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Years ago, I had the chance to film Brian Sharples right after he launched HomeAway for an online show my best friend and I were producing. At first, I thought I’d just be documenting a clever startup solving vacation rental headaches. But once I started digging into Brian’s story, this wasn’t just another founder story.

This was a guy who had failed big—again and again. I was mesmerized. Not just by his success, but by his perseverance… and his ability to turn failure into fuel.

Every misstep became a strategic advantage. Every scar made him sharper. And that’s the story founders need to hear.

In today’s issue, I share Brian’s winding, wreck-filled road to HomeAway along with:

·       3 storytelling lessons from Brian to make your story unforgettable
·       Why failure might be your greatest founder advantage
·       the video I filmed with Brian right after launching HomeAway

Enjoy this home away from home story …LG

Founder Story: Brian Sharples, HomeAway

Brian Sharples grew up watching his father, an engineer-turned-entrepreneur, trade a steady job for the risks of building his own company. It wasn’t glamorous, but it was enough to lift the family to a better life, and it planted a seed.

By grade school, Brian was already hustling with a lemonade stand and a paper route.

At eighteen, he bought an old boat, turned it into a floating oyster and clam bar, and served seafood and beer to locals. Business boomed until Walter Cronkite, the most trusted man in America, got sick from bad clams and reported the unlicensed venture. The business sank overnight.

Next, Brian tried his hand at a photo business, renting large boats and snapping pictures of sailors. That venture fizzled, too.

Shifting his focus to education, Brian earned a degree in math and economics from Colby College, then an MBA from Stanford. He went on to become a consultant at Bain & Company—but deep down, he knew his path wasn’t advising businesses. It was building one.

That led him to his next big swing. 

Frustrated by the hassle of buying and selling cars in the Bay Area, Brian raised $1 million to create a large-scale, physical used car marketplace at San Francisco’s Candlestick Park. The idea was simple: bring buyers and sellers together for a weekend of deals.

But on opening day, a freak 75-mile-per-hour windstorm tore through the event, shredding tents, collapsing towers onto parked cars, and wiping out the entire $1 million investment in a matter of hours.

Undeterred, Brian launched iMotors, an online used car platform that raised $120 million and reached $25 million in revenue by 1999. But when the dot-com bubble burst, iMotors was brought to its knees. Brian eventually sold the company’s assets to AutoNation for $85 million, salvaging what he could from the wreckage.

Brian relocated to Austin, Texas, where he joined IntelliQuest, a high-tech market research firm. As CEO, he led the company through an IPO and a successful sale, his first substantial win as both an operator and investor.

With newfound time and financial freedom, he and his family traveled extensively, often renting vacation homes instead of staying in hotels.

He loved the space and amenities vacation homes offered, but the booking process was a mess. It was outdated, fragmented, and filled with uncertainty.

Finding and reserving properties meant juggling classified ads, realtors, and clunky websites. Even when you found a promising listing, you had no idea if it was legit, or if you’d show up to a beach shack with no toilet.

Brian dove into the customer journey, speaking with renters and property owners alike. He mapped the market. He studied the competition.

Their mission wasn’t just to aggregate listings—it was to create the largest and most trusted vacation rental marketplace in the world. That meant streamlining the user experience and equipping both owners and renters with professional-grade tools to manage their properties and bookings.

Over the next few years, they raised $405 million in private funding, acquired 17 companies, and scaled the platform to over 640,000 properties in 168 countries.

Six years after launch, HomeAway went public in a $216 million IPO, valued at over $2 billion. Four years later, Expedia acquired the company for $3.9 billion.

Storytelling Lessons: Turn Your Scars Into Superpowers

Brian Sharples’ story is a great example of how failures, frustrations, and fierce belief can be transformed into powerful narratives that rally people, raise capital, and reshape entire industries.

Below are 3 lessons you can learn from Brian’s style to elevate your storytelling:

1. From Frustration to Foundation: How a Pain Point Became a Global Platform

   Before HomeAway existed, booking a vacation rental was a mess, clunky websites, shady listings, and zero trust. Brian experienced this pain firsthand. He turned his frustration into fuel, designing a clean, customer-first solution that resonated with travelers and homeowners alike.

   
   Start with your own pain. What problem are you solving? Build your story around that relatable experience. When founders speak from real frustration, the story hits harder, and the solution feels more credible. 
   

2. Failures Are Fuel: Turn Disasters Into Assets

   Brian went from disaster to disaster, but each failure sharpened Brian’s judgment, expanded his risk radar, and prepared him for success at Intelliquest and laid the foundation for building HomeAway. He doesn’t hide these stories; he highlights them.

   
   Don’t skip the hard parts. Share the wreckage. Talk about the missteps and what they taught you. When founders own their failures, it shows growth, grit, and wisdom. Stories like these build trust when you show what you learned.
   

3. Lead with Conviction & Speak with Heart: 

   Brian doesn’t sell with hype, he speaks with belief. His passion shows in his eyes, his voice, and his actions. He doesn’t shy away from the dark parts of the journey, and he doesn’t pretend to have all the answers. What makes his story powerful is that it feels real.

   
   Be transparent. Be you. Let your values, passions, and even your fears show up in the way you tell your story. Audiences connect with founders who are vulnerable, honest, and committed to something bigger than just profit. 

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Fun Fact: Failure + Story = Success

In a special issue of Nature, researchers from Northwestern and the University of Chicago found that success isn’t just about persistence—it’s about learning from failure. Those who adapt and refine what didn’t work are far more likely to break through.

Brian Sharples didn’t quit after bad clams, windstorms, or the dot-com bust. He evolved—and that resilience became the heart of his story.

Science agrees: reflection, iteration, and honesty aren’t just good storytelling. They’re how you succeed.

Video to Watch: On the Road with iV & Brian

Here is the interview I filmed  with my BFF Ingrid Vanderveldt and Brian just after he launched HomeAway. On the Road with iV-Brian Sharples

This video gives you a front-row seat to Brian’s candor, humor, and raw honesty as he reflects on everything from lemonade stands to the spark that led to HomeAway. It’s a unique look at a founder who leads with authenticity—and turns experience into insight.

A must-watch for any entrepreneur chasing their next big idea.

Storytelling for Entrepreneurs Issue #032 - From Bad Clams to a $3.9B Exit: Brian Sharples' Bumpy Ride to HomeAway...


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