In this podcast episode, Matt Meeker shares his entrepreneurial journey, detailing the financial hurdles he faced with Bark and the key moments that shaped his career. He discusses the creation and growth of both Meetup and BarkBox, highlighting significant experiences like how the Howard Dean campaign fueled Meetup's expansion and the frustrations that inspired BarkBox's launch. As Matt reflects on the challenges of securing funding and managing rapid growth, he also talks about crucial decisions, including stepping down as CEO and later returning to guide the company back to profitability. Throughout the conversation, he emphasizes the delicate balance between hard work and luck in achieving success.