Caroline Marshall

We sit down with Caroline Marshall, the dynamic founder of Upsource, host of the Bump to Business Owner podcast, and mum to two boys aged five and three. Upsource, an award-winning Virtual Assistant agency, has been a pillar of support for businesses of all sizes since its inception in July 2020.

Caroline shares her journey of building a thriving agency that caters to SMEs, tech startups, and HNW individuals while managing financial admin, operations, and social support. Additionally, she discusses her passion project, the Bump to Business Owner podcast, launched in summer 2023, which serves as a vital community for women and mums balancing founder life with family responsibilities.

Can you share your journey of entrepreneurship from the time you decided to start your business to where you are now, considering the significant milestones of trying to conceive, pregnancy, and post-partum?

Mine was an untimed pregnancy, and I wasn’t ready. I wasn’t ready to take a step back from my career, we weren’t ready financially and, as first in my circle to have a baby, I felt really isolated. Post maternity leave, my return to work at a startup Virtual Assistant agency (at 8 weeks postpartum) was badly handled and followed by redundancy, which really knocked my confidence.

When Covid came around, I found myself furloughed, pregnant with my second, and main carer to my first child with an uncertain future. So I decided to launch my own VA business and take control of my own career.

I launched Upsource in July 2020, timed to coincide with my eldest’s nursery reopening. I had booked enough clients to replace my previous income, which was absolutely huge for me. That money was necessary to keep my eldest in nursery 4 days/week so I could work. Managing that while pregnant, pre the nursery return and in a pandemic is a huge achievement for me.

I had planned on a 6 month maternity leave when the business was 6 months old: I moved into the agency model and had a team of 5 by that point. Building maternity leave into my business plan was one of the best business decisions I have ever made, as my youngest was taken into NICU shortly after birth and I just wasn’t able to be present for the business at that time.

My returns to work were all big milestones for me, as my previous return had been so early and so difficult. In August 2021 I went back to work 2 days/week, January 2023 for 3 days and September 2024, I was back to work 4 days a week. Since then I have kept to working 4 days a week, so I can have my Wednesday ‘Mummy day’. From September 2024, my eldest will be starting school and I will be working 5 days/week school hours. I am so proud to have kept my Wednesdays up till now and made it work, even though the boundaries are sometimes not as clear as they could be!

What were the unique challenges you faced as a female entrepreneur while going through the process of trying to conceive, pregnancy, and post-partum? How did you navigate these challenges?

I felt very isolated in my first pregnancy and return to work, so I was determined not to feel isolated as a business owner. I have really sought out and built relationships and community within the Virtual Assistant industry and with female founders. For the first year or so of my business, we were in lockdown so traditional networking events weren’t taking place, however ,as a pregnant founder and then mum of a newborn, the Covid era online networking actually worked in my favour.

I’ve learnt from my own experience and from speaking to other female founders on the podcast that maternity leave in some shape or form is absolutely essential. Whatever it might look like for you and your business and family, we need some time to recover, emotionally, hormonally and physically.

I have built a team from the very start of Upsource to support both me personally and the business; I could not do this without them, time is not a luxury I possess. From bookkeeping, to operations, content to lifestyle support, my team is essential to my success. They were essential in my maternity leave, my worst case scenario planning (which unfortunately was absolutely necessary in my case), and in building my business.

Male founders just don’t have to build family planning into their business in the way that female founders do.

Male founders just don’t have to build family planning into their business in the way that female founders do. Whilst we have to be so prepared in business (and don’t get me started on the maternal load!), we also need to be able to take time to ourselves and relax as we transition through the various stages of pregnancy and motherhood; it’s tough!

After my second son’s stay in NICU, I had to invest a lot of time in the early years to process that trauma. It was hard, and made harder as I balanced being needed by my team as well as my family. Therapy has been fundamental to my recovery, and in being present for both. I have been using EMDR therapy, habit stacking and have been working on communicating my needs and setting boundaries that I need whilst not limiting my growth and the growth of my business.

How did you manage your business responsibilities while dealing with the physical and emotional aspects of pregnancy and post-partum recovery?

During pregnancy I had to learn to really lean into the energy I had available. I didn’t rush into launching my business in my first trimester as I wasn’t feeling great while navigating lockdown with a toddler. My body started saying ‘no’ when I pushed things too much in my second trimester, so I started planning to hand over clients to my team and start maternity leave earlier. As it turned out, I stuck to the original time frame, but then came NICU.

My team, and especially my community manager, Soo, absolutely saved me. As part of my worst case scenario planning, my husband knew who to contact and then my team didn’t come to me until I opened myself up to communications when I was ready. In reality, I was invoicing clients within a month of my second’s birth (although we didn’t have many clients at the time!).

My business gave me such joy during a really difficult time; something to focus on and give me hope that my career could be what I wanted it to be when I was ready. That being said, I had some really hard moments when managing PTSD, my emotions, the family and the business were too much. But I had to learn to ask for help, and sometimes tell my team I just couldn’t be present.

Did you experience any changes in your entrepreneurial mindset or approach during pregnancy or after becoming a mother? If so, how did these changes manifest?

My big mindset shifts happened with my first son when I was employed full time. But my main realisations with my second and running a business was that I can have a career and be flexible; working flexibly doesn’t mean that I’m not ambitious. And that ultimately, I love my business, but my family is my priority and if the business doesn’t work out, it’s OK. I’ve got a lot more perspective now. Perspective doesn’t mean less passion or drive, it’s just a healthier approach.

What support systems or resources were most beneficial to you during your journey as an entrepreneur navigating pregnancy and motherhood?

The VA communities I joined were and are so important to me in building my business, as was VACT and my mentor. My family was also central, in particular, my dad who is an accountant, and is the first person I brought onto the Upsource “team”. My team, and my lead contact were a huge support. And, of course, my husband, who really ‘gets it’ and supports me and the business.

I searched a lot for resources for mums and founders and just didn’t find what I needed, which is why I launched my podcast: Bump to Business Owner.

Reflecting on your experience, what are some successes or achievements in your business that you attribute to your journey through trying to conceive, pregnancy, and post-partum?

Building the business in the agency model is a success for me, as I had to plan for maternity leave and to step away from client work. My maternity leave, although very difficult, was an excellent lesson that I can rely on my team, and completely step away from the business if I need to; it’s nothing to be scared of.

Conversely, what were some of the biggest obstacles or setbacks you encountered as a female entrepreneur during this period? How did you overcome them?

I think many of the obstacles that I faced are the same as every female entrepreneur and mother: the maternal load, the lack of time when ‘balancing’ family and business needs and the hormonal rollercoaster, which means my peers and I just can’t work the same way traditionally a man can in the post birth years without a huge team of household staff.

Recovering from having a very sick baby, where for a while we didn’t know ‘what life would look like’ was life changing, navigating this, business as a postpartum woman was process and when ready I have worked through with a combination of therapy, gratitude journaling and ice baths amongst other things.

In hindsight, what additional support or resources do you wish you had access to during your journey through entrepreneurship while being pregnant and a new mother?

During both my pregnancies I searched for resources for career women who were also mums; I wanted to hear the stories of successful, ambitious women balancing that with family life. I couldn’t find what I was looking for, which is why I launched my podcast Bump to Business Owner last year.

How did you balance the demands of entrepreneurship with the needs of your child during their early years? What strategies or techniques proved most effective for you?

Excellent diary management was key, and setting strong boundaries with clients and my team to make sure my Wednesday/Mummy Day doesn’t get encroached on (although let’s face it, it happens!). I use wraparound care at least once a week, and I refuse to feel guilty about it. Everything is a phase, and once school hours arrive for my second later this year, we will have to change our approach and find another way of making things work.

As founder of an outsourcing business, I of course, have lent into outsourcing as much as possible! Asking for help from friends and family where it’s needed, and outsourcing in my business. At first, I prioritised outsourcing from a business perspective, but we have brought in a cleaner which has been a game changer!

My team and I have also put a lot of work into getting our automations, systems and processes in order, so I don’t have to be present all the time. My team has signed new clients without me. I want to be a founder that can take a few weeks off if necessary and for the business to keep moving without my being hands on.

Getting out and networking has been central to the growth of my business, and that has been tricky at times with a young family. I make it a business priority where I can, but sometimes it’s just not possible, and that’s OK. I am very aware that everything in parenthood is a season, and if I can’t make something work right now, there will be another time for it.

Looking ahead, what advice would you offer to other female entrepreneurs who are either considering starting a family or are already juggling entrepreneurship and motherhood?

It is possible; we get to be both. But it’s going to look different for everyone, so let’s leave behind any comparison, judgement and guilt. Ask for help, and help where you can. Listen to and support other mums. And absolutely ban the phrases, “at least...” and “enjoy every minute”.