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Dent:Explore Maui 2019

December 6 - December 9

Dent:Explore Maui dates are tentative, and we’ll open tickets when we confirm our dates. Last year’s Maui event sold out — we have left the schedule and details for last year’s event below for the time being.


Join a group of Denters for a deep dive and interactive experience that will broaden your perspective and help you explore the frameworks you employ for thinking, decision making, and everyday choices. What are some of the better ways to evaluate risk? What principles do psychologists now understand that will help you avoid common traps in decision making? What are some of the more complete frameworks and analogies for thinking about your career, your business, and your life? Which ones are most useful to you now? As always with Dent, you’ll forge relationships with other creative and entrepreneurial people that will last a lifetime, and you’ll get hands-on input from both your peers and world-class experts in some fascinating fields of work.


We’ll bring together a set of leading experts in unique and different fields of work who are ready to push our perspective on how we think and act. These speakers will lead sessions and workshops throughout the four days of Dent:Explore Maui that will broaden our perspectives and give us new tools to approach our decision making in life. We’ll share the guides here as they are confirmed and added to the schedule.

What to Expect

The Dent community is filled with inspiring and motivated people who are looking to share great experiences together and accomplish big things. Your time in Maui will be personable, actionable, and social. The schedule will provide great opportunities to learn and evaluate new frameworks for thinking and how they can apply to the challenges you are currently facing. Limited to 35 people at most, this experience in Maui will include time spent outside the meeting room. Ka’anapali beach and the nearby areas of Maui offer all kinds of amazing experiences. We’ll enjoy a catamaran cruise, a pub crawl, a magic comedy show, great meals at fantastic restaurants, and a series of games and activities that provide the opportunity for you to forge deep and meaningful relationships with your peers.


Dent:Explore Maui features workshops and adventures on the “Valley Isle”. Your ticket covers conference programming only, exclusive of food and lodging. Discounted lodging at The Sheraton Maui, most meals, and other activities are the responsibility of the attendees unless otherwise noted in the schedule.

Friday, Sep 7th

1:00 PM

Mindsets and Decisions

Sheraton - Kihei Room
Guide: Ellen Leanse

The way we think the world works determines how we experience life and make every decision. Ellen will walk us through two important frameworks: the role of unseen brain functions in shaping perception and interpersonal dynamics, and how a mindset toward growth and learning changes the way we navigate the world.
2:15 PM


2:45 PM

Lessons From Design Thinking

Sheraton - Kihei Room
Guide: Elisa Jagerson

Great design comes from deep and thorough thinking — from the basic function of something on a mechanical level, to how it makes people feel about themselves. In this interactive session, Elisa will share with us different aspects of design thinking, her own approach to "experience engineering" — and how we might apply those methods of thought to other decisions we face in life and work.
3:45 PM


4:15 PM

A Physicist Who Thinks Like an Engineer

Sheraton - Kihei Room
Guide: Laura Ulibarri

Laura Ulibarri is often described as a “physicist who thinks like a engineer.” In this talk, she will describe how the two fields align, how they diverge and how both approaches can be used to problem-solve in both work and personal realms.
5:15 PM

Break to prepare for Dinner

6:30 PM

Welcome Dinner (hosted by Dent)

Various Restaurants
Dinners will be at various restaurants around town.
8:30 PM

Hot Seat Exercise

Sheraton Maui
Getting to know our companions.

Saturday, Sep 8th

8:00 AM

Coffee Meetup

Black Rock Kitchen - Sheraton
A-la-carte breakfast is available on the Hula Girl cruise, or eat beforehand if preferred.
9:30 AM

Catamaran Cruise Departs

Ka'anapali Beach - Leilani’s
Join Denters for a full-day snorkel and/or SCUBA cruise on the “Hula Girl” Catamaran. Cruise along Maui's scenic coastline to premier snorkeling destinations such as Honolua Bay Marine Sanctuary. Knowledgeable captains and crew are marine naturalists who are happy to share information on an informal basis throughout your sailing excursion. Purchase your tickets well in advance, as the cruise does sell out.

You can purchase tickets to the cruise here.

Alternative: for those who get seasick, wait too long to purchase their seats, or simply prefer a different activity -- some Denters will head to the Maui Aquarium for the day.
12:30 PM

Lunch on Hula Girl Cruise

No-host lunch available for purchase on the catamaran.
2:30 PM

Arrival from cruise / Personal Time

Ka'anapali Beach - Leilani’s
6:30 PM


Various Restaurants
No-host dinner. Hawaiian eatery on the Plantation Golf Course offers views from the 19th hole & elegant island fare.

Sunday, September 9th

10:00 AM

Morning Beach Time/Activit(ies)

Snorkel tour of Black Rock option
Golf option
Walking tour Ka'anapali option
11:00 AM

Book Club
Poolside at Sheraton Maui

We’ll grab a couple cabanas poolside at Sheraton Maui to discuss the books people have brought with them to Hawaii. The group will split into two or three conversations depending on size; please plan to share a five minute summary of a book you’ve brought with your or have read recently, and any one key lesson or takeaway from the read.
12:30 PM


Denters find lunch; there are wonderful options for dining up and down Ka’anapali beach south of Black Rock.
3:00pm - 4:00pm


Sheraton - Kihei Room
Guide: Danny Hernandez.

Danny will teach us how to use systematic prediction to make better decisions.

Danny Hernandez found his calling while working as an early data scientist at Twitch (acquired by Amazon in 2014). At Twitch Danny trained hundreds of staff to systematically and reliably think through their most important bets. It's hard to make a dent in the universe without making some big bets. Danny founded Evident to teach people and organizations to deliberately practice that skill. He currently consults for OpenAI, GiveWell, and Open Philanthropy and his work has been published in HBR and the Associated Press.
4:00pm - 5:30pm

Round Tables Conversations (2)

Sheraton - Kihei Room

We’ll split into two smaller groups and host round table discussions that dig into topics raised earlier in the conference, lead by two conversational guides.
6:00 PM

Drive to Dinner

Find your way to dinner in Lahaina.
6:30 PM

Sunset Dinner

Various Restaurants
Dinner at various restaurants. Guests are responsible for their own meals.
9:30 PM

Lahaina Pub Crawl

The group will tour some of Lahaina’s hot spots.

Monday, September 10th

8:00 AM


The Sheraton
9:00 AM

Drive to Maui Makers

9:45 AM

Tour Maui Makers

Maui Makers
Guide: Laura Ulibarri

Maui Makers is a non-profit community workspace that provides access to all kinds of equipment and training to locals working on innovative ideas. Maui Makers President Laura Ulibarri will take us on a tour of the makerspace and the cool stuff being built there.
11:00 PM

Drive to Makawao

On the trail / adventure
11:30 AM

Lunch in Makawao

12:30 PM

Tour Pacific Science Institute

Guide: Garrett Lisi

We’ll join surfer-physicist and TED Speaker Garrett Lisi for a tour of the Pacific Science Institute on Maui. Garrett will show us the grounds and host a small Q&A with Denters about 8 dimensional models of the universe -- or whatever else we want to talk about.
2:00 PM

Drive back to Ka’anapali

Head back to home base and prepare for the evening or get to Lahaina.
5:00 PM


Various Restaurants
No-host dinners near the venue for the evening comedy magic show.
7:30 PM

Warren & Annabelle’s Comedy Magic Show

900 Front Street A202, Lahaina, Maui
In one of Maui’s most elegant and intimate settings, Warren Gibson, highly acclaimed showman and one of the country’s premier sleight-of-hand magicians, treats you to the best “close-up” magic, hilarious comedy and southern hospitality in this beautiful, million-dollar Hawaii venue!

Please note: Attendees wanting to enjoy the show must purchase tickets through the show's website here. - more info can be found below this schedule.
9:00 PM

Return to Ka’anapali

Back in Ka'anapali for the evening.

Tuesday, September 11th

9:00 AM


The Sheraton
10:00 AM

Mental Models for Truth

Sheraton - Kihei Room
Guide: Mark Duncan

In his Dent 2015 talk “lessons of a Consulting Detective,” real-life Sherlock Holmes Mark Duncan gave us a taste of the techniques and secrets he uses to unlock cold cases. On Maui, Mark will delve more deeply into the mental models he uses to get to the truth. One of his central models (which was embraced by Steve Jobs) is the concept of “Shoshin” the Japanese Zen term meaning "beginner's mind.”
12:30 PM

Closing Lunch

Please Note: Dent has not grabbed any “block” of tickets, nor have we reserved any seats in bulk for either the Magic Show or Hula Girl Cruise. All Denters are on their own to make reservations/buy tickets. Both of these activities are prone to selling out, so you should get your tickets purchased now (if you have not already done so.) Magic Show Tickets September 10, 2018, 7:30pm seating Tickets can be purchased here. Important: When you register for the “second seating” (the 7:30pm timing) at Warrenandannabelles.com, do not book dinner there. You just want to do the performance which means you can arrive as late as 8:15pm to see the show. Warrenandannabelles.com has sent a follow up email to some Denters wanting to “confirm your dining plans and appropriate arrival time.” Assuming you are joining all the rest of us at Mala Ocean Tavern, the correct answers are: “eating prior to the show elsewhere” and “8:15pm”. Hula Girl Cruise Reservation September 8, 2018, 9:30am departure If you plan to go on the snorkel/scuba cruise and have not registered, now is the time to do so! These cruises frequently sell out.

Travel Tips and Information

Flying to Maui: Maui’s major airport is in Kahului (airport code of OGG.) There are several airlines who fly from the US mainland directly into OGG. If you can take one of those flights, that would likely be optimal. If not, you’ll probably have to connect in Oahu’s Honolulu (HNL) airport. You may notice there’s a small regional airport in Kapalua that appears to be convenient to West Maui resorts, but only inter-island flights land there, we recommend you fly into Kahului (OGG). Transportation on the Island: While Uber is available on the island, we recommend either renting a car or teaming up with someone who is. At this time of year rental car rates are not prohibitive. The ride from OGG to Kaanapali Beach will take close to an hour, and several of our activities and meals are in areas that are not walkable from the Sheraton. Lodging: Most people will be staying at the Sheraton Maui Resort on Ka‘anapali Beach. This is where the workshop sessions will be held, and we have negotiated a discounted rate on sleeping rooms. It is also the location of “Black Rock” which is the prominent rocky peninsula at the north end of the beach, which has a worldwide reputation as being one of the best snorkeling spots in the world. It is also a short walking distance to a myriad of shops, restaurants, and hotels (should attendees should decide to stay elsewhere.) Making your reservation at the Sheraton Maui Resort: We have negotiated rooms rates that currently run about 18% below the best rates we’ve discovered on Expedia. If you call 808-921-4645 and reference “Dent Explore Maui” you can book rooms for a base rate of $295.00/$260.00 for ocean view/not. Note that these rates do not include Hawaii excise tax of 4.166% or room tax of 10.25%. There is a mandatory daily resort fee of $25.00. Note that parking is $22 per day, $30 for valet parking. The Resort Fee Includes the Following Benefits: * Valet parking on day of arrival (first night only) * Unlimited wireless high-speed internet access in guest rooms, lobby, pool bars, and Hoku Rotunda * Scheduled shuttle service to Westin Maui Resort & Spa, Westin Ka‘anapali Ocean Resort Villas, and historic Lahaina town * Adult Pool Floats * Signature logo Hawaiian tote bag Additional Hotel Benefits: Dent Maui attendees get a ten percent (10%) discount on spa treatments at the Spa at Black Rock and tickets to the “Maui Nui” Luau at the Sheraton.


December 6
December 9
Event Category:


Sheraton Maui Black Rock
2605 Kaanapali Pkwy
Lahaina, HI 96761 United States