In this episode, we tell the (painful, funny, and way-too-relatable) story of how we tried to invest in Arc Browser — and got told “no” multiple times. We’re not talking about losing money angel investing. We’re talking about the weird scenario where you want to give a startup your money because you’re genuinely obsessed with the product… and they won’t take it. We walk through how we found Arc after years of trying every “productivity browser” and tab/workspace solution (including Workona), why Arc’s onboarding felt like actual movie-trailer-level craftsmanship, and the moment it clicked that this was what we hoped ChromeOS would become. Then we get into the receipts: the DMs, the LinkedIn/Twitter messages, the “I’m going to continually message you” follow-up, and the 4,400-word conviction article we wrote just to get on Josh Miller’s radar. When he finally asked, “What’s the largest check you could write?”, we realized this wasn’t just fanboy energy — we had to show real intent. The takeaway: when a product feels like magic and you can convert both non-technical and deeply technical “Chrome forever” people, that’s a signal. But cap tables are intentional, and sometimes the best you can do is play the long game, support loudly, and earn trust over time.