Bootstrapped Digest with Ashley Baxter

Ashley Baxter
  • 5.0 (2)
  • MARKETING
Bootstrapped Digest with Ashley Baxter

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

  1. 08/15/2022

    Do things that don't scale

    In Paul Graham’s essay, do things that don’t scale, he talks about you acting as the software, doing things manually that you plan to automate later. Currently I’m the software. I process quotes, renewals, cancellations and everything in between. The automated quote and bind system is in development, but there are so many benefits of doing things that don’t scale. Let's talk about them.

    12 min

  2. 07/18/2022

    "This is so much bigger than me"

    Following on from the last episode where I talked about why now is the right time to automate the business, in this episode I go into more detail about what’s required to do that. To date this has been a 2.5 year process and it hasn't been without its bumps in the road. I think I'm the first one-person business to go through this process and I feel so overwhelmed.

    13 min

  3. 07/04/2022

    The road to automating my business

    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.

    15 min

  4. 02/15/2021

    Product-market fit struggles

    Despite being 4 years into building With Jack I'm not convinced I have product-market fit. Everyone has a different definition of what PMF is, so I go through some of the popular definitions and talk about how With Jack measures up.

    16 min

  5. 01/26/2021

    This is not a year in review

    I'm back with a long overdue update! In this episode I document what it was like bootstrapping my business through a pandemic as a solo founder. I share the challenges of the past year and the lessons I learned. We're still not out of the woods yet, but I now feel ready to talk about the impact the pandemic has had on my business.

    22 min

  6. 07/26/2019

    My mid-Year review

    We're 55% of the way through 2019! Coupled with the start of summer being quieter for my business, now seems a good time to revisit some of the goals I set myself and do a mid-year review. How am I doing? Am I on my way to achieving them, have they evolved into something new, or have I shelved them completely?

    15 min

  7. 06/28/2019

    Why can't I celebrate tiny wins?

    Last week With Jack hit a huge milestone. Despite this being something I have been working towards for so long, I didn’t feel anything when it happened. My friends said I was in shock. Over a week has passed and I’ve had plenty of time to let this achievement sink in. In this episode I talk about why I’m finding it difficult to celebrate my tiny wins.

    13 min

  8. 06/19/2019

    Mistakes I made when choosing a market

    Before starting my business I hadn’t given much thought to what goes into choosing a good market. I love targeting freelancers, but that doesn’t mean I’ve chosen an ideal market to sell to and I want to share some of the factors I wish I’d considered beforehand. If you’re starting a business you will want to consider these factors, too.

    18 min
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2 Ratings

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

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