2025 Company Offsite

The most underrated skillset as a founder: storytelling.

The beehiiv “story” is what allowed me to raise millions from investors, hire talented employees, and continues to motivate our employees to work towards our ambitious goals.

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It’s currently midnight Friday night, and I’m up solo writing this on the rooftop of our Airbnb in Tulum. The rest of the group passed out hours ago, but there’s no severity of hangover that would allow me to sleep right now.

I’m so inspired and full of energy after spending the past week with (almost) the entire company.

beehiiv is entirely remote, with nearly 100 employees located across more than a dozen different countries; but each year we come together IRL for our annual company offsite.

Last year we hosted it in Montreal. This year we descended upon Riviera Maya Mexico to work, collaborate, and have a whole lot of fun.

I’m not going to sit here and write something new or profound about the magic of IRL collaboration. It’s amazing, everyone agrees, no think piece needed.

What’s amazing is that I can find a bug, make eye contact with the engineer with the most context, and walk right over to have it resolved. That and all of the breakthroughs that occurred over meals that otherwise would have never happened.

What’s less amazing is the context switching required for that engineer to fix that bug or the hundreds of other interruptions and side quests that occur from working together in one large open conference room.

But I guess the trade off of creative spontaneity and collaboration is focus.

Which explains why reflecting back on the week, I feel a strange paradox: less work “got done,” yet more progress was made than would have happened remotely.

Of course, the purpose of the company offsite (the one time a year we get together in person) isn’t purely about output. Otherwise we’d all sit in silence with our headphones on like a bunch of code monkeys cracked out on adderall (which actually sounds pretty dope).

You can’t put a price on the camaraderie of being in person and rubbing shoulders with a team made up of such talent density. It’s motivating, inspiring, and allows everyone to build much deeper relationships than the surface-level stuff that happens online.

Here’s how it all went down…

People began arriving early Monday morning. We had a massive conference room setup with tables to have people work and hang out. Then we had a big welcome cocktail hour and dinner by the pool at night.

Tuesday was the first full work day. We launched a handful of new features (shoutout automation templates 🥳) which was much more fun to do IRL.

I gave a 90 minute presentation on the state of the business and a handful of trends and initiatives I wanted the company to rally behind.

The rest of Tuesday was filled with tons of productive meetings, unlimited tacos, and the birth of the 5pm pool move (where the entire company begins to crowd the swim-up pool bar to enjoy the last few hours of sunshine).

The Tuesday dinner turned into a bit of a fiesta that rolled right into a karaoke night. It turns out there are a handful of people who are very musically talented… and some who aren’t.

Wednesday morning was an early one as our resident pádel player recruited us to play at 6:30am before work. Afterwards we hit a kosher breakfast spot that conveniently allowed me to wrap tefillin for the first time in 17 years and make my mom proud.

Praying for the competition 🙏.

The rest of Wednesday was incredibly productive — lots of round tables, meetings, and product sessions.

Thursday was our final full day together. It began with the usual gym, breakfast meetings, normal meetings, etc. and ended with what was my favorite part of the entire trip: employee pitches.

More than 20 people presented ideas ranging from new podcast and audio features to social integrations to AI features and everything in between.

It was a reminder of just how creative and talented everyone on the team is, and how high the ceiling is to continue pushing forward and building new things for our users.

The coolest part is that we have since went on to actually launch a handful of things that were pitched at last year’s offsite.

That was followed by beehiiv trivia and the final 5pm pool sesh of the week. Oh, and a calm nightcap with 50+ members of our team and a dozen bottles of 1942.

Zero casualties and only two people who had to be wheel-chaired back to their room. I’d consider that to be a pretty successful night.

On Friday mostly everyone departed back to their respective homes. A handful of us stayed back and headed to Tulum to keep the good vibes rollin and to work from here for the week.

I spend the majority of my days buried in what feels like an insurmountable amount of stress and anxiety, and often fantasize about this ideal future state where things are just “better.” I’ve also been told that as a founder that day will never actually ever come; there’s always another hill to climb or fire to fight.

So I’ve been doing my best to more consciously enjoy the journey for what it is.

Well, here I am up alone at 2am on this rooftop writing, smiling, and reminiscing about all of the chaos.

I’m enjoying it ✌️.

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/2025-company-offsite

Shoutout Mark for the reader submission 🫡.

Notably missing: external monitor and floor to ceiling windows. Not a bad view though.

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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…

• An inside look at where Capitol Hill meets Silicon Valley (Pirate Wires)

• Scott Galloway shares his thoughts on the potential brain drain of America (No Mercy, No Malice)

• This founder just launched an AI clone of himself (Inc.)

• New build in public tutorial incoming👇️👇️ 

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Until next Tuesday 🕺🏽

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