(I hope you don't hate it)
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5/22/25
We live in a very busy world. The noise is loud.
It's hard to stay "top of mind". Too frequently a great conversation can quickly drift into the abyss. A great person will enter and exit your orbit in a flash. It's just how the world works. A very small percentage of people we interact with are able to be maintained, fostered, invested in. And that's okay. In work, we're all victims of this -- and guilty of this.
But my goal here is to help founders harness that extended community. To pull in more people who can help you succeed. Connecting back to our OGs -- "it takes a village".
There's two pieces to this.
1) Staying on the radar -- having an easy way to float back into peoples headspace (monthly updates on your business)
2) Breaking the noise -- breaking from the boring / stale status quo (e.g. templated investor updates), pulling people into the journey (sharing something that's authentic and interesting and rich in "story")
If you do a good job doing this, it can help you in many ways.
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You’re on the radar of people who have shown interest in what you’re building.
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You’re showing momentum and traction on an ongoing basis. People see the progress and like to align with winners.
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People will forward the email and connect you to new people.
List Building
Start with a haul of your contacts (calendar, email history, spreadsheets, LinkedIn, cell phone) -- linking back to conversations that were pleasant and enjoyable (optimizing for energy). Add nice people that have been encouraging and helpful. Cast a wide net.
Then once a month go through your calendar and sent emails. Manually add people to your investor newsletter that you had a pleasant meeting with in the previous month.
Be liberal with this. You never know who can help you, and who might know the perfect person for you. This is not limited to “angel investors”, this is a very broad scope.
These are the people you're pulling into the story of your business (and they'll likely invest too!).
Style + Tone
Emails should be in plain text, directly from you, with all contacts in BCC. There should be an opt out option. And the style can go in two directions --
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From the heart, vulnerable, open, blog post style, fun, friendly, authentic
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Structured and professional
I personally like the first style. It’s unique, interesting, differentiated, personal. I think this is what people really want. The world is so stale and structured and formal. Building a business is so scrappy and hard and fun and painful. It’s ripe for good storytelling, and I think a very powerful way to differentiate yourself. Tell a good story.
I find the second option to be a bit stale. The over professionalized investor update that they teach you at YC / Tech Stars makes everyone look the same. It lacks differentiation and I think the over professionalization / standardization shows. I’m less likely to read it.
But you should pick the style that resonates with your vibe, brand, and personality. Both work. The key is that you’re doing this consistently and building a foundation over an extended period of time.
For more casual updates, I like this format:
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2-3 sentences — sharing your optimism about the business, framing the month
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4-5 bullet points of the biggest wins in the month
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2-3 paragraphs, free writing / reflection, contextualizing the bullets
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Pointed asks
Talk about your craziest day last month. Good, bad, fun, ugly, chaos. Tell me a good story! Make it interesting for people to read.
And send it on the 1st. There's a certain signal with that. It shows you're on top of your shit. Do that consistently for multiple months and people will take note.