Entrepreneurship can feel like a lonely grind, but it doesn’t have to be. Dave Parker, the CEO of the Entrepreneurs’ Organization, knows firsthand what it takes to build, scale, and sometimes close a business. In this episode, he joins Alex Raymond to share what separates successful founders from those who get stuck—breaking down product-market fit, the power of timing, and why self-awareness matters more than most people think.

A key takeaway? Forum, EO’s peer-driven support system, offers entrepreneurs a space to be real about the highs and lows without the noise of unsolicited advice. Dave opens up about his own mental health journey and why having the right people around you can make or break your ability to keep going. He also challenges the idea of failing fast, arguing that knowing when to walk away is just as important as knowing when to push through.

For founders navigating uncertainty, this episode is a reminder that resilience isn’t just about grinding harder, but about making better decisions, leaning on the right community, and staying clear-eyed about what actually works.