Dent Collaboration Weekend: Maui 2025
December 5-7, 2025 Maui, HI
$299 (plus shared costs) for Dent Passport Holders/Dent 2026 Registrants
Our 2025 Maui Collaboration Weekend offers immersive experiences focused on bringing together members of the Dent community in a beautiful, inspiring setting for productive work, meaningful connections, and creative activities. This 2025 event will serve as a change of pace/venue and will replace our traditional annual January San Diego Collaboration Weekend.
Our sleeping room block is limited; this event is currently reserved for paid Passport Members and those who have registered for Dent Santa Fe 2025. Hotel registration details will be included in your registration confirmation email.
Location: Sheraton Maui Resort & Spa
The Sheraton is an oceanfront oasis situated on the most prime expanse of Ka'anapali Beach, where Pu’u Keka’a (Black Rock) meets the Pacific. It offers an unparalleled oceanfront location that has consistently provided Dent groups with both the inspiring natural backdrop and premium amenities that enable collaboration and connection. The resort’s unique position at Black Rock Beach provides direct access to world-class snorkeling and marine life experiences right from the hotel grounds, while offering the kind of elevated hospitality and meeting facilities.
The Sheraton Maui has offered Dent an exceptional group rate of $299 per night for Run of Ocean (ocean view) rooms with a discounted resort fee of just $25 per day, representing significant savings from standard rates. This ocean view rate is a substantial upgrade from previous years when $379 secured only garden view rooms, and the group block includes the standard room extensions of 2-3 additional discounted nights on either side of the core December 5-7, 2025 event dates. A custom reservation link will be provided soon to all registrants.
What to Expect:
Collaborative Work Sessions: Attendees advance personal or professional projects in a supportive environment.
Talks & Workshops: Denter-led sessions and informational presentations.
Curated Dinners: Thoughtfully orchestrated social activities and meals.
Aquatic Activities: Taking advantage of Maui's incredible waters and marine life.
Small Group Dynamics: Intimate atmosphere for deep connections and collaboration.
Talks and Workshops:
Various Denters are offering up talks and workshops, here is what we have confirmed so far:
The Next Competitive Advantage Is How You Facilitate - With Morgan Johnson
This talk will explore the concept of super-facilitators: team members who have abilities to elevate collective performance through integrating team strengths, trust, and collaboration. Drawing on new research in collective intelligence, it shows that group success depends less on individual brilliance and more on the ability to orchestrate the environment for great outcomes. With intentional practice, anyone can develop the skills to turn interactions into trust and teams into superorganisms of problem-solving.
Whether you’re leading a startup, managing creative teams, or simply want to make your collaborations more effective, you’ll leave with practical frameworks for becoming or creating the kind of facilitator who makes everyone better.
Morgan Johnson is Partner and Chief Experience Officer at Experiences For Mankind, a San Diego-based creative agency where she’s spent 17 years rising from intern to agency owner. Her expertise is “bringing simplicity to the complex,” helping clients and teams navigate marketing’s toughest challenges through solid processes, specialized tools, and complete transparency. As a Dent board member since 2019, she’s passionate about the community’s values of authentic connection and caring for your fellow person.
Hands-On with Claude Code: Your New AI Productivity Tool? with Stewart Ugelow
Claude Code has exploded onto the scene in 2025, growing 10x in users since May and now driving over $500 million in annualized revenue for Anthropic. But it's not just for developers—Dan Shipper calls it "the most underrated AI tool for non-technical people." Think of it as "Claude Agent": a super-intelligent AI running locally on your computer that can organize files, enhance images, summarize customer calls, and automate tedious tasks. The challenge? The interface isn't user-friendly and the terminology is wonky. Entrepreneur and management consultant Stewart Ugelow (25+ years of startup experience) will lead a hands-on workshop where you'll learn how the interface works, how to customize it, active prompting techniques, and real-world automation examples. This isn't a demo—it's a working session. Bring your laptop (and a $20 a month paid Claude account) and leave Maui with skills to actually start to use this powerful new tool.
Stewart Ugelow is an entrepreneur and management consultant with over 25 years of startup experience. He's founded multiple ventures including Student.Net Publishing (which raised $9M in equity financing), ShipCycle, and Teach Fishing. As an independent strategy consultant since 2007, he's worked with venture-backed startups across consumer products, ecommerce, health & beauty, and nonprofits, focusing on strategy, business development, and product development
Planned Activities:
Insider Restaurant Experiences: Curated dinners at some of the best “insider” restaurants on the island, featuring locally-sourced cuisine at Denter-preferred venues.
Black Rock Beach Snorkeling & Orientation: For those comfortable with snorkeling, we will assist Denters by faciltating a guided snorkeling and orientation session at the famous Black Rock Beach, providing a first-hand look at Maui’s marine ecosystem in an easily accessible location right at Kaanapali.
“Secret” Turtle Bay Snorkel Excursion: (conditions permitting): 15 minutes north of the Sheraton is Honokeana Cove, here the sea turtles are prolific, offering snorkelers an intimate encounter with Hawaiian green sea turtles in a more secluded, less touristy location. Be advised: this is for experienced snorkelers who are prepared to deal with a rocky entry (no beach).
The final schedule is under development, and sessions are being assembled now (topics to be announced soon) but we anticipate offering this optional activity:
Hula Girl Luxury Catamaran Cruise: A premium snorkeling and scuba excursion aboard Maui’s most luxurious 65x35ft catamaran featuring air conditioning, gourmet food, professional dive instructors, and visits to premier destinations like Honolua Bay Marine Sanctuary.
Other Costs:
The event ticket price includes the Denter-favorite meeting space at the Sheraton – the spacious Kihei Room, which has been reserved for two days and will feature some group catering amenities. All other expenses including dinners, tours, and activities where fees are charged directly by service providers will be the responsibility of individual attendees.
Folks who have not registered for Dent 2026 or are not part of the Dent Passport program may be able to attend for $999 and. based on availability; click the registration link above to join the waitlist.