Filter by:

Reflecting on a disappointing product launch

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. The launch, however, was underwhelming. In this episode I dissect my disappointing product launch and share what I learned.

The challenges of building an insurance business

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 ‘disruptors’ anticipate. We’re seeing insurtechs challenge the status quo and execute beautifully, yet go out of business after a year. Here are some of my thoughts on the challenges of building an insurance business.

Lessons learned from inheriting the family business

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 in an industry I knew nothing about. Trying something new inevitably means making mistakes, but the upside is coming away from that experience having learned a lot. In this episode I share some of the lessons I learned and how I’m applying them to With Jack so I can avoid making the same mistakes.

Should you build a product for a user segment you're not a part of?

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 audience I knew nothing about before moving into a user segment I’m more familiar with. In today's episode I share my experience on both sides and my argument for building a product for a user segment you’re a part of (or familiar with).

How has the rebrand performed 4 months on?

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 niggling fear I had… Will this new website still make money? In this episode I dive into the numbers to see how the rebrand has performed and share a few lessons learned.

Company/founder fit

To take investment or not? It's a question I've struggled with since launching With Jack. The answer hinges on what kind of life I want to lead, therefore what kind of company I want to build. That was another question I've struggled to answer until I read Pat Flynn's book, 'Will It Fly?'. I share the exercise from 'Will It Fly?' that helped me get clarity on what's important to me in life and figure out what company/founder fit means to me.

In the trench tips for figuring out what problem you solve

In 2017 I applied to join an accelerator. Amongst all of the great advice I received from the programme, I kept hearing the same feedback about With Jack; “You aren’t solving a big enough problem”. In this episode I share the steps I took to figure out what problem With Jack does solve, but from a pain-point customer driven perspective.

© Ashley Baxter