Once homeless, now entrepreneurs

Mother-son duo driven to succeed

Karee Upendo, Alex Hart-Upendo and Avery Upendo.

Last updated on July 2nd, 2019 at 09:04 pm

To say Karee Upendo had a difficult childhood would be an understatement. Her mom was an alcoholic, her dad was addicted to drugs and she was removed from her Madison home at 7 to be placed in her grandparents’ custody.

Upendo’s grandmother was disabled, but they raised her and her brother as best they could. By 16, Upendo was pregnant and had emancipated herself, working 40 hours a week while trying to finish high school.

Karee Upendo, Alex Hart-Upendo and Avery Upendo.

“It was really difficult for me to take care of myself doing things that most kids don’t have to do,” Upendo said. “And then being pregnant and taking care of a whole different human was really scary.”

The father of Upendo’s child had a mental illness and the relationship became abusive. Eventually, she and her son, Alex Hart-Upendo, were homeless.

“It was a lot of shelter hopping when I had Alex,” she said. “We were homeless for two to three years in that transition, bouncing from shelters, staying overnight at friends’ houses, it was really hard.”

The pair were washing off in public bathrooms and moving around a lot.

“One thing my mother told me was that we’re homeless, not helpless,” Alex said. “We just don’t have a home to call ours.”

Alex’s biological father’s mother, Heidi, saw the two of them sleeping in a car in Racine and realized they were homeless. She let them stay with her and get back on their feet.

Fast forward to today, and Karee and Alex are in a much better place. Karee got married and her husband, Avery, adopted Alex. And both Karee, 29, and Alex, 11, have started their own companies: Karee Couture and Build-a-Bow.

Karee’s grandmother had taught her to sew when she was young, and she had a knack for it. When she was struggling to make ends meet, Karee would go into shops like Tiger Lily in Madison and wish she could buy the clothes.

Avery, Alex and Karee at New York Fasion Week.

“Every time I went in there they had clothes that were really different,” she said.

She would take a picture of an outfit she liked and then try to sew it herself. And she got really good at it, so friends started asking her to make them clothes.

“I wasn’t really confident in my work at the time to take on jobs for other people, but finally I was like, ‘You know what, I could make some side money doing this and save some money for Alex’s college. Why would I not do this?’” Karee asked.

At the same time, she was working 60 to 70 hours a week in automobile sales.

“People started calling me Mrs. Couture. I was really exhausted, truthfully,” she said.

In 2015, Karee decided to chase her dreams. She quit her job and officially launched Karee Couture, creating unique dresses and outfits she sells via e-commerce. So far, Karee has funded the business through apparel sales but hasn’t yet turned a profit.

“My husband is the only one that works right now,” Karee said.

Alex saw how Karee had persevered to establish her business, and at the age of 9, came up with an idea for his own company. Alex uses the sewing skills his mom taught him to make custom bow ties for his online retail company, Build-a-Bow.

“It was a definite example because it inspired me to start my company,” Alex said. “You and my dad are really awesome. You guys work hard a lot and that really inspires me.”

“His bow tie designs were really revolutionary and I thought to myself, this could really be something,” Karee said.

She looked for a mentor for Alex and found another young bow tie entrepreneur, Jake Johnson of BeauxUp, who had been on “Shark Tank.” Pretty soon, Alex was being featured on Harry Connick, Jr.’s TV show and he was receiving a huge influx of orders, including from celebrities like Ellen DeGeneres and Steve Harvey.

Alex, who was bullied for his high IQ, uses his bow ties to bring awareness to bullying and reclaim the word “nerd.” He has sold more than 7,000 bow ties, from traditional to loud patterns, in materials as unique as feathers and leather, for both humans and dogs as far away as Turkey and the Phillipines. Alex also wrote a book about bullying and offers workshops to make bow ties for different causes.

Build-a-Bow has been funded with a loan for the startup costs.

“We’re still in the red a little bit, but we just signed some huge deals that are pretty lucrative,” Karee said. “We built our brand on sweat equity. We enter every competition we can think of for entrepreneurs. We show up to every networking event that there is.”

The pair can’t talk about their lucrative deals until June, they said, but they expect Build-a-Bow’s revenue to more than double to $80,000 this year because of them. And the pair has had plenty of other success so far.

Last year, Build-a-Bow beat out four other startups to win Gateway Technical College’s Launch Box business pitch contest, along with $5,000 in seed money. The Launch Box program also provided 12 weeks of business coaching, through which Alex was able to increase sales by 30 percent.

“At that time, my bow tie prices were $5 to $8. My mentor suggested that I should change my prices,” Alex said. “After changing it, I suddenly, surprisingly, gained more customers. The reason why I got more customers was because my prices were so low, customers thought there was something wrong with my product.”

And last month, Build-a-Bow was one of three companies chosen to represent Wisconsin at the national SCORE American Small Business Championship, which included an expense-paid trip to Reno, Nevada for the competition, SCORE mentoring for a year and national publicity.

Alex Hart-Upendo with Karee, Avery and Aven Upendo.

Karee has let Alex manage the business on his own to help him learn, she said.

“I don’t force him or his ideas for his brand, even if I think he’s making a not-so-great decision,” she said. “You don’t learn to be successful from just being successful. You have to fail.”

Alex agrees: his mom has never pushed him into his entrepreneurial pursuits. He would rather do this than play soccer.

“People don’t think of me as a regular boy because having your own company, making your own bow ties doesn’t exactly get you cool points at school,” he said. “I’d rather be doing my company than doing anything else.”

Both Karee and Alex are driven to succeed and grow their enterprises even larger. Alex plans to be on the Fortune 500, Forbes 30 Under 30, and create more jobs in Wisconsin by opening a brick-and-mortar shop in Racine.

“I plan to turn my company into a franchise,” he said. “I’m thinking about publishing another book on the tricks from the trade that I’ve learned about entrepreneurship.”

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