A founder-focused discussion on what it took to get RightMessage through a plateau. Brennan talks about product changes, repositioning, what stalled growth, and the operational lessons involved in turning the business back around.
Related resources
A long-form Baremetrics founder chat that mixes Brennan’s backstory with product and pricing strategy. The discussion covers personalization, getting early customers, agency work versus software, info products, and how Brennan thought about building and monetizing SaaS.
This one focuses on the jump from content creator to SaaS founder. Brennan talks about audience segmentation, website personalization, target-market fit, and the ways creator skills like copywriting and lead nurturing translate into bootstrapping a software company.
A return appearance on thoughtbot’s Giant Robots podcast. Brennan talks about the shift from contractor to company-of-one, why a bigger business is not automatically a better one, and how he uses AI while keeping the setup intentionally lean. The conversation also revisits how RightMessage works and how his thinking has changed since his 2012 appearance.
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