Bootstrapped Digest With Ashley Baxter

With Jack I am Ashley Paul Graham's essay, do things that don't scale

With Jack I am Ashley

I've been MIA but this episode will explain why. This is the long, hard road to automating my business—a process that I'm 2.5 years (and counting!) into.

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.

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.

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?

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.

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.

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.

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.

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.

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).

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.

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 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.

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.

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?

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.

With Jack has a brand new look! I dive into the reasons behind the redesign, the process and what we tried to achieve. As always, I also share some things that didn't go to plan…

I've been feeling in a bit of a funk lately. It's a dangerous place to be as a solo founder because there's nobody to pick up the slack so you can recharge your batteries. I talk about identifying what triggered my funk and how I got out of it.