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.”

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Why Don't Enough Women Support Each Other in The Workplace? (and why they should)

Why don't women support each other? A question that I often ask myself, and is not easily answered. I keep reading articles about why women should support one another; and I'm sure many do, but more than likely, not enough. I have typically not had that experience, I wish I did more, because I enjoy the banter between women; I have a lot of female friends, and four sisters. I relish in supporting other women; I have mentored teen girls, and loved doing it; to the point where some of the teens I have mentored, to this day, still keep in touch with me. It makes me feel really good, and this is why it is so vital to everyone concerned.

A few women bosses I have had in the past, seemed to have their own agenda. I had seen, of course, bullying. And other behaviors such as being set up to fail, and as in my previous article; being followed to the bathroom, constant monitoring, given unreasonable expectations, belittled, and treated as a subservient. One former boss even suggested I take former convicts in my car, to help me move boxes; was that for real? These behaviors have lasting effects on a person's psyche; not at all fun! Why do other women want you to feel inadequate and incapable? It makes me sad when I think about these things. It's really a win-win situation to support one another. Working as a team promotes healthy work relationships and is conducive to work being accomplished in the workplace.

I may come across as biased, but it seems to me in my experience that is is easier to work for a male. Just about every single male boss I have had, was upfront, approachable, and did not have a hidden agenda. I tend to think with a man, "what you see, is what you get" (but as with everything else, not 100% of the time; because I was told by someone close to me that her boss ( a man was "the devil"). However, I can honestly say, that I did have the pleasure of working for some wonderful female bosses who possessed the same qualities. But in considering the length of my career, not too many. When I think back, I only have fond memories of these women.

I enjoy it when friends, acquaintances, or one of my sister's tells me that she has a good woman boss; it am so happy to hear this. I say to myself that they are fortunate and to embrace it. Today's women have so many expectations on them, and working a full time job as a boss, can be intimidating I guess in several ways. They feel they have to work harder, longer, and have more to prove; they want to look good for their boss, and the company they work for. I have felt that as well.

As I feel as with bullying, employees who bully (in general; or in the workplace), must not feel very good about themselves. I feel secure enough in myself, (I genuinely like myself as a person), so I would not engage in these tactics. I have seen so much "nonsense", as I call it in my working career thus far. Game playing, you name it. It really makes me wonder what is going on? One former boss in particular, would weasel their way out of doing just about anything. They were paid enormously well, knew just how to manipulate people working them to somehow do their job, and make themselves look good in the process. They took pleasure in holding you back; not letting you ever get ahead. Gave their staff a hard time when it came to time off, but they would take a month off to travel overseas.

As I said before, there was an agenda. They were all about themselves. But the good news is, that after they left the company, all was discovered, along with many other infractions, and they would not be allowed to return to the company. I have said this before, and truly, truly, believe it, "what goes around, comes around", This person was very much disliked and consistently used big words to make everyone around them, seem as if they were stupid; and they were superior - please! What a way to go through life!.

When I had a 'not so nice' boss (in general), I actually felt like I didn't want to do my work, and well while I had to, didn't care because I wasn't being supported or heard. Which is not good for the company you work for, or for yourself especially if you are one who takes pride in their work. You often end up leaving your position (transferring to another department), getting another job, etc...what a hassle. When I've had bosses who actually listened, cared, and supported me I did better work and in general felt good about myself and the work I was doing. Makes sense, right? I wish more women would think about the way they act and treat others. It would be so much easier, and more pleasant. Working is hard in itself, and to go to work everyday, and not be listened to or supported really stinks. So, after all is said and done, it really is better to be kind, understanding, and actually listen to your co-workers. So much good and so much more can come of it. I know when I was in charge of being the boss of other women, I always paid attention, cared for them, and was understanding and never set them up for failure. I hope again in the future, I do have a women boss, and I hope she will show me the same respect as I would show her.