Who are you? 
I’m Ashley Baxter, founder of With Jack.

What does your business do?
We arrange business insurance for freelancers in the digital sector. We’re not reinventing the insurance business model, but taking what works and making it work for today.

That means building a transparent company and creating a customer journey that’s tailored towards freelancers. We use simple technology and clever design to remove barriers, making it more accessible for freelancers to get the cover they need.

Where are you based? 
I’m building Jack from Fairfield Shipyard, Govan. I’m paying £210 a month for a desk at RookieOven, a co-working space for startups. It’s an affordable solution for access to high speed broadband as well as local talent. Oh, and I get to bring my dog to work!

How did you get started?
I got started with £10,000 I’d saved doing wedding photography at the weekends. I put this towards design and development costs to build Jack’s quote system and develop the brand.

What is your background?
I inherited my late Dad’s property insurance business when I was 18. I was studying drumming at college, expecting to chase the rock ’n’ roll dream, but my career path changed overnight.

I had no qualifications in insurance or a university degree. Instead I’m self-taught. I’ve learned marketing, sales, how to code and many of the other skills required to run a small business and launch a startup.

I’ve also been studying for my insurance qualifications and have passed my first exam.

What is your top tip?
In terms of getting a business off the ground, acknowledge that the final 20% is going to be the hardest. There will be moments when the excitement fades, it gets harder and less fun. That’s when most people quit. You’ve got to keep going through that really hard, really not fun part—that’s where the reward is.

How long has your business been running?
I soft-launched With Jack in August of 2016 on stage in Berlin to an audience of 200 people. I officially launched in September, 2016. We’ve now put close to 70 freelancers on cover. A lot of these people are buying insurance for their business for the first time, and it’s something they hadn’t considered until hearing about With Jack.

Who is your inspiration? 
My Dad. He is the reason I got into insurance, and that’s why I named my new business after him — a nod to the person who set me on this path.

Where do you plan your business to be in five years time? 
If you mean location-wise, I plan on staying in Glasgow but building a remote team. This gives me the best of both worlds.

An affordable base to build a business from, but accessing talent from all around the world. Ultimately, I want Jack to become the go-to insurance provider for freelancers and creative in the digital sector.