How we found success in US travel industry

From left: Nancy Gakere, Naomi Ogutu and Kea Simmons.

Photo credit: Pool

Every year, thousands of Kenyans seek greener pastures in the US. Some get lucky, others do not. For those who do, some start with menial jobs and rise to set up their thriving businesses.

Naomi Ogutu, 48, Kea Wakesho Simmons, 41, and Nancy Gakere, 50, are among Kenyans who have found success in the US, all in the travel industry.

Nancy has been living abroad for over 30 years.

“I came to the US in 1990 at the age of 17. I had just finished high school in Kenya so I came here to attend college,” she says.

She started off as an accountant, before turning her travelling hobby into a business.

“I started blogging in 2019. I used to share my travel adventures. As an accountant, travelling was my way to wind down and escape my hectic work environment,” she says.

She soon got a following from enthusiasts, who started asking if they could travel with her.

“I decided to curate group trips to places I had been to and offer them to my followers to allow them to have the same experience. This seemed to resonate with many of them who wanted to travel but didn’t know how to make it a reality,” she says.

Being a business that requires minimal capital—just cash to create the website and social media management—the travel curation enterprise picked up fast.

She named it Fancy Nancy Travels.

“All the clients need to do, is show up, and everything is taken care of; from the moment they arrive to the moment they leave,” says Nancy, who runs the company that operates out of Los Angeles, California.

“This is a business that came about as a natural progression from my passion for travel. It’s a hobby turned into a business. My clients are mainly African women in the diaspora, with the majority based in the US. I connect with them mainly through social media,” she says.

Is being an entrepreneur in the US better than being in Kenya? I ask.

“I haven’t done much business in Kenya, so it’s hard to compare, but I can say that the business environment in the US is quite regulated and straightforward,” she says.

She usually takes clients to countries she has visited, which as of now, is 30 countries.

“In 2023, I took clients to Mexico, Costa Rica, and Indonesia (Bali). In 2024, the trips are to Greece, Cuba, the Maldives and Indonesia (Bali),” says Nancy.

Nancy Gakere, the founder of Fancy Nancy Travels.

Photo credit: Pool

As she grows her business, does she feel like she has achieved her dream?

“I feel like I am still on the path to achieving the American dream, but definitely on the right path,” says the entrepreneur, who urges people to focus on the passion and not the money.

“I honestly did not think about establishing the company, but things progressed naturally to where I needed to formalise it,” she says.

Naomi Ogutu is another Kenyan living in the US who has found success in the travel industry.

She went to the US in 2012 and started by working as a taxi driver.

She had vowed that by the tenth year of her stay in the US, she would be an employer, and indeed, her dream had been fulfilled.

When she reached the US, it was not easy to settle.

“It took us one year to finally get our papers right, but we got our work permits in six months. No one hosted us. When I landed at JFK with my family, booked a hotel, and after a week, got an apartment (not easy - we were assigned by a nonprofit organisation called CAMBA) which got us an apartment and connected us with Upwardly Global for New Americans. I guess the fact that no one hosted me, gave me the courage and confidence to use my independent thinking in navigating my life here in the US,” she says.

Naomi Ogutu who owns a personalised tour firm in New York City stands next to one of her company vehicles. 

Photo credit: Pool

“I’m sure if I were hosted by anyone, they would have discouraged me from even living in New York City; that’s understandably very expensive. But through all my struggles, I’ve thrived,” she says.

Her first real job in 2013 was in retail, where she worked at a high-end retail chain on 5th Avenue and 53rd Street Manhattan for three months. At her second job, she received training and placement at an agency that got her a job at a major electric company in New York.

“I was a systems administrator in their sub-surface construction department. My work entailed being a focal point of contact and coordination of the field crews, the engineering department and the HR department. My work was to update these three departments on work progress, troubleshooting and reporting lost hours due to emerging issues in the field and any work delays. My contract ended after three years and I moved on,” she says.

Ms Ogutu’s third job was at the New York University Treasury Department. “Here, I started as an administrative assistant and in a few months, my manager moved me to auditing. I lasted just one year in this job, and in 2016, I made a big blunder at work that almost got me fired, but I opted to resign before they could fire me,” she says.

At that time, she was going through personal challenges which affected her work.

“I even contemplated suicide. I was saved by a truck driver as I sat by the Mississippi River (a sign read ‘This is the highest point of the Mississippi River’). I was contemplating jumping in. But that Good Samaritan or angel just held my hand, took me to a Wendy’s restaurant, bought me lunch, let me cry and tell him everything! A white man I didn’t even know. He wrote his phone number on a paper but I threw it away. I couldn’t face him after that incident,” she says.

Her business idea was born right by the banks of the Mississippi River.

“I went back to New York with my mind made up. It was my time. One day, an Uber driver named Famara from Senegal drove me home. We talked a lot and he told me, ‘Hey sister, Uber business is good. We make even a lot of money stress-free. No clocking into an office, no boss, no schedule—you create your own schedule.’ So he told me about the master Cabbie Academy and in 2017, I was already an Uber driver in New York City.”

After getting her New York City Taxi and Limousine Commission license and registration, she immediately started driving for Uber and Lyft in New York City’s five boroughs of Manhattan, Brooklyn, Queens, The Bronx and Staten Island.

She established her firm in 2018, but incorporated it in 2020 as an S-Corporation, Naomi Cars NYC, with offices on West 57th Street, in Midtown Manhattan, NYC.

“In 2018, I started marketing my sightseeing tours to my Uber clients. If we clicked with a client, I would offer them my business card and let them know I’m available to take them around and showcase the beauty and hidden gems of New York City. Now I have six tour guides, and I work with 19 drivers who are independent contractors,” she says.

Entrepreneurship was not a new game. Ms Ogutu had been in business in Kenya before moving to the US.

She ran a bookstore in Nairobi which supplied books to colleges and universities.

“I knew that in the US, hard work pays, and the business environment was straightforward and rewarding. Kenya was okay, but I was constantly chasing after procurement officers to get paid. You are taken around circles, just to bribe. I got tired of the corruption and lack of ethics,” she says.

Has she achieved what she had hoped to? I ask.

“My journey abroad was propelled by the desire to give my children a good life. I’m a single mother of three children. My firstborn daughter, 23, works for the state of New Jersey. My son,19, is a freshman at SUNY Polytechnic Institute, studying Mechanical Engineering Technology, and is already on the Engineering Department Dean’s List. He’s on a full scholarship to a microchip manufacturing company that has also offered him a very prestigious paid summer internship. My other daughter, 17, is also headed to college with a full-ride scholarship. She’s been admitted to 20 universities, but she has zeroed in on two - RPI (Rensselaer Polytechnic Institute), which offered her the scholarship, and Embry Riddle Aeronautical University to study aeronautical engineering. We are waiting to get her scholarship package, then she will decide where to go,” she says.

There are many job opportunities that have sprouted from travel. Kea Wakesho Simmons travelled abroad for the first time to Korea when she was 23. She says that it was out of curiosity about the world and different cultures and histories.

Her travel business also started with a passion for new destinations.

“I worked in the US Army as a human resources specialist and served for five years, including deployments to Iraq and Korea. During my time in Korea, my passion for travel was ignited, fuelling my desire to explore the world,” says Wakesho.


Kea Simmons, the founder of Traverze Culture.

Photo credit: Pool

In 2011, she left the military and went to Afghanistan, as a civilian.

“I worked there for three and a half years. I was coordinating over 5,000 personnel and managing administrative procedures. I worked in Estonia, Bulgaria, and Iraq for seven and a half years. Living and working in these countries allowed me to visit 45 different countries and live in seven,” she says.

She wanted to share her extensive travel with the world, hence she co-founded a travel concierge firm World Views, with a capital of $10,000 (Sh1.32 million.)

“One of my notable achievements was leading a group of over 100 travellers to Kenya, where I introduced a fresh perspective on Afro-tourism in Africa. Recently, I expanded my efforts to Central America. In 2023, I relaunched my business under Traverze Culture, continuing to provide the same services,” she says.

Traverze Culture is out of the US and has its headquarters in Nairobi, Kenya, with a team of 12 employees.

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