A Rare Jewel of a Vacation in Hawaii This young entrepreneur found success by tapping into an unmet Hawaiian market: upscale vacation services.

By Lindsay Holloway

Opinions expressed by Entrepreneur contributors are their own.

Anne Pawsat-Dressler, 28

HawaiiHideaways, Kula, Hawaii
Projected 2008 sales:
$5.4 million
Description: High-end villa rental agency specializing in upscale concierge services

Aloha spirit: All it took was one vacation in Hawaii for Anne Pawsat-Dressler to know she wanted to move there for good. Initially, though, she had a hard time getting used to the laid-back Hawaiian lifestyle. "Everywhere you turn, it's 'Oh, sorry, that's Hawaii style,'" she says. "I could see there was a real lack of high-end services in Hawaii," especially in travel. Pawsat-Dressler sought to change that by launching Hawaii Hideaways in 2004.

Gold standard: Although Pawsat-Dressler already had a handful of clients through previous travel consulting work, she also faced skeptical homeowners who were hesitant to hand their multimillion-dollar estates over to a 24-year-old. "It was [like], 'Here's the challenge: They already think I don't have what it takes, so I've only got one hour to win them over.'" Before long she built up her inventory of rentals and grew her brand as a leading provider of luxury vacations in Hawaii.

Five stars: With five full-time employees, Hawaii Hideaways provides rental properties and 24-hour concierge services, from massages and personalized birthday cakes to luaus and yacht charters. Pawsat-Dressler says her most bizarre request came from a guest from Hong Kong who wanted to bring his own bed. It's this kind of unparalleled customer service that helped her earn Condé Nast's Villa Rental Specialist award in 2006 and 2007. With word-of-mouth as Hawaii Hideaways' main marketing method, the award is helping boost the company's reputation, which is Pawsat-Dressler's core focus right now.

Follow her lead: Pursue your passion and you can achieve your dreams.

Online Exclusive

What is your secret to success?
Pawsat-Dressler: It's so basic: Answering my phone and always being available and accountable.

What advice would you give other entrepreneurs?
Pawsat-Dressler: Never underestimate the Web. If you have an idea for a business you'd like to start, there's very little overhead related to putting it up on the Web first and seeing what response you get. Do a run-through on the Web, and then tweak your business model after the first trial.

When did you know you'd "made it"?
Pawsat-Dressler: When I got a $110,000 check for my second reservation. I knew that people trusted me with their money and knew I would deliver a good product.

Whatwas the first toy or reward you bought for yourself when you became successful?
Pawsat-Dressler: I bought myself an Audi a month into business.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Business Ideas

70 Small Business Ideas to Start in 2025

We put together a list of the best, most profitable small business ideas for entrepreneurs to pursue in 2025.

Marketing

If You're Using ChatGPT This Way as a Marketer, You're Missing Out on Its Full Potential. Here's How to Maximize Your Results.

The real value of AI isn't in what you ask — it's in how you shape the conversation. Mastering prompt interactions means better content, sharper thinking and fewer generic outputs.

Living

The 3 Lifestyle Habits That Made Me Sharper, Stronger and More Successful

These three simple yet powerful lifestyle changes transformed my productivity, energy and mindset. Here's how you can do the same.

Side Hustle

This Couple Started a Side Hustle to Improve a 'Terribly Made' Bathroom Essential. Now the Business Earns More Than $3 Million a Year.

Michael Fine and Lisa Schulner-Fine launched lifestyle brand Quiet Town in 2016 and have been growing it ever since.

Leadership

Your Employees Need More Than Paychecks and Perks — Here's What They Really Want

In an era where remote and hybrid work arrangements are reshuffling traditional office dynamics, thoughtful, personalized benefits are becoming a powerful differentiator. The bottom line is really simple: If you want to support your employees, address their long-term financial needs.

Living

Inspired by the Masters? Bring Your Work Hustle to the Golf Course with Mind Caddie, Now $99.99.

If the Masters made you realize that your game needs work, check out this performance coaching audio app.