How This Co-Founder Is Building The Airbnb For Work


Taking on new challenges and experiences can be enriching. Co-Founder and CEO of Hoppin, Bilyana Freye, is a big believer in experiential and multi-disciplinary learning. In fact, Freye is a product of all of her experiences. “From a very young age I’ve always loved new beginnings,” she begins. “It’s so terrifying but ultimately so rewarding and exhilarating.”

Job shadowing is one of many opportunities that anyone can take part in, especially if you feel like you need a change of pace in your work-life, or want to try something new. Freye and Luuk Derksen, Co-Founder, and CTO are on a mission to empower people to find a career they love. Hoppin is a New York-based shadowing marketplace. Hoppers (those that shadow) can try different jobs with no commitment for a short period of time.

Bilyana Freye, The Hudson Yards. Photo Courtesy of Freye.

There is a range and breadth of experiences that Hoppers have had. An engineer shadowed a jewelry designer for a day to explore life as a creative. A former accountant spent two days at an experiential marketing agency in search of her passion. A female angel investor was interested in the cannabis space and shadowed a Founder of a cannabidiol (CBD) beauty brand. There are many opportunities one can take on. Freye is very experienced in the realm of job shadowing. Originally from Bulgaria, she moved to the U.K. on scholarship when she was a teenager. She stayed in the U.K. for 14 years and graduated from the London School of Economics and Political Science.

At the height of the 2008 financial crisis, her job search led her to take on a role in risk management at The Royal Bank of Scotland (RBS). “The only divisions hiring were in risk-management [and] I was really grateful to have that job,” she beings. “I [just] realized it was a really bad fit.” She took this unfortunate situation, flipped it and made it into a networking opportunity. She asked a private banker if she could shadow him in a department that seemed like a better fit. “I’ll never forget it. He took me along to two meetings and I loved the adrenaline.” She instinctively knew that she wanted to work for that branch of the company. “Everything was a lot more fluid and energetic and I just instinctively knew I should be there,” she says.

After one day of shadowing, they created a new role and hired her. “I was there for five years,” she exclaims. “This massively changed my career trajectory within the same bank.” The shadowing got her working at Coutts, a well-known British private bank owned by RBS. “I was working with U.K.’s top high net worth entrepreneurs and still, I wanted to test my hand at different industries and fully explore my potential,” she says. Her impact in the company didn’t stop there. She implemented these shadowing opportunities between bankers. “These internal job shadowing schemes really increased empathy, remove stereotypes and increase deal flow,” she comments. Through her perspective, spending the day with someone provides the opportunity to really step into his or her shoes and see what they go through on a day-to-day basis.

Her career didn’t stop at the bank. Freye continued to challenge herself, through the realm of shadowing. This driven entrepreneur was selected to take part in “The Apprentice” show in the U.K. while she was employed by RBS. Even though she remembers the experience feeling extreme, it was the only way for her to try her hand in different industries and jobs back to back. This remarkable woman wanted to fully explore her potential. “I’m really living my truth and that was discovered through experiences,” she admits. “There’s no better way to know if something is right for you if you don’t experience it. It’s been 10 years in the making of knowing how powerful job shadowing is.” We may have unlimited information at our fingertips, even at the touch of a button, but Freye concludes that nothing prepares you for how the right fitting job will feel until you experience it.


A few years ago, Freye and her husband wanted to start their new lives, as a family, with an adventure. Never living in America before, they decided to move to New York. “It was a symbolic move for me; a couple of months after my 30th birthday and a wedding,” she says. “After seven years in finance I took a hard look at my life and thought ‘Is this really what I want to do?’” Freye felt like she should find a job that made her energetic and enthusiastic. It led her to the tech industry and working for a company called Decoded, which teaches people how to collaborate with technology.

“I felt like I should experience a change; Tech is underpinning our generation and it’s affecting [many] industries,” she emphasizes. “I moved from a large corporate [job] to a small tech startup.” She remembers feeling how exciting and daunting it would be. “When I did the big move from finance to tech, I couldn’t help but think ‘what if I could have shadowed again?’ and ‘why doesn’t it exist?’”. A piece of her felt there was still so much more to discover. She met Derksen at Decoded. The second time founders ended up bonding over the importance of finding the right job, the right fit. “Job shadowing is the best thing since sliced bread,” she laughed. “It can help college students figure out what they should go in to; it could help experienced professionals just like me; it can help baby boomers stay relevant by trying out this intimidating world of startups.”

“There’s no better way to know if something is right for you if you don’t experience it," Freye exclaims. "It’s been 10 years in the making of knowing how powerful job shadowing is.”

What makes Hoppin unique is how affordable the shadowing experiences are and how it benefits both the Hoppers and the hosts. “We wanted a new take of the word ‘hopping,’” she explains. Job-hopping can be seen as negative but Freye emphasizes it’s necessary to find what you’re looking for, to embrace something new. “Time is the most valuable thing we all have,” she continues. “Taking five days to try five different jobs is one of the most efficient things that you can do when you’re looking for [your] next passion or purpose.”


“If you’re passionate about what you do and are looking to share your craft and experiences, host” Freye advises. Hosts that take part in this shadowing experience maximize their exposure, earn something extra and get a fresh perspective. “The hosts get to meet pre-screened, talented individuals who are proactively exploring their next move,” she explains. “There are different benefits to different types of hosts.” A bond can be created between host and Hopper. “Being able to share that passion with someone that’s curious about what they do is very beneficial,” she goes on. The feedback she received from hosts is positive, as they enjoy helping others. In addition to the revenue, Freye explains how hosts can bring Hoppers along on their business journey, meet new talent and get a fresh perspective from people that value the experience and the business. “So many people that I speak to are actually job switchers [and] a lot of them are ex-finance, ex-lawyers, ex-engineers,” she admits. “They wish [they] could have shadowed someone.” She is passionate about helping others discover their talent.


“All of our shadowers today have been women, and a huge portion of them have been minority women,” she states. “It’s such a positive, amazing experience.” Hoppers pay an average of $150 a day to go shadow. Out of several shadowing success stories, one stuck out in particular. An angel investor wanted to learn more about the cannabis space by immersing herself in the business. The day she shadowed the Founder of a cannabidiol (CBD) beauty brand, nothing went as planned. “The Angel investor loved the experience,” Freye shares. “For the investor, it was really interesting to see all the battles we fight and all the problems we have to solve as entrepreneurs day in and day out.” The challenges threw off the day planned, but the experience was more authentic.

Team Hoppin (Co-Founder's Bilyana Freye and Luuk Derksen). Photo Courtesy of Freye.

Freye describes the community of Hoppers as being outgoing. “The people that do it [are] a very self-selecting group,” she says. “They’re very, sociable, intellectually curious, positive, outgoing women.” A majority of industries are still predominantly male. Hoppin helps deconstruct this problem in many ways. “There are still too many industries that are male-dominated; we still see dreadful statistics about that and a lot of companies are trying to change but it’s a slow process,” she says. Freye offers a powerful, bold suggestion to the men asking what they can do. “My answer to them is, sign up to be shadowed. “It is such a real, tangible solution. Anyone can sign up, and do it. Bring in an amazing woman to work, and show her what her future could look like,” she concludes. A lot of the shadowing opportunities turn into mentorships with the host afterward.

Freye has many plans in store for Hoppin. In fact, she is one of three entrepreneurs that won the Uber x Girlboss competition last month. The competition's goal is to empower startups with financial support, mentorship and resources. Hoppin came in second place with a prize of $65,000. Freye is extremely grateful for their backing of Hoppin's vision. In addition to the recent win, she also looks forward to launching several more locations in the future, and hopefully expanding to colleges and universities.

This Co-Founder is real, authentic, and truthful. She understands the difficulties behind starting something new -- and she wants our Swaay audience to know. “Starting your business or quitting your job is a really highly stressful thing,” she begins. “It’s a big life commitment [and] my advice would be to start small.” Even for those that aren’t considering switching their jobs and just want to learn something new, Hoppin is a resource for that as well. “It can be a slow process, as long as you’re taking action and putting yourself out there,” Freye continues. “In the long run, I see [Hoppin] as the Airbnb for work.”

“From a very young age I’ve always loved new beginnings,” Freye says. “It’s so terrifying but ultimately so rewarding and exhilarating.”

3 min read

Help! My Friend Is a No Show

Email armchairpsychologist@swaaymedia.com to get the advice you need!

Help! My Friend Is a No Show

Dear Armchair Psychologist,

I have a friend who doesn't reply to my messages about meeting for dinner, etc. Although, last week I ran into her at a local restaurant of mine, it has always been awkward to be friends with her. Should I continue our friendship or discontinue it? We've been friends for a total four years and nothing has changed. I don't feel as comfortable with her as my other close friends, and I don't think I'll ever be able to reach that comfort zone in pure friendship.


Dear Sadsies,

I am sorry to hear you've been neglected by your friend. You may already have the answer to your question, since you're evaluating the non-existing bond between yourself and your friend. However, I'll gladly affirm to you that a friendship that isn't reciprocated is not a good friendship.

I have had a similar situation with a friend whom I'd grown up with but who was also consistently a very negative person, a true Debby Downer. One day, I just had enough of her criticism and vitriol. I stopped making excuses for her and dumped her. It was a great decision and I haven't looked back. With that in mind, it could be possible that something has changed in your friend's life, but it's insignificant if she isn't responding to you. It's time to dump her and spend your energy where it's appreciated. Don't dwell on this friend. History is not enough to create a lasting bond, it only means just that—you and your friend have history—so let her be history!

- The Armchair Psychologist

Need more armchair psychologist in your life? Check out the last installment or emailarmchairpsychologist@swaaymedia.com to get some advice of your own!