How This Leader Disrupted the Massive Travel Market

On Oct 3, 2023

Opinions expressed by Entrepreneur contributors are their own.

For this Leadership Lessons episode, I was excited to talk to a fellow life-long entrepreneur who is transforming the way people take vacations. Over the past two decades, Brent Handler — co-founder and CEO of Inspirato, the world’s first luxury travel subscription brand — has pioneered the industry. Under Handler’s leadership, the company established itself as a leading luxury hospitality company that provides access to a portfolio of luxury vacation homes and other vacation options, including an innovative subscription model.

Here are 10 valuable lessons this driven leader shared with me during our conversation.

1. Build your business on something you care about

“Go be interested in whatever you’re going to be interested in, and be obsessed,” Handler advises others who want to be entrepreneurs.

2. Find a massive market and attack it with innovation

Travel has always been and will continue to be a massive market. Handler co-founded Exclusive Resorts and served as its president from 2002 to 2009. There, he set the standard for the burgeoning destination club industry by delivering tens of thousands of vacations and amassing more than $1 billion in real estate assets.

3. Delight your customers

In 2010 — convinced he could improve on the model he helped establish — Handler co-founded Inspirato to provide sophisticated travelers access to a collection of luxury vacation homes, five-star hotel and resort partners, and custom travel experiences. Sophisticated travelers get personalized service without the six-figure fees previously standard in the industry.

4. Consider an opaque business model that isn’t a 1:1 cash transaction

Inspirato uses a system of points that can be used for reserving specific destinations relative to demand.

5. Slow down and diversify your wins

Handler says losses will come and go, so it’s best not to be impulsive and blow all the money you’ve just made as an entrepreneur on one big thing. Set the stage for big dreams by diversifying any early wins.

6. Nobody wants to work with a bully

In his 30s, Handler admits that his dogmatic approach as an entrepreneur caused personal friction; his closest confidants told him people thought he was a bully. You need to listen to people, not force your way through.

7. See some of the world during your career

Handler told me he regrets staying close to home during his early life and career, so he has encouraged his kids to plant career seeds away from home.

8. Balance the right speed with the right level of control

Most people get upset at work over one of two things: consensus or bureaucracy. The same person can complain about both simultaneously, even if those impulses are contrary. As CEO, you need to find a way to balance both to compensate for this.

9. “Hungry people fight over food”

Stay scrappy if you can. You’ll do better when you have to make more with less.

10. Gifting a memorable experience to high-performing employees can resonate more than a cash bonus

Handler’s company has an “Inspirato for Business” wing designed to allow employers to share high-value packages that employees will likely remember much longer than a few thousand extra dollars in their bank account.

For more from my hour with Handler, watch the entire webinar here. The growing collection of episodes from our series gives readers access to the best practices of successful CEOs from over 30 of the biggest brands, including Heineken, Headspace, Zoom, Chipotle, Warby Parker, Wayfair and Redfin, to name a few.