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Leading Steep - Adventure Travel for the Private Jet Set: Cari Gray

Adventure Travel for the Private Jet Set: Cari Gray

02/19/21 • 53 min

Leading Steep

Leading Steep: Cari Gray

In this episode, Barry sits down with Cari Gray of Gray & Co. After having been an adventure guide and business leader for 14 years at Butterfield & Robinson, Cari decided to branch out and establish her own boutique travel agency in 2009. Today, Cari crafts private trips for the uber-wealthy, and the company itself won the #1 Operator in the 2016 Travel & Leisure World's Best Award.

In this conversation, Cari’s not going to be sharing any names, but she will be pulling back the curtain on the ins-and-outs of running her widely lauded adventure venture.

Cari shares her thoughts on how empathy and humility play key roles in guide ethos and how she put together a team of guides who embody these traits.

Gray & Co. is known for crafting “unscripted” adventures for discretionary clients. Cari explains how choice and flexibility are factored into each and every trip her team puts together.

Finally, Cari speaks on the traits that separate stellar guides from everyone else.

Here’s a glimpse of what you’ll learn:

● [3:32] Cari’s early days as a guide in her 20s

● [9:10] The benefits of allowing for moments of serendipity as a guide

● [11:40] Cari’s favorite experiences during her first year of guiding in France

● [14:20] What guide ethos means to Cari

● [17:20] How Gray & Co. came to be

● [22:30] How Cari finds her guides

● [25:03] Why great guides are like great wait staff

● [29:45] Crafting “unscripted” adventures for discretionary clients

● [33:45] Putting together multigenerational active trips

● [38:30] Current travel hotspots for Cari’s ultra-high-net-worth clients

● [48:16] The importance of stamina, resourcefulness, and teamplay for any guide

Key Quotes by Cari:

● “The key to guiding, whether with friends or business colleagues, is managing expectations and giving people a really clear picture of how the day is going to unfold. Give people control of some of the variables, but make sure that nothing is formulaic and that there is always that dramatic moment—arriving at just the right time for the sunset or coming across that amazing farmer that was willing to let us taste the grapes. Some serendipity layered on top is always a good addition.”

● “Oftentimes, the things that make the biggest difference to [guests] are not the things you can just buy. It’s the wisdom and the experience and the forethought of what might please these people and then putting all the pieces together to make it happen.”

● “‘Slow down to see the world’ is such a timeless slogan and all the more important now after COVID where we all have a renewed appreciation for the smallest details, a lot of which we’ve been deprived of, whether it’s the perfect bowl of pasta in Italy or the incredible tapas in Spain.”

Resources Mentioned:

Gray & Co.

The Ready State

Leading Steep

Leading Steep Fireside on Facebook

[email protected]

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Leading Steep: Cari Gray

In this episode, Barry sits down with Cari Gray of Gray & Co. After having been an adventure guide and business leader for 14 years at Butterfield & Robinson, Cari decided to branch out and establish her own boutique travel agency in 2009. Today, Cari crafts private trips for the uber-wealthy, and the company itself won the #1 Operator in the 2016 Travel & Leisure World's Best Award.

In this conversation, Cari’s not going to be sharing any names, but she will be pulling back the curtain on the ins-and-outs of running her widely lauded adventure venture.

Cari shares her thoughts on how empathy and humility play key roles in guide ethos and how she put together a team of guides who embody these traits.

Gray & Co. is known for crafting “unscripted” adventures for discretionary clients. Cari explains how choice and flexibility are factored into each and every trip her team puts together.

Finally, Cari speaks on the traits that separate stellar guides from everyone else.

Here’s a glimpse of what you’ll learn:

● [3:32] Cari’s early days as a guide in her 20s

● [9:10] The benefits of allowing for moments of serendipity as a guide

● [11:40] Cari’s favorite experiences during her first year of guiding in France

● [14:20] What guide ethos means to Cari

● [17:20] How Gray & Co. came to be

● [22:30] How Cari finds her guides

● [25:03] Why great guides are like great wait staff

● [29:45] Crafting “unscripted” adventures for discretionary clients

● [33:45] Putting together multigenerational active trips

● [38:30] Current travel hotspots for Cari’s ultra-high-net-worth clients

● [48:16] The importance of stamina, resourcefulness, and teamplay for any guide

Key Quotes by Cari:

● “The key to guiding, whether with friends or business colleagues, is managing expectations and giving people a really clear picture of how the day is going to unfold. Give people control of some of the variables, but make sure that nothing is formulaic and that there is always that dramatic moment—arriving at just the right time for the sunset or coming across that amazing farmer that was willing to let us taste the grapes. Some serendipity layered on top is always a good addition.”

● “Oftentimes, the things that make the biggest difference to [guests] are not the things you can just buy. It’s the wisdom and the experience and the forethought of what might please these people and then putting all the pieces together to make it happen.”

● “‘Slow down to see the world’ is such a timeless slogan and all the more important now after COVID where we all have a renewed appreciation for the smallest details, a lot of which we’ve been deprived of, whether it’s the perfect bowl of pasta in Italy or the incredible tapas in Spain.”

Resources Mentioned:

Gray & Co.

The Ready State

Leading Steep

Leading Steep Fireside on Facebook

[email protected]

Previous Episode

undefined - Solo: Let's Catch Up

Solo: Let's Catch Up

In this episode, Barry shares a quick update on Leading Steep and how to reach out and participate, a recap on recent shows, a preview on future shows, thoughts on leadership and kids, and some very important acknowledgements.

Here’s a glimpse of what you’ll learn:

● [0:22] Why a solo episode?

● [2:35] How to contact Barry and join Leading Steep Fireside Facebook

● [3:25] On feedback and leadership

● [3:40] Recapping episodes with Zach Collier, Richard Bangs, and Jim Coffey

● [5:45] Jim Coffey in Ty Smith’s own words

● [7:14] An introduction to Barry’s nonprofit, Junior Guides and youth leadership

● [8:31] Previews of upcoming guests on the show

● [9:54] Acknowledgements

● [10:40] Closing thoughts

Key Quotes by Barry:

● “Great leaders courageously deliver feedback with love in their hearts. Often, the harder the feedback is to deliver, the more impactful it is to hear.”

● “If you’re genuinely interested in people, it goes a long way towards being an effective leader.”

● “Team leaders are multipliers: They put others in front of themselves.”

● “Adventure guides have a great capacity for calm in a storm that any leader can learn from.”

● “Even a small, seemingly insignificant interaction can change your business or change your life. You never know who you’re speaking to or what kind of impact you may have for them or they for you.”

● “As a leader, one of the measures of your success will certainly be the legacy of the leaders you helped build and nurture.”

● “Young people—young leaders—need to use their voice to change the world.”

● “The best guides I know also happen to be the most humble. Aspire to the notion I call ‘humble brilliance’.”

Resources Mentioned:

[email protected]

Leading Steep Fireside Facebook Group

Junior Guides

Next Episode

undefined - Charisma, Color, and the Birds of Borneo: Susan Myers

Charisma, Color, and the Birds of Borneo: Susan Myers

In this episode, Barry sits down with Susan Myers of WINGS Birding Tours Worldwide. She has been birding, traveling, and leading tours in Asia for over thirty years, and has written dozens of papers and articles on ornithology and general ecology in a variety of respected magazines, scientific journals, and books.

Susan is the author of the Field Guide to the Birds of Borneo, published in 2016, and has recently finished a general guide to the wildlife of Southeast Asia.

Listen in as Susan shares her experience and knowledge of the natural world. Her deep affection for and appreciation for Asia and its wildlife is palpable in today’s conversation.

She dives deep into how she conducts a typical birding tour in Asia and her personal thoughts on what makes a great guide and leader.

Susan touches on her decades-long career as a naturalist, must-see birds in Asia and the American Northwest, and her favorite places to travel.

Finally, Susan shares what she is most looking forward to when she can jump back into the field post-COVID.

Here’s a glimpse of what you’ll learn:

● [2:57] How Susan became a naturalist and got started guiding bird watch tours

● [6:46] Susan’s favorite destination in Asia

● [8:55] Susan takes us through one of her typical tours

● [12:27] How many birds you can expect to see during one of Susan’s tours in Borneo

● [15:02] Where Susan finds inspiration as a leader

● [16:31] Susan speaks on the camaraderie among the guides at WINGS

● [17:07] The unique intimacy of a birding tour

● [22:21] How many birds has Susan seen in her lifetime?

● [24:59] Documenting birds on research trips

● [27:02] Possible reasons for the huge decline in migratory birds in the past few months

● [29:05] Susan’s favorite stories from one of her trips

● [31:17] Susan’s go-to places in Japan

● [32:23] Tips for amateur bird watchers

● [34:22] Hard-to-find birds in the U.S.

● [37:12] What Susan has been working on ever since the pandemic halted her tours

● [39:44] What Susan misses about leading birding tours

Key Quotes by Susan:

● “One of the things you’ve got to know about birding is that the mornings are really important. That old adage really is true: ‘The early bird catches the worm.’ In this case, ‘The early birder catches the bird.’”

● “Birding requires patience, full stop, whether you’re talking about the birds or other birders. It should be mutual—hopefully the clients are patient with me because sometimes it’s frustrating when you can’t find the bird you’re looking to show them.”

● “The most important thing for people who want to come on a birding tour is to have a good pair of binoculars. Very occasionally, we’ve had people come on tours with a cheap pair of binoculars. It’s a bit crazy because you’re spending a lot of money on this tour but you’re not spending money on the equipment you need to enjoy the trip. You wouldn’t go snorkeling without a mask; you don’t go birding without binoculars.”

● “One of the blessings of being a naturalist is that you will never be bored. Not in your whole life will you ever be bored. It doesn’t matter where you are; there will be some sort of critter that is going to give you hours of fascination and keep you busy.”

Links:
Wings Bird Tours
Susan Myers Profile
Susan's Links
Birds of Borneo - Susan Myers
eBird - Cornell University
Waxwings (Songs and photos)
Sounds of the Bornean Jungle

Our sponsor:
The Ready State

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