Great Pitch, Wrong Room
Tuesday, October 20, 2026, 10:00 AM PDT – 12:00 PM PDT
Downtown Works - Coworking Office Space Mission Valley · 3517 Camino del Rio S Suite 215, San Diego, CA 92108, USA
Hosted by Natalia Corona
An official IDEA Week San Diego event, presented by Frictionless in collaboration with Connect, co-hosted with Downtown Works There is a strange pattern in how founders pitch. Put them in front of an investor and they talk about the product. Put them in front of a client and suddenly they are talking about the business. Both times they are answering a question nobody asked, and both times they walk out of the room wondering what went wrong. On October 20, as part of IDEA Week San Diego, we are going to watch it happen live and then take it apart. One company gets pitched on stage, cold. Sitting in the front row are two people who hear pitches for a living and who want completely different things out of the same nine minutes. An investor, to be announced soon, is deciding whether they would fund it. Hillary Applin is deciding whether she would buy it. They will stop the pitch where it worked, stop it where it lost them, and show you the version that would have landed in both rooms. Hillary spent more than 15 years building and scaling revenue organizations across AI, SaaS and enterprise technology before founding Pype, where she is now CEO. She has sat on the other side of the table from countless companies trying to sell to her, and she can tell you in about thirty seconds why most of them lost her. Our investor seat will be announced soon. Between them they will walk through the ten moments where a pitch wins or loses both rooms: your opening, the problem, the product, your numbers, competitors, your team, hard questions, price, vision and the ask. Then it is your turn. In the second half, the floor opens up and you can put your own pitch in front of both of them, in front of everyone, and find out what each of them actually heard. This session is part of IDEA Week San Diego, Connect's weeklong celebration of the founders, investors, researchers and creators shaping what's next for the region, running October 19 to 23. Connect has spent more than 40 years helping build San Diego's innovation economy, and we are proud to bring Great Pitch, Wrong Room into the week with them. Moderated by Mario Corona, Co-Founder of Frictionless. Co-hosted with our venue partner Downtown Works at their Mission Valley location. Tuesday, October 20 at 10:00 AM. Free to attend, and the room fills fast.