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Meet Rick Rupp of WayPoint Sailing

Today we’d like to introduce you to Rick Rupp.

Rick, please share your story with us. How did you get to where you are today?
You have to leave the dock to start any voyage. The same is true for any business venture. The surprising start to my sailing company is that I shoved off from the dock without even having a boat! My company started with a daring promise I made to a CEO in Irvine. He called me for Executive Coaching, but in our first meeting, he asked for an outdoor team building experience for his senior executive team instead. When he said that he sailed with a previous team in Australia, I took a deep breath inside and offered to take his team sailing. What he didn’t know is that I didn’t have a boat or a sailing business! All I did know is there are thousands of boats in Southern California marinas. I simply combined that knowledge with my philosophy in life, “Where there’s a will–there’s a way” (I also added a prayer). Within 48 hours I had a 70′ sloop secured for his team. Within two weeks I was sailing out of Newport Harbor with his team and sailing into a new business. WayPoint Sailing started that day on the ocean. As we returned to the dock, I couldn’t wait to take out other teams for a day at sea.

Great, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
Sailing is affected by wind and sea conditions just as business is affected by marketplace conditions. While my company has had mostly smooth sailing, other times have hit the doldrums when the economic wind died. The Great Recession was one of those times. Our events are on the higher end of corporate retreat and team building budgets, so during lean times, companies reduce these expenditures. But as usual, winds eventually pick up again and senior executive teams and other teams are getting back on board for some unforgettable sails at sea.

Alright – so let’s talk business. Tell us about WayPoint Sailing – what should we know?
WayPoint Sailing puts new wind in team’s sails. Nothing spells teamwork, camaraderie and adventure better than sailing a boat together at sea. A day on the ocean clears the mind and bonds people together in a very special way. My objective is not only to offer a great retreat for teams but for them to apply what they learn back to the workplace. My best reward is to hear follow up reports after their sails about noticeable improvements in communication and cooperation. Another joy of mine is to introduce people to sailing who have never sailed before. They not only love being out on the ocean, but are also surprised at how fast they learn to sail. After the first hour of training at sea, teams learn how to steer and tack the boat all by themselves (the Coast Guard licensed skipper on each boat steps back to coach and navigate). I love to see the boost of confidence in teams as they learn a new skill. Most of all, I love to see the big smiles behind the wheel of the boat, as each person experiences being the captain of their own ship.

WayPoint Sailing is the only sailing company in Southern California that offers sails on every kind of sailboat, from 36′ cruising yachts to America’s Cup racing boats to 110′ Brigantine tall ships. We offer a broad selection of sails for groups as small as five or for larger groups up to 80. We also operate out of five marinas from Marina Del Rey down to San Diego, so we are conveniently located to businesses throughout So Cal. Besides afternoon sails and races, we also offer two to four day sailing retreats to Catalina Island, where guests can really get away from it all at Two Harbors or Avalon. Teams come back from their island retreat refreshed and renewed with great memories together.

WayPoint Sailng seeks to exceed our client’s expectations. Attention to detail and customer service is our number one goal. Our events are designed for our client’s maximum ease, from boarding the boats in the marina to arranging their after-sail trophy presentation at happy hour. Catalina sailing retreats with included island lodging are turnkey events. Teams have options for overnight stays in a rustic craftsman hunting lodge in quiet Two Harbors or in luxury villas in the quaint village of Avalon. Or teams can visit both places with a helicopter transit. We can also helicopter teams from out of state directly back to an airport of their choice.

For the ultimate sailboat racing event in California, WayPoint Sailing now offers teams their own America’s Cup race! This rare opportunity offers teams to race against each other on the famous Stars and Stripes boat against the Italian challenger boat Il Moro. For the truly ultimate race, we can also include the original skippers of these two AC boats with your teams. World famous skippers Dennis Conner and Paul Cayard can also helm your boats. A sail on these beautiful and fast boats along with the personal stories of these sailing legends is arguably the finest executive retreat anywhere.

WayPoint Sailing loves to put new wind in every team’s sails. We sail CEO’s from Young Presidents Organization (YPO), senior executive teams from Fortune 500 companies, to any team from any size company. With sunshine year round, our boats are waiting to take out teams any time of year.

Is there a characteristic or quality that you feel is essential to success?
Persistence is the key to stay on course to any goal. I gain valuable lessons every time I go out to sea. One key quality I’ve learned in sailing and in life is the necessity and the reward of persistence. To never give up. And even if your boat is in last place — to stay in the race. I like what Dennis Conner, a living legend in the world of sailboat racing, once told me. After losing a recent America’s Cup race, he told me that he didn’t lose. That may sound like denial, but he meant it. He told me that he doesn’t lose races, he only learns new lessons to use in his next race. He always wins. Defeats in life don’t need to defeat us. Our attitude always has a choice. Persistence helps us to keep sailing through good seas and bad, through the wins and the losses. Dennis is right. We can win even from our losses in life.


  • Call for a quote on the various boat options and retreats.

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Image Credit:

Photos by Rick Rupp, America’s Cup photo courtesy of Lynn Hanna, Catalina aerial photo courtesy of Santa Catalina Island Company.

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