What It REALLY Feels Like to Host An Offsite: A Founder’s Vlog to 155,000 YouTube Subscribers
Stan co-founder/CEO shares his perspective on their recent team retreat we planned for them in Park City, Utah.
When you think about company retreats, it’s easy to imagine the Instagrammable moments—group photos in the mountains, team bonding around a fire pit, or a CEO giving a toast over dinner.
But what you don’t often see is the intention behind the scenes, the financial commitment, and the leadership challenge of turning a multi-day offsite into a true driver of team alignment, trust, and execution.
That’s what makes this video from our client Stan so powerful.
The best part?
We didn’t ask John to make this video. Or anyone from his team.
He’s actually a popular YouTuber, and decided to share a “behind the scenes” look with audience about what it’s like to host an offsite for his employees (and why he felt it was worth all the time and money Stan invested in the trip).
Click to watch the video above and you’ll see what it looks like when a founder goes all-in—not just on skiing or a luxury venue—but on building culture, communicating vision, and helping every employee feel like a co-owner of the company’s success.
From Dorm Room to $30M+ in Revenue… and a 46-Person Offsite
Stan’s founder opens the video with a line that sticks:
"Just a few years ago, it was literally just me coding alone in my dorm room. Now we’re flying our 46-person team to Park City for the week. It’s wild."
The video captures the energy and scale of that growth, but it also highlights the responsibility that comes with it:
"This trip can’t just be for fun—it has to be worth the business’s time and all the money we’re spending."
That honesty is rare and refreshing. And the offsite, which cost over $200,000, becomes a case study in how to make that investment worth it.
Why Spend That Much on a Retreat?
“A lot of people really underestimate the power of human connection.”
That’s the thesis behind the trip.
Throughout the week, John reflects on how scaling from $30M to $100M+ won’t happen because of his own to-do list. It’ll happen because the team is aligned, motivated, and operating with deep ownership.
“I think effective leaders realize their job is to create the context and the mental state in which people are excited to build something great.”
It’s not just about slides and strategy. It’s about belief.
A Look Inside the Offsite Agenda
Here’s how the week played out:
Day 1: Arrival, welcome dinner, cultural grounding
Day 2: Team values session with open discussion and real examples of those values in action
Day 3: Full financial transparency and functional strategies presented by each team lead
Day 4: Team bonding (tubing, skiing) + final strategy session + celebration
Throughout, there’s a focus on intentionality:
“We talked through what ‘ownership’ means. I want my word to be worth its weight in gold. That’s the culture here.”
“We’re here to align on values, understand our financial position, and build the roadmap to hit our 2025 revenue goals.”
“The buy-in you create through culture and shared purpose leads to outsize outcomes—one good idea, one 100x contributor leaning in, that’s how billion-dollar companies are built.”
The ROI of Retreats
At Offsite, we often talk about the Return on Intention. When leaders bring their teams together with clear goals—whether that’s strategic planning, team bonding, culture-building, or all of the above—the results speak for themselves.
Stan’s offsite wasn’t just about ski passes and swag. It was about:
Creating a space for psychological safety
Surfacing and celebrating team values
Clarifying financial strategy and execution plans
Building trust and deepening relationships
By the end of the retreat, even the founder is surprised at how much of the leadership was shared:
“Back in the day, it was just me leading offsites. Now I get to watch my team step up and lead in their own beautiful ways. That’s the most rewarding part.”
Final Reflection
After the final night’s celebration, John steps outside for a quiet moment:
“This whole trip has been about our mission. And our service to that mission. And now I’m more confident than ever that we’re going to build something truly special.”
We couldn’t agree more.
John, if you’re reading this, thank you for choosing Offsite and for documenting the magical week in Park City, Utah with your team! We’re grateful to have been a part of your journey.
And…
If you’re a founder, Chief of Staff, EA, or Head of People wondering if the investment in a retreat is worth it—this is your sign.
When done right, an offsite becomes a launchpad for your team’s next chapter.
Ready to plan your next offsite? We’re here to help.
Learn more at Offsite.com and book a discovery call to start planning your next transformational offsite.
Thanks
Jared
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