How to Write Update Emails that Help, Not Annoy

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If you are in any kind of field where you want others to reach out to you and help you from time to time, please send update emails.

If you’re running a venture-backed startup, please send update emails to not just your existing investors but also to stakeholders, advisors, people who you want to *make* advisors, and potential investors.

If you write a book, please send update emails to the people you interview for the book.

If you have a big network spread out all over the country and you just want to see if there are people with whom you should connect when you go to a new part of the country, please send an update email.

My point here is: update emails are a polite, non-invasive way to get other people who *want* to help you to help you. I’ve sent occasional update emails through this blog for the last few years and those have resulted in me publishing two books, being paid to give talks, flown to Mexico for a conference, and numerous friendships.

And I urge people to send update emails all the time through my work with 1517 Fund.

I think a lot of first-time makers (i.e., founders, writers, publishers, podcasters, etc.) shy away from sending update emails because they have a fear of rejection. They fear people unsubscribing from lists or not liking what they are working on or getting angry that they are being emailed by this person. Or they assume that people would just reach out if they were interested. Neither of these are really true.

People think about you much less than you think. Realizing this is liberating. It means that people aren’t sitting around getting angry about emails you send — it also means that they aren’t actively checking much of your stuff (i.e., your startup, your blog, your book, your podcast) unless you ask them to check them out.

People are also kinder than you think. Sure, you get the occasional crazy angry person on the Internet, but social media platforms are designed to maximize for angry outrage, not serendipitous outreach.

With these two facts of human nature in mind, an occasional update email can be a great, kind way to keep people who would otherwise like to help you but aren’t actively thinking about you in mind.

“Help me help you”

If you’re a creator of any kind trying to get advisors, stakeholders, or investors, you’ll have meetings and conversations with these people as you advance.

At the end of these conversations, simply ask:

I send an occasional update email once every [PERIOD], may I add you to it? It’s just a plain-text, BCC’d email.

99% of people will say yes — I have actually yet to meet somebody who would say no, but they may be out there. This is a quick, polite way to help these people help you. And it makes it much less likely that you’ll have to depend on their own internal tracking systems to stay top of mind for them.

(This is especially important for investors who may not be ready to invest yet but want to track your progress over time.)

You don’t need to put emails on a specific schedule, just send them regularly enough that the person has a few data points to track your progress over time. I generally suggest starting with once every month or every other month. Every week is too often. Once a quarter can be okay if you have substantive progress, but that risks the email falling through cracks if you’re on an aggressive fundraising/publishing/release schedule.

Simple is Great

The actual body of the email can and should be simple. There’s plenty of information out there on updating actual investors, but the people on these update emails can simply be friends, advisors, or anybody you want to keep in the loop.

As such, you don’t have to go into a ton of detail. You don’t have to position the email a certain way.

You just need a few things:

  • Progress since the last email
  • Challenges you’ve run into
  • Asks

Each of these doesn’t have to be long.

Progress can simply cover, well, progress. If you’re building a startup, mention some new featured you built or new integrations you launched or new customer discovery you completed. If you’re writing a book, mention the new chapters you finished. The point here is to show that you’re still doing stuff since the last email went out.

Challenges are a good opportunity to show humility and seriousness. I tend to be somewhat skeptical of multiple updates in a row with no challenges, especially for anything really hard like starting a company or writing a book.

Asks is a good place to leverage your network. I would focus on introductions but you can also use this as an opportunity to request guides, resources, grants, etc. People on the emails want to help you, so don’t be afraid of asking for help.

Finally, these emails should NOT be sent via a newsletter service like MailChimp. MailChimp, Sendfox, etc. are great for blog update emails or company update emails, but they have a tendency to be filtered to a “promotions” inbox and for people to just view them as newsletters.

Simply BCC people on a plain text email you write in Outlook or Gmail (for about two years, the updates for went out through this format, too. It was only once I got over 1000 subscribers that I realized I had to have a better system for sending update emails).

Remember, the people on these emails agreed to be kept in the loop because they want to see you succeed and they think they can help you. Don’t be afraid of helping them help you.

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