Despite being 4 years into building With Jack I'm not convinced I have product-market fit. Everyone has a different definition of what PMF is, so I go...

I'm back with a long overdue update! In this episode I document what it was like bootstrapping my business through a pandemic as a solo founder. I sha...

We're 55% of the way through 2019! Coupled with the start of summer being quieter for my business, now seems a good time to revisit some of the goals ...

Last week With Jack hit a huge milestone. Despite this being something I have been working towards for so long, I didn’t feel anything when it happene...

Before starting my business I hadn’t given much thought to what goes into choosing a good market. I love targeting freelancers, but that doesn’t mean ...

In March I launched a new product. I was excited about this product because it has a myriad of features that solve problems freelancers face regularly...

Another UK insurtech has closed its doors. Insurtech or not, VC-funded or not, building a business in the insurance space is a lot tougher than all us...

In 2005 I inherited an insurance business from my late Dad. Weeks earlier I had been studying music at college. It was big leap to running a business ...

A podcast listener emailed me the question, "Would you build a product for a user segment that you're not a part of?". I’ve built a product for an aud...

4 months ago we shipped a major update to With Jack. A brand new look plus instant quotes! Once the post-launch dust had settled there was one nigglin...