I recently caught up with Christine Tsai over coffee in Waikiki.  We first met in 2016, when Paubox was part of Batch 18 of 500 Global’s Flagship Accelerator. 

As we sipped on Starbucks during that windy and wet morning, we got to the topic of effective investor updates. 

According to Christine, she prefers them to be:

• Concise
• Easy to read
• Bullet points > essays

Christine told me she enjoys our investor updates, as they’re usually pretty detailed. With over 3,000 companies in the 500 portfolio, I was flattered by the compliment.

As such, this post will be about how I compose our investor updates for Paubox. 

Selfie with Jason Lemkin, 22 March 2017.

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

In 2016, I recall reading a Jason Lemkin post, similar to this one, that leveled me up as a CEO: the monthly investor update. 

Rather than send quarterly updates, Jason proposed sending them monthly. 

No surprises. Keep your investors happy and engaged.

Christine agrees, she calls monthly investor updates the “the gold standard.”

I’ve sent monthly investor updates since December 2016. Every month. Good or bad. 

Even though it’s impossible to have stellar news every month, they’ve been well received. 

Don’t sweat it, startup investors don’t expect incredible news each month. 

Batch 18 in 2016, back when 500 Global was known as 500 Startups.

Here’s my template for our monthly investor update. Each section is a collection of bullet points. No paragraphs of text. No essays.

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

After a one sentence greeting, I’ll start off with the Mahalo section. Investors and advisors appreciate kudos when they’ve been helpful. Here’s where I let them know.

Here’s a recent example:

Mahalo to:

• Angel investor, family friend, and Paubox customer Chris Cruttenden for timely advice on dealing with tricky terms on a contract with a mutual customer.
• 500 Global CEO Christine Tsai for inviting me for coffee last week in Waikiki (see attached). We were part of Batch 18 in 2016. Mahalo for the shirt :)

Following that, I’ll list Key Updates. For us, I choose top level SaaS metrics like ARR, logo churn, revenue churn, cash in bank, etc. 

For more nuanced metrics that deserve to be segmented by customer size, I left them out. Examples here would be cost to acquire a customer (CAC) and CAC payback period. When you’re first starting out, focus on reporting the top line metrics first. I think you’ll be surprised how much work some of these take to compile on a monthly basis.

Here’s our Key Updates section:

• Annual Recurring Revenue
• New Bookings last mont
• Revenue churn
• Annual Logo churn
• Net Promoter Score
• Total customers
• Employee headcount
• Cash in bank

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

Here’s some recent examples:

• Staffed our largest booth yet at HIMSS24 in Orlando. See posts here, here, here, here, here, and here.
• Attained 53 5-star G2 reviews in Q1. We're now at 359 total reviews with a 4.9 out of 5.0 rating.
• Net Promoter Score (NPS) is 77 for the year so far. In context, any score above 50 is considered excellent in B2B SaaS.
• I attended my first in-person meeting for 10X CEO

Next comes the Lowlights section. Ideally, less bullet points here.

Here’s a few past examples:  

• Our AWS bill remains elevated.   
• Notable churns and downsells: (list them here)  
• Our Outbound SDR team started off the year with 7 people, now it's down to 4. Our latest SDR employee to leave got poached by Salesforce. I had no idea we were on the radar of Salesforce's recruiter team.

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

That’s it.

Optionally, I send photos of things happening in my life. Getting in the water is stress relief for me, so water time is good for business =)

36 pound Pacific Halibut (included in June 2023 investor update).

Aloha!
Hoala Greevy
Founder CEO, Paubox
Batch 18, 500 Global Flagship Accelerator