Ed speaks with Tyler Denk, the founder and CEO of Beehiiv, a newsletter platform. They discuss Tyler’s background at Morning Brew, his thoughts on selling secondary shares, and dealing with personal loss while running a company.

Ed speaks with Caroline Spiegel, founder and CEO of Quinn, an app for listening to audio erotica. They discuss what differentiates her company from existing adult content sites like Pornhub and OnlyFans, what it’s like to raise money for a company that VCs might not take seriously, and how to get over embarrassment as a founder.

Ed speaks with Gabe Stengel, Co-founder and CEO of Rogo, about the potential for AI to disrupt the banking sector. They also discuss Gabe’s experience pitching his financial services AI company to VCs, the importance of willpower, and how he finds balance between work and his personal life.