28 episodes

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

Bootstrapped Digest with Ashley Baxter Ashley Baxter

    • Business
    • 5.0 • 2 Ratings

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

    Do things that don't scale

    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
    "This is so much bigger than me"

    "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.

    • 12 min
    The road to automating my business

    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.

    • 14 min
    Product-market fit struggles

    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.

    • 15 min
    This is not a year in review

    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.

    • 21 min
    My mid-Year review

    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?

    • 14 min

Customer Reviews

5.0 out of 5
2 Ratings

2 Ratings

Top Podcasts In Business

Money Stuff: The Podcast
Bloomberg
REAL AF with Andy Frisella
Andy Frisella #100to0
Money Rehab with Nicole Lapin
Money News Network
The Ramsey Show
Ramsey Network
Leading Up With Udemy
Udemy
The Money Mondays
Dan Fleyshman