Over the past few weeks, I’ve had the chance to mentor several early-stage fintech founders—some still at idea stage, some with a rough prototype, all incredibly passionate. These conversations stirred up a lot of memories from my own early days as a founder: the scrappiness, the uncertainty, the optimism (and delusion), and the invisible walls you only discover once you run straight into them. This is not advice from someone claiming to have it all figured out. This is more of a conversation I wish someone had with me years ago—before I burned time, money, and energy learning these the…
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It was 3AM in December when my phone rang. A smoke alarm had gone off in one of my units. No smoke, no fire—but the guests were scared. Outside, Boston was buried in snow. Still, I threw on a jacket and went. Not to silence an alarm. To show up. To reassure. To calm an scared customer. To show that we are on top of everything. And also—to make sure everything really was okay. Because when you’re the one running the business, you’re not just calming guests. You’re also protecting the thing you’ve built. Sometimes, it’s about empathy.Sometimes, it’s about…