In the summer of 2020, 23-year-old Annie Sullivan dove into the deep end of small business ownership. Shortly after she graduated from college and returned home to Red Hook, Covid-19 hit. Sullivan, who had taken a job at a juice bar in the center of the village, quickly became its sole employee, greeting only a handful of masked customers each day.
Her boyfriend, Mike Kelly, whose coaching job had abruptly halted, often joined her there, and the two daydreamed about what they would change if they owned the shop. When her boss told her she planned to either close or sell, Sullivan used a family loan originally intended for graduate school to purchase the business, which she rebranded as Bliss Juice + Cafe.
“I was looking ahead, in the middle of Covid, and asking, ‘What is the future job market going to look like?’” Sullivan recalls. “Everybody was working from home or unemployed. Were we ever going to be employed again, unless we decided to become entrepreneurs and put all our ideas to the test?”
In five years, Sullivan, who owns the business with Kelly, has significantly grown Bliss’s menu, whose offerings range from cold-pressed juices and smoothies to coffee, matcha, and nourishing dishes for breakfast and lunch. This spring, they moved the business to a larger space down the street, and a cocktail bar concept that will take operations from day to night is currently in the works.
Like so many of her Generation Z cohort, the oldest of whom turned 28 this year, Sullivan has found small business ownership to be the most stable option in a rapidly changing world. (A 2024 Newsweek survey estimated that the unemployment rate for 20–24-year-olds was 7.9 percent, nearly double the 4 percent national average at the time.) “Our economy looked entirely different than anyone else’s, especially as we were coming into the workforce,” she says. “We went to college and got trained for a workforce that hasn’t existed for 20 years.”
The Gen Z small business engine, however, is just revving up. According to LinkedIn, about 18 percent of business founders in 2024 were Gen Z, compared to 14.5 percent in 2023, indicating that the makeup of the small business landscape is already shifting around us.
In the Hudson Valley, Gen Z business owners are finding that entrepreneurship, a traditionally unpredictable and financially risky endeavor, is particularly well-suited to their fluency with social media and marketing, and offers them the opportunity to build values-based businesses that speak strongly to the customers they want to reach.
Rewriting “The Way Things Are Done”
Jillian Reed and Masha Zabara’s journey with Thrift 2 Fight was also forged in the societal upheaval of the pandemic. When widescale protests against police brutality broke out in the summer of 2020, the two friends who met at Bard College Conservatory launched a series of pop-up clothing sales to raise money for social justice organizations, which coalesced into a one-of-a-kind model for supporting grassroots social change backed by thrift-store sales. After two years of pop-ups and community fundraising, they opened their brick-and-mortar shop in Tivoli.
Thrift 2 Fight’s model is straightforward but radical in its transparency: 10 percent of every purchase goes directly to grassroots organizations focused on racial, queer, and disability justice. To date, they’ve raised and donated more than $118,000 to more than 30 organizations.
“A lot of businesses will say we donate ‘a portion of proceeds’ or ‘we donate 10 percent of profits,’” says Reed. ‘But most small businesses are not profitable within the first two or three years, so ‘a percentage of profits’ is a very elusive thing. We decided to donate a non-negotiable 10 percent of every purchase, and the rest goes to operating the thrift store.”
The two say they intentionally chose to operate outside of the “nonprofit industrial complex,” which has been criticised by the social justice community for bureaucratic structures that can limit the impact of mission-aligned work. Instead, Thrift 2 Fight is incorporated as a public benefit corporation, a for-profit business with a commitment and obligation to prioritize and provide a social good before profit, to avoid reliance on grants while still being able to redistribute funds to activist organizations.
Their store is as much a magnetic gathering space for the community as it is a retail store. Customers participate in acts of mutual aid through a “mitzvah wall” (inspired by the one at Lagusta’s Cafe in New Paltz) where anonymous discounts are left for someone who may need them. The store also has an $8 Room where prices in the room decrease each week until the remaining items become free.
“We’re not required to tread into the steps of a particular company or a corporation or the ‘way things are done,’ says Zabara. “We don’t have to be open on Christmas Eve or Black Friday. We don’t have to call our employees a family and stop there. We can create community and we can make a business be a community at the same time.”
Digital Natives and Marketers
For Gen Z, who grew up with social media, content creation is second nature. Instead of tapping another member of their team to handle marketing, the new generation of business owners often handle everything from photography and video creation to posting on social media to website creation themselves. This hands-on approach offers them the ability to finely tune their public image in a way that is tightly aligned with their vision for their businesses.
For restaurateur Kevin Arias, who opened Agave in New Paltz at 26, presentation is paramount. He and his younger sister manage the restaurant’s website and social profiles, curating beautiful, well-lit images that showcase the restaurant’s Mexican-Asian fusion menu and cocktail program.
Everything from plating to interior design is curated to be experienced online-first, in step with how diners today encounter restaurants before ever stepping foot inside. “I take pride in presentation and I think about decoration and how things look all the time because everything comes to the eye first,” he says. “Everything has to be Instagram-worthy.”
At Bliss, Sullivan shoots vibrant, mouthwatering images of smoothies and juices, and first-person video for Instagram on her iPhone, posting when time allows. “We always joke that whenever I’m feeling like my business might fail, I just need to post on Instagram,” she says. “If we’re slow, literally all I have to do is come up with something new and post about it and everyone comes the next day.”
Tapping into authentic excitement has also been a recipe for success at Thrift 2 Fight, where Reed and Zabara manage their social media themselves. “Every time we post about something that really matters to us, it becomes really successful on Instagram,” Zabara says.
Their most widely circulated posts are those tied to their values and call-to-action moments like community stories and transparent updates about donations and mutual-aid programs rather than merchandise. The two also recently led a social media workshop for local businesses, and even gave a Tedx talk about their approach to grassroots fundraising and community-building.
A Collaborative, Caring Management Style
For these Gen Z business owners, a management style based in collaboration and care rather than top-down hierarchy feels integral to their role as business owners.
At Thrift 2 Fight, Reed and Zabara are working to challenge the always-open paradigm of the fast fashion retail world. “We protect each other fiercely from overworking,” Zabara says, noting that it is common to hear an employee ask, “Have you taken your break yet?” Their scheduling ensures two consecutive days off for every employee. “We also have volunteer days where middle schoolers and people in their 60s and 70s have volunteered with us, and people genuinely just like the energy here and feel comfortable,” adds Reed.
At Bliss, Sullivan jokes that she gets a lot of her own management coaching from Dr. Becky Kennedy, a clinical child psychologist and founder of the Good Inside framework for parenting that emphasizes emotional steadiness and collaborative problem-solving.
“I love that millennials and Gen Z are changing the paradigm of what it is to be a manager or a boss or to be in a workplace,” Sullivan says. “It doesn’t really serve you to necessarily be in a strict hierarchy with subordination required. It pays to have designated roles, and it pays to be nice to each other and lead with love. Every person in a workplace is a person, and they’re spending more time with you than they are with their families.”
At Agave, collaborative, caring management stems from the strong work ethic Arias’s immigrant parents and relatives instilled in him. He began working in restaurants as a dishwasher at 14, and worked in every position from busboy to bartender and manager before starting his own business after graduating with a degree in Business Administration from Dutchess Community College. “My parents’ experience in life really shaped me,” he says. “They’re very hard-working people.”
Arias says that while some older employees may struggle to have such a young boss, he says his approach to working alongside his employees has gained him respect as a leader and a business owner. “I take pride in being very hands-on,” he says. “When my staff sees me working as hard or harder than they are, they appreciate that.”
For Arias, being a good business owner is about honoring the weight of responsibility to support his staff and his customers. “You have to take care of the people around you. It doesn’t come down to what generation you’re part of,” he says. “It comes down to who you are as a person.”
Building Values-Based Businesses
Like every generation that has come of age in the workforce before them, Gen Z business owners want to reshape the workplace to fit their values. And whether it’s progressive cultural movements or old-school hard work and hustle, Gen Z business owners are unafraid to wear those values on their sleeves—and to make them very visible parts of their businesses identities.
