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Jeff Stober
The Pursuit of Doing Good

001 Jeff Stober
  • Words Ken Baron
  • Images Emily Andrews

By supporting local artists and artisans, this high-minded hotelier has transformed creative neighborhoods into global ports of call.

Though he is renowned for his exacting taste and his round-the-clock drive to build habitats that inspire both creatives and guests equally, Jeff Stober seems remarkably at ease these days. With a smile that is almost infectious, he sits before us, full of cheer and energy, quick to pronounce what could be taken as both a personal philosophy and corporate mission statement for the Drake brand he has so artfully created: “We build neighborhood hotels as much for locals as for travelers, with the understanding that there is a curious cultural seeker in everyone.”


It might seem odd that a man who made his first fortune in the IT business is now seen, across Toronto and beyond, as a champion of arts-focused hospitality projects. But the Montreal-born Stober, who started an international IT recruitment firm in 1981 and then rode the early technology wave, possesses an intellectual outlook on life that could best be described as a moveable feast. When asked where he went to school, the Western Ontario University alumnus says, “I am still being educated!”

003 Drake Devonshire Chair
002 Drake Devonshire Minibar Sign
004 Drake Devonshire Jeff Stober Photoautomat

“I always ask myself, ‘Why will my guests feel more enriched, more empowered?”

Jeff Stober

Your hotels are awash in art, music, culture, and inspiration. They seem almost to be broad canvases upon which you paint your worlds. Where did your vision of hospitality come from?

When I was growing up in the 1960s, my family would go on summer vacations to Cape Cod and Maine, and we would stay in roadside motor inns. I was instantly fascinated by these communities of strangers, all congregated under one roof. The swimming pools. The neon signs. The housekeeping service. It was so glam! I loved the romance and history and overall emotional appeal of hotels. With the Drake properties, I’ve built upon this sense of a community-come-together. I believe it’s vitally important to have your own DNA, the thing that defines you. We have a deeply rooted Drake style guide that covers materiality to the point where one knows instantly that he or she is in a Drake property. We love a collision of culture, the irony of an intersection between high and low, timeless and contemporary, rural and urban. It has to be authentic and come from a deeply rooted place. At the end of the day, it's all about engaging with our expansive ecosystem and myriad stakeholders, from musicians and artisans to guests and locals. We always look long-term, commit ourselves to being good neighbors, and treasure the opportunity of creating highly unique hospitality experiences.

005 Drake Devonshire Cafe
006 Drake Devonshire Hotel Sign

So after you sold your IT business, you made the seamless transition to hospitality?

Oh no. First, I did the proverbial global travel adventure, which included extended stopovers in Southeast and Central Asia. When I returned, I was itching to do something more organic, neighborhood-focused, and art- and culture-inspired.

The West Queen West neighborhood of Toronto was filled with galleries and artists. My guiding notion was, and still is, “follow the artist!” as they have the best taste and are bonafide social historians of our generation. I am inspired by deeply pedigreed hotels that have fostered heartfelt relationships with artists. I am also a big fan of older architecture. Montreal, where I’m from, has centuries-old buildings that inspired me. Thus, we are very excited to work with historic buildings. The opportunity to reimagine or repurpose has always held tremendous appeal for me. Preserving and improving what’s already there is an opportunity to become deeply rooted in and a part of the existing community.

008 Drake Devonshire Hotelbed
007 Drake Devonshire Bread
009 Drake Devonshire Come Again

You seem as much a man on a mission as a hotelier. Would you agree?

I think before you embark on a project such as a hotel you need to understand your value proposition, what you are bringing to the world. I always ask myself, “Why will my guests feel more enriched, more empowered as a result of staying at or hanging out in one of our properties?” Having established that art, culture, and curated experiences will be at the core of what is on offer, we commit to opening hearts and minds through our timeless and inclusive vibe. We always focus on culture, community, and hospitality. That is the Drake brand and it is bigger than any of our hotel’s physical footprint.

Do you think your business approach is unique today?

I think companies serve an important social purpose. The ones that don’t understand their social role and only see themselves as moneymaking businesses will fail. One needs to have a moral compass. The upshot: A business will probably do really well by doing good. We are deeply mindful of our responsibilities. We support our communities. We invest in our neighborhoods and collaborate with local artisans and artists, thus creating a deeper meaning.

011 Drake Devonshire Jeff Stober Street
010 Drake Devonshire Photoautomat
012 Drake Devonshire Street Art

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