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 through some of the popular definitions and talk about how With Jack measures up.

Bootstrapped Digest with Ashley Baxter

Product-market fit struggles

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 share the challenges of the past year and the lessons I learned. We're still not out of the woods yet, but I now feel ready to talk about the impact the pandemic has had on my business.

This is not a year in review

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 I set myself and do a mid-year review. How am I doing? Am I on my way to achieving them, have they evolved into something new, or have I shelved them completely?

My mid-Year review

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 happened. My friends said I was in shock. Over a week has passed and I’ve had plenty of time to let this achievement sink in. In this episode I talk about why I’m finding it difficult to celebrate my tiny wins.

Why can't I celebrate tiny wins?

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 I’ve chosen an ideal market to sell to and I want to share some of the factors I wish I’d considered beforehand. If you’re starting a business you will want to consider these factors, too.

Mistakes I made when choosing a market

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.

Reflecting on a disappointing product launch

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.

The challenges of building an insurance 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.

Lessons learned from inheriting the family 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 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).

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

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.

How has the rebrand performed 4 months on?

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.

Company/founder fit

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.

In the trench tips for figuring out what problem you solve

It's time to look back on 2018! The highs, the lows and notable moments. Two things stand out to me about 2018: the progress I’ve made on With Jack and the trips I’ve taken. However, it hasn't all been great. I also share some end-of-year figures for With Jack.

2018: Year in review

Insurance is one of the least start-up friendly industries in the world. It's a regulated industry, so you can't just have an idea, buy a domain and start making money. You'll need to be licensed to sell insurance, and that takes between 6-12 months and costs thousands of pounds. For those of us who don't want to raise, how can you quickly and cheaply get started in insurance?

How to start scrappy in a regulated industry

In this episode I revisit some of the problems I faced post-launch. I talk about what I've learned, if I've solved those problems and some of the new challenges I'm facing in my second year in business.

Post-launch problems revisited

A transparent account of bootstrapping an insurance business as a solo founder.

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Bootstrapped Digest with Ashley Baxter

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