Episode Details

When it comes to fundraising, the stakes are high. You're not just selling an idea; you're inviting investors to believe in your vision, your team, and your ability to deliver results. But as serial entrepreneur, investor, and advisor Aaron Schwartz shared on our newest episode of Unfinished Business, perhaps the secret to mastering the art of pitching lies in another equally tricky endeavor — dating.

Welcome to Unfinished Business, the podcast where we dig into the whys, hows, and WTFs of building and thriving in business — hosted by longtime founder friends Alex Schinasi and Lee Rotenberg. Every week, we’ll invite industry leaders and fellow entrepreneurs to candidly share their wins, truths, and lessons (and laugh while doing it).

If you look close enough, finding investors can feel oddly familiar to finding a life partner. There’s the thrill of the pitch, the nerves of a first meeting — the ever-so-delicate “will we or won’t we” dance of it all. You’re at once vetting each other, feeling out your competition, and trying to channel your most authentic self.

It’s exhausting and confusing — so consider this guide to pitch clarity. With real-world stories, humor, and a heavy dose of hindsight, we walk through Aaron’s top strategies for securing a successful round — from nailing the first impression to knowing when to walk away. Take notes, pay close attention, then go seal your next deal.