The AOA Leadership Newsletter Hi Reader, I had a client ask me this question recently: “When entrepreneurs are going through massive personal transformation, how do they integrate that with the intensity of running a startup?” Here’s what I told him: If you can’t handle transformation on the inside, you won’t be able to handle it on the outside. Every external breakthrough in a company requires a nervous system strong enough to hold the chaos and change it creates. Without that foundation,...
8 days ago • 2 min read
Note: Scroll down to check out our new section How to Have Better Meetings. The AOA Leadership Newsletter Hi Reader, I've seen this pattern in several of my CEO clients: They feel superior as a way to protect themselves. But in actuality, they're signaling their shame and shutting down their joy. Here’s what I show them to break the pattern: 1 - Superiority and deep joy are fundamentally incompatible. Try to name a single person who feels superior that is also deeply joyful. You won’t find...
29 days ago • 2 min read
Note: Scroll down to check out our new section How to Have Better Meetings. The AOA Leadership Newsletter Hi Reader, A while back, I worked with a CEO who was brilliant, relentless, and exacting. His startup was breaking into its first $10M year. But every time they got momentum, something bottlenecked. Engineering wouldn’t ship on time. Sales didn’t close fast enough. Leadership hires weren’t stepping up. The problem? He had an answer for everything. In meetings, he’d jump in before the head...
about 1 month ago • 2 min read
Note: We’re always looking for ways to add more value to these newsletters, so we’re introducing a new section: How to Have Better Meetings. Scroll down to check it out! The AOA Leadership Newsletter Hi Reader, Last month, I worked with a founder who had just closed a Series B. To the outside world, he looked like a rocket ship. But inside, he was hollowing out. He told me he couldn’t shake the pressure that it was all on his shoulders. He’d stopped sleeping. He had to keep pushing. His...
2 months ago • 2 min read
The AOA Leadership Newsletter Hi Reader, Hi there, Last spring I worked with a COO who prided herself on being “low-maintenance.” Twelve-hour days, skipped lunches, and redeye flights—whatever the company needed, she delivered. Unsurprisingly, she was on the verge of burnout, and even then she felt that she had to maintain a strong front for her team. Yet her exhaustion was palpable, and the team was mirroring that energy. Productivity was down, and morale was low. In a coaching session, I...
2 months ago • 2 min read
The AOA Leadership Newsletter Hi Reader, In 2009, a small team of neuroscientists set out to answer a question—can you really smell fear? They began with two very different afternoons and a stack of cotton pads. Afternoon #1Twenty volunteers ran hard on treadmills until their pulses raced. Researchers blotted the sweat from each runner’s underarms, sealed every pad in glass, and tucked the jars on ice. Afternoon #2Then, those same volunteers suited up for their first skydives. As the plane...
3 months ago • 2 min read
The AOA Leadership Newsletter Hi Reader, A few years ago, I coached the founder of a 300-person health-tech firm. Brilliant product sense, generous heart—yet his team was constantly missing deadlines due to second-guessing. One afternoon, while white-boarding priorities, I asked him to narrate his thoughts out loud. What poured out was a stream of quiet self-doubt: “This plan is probably naïve.” “Marketing will poke holes in this—maybe they’re right.” “I’m not sure I’m the guy to lead the...
3 months ago • 2 min read
The AOA Leadership Newsletter Hi Reader, For a long time, I’ve been a student of the many ways humans make sense of life—psychology, spirituality, neuroscience, and beyond. Among the most fascinating to me are the ancient medical systems of Traditional Chinese Medicine and Ayurveda. In those systems, there’s a core principle that feels increasingly relevant to how I see companies: When something is imbalanced in a living system, you can see it everywhere. Take the liver, for instance: In TCM,...
5 months ago • 2 min read
The AOA Leadership Newsletter Hi Reader, When I was working as a VC, I found myself in the midst of a fundraising process that I wasn't particularly enjoying. It felt mechanical and draining - a necessary evil rather than something meaningful. So I thought, “Okay, how do I really enjoy this process?” And I asked myself, “What are the things that I enjoy? I wrote down: I enjoy learning. I enjoy going deep with people. I enjoy strategy. Then, I also realized that everybody I was fundraising...
6 months ago • 1 min read
The AOA Leadership Newsletter Hi Reader, One day, while sifting through our company emails, I noticed a pattern — there was an endless amount of faffing going on. You know the kind: One person would float an idea, someone else would chime in with an enthusiastic "Oh, good idea!" A third would add their thoughts, and the thread would grow longer. But beneath all this apparent engagement, nobody was actually committing to anything. Ideas hung in the air, and no one was moving things forward....
7 months ago • 2 min read
