Building a successful startup requires a ton of energy and focus. I eat healthy, hit the gym daily, and prioritize 8 hours of sleep… but I was living in the dark until I started using Superpower last fall.

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Upgrade Your Health

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 40-something 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 14 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.

How?

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.

That same thing happened for our $33M Series B, which start to finish took just a few short weeks.

Instead of grabbing coffee or taking meetings with investors, I typically politely decline and add them to the monthly update list instead. 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.

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

And back in 2021 I had over 50 investors tell me they didn’t think we were capable of building this into a massively successful business.

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. Hitting new milestones and sharing them with all the people who didn’t believe in us is as fulfilling as it gets.

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 (shown above).

  • 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.

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

A reply from last month’s investor update

If you’d like to read every beehiiv investor update that I’ve ever sent, starting from the very beginning, you can sign up to begin receiving them for free here.

And if you need a platform to send your own investor updates, I hear this beehiiv platform is pretty good for that too…

If you enjoyed this post or know someone who may find it useful, please share it with them and encourage them to subscribe: mail.bigdeskenergy.com/p/monthly-investor-updates

Credit: Chris Abraham

Shoutout Chris for the reader submission. I can feel the annoyance of having the chair’s wheels roll on and off the rug throughout the day… but at least we have nice mountain views.

Think you can generate a better office? Reply with your submissions 📨.

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…

  • Really tremendous interview with Bill Gurley about startups, VC, and AI (Colossus)

Chat with DenkBot — my AI clone. It’s trained on everything I’ve ever published and the entire beehiiv knowledge base 🧠.

It’s also trained on my voice, which means you can call it and have full conversations. Give it a try and let me know what you think.

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