COVID-19 has been an emotionally trying time for everyone.

For Jacob Reide Jennings, the founder and president of Sherlock’s Homes Foundation, he spent it changing the lives of LGBT youth.

“I was living with teenage strangers who were homeless during COVID,” he said of how his last year has been.

But it all began on Thanksgiving 2019, just a few months before the world crashed under the grip of the virus. Jennings’ marriage was over, he was laid off from his job, and he was about to lose his condo. He had hit rock bottom, but he knew he could persevere because he had been in low times before.

“I thought, you know what, if I'm going to do something, I’m going to do something that matters,” he said of the time he spent on the couch watching self-help guru Tony Robbins. “He said, ‘The universe doesn’t push you; it pulls you in the direction you’re supposed to go.’ That really started to ring my ears.”

After meditating, Jennings thought of the time he spent homeless in his teens — living out of a car and sleeping on friends’ couches. It hit him that his next chapter in life was going to help homeless LGBT youth.

“The next day I went out and I rented a house,” he said. “The day I moved in, there were already kids waiting in line. There was such a need, especially for trans kids.”

He filed for 501c3 status for Sherlock’s Homes Foundation — named for his 7-year-old Jack Russell chihuahua mix — in March 2020 and has housed nine homeless LGBT youth over the last year. The charity has since expanded to locations in Florida, Georgia and Colorado and more properties are scheduled to open this summer. Jennings’ goal is to be in all 50 states by 2025.

But Sherlock’s Homes doesn’t just give young adults a roof over their heads; they stay on scholarships based on their performances, such as opening a bank account, applying for jobs, reading books, and learning how to manage a budget. Jennings’ goal is to teach them how to be independent so when they move out, they have the tools they need to succeed.

“They have a place to stay as long as they’re improving,” Jennings said.

But since they were unable to leave the house during COVID, the charity got creative. As a real estate investor, Jennings used his savvy to purchase rental properties that are owned by the charity and used to help house other underserved populations. It kept the charity afloat in its first year.

For Jennings, homelessness is a passion project of his because he’s lived it.

“When I was 17, my parents kicked me out for being gay,” he explained. “It didn’t quite match with our religious beliefs and since I was raised to be a pastor, it wasn’t exactly in the plans.”

Living out of his 1993 Ford Escort GT that “smelled like gas” and “used to shake when I used to hit the brakes,” he managed to graduate from high school and go to college at Old Dominion University in Norfolk, Virginia. He couch-surfed for about two years, occasionally sleeping behind a gas station in his trusty car, before moving into his professor’s home when they started dating.

Jennings noted that while he worked hard to break the stereotypes, he fell into the statistics: LGBT youth are overrepresented in homeless youth, and they are usually solicited for sex within 72 hours of being homeless.

“Those statistics weren’t any different from me,” Jennings said. “But we didn’t know where to ask for help. You were ashamed. You didn’t know what to say. There’s always a stigma about being homeless.”

Homeless youth often don’t consider themselves to be homeless as their experience is different from the stereotypical homeless adult sleeping on a park bench. Younger homeless people tend to couch surf but don’t always know where they will sleep every night — they’re considered housing insecure.

This was the case for Mason Silva, who Jennings calls his “first kid;” the two met during a community meeting. Silva had moved out of his parent's home at 19 as things were tense when he came out as transgender. He was also in an abusive relationship and going through mental lows. Although he didn’t officially move into a Sherlock’s Homes home, Jennings got in touch with Silva’s mom and helped him gain the confidence to find a way to reconcile with his family and stick up for himself. He also met other trans men through Jennings and was able to access resources.

“I told my parents they needed to make the effort to accept me for who I really am. And they did; they really are trying,” Silva said. “[Jennings] was just a really big support system at the time, and he made me feel genuinely not alone … He always pushed me to just do the best I can. He’s still that way with me.”

In a better place, he is joining the Sherlock’s Homes mission by advocating for transgender youth. He’s also excited to join the charity on its upcoming national tour — the charity purchased a school bus converted into a tiny home and they’ll be stopping in cities to discuss nonprofit real estate and how people can work to end homelessness in their communities.

“His ideas and plans are going to change the world in some way,” Silva said of Jennings.

To learn more about Sherlock’s Homes Foundation or to support them, visit

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