I don’t want this to be a traditional year in review, but I do want to document what it was like bootstrapping my business through a pandemic. 2020 turned out to be the most testing and lonely experience I’ve faced as a solo founder.

2019 was all about blocking out big chunks of my calendar to prepare my coverholder application for my binder. We’re heading in the right direction and have started 2020 by kicking off the development of the quote and bind system

According to the year progress account on Twitter, 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.

I first heard this term on Justin Jackson’s blog. I’m not 100% sure if I’ve understood it correctly, but my interpretation is that company/founder fit is ensuring the business you build fits the kind of life you want to live.

Two things stand out to me about 2018: the progress I’ve made on With Jack and the trips I’ve taken. Although the first 6 months were fairly uneventful, it ended up being a great year for business and travel.