He's been told before that a smart and capable person like him should not be in this situation.
"But I'm like, should anybody be here? Who should, then?" Pleasants said.
Last week, Trump administration officials came to Los Angeles to examine the homelessness crisis. The President, who clashes with California politicians on a number of issues, has made frequent reference to the state's failure to solve the problem.
Trump is visiting the West Coast this week, amid reports that his administration is about to launch a crackdown on homelessness -- potentially involving dismantling encampments and moving the homeless en masse into a government facility, according to the Washington Post. (It's not clear how this would work or whether the President has the authority to order this kind of action.)
Against that backdrop, Pleasants' story is a reminder of how complex the problem of homelessness can be. "It means it can happen to anybody. It's a problem we all could face," Pleasants said, standing on a sidewalk in front of his weathered belongings. A couple of unopened cereal boxes that he just collected from a food pantry sit atop his things.
"I am responsible for my own choices. I own all my decisions," he said plainly before telling his story.
Pleasants, 52, is one of 60,000 people living on the streets of Los Angeles County. The situation has been worsening in recent years -- between 2018 and 2019, the number of homeless people went up 12% in the county and 16% in the city, according to the Greater Los Angeles Homeless Count. Along LA's skid row downtown, tents line entire blocks, and encampments in other neighborhoods have been growing.
Mike Dickerson, an organizer for the homeless advocacy group Ktown for All, says the stories of many people living on the streets might surprise you.
"I think a lot of people have this perception that danger lurks in the encampments," he said. "And for myself and for other volunteers, what we found is people who are just people like everyone else, who have fallen into hard times, whether that's because of their own personal issues of because their landlord evicted them or because the rent rose in a way they could no longer pay."
One man's journey into homelessness
Pleasants grew up in San Antonio, Texas, the product of a stable, loving family who always excelled in school, according to his younger brother, Michael.
Their mother was a teacher, while their father made a career in the Air Force.
"He was always as a young child taking things apart and putting them back together," said Michael Pleasants, who followed his brother's footsteps to Yale. "He was a whiz kid."
"He (Shawn) played trombone and won several civic awards around the city."
Pleasants also overcame a physical disability. He was born with a club foot and wore leg braces throughout his childhood, his brother said. His doctor joked he would never run a marathon. In fact, his brother said, he's run several, and was in peak physical condition through his 20s.
Pleasants was a high school valedictorian, who had offers from multiple colleges, according to his brother.
Shawn chose Yale and said he received grants and several academic scholarships, which covered most of his tuition. CNN has verified that he graduated from the university.
He majored in economics, and after a few years toiling on Wall Street, including jobs at Morgan Stanley, he landed in California. Trying to fulfill a Hollywood dream, he started a photography and filmmaking company.
It was the mid-'90s, and as the DVD industry soon exploded, his company got involved in the then-lucrative world of the adult film industry. They made so much money that Pleasants wound up buying a large home in the Silver Lake neighborhood of Los Angeles.
"It was a beautiful house, something you'd see on MTV," said his brother.
But amid squabbles with his co-founders, the income dried up.
"By the time it was all sorted out, there was no business," Shawn Pleasants said.
About 10 years ago, around the same time, he also lost his mother to cancer, and her death sent him into an emotional and physical tailspin.
He went from living one place to another, eventually living out of his car before he lost that as well, his brother said.
Pleasants is gay, and considers himself to be married to another homeless man he's been with for 10 years, since before they were on the streets.
They live on the streets together, acting as a sort of team. They've held court on the same Koreatown sidewalks for six years.
"We're actually in the middle of a move," he said, explaining that some of their things are few blocks away.
He grimaced at the notion of ever going to a shelter.
"They're always set up with such rigid protocols. I would leave the place immediately," he said.
Pleasants believes a shelter would restrict his freedom and is concerned he wouldn't be able to keep all of his things due to a lack of space.
"I would prefer to be somewhere where I can still go to the library and do the things I need to do when I need to do them."
Like many of the nation's homeless, drugs, specifically meth, are a part of Pleasants' life.
He said he began using the drug before he became homeless, but insists it's not what led him to the streets.
His brother says his path toward addiction began while he was recovering from a back injury before he was homeless. "It started with pain killers, and then when they were too expensive or not accessible he medicated with other things."
Shawn Pleasants said he takes meth a few times a week as both an escape and to help him stay awake at night.
"Every time you sleep, that's when you lose and when people come and take your things," he said.
"I'm a heavy sleeper. I lose a lot."
Surviving on the streets
Pleasants has both a laptop and a cell phone. The phone and its service are free under an Obama-era program. He spends a lot of time at the library, accessing the internet and staying on top of current events.
He has sustained himself by understanding the schedule of where and when to get free meals -- using his natural intelligence to develop an efficient schedule.
"There's certain churches (that provide meals), certain food pantries -- you learn those schedules," he explained.
When asked whether Pleasants suffers from mental illness, his brother said, "I think he has episodic depression. He can go through periods of extreme depression where he will self-medicate, but then he can go through periods of being equally upbeat, resilient, and energetic."
The family has tried repeatedly to get him help, his brother said. There is a standing offer for him to move in with his 86-year-old father in San Antonio. Long-term, they would like to see him find an affordable option close to them -- perhaps through a government assistance program.
But Pleasants is defiant.
"I am not trying to bring another family member down," he said.
"I fell into it. I have to climb my way out of it."
The fact that he graduated from an Ivy League school, owned a house and made a nice living, he said, should not come as a shock.
Gesturing to a nearby tent encampment, he said, "You'll find musicians, there's a photographer, you've got all different types of people."
Dickerson says that to get people off the streets, more affordable housing needs to be created.
"I think people point to things like mental illness or like drug abuse, which do exist in this population, but they aren't the primary problem," he said.
"The idea that we're going to force people into a facility that's probably located in a very remote area is not a solution. That's not going to connect people to jobs, to housing, to services (like) mental health and addiction treatment."
"And more importantly, putting thousands of people into a giant building isn't going to get them housed if there's nowhere for them to permanently live that they can afford," he added.
Pleasants said more practical measures such as bathing facilities are desperately needed.
"We need places to shower, if you don't want us to have hygiene issues," he said. "And in order to get a job, we need to have clean clothes. Where do I iron? How do I keep them pressed?"
When asked how he'll eventually find his way out of this life, Pleasants expressed the kind of confidence that originally made him a standout.
"I'm gonna start a small business again," he said, flashing a smile.
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