Startup founder base play: monthly investor updates

Startup Founder base play: monthly investor updates | Hoala Greevy, Joe Montana

On 4 April 2018 I got to meet NFL Hall of Fame quarterback Joe Montana. He spoke at a book club gathering in San Francisco, which I blogged about.

One of my takeaways that night was the term base plays. On a football team, these are the simple plays you learn early in the season. They’re also the same plays you go back to all the time.

I wrote on a post on my personal base plays, which you can read here. I reread it tonight and they remain relevant today, as we continue our mission to become the market leader for HIPAA compliant communication.

This post is another base play I’ve used as a startup CEO: monthly investor updates.

Monthly investor updates

Jason Lemkin, Hoala Greevy: Startup Founder Base Play: Monthly Investor Updates
Selfie with Jason Lemkin, 22 March 2017

Most startups send quarterly updates to their investors. These updates often include things like core metrics, highlights, asks, and remaining runway. As a fundraising tactic, it’s even been suggested for early stage startups to send them to potential investors.

In 2016, I recall reading a Jason Lemkin blog post, similar to this one, that leveled me up as a CEO: The monthly investor update. Rather than send updates every three months, Jason proposed monthly investor updates are better. No surprises. Keep your investors happy and engaged.

Starting in December 2016, I’ve sent monthly investor updates to our investors. Even though it’s impossible to have stellar news every month, it’s been well received. Startup investors don’t expect incredible news each month.

Here’s my template for the monthly investor update. It’s evolved over time, mostly from feedback I get from our investors.

Keep in mind we are a B2B SaaS startup, so what follows are metrics that matter to our business.

Monthly investor update template

After a quick intro, I’ll start off with a mahalo section. Investors and advisors appreciate kudos when they’ve been helpful. I lead off the update with it.

Following that, I’ll list Key updates. To us, they are:

In the third section, I’ll list Highlights that happened in the business last month. Bullet points are best.

After that comes the Lowlights section. Ideally there’s less bullet points listed here.

Next up comes the Blockers section, which are things getting in our way.

That’s it.

Optionally, I’ve been sending photos of things happening in my life, which are also appreciated.

Here’s one I included in our February 2023 investor update:

Hoala Greevy kayak fishing in 2023, Uku

Getting in the water is stress relief for me, so water time is arguably great for the business 🙂

Hope this helps!

About the author

Hoala Greevy

Founder CEO Paubox. Kayak fishing when I can.

Read more by Hoala Greevy

Get started with
end-to-end protection

Bolster your organization's security with state-of-the-art email encryption and inbound email security.

Highest rated HIPAA compliant email solution on G2

EmailEncryption BestMeetsRequirements MeetsRequirements
SecureEmailGateway MostImplementable Total
SecureEmailGateway Leader Leader
SecureEmailGateway EasiestToUse EaseOfUse
SecureEmailGateway EasiestAdmin EaseOfAdmin
SecureEmailGateway BestUsability Total
SecureEmailGateway BestResults Total
SecureEmailGateway BestRelationship Total
EmailEncryption UsersMostLikelyToRecommend Nps
EmailEncryption MomentumLeader Leader
SecureEmailGateway BestSupport Mid Market QualityOfSupport
EmailEncryption BestMeetsRequirements MeetsRequirements
SecureEmailGateway MostImplementable Total
SecureEmailGateway Leader Leader
SecureEmailGateway EasiestToUse EaseOfUse
SecureEmailGateway EasiestAdmin EaseOfAdmin
SecureEmailGateway BestUsability Total
SecureEmailGateway BestResults Total
SecureEmailGateway BestRelationship Total
EmailEncryption UsersMostLikelyToRecommend Nps
EmailEncryption MomentumLeader Leader
SecureEmailGateway BestSupport Mid Market QualityOfSupport