Samantha Pearl, performing at Crossroads in Richmond.

Samantha Pearl performing at Crossroads in Richmond.

WALKING CARY STREET in Richmond, I’ve met a number of street musicians, who generally range in skill from primitive (homeless guy with ukulele) to moderately talented performers on guitar, banjo, fiddle, trumpet, clarinet, and harmonica.

Samantha Pearl is in a different category altogether.

She too plays on the sidewalk with her guitar case open for tips, but everything else about her—from her ripping bluesy guitar slides to the original tunes sung in an angelic soprano—seems totally out of place.

“When you’re polished and you’re playing on the streets it throws people off,” said Pearl, a 26-year-old entrepreneur who’s been playing guitar since she was ten. A few years ago she left Los Angeles, her home city, and the restaurant business to move to New Orleans and launch a career as an artist.

“I’ve always been my own person and my own boss,” said Pearl, who has primarily worked as a street performer for about four years, “so the more I started to see that I was able to be financially secure with my music, I started to trust that more.”

Pearl, who disciplines herself to eat healthy food, workout and avoid alcohol and drugs, quickly learned that playing on the streets, while not as glamorous as playing in clubs and venues, is often more profitable than a scheduled gig. Why would she play in a bar or restaurant that pays her little if anything and the tips are much less plentiful?

Street performing, Pearl said, “is like practicing in your room but outside and you get paid for it. That’s why like ever since I started I was like ‘I’m never going just practice in my room.’

And get paid for it, she does. Pearl said she hoped to make about $4,000 in April, which marked the beginning of her busy summer season.

Except that, to collect big paydays, she typically needs to leave Richmond, a city that she stumbled upon through her travels and where she fell in love with another artist who supports her ambitions. As much as she enjoys Richmond, which she calls her sanctuary, Pearl said she would not be able to make enough money if she did not venture to other cities, such as Washington D.C., New York, and of course New Orleans, her favorite spot to play.

“When I’m down there I’m really focused and I have a clear head,” she said of New Orleans.

On a typical day of street performing, Pearl might catch a bus up to Washington D.C. where she’ll hope to make double or triple what she would in Carytown, enough for her to justify the four-hour combined trip and the price of two bus tickets. One of her favorite spots to play is in front of the White House.

“Secret service lets me,” Pearl said. “The guys love when I play there, because they think I’m beautiful and that I have a beautiful voice.”

Pearl typically opens with her standard two-hour set before moving into what she calls writer’s mode; Pearl writes all of her music on the street. “It’s a really good exercise to see how people react to what you do,” she said. “It’s kind of like push and pull.”

The challenge Pearl now faces is to continue her steady growth. In addition to her street performing, she has several regular spots, including restaurants in Washington and the Hardwood Brewery in Richmond, that continuously book her for some indoor shows, but she’s always looking for more well-paying gigs. She said she had hoped to go West, but fate is pulling her the other direction for one of her best gigs yet.

After playing at a talent show at the Tin Pan in Richmond, Pearl received a call from a punk group who knew of Pearl’s prowess—she plays punk music too—inviting her to join them on a paid summer tour around Europe. She was so excited that the typically alcohol-free Pearl wanted to get a drink to celebrate.

While her journey in Europe will undoubtedly be worthwhile and eye opening, her larger journey is still unraveling.