Scaling relationship building

I put the most of this document together by hosting a discussion with a few friends and taking notes. Afterwards, we talked about the patterns we noticed.

Actionable takeaways

  1. Broadcast updates. Write a monthly newsletter about your life for your friends or post to Twitter.
  2. Take selfies with new friends and send it to them. Send a few words about what you talked about, too. It'll remind them what you look like and when you connected.
  3. Organize the conversations you want. When you notice that even 2 or 3 other people share an interest, plan an event for it.
  4. Relatedly, start group chats. It's easy and convenient.
  5. Matchmake at parties. Find friends that don't know anyone and walk around with them until you find someone they should meet.
  6. Use a CRM only to solve extremely specific problems. Implement those systems with checklists or trigger-action plans.
  7. Don't worry about reaching out to individual acquaintances so often. Professional networkers (like VCs) seem to do this, and it's usually begrudgingly appreciated by the recipient, but regular people seem to get by just fine by investing mainly in their best friendships and maintaining acquaintances via broadcasting on social media and planning events. This, for me, is a huge relief and a major update.
  8. Conversely, text friends whenever I think of them. The weirder, the better. Virtually any type of contact is good for the friendship.

The sum of these updates is that I'll batch weak ties instead of maintaining them individually, freeing most of my social energy for my best friendships, which feels great!

People managing 1,000+ people communities or professional networks

Erik Torenberg

  • No CRM
  • Twitter
  • Substack
  • Organize events, mainly unconferences, to introduce friends to each other
  • Mostly proactive within a small circle

Mackenzie Burnett

  • No CRM
  • "Unusually good memory for people / what they’re up to / how they could be connected"

Vishal Maini

  • Unusually thoughtful followup links
  • Always positive interactions

Philip Chao

  • Quick pings randomly, but on average once per month ("Hey, how's it going?", "Yo", "Saw this thing, thought of you", "We haven't caught up in a while, want to do a quick call?")
  • Helpful - brought $500K from other investors into a round
  • Also does selfie + contact info thing from Julia (as does Justin Trudeau?!)

Brian Talebi

  • Hype introductions
  • Befriends interesting and powerful people

Chris Painter

  • Pings people whenever he thinks about them, without hesitating - especially if it's weird (dream, etc)
  • Basically any interaction/outreach, no matter how small, strengthens his relationships
  • Asks how he can help his angel investments every couple weeks, suggests ways.
  • When a mentee is going through a key phase, follows through every 1-2 weeks on ways to help
  • Full-time at parties/conferences thinking of people combinations: walk around with people that know nobody at the party, point out people, then thinks of 2-3 things they have in common ("Both had tacos last night, complicated relationships with moms")

People managing <1,000 person communities and friendships

Jasmine Sun

  • Full-time motivating people and helping them clarify ideas under an ideological umbrella (Reboot)
  • Organized writer's retreat
  • Started a list of social games, put up a website for it
  • Comes up with something she wishes she and her friends were doing, names it, finds someone that would be great for it, then hypes that person up to do it. Low bar for trying to make an idea "happen"

Jeremy Nixon

  • Similar to Jasmine, in that he comes up with ideas and inspires people to join
  • Approached Chrispy: "We should organize these Inspired Autodidact events. You should do the logistics" and that's how they became friends lol


  • Notion CRM for many specific problems/opportunities: interest in coliving and/or recurring events I organize, whether they're single and interested in being set up with friends, etc.

Julia Bossmann

  • Thoughtful event invitations
  • Any time there's a problem to be solved, makes an event to talk about it
  • Introductions: makes sure they're both at an event and know about each other instead of 1:1
  • Takes selfies or group pics, sends it to them after the party! If there's a point of connection, feature that in the photo

Ben Mann

  • Monthly newsletter, humble tone, has sections for life events & media he recommends

Daniel Benn

  • I’d also recommend being maniacal about setting up friend groups whenever possible. Individual relationships are much harder to make time for and manage, and can result in those “solo friends” feeling distant or neglected without the necessary QT investment. It’s just so damn convenient to shoot out a group message and see who bites. Obviously, having authentic individual relationships within that group is important too.

Michael Andregg

  • At Lighthouse, low-friction conversation starters via shirt-sized post-its with a format that answers basic questions (name, workplace, 3 things you want to talk about)
  • Notion CRM

Michael Lai

  • No generic system
  • Specific systems that solve problems, like investing
  • connect around activities he spends the most time on like running together or reading together
  • be a part of communities where there are lots of events

Rose Wang

  • Randomly polls friends and experts about interesting questions she's wondering about, develops her thinking with each call
  • Makes people feel good by being energetic and warm