Bootstrapped Digest with Ashley Baxter
28 episodes - English - Latest episode: over 1 year ago - ★★★★★ - 2 ratingsA transparent account of bootstrapping an insurance business as a solo founder.
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Episodes
Do things that don't scale
August 15, 2022 07:00 - 12 minutes - 11.4 MBWith Jack I am Ashley Paul Graham's essay, do things that don't scale
Product-market fit struggles
February 15, 2021 20:37 - 15 minutes - 14.7 MBProduct-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
January 26, 2021 21:52 - 21 minutes - 19.8 MBThis 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
July 26, 2019 12:35 - 14 minutes - 13.7 MBMid 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?
June 28, 2019 09:40 - 12 minutes - 11.7 MBWith Jack Why can't I celebrate tiny wins blog post
Mistakes I made when choosing a market
June 19, 2019 16:20 - 17 minutes - 16.4 MBThoughts 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
April 11, 2019 09:30 - 15 minutes - 14.1 MBReflecting 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
March 27, 2019 14:00 - 12 minutes - 11.6 MBThe 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
March 14, 2019 14:10 - 12 minutes - 11.7 MBBefore UpFront The family business With Jack
Should you build a product for a user segment you're not a part of?
March 06, 2019 18:00 - 12 minutes - 11.8 MBShould 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?
February 25, 2019 18:30 - 9 minutes - 8.85 MBHow 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
February 18, 2019 13:30 - 9 minutes - 9.1 MBCompany/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
February 12, 2019 11:40 - 15 minutes - 21.5 MBIn 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
December 17, 2018 10:30 - 18 minutes - 25.9 MB2018: 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
December 04, 2018 09:40 - 14 minutes - 20.3 MBHow to start scrappy in a regulated industry blog post With Jack
Post-launch problems revisited
November 29, 2018 11:30 - 12 minutes - 16.9 MBPost-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
November 08, 2018 14:00 - 17 minutes - 23.8 MBThe 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
September 07, 2018 09:40 - 9 minutes - 13.5 MBNavigating a funk as a solo founder With Jack Epicurrence Tweet about momentum Tweet about being in a funk
Why I quit wedding photography
August 23, 2018 12:35 - 7 minutes - 10.9 MBWhy I quit wedding photography With Jack My photography
Positioning your product to a tiny audience
June 11, 2018 13:30 - 17 minutes - 31.3 MBPositioning 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)
Start talking about your idea
May 17, 2018 12:30 - 21 minutes - 39.2 MBStart talking about your idea With Jack Idea to Execution and Beyond Masters of Scale—How to price your product to scale
My journey to 250 customers
May 08, 2018 10:45 - 15 minutes - 14.4 MBNotist My journey to 250 customers
The 'why' behind building With Jack
April 17, 2018 15:20 - 18 minutes - 16.9 MBThe 'Why' Behind Building With Jack blog post My YouTube channel Everybody's Winging It by Baremetrics Toad's Caravan
How I improved With Jack's sign-up rate by 14%
March 22, 2018 14:00 - 11 minutes - 10.4 MBAll Day Hey! Improving With Jack's Sign-Up Rate By 14% Naomi Atkinson Design Scott Riley
Minimum viable process
March 14, 2018 17:00 - 18 minutes - 16.6 MBLinks 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