A few weeks ago, I spent 3 days in Scotts Valley for the annual Village Global leadership retreat for founders. Here's why I thought it was one of the most high-functioning off-sites I've ever been a part of:
A caveat was set at the beginning of the week to avoid the common pitfall of most founders at similar events, which was to be vulnerable instead of to posture. This is something that I'd guess won't be as talked about as a post-event highlight, but should be.
Personally, I find this to be one of biggest issues with founder-focused events. All founders are struggling, regardless if you're a pre-seed or a Series B founder. The biological default, which we all fall victim to at some point, is to try to deflect on all the real, very painful things you're dealing with and only talk about all the things that are going right. But, I find reality is often the inverse of most founder talking points. Because the vulnerability caveat was set early and it was an off-the-record discussion all week, I had the most real conversations with founders I've ever had. I rarely come out of an event saying this.
The quality of the guests and speakers was arguably the biggest highlight of the week. We heard from Diana on how to create positive self-talk as a founder and Lukas on some of the biggest things he's seeing with large enterprise deployments of AI. I also had the pleasure of attending a small breakout to learn from Mamoon on how to think about constructing a healthy fundraise. These are heavy-weights of the industry today and we got all of the content in small circles, curated and bundled, in a few days.
It was an insanely well-planned week. The level of detail was extremely impressive. Flying 60+ (very particular) founders from around the country into a single location for 3 days is a planning nightmare. Shiela and the team had every hour, both on and off times, scheduled. The facility/food was incredible, meals were moderated within curated groups and there was an underlying focus on health/fitness throughout the week.
We had access to cold-plunges, a great gym and organized hikes. Despite being away from our routines, we were able to still be locked in on the things we care about.
Overall, Sheila and team crushed it.
Very appreciative of Anne, Ben and the entire VG network.
CC: Stu, Christopher, Diego, Luke, Jacob, Aman, Siamak, Aaron, Aaron, Françoise, Allie.
