From Where I’m Sitting
Notes from real conversations, as they’re happening
Most weeks, I find myself in a handful of interesting conversations with founders who are in that messy stage of growing their businesses - things are working, but not as easily as they would like.
The challenges I hear, the solutions we talk through - so much of it comes up over and over again. So I started sharing a few of those moments, in case there’s something useful in there for others on the journey.
I send them out every so often. If you’d like them in your inbox, drop me your details below.
Conversations I’m In
Most founders building out their team look for the same thing: someone versatile. Someone who can flex, hold a lot, fill the gaps. But versatility isn't the same as clarity - and a role that's asking for too much usually isn't solved by finding a better person for it.
After years of building businesses, growing teams, and sitting alongside founders as they navigate the messy middle between where they are and where they want to be, I find myself coming back to the same three areas again and again.
Why smart teams with different perspectives don’t always land on clear decisions (and what actually helps)
Why traditional hiring signals aren’t telling you what you actually need to know anymore
Why this stage of growth isn’t about fixing what’s broken - it’s about noticing what’s no longer a fit