Bootstrapped Digest with Ashley Baxter: Recent Episodes

Ashley Baxter

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

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

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  • With Jack
  • I am Ashley

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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.

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  • 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

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  • 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

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

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

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  • 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

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  • 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

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  • 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

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  • Before UpFront
  • The family business
  • With Jack

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  • 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

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

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  • 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

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  • 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

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  • 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

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

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

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

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

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  • Why I quit wedding photography
  • With Jack
  • My photography

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  • 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)

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  • Niice
  • Chris on Twitter

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  • Start talking about your idea
  • With Jack
  • Idea to Execution and Beyond
  • Masters of Scale—How to price your product to scale

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  • Notist
  • My journey to 250 customers

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  • The 'Why' Behind Building With Jack blog post
  • My YouTube channel
  • Everybody's Winging It by Baremetrics
  • Toad's Caravan

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  • All Day Hey!
  • Improving With Jack's Sign-Up Rate By 14%
  • Naomi Atkinson Design
  • Scott Riley

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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