Not Another CEO Podcast | Learning from Setbacks - Anthony Corletti - Casa

Learning from Setbacks - Anthony Corletti - Casa - Episode #41

April 29, 2025 / 49:36/E41

What happens when passion, persistence, and curiosity meet the brutal realities of startup life? In this Failing Forward edition of Not Another CEO Podcast, Nick Freund sits down with Anthony Corletti, a seasoned technical founder and former CEO of Casa, to unpack his entrepreneurial journey.

Anthony shares hard-won lessons from building, and ultimately shutting down, his company, discusses frameworks like the "Founder’s Care-o-Meter" and the "Personal Board of Advisors," and reflects on how founding has shaped his broader life perspective.

Takeaways:

The Spark for Entrepreneurship: Anthony shares how working closely with rideshare drivers during his early startup days ignited his passion for solving real-world problems through tech, and how the immediacy of feedback fueled his love for early-stage building.
What Drives a Technical Founder: For Anthony, the excitement lies in scaling impact, solving one user's problem in a way that could eventually benefit thousands. His love of learning and "always day one" mindset continues to push him forward.
The Lightbulb Moment for Casa: A podcast analogy about how context transforms perception inspired Anthony to rethink how engineering workspaces could better integrate product and design teams, leading to the idea behind Casa.
Introducing the Founder’s Care-o-Meter: Anthony explains the framework he created to check his conviction at different stages of building Casa. He tracked whether he still felt a "hell yes" about the mission and scored his emotional connection to the problem versus the solution every six weeks.
Building a Personal Board of Advisors: Anthony stresses the importance of surrounding yourself with trusted confidants, from family to expert mentors, who can offer honest feedback, accountability, and different perspectives throughout the founder journey.
Knowing When to Shut Down: Anthony candidly describes how feedback from pilot customers, competitive insights, and introspection via the Care-o-Meter helped him make the difficult but clear-eyed decision to wind down Casa.
Founding and Life Philosophy: Anthony reflects on how founding has shaped his view of service, resilience, and embracing life's unexpected opportunities. His future focus is simple: prioritize the people you work with and the problems you solve.

Quote of the Show:

" Experience is what you get when maybe you didn't get what you wanted… being able to share that with [future founders] is such a critical point, and it's super important." - Anthony Corletti

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