How to stay in touch with 1000+ people

Kris Duggan of BetterWorks

On the right: Kris Duggan, Founder/CEO of BetterWorks and networking master.

It’s been said that people can only maintain about 150 relationships. But personally I think the bigger your network, the better.

A large and diverse social graph is an asset that pays huge dividends over time. Every week I rely on my network to get new intros, investing opportunities, and general advice for gadgets to buy.

The problem though is that humans are lazy and it’s too difficult to nurture a large network consistently. That’s why I’ve given up trying.

So instead, my strategy now is to write an annual holiday e-mail to update my social graph about my life. And it works great!

I’ve been doing annual updates for several years now. My recipients love it and it’s the perfect way to keep my relationships warm. This article outlines:

  1. How I create a list of contacts from my network
  2. How I structure my holiday message.

Before you read on, I am assuming that you use LinkedIn and have been keeping your contacts up to date. If not, don’t waste your time reading this article. You will need an active LinkedIn account to make this technique work.

How do I find and maintain e-mails in my network?

You’ll find that the steps below are really easy. But the hard part happens throughout the year as you meet interesting people and religiously add them to your social graph.

Whenever I meet someone new who is interesting, I’ve made a habit of immediately adding that person to LinkedIn. You should too because it’s a shame to lose a good connection. As I get older, I am consistently amazed by how a random contact I made a long time ago can suddenly become a critical gatekeeper for a partnership, a deal, or a key piece of information I need.

Right now, LinkedIn is the best social network that exists for managing professional relationships. So make it a practice of having your profile up to date and consistently add your contacts.

First step, download the e-mails in your network

LinkedIn makes it really easy to export contacts. Here are the instructions that you will need to follow; it’s a one-minute exercise. Once you open your downloaded .csv file of LinkedIn contacts, the info will be neatly organized with columns for:

  • First Name
  • Last Name
  • E-mail
  • Title
  • Company

LinkedIn Contact Export

Next, clean your list

This is where I’m going to lose a lot of people reading this article. The next step I take is to manually go line by line and delete the contacts of people whom I don’t care about.

This task takes a couple days to complete, but it’s a worthwhile exercise. If I don’t recognize a name, then I immediately delete the contact (that is, delete the row on the .csv file). If I see a contact with whom I’ve had a meaningful interaction in the past five years, the e-mail stays on the list.

Yes, it is time consuming and painful to filter all your e-mail contacts manually. But I actually enjoy this exercise because it reminds me that I know lots of amazing people, and I can also see through my LinkedIn file what the current title and company name is for each contact. It turns out that people change jobs a lot!

Use Gmail or Mailchimp to send your message

If you have less than 1,000 people in your now-clean holiday list, then use Gmail to send out your message. Uploading your list into Gmail is simple: just copy the column of e-mails from your clean .csv holiday e-mail list and paste into a new e-mail.

Copying Contacts from LinkedIn

Copy the column of e-mails.

Be sure to put the e-mails in the BCC: field, not the TO: field — generally it’s bad etiquette to expose your contacts to one another without their permission.

Pasting Contacts into Gmail

Paste the e-mails into the BCC field.

Gmail allows you to send one e-mail message to up to 500 people every 24 hours. So with 1000 contacts you will need to send your message to half your list one day, and the other half the next day.

Otherwise if you have more than 1000 contacts in your holiday e-mail list, use Mailchimp.

Mailchimp is free so long as you have less than 2000 contacts that you are e-mailing. It’s easy to upload your .csv file of clean contacts into a new newsletter list.

Uploading Contacts to Mailchimp

Once your contacts are in a Mailchimp list, you can then use their fairly friendly user interface to craft a message to your contacts and schedule when the e-mail should go out.

How to craft your e-mail

Here are some principles you should follow when crafting your e-mail:

  • Keep it short – Only highlight three major things that happened to you during the year. The whole message should take no longer than one minute to read.
  • Keep it informal – Use the same tone you would use when speaking to a friend. No one likes formal e-mails, period. It makes you look lame.
  • Keep it positive – No one likes a Debbie Downer. If there is something negative you have to share, try to present it with a positive attitude. Example: “I got cancer, but don’t worry because I’m going to crush it.”
  • Make it an e-mail – A lot of people share a .pdf or a link to a video for their holiday e-mail. Don’t do that, make the message truly an e-mail that people can just open and immediately consume.
  • No templates – This tip is specifically for people using Mailchimp or some newsletter service. Just use simple text, it will make it easier for people reading your message from their phone (assume that will be most people).
  • Have a call to action at the end – Ask people to hit reply back and say hello.
  • Include your latest contact info – Put that at the very end, so people know how to reach you — especially if you moved in the past year.

Example of a fake holiday e-mail

Here is a fake holiday e-mail I put together to show you all the principles above in practice.

SUBJECT: Happy Holidays from Joe Smith – 2013!


Hi there!

Hope you guys are enjoying the holidays! 2013 was an awesome year for me and I wanted to share my highlight reel with you.

Kelly actually agreed to marry me!

How the hell did I trick this amazing woman into saying yes? I’m delighted to announce that Kelly and I got engaged in April.

We bought a house in San Francisco

Kelly and I bought a house together in the Mission. We love our neighborhood and recently invested in tighter pants and ironic t-shirts to blend in with the folks in our area.

I graduated from law school!

Because just having a mortgage debt wasn’t enough, I finally graduated from my expensive-ass law school in the summer. I am now an associate at Boring Soul-less Law Firm, LLP. I plan to make partner in just 25 years.

I hope that 2013 was a great year for you too. If you have a moment, hit respond and let me know how you’re doing.

Wishing you a great 2014,

Joe Smith

My current contact info:

Joe Smith
[Insert Address]
[Insert Phone #]

/* One more tip: sometimes it’s fun to add pictures below each highlight headline. I usually do that for my own annual updates. */

What are you waiting for? Send an update to your network now!

This technique does take work, but believe me when I say that your network will LOVE your annual updates!

One of my favorite things is meeting up with a contact at some random point in the year and having that person say that they loved my annual message. I’ve gotten that feedback probably a dozen+ times each year since I’ve started doing these e-mails.

A request: After you send out your own annual update e-mail, leave me a comment below and let me know what you thought about the whole process and how your recipients reacted. Happy networking!

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