How Cali Roots has grown into the world’s largest reggae-rock festival in just five years.

Jeff Monser had never organized a music event before California Roots Music and Arts Festival. He hadn’t put on an open mic night or a simple concert, let alone a full-day festival. The Santa Cruz-based artist/screen printing shop owner’s only experience in the entertainment biz came as a vendor selling California Roots Clothing. He weaseled his way into dozens of like-minded gatherings across California – including Santa Barbara’s West Beach Music and Arts Festival – to peddle T-shirts with his original artwork.

But Monser’s love affair with “the ambiance, the mellow and chill people” encountered at these festivals led to a moment of clarity in 2008: He wanted to put on his own. Research led Monser to the reggae-rock genre, which carries a fanbase with Grateful Dead-like followings.

Still, going from T-shirt salesman to the mind behind the largest reggae-rock festival in the world – drawing tens of thousands to see A-list talent like Ziggy Marley, 311 and Steel Pulse this Memorial Day weekend – is like jumping from piano recitals at the YMCA to center stage at Carnegie Hall.

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Monser had a plan: He wanted Cali Roots to be a big party. Which, if you think about it, isn’t much of a plan.

His big party at the Monterey County Fairgrounds in May 2010 brought more than 15 bands, including The Dirty Heads, Tribal Seeds and Top Shelf. He realized midway through the daylong inaugural event that a party was actually a lot of hard work – 1,700 people can do that to you.

“I’ll be honest, I didn’t know what I was doing in the beginning,” Monser says. “There was no master plan.”

With no backing beyond a quickly-spent $4,000 sponsorship from Kona Brewing Co. and a product sponsorship from Monster Energy, he had to put up most of the cash himself. Every penny he made from his screen printing business went to the festival. He took a second full-time job as a screen printer for Specialized Bicycles to ensure bills were paid and his family (Monser’s son Parker is now 2 years old) could make it to the next paycheck. His workday began at 5:30am, Monday through Friday. He had weekends to plan the festival.

Monser saw Cali Roots as an investment for his family’s future – albeit an unorthodox investment, with financial risks at every turn.

“After people see how good the fest is this year and spread the word, a few years down the road, it could turn into a three-day festival on Memorial Day weekend every year,” he told theWeekly in May 2010, a week before its debut.

Everybody – every professional organizer of Brews, Blues and Bacon and Monterey Music Summit shows – says things like this. (First annual! We’ll start small and go big!) Even established events with long tenures, like the now-defunct Monterey Bay Blues Festival and Monterey Bay ReggaeFest, often operate at a loss and struggle to pay performers. The difference here? Monser delivered – and is delivering – on all fronts.

Monser had attended festivals all over California, like the Sonoma County Harmony Festival and the Cypress Hill Smokeout Festival. But it was the West Beach Music fest in Santa Barbara that lured him in with its reggae-rock lineup featuring several Cali Roots regulars, including SOJA, Iration, Zion I and Passafire.

“It’s an easy genre to want to work with because people are always in the best mood,” Monser says.

Monser loosely based Cali Roots on his experience at West Beach Music & Arts Festival, which has since called it quits. It was identifying the hot genre as an opportunity that made all the difference.

“Monser knew [reggae-rock] was a movement that was happening and would become something big,” says festival publicist/artist-media liaison Tanya Moore. “He was right.”

Following its sophomore year, which drew 2,500 and expanded into a two-day event, year number three solidified Cali Roots as a bonafide reggae-rock happening. With additional space (max capacity went from 3,000 per day to 8,000) at the Fairgrounds to build a large main stage, the festival was able to bring Pepper and SOJA, its two biggest headliners yet. Attendance skyrocketed to 12,500.

There’s an adage that a leader’s smartest move is hiring smarter employees. It applied to Monser. Before the blast-off year in 2012, Dan Sheehan, CEO of artist management, booking, marketing and promotion company Vibes Entertainment Group, was brought on as a co-producer, marketer and talent buyer along with Moore, who began PR six months out, deluging radio and television partners, magazines and every other type of media outlet in between.

There are also the loyal volunteer street teams, mostly comprised of unemployed musicians and music festival lifers, that have been instrumental in spreading the word about Cali Roots year-round and countrywide. These special breeds of fans, whose passion can be traced back to the days of ballroom acid tests in San Francisco, have been flooding Facebook, Instagram, Tumblr and Twitter with everything Cali Roots. Monser recently came across a Facebook post of a photo of a Cali Roots flyer in Denver, Colo.

Last year, Cali Roots’ impressive evolution continued, due in large part to the addition of a third day. In addition to Pepper and SOJA returning, Matisyahu and Slightly Stoopid made Roots debuts. The sold-out crowd of 23,500 made it the biggest year yet. (By comparison, in 18 years, Monterey Bay Reggaefest peaked at around 15,000 attendees.) The 2013 installment also marked a Cali Roots East Coast expansion, with the October debut of California Roots: The Carolina Sessions, which brought out 4,500 concertgoers for a full day of Signal Fire, Fortunate Youth, Natural Vibrations, Fear Nuttin’ Band and Mike Pinto, in Wilmington, N.C.

Monser circles back to the importance of delivering the big-name artists to draw such crowds. The key to getting them, he says, is going above and beyond what they ask for. He feted them with truffle and parmesan tater tots, Sierra Nevada Pale Ale chili in bread bowls and handrolled musabi sushi. A unique backstage experience includes separate dressing rooms for all the performers – if they want privacy – and a communal living room area with plants and comfy couches. Upscale lodging completes the equation.

“We want bands to enjoy themselves and want to come back,” Monser says. “Bands who previously played Cali Roots turn down shows this weekend just to be a part of it.”

This year, which had only a few hundred Friday single-day passes left at press time, is another monumental year for Cali Roots: More than 30,000 are expected to attend and for the first time in the event’s short but fruitful history, the Fairgrounds is opening up the historic stage in the main arena.

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Jimi Hendrix, Billie Holiday, Bob Dylan, The Clash, Miles Davis, Peter Tosh, The Who, The Grateful Dead, Thelonious Monk and Simon and Garfunkel have all performed the main stage arena at the Fairgrounds, which just got a new layer of grass. For roots rockers, Steel Pulse enjoys the same kind of renown.

It’s inevitable that many, if not all, of Cali Roots’ 40 performers have been influenced in some way by Steel Pulse  – playing 7:50pm Friday – and its political-minded reggae, which erupted alongside London’s punk scene in the mid-’70s. But anarchy in the U.K. wasn’t the catalyst that inspired the outfit’s activist mentality.

Frontman/founding member David Hinds recalls his first trip to Africa. He encountered a local who complained about the reggae bands who always sing about Africa but rarely help with all the perpetual strife going on throughout the continent.

“That struck a very bad chord in me,” Hinds says. “We weren’t making a difference and I realized we needed to be making a difference and be active from that day on.”

From the Wounded Warrior Project to the Solar Electric Light Fund to the $300 House Project, Steel Pulse will never be accused of inactivity on the philanthropic tip. They raised more than $30,000 for Hurricane Katrina victims.

In the wake of the 2010 earthquake that ravaged Haiti, Hinds penned “Hold On [4 Haiti]” as a tribute to those affected. All download proceeds go to the Solar Electric Light Fund to electrify the clinics run by Partners in Health in Haiti.

At this point in his life, Hinds knows how to handle adversity. As a reggae band that came from somewhere other than Jamaica (Birmingham, England), Steel Pulse was considered an anomaly at the time, even shunned in their own neighborhood for their Rastafarian beliefs. But the group stuck it to all the disbelievers when they became the first non-Jamaican band to win a Grammy for Best Reggae Album (1986’s Babylon the Bandit). Hinds and his bandmates came out of Handsworth, a predominantly black neighborhood made up of a large Caribbean population in Birmingham. Dennis Brown, Burning Spear and Alton Ellis also hail from Handsworth.

In art school, Hinds says he was exposed to the “white world” that many in his community never knew about or simply resented altogether. He was turned on to music like Yes and Return to Forever.

“99 PERCENT OF THE BLACK COMMUNITY WAS IGNORANT TO WHAT PUNK MUSIC WAS ABOUT.”

“My community wasn’t exposed to any of this music,” he says. “And 99 percent of the black community was ignorant to what punk music was about.”

In the band’s early years, Hinds recalls management teams who’d book them with punk rockers including everyone from The Stranglers to The Clash to the Sex Pistols.

“Walking through those [punk rock] nightclubs it felt like you were walking on chewing gum,” Hinds says. “The amount of vomit and beer on the floor stuck to your feet. It was a completely different vibe on stage. There was continuous spitting and throwing of beer all over the place and pins through eyelids, nostrils, hairdos like Last of the Mohicans in different colors – we got exposed to that, while a lot of people in the black community were like, ‘What the hell’s going on?’”

Steel Pulse made its presence known in the U.S. after releasing its first single, “Klu Klux Klan,” about standing up to racism.

“Americans asked, ‘Who are these guys from the United Kingdom, knowing all about our history?’” Hinds recalls. “That’s what brought us into the limelight.”

Hinds’ fire as a songwriter hasn’t relented in three decades since. Check out Steel Pulse’s recent roots-reggae throwback “Put Your Hoodies On (4 Trayvon Martin).”

“I saw what the system was going to be doing from day one, and [the song] is me expressing myself, saying ‘Don’t let this court case go to waste,’” Hinds says. “Don’t let justice go unserved. Regardless of color, culture and creed, Steel Pulse is about love and justice and music.”

Through that filter, Hinds sees pros and cons with the current state of the music industry.

“The musicians that are more or less in the middle of the road, not getting a chance to be heard, are now getting a chance to be heard,” he says. “Back in the day, record companies had a foothold on how they publicized bands and how they restrained the band, as far as record sales and everything else. Now with the Internet, people can barter and trade and communicate and get a following.”

While the industry has changed dramatically since 1975, Steel Pulse’s underlying message hasn’t.

“I’d like to be recognized as one of the last bands out there making a brave attempt to sustain the roots and political aspects of reggae music to keep people on a conscious level,” Hinds says.

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Ziggy Marley is the biggest name in reggae on the planet and the closest you’ll get to being in the presence of Bob Marley. While Steel Pulse sustains the roots and politics of reggae, Marley (playing the arena 7:50pm Saturday) shoots for “galactical.”

“WHEN SOMETHING’S GALACTICAL IT MEANS THERE ARE NO LIMITS.”

“When something’s galactical it means there are no limits,” Marley explains by phone before an appearance on Real Time with Bill Maher. “I want my music to be about those truths that we don’t know about yet. I want it to be enjoyable too.”

Marley says that when he was preparing to record his recently-released Fly Rasta, listening to The Beatles and the Grateful Dead helped get him “excited about creativities.”

“When I listen to great music it gives me visions,” he explains.

In turn, Marley takes those “visions” and sculpts his own.

“I Don’t Want to Live on Mars,” the first single off Fly Rasta, is a playful enviro-Rasta jam that sentimentally weaves in and around ganja smoke plumes – and if you squint your ears just right, it could be an homage to Bowie’s “Space Oddity.”

“It is what it is,” Marley explains. “Whatever you hear is OK, man. This is not the end, this is just the beginning.”

Marley thinks Fly Rasta met its mission.

“It has gotten us closer to what we wish to achieve,” he says. “I think it did what it’s supposed to do, but we still have more records to make.”

In addition to the new full-length record, Marley’s first children’s book, I Love You Too, was recently made into an interactive mobile e-book app.

“The message is for the children,” says Marley, who has six kids of his own. “Remember to love one another. That’s all we need to remember.”

Left unsaid: One way to do it is to return to our roots.

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311, who takes the arena stage 7:50pm Sunday, was recently tasked with dusting off early fan favorites for its annual 3/11 Day show, with orchestral accompaniment, in New Orleans.

When the band’s breakthrough self-titled record – its third release overall – dropped in 1995, and tunes like “Down” and “All Mixed Up” became international mega-hits, there wasn’t really any other band in the mainstream, other than Sublime, that was turning people onto reggae-rock. For 311, going hybrid just made sense. It was their musical upbringing.

“We grew up loving rock, rap and reggae so we just put everything we liked in our music,” says frontman Nick Hexum. “We were kind of like that band people were waiting for.”

Every time 311 played a show, the bandmembers could sense that the audience was really relating to their music. That became the high they wanted most. All they had to do was tour constantly.

Since that fairytale, triple-platinum debut, the group has avoided getting wrapped up in a formula and prioritized magnetic music. The 1997 follow-up, Transistor, went platinum and reached No. 4 on the Billboard charts.

Since hitting the high-profile market, 311’s sold millions of records and worked with high-dollar producers, including Bob Rock. But even after getting signed by a major label (Capricorn Records), they continued to do everything themselves. Twenty years on, they’ve chosen to go back to being 100-percent independent. No more record label for the Omaha band.

“In some ways we’re going back to where we started,” Hexum says. “We started as an independent band, recording our own CDs on our own dime and selling them ourselves in the Midwest – it was a very grassroots operation.”

311’s 11th studio record, Stereolithic, hit the streets on March 11, and its independence extends beyond its backers.

“We had an aha moment that we could make the record we want and we used Scott Ralston, a very talented producer we’ve used many times,” Hexum says. “It’s 100-percent in-house, which felt empowering. I feel that we made the very best record we could make at this time in our lives.”

Hexum also points out the beauty in not having to worry about pleasing an A&R guy or any execs.

“We just made the record that we wanted to make,” he says. “I think that’s why it’s starting to get so embraced by our fans. It’s a return to the creativity that we were once known for.”

The wider reggae-rock genre, meanwhile is known for returns to Monterey.

CALIFORNIA ROOTS MUSIC AND ARTS FESTIVAL starts at 10am Friday, May 23, 11am Saturday and Sunday, May 24-25, at the Monterey County Fairgrounds, 2004 Fairgrounds Road, Monterey. Friday single-day pass/$65; Saturday, Sunday, 3-day pass sold out. www.cal-roots.com