Bootstrapped Digest with Ashley Baxter

Migrating ~ 1,400 customers to a new system without chaos. Here’s my plan 24.03.2026 19:37 ↓

The road to automating my business Vicky Gu

It's just a giant calculator 10.03.2026 12:17 ↓

My new system - tell your freelance friends? The  startups for the rest of us episode I was on

Do things that don't scale 15.08.2022 12:24 ↓

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

"This is so much bigger than me" 18.07.2022 12:41 ↓

With Jack I am Ashley

The road to automating my business 04.07.2022 14:56 ↓

With Jack I am Ashley

Product-market fit struggles 15.02.2021 15:58 ↓

Product-market fit struggles blog post With Jack Lenny's newsletter How to know if you've got product-market fit Reflecting on a disappointing product launch Lemonade's IPO breakdown

This is not a year in review 26.01.2021 21:31 ↓

This is not a year in review blog post 'Why do I need insurance?' guide The Jobs To Be Done Playbook My film photography My Twitter

My mid-Year review 26.07.2019 14:51 ↓

Mid year review blog post Reflecting on a disappointing product launch SuperHi Scott, the freelancer I work with  Follow me on Twitter

Why can't I celebrate tiny wins? 28.06.2019 12:40 ↓

With Jack Why can't I celebrate tiny wins blog post

Mistakes I made when choosing a market 19.06.2019 17:51 ↓

Thoughts on choosing a market blog post With Jack Should you build a product for a user segment you're not a part of? Five ways to build a $100 million business Justin's Twitter thread about fishing

Reflecting on a disappointing product launch 11.04.2019 15:21 ↓

Reflecting on a disappointing product launch blog post Rome selfie while I'm on the phone to customers My new product A post-mortem on shutting down a product we just launched

The challenges of building an insurance business 27.03.2019 12:37 ↓

The challenges of building an insurance business blog post Kinsu The Digital Insurer With Jack World's only public benefit insurance company, Lemonade My photography business

Lessons learned from inheriting the family business 14.03.2019 12:42 ↓

Before UpFront The family business With Jack

Should you build a product for a user segment you're not a part of? 06.03.2019 12:51 ↓

Should you build a product for a user segment you're not a part of blog post The family business With Jack's new product, legal expenses @iamashley on Twitter

How has the rebrand performed 4 months on? 25.02.2019 9:36 ↓

How has the rebrand performed 4 months on? blog post With Jack The processes and reasons behind With Jack's rebrand My newsletter!

Company/founder fit 18.02.2019 9:53 ↓

Company/founder fit blog post With Jack You want more than product/market fit Will it fly? My freelance photography blog Patreon, venture capital and the loss of the win-win

In the trench tips for figuring out what problem you solve 12.02.2019 15:36 ↓

In the trench tips for figuring out what problem you solve blog post With Jack The Ultimate List of Customer Development Questions Ignite From Scratch My Twitter

2018: Year in review 17.12.2018 18:49 ↓

2018: Year in review blog post With Jack With Jack's YouTube channel With Jack is now authorised by the FCA blog post My trip to Lanzarote My trip to Amsterdam My trip to California My trip to Dubrovnik

How to start scrappy in a regulated industry 04.12.2018 14:44 ↓

How to start scrappy in a regulated industry blog post With Jack

Post-launch problems revisited 29.11.2018 12:15 ↓

Post-launch problems revisited blog post Navigating a funk as a solo founder blog post With Jack

The process and reasons behind With Jack's rebrand 08.11.2018 17:15 ↓

The Process and Reasons Behind With Jack's Redesign blog post With Jack Sabine's case study Vic Bell's Dribbble Scott's website

Navigating a funk as a solo founder 07.09.2018 9:47 ↓

Navigating a funk as a solo founder With Jack Epicurrence Tweet about momentum Tweet about being in a funk

Why I quit wedding photography 23.08.2018 7:54 ↓

Why I quit wedding photography With Jack My photography

Positioning your product to a tiny audience 11.06.2018 17:03 ↓

Positioning your product to a tiny audience blog post How Seth Godin Would Launch A New Business With Jack Justin Jackson's article on founder / market fit SaaS pricing advice (Build Your SaaS podcast)

Bootstrapping Niice to 100,000 users 30.05.2018 1:03:42 ↓

Niice Chris on Twitter