalized experience. And I would also say just be open to working with more than one client, if you want to get up to close to a full time schedule. A lot of virtual assistants that I know do work with multiple clients, if they if they’re trying to get up to full time. I think that’s part of the reason people hire virtual versus in person is because they want somebody for part time. But it’s not impossible to find one person that wants your your full attention.

Jeremy Burrows 23:31
Yeah, that’s great. So the other topic that you shared with me, when we scheduled this call, is overcoming childhood trauma and shaping it into a successful future. That’s a kind of a loaded, loaded bullet line. So however you want to talk about that, I’d love to hear what you’re what you’re hoping to share with those listening.

Camryn Pickworth 23:58
Absolutely. Um, so So that tends to be much larger topic. And I could talk about that for a whole individual. You know, that could be a whole podcast discussion. But what I would say for anybody that has had things happen to them in their past, and people have written them off because of it. So for me not to get too personal. But for when I was a younger girl, my father passed away. And there’s a lot of stigmas that come with that. And there’s a lot of the the ideas of how you’re going to turn out when bad things happen to you as a kid. And I think that one option for people who who feel like they aren’t interested in a traditional career path, maybe because they are dealing with some of these things from their childhood is to think about entrepreneurship and to start something on your own and that just because people might tell you when you’re young, that your life is gonna go a certain way that that is your choice how your life goes in the future. So just because you’ve you’ve dealt with things in childhood does not mean that you can’t build the successful future that you want.

Jeremy Burrows 25:05
That’s great. So was there practically things that have helped you, in your story like, therapy or counseling or, you know, was what practically helped you? And if those listening, have experienced trauma and are trying to move forward, but getting stuck, what do you recommend?

Camryn Pickworth 25:28
I absolutely recommend therapy, I think everybody should do therapy if they’re able to, I think regardless of if you had trauma, or if you’re just a human in this world, there’s there’s no harm and, and getting a little therapy and seeing what comes of it. So I would definitely say that that is really important and can be really life changing, to try to heal and heal with the help of a trained professional. I also think that there’s that it’s worth doing the work. So if you’re hurting if you’re somebody who especially dealt with trauma or loss or anything like that, when you were young, that it is worth trying to heal, because I think that’s something that we convince ourselves really quickly is that we’re just damaged. And because we’re damaged, we can’t move on with our goals, we can’t move on with our life. And I would really suggest that if you’re in your early 20s, and you want to be an entrepreneur and you want to try to go out on your own, you got to heal those wounds too. Because you got to be able to, to work through the issues that you have to be able to put your full self forwards in both a professional relationship just in life in general. So So do the work while you can and and it’s going to be the easiest in your early 20s. So give it a shot.

Jeremy Burrows 26:44
Well said welfare, Karen, thank you so much for being on the show and sharing your story. Where can people find out about you and learn more?

Camryn Pickworth 26:52
Yeah, absolutely. Thank you for having me. First of all, if you’re looking to find us, you can find us all across the board across all social media at First Pick VA. And that’s first like the number pick P IC k and then VA. And you can find us across the board. If you’re looking to chat with us, you can always email us at info at first pick We’re always looking to make new connections. And you can follow me on LinkedIn always looking to connect there as

Jeremy Burrows 27:18
well. Awesome well I’ll put all those links in the show notes at And people can reach out and say hi and learn more about you all and yeah Best of luck to you. Stay in touch and go Columbus Ohio.

Camryn Pickworth 27:38
Thanks Jeremy Go Bucs.

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