His $5 App Made $1M. Now He’s Building With AI | Sean Heiney | Ep. 1

Sean Heiney, founder and product builder, shares how a $5 AOL Instant Messenger add-on made over $1 million in sales, how AOL threatened to sue and then bought it, and how he's using AI agents to build new startup products today. Topics: startup founder interview, building products with AI, AI agents, SignalWire, Barracuda Networks, product management, software startups. In this founder podcast episode, I sit down with Sean to talk about that story, his years building products at Barracuda Networks through its IPO, co-founding SignalWire, and what he's experimenting with now. Sean is using AI agents to work on multiple product ideas, including video conferencing and open-source security tools. We talk about what AI makes easier, what still takes judgment, and why he believes software alone is no longer a moat. In this conversation: • How a small improvement to AOL Instant Messenger became a paying business • Competing with expensive products by making yours simpler and cheaper • Building products at Barracuda and staying through its IPO • Co-founding SignalWire and the AI infrastructure idea that didn't work out • Using AI agents to build and test multiple ideas • Why customer feedback matters more than falling in love with your vision Sean is candid about what worked, what didn't, and what he still hasn't figured out. I'm Naveen Chandupatla, a software engineer and founder. This is Episode 1 of my conversations with people building companies, figuring things out, and sharing what they learn along the way. Find Sean and his projects: https://sean.net Subscribe for more conversations with founders and builders.