• Entrepreneurship - Hospitality - Ideas

    Be the Boss Who Still Shows Up at 3AM

    April 23, 2025 - By 

    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…

  • Ideas

    I Almost Bought a SaaS Company (And I’m Glad I Didn’t)

    March 25, 2025 - By 

    Late last year, a warm lead slid into my inbox—a SaaS company in HR tech. I knew next to nothing about HR tech. But I know SaaS. I know tech. And I’ve always had a thing for buying a business. In my day-to-day, I’m constantly making investment decisions—whether I’m identifying the next property for my co-living business, COZi Home, or running the numbers for the new product for “Mommy Goes to Work“. Over time, I’ve developed a solid investment instinct—data-backed, gut-checked, and battle-tested. And here’s one truth I’ve learned: The juiciest opportunities often hide in the boring, dusty corners no…