Improving VC to VC Meetings

It used to be that I stayed in sync with other investors in the venture market over coffees, walks or meals. Meetings were longer and more organic, if less frequent or prescriptively scheduled. Who I spent time with was largely based on what city I happened to be in, what I was thinking about at the moment, or with whom I just wanted to see and catch up. There were many natural prompts that would act as the impetus to sync with investors I care about irl. I borrowed that word “prompt” from Diana Kimball Berlin, who recently joined Matrix after building one of my favorite products ever in Quip. I think it’s a perfect word for what’s been lost in the age of Zoom.

In the absence of natural prompts, I’ve come to schedule reoccurring syncs for the people with whom I want to stay in touch. If I have a good conversation with a new investor, I’ll suggest we sync every 4 weeks or 8 weeks or whatever makes sense and I’ll send calendar invites going out months. It’s not my natural flow, I prefer to be more fluid, but it has been effective in collaborating with new people and deepening those relationships in the face of constraints.

Something I’ve observed in these syncs, however, is that everybody has a different style and intention coming into them. For some people, it’s just about our relationship with each other. For others, it’s about sharing ideas and thematic work. Some want to talk about market dynamics and what they’re experiencing on the field. Others want to share or receive potential investment opportunities. Personally, I value and appreciate all of those conversations. I gravitate naturally toward some more than others, but I’m flexible enough that I tend to let the other person define the time.

The downside of this approach, is that you can waste 10-15 minutes of a 30 minute sync in mutual discovery of what would be most valuable to the other person. When Chris and I do our partner meeting at Pace, we create an agenda in advance. There’s a lot of unstructured time and conversation, but it keeps us on track and ensures that we cover the things that are important to each other and the firm. This morning I started to wonder, what if I created a standing agenda for all of my investor syncs? VC to VC communication rarely comes with a written agenda. In fact, I don’t think I’ve ever seen it done before. Nobody has ever sent me a note in advance and said, here’s what I want to cover in today’s catchup. So I thought I’d try it. Here’s my proposed agenda for all my VC to VC syncs. I’m gonna send it to people and see if they’d be open to try it:

30 minute agenda (more time on 1, 2, &3 if we have a full hour together)

1) General catch up, personal life updates, etc. (5 mins)

2) Things you are thinking about (5 mins)

  • themes/theses/ideas
  • inspiring signals/products (what’s caught your eye)
  • Skip market dynamics even if you have been thinking about them (VCs can wast an entire hour complaining about valuations or behavior of other VCs or whatever)

2) Things I’ve been thinking about (5 mins)

  • themes/theses/ideas
  • inspiring signals/products (what’s caught my eye)
  • Skip market dynamics

3) Investments (You) (5 minutes)

  • recent investments you’ve made
  • things you are actively considering
  • things I should consider or look into

4) Investments (Me) (5 minutes)

  • recent investments I’ve made
  • things I’m actively considering
  • things you should consider or look into

5) Help (this one is borrowed form Julia Lipton at Awesome People Ventures, who is the first VC who has ended a meeting with me by asking “is there anything I can do to support you?” (5 mins)

  • anything I can do to be helpful to you (i know, i know…what a cliche)
  • things you can do to be helpful to me

This might suck and people (myself included) might hate it, but I’m gonna try it for a few weeks and see if I can’t improve the quality of my reoccurring meetings.