A Crooked Compass Beats a Perfect Plan | The Entrepreneurial Journey

Lisa Pagotto has every reason to have quit. She sold her house to start Crooked Compass. Made it onto Shark Tank. Watched her business take off. Then one signature that never came nearly destroyed everything she’d built. Most people would have walked away. Lisa didn’t. In this conversation, Dave sits down with the Founder & CEO of Crooked Compass to hear one of the wildest entrepreneurial stories we’ve had on the show. From an investor deal falling apart at the last possible second, to a stranger stepping in with a life-changing act of generosity, to rebuilding an international travel company during a global pandemic, Lisa’s journey is full of moments that forced her to choose between giving up and figuring it out. The conversation also dives into the mindset that’s helped her keep moving through every setback. Lisa shares the FIRE Framework she now teaches to leaders around the world, why integrity matters even when it costs you, how rest can actually make you a better entrepreneur, and why waiting for certainty is usually the fastest way to stay stuck. Of course, you’ll also hear about the incredible experiences Crooked Compass creates, taking travelers far beyond the usual tourist stops and into some of the most fascinating places on Earth. Whether you’re building a business, navigating a setback, or wondering if it’s time to make that call you’ve been putting off, this episode is a reminder that the next opportunity rarely looks the way you expect it to.