Ashley Baxter is currently building With Jack. Ashley likes video games, photography and strongwoman. She is based in Glasgow, Scotland.

My story

Most people who save £10,000 wouldn’t use it to start an insurance business, yet that’s what I did.

People wonder why I didn’t pursue a career as a photographer because I enjoy taking pictures. On the surface it’s more creative and interesting than insurance.

The most common question I get asked is, “Why insurance, Ashley?”.

Actually, that’s not true. It’s “What camera do you use?”, but this would be a different story if I took that direction.

The insurance industry and I go way back. Over a decade, in fact. When I was 18 I inherited the family insurance business. Some parents leave their kids jewelry. Maybe even a classic car. My dad left me an insurance business.

My dad had built a successful online business selling buy-to-let insurance. When he passed away in 2005, somebody needed to take the reins. Because I was the only person in our family with experience building websites, that somebody was me.

Prior to this I had been studying a practical music course at college. I was a drummer in a band and we needed a website, so I created a table-based website with inline styles. I didn’t realise how useful this would become later on in life.

There were a few problems:

  1. I had no idea how to run a business. Or about insurance. I had to learn everything from sales and marketing to understanding insurance terminology. While the rest of my friends were embracing student life, I was at home reading policy documents.
  2. The industry was undergoing a huge shift. People were moving away from Google to shop for insurance and turning to comparison sites. My dad had built his whole business model around Google.

The business suffered as a result.

But the biggest problem was me. I could never overcome that buy-to-let didn’t interest me. Business 101 is that you should serve an audience you like. Insurance didn’t excite me either, but the challenges of the industry did in terms of its prehistoric tech and poor design.

That’s why I started With Jack. Originally it was to address the challenges that I believe exist within insurance whilst serving an audience that excites me. Creative freelancers.

Starting With Jack wasn’t as straightforward as I thought it would be. Because I didn’t have a book of customers, any contacts in the industry or qualifications, getting started took a long time.

Years of traveling around the UK, pitching my vision of what I wanted With Jack to be. Years of exploring leads that never panned out. Years of hearing, “No, thanks” from disinterested insurers.

I almost quit. I’m glad I didn’t.

In August of 2016—after over 2 years of pitching my business—I finally launched With Jack.

That doesn’t mean the hard part is over. That’s what this blog is about. For sharing my journey bootstrapping a startup in the insurance space as a solo founder, and documenting my goal of helping 10,000 freelancers.

With Jack was initially born out of frustration around prehistoric tech and poor design in insurance, but something happened as I started building With Jack. I realised the design and tech doesn't matter anywhere near as much as I thought it would. That's not the problem I want to solve.

My 'why' is to help you be a confident freelancer.

Subscribe to my newsletter