Do things that don't scale
With Jack I am Ashley Paul Graham's essay, do things that don't scale
Aug 15, 2022•12 min•Ep. 28
Bootstrapped Digest with Ashley Baxter
A transparent account of bootstrapping an insurance business as a solo founder.
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Episodes
"This is so much bigger than me"
With Jack I am Ashley
Jul 18, 2022•13 min•Ep. 27
The road to automating my business
With Jack I am Ashley
Jul 04, 2022•15 min•Ep. 26
Product-market fit struggles
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...
Feb 15, 2021•16 min•Ep. 25
This is not a year in review
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
Jan 26, 2021•22 min•Ep. 24
My mid-Year review
Mid year review blog post Reflecting on a disappointing product launch SuperHi Scott, the freelancer I work with Follow me on Twitter
Jul 26, 2019•15 min•Ep. 23
Why can't I celebrate tiny wins?
With Jack Why can't I celebrate tiny wins blog post
Jun 28, 2019•13 min•Ep. 22
Mistakes I made when choosing a market
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...
Jun 19, 2019•18 min•Ep. 21
Reflecting on a disappointing product launch
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...
Apr 11, 2019•15 min•Ep. 20
The challenges of building an insurance business
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...
Mar 27, 2019•13 min•Ep. 19
Lessons learned from inheriting the family business
Before UpFront The family business With Jack
Mar 14, 2019•13 min•Ep. 18
Should you build a product for a user segment you're not a part of?
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
Mar 06, 2019•13 min•Ep. 17
How has the rebrand performed 4 months on?
How has the rebrand performed 4 months on? blog post With Jack The processes and reasons behind With Jack's rebrand My newsletter!
Feb 25, 2019•10 min•Ep. 16
Company/founder fit
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...
Feb 18, 2019•10 min•Ep. 15
In the trench tips for figuring out what problem you solve
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...
Feb 12, 2019•16 min•Ep. 14
2018: Year in review
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...
Dec 17, 2018•19 min•Ep. 13
How to start scrappy in a regulated industry
How to start scrappy in a regulated industry blog post With Jack
Dec 04, 2018•15 min•Ep. 12
Post-launch problems revisited
Post-launch problems revisited blog post Navigating a funk as a solo founder blog post With Jack
Nov 29, 2018•12 min•Ep. 11
The process and reasons behind With Jack's rebrand
The Process and Reasons Behind With Jack's Redesign blog post With Jack Sabine's case study Vic Bell's Dribbble Scott's website...
Nov 08, 2018•17 min•Ep. 10
Navigating a funk as a solo founder
Navigating a funk as a solo founder With Jack Epicurrence Tweet about momentum Tweet about being in a funk...
Sep 07, 2018•10 min•Ep. 9
Why I quit wedding photography
Why I quit wedding photography With Jack My photography
Aug 23, 2018•8 min•Ep. 8
Positioning your product to a tiny audience
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)...
Jun 11, 2018•17 min•Ep. 7
Bootstrapping Niice to 100,000 users
Niice Chris on Twitter
May 30, 2018•1 hr 4 min•Ep. 6
Start talking about your idea
Start talking about your idea With Jack Idea to Execution and Beyond Masters of Scale—How to price your product to scale
May 17, 2018•21 min•Ep. 5
My journey to 250 customers
Notist My journey to 250 customers
May 08, 2018•16 min•Ep. 4
The 'why' behind building With Jack
The 'Why' Behind Building With Jack blog post My YouTube channel Everybody's Winging It by Baremetrics Toad's Caravan
Apr 17, 2018•18 min•Ep. 3
How I improved With Jack's sign-up rate by 14%
All Day Hey! Improving With Jack's Sign-Up Rate By 14% Naomi Atkinson Design Scott Riley
Mar 22, 2018•11 min•Ep. 2
Minimum viable process
Links Minimum Viable Process With Jack What To Do If You Didn't Get Into Y Combinator Family holiday to Lanzarote Vic Bell From Scratch Minimum Viable Product Process Iterate...
Mar 14, 2018•18 min•Ep. 1
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