Meet 'With Jack': Business insurance for freelancers
We talk to Ashley Baxter, Founder of With Jack, simple business insurance for freelance creatives with a personal touch.
When you start working for yourself insurance isn’t one of the first things you think of. There’s way too much to do what with working out what you’re good at, what you want to do, what your rates should be, who to contact, setting up your pipeline, maybe building a website…..the list goes on. Even if it does enter your mind for a nano second, the threat of jargon and corporate words, never ending forms and paying out for something when you don’t actually need it is enough to put any freelancer off.
So we breathed a sigh of relief when Dave from Work Notes told us about Ashley from With Jack. Insurance designed for freelancers, one solid policy created exactly for what you need, no jargon and over complicated phrases and clear pricing - hurrah! On top of this, Ashley is lovely, works hard, really knows her stuff, is responsive and there when you need her and is self-employed herself so she really gets you. Yep, it’s like the cherry on top of a business essential cake!
We talk to Ashley about how she created With Jack after taking on her Dad’s insurance company after his death. How she taught herself coding, used modern technology, her personal experiences and interest in design to create a modern-day insurance company with the self-employed at it’s heart.
“Because deadlines can be missed, client expectations can be difficult to meet, mistakes can happen. By being insured you’re removing the pain of finding a lawyer as well as the expensive fees. There’s also the emotional support. As an ex-freelancer I would also say being insured gives you the confidence to stand up to clients. That’s priceless.”
Hey Ashley and welcome to The To Do List! Tell us a little bit about yourself.
Hello! I’m Ashley. I like video games, photography and weightlifting. I’m building With Jack. We help keep freelancers in business by supporting them legally and financially if they have problems with a client. In other words, business insurance!
I used to be a drummer and studied drumming at college with the intention of becoming a session musician. Just after my second year my dad passed away and left his insurance business to me. I was 18 at the time and it was a property insurance business, so you can imagine it didn’t really excite me. I gave up my dream of becoming a drummer and worked on my dad’s business, but I wasn’t very happy.
I got into photography along the way, which did excite me, and started freelancing on the side. I freelanced for 6 or 7 years. Despite not being interested in property insurance, I was interested in the insurance industry and how bad the design and technology was. It’s gotten a lot better now, but my interest in design and tech was ultimately what lead to me starting my own insurance business.
“ I taught myself to code and built a quote system for my dad’s business. We took a complicated onboarding process and simplified it with modern technology and clever design.”
Where did the idea for With Jack first come from?
I mentioned being interested in design and technology. I taught myself to code and built a quote system for my dad’s business. We took a complicated onboarding process and simplified it with modern technology and clever design, but the insurer we partnered with had no interest in allowing me to implement it. It was frustrating having to use their legacy systems, so I started considering moving on and creating my own business where I’d have more creative control and freedom.
At the same time I was freelancing as a photographer and had struggled to understand what insurance I should have for that. I bought some business insurance but had no idea if it would actually help me and just crossed my fingers that I’d never have to use it. I knew I had concerns like my CF card flaking during a wedding, but I wasn’t sure what insurance, if any, could help me with those fears.
When it came time to starting my own insurance business, I thought that would be a good problem to tackle. It made sense because I was interested in serving that audience (freelancers and creatives), and had also freelanced for several years so had experienced my own problems with clients.
Such a great story and sounds like it was meant to be!
Talk us through the services With Jack offers and who you’re aiming them at
At the moment we have 4 insurance products on our website with more to come. I’ll go over them quickly and try to avoid insurance jargon!
Our main product we arrange for freelancers is professional indemnity insurance. It’s an incredibly meaty cover, but I like to simplify it by thinking of it as insurance for careless mistakes or problem clients. Common situations we see that this product helps with include delivering work late or missing project milestones. This can lead to claims of loss of income. Poor project scopes meaning you and the client are on different pages in regards to what work is to be expected. This can lead to legal threats. There’s so much more. I cover a lot of these stories on my podcast, Unsure? Insure!.
Then there’s legal expenses insurance. The name of this product can be confusing because the professional indemnity policy does include legal fees for defence costs. Legal expenses insurance is designed to provide you with legal assistance and advice before a claim arises. There’s a legal advice and tax helpline, a service where a solicitor will chase overdue invoices on your behalf, legal documents and more.
We also arrange contents insurance, which is self explanatory. Most freelancers are dependent on at least one bit of kit to do their work. This is definitely the product we get the most claims for. Broken laptops, stolen bags. That kind of thing.
Then there’s public liability insurance. Because most of our customers work remotely, we’ve never had a public liability claim but a lot of clients ask freelancers to have this insurance. It would cover you if a client or member of the public sustained an injury as a result of your work activities.
Most of our customers are freelancers, although we do get some small businesses using With Jack. We’re quite focused on those in the design and technology sector, but we have a lot of customers on the fringes of that. Copywriters, digital markers, photographers etc.
How did you go about launching? Did you need to raise any funds, create your own branding etc.
Insurance is one of the least start-up friendly industries in the world. Because it’s a regulated industry there can be a lot of hoops to jump through and you need a bit of capital to get started.
I used the money I earned as a freelance photographer to launch the first version. Shooting weddings on weekends and picking up bits and pieces of commercial work helped me to cover the cost of the design, branding and initial quote system. I got a good freelance gig doing photography for Glasgow City Marketing Bureau, and then I was aiming to shoot 10 weddings a year. All of that helped financially, although as With Jack grew it did get to the point I was struggling to juggle it all.
We’ve since re-branded and are in the process of building an automated quote and bind system (currently all quotes and policies are manually processed!). Now that With Jack is a lot more established I’ve been able to use the profits from the business to invest in this. I quit freelance photography and went full-time on With Jack in 2018.
Tell us about the name - where does it come from and what does it mean?
I knew I wanted With Jack to have more of a human feel than other insurers and I wanted the name to reflect that (initially our tagline was ‘business insurance on a first name basis’). Because my dad got me into the industry I wanted the name to have a nod to him. I’m not great at naming things, so I decided to just name it after my dad, Jack. Of course a domain like that isn’t available so it had to be With Jack!
“ I love helping customers. It’s very satisfying when you can help a freelancer understand their insurance, make something a bit easier for them or help them to navigate a scary situation that they might have had to deal with alone.”
What steps of creating and growing With Jack has surprised you the most? What parts have you enjoyed and which parts have been difficult?
The hardest part has been navigating the regulatory landscape. I mentioned before that insurance isn’t a start-up friendly industry. It took me years to launch With Jack because I wasn’t sure how to even start. Since launching, insurance has become quite a ‘hot’ scene for investors, so I’ve had to compete with a lot of funded competitors popping up. That’s not been fun because With Jack is bootstrapped so we grow a lot slower, whilst they have bigger teams and resources and can undercut you with prices.
The most surprising part that I’ve enjoyed has been customer service. I thought I’d enjoy building features and coding, but I love helping customers. It’s very satisfying when you can help a freelancer understand their insurance or make something a bit easier for them, and it’s also incredibly satisfying to help a freelancer navigate a scary situation that they might have had to deal with alone prior to being insured.
With all the balls to juggle, insurance isn’t often at the top of a freelancers to-do list. Tell us why it should be…
Because deadlines can be missed, client expectations can be difficult to meet, mistakes can happen, and every freelancer will at some point have a client who turns out to be a bad apple through no fault of their own.
By being insured you’re removing the pain of finding a lawyer that’s specialised in a particular area as well as the expensive fees. If a client wants compensation or damages, you’re removing the financial burden of having to pay for those costs yourself. There’s also the emotional support element. As an ex-freelancer who had a horrible situation with a client but never had to claim on their insurance, I would also say being insured gives you the confidence to stand up to clients. That’s priceless.
What problems and obstacles do freelancers often encounter around insurance?
I might be wrong about this and I’m happy to be corrected, but I think the two biggest obstacles are, what insurance products do I buy? What situations does this insurance product help me in?
Freelancers aren’t walking around thinking, “I wish my insurance had a mitigation costs clause”. Instead they’re thinking, “I hope my client pays me. I hope my project runs smoothly. I hope my client is happy”. We talk about the situations insurance can help freelancers with on our website and podcast, but it is something we’re always working on improving because once freelancers have a better understanding of how these products can help them they can then make better decisions about what products to buy.
“my own experience as a freelancer helps me bridge the gap between creative and insurer. With Jack is focused on a particular niche which means you won’t be buying products you don’t need or answering questions that aren’t relevant to what you do”
Who do you see as your main competitors and why is With Jack different and better?
The largest digital insurance broker for businesses in the UK is Simply Business. I had my insurance with them when I started freelancing and never had to claim, so I can’t comment on being better. What makes With Jack different is a few things.
Firstly, my own experience as a freelancer helps me bridge the gap between creative and insurer. Secondly, because With Jack is focused on a particular niche it means you won’t be buying products you don’t need or answering questions that aren’t relevant to what you do. We’ve had a lot of freelancers come to us with insurance products that aren’t applicable to their business because they’ve bought it from a place that tries to cater to every business. Lastly, we don’t charge any admin or cancellation fees like a lot of companies do, and we have a monthly plan that provides more flexibility over your insurance so it can change as your business does.
What are your plans and hopes for the future of With Jack...what’s next?
We exist to help keep freelancers in business, so every decision on new features and products is influenced by that. In the immediate future we’re launching something that can hopefully help our customers find more work during the COVID-19 pandemic.
We’re also in the process of becoming a Lloyd’s Coverholder. Whilst that sounds like boring insurance stuff it means we can have a role in creating better products for our customers. This also allows us to launch the quote and bind system and customers will be onboarded to a dashboard which is going to make managing and understanding their insurance a lot easier.
So, better products, better features and better tech!
Give us your top 3 recommendations - podcasts, books, people to follow, sources of inspiration…
Podcast: Build your SaaS. A transparent insight into bootstrapping a business in 2020
Person to follow: Asia Matos. I recently started following Asia after watching a fantastic webinar with her on growth
An Instagram feed I enjoy for inspiration: Ruben Hughes. An art director in Copenhagen who posts simple but beautiful photos
What were you doing this time last year? What have you learnt or how have you changed since then?
This time last year I was gearing up to move into a new office space, which is now sitting empty due to Coronavirus. We’ll get back into our office at some point, but so much has changed now due to this pandemic. It’s made me appreciate the time I spend with friends and being around other people, which is a good thing because I can be too focused on work and shut myself off.
Get insurance ticked-off your to-do list, only pay for what you need and know that you’re in safe hands.
Get in touch with Ashley over on the With Jack website.