A transparent account of bootstrapping an insurance business as a solo founder.
With Jack I am Ashley Paul Graham's essay, do things that don't scaleBởi Ashley Baxter
With Jack I am AshleyBởi Ashley Baxter
With Jack I am AshleyBởi Ashley Baxter
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 breakdownBởi Ashley Baxter
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 TwitterBởi Ashley Baxter
Mid year review blog post Reflecting on a disappointing product launch SuperHi Scott, the freelancer I work with Follow me on TwitterBởi Ashley Baxter
With Jack Why can't I celebrate tiny wins blog postBởi Ashley Baxter
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Bootstrapped Digest with Ashley Baxter


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Mistakes I made when choosing a market
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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 fishingBởi Ashley Baxter
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Bootstrapped Digest with Ashley Baxter


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Reflecting on a disappointing product launch
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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 launchedBởi Ashley Baxter
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Bootstrapped Digest with Ashley Baxter


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The challenges of building an insurance business
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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 businessBởi Ashley Baxter
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Bootstrapped Digest with Ashley Baxter


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Lessons learned from inheriting the family business
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Before UpFront The family business With JackBởi Ashley Baxter
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Bootstrapped Digest with Ashley Baxter


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Should you build a product for a user segment you're not a part of?
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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 TwitterBởi Ashley Baxter
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Bootstrapped Digest with Ashley Baxter


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How has the rebrand performed 4 months on?
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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!Bởi Ashley Baxter
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-winBởi Ashley Baxter
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Bootstrapped Digest with Ashley Baxter


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In the trench tips for figuring out what problem you solve
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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 TwitterBởi Ashley Baxter
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 DubrovnikBởi Ashley Baxter
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Bootstrapped Digest with Ashley Baxter


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How to start scrappy in a regulated industry
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How to start scrappy in a regulated industry blog post With JackBởi Ashley Baxter
Post-launch problems revisited blog post Navigating a funk as a solo founder blog post With JackBởi Ashley Baxter
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Bootstrapped Digest with Ashley Baxter


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The process and reasons behind With Jack's rebrand
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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 websiteBởi Ashley Baxter
Navigating a funk as a solo founder With Jack Epicurrence Tweet about momentum Tweet about being in a funkBởi Ashley Baxter
Why I quit wedding photography With Jack My photographyBởi Ashley Baxter
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Bootstrapped Digest with Ashley Baxter


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Positioning your product to a tiny audience
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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)Bởi Ashley Baxter
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Bootstrapped Digest with Ashley Baxter


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Bootstrapping Niice to 100,000 users
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Niice Chris on TwitterBởi Ashley Baxter
Start talking about your idea With Jack Idea to Execution and Beyond Masters of Scale—How to price your product to scaleBởi Ashley Baxter
Notist My journey to 250 customersBởi Ashley Baxter
The 'Why' Behind Building With Jack blog post My YouTube channel Everybody's Winging It by Baremetrics Toad's CaravanBởi Ashley Baxter
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Bootstrapped Digest with Ashley Baxter


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How I improved With Jack's sign-up rate by 14%
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All Day Hey! Improving With Jack's Sign-Up Rate By 14% Naomi Atkinson Design Scott RileyBởi Ashley Baxter
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 IterateBởi Ashley Baxter