Playing Offense: Reflections on Seven Years of Running a Startup | Ep 3

In this introspective third episode, your hosts Caleb, David, and Matthew dive deep into the heart of startup culture—through the lens of personal habit. We pull back the curtain on the actual practices that propelled our software company from a bootstrapped startup to a successful exit.

But it’s not all about the victories. We get candid about the habits that served us well and the ones we wished we'd left behind. Join us as we dissect the daily disciplines that shaped our journey and the missteps that taught us invaluable lessons.

In This Episode, You’ll Discover:

• The essential habits that helped us stay on track during our most intense periods of growth.
• How certain unexpected habits, which we initially underestimated, turned into our secret weapons.
• Personal anecdotes from Matthew, Caleb, and David—what we did, what we didn’t, and what we learned along the way.

This isn’t just about our story—it's a roadmap and a cautionary tale for all current and aspiring entrepreneurs. Tune in to glean wisdom from our experience and maybe even spot the habits you need to adopt or avoid as you start your journey.

Whether you're knee-deep in the trenches of building your business or you’re simply fascinated by the intersection of personal habits and professional success, this episode is for you. Sit back, relax, and let’s break down the building blocks of a successful startup, one habit at a time.

Learn more at stackinghabits.com or follow our habit adventures on Instagram.