Ashley Baxter is currently building Jack, business insurance on a first name basis. She is also Director of Brokers Direct. Ashley likes video games, photography, and her dog, Indie. 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.

Because I enjoy taking pictures, people wonder why I didn’t instead pursue a career as a photographer. 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. 12 years, in fact. When I was 18 I inherited the family insurance business. Some parents leave their kids jewelry—maybe even a classic car. I got an insurance business.

Brokers Direct
The insurance business I inherited

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. 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 web site, so I built up experience creating table-based sites with inline styles. I didn’t realise how useful this would become later on in life.

Me when I was a drummer
Before insurance I was a drummer

Being the only person in the family with any knowledge of the web, it was only natural I took over the business. (Or as natural as it can be for a teenager with no business experience.)

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 reading policy documents.
  2. The industry was underdoing 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 that I couldn’t overcome was that buy-to-let didn’t interest me. And business 101 is that you should serve an audience you like. Insurance didn’t excite me either, but the challenges of the industry did.

That’s why I started With Jack. To address the challenges that I believe exist with insurance, but serve an audience that excites me. Freelancers in the creative field, like designers and developers.

Starting Jack wasn’t as straightforward as the first insurance business, which was handed to me after an unfortunate life event. 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 Jack to be. Years of exploring leads that never panned out. Years of hearing, “No thanks” from disinterested insurers.

Ashley on stage at DotYork
On stage sharing my first version of Jack

I almost quit. I’m glad I didn’t.

In August of ‘16—after over 2 years of pitching my business—I finally launched With Jack.

Ashley on stage at Hybrid Conf
The moment I shared With Jack with the world. Well, Berlin

That doesn’t mean the hard part is over. That’s what this blog is about. For documenting my journey bootstrapping a startup in the insurance space as a solo founder.

Spoiler: It’s tough, but I am ready for this!