Brian Casel

Brian Casel


Brian Casel is a veteran of the bootstrapping game, having left his full-time job back in 2008. You might have heard him on the Boostrapped Web podcast where he shares his journey starting and building software products. Over the years Brian has pretty much done it all, built software businesses, courses, productized services and even sold some along the way. Most recently, Brian has been working on ZipMessage, a new way to communicate asynchronously.

Talking points

On ZipMessage

  • Where did the idea come from? Have you worked on async products before?
    • ideation, validation - all things founders struggle with
    • when do you know it's "right"
  • Why is async work becoming more popular? How can you use ZipMessage to do this?
  • How's it been going in terms of growth, finding PMF and users?

On funding from Calm

  • Funding for bootstrappers has become more accessible over the past few years, however some still want to self-fund for as long as possible. You've been self-funding your ventures for a while, why did you decide it's time to raise for ZM now?
    • What made the calm terms more favourable?
  • How are you planning to deploy the capital?

On Productized Services

  • You spent a fair portion of time creating a productized service (Audience Ops), then a course and a podcast (Productize and Scale). I know this isn't your focus now, but I'm interested for those who want to take their step out of freelancing to productizing, how should they go about doing it?
    • More context → I tried this for podcast editing. It worked somewhat, but people kept asking me for custom work and I never outsourced anything... ended up just being slightly more structured freelancing.

On music

  • Brian, we've spoken before about your passion for music. You're in a position where you could choose to go down a route / start a company that provides you a sustainable living doing what you love - why haven't you pursued anything here?
  • Should people monetise their hobbies? Or should they stay as hobbies?


  • Book
  • Podcast
  • Indie Hacker

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