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

●      barry@leadingsteep.com