How to write a great investor update

This past week I had the privilege of catching up with America’s fourth favorite CEO - no, not Brian Chesky - Marc Hostovsky of Minoan Experience.

Minoan is changing the way short term rental owners outfit their properties with furniture, while also making those same rental spaces shoppable experiences for guests. They’re pioneering a category they call “Native Retail”.

I’m an angel investor in the company, and their quarterly email update inspired this post. You see, their progress was 🔥… they’re killing it! But I noticed a few gaps and changing metrics. I spoke with the CEO, offered some advice.

Here’s a guide to crafting a world class investor update.

You don’t want to leave your board hanging until the end of the quarter for an update. This group deserves some extra TLC. That’s why I recommend writing a monthly “flash” note to your board.

This should be sent within 48 hours of each month end. That means there’s no need (or ability) to include accounting metrics like GAAP revenue or operating income, since the books won’t be closed yet.

The idea is to get in, and get out, with a handful of key performance metrics to hold them over until the broader quarterly update to all investors on the cap table.

Note that all of these metrics should minimally have a Y/Y growth rate to demonstrate pacing, and also a M/M rate if it’s relevant to your business.

While this sounds like a lot, all of these should be automatically calculated at the end of each month and show up in a single dashboard for you to pull from. Great teams will build these in Sigma or Looker and simply login the morning after the month closes to see where they landed.

To close out this note, remind your investors as to when the next board meeting is (and extra points if you include some things you’ll be talking about).

Now that we’ve finished the appetizer, let’s get to the entrée.

Here’s a template you can repurpose each quarter:

The company, both internally and externally, should hone in on three to four core metrics for the year, and consistently report on them. That means you update your investors on the same metrics four times throughout the year.

Now, the targets you bump your results up against and communicate externally may be a bit different compared to those you track internally, as most finance teams build some cushion into the operating plan to make sure they hit your board plan. But the metrics themselves don’t change.

To be clear - the org and the board should be looking at the same metrics.

And do not pick more than four. If you do, it will look like you are pushing people in too many directions and lack focus.

As my old boxing coach used to say:

And don’t change the metrics you report on period to period. That’s a big red flag.

Why?

Now, you don’t need to keep these metrics the same forever. There are different metrics for different chapters in your lifecycle. But don’t change them mid year. Wait until you do your annual planning in the following year and anchor to those figures consistently.

A note on growth rates - you need to add “trending” context to your ARR / GMV / Revenue / Customer counts. Where applicable, state them consistently in terms of both Y/Y growth and Q/Q growth.

The only reason you shouldn’t quote Y/Y is if you were starting from a base of, like, zero a year ago. But the point is you should never show a “naked” metric. Numbers void of context lack insight. People need to know how fast you are accelerating or decelerating.

Cue the highlight reel!

This should harken back to whatever you told the board you were going to do. Think about the pillars of the business’s strategy. Report back on those (if they are going well).

And make sure this isn’t purely financial - give some love to the product and engineering teams. Call out some things you’ve shipped that customers asked for.

Leaving out non-financial wins is a big mistake I’ve seen in investor notes. Yes, we are trying to create shareholder value. But you are painting a wholistic story about a “healthy” org with all departments firing on all cylinders.

As a CFO, since I already know what we accomplished from a finance and sales perspective, at the end of each quarter I reach out to the heads of People, Product, and Marketing for some of their wins. And in terms of process, I consolidate a list of headlines and then let the CEO pick out their top three to five.

I like calling “lowlights” “areas for improvement”. This is so:

The last point is crucial. You never want to point out something that isn’t going well and then walk away.

You need to marry it with a declarative statement on what you are currently doing to fix it.

Here’s an example:

As a side note, I’ve worked with a CEO who always wanted to put at least one more item in the “Areas for Improvement” list vs the “What’s Working” list. They wanted the board to think we were more critical of ourselves than they could be.

Just like Lil Dicky, we’re never satisfied!

To a certain extent, I agree with this curmudgeonly attitude. But it walks a fine line between dumping on your business and celebrating wins (which keep people motivated!)

You also don’t want to reveal too much of how the sausage is made, so don’t reach for things that are going wrong just to make the list longer. You don’t want to make yourself look bad for no reason. Don’t fall on your sword for the sake of doing so.

In this section you should “tease” things that you know are already showing promising signs and describe how you are attacking them in the coming quarter.

Examples may include:

Each board meeting should have a theme. You want to remind your board as to what the “meaty” topic will be for the next session, and who from the management team other than the CEO and CFO will be there.

Roughly speaking, this is what I’ve seen work:

Depending on what your board expects, and the level of visibility you have on where you’ll end the year, the Annual Operating Plan approval could be in Q3 or Q4. If you are on a normal calendar year schedule, it’s great if you can get it approved in the Q3 board meeting in late November around Thanksgiving. This allows you to roll into January where sales reps all have their plans in hand.

But regardless of what you scheduled as a topic at the start of the year, you should always focus on what’s critical for the business in that moment. Don’t stick to something that’s irrelevant just because you slotted it in back in February.

Investors are good for three things:

You’ve already taken #1. Now don’t go quiet and forget to ask for help on #2 and #3.

Is there a key customer intro you need? If you are a B2B SaaS company, it’s a great idea to attach a slide with the top 25 accounts in your pipeline that you’d benefit from an intro. There’s a good chance that your board member knows someone there, or has a colleague who does.

The same goes for key roles you are trying to fill. CMOs don’t grow on trees. And the best roles aren’t filled from a LinkedIn rec.

Remember - this is not a burden for your investors. It’s in their vested interest to help you with customer asks and employee intros. Both help the share price go up.