Send More Investor Updates
I’ve made like a hundred angel investments over the years, and I get the sneaking suspicion that the most successful startups in my portfolios are the ones that talk to their investors.
Like, that’s it. That’s the nugget for this post.
Holy shit no one can help you if they don’t know you need help
Like most good advice, this is kind of obvious, but writing about it just serves as a reminder and/or a kick in the pants. To wit: it’s hard to give help if you don’t know what help is needed.
Let’s back up a second. First: venture-backed companies are relatively rare, in the grand scheme of things, and that’s fine and dandy. But if you are one of the companies where it makes sense to take outside investment, just cashing the check and moving on is pretty small-minded. The whole point of selling part of your company is to bring on people with a network and experience different from your own. If you’re not doing that… take out a loan or rob a bank.
Lead investors tend to be much more involved in a company- they might have prescheduled check-in periods and have a deeper understanding of what’s going on. But for everyone else, particularly angel investors, the monthly investor update is the only real connection they have to your company, past simply existing on your cap table. Use and leverage them!
Less is more
I swear, if I searched in my inbox for “sorry it’s been awhile since we sent an investor update!” the results would be… high. And I get it! It’s kind of stressful, particularly if you have stressful things in your present or your future. And usually it just keeps compounding until the dam bursts and once a year there’s a “OHMYGOD HERE’S A WAR AND PEACE-SIZED TREATISE ON THE COMPANY BECAUSE IT’S BEEN SO LONG ALSO PS: WE’VE PIVOTED TO SELLING SMALL TREES FOR CATS TO PLAY ON”.
So your easy answer: just send a quick paragraph! Nothing needs to be rocket science. I’ve gotten a number of updates that broadly consisted of:
Hi! This is what we did this last month:
[ some cool hip things ]
Here’s what we need help with this upcoming month:
Nothing! We’re doing good, just heads-down on the product right now.
I love these! This tells me 1) what you did, 2) what you need help on (nothing!), 3) that you’re still alive, which you’d be shocked at how often that’s a real question. I’ve had a couple investments now where the only communications were “thanks for your investment!” and “we’re shutting down the company!” In hindsight: absolutely not shocked the company died.
Better companies communicate
Look: I don’t traffic in shit like “science” or “math”, much less call it “maths” like those weird loveable Brits keep trying to push. I’m an angel investor, baby, so that means all I need are vibes, mannnnn. But I keep getting the feels that founders who are on top of their investor updates are… better.
Almost certainly the best investor updates with the most regular cadence over years was from Sid Sijbrandij, for GitLab’s investor updates. There was a very credible rumor on the street that NIST sets their time servers based on Sid’s email cadence. They were to the point, plaintext (don’t get me started on all the fancy investor updates founders are trying to get by with these days), with clear call-to-actions and jump-off links if I wanted to dig deeper into that particular topic or internal discussion.
I’m not going to say if you take Sid’s same approach you’re also going to also have a $15B IPO like GitLab did… but I’m also not not saying it.
So give your investors a shout. Even if I invested in your company and it’s been awhile but you don’t want to send an investor update after reading this because you’re worried it’s now uncool to send one out right this minute because other companies are prolly going to do it and you want to be a unique cool snowflake? I definitely wrote this for you. Just send it! You’re going to forget it if you push it out a few days anyway. Promise.