Siblings at home and in the office: Meet brothers and sisters behind Long Island businesses
As children, sisters and brothers might fight over a toy, cry about who got the first piece of birthday cake, or vie for their parents’ favor, but these Long Island siblings say they’re a dream team when it comes to owning a business together.
Their businesses range from a jewelry store that dates to the early 1900s, to others started recently; and the owners agree that keeping it all in the family is what makes everything work. Just look at how well things went for siblings like the Olsen Twins, Kendall and Kylie Jenner, Kourtney, Kim and Khloe Kardashian, the Disney Brothers, the Warner Bros., the Kellogg Brothers, and the Wright Brothers.
Having loved Halloween since they were children, and coming from an entrepreneurial family, it made sense when siblings Donte and Kennedy Mcleod scared up the idea of making a business out of a haunted basement attraction.
“The Terror Below” is a Halloween pop-up in an underground Lindenhurst event space owned by the brother and sister team’s mother, Michele. Started last year, the fright fest quickly became a must-see for thrill-seekers from Long Island and beyond who stood on lines down the block to get in. Themed rooms, corridors, and passageways were created in an approximately 10,000-square-foot area — with Donte and Kennedy designing sets and props and hiring actors.
“Halloween was major in our house,” says Donte, 28. “We had speakers and bloody laboratories in our living room for kids to come in and enjoy.” Kennedy, 21, adds, “We won every costume contest we ever entered and we would have three different costumes per year. They were always unique and creative.”
As entrepreneurs, they are inspired by their mother, as well as other family members who own or owned businesses. An uncle owns a home theater productions company, and their late grandmother was a clothing and jewelry designer who owned a boutique.
“We remember going to the businesses when we were little … as we got older, we were helping,” Kennedy, a business analytics major at Hofstra University, says. “Our mom had a hair salon and inflatable company. Donte and his friends did the deliveries, and being younger, I just watched the bounce houses, making sure everyone followed the rules.”
This month the siblings started a Turo car rental business and they are heading up a team of family members who, as investors, are building two vacation homes in Costa Rica to sell and an Airbnb. All are expected to be completed next year and are beachfront properties located in a luxury development. The pair’s father is a native of Costa Rica and Donte and Kennedy used to visit their grandfather there every year.
Besides learning early how to work in a business, the siblings were taught that family ownership was the way to go.
He adds being related enhances the duo’s interest in the partnership going well.
“Donte yells at me at times and then I yell back, but I realize it’s all in love with eyes on the prize,” Kennedy says. “If it’s something we can’t decide we will ask our parents for advice or guidance.”
H.L. Gross & Bro. Jewelers began with two brothers owning the business, but it wasn’t set in stone that two brothers would own it today — that just happened.
“Our father, Michael Gross, who was a fourth-generation owner, recently retired and transferred ownership to us,” Matt Gross, 41, explains. Before Matt and his brother, Brad, took over, however, they had other careers in mind.
Matt had become a watch expert but he also loves to cook and thought of possibly opening a restaurant, while Brad had interviewed for jobs on Wall Street. When Brad’s interviews were put on pause following 9/11, his career trajectory changed after a few months working for his father.
“I quickly took a liking to the business and decided that being fifth generation of this (at the time) almost 100-year-old business was too much to pass up,” Brad says. As a teenager, Matt had worked part-time at H.L. Gross, helping his father build up the pre-owned watch section. Then after college Matt briefly owned a vintage watch business in Manhattan before deciding it was best to stick with the family’s store.
The first generation of sibling owners — Harry and Abe Gross — opened H.L. Gross & Bro. in 1910 in downtown Brooklyn. In 1922, the brothers moved to a larger space on Fulton Street, also in Brooklyn; six years later they opened a Jamaica, Queens location; then in 1940 their first Long Island store was established in Hempstead.
In 1969, the family’s first Garden City store opened, and by the 1980s there were five H.L. Gross locations. A decision was made to concentrate the business, and in 2013 its flagship 5,500 square-foot showroom was opened at 840 Franklin Ave., across the street from the original and smaller Garden City site.
“As children we visited the store quite a bit,” says Matt. He and his brother grew up in Rockville Centre. “We would help clean the showcases, and as we got older, I would assist in engraving rings and watch case backs; while my brother would enter repair and sales slips into the computer system.” He adds, “It was during this time that I developed my love for vintage watches.”
Matt and Brad say they’re very happy with how things have turned out — their personalities work well together, and they couldn’t be closer. The two share an office with desks facing each other but they say they never tire of the other being around.
“My brother takes more of the ‘boss’ position with our team,” Matt says. “He’s better at delegating and overseeing the overall business while I prefer to be more active on the sales floor. It is rare that I disagree with any of his business decisions.”
When conflicts do arise, Brad says, the brothers may avoid each other at work for a couple of hours but both are “very forgiving” and their bond always remains strong.
“There’s no substitute for family,” Brad adds. “While we may have our disagreements from time to time, I know that when push comes to shove Matt has my back and I have his.”
With siblings Tanya Willock and Temidra Willock-Morsch being four years apart in age, Tanya says she always felt “one step behind” her sister until they connected on the idea of opening a store that would offer the unexpected in Hamptons décor.
Their Southampton home design and gift shop, Hidden Gem, has some quiet and beachy looks characteristic of Hamptons vacation homes, but what dominates are products with bold patterns, intense color and rich textures reflecting the sisters’ Antiguan heritage.
“We first learned about entrepreneurship from our grandma at a young age,” Temidra, 33, says. “We would help knit and crochet pieces for us to sell in our front yard. Those experiences put us on our current career path.”
Temidra studied fashion design at the Fashion Institute of Design and Merchandising in Los Angeles, and later got a job designing custom rugs. Tanya, 29, went to SUNY Purchase in Westchester, where she studied fine arts and afterward worked as an art gallery manager for three years.
“We’ve always seen the same ‘Hamptons style’ in décor stores and often had to go online to find what we’d want to put into our own spaces,” says Tanya. The sisters grew up in Springs and still live in the family home. Temidra adds, “We wanted to create a space that showcased our aesthetic and our take on the design world.”
Tanya says there were challenges in breaking the mold of what the Hamptons was accustomed to, but the sisters were confident they could meet them by having their own store. The shop opened in 2019. “As creatives, we tried showcasing our works in other stores and saw that was hard, not only for us, but for other young talented creatives as well.”
Temidra takes the leadership role in the business — the same role she’s always had in the sisters’ relationship. She says, however, each knows to “stay in our lanes.”
“I love knowing there is someone else that can get things done the way I would,” Temidra says. “I trust my sister a hundred percent. It’s like having a built-in best friend that you get to work with every day.”
Over dinner one night, Kate Tuccillo and Haley Shea decided to open a women’s clothing store — it seemed fitting for two sisters who as little girls liked to play dress-up.
“I think it began naturally,” says Kate, 43, of St. James. “We grew up in an era of music videos and magazines that influenced what we wanted to wear.”
Kate became a buyer for a Manhattan-based boutique; and Haley, 37, of Lake Grove, used to work for a national retail management company, overseeing new store concept projects. They opened their first shop in 2015 in Huntington and then another two years later in Port Jefferson.
There was a need for smaller shops on Long Island for women looking for something more curated than what was carried in large stores, Haley says. Kate & Hale’s core customers are women 25 to 50 years old.
“We were inspired by our sisters, family members, friends, women we met through our kids’ schools and sports — really just women in general,” Haley says. “On Long Island, most of the options for adult women to shop are in department stores in major malls.”
Haley adds people had long told Kate she should have her own store because she’s a “talented buyer” with an “amazing eye,” but Haley says their business’ success results from the merging of both siblings’ talents.
“We are truly partners,” Haley says. “Kate is the buyer and merchandiser and I handle more of the back of the house with employment management and the technical/financials.”
Kate says there’s nothing like having a store with her sister.
“There is no one else I would rather be in business with,” Kate says. “The trust, belief in the other one’s ability, freedom to be yourself, and the support we provide one another cannot be duplicated.”
It was a business that helped siblings Kaley, Keira and Christian Young of Lido Beach deal with a very painful period in their lives.
The trio’s fortune turned when they appeared on “Shark Tank” and the entire panel of investors joined to back an invention created by their late firefighter and chef dad, Keith R. Young. The 53-year-old member of Ladder Company 158 in Springfield Gardens, Queens, died of 9/11-related cancer on March 17, 2018. It had been his dream to one day pitch his no-mess cutting board, The Cup Board Pro, to the “sharks.”
Regulars Mark Cuban, Lori Greiner, Daymond John, Kevin O’Leary and guest shark Matt Higgins made the offer of $100,000 for a 20% stake in the company, and the investors and the siblings all contribute 20% of any profit they earn to the FDNY Foundation.
The day after the 2018 episode aired, the inventory was exhausted, and Williams-Sonoma now exclusively sells the Cup Board Pro as well as Keith Young’s cookbook. The appearance on Shark Tank and the resulting deal was a welcomed bright spot in a dark time, Christian, 25, says.
The siblings’ mother, Beth King, succumbed to cancer in 2012.
“Our Shark Tank experience is something we will always be thankful for. It was really awesome to be able to work together to bring our dad’s dream to fruition,” Christian says. “We were at the beginning stages of grief when we went on the show — our dad passed three months prior. It became a way to channel our grief into a positive outlet to shine a light on both our mom and dad’s life after losing them both to cancer a few years apart.”
And having a business that was a family affair has made the siblings closer than they already were, they add. Formerly of Wantagh, the three recently moved to a Lido Beach house where they live in a home purchased by Kaley and her husband, Brendan Fowler.
Although Kaley, 29, has in addition started her own interior design firm, she says she loves working with her sister and brother. “Going into business with a sibling is the greatest gift,” Kaley says. “They each have parts of my parents in them.”
Keira, 19, notes the siblings being close and remaining that way was important to their mother and father.
“Growing up, our parents valued family time the most so we have always been close and had a really supportive and loving relationship,” Keira says. “Through all the hard times we have always been there for each other, which at the end of the day only makes us get closer and closer.”
As children, sisters and brothers might fight over a toy, cry about who got the first piece of birthday cake, or vie for their parents’ favor, but these Long Island siblings say they’re a dream team when it comes to owning a business together.
Their businesses range from a jewelry store that dates to the early 1900s, to others started recently; and the owners agree that keeping it all in the family is what makes everything work. Just look at how well things went for siblings like the Olsen Twins, Kendall and Kylie Jenner, Kourtney, Kim and Khloe Kardashian, the Disney Brothers, the Warner Bros., the Kellogg Brothers, and the Wright Brothers.
BROTHER AND SISTER Donte and Kennedy McLeod
OWNERS OF a Halloween attraction business, real estate development and car rental
“The Terror Below,” a Halloween pop-up in an underground Lindenhurst event space
Having loved Halloween since they were children, and coming from an entrepreneurial family, it made sense when siblings Donte and Kennedy Mcleod scared up the idea of making a business out of a haunted basement attraction.
“The Terror Below” is a Halloween pop-up in an underground Lindenhurst event space owned by the brother and sister team’s mother, Michele. Started last year, the fright fest quickly became a must-see for thrill-seekers from Long Island and beyond who stood on lines down the block to get in. Themed rooms, corridors, and passageways were created in an approximately 10,000-square-foot area — with Donte and Kennedy designing sets and props and hiring actors.
Siblings Donte and Kennedy McLeod, of Dix Hills, at the Bisou Event Space, Lindenhurst among the props and decor they used last year when they created a Hollween scary attraction. Credit: Daniel Goodrich
“Halloween was major in our house,” says Donte, 28. “We had speakers and bloody laboratories in our living room for kids to come in and enjoy.” Kennedy, 21, adds, “We won every costume contest we ever entered and we would have three different costumes per year. They were always unique and creative.”
As entrepreneurs, they are inspired by their mother, as well as other family members who own or owned businesses. An uncle owns a home theater productions company, and their late grandmother was a clothing and jewelry designer who owned a boutique.
“We remember going to the businesses when we were little … as we got older, we were helping,” Kennedy, a business analytics major at Hofstra University, says. “Our mom had a hair salon and inflatable company. Donte and his friends did the deliveries, and being younger, I just watched the bounce houses, making sure everyone followed the rules.”
This month the siblings started a Turo car rental business and they are heading up a team of family members who, as investors, are building two vacation homes in Costa Rica to sell and an Airbnb. All are expected to be completed next year and are beachfront properties located in a luxury development. The pair’s father is a native of Costa Rica and Donte and Kennedy used to visit their grandfather there every year.
Besides learning early how to work in a business, the siblings were taught that family ownership was the way to go.
“We fully trust each other and that’s important in business.”
Donte Mcleod
He adds being related enhances the duo’s interest in the partnership going well.
“Donte yells at me at times and then I yell back, but I realize it’s all in love with eyes on the prize,” Kennedy says. “If it’s something we can’t decide we will ask our parents for advice or guidance.”
BROTHERS Brad and Matt Gross
OWNERS OF H.L. Gross & Bro Jewelers
Jewelry store in Garden City
H.L. Gross & Bro. Jewelers began with two brothers owning the business, but it wasn’t set in stone that two brothers would own it today — that just happened.
“Our father, Michael Gross, who was a fourth-generation owner, recently retired and transferred ownership to us,” Matt Gross, 41, explains. Before Matt and his brother, Brad, took over, however, they had other careers in mind.
Matt had become a watch expert but he also loves to cook and thought of possibly opening a restaurant, while Brad had interviewed for jobs on Wall Street. When Brad’s interviews were put on pause following 9/11, his career trajectory changed after a few months working for his father.
“I quickly took a liking to the business and decided that being fifth generation of this (at the time) almost 100-year-old business was too much to pass up,” Brad says. As a teenager, Matt had worked part-time at H.L. Gross, helping his father build up the pre-owned watch section. Then after college Matt briefly owned a vintage watch business in Manhattan before deciding it was best to stick with the family’s store.
Brothers Brad and Matt Gross showcase their jeweled filled store in Garden City. Credit: Dawn McCormick
The first generation of sibling owners — Harry and Abe Gross — opened H.L. Gross & Bro. in 1910 in downtown Brooklyn. In 1922, the brothers moved to a larger space on Fulton Street, also in Brooklyn; six years later they opened a Jamaica, Queens location; then in 1940 their first Long Island store was established in Hempstead.
In 1969, the family’s first Garden City store opened, and by the 1980s there were five H.L. Gross locations. A decision was made to concentrate the business, and in 2013 its flagship 5,500 square-foot showroom was opened at 840 Franklin Ave., across the street from the original and smaller Garden City site.
“As children we visited the store quite a bit,” says Matt. He and his brother grew up in Rockville Centre. “We would help clean the showcases, and as we got older, I would assist in engraving rings and watch case backs; while my brother would enter repair and sales slips into the computer system.” He adds, “It was during this time that I developed my love for vintage watches.”
Matt and Brad say they’re very happy with how things have turned out — their personalities work well together, and they couldn’t be closer. The two share an office with desks facing each other but they say they never tire of the other being around.
“My brother takes more of the ‘boss’ position with our team,” Matt says. “He’s better at delegating and overseeing the overall business while I prefer to be more active on the sales floor. It is rare that I disagree with any of his business decisions.”
When conflicts do arise, Brad says, the brothers may avoid each other at work for a couple of hours but both are “very forgiving” and their bond always remains strong.
“There’s no substitute for family,” Brad adds. “While we may have our disagreements from time to time, I know that when push comes to shove Matt has my back and I have his.”
SISERS Tanya Willock and Temidra Willock-Morsch
OWNERS OF Hidden Gem
Southampton home design and gift shop
With siblings Tanya Willock and Temidra Willock-Morsch being four years apart in age, Tanya says she always felt “one step behind” her sister until they connected on the idea of opening a store that would offer the unexpected in Hamptons décor.
Their Southampton home design and gift shop, Hidden Gem, has some quiet and beachy looks characteristic of Hamptons vacation homes, but what dominates are products with bold patterns, intense color and rich textures reflecting the sisters’ Antiguan heritage.
“We first learned about entrepreneurship from our grandma at a young age,” Temidra, 33, says. “We would help knit and crochet pieces for us to sell in our front yard. Those experiences put us on our current career path.”
Sisters Temidra Willock-Morsch, left, and Tanya Willock, at their store Hidden Gem. Credit: Gordon M. Grant
Temidra studied fashion design at the Fashion Institute of Design and Merchandising in Los Angeles, and later got a job designing custom rugs. Tanya, 29, went to SUNY Purchase in Westchester, where she studied fine arts and afterward worked as an art gallery manager for three years.
“We’ve always seen the same ‘Hamptons style’ in décor stores and often had to go online to find what we’d want to put into our own spaces,” says Tanya. The sisters grew up in Springs and still live in the family home. Temidra adds, “We wanted to create a space that showcased our aesthetic and our take on the design world.”
Tanya says there were challenges in breaking the mold of what the Hamptons was accustomed to, but the sisters were confident they could meet them by having their own store. The shop opened in 2019. “As creatives, we tried showcasing our works in other stores and saw that was hard, not only for us, but for other young talented creatives as well.”
Temidra takes the leadership role in the business — the same role she’s always had in the sisters’ relationship. She says, however, each knows to “stay in our lanes.”
“I love knowing there is someone else that can get things done the way I would,” Temidra says. “I trust my sister a hundred percent. It’s like having a built-in best friend that you get to work with every day.”
Over dinner one night, Kate Tuccillo and Haley Shea decided to open a women’s clothing store — it seemed fitting for two sisters who as little girls liked to play dress-up.
“I think it began naturally,” says Kate, 43, of St. James. “We grew up in an era of music videos and magazines that influenced what we wanted to wear.”
Kate became a buyer for a Manhattan-based boutique; and Haley, 37, of Lake Grove, used to work for a national retail management company, overseeing new store concept projects. They opened their first shop in 2015 in Huntington and then another two years later in Port Jefferson.
Sisters Kate Tuccillo, left, and Haley Shea, pose for a portrait at their store, Kate & Hale in Huntington Friday, Oct. 7, 2022. Credit: Barry Sloan
There was a need for smaller shops on Long Island for women looking for something more curated than what was carried in large stores, Haley says. Kate & Hale’s core customers are women 25 to 50 years old.
“We were inspired by our sisters, family members, friends, women we met through our kids’ schools and sports — really just women in general,” Haley says. “On Long Island, most of the options for adult women to shop are in department stores in major malls.”
Haley adds people had long told Kate she should have her own store because she’s a “talented buyer” with an “amazing eye,” but Haley says their business’ success results from the merging of both siblings’ talents.
“We are truly partners,” Haley says. “Kate is the buyer and merchandiser and I handle more of the back of the house with employment management and the technical/financials.”
Kate says there’s nothing like having a store with her sister.
“There is no one else I would rather be in business with,” Kate says. “The trust, belief in the other one’s ability, freedom to be yourself, and the support we provide one another cannot be duplicated.”
SIBLINGS Kaley, Christian and Keira Young
OWNERS OF Cup Board Pro
"Shark Tank"
It was a business that helped siblings Kaley, Keira and Christian Young of Lido Beach deal with a very painful period in their lives.
The trio’s fortune turned when they appeared on “Shark Tank” and the entire panel of investors joined to back an invention created by their late firefighter and chef dad, Keith R. Young. The 53-year-old member of Ladder Company 158 in Springfield Gardens, Queens, died of 9/11-related cancer on March 17, 2018. It had been his dream to one day pitch his no-mess cutting board, The Cup Board Pro, to the “sharks.”
Siblings Christian, Kaley and Keira Young in their living room with their dogs Isabelle and Tallulah Bell. Credit: Bruce Gilbert
Regulars Mark Cuban, Lori Greiner, Daymond John, Kevin O’Leary and guest shark Matt Higgins made the offer of $100,000 for a 20% stake in the company, and the investors and the siblings all contribute 20% of any profit they earn to the FDNY Foundation.
The day after the 2018 episode aired, the inventory was exhausted, and Williams-Sonoma now exclusively sells the Cup Board Pro as well as Keith Young’s cookbook. The appearance on Shark Tank and the resulting deal was a welcomed bright spot in a dark time, Christian, 25, says.
The siblings’ mother, Beth King, succumbed to cancer in 2012.
“Our Shark Tank experience is something we will always be thankful for. It was really awesome to be able to work together to bring our dad’s dream to fruition,” Christian says. “We were at the beginning stages of grief when we went on the show — our dad passed three months prior. It became a way to channel our grief into a positive outlet to shine a light on both our mom and dad’s life after losing them both to cancer a few years apart.”
And having a business that was a family affair has made the siblings closer than they already were, they add. Formerly of Wantagh, the three recently moved to a Lido Beach house where they live in a home purchased by Kaley and her husband, Brendan Fowler.
Although Kaley, 29, has in addition started her own interior design firm, she says she loves working with her sister and brother. “Going into business with a sibling is the greatest gift,” Kaley says. “They each have parts of my parents in them.”
Keira, 19, notes the siblings being close and remaining that way was important to their mother and father.
“Growing up, our parents valued family time the most so we have always been close and had a really supportive and loving relationship,” Keira says. “Through all the hard times we have always been there for each other, which at the end of the day only makes us get closer and closer.”
