Bootstrapped Digest with Ashley Baxter

Aug 15 2022 28 ep. 16 mins 20

Bootstrapped Digest with Ashley Baxter Podcast artwork

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

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Do things that don't scale

Aug 15 2022 12 mins

In Paul Graham’s essay, do things that don’t scale, he talks about you acting as the software, doing things manually that you plan to automate later. Currently I’m the software. I process quotes, renewals, cancellations and everything in between. The automated quote and bind system is in development, but there are so many benefits of doing things that don’t scale. Let's tal

"This is so much bigger than me"

Jul 18 2022 12 mins

Following on from the last episode where I talked about why now is the right time to automate the business, in this episode I go into more detail about what’s required to do that. To date this has been a 2.5 year process and it hasn't been without its bumps in the road. I think I'm the first one-person business to go through this process and I feel so overwhelmed.

The road to automating my business

Jul 04 2022 14 mins

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.

Product-market fit struggles

Feb 15 2021 15 mins

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.

This is not a year in review

Jan 26 2021 21 mins

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.

My mid-Year review

Jul 26 2019 14 mins

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?

Why can't I celebrate tiny wins?

Jun 28 2019 12 mins

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.

Mistakes I made when choosing a market

Jun 19 2019 17 mins

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.

Reflecting on a disappointing product launch

Apr 11 2019 15 mins

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

Mar 27 2019 12 mins

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.