From a single modest real-estate deal Roberta Hoskie has built a thriving multifaceted business


Everything ties together. And you could say it was a few fateful decisions and an entrepreneurial spirit that has helped Roberta Hoskie get where she is today.


Hoskie started her property management firm Outreach Property Management along with her sister Tameka Hoskie-Robinson from her home in 2004, and has since expanded her business to include bus tours, community events and even a real-estate school.


It was 15 years ago that Hoskie, then an 18-year-old single mother, bought her first house — a four-family on Norton Street — to move up the economic ladder from subsidized housing. She didn’t realize at the time it would plant a seed out of which grew a passion for real estate.


“If I told you I knew what I was doing back then, I’d be lying to you,” she says from the boardroom of Outreach’s Whalley Avenue office. “The only thing I knew was that I needed to provide for my son, and I didn’t want to live in the apartment I had — I couldn’t be a statistic.”

Hoskie purchased the house for $80,000, and lived on one floor while renting out the others. It wasn’t for another few years that she looked up the value of the house — and discovered it was actually worth a whopping $300,000.


“That was when I understood the power of real estate and what it can do for you,” she intones before excitedly declaring, “Of course I sold it! It was the biggest check I had received at one time; I’ll never forget that.”


Having caught the real-estate bug, she used the proceeds from the sale to invest in more properties. She is still passionate about affordable housing, having created Outreach Foundation, a non-profit advocacy group for affordable housing for low- to moderate-income families, which she said will be a big focus for 2012.


“My first apartment was affordable housing, and that allowed me to go back to school,” she says. “If I didn’t have that, I would have been trying to work two or three jobs, or at McDonald’s. I understand the power of it, and I’m very passionate about my community and giving back, because I’m born and raised in New Haven.”


Not that starting her own company didn’t already require a huge leap of faith, but at the time she was already making six figures while working at New York’s Albert Einstein College of Medicine, where she helped establish the East Coast Division of the Department of Pediatrics’ Office of Research and Development, which subsequently was awarded $20 million in federal and state grants. She laughs off the risky move today.


“It was like I was blindfolded then jumped off a cliff,” she laughs. “But I thought if I could help bring in $20 million, I should see what I can do for myself.”


While Outreach manages rental properties throughout Connecticut, Hoskie says 85 percent of its properties are in New Haven. Like most property managers, she says Outreach is a “landlord for the landlords,” and carries out the basic functions and tasks needed for a rental property, including maintenance work. But Hoskie says she is particular about who she does business with and protective of her brand, having let go of a few contracts in the process.


“When I was in the company for about two years I did a very risky thing: I let go of one-third of my portfolio,” she says. “When you start in a business you take everything you can get, but there is a certain standard we have. They were slumlords and I couldn’t have my brand associated with that.”


It’s an innovative and creative edge that she says has helped the business thrive, and the quarterly Rental Bus Tours are a perfect example; gathering prospective tenants onto several chartered buses that spend the day touring available properties throughout the county in efforts to rent more apartments more quickly. The passengers are even shown a pre-recorded video introduction from Hoskie as they go on their way (which she demonstrates in an appropriate game show-host voice).

The last tour had more than 50 people attend, and the response was exactly what was wanted.
“We made our quota for the month in one day,” Hoskie says with an understated pride. “We were able to rent a good number of apartments while doing something fun at the same time. You build a lot of different stories, and I can create wonderful relationships.”


Even those who don’t rent that same day often come back. She says Outreach has about 3,800 tenants throughout New Haven County, and Hoskie says its hard even to go to the grocery store without running into someone Outreach has helped find a place to live.


Her own outreach extends to motivational speaking, as Hoskie becomes more sought-after to address different groups, particularly professional women’s groups and budding entrepreneurs, but she particularly enjoys talking with high school-aged girls.

She’s even keen on putting the power in others’ hands as well; she started the Outreach School of Real Estate last year, and averages 15 students per eight-and-a-half-week session, Hoskie uses properties in the city to help her students connect to textbook concepts. She’d love a higher enrollment but is still proud of the numbers, having seen other programs close because they couldn’t attract even five students. She’s already seen two of her students move on to start their own real estate investment business.


But getting information out to people doesn’t stop there. Every summer, Outreach throws its HOPE (Housing Opportunity for People Everywhere) Community Festival and Housing Summit, a street festival featuring live music and performances, food and entertainment for children, and around 40 non-profits and community organizations that each set up booths to disseminate information about themselves.

Visitors can utilize the festival to find out about programs for housing and financial assistance, counseling and health services, as well as government assistance. There’s even a raffle that will pay the winner’s rent or mortgage for the month.


“There are more than 500 non-profits in New Haven, and they’re all doing wonderful things for the community,” Hoskie says. “But they’re all here, and there, and there. So let’s bring them together under one roof and invite the community. You’re more powerful in collaboration.”


She is a member of the New Haven branch of the NAACP, and chairs its Economic Development Committee. She (along with the group’s Housing Committee chair) played an instrumental role in forging a partnership with the organization and First Niagara Bank to pledge $7 million as part of a Community Reinvestment Act initiative, which includes funding for a small business/microloan program, and home ownership assistance.


“I know what I went through, and if I didn’t have a strong mindset I would have been under a long time ago,” Hoskie acknowledges. “I’ve tried to get funding and got denied. I understand what it takes, so if there’s any way to help others help themselves, and create businesses and jobs that create a stable family environment, then let’s do it.”


Jim Rawlings, president of the NAACP’s New Haven chapter, says that stabilizing the housing market is vital to stabilizing the community, and as his organization pushes further for economic equality, the investment from First Niagara makes New Haven “a great beta site for other urban centers.”


“We need people with these skills, and with that business acumen to move forward in the 21st century,” Rawlings says. “The work Roberta has done is so important, and she has been an excellent role model of the kind of work we do to help build our community.


“These loans to start new businesses give our young people hope, and show them there are opportunities that allow them to become more independent and have options,” he adds.


Hoskie has an unmistakably proactive attitude towards obstacles she and the company encounters, preferring to look at the “equivalent or greater” opportunities each challenge might present. She points to an unfortunate episode in early 2009 in which a landlord’s New Haven and West Haven properties were going into foreclosure, which prompted a number of tenants, who now had 30 days to find somewhere else to live, to show up at Outreach’s then-East Street office in need of help. It was in re-placing the tenants and getting them in touch with services and resources they needed that she got the idea for the HOPE festival, the first of which focused on foreclosure and how tenants can be affected.


Hoskie says Outreach is looking forward to what may be its best year yet; the company has even started a new branch, Outreach Realty Servicing, which will partner with national developers, with several of whom they are just beginning to forge working relationships. It’s her hope that the company is poised to attain her goal of becoming a multi-million-dollar enterprise.


While she is quite proud of her achievements, she stops short of hogging credit for all the positive things Outreach aims to provide the community.

“I learned that you have to take the eyes off of yourself and understand that what you’re doing is about other people,” she says. “I do carry a burden, though, because if we don’t do what we have to do right, someone else is affected. And that’s heavy.”