Bootstrapped Digest with Ashley Baxter

Ashley Baxter

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

30 Episodes

Migrating ~ 1,400 customers to a new system without chaos. Here’s my plan
3/24/2026
19:37
The road to automating my businessVicky Gu
It's just a giant calculator
3/10/2026
12:17
My new system - tell your freelance friends?The startups for the rest of us episode I was on
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Do things that don't scale
8/15/2022
12:24
With JackI am AshleyPaul Graham's essay, do things that don't scale
"This is so much bigger than me"
7/18/2022
12:41
With JackI am Ashley
The road to automating my business
7/4/2022
14:56
With JackI am Ashley
Product-market fit struggles
2/15/2021
15:58
Product-market fit struggles blog postWith JackLenny's newsletterHow to know if you've got product-market fitReflecting on a disappointing product launchLemonade's IPO breakdown
This is not a year in review
1/26/2021
21:31
This is not a year in review blog post'Why do I need insurance?' guideThe Jobs To Be Done PlaybookMy film photographyMy Twitter
My mid-Year review
7/26/2019
14:51
Mid year review blog postReflecting on a disappointing product launchSuperHiScott, the freelancer I work with Follow me on Twitter
Why can't I celebrate tiny wins?
6/28/2019
12:40
With JackWhy can't I celebrate tiny wins blog post
Mistakes I made when choosing a market
6/19/2019
17:51
Thoughts on choosing a market blog postWith JackShould you build a product for a user segment you're not a part of?Five ways to build a $100 million businessJustin's Twitter thread about fishing

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Bootstrapped Digest with Ashley Baxter

Ashley Baxter

30 Episodes

Migrating ~ 1,400 customers to a new system without chaos. Here’s my plan

It's just a giant calculator

Do things that don't scale

"This is so much bigger than me"

The road to automating my business

Product-market fit struggles

This is not a year in review

My mid-Year review

Why can't I celebrate tiny wins?

Mistakes I made when choosing a market