Insights on Building Mission-Driven Organizations
Practical lessons from 15+ years of leadership across nonprofits, real estate, and healthtech. Topics include AI implementation, nonprofit operations, business systems, and what it takes to scale organizations without losing your mission.
Collapsing the Skill Stack: How AI Turned a 10-Person Team Into One Operator
For most of the last 30 years, building anything meaningful required stitching together specialists. You needed a writer, a designer, a developer, a marketer, an ops person, a data analyst, a customer support lead, and usually a project manager to hold it all together. The work was not actually that complicated, but the coordination was. The bottleneck was never intelligence. It was friction.
AI removed that friction.
Listening to Your Emails and Messages Makes You a Better Communicator
For most of my career, I’ve moved fast. I’ve relied on instinct, momentum, and the ability to figure things out on the fly. In small teams or early-stage environments, that approach works. You don’t have to explain every step or provide perfect clarity—you just build, adjust, and keep going. But as the organizations around me grew, the cost of unclear communication started to show up in ways I couldn’t ignore. I’d send a message that made perfect sense in my head, only to realize later it didn’t land the way I intended. Or I’d fire something off quickly and it would accidentally create more work or confusion for someone else. That’s when I started using a small Mac feature that unexpectedly became one of the most effective productivity habits I’ve ever built: Speak Selection.
Why I Stopped Chasing Inbox Zero (and What I Do Instead)
For a long time, I thought Inbox Zero was the goal.
If my inbox was empty, I felt clear. In control. Productive. Like I had actually finished something.
But eventually I noticed the pattern. The cleaner my inbox got, the busier my days felt. More replying. More sorting. More “just one more thing.” I wasn’t doing better work. I was just better at moving emails around.
My Supercharged Email Management Strategy
Managing multiple email inboxes has become all too real in 2019. Personal email, school email, work email, your project, your other project. For years, the Gmail app was my go-to. Flipping between inboxes seemed like the best there ever could be. The thought of a native app with multiple logged-in email accounts plus efficiency?
Productivity Apps that distract me all day long
An ever-growing list of apps and platforms I use every day in my Chief Operating Officer role at Stupid Cancer, client work, and blogging.