The power of investor updates

One of my top pieces of advice for any entrepreneur or startup founder.

One of my top pieces of advice for any entrepreneur or startup founder is to send a monthly investor update… even if you don’t have any investors.

For the past 26 months I’ve sent a brutally honest and detailed update to all investors, employees, family, friends, and colleagues.

It requires a decent amount of time and effort to aggregate all of the data and contextualize everything occurring within the business. I probably spend about 5 hours each month preparing it.

To be clear — I don’t have to do this at all. It’s not a requirement from our investors, and there are no real consequences if I were to choose to not continue creating these.

But I truly believe it’s one of the most valuable exercises I do for a few reasons…

  • Accountability — You can’t manage what you can’t measure. I know that each month I’ll be sharing the core metrics of the business… and I’m way too competitive to email nearly 400 people and tell them we barely grew last month. Rents due baby.

  • Communication — At any given time we are balancing a handful of product launches, growth initiatives, talent searches, process enhancements, and more. It’s dizzying, but the update is a forcing function to get all of my thoughts organized and onto paper.

  • Alignment — We’re an entirely remote team with people across 8 different countries. It’s easy for employees to get lost in their day-to-day and lose sight of the overall progression of the business. The monthly updates showcase how everyone’s work and initiatives fit together in the broader scheme of things.

  • Network — The recipients are a collection of people who, for the most part, have incredibly vast and valuable professional networks. Each update includes a few asks… like needing an introduction to a company or looking to hire for a specific role. Our odds of fulfilling these requests are drastically higher when directly asking those who have a vested interest in helping.

  • Top of mind — At the very least, the update itself is a reminder of what we’re building to nearly 400 people. As they go about their lives and participate in various meetings and outings, the likelihood they may connect the dots and recommend our platform to others only increases due to us being top of mind. This can manifest in new users, partnerships, advertisers, investors, or employees.

They’re also a super power if you’re looking to raise money from investors.

Ultimately, early stage investors just want to see that:

  • the business is growing with a clear upward trajectory

  • there’s a real opportunity to scale

  • you as the founder are capable of building and leading the company

I’d argue there’s no better way to clearly communicate that than providing regular monthly updates of your progress.

As I mentioned previously, we raised our $12.5M Series A from Lightspeed Venture Partners in just 6 days.


I added one of their partners to our investor updates after meeting him for the first time. When I reached out about exploring a Series A a few months later, he was already up to date and had full context on everything about the business.

Whenever I meet potential investors who express interest in beehiiv, I always just add them to my monthly update list. It’s 0 marginal work to keep them up-to-date, and the upside speaks for itself.

I’m also sure to keep every single investor who passed on us on the list as well.

You are dead wrong if you don’t think I have that extra bit of motivation each month to push us to hit new milestones.

Seed rounds typically happen before there’s any revenue or even before the product is built in most cases. Writing a seed check is just a bet on the founders.

And back in 2021 I had over 50 investors basically look me in the eye and say — “I don’t think you are capable of building this into a successful business.”

So I’d be lying if I said I didn’t have a huge chip on my shoulder to make beehiiv the biggest miss of their careers. And the investor updates are just a nice friendly reminder each month 🙃.

So what’s included in the investor updates?

They’ve evolved over the years, but in their current form…

  • Introduction — typically shouting out some milestone or personal life updates

  • The TL;DR — MoM growth metrics and capital activity

  • Primary updates — a deep-dive and status update on our product roadmap, some revenue analysis, growth initiatives, new hires, and more

  • Asks — where I make a few direct asks of the recipients

  • Product updates — recapping what we launched in the prior month

  • Accomplishments & wins — typically just one big win or shoutout to an individual, team, or initiative

  • Failures & learnings — key takeaways from something that either didn’t work or could be improved

  • Upcoming priorities — what are the top priorities for the upcoming month

And I don’t want to pat myself on the back, but they’re pretty fucking good.

But me telling you how great they are isn’t going to help you… so I’m beyond excited to share my newest drop for BDE 🚀

Introducing: the beehiiv investor journey.

You can sign up and receive every single investor update I’ve ever sent, one month at a time, from the very beginning.

The raw and unedited emails — so you can follow the ups and downs of the journey as if you were a seed investor.

If you enjoyed this post or know someone who may find it useful, please share it with them and encourage them to subscribe:

Credit: @archdose

Kind of feels like a rookie move to not show off the bookshelf behind where you’re sitting. But coziness levels and views are off the charts on this one.

Reply with your own AI generated office and I’ll feature it in an upcoming issue.

Turn on, tune in, drop out. Click on any of the tracks below to get in a groove — each selected from the full Big Desk Energy playlist.

Some of my favorite content I found on the internet this week…

  • NBA unveils state-of-the-art LED court for the 2024 All-Star game and I’m all for it (Twitter)

  • Kate Cole shares her story from being a hostess at Hooters at 17, to VP of Hooters by 26, to President and COO of Athletic Greens (Him & Her Show)

  • Apple ad for the Vision Pro (Twitter)

  • Car Dealership Guy is a… guy ? (Twitter)

  • beehiiv launches their monetization guarantee so all eligible users are guaranteed ad 👇️ 

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