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Creating Successful Company Offsites — Location Is Everything

In March 2020, Lighter Capital's entire team transitioned from a decade of working in a traditional office in Seattle to embracing the remote-only model. Today, the team is spread across four continents and nine countries and our clients span across the U.S. and Australia. In this ever-evolving landscape of remote and hybrid work, Lighter Capital has actively sought innovative ways to foster team building, inspire creativity, and solidify its goals and strategies.

Among the various initiatives, our semi-annual company offsite retreats and annual client summits stand out as exceptional catalysts for growth and connectivity. Lighter Capital has mastered the art of curating these offsites and summits to perfection.

Seriously, we do these really well.

Why do an offsite retreat?

These retreats offer a unique opportunity to turn off Zoom/slack/email to engage in meaningful face-to-face interactions, building trust, rapport, and a shared sense of purpose. Teams can get a better understanding of each other’s strengths and perspectives, forge deeper connections, and discover shared hobbies or interests. The resulting boost in team cohesion and camaraderie not only enhances productivity and innovation but also cultivates a positive company culture that promotes employee satisfaction and retention, ultimately contributing to the long-term success of the organization.

Where to begin? Location, Location, Location.

While several components go into creating a successful offsite, choosing the right place for a company offsite is crucial. We’ve tried a variety of options: large hotels with conference rooms and shared space, resorts, and boutique hotels.

We do not compromise on the following:

  1. Choose a hotel, resort, or boutique where your team will be the majority of guests. We’ve found sharing a large space with other guests diminishes intimacy and creates a distraction.

  2. Activities on site or nearby are a must. The time spent together should be about fostering connection instead of accomplishing deadlines. We’ll dig into daily schedules, activities, and content in our part 2 blog.

  3. Karaoke. Why? Because it makes everyone step out of their comfort zone — and, really, it’s so much fun. All you need is this mic, speaker, and connection to a screen. Our team was very skeptical at first, but it’s now become something we look forward to at every offsite. But if karaoke is not your thing, find one activity that is a constant with every offsite. It could be trivia, Pictionary, or pickle ball — find a creative outlet that makes sense for your company’s interests.

To date, we’ve had four offsites and two locations stand out as particularly MAGICAL. Not surprisingly, both places are owned by incredibly interesting entrepreneurs who didn’t start out in the hospitality industry.

Doe Bay on Orcas Island

In September, we traveled to Doe Bay Resort & Retreat on Orcas Island — nestled in the picturesque San Juan Islands in Washington. While it required a bit of travel logistics to get there due to planes & ferry rides — the journey only added to the excitement. With stunning views, access to a private beach, and a variety of outdoor activities such as hiking, kayaking, and yoga, our team was able to unwind and reconnect with nature together.

Each person had their own private room within the resort’s cozy cabins and enjoyed delicious meals from their farm-to-table restaurant. We recommend July through mid-September for the best weather. Learn more here.

Doe Bay is owned by Joe and Maureen Brotherton — they fell in love with each other and Orcas when they camped on the west side of the island in the 70s as teenagers. After visiting for decades, they decided to buy it and haven’t looked back. In addition to owning Doe Bay (and Doe Bay Fest), Joe is a Professor of Law and Ethics at the University of Washington, is a Seattle Based Attorney, is a successful entrepreneur across multiple fronts, and was named one of Seattle’s “Most Influential” business leaders.

The Inn at Kulaniapia Falls

In March, our team traveled to Hilo, Hawaii to stay at The Inn at Kulaniapia Falls. Situated on a breathtaking 120-foot waterfall, the Inn's idyllic location offered a range of outdoor activities, including waterfall rappelling, hiking, swimming, snorkeling, and exploring nearby botanical gardens.

Our meetings and meals were enjoyed together on an outside patio overlooking the lush rainforest and cascading waterfalls. It seriously could not have been more beautiful. The town of Hilo and the ocean were a short drive or bike ride away.

The inn can accommodate 17 private rooms and cabins. Due to our team’s size, we rented a couple of Airbnbs nearby, but everyone was able to gather at the Inn.

The Inn is now owned by Christophe Bisciglia, after he saw a Zillow ad that simply read “Waterfall property outside Hilo for sale.” It was 2016, he was ready to say goodbye to Silicon Valley and channel his creative and entrepreneurial energy into something outside tech. Christophe previously worked in big data and cloud computing. He is known for popularizing the programming model MapReduce while working at Google, and co-founding Cloudera.

Want help planning your next offsite?

Connect with our travel planning extraordinaire, Kristi Finley at

Stay tuned for part 2 when we go into daily schedules, recommended team activities, icebreakers, and content ideas.


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