What’s Working and What Isn’t
In my launch note I cautioned that Cortlandt will remain a work in progress by design. As such, it’s important to continually assess what’s working and what isn’t. We’re still in the earliest of innings, and don’t have a meaningful number of data points yet, but I’d like to give you an early report on the things that I’m excited about and where I’m going to strive to make improvements.
What’s definitely working are the individual conversations that I am having with many of you, plugging members together on deals, opportunities, jobs, subject matter expertise etc. In the last week I’ve had calls connecting members with members on two opportunities that are north of $500mm, and one deal that is potentially in the billions. I’ve had discussions and made introductions concerning SPACs, insurance expertise, a real estate opportunity, the lift out of a non-core asset from a large financial institution, a potential COO opportunity, and three different angel investments. I think of these conversations as being ‘one to many’, meaning that I’m talking to many of you. What Cortlandt is supposed to be about is the ‘many to many’: how each of you connect directly with each other as trusted collaborators. Improving this dynamic is something I’m very focused on.
One way I hope to foster more interpersonal relationships within Cortlandt is through more in person get-togethers. These are definitely working. In the past two weeks I have hosted a larger Cortlandt dinner and a more intimate lunch. The conversations at each event were intelligent, engaging, and though nothing actionable arose from either, in debriefing with participants it was obvious that seeds had been planted for future conversations.
What hasn’t worked as expected (at least in my eyes) is the two Switchboard calls we’ve held. These were the cornerstone of Cortlandt and I hope they will continue to be in the future. I could shrug them off, dismissing the first one for a new format that failed, and the second for my being not quite ready to return to work, but I think there is a larger dynamic at play around the appetite for, and attitude towards, virtual gatherings in the ‘new normal’. We’re going to be giving a lot of thought to this before our next Switchboard.
