Bootstrapped Digest with Ashley Baxter episodes:

• March 24, 2026Migrating ~ 1,400 customers to a new system without chaos. Here’s my plan

  • The road to automating my business
  • Vicky Gu

  ...more

  

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• March 10, 2026It's just a giant calculator

  • My new system - tell your freelance friends?
  • The startups for the rest of us episode I was on

  ...more

  

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• August 15, 2022Do things that don't scale

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

  ...more

  

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• July 18, 2022"This is so much bigger than me"

  • With Jack
  • I am Ashley

  ...more

  

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• July 04, 2022The road to automating my business

  • With Jack
  • I am Ashley

  ...more

  

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• February 15, 2021Product-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

  ...more

  

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• January 26, 2021This 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

  ...more

  

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• July 26, 2019My 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

  ...more

  

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• June 28, 2019Why can't I celebrate tiny wins?

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

  ...more

  

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• June 19, 2019Mistakes 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

  ...more

  

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