Angel
Basecamp

In this panel, experienced investors and newcomers shared the mic to discuss their different paths into investing. The conversation touched on tried-and-true strategies, while newer voices brought fresh energy and unconventional thinking. The discussion revealed that there are multiple ways to participate and go about angel investing. It isn’t about age or years in the game, but rather it’s about curiosity, courage, and learning from both wins and losses. The title of "Rainmaker" is earned through insight, grit, and reflection.

Experienced angel investor Daren Cotter pulled back the curtain on building an early-stage portfolio. His talk was a practical, grounded look at how to think strategically as an angel investor. He spoke about the necessity of diversification. Daren emphasized building a portfolio that spreads risk and increases the odds of success over time. One of his most powerful tools? A single, guiding question, “If everything goes right, can this be a big company?” This simple yet profound question forces investors to consider not just potential, but scale and ambition. Daren’s thoughtful approach highlighted the importance of clarity, realism, and long-term thinking in early-stage investing.

This panel tackled the often-overlooked challenge of knowing when and how to exit. From methodical planning to instinctive risk-taking, founders and investors alike shared stories of stepping away at just the right or sometimes wrong moment. Whether through mergers, acquisitions, or founder transitions, each story offered a window into the high-stakes decisions that come with growth. The key lesson: exits are as strategic as entries, and every path requires foresight and flexibility.