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When the pandemic left Caroline Marshall jobless, she was faced with the decision to try and find another job to fund her impending nursery fees, or to create her own business and become her own boss.
She took the plunge and bootstrapped her own virtual assistant company, all while looking after her first child during lockdown and being pregnant with her second.
As soon as Caroline started Upsource, she began putting in processes, so the company could smoothly run without her, as she was due to go on maternity leave within six months of its launch.
Caroline talks about the challenges both before her maternity leave and upon returning, and how she juggles her personal life, finds the perfect clients and recruits the right staff.
Here’s her unfiltered advice below:
- Weighing up looking for another job after redundancy or starting your own business
- The pandemic led to a greater understanding of juggling work and childcare
- You don’t need a lot of money to start up a virtual assistant business
- Putting in the right processes, so your business can run smoothly when you go on maternity leave
- Suffering with PTSD and using your business to regain your identity
- How to manage and balance a 4-day working week
- The biggest challenge is working out who your perfect client is
- Your business reputation changes once you become VAT registered
- What tasks should entrepreneurs and SMEs look at outsourcing?
- Focus on 3 goals for the week to keep yourself realistically disciplined
- Your business is only as good as the people you recruit
- Managing virtual freelancers
- Being a performer vs an entrepreneur—which is scarier?
- The advantages of being surrounded by other entrepreneurs
- How to scale your business but also know if you’re growing too fast
- The future vision for Upsource
- My business doesn’t keep me awake at night—just my kids
Weighing up looking for another job after redundancy or starting your own business
So while we were in the midst of a global pandemic, you were pregnant. What made you start Upsource from your kitchen table in April 2020?
Oh my goodness. I think many reasons.
The short version, if we go back to the start is, I had experienced redundancy before my first child was a year old, and it had been hard going, I felt a little bit lost after that.
I went to go work at a friend’s family business. It was a great place. But obviously during Covid, it was very in person, and it wasn’t what I was used to.
I’d kind of got used to, I’d been working at a virtual assistant agency before, so that was my background. I’d got used to, pre-Covid actually, the virtual life, a certain amount of flexibility doing work when it worked for me and not just when it needs to be done and things.
So I guess redundancy was where it all started and not fitting into the employment world anymore or that’s how it felt. And when I tried it the second time around, I think in person wasn’t right either.
Then, when the world went into lockdown, it was a while till I knew if I was going to be furloughed or not. So I felt, “Right, here we go again,” main carer, no job, which is very important to me.
And I think it’s very important for women to continue their careers if that’s what they want to do and if that’s what they’re passionate about.
So I thought, well, I can either look for another job while I’m pregnant and start making sure I can pay the nursery fees if hopefully the world does open up, or I can try it on my own.
The pandemic led to a greater understanding of juggling work and childcare
And actually figures show that there was a real surge in female entrepreneurship during the pandemic.
I’d love to hear your take on what the advantages and disadvantages were of starting a business during that time.
Yeah, that’s a fantastic question.
I think it’s hard because I think there were some personal advantages. So my husband did work from home, that was great.
So while we were reliant on his income and his very busy job, I communicated what I wanted to do. So every day we did allow me things like, the time to have a bath because I was pregnant and tired or, time to start working on my business.
I can’t lie, I did nothing for maybe two hours per day for about three months. Once I got out the sickness stage, I did creep up more. So that was an advantage for me.
I do think maybe the virtual networking was a real advantage. I don’t know how I would’ve felt about going into town and networking during those first few months. And I managed to do quite a bit online and meet some people, especially in the VA world. So that was a real advantage as well.
I think people started to open up a bit more. Everyone was at home, whether you were employed or running a business, a lot of people were at home with kids. And so there was that real appreciation at the time of the importance of childcare, what people were juggling.
So when you were starting a business and needed to juggle it around childcare and things, people got it during lockdown. I think that was a real advantage.
You don’t need a lot of money to start up a virtual assistant business
And how did you fund the business in those early days to get it off the ground?
It was very bootstrapped.
So fortunately, the virtual assistant world is something you can start on very little money. I invested less than £1,000 on a website. I also asked around, so I got recommendations. A friend of a friend did our branding, a friend of a friend did the website.
I invested obviously some money in the things you need too, which is insurance, ICO registration, the important things. And also some networking groups, which were quite low cost at the time as well.
So actually very little money, and it was more time and also getting into my plans and things, that’s where the investment came.
Putting in the right processes, so your business can run smoothly when you go on maternity leave
And then I know that six months into launching the business, you went on maternity leave and had to hand over all your clients.
How hard was it to step back from that business that you’d built, and what processes did you put in place to make sure that the business could run smoothly without you at the helm?
I think actually looking back on it, I was very fortunate that it was in the plan to take maternity leave, and it meant I could plan from the start.
I think I had two clients to tell I was going on maternity leave, but otherwise I opened up that conversation from the start, thanks to some encouragement from my VA mentor and the mentorship they’re in.
They were like, just tell them from the start, and the clients were really great about me doing that. They came on board.
So I hope that gives some confidence to anyone who is worried about telling clients or taking on new clients about going on maternity leave. I’m very encouraging of starting it and then handing it over. So that’s what I did.
Something that was really important for my business was having a lead. I had a lead VA, who was someone I’d worked with before, so we’d already had that relationship. She was taking on one of my clients, one of my bigger clients, but also was there for the team.
It was a small team of five I handed over to her, but she was there for any questions if the clients needed anything. They knew I was on maternity leave.
So there was also that respect there for the few months I wasn’t around, especially as the clients were communicated to that our baby was in hospital for a while after.
So it was fairly smooth running on that side, but it was stressful. Even now because my job is to match clients and their perfect VA, that’s a lot easier than my clients and handing them over to a VA.
There was a lot of work that went into that, especially with one because they were going through such a business overhaul. So I’d done all of that with them and then needed to hand it over.
So I think a process, the right software, and the right people, and that was three things that were definitely needed to take the leap of maternity leave.
It’s really interesting that because you were pregnant, you built a business that could run without you.
Do you think it would’ve looked quite different had you not been pregnant? Do you think you put certain processes in place right from the start because of that?
Yes, definitely, I agree.
I think I would’ve stayed because I removed myself from doing VA work. I decided to give that a try once returning from maternity leave, but I think I would’ve stayed doing that work for a lot longer, maybe keeping one large client who I really enjoyed working with or even a couple of smaller ones.
I’m quite a stickler for the process, so I think I probably would’ve put them in place, but not quite as quickly as I did. I remember my plan was to probably step away, keeping in mind that things don’t always go to plan, about a month before my due date.
So I was around for a while and had some wiggle room, but between my second and third trimester I got really tired, really fatigued. I’d been working very hard. So I moved that forward. And then it worked out to be about a month.
Suffering with PTSD and using your business to regain your identity
And then when you did return to the business, you had quite a sick baby and I know you suffered from PTSD.
Can you just talk us through that experience and how you coped with that personally and as an entrepreneur?
I think first and foremost was that backup plan. No one ever wants to talk about worst case scenario, but we really did have the worst-case scenario.
And so we had someone my husband could contact, to let them know things weren’t okay, and that was it. Nothing was needed from me, I could step away from the business and that was great.
Then actually having the business was fantastic for me, not in terms of recovery, but an escapism from that trauma. It was very separate my business from what we went through with my child and coming back home during lockdown.
So I think that was the great thing about having a business, was that I had something there, but it wasn’t all in. It’s not returning to a job where you have to agree certain hours, and it’s kind of all or nothing. It was there when I needed it and at times that was a great thing to have.
The VA world is a lovely world for a lot of women who have gone through maternity. So it was a pleasure to have the business afterwards, even though there was obviously stuff I was suffering with personally.
It sounds like in many ways, having that business was part of the healing process because it gave you that part of your identity back, and you had that really safe supportive network around you.
Yeah, I think so. I think that’s an excellent point. It was probably part of my identity of no matter what there’s this to keep me going in a different way when I’m feeling concerned about all these other things that went on because of our child being in NICU.
How to manage and balance a 4-day working week
So now you work four days a week, more than you did when you were a full-time PA or VA. How do you maintain that balance and how easy is it to switch off on that fifth day?
It’s a constant managing of that. I’ve learned, and this is one thing probably a lot of entrepreneurs and business owners can identify with, my personality doesn’t switch off very well.
So that’s why I feel I might as well own a business, earn money, and do something I’m passionate about by not switching off very well, then pouring that into a company that may at some point not be the right fit for me.
So that’s kind of the first thing as well, is I’ve made peace with my personality type. But Wednesdays, yes, it’s a constant thing that I re-address all the time as well as also I do the school run.
So that does mean an earlier day most of the time a lot of the other days. But I do have my own personal assistant, and they run my inbox on Wednesdays completely. And that’s still a work in process, we’ve only just started that.
And being someone who has done a lot of this myself, I know that takes time. I have a community manager who helps me with the team. So anything on that side, everyone knows who the main contact is, especially on a Wednesday.
Wednesday I’m very strict on Mummy days. It doesn’t always work out. Occasionally I’ll have the odd meeting. I tend to leave that though if it tends to be another mum who knows what I’m doing and manage expectations on what’s going on my side.
But I think it’s something I constantly have to readdress and make sure I’m doing the right thing and make sure it works out and don’t try and overstretch myself, but also remember when I am working late in the evenings, that’s why.
And I wouldn’t change that. I really enjoy that flexibility right now and having that day with my child and knowing it’s there.
The biggest challenge is working out who your perfect client is
And so you are nearly three years into the business now. When you look back, what were some of those big early challenges, and what do you now wish you’d done differently?
Oh my goodness, I can’t believe it’s almost been three years.
I think, like with any business, who is the perfect Upsource client, who we want to work with, that’s still a process we’ve been going through.
And I’ve definitely seen a change in that, especially as we became a limited company and VAT registered. So that does change your client base naturally. And I’ve realised that as well.
What sort of team I want to work with, who works well with Upsource, who works well with me and the clients. I really do like a huge mix of characters on the team. So that means a different mix of clients as well.
Early days things, it was mainly small things. My website was on a host that wasn’t the right fit, so I changed it over to WordPress last year.
It was kind of smaller things, and I’m always, like any entrepreneur or business owner, just sorting out processes and making sure they’re all right, they meet the business needs that we have right now.
I’m a firm believer in a process and the right software, so I’m always re-evaluating them.
Your business reputation changes once you become VAT registered
To pick up on your point around working out who the right clients are for you, what does your perfect client look like?
And how did your reputation change when you became a limited company? Did it give you more gravitas and credibility?
Yes, it was interesting. I think it did it for me. It meant, right, okay, this is a business. We did it because we reached a certain level of income. That was really helpful. Also, I did then start to attract the clients that were VAT registered as well.
So it’s kind of how things worked out. It also meant they were on larger hours, which suits us, and the business and my time and the team’s time better is ones around on 30, 40-hour packages. Our core service is still personal assistant services, inbox, diary management.
So a lot of our perfect clients tend to be CEOs of whether it’s startups, scale-ups, SMEs, agencies, and also some corporate coaches because they don’t have a team, and they really rely on the freelancers around them.
So they’re a great client to have as well.
I did notice a shift after we became VAT registered. There were a few clients still coming in whom, in a different life I’d really like to work with in a different way, but just weren’t suitable and didn’t have the income that could afford Upsource at that time for us.
So it was a good shift at that time. It was a nice thing to go through. We went through quite a lot of growth, and now I think this year it’s just going to be a bit more meaningful and a bit more well planned, our growth.
What tasks should entrepreneurs and SMEs look at outsourcing?
So you work with a lot of entrepreneurs and SMEs. What’s your advice to them on what tasks they should be outsourcing?
Well, there’s a really, really simple thing you can do, which is note down your regular tasks. So that’s your daily, monthly, weekly, even ones that are ad hoc and annual things that end up falling on CEOs like registering your insurance and ICO which I talked about earlier.
Make a list of those or keep those in mind or do a brainstorm with someone, like a virtual assistant agency owner or a virtual assistant and get those tasks off your plate because those are the ones you can easily take off your plate. And I would start to get used to delegating.
You can’t grow doing it all yourself, that’s the fact, and you need to be able to let go of things. So starting with things like that would work really well. Also, think of things that you don’t like doing, shouldn’t be doing, hate doing. Those are excellent tasks to hand over.
So for example, I am not a writer. I’m not good at that. So I’ve always had someone doing the copywriting for me. And it actually gets done as well. I realised I had the aim to start a blog for a year, and now I have someone writing one for me twice a month, things like that.
Also have someone external take a look at your inbox and diary because sometimes when you’re so in it every day you feel, how would I hand this over? Where would I begin?
And the truth is it takes time, but you either invest in it now or invest in it later kind of thing.
So those would be some of my quick recommendations for figuring out how you can get help.
Focus on 3 goals for the week to keep yourself realistically disciplined
And in terms of delegation and managing your own tasks, are you quite disciplined with that? How do you manage your diary each day? What do you focus on?
Yes, so it’s a constant process. I did say to my VA, she looked at me like a true VA when I said, “Right on Thursdays I need to do this. And so that means I can’t do Thursday calls.”
And she was like, “At all?”
The look of fear on her face, bless her.
It is something I try and plan well because I think I’ve definitely gone through periods where I’m just on calls back-to-back each day and that doesn’t serve me or the business well. So trying to see how I can step away from that.
And that’s where they’re looking at the roles internally as well as just my calendar.
There are things I know I need to do every day. For example, we’ve talked briefly about PTSD and recovery, so I know I need to meditate every day. I need to move in some form every day because health is a priority now no matter what.
So there are things like that I need to prioritise in my day. Obviously I’m not perfect. Things crop up that are urgent with clients or VA’s, and I’m there for them. That’s my job.
But as long as I go into the week trying this, and I’m quite disciplined with my three goals for the week.
What the three things I really want to achieve? And when I’m not disciplined on that, it’s normally a sign that I need to re-address things again.
Your business is only as good as the people you recruit
And the team that you have around you are obviously so important. What are your tips and lessons on recruiting the right team?
I’m constantly learning with recruitment. It’s important to know that it’s not always going to work out. My friend worked in HR, and she once told me that it’s only like four in five hires that work out. So one doesn’t work out in every five, which was a really nice rule to know.
Because I think sometimes, especially in the VA world, we can take it quite hard on ourselves if something doesn’t work out. But it’s not always going to work out, it’s a people business.
I’ve listened to a lot of podcasts and a lot of things on people businesses outside the VA world to know the challenges that come with that.
But my top tip is always about the community. I’m really invested in the virtual assistant world and trying to always think about how can I be more invested in the virtual assistant world.
And that’s how you can find the best people ultimately is being ingrained in that community. And word of mouth referrals to VAs mean just as much as referrals to clients.
Actually, I said this to someone the other day, I chat to potential VAs more than I do potential clients. So I actually do invest more time in that because we’re only as good as the people we have on the team.
Managing virtual freelancers
And how do you manage a team of virtual freelancers? How tricky is that to keep tabs on everyone and lead a team?
I have the right people in place, so it’s not just me on that side. I have someone who helps me on the community, someone who manages the operations side of things as well as my own VA as well. So the pressure isn’t all on me.
Also with freelancers, it’s not managing them. It’s not in the same way that you would an employee. So there is a certain level of autonomy and trust that has to come from that.
But I’m also a stickler for a process.
So there are processes in place just to make things easier. And my key thing is communication. I can’t help someone if I don’t know about it.
So if someone comes to me with their problem or whatever they need to talk about or something they’d like to work on with a client or comes to my team about it, then that’s how we can work together the best way.
And I try to give the same back. I try to be quite open in return as well.
Being a performer vs an entrepreneur—which is scarier?
Talking of communication, I know that you have a background as a performer, so I’m wondering how that has shaped and impacted you as an entrepreneur.
And I think there’s a lot of credit to the background of singing and dancing, and I don’t think I’d be here on this podcast with you if I didn’t have a performer background.
There is nothing more terrifying than singing to a room full of people. I think I’m actually quite good at interviews and things because nothing is as scary as that.
There’s something very vulnerable, especially with singing, because it’s your voice and putting that out there.
So actually while I had all the fears that come with putting Upsource out there, especially when I felt like I had failed with redundancy.
And putting yourself out there with a business, I think when you’ve done that as a singer, I think you’re actually kind of used to doing the things that are scary and if you fail it’s okay.
The advantages of being surrounded by other entrepreneurs
You come from a family of entrepreneurs as well, do you think that made you less fearful of starting your own business?
Yeah, definitely having people I’d seen in my family run their own businesses, yeah, I think definitely.
My dad is an accountant, so as long as the finances look good I know I’m on track.
Did he check your finances?
Yes. He’s my accountant. And the first time I showed him my spreadsheet of what I wanted to do, he was like, “Yeah, okay.”
And then we sat down, and I was like, “I just want you to look at where we are.”
And he was like, “Oh, you’ve got a business here.” And I was like, “Yeah, thanks.” So that was nice.
But also, I do have, especially my husband’s friends, a lot of them have their own businesses, and it is nice to chat with that community.
I’ve never felt like one of those business owners that feels lonely in business because I know plenty of people that do it and plenty of people that don’t do it as well to remind me that I’m in quite a lucky position here.
How to scale your business but also know if you’re growing too fast
And you also work so closely with your clients, you’re always on the inside of a business.
What have you learned from them about scaling up a business, and what have you learned not to do?
For me, it’s hard because all business models are different in how they do things. I think coming from a place of trust is a great position to have.
Micromanaging isn’t going to get a scaling business very far from what I’ve learnt.
At the same time, I’ve always been quite wary that we had a period of fast growth at Upsource, and I don’t want to grow that fast again in the next few years because I never want to sacrifice growth for the people who are managing that within the business.
So that’s what I’ve seen sometimes from other businesses that I’ve been in.
I think it’s important to sacrifice your growth for the happiness of its people. I’ve not set up Upsource for that model of being just a financially driven business.
How do you know when you are growing too fast? What was the point where you felt that you needed to put the brakes on?
I think if it feels a bit unmanageable, and you are not proud of the output that you are giving other people, I guess. Because things happen, things change.
But I think if you need to re-address your time constantly and feel like you’re not achieving how you want your business to be run, I think you can find that out quite easily.
And you can see that if you are proud of what you’re achieving and what you’re doing each day.
Yeah, you can have days where you’re like, “That was crazy. What happened today?” Or, “This is a strange week.”
I’ve definitely had one of those recently.
But when you get to a point, you’re like, all these things have happened, but I’ve also managed to do this, you know then you are in a good position.
The future vision for Upsource
And what are your plans for growth? Where do you see Upsource going?
What’s your vision for the company?
Oh gosh, we’ve got plans.
So we’re definitely going to grow the next two years. Look at definitely expanding our core services to other clients, which are traditional virtual assistant support, inbox, diary management.
I can also see us expanding a little into providing HR support, more financial support, which we have started for some clients with the AML registration and things.
So definitely seeing what else we can do for them.
And we’ve got one client right now, we’re putting a really exciting structure in place for her business involving a chief of staff and a virtual assistant.
So I’d love to see what other clients would benefit from that sort of support from us coming in and supporting with that.
My business doesn’t keep me awake at night—just my kids
So there are lots of opportunities for growth.
What would you say are the biggest barriers at the moment? What’s keeping you awake at night?
I’m quite fortunate that doesn’t keep me awake. Maybe it’s because I’ve got two little babies that keep me awake.
I think there’s only so much time. I’d never want the business to sacrifice the happiness of me or the team. So that is always the first and foremost.
If it got to a point in the growth wasn’t being manageable, it’s either, we’ve got to re-evaluate the structure, bring someone else in place.
Or just put the brakes on the gears and be like, right, let’s re-address who are our clients again, who do we want to support?
And go back to the drawing board in that sense. Not completely at the beginning.
But no, I’m quite fortunate I don’t get kept awake by my business, just the kids.
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Want to know more about Upsource or Caroline Marshall?
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And you can find out more about Caroline on her LinkedIn.
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