Playing in the Sunshine

There’s The Endless Summer, the movie, which refers to shuffling between the southern and northern hemispheres, spending the entire year playing in the sunshine. And then there’s The Endless Summer, the dream, which is to spend an entire lifetime playing in that sunshine. Wingnut, also known as Robert Weaver, has done a damn fine job of the latter. For the last quarter century, he’s been a regular in lineups in Costa Rica, the Maldives, Hawaii, and other worthy locations. At bars and restaurants adjacent to those lineups, he communicates in shorthand with the waitstaff. Often, his drink lands on his table before he sits down. It’d be disrespectful to both Wingnut and the clients he takes along to call what he does a scam, but to a certain school of surfer, it most certainly is. 

Spawned from the Blackies surf scene of the late 1970s, Wingnut graduated from Newport Harbor High School in 1983. After getting an associate’s degree at Orange Coast College, he headed north to Santa Cruz, where he enrolled at UCSC with a major in political science. Between classes, he surfed Pleasure Point and worked shifts as a busboy at Riva Fish House on the Santa Cruz Wharf alongside a waitress named Janice Barr. Soon, he and Janice became a couple, and have since been married for 29 years.

During Christmas vacation of his first year at UCSC, Wingnut and Janice traveled to Hawaii. The water was balmy. The rolling breakers of Queens were to his liking. He and Janice decided that college could wait. They shipped over Wingnut’s VW bus and shacked up in Waikiki for the next two years. Between surfs, Wingnut worked as a waiter at Bobby McGee’s and as a valet at the Hard Rock Café.

In 1988 they moved back to Santa Cruz and Wingnut returned to UCSC, where he graduated in 1990 with a B.S. in economics. His career aspirations were modest. He hoped to get a job in the surf industry, maybe as a sales rep, possibly as a team manager. He was determined to keep his priorities (i.e., surfing) in order and live the best version of The Endless Summer that he could.

Then came the real Endless Summer, or, more precisely, The Endless Summer II, in which Wingnut was cast as a lead. I remember first seeing it in the theater when it came out in 1994, with Wingnut and co-star Pat O’Connell riding the world’s best breaks, meeting luminaries, having a rip-roarin’ good time. I remember thinking: Those are some lucky motherfuckers.

Now 55 years old, Wingnut lives in the Pleasure Point neighborhood of Santa Cruz with Janice, their 23-year-old son, Cameron, and their dog, Lucky. When he’s not on the road, Wingnut typically wakes at dawn and goes SUP fishing, where he catches white sea bass and halibut. He believes in living simply, though on flights longer than three hours, he now flies business class. 

On a bright Saturday in June, at what the writer T.C. Boyle would call 10 a.m. Western Plague Time, Wingnut and I met in the Point Dume State Beach parking lot to talk. A carpet of blue stretched to the horizon, shimmering and indifferent. Wingnut wore sand-colored shorts, a grey tee, and a red, white, and blue flannel shirt. He’d just taken a billionaire surfing, the first work he’d done in a while. His mood was upbeat.

JB In your own words, Mr. Wingnut, what do you do for work?

RW I’m fortunate enough to have found a career guiding surf trips and coaching people, bringing them into surfing and helping them make the transition from big boards to little boards. Wave choice is the number-one thing that I try to help people with. After that, I like to hand them off to the more accomplished coaches. My normal schedule has me traveling between 150 and 200 days out of the year.

JB What sort of folks do you work with?

RW I work with a very amazing group. This is the most awkward part, right, because I sign NDAs [non-disclosure agreements], so I can’t really talk about who my clients are.

JB How 007 of you.

RW The way it started was there was a guy in New York, David Tashjian; he was the managing director of [investment banking firm] Lazard Frères. His boys were 10 and 12 at the time, and they loved watching The Endless Summer II. And so David got ahold of me through my best friend, Kevin Miske. He said, “Hey, can we go surfing with you? My sons would really like to meet you.” I said, “Well, sure.” I didn’t know if I was going to fly there or they were going to come out here, but over the course of six months, we figured out they’d come out for their spring break. And we went surfing in Newport and Huntington—kind of zoomed around there for a couple of days. And after that, whenever he had friends in the city that wanted to go surfing, he’d say, “Hey, you’ve got to call Wingnut.” So David really started my entire relationship with clients. It was funny because at one point David said, “How much are you going to charge?” And I went, “Well, you’re a friend of Kevin’s friend, I’m not going to charge you anything.” And he said, “You don’t understand how this works. I pay a golf pro. I pay a ski pro. You’re a surf pro. You get paid.” I was like, “What?” Because, I mean, we’re talking 24 years ago, right? So this just didn’t exist. What I do now didn’t exist back then. 

JB Did it ever get tricky? Did you ever think: These are the very people I spent my surfing life trying to get away from?

RW I will say, of the clients that I have now, I would be very comfortable if they were ruling the world. They are so genuinely kind, thoughtful, and proactive in ways that they really don’t want anyone else to know about. They’re not tooting their own horns about the things that they do. I can remember one specific incident where I was trying to get a client to come surfing because the conditions were going to be good all week. This was in Santa Cruz. The client could not come, had other things planned during the day, meetings. I was like, “Have the meetings at high tide. Schedule it for the afternoon. It’s going to be so good this week.” When the client finally did come the following week, I asked, “What was so important that we had to blow the best week we’ve seen in a month?” And he was like, “We were funding the cure for Ebola in Africa.” And I had to be like, “Okay. You missed a good week of surf, but you saved a million lives.” So it’s that kind of stuff where, when you find out about what they’re really doing, it makes it like, “Okay, all I am doing is giving them a little bit of sanity in a world that they deal with that I know nothing about. And if I can give them some saltwater therapy and put a smile on their face, if they have some really tired arms at the end of the day, I think that’s my part for the planet.” Because I’m helping those people who are really going to help the planet.

JB Did you have career aspirations other than what you’re doing now?

RW I graduated college in June 1990, married Janice in October, and my plan was to go to the ASR [Action Sports Retailer] trade show in San Diego. I had one of the old Mac SEs, right? And so I took a Hobie business card and Stewart Surfboards business card, got the fonts on the computer right, and put my name on the cards. Then I went to Kinko’s and made my own business cards by taping my name over Bill Stewart’s name so that I could get a badge to get into the show. So I was going to lie my way into ASR with my two different badges, depending on which booth I was going to, because I was going to try and get a job. But ASR was in February. In January, Bruce Brown called. So that changed everything.

JB The Endless Summer II obviously put you on a new course.

RW Yeah. Because there was no way to make a living as a longboarder in the early 90s. I was getting free wetsuits and free surfboards, and I thought I’d hit the top of the market. I mean, if your passion doesn’t cost you any capital, you totally win. I was way ahead. I could work. I’ve always liked to work. I worked in restaurants. I could do anything. I’m not scared of the work. And then, all of a sudden, there were sponsorship opportunities. For ten years after The Endless Summer II, I was drawing a good paycheck from O’Neill. I figured out how to work for O’Neill Europe, and I created the Surf Academy program for them. So I spent seven years taking ten surfers from the United States to do a mobile surf school—one week in each country. We’d set up a big camp, 50 kids a day, and then we’d move to the next country. We had an Airstream motorhome that we traveled in. We had an 18-wheeler with 50 surfboards, 150 wetsuits. It was great. 

If I can give them some saltwater therapy and put a smile on their face, if they have some really tired arms at the end of the day, I think that’s my part for the planet. Because I’m helping those people who are really going to help the planet.

JB What’s the secret to your success as a surf coach? 

RW It’s operating with integrity. We don’t advertise, and I don’t have a website. It’s all word of mouth. Usually, it’s one of my clients. And I have to call them clients, but they’re my friends. I mean, it’s all repeat business. I’ve known these families for ten or 15 years now. I bring them into my home and introduce them to my friends. And I wouldn’t bring in anybody that I did not truly trust and love into these relationships, and so that’s how it continues. It’s like good longboarding: You want to make it look effortless. You don’t want to make it look like you’re scrambling around to try to get something done. I guess it comes from when I used to wait tables. I want to make sure they have as good a time as possible during their meal.  

JB What do you like most about Santa Cruz?

RW It still feels like a small town. I liked longboarding because it came from that era, the 1950s and 60s, before the [John F.] Kennedy assassination, when it seemed like there were unlimited possibilities. Everything in the world was good. We came out of World War II. We were going in the right direction. There was just that happiness. And the guys that were the surfers, after what they’d experienced, they just didn’t want to go into the real world. And Santa Cruz still has that bohemian, “maybe we can do this without doing the real world” stuff. The people that can make it work in Santa Cruz are willing to put up with less of an income and smaller houses for a certain quality of life. 

JB Have you ever second-guessed your choices as a surfer, betting the farm on this thing that can be frustrating in midlife and beyond? 

RW I think one of the nicest things about having chosen the longboard path, or having it choose me, is that I think you can do it at a high level to a very advanced age. I mean, our pristine conditions are shoulder-high and within 30 yards of dry sand. I’m not looking for the best reef-pass barrel at 55 years old. So I’m happy with how that has found me and how I’ve found it. There was a period when things got rough. It was after The Endless Summer II. I got MS, and there was that whole thing of, “What’s my life going to be from this point forward? Am I going to be able to ever catch a wave with my son?” He was just about 1 year old when I was diagnosed. But the first year went by, and I was okay. Then, after year three, I was fine. Year five? It was even better. I realized, even if it stops, how lucky I was to have done everything I had done up until that point. Because of Bruce taking me around the world to surf all the marquee spots—I got G-Land, I got Jeffreys Bay, Cloudbreak—I got to do all those things with some of the greatest surfers of all time. So now I’m like, “Okay, if this is the other shoe, I was luckier than I ever thought I would have been.” Remember, I was stoked out of my mind that my surfboards were free and I didn’t have to pay for a wetsuit. Obviously I’m super lucky now that I’m healthy and have no concerns like that. So that also gives me a level of acceptance when I’m out in a lineup. And usually, my clients rarely will be the one to get the A-plus set wave. So the kings in the water are still going to get theirs, and when a good B-plus wave comes, they don’t mind when my kid spins around and goes. It’s finding that balance. I’ve been really lucky. Like Bruce said, “You just make your own luck.” But I like to share my luck with everyone.

Illustration by Adams Carvalho.