Startup Spotlight: Wanderful

Nov 11, 2018


Startup Spotlight: Wanderful

Nov 11, 2018

Meet Beth Santos, Founder and CEO of Wanderful, the startup that’s created an inclusive and collaborative community of women travelers!

GH: What is Wanderful?

We are a community of over 40,000 women who love to travel the world. We host two annual global conferences to connect women travelers to the resources they need, run more than 30 local Wanderful chapters to inspire sisterhood across the globe, create content that dives right into the issues women travelers face, lead trips for women to destinations around the world, and run a women-to-women home-sharing network.

GH: What was your Eureka moment: how did Wanderful get started?

After graduating from Wellesley, I moved to Sao Tome and Principe, a small Portuguese-speaking country off the west coast of Africa, to teach computer science at a school. It was there in this small country with a population of about 150,000 people at the time that I became very aware of myself as a foreigner living a very hyper-local experience. I loved living this global life, but I also felt lonely in other ways. I didn’t realize that so many women were traveling the world on their own like I was.
That was in 2009. Fast-forward to today, when 11% of the entire travel industry is made up of solo female travelers, and two out of every three travelers are women, and you realize that women’s travel is not even close to being a niche. Yet still there are a number of issues very unique to women’s solo travel that we’re forced to navigate — cultural norms and gender expectations; safety (and the still-present narrative that many solo female travelers are told that they shouldn’t be traveling alone at all); even our bodies (pregnancy, maternity, menstruation — Thinx and the DivaCup are all the rage in the women’s travel community).
What I realized was there was a wealth of information out there, but because it’s travel, it’s always changing. But what if you could get the right advice — and a friend to help you out — in real time? That’s when Wanderful shifted from just content to actually activating a live network of women around the world who could help each other. We have forums for people to get travel advice, run women traveling solo workshops, and empower our travelers to host one another in their homes through our woman-to-woman home-sharing network.

Beth Santos, Founder and CEO of Wanderful

GH: How did you build your team?

We have always been extremely purposeful about our team. We started from very meager beginnings as a travel blog, and have yet to take in outside funding. Because of that, many of our hires started from people who started by only putting in about 10 hours per week with us as contractors, and then increased their commitment as time went on. Looking back, it was a great strategy — it has allowed us to test drive each and every team member to see how they actually work, and helps avoid those uncomfortable situations when you hire someone only to realize that they were the wrong choice and now you have to backtrack.
There’s a level of commitment on their end too — if someone is coming onto our team working only 10 hours, you know that that’s not enough for them to earn any meaningful income, so their willingness to do it anyway shows their dedication to the startup environment. We really try to help everyone on our team to find freelance opportunities if they need it, and support a flexible working life, so that if they’re the right fit for our team, we can make this work for them.

GH: What is your company philosophy driving your company culture?

Wanderful is very unique in our company culture. That’s because of two reasons. First, culture is everything for us. As a company that was centered initially on the creation and growth of a hyper-engaged community, our company culture very directly trickles down to the experience our users get.
The second reason that this is particularly unique is because we are also a virtual team. Everyone on our team works from home (or a coworking space, or a hostel in Nicaragua). So we have the unique responsibility of needing to create and disseminate a strong community culture while also not actually having a whole lot of face-to-face time. That’s why for us, having an exceptionally collaborative, respectful, and nonjudgmental working environment is very important. We pride ourselves on being a sisterhood of kind, helpful women, and it is our responsibility to demonstrate that behavior with each other. That doesn’t mean that we are all the same, or that we always agree. In fact, quite the opposite. But we practice respectful dialogue, lean in to hard conversations, and ask that our community does that too.

GH: Startup life is full of failures and ‘make it work’ moments – can you identify how you bounced back from one of yours?

I think we often hear about startups that had this one “make or break” moment and suddenly turned things around and now they’re making $1B in annual revenue. But it’s actually not like that at all. There’s not one make or break moment. There are thousands of them. Some of them actually won’t break your business, but in the moment it sure feels like they will, especially when your company is very young and volatile. Literally every day is filled with ups and downs, and it’s your job to constantly learn from them.
We run an annual conference for travel influencers and industry called the Women in Travel Summit. I remember our first year when I was learning what it took to plan a conference. It was a few days before the event and we got hit with this enormous bill for the audiovisual that we were not expecting. I didn’t know what to do — we didn’t have enough cash in the bank, nor did we have a big enough credit card limit. It’s not like we could cancel the conference. I remember nearly crying while on the phone with my bank trying to convince them to increase the credit limit on my company card, but as an Internet business with no assets we didn’t really have much to offer for collateral. I got off the phone and immediately started making calls. I closed three sponsorship deals in one week and brought in an extra $20,000 in sponsorship money. Just one after the other. What else could I have done? My friend said to me, these are the moments when we really find out what kind of entrepreneurs we are. Do we get things done? Or do we fail and close shop? I decided I just needed to get it done.

GH: What did you learn from your first customers?

That your earliest customers are in it as much as you are. The good ones — they will follow you and they pivot with you. They’ll continue to give you feedback, years later when you feel like they must be tired of your questions. They take a certain pride being the “early users” and we celebrate them as often as we can.
Our early users have really helped us evolve as a community over the years. We have a series of Facebook groups — one for each chapter, and a global group for people to trade travel tips. There were times we thought Facebook was going to get rid of anyone’s desire to attend an event in person. But now we’ve found that it actually strengthens it. People meet each other in our Facebook group and then they crave the opportunity to meet each other and exchange ideas face-to-face. So being in close touch with them over the years has given us a lot of personal experience with macro trends and has helped us to identify them before they happened.

GH: What has the Boston ecosystem provided you?

I’ve been living in Boston for two years now. It’s very different from Chicago, which is where I started Wanderful. Chicago is a big city that’s very spread out. Boston is a much tighter community. That can be a good thing (when people like you) and a not-so-good thing (when people don’t). But it is what it is. I was fortunate to join the Babson WIN Lab shortly after moving to town. It was an incredible introduction to Boston and I made amazing connections not just with other founders but with people who would be advisors, mentors, friends and professional connectors. I’ve really enjoyed meeting the amazing people here who believe not only in changing Boston but in changing the world. I’ve met them at events by She Geeks OutThe Capital NetworkWE BOS week and other gatherings.
Earlier this year, I started a new company called #AtTheTable with Rica Elysee, a fellow Boston founder. We found that despite all the tools available for women entrepreneurs here in the city, there was still the need to make intimate, authentic connection and conversation with other women in the startup world. I can’t tell you how many times I’ve met another founder here who told me I was the first other female founder she’s met in Boston. The FIRST ONE! That means we still have a long way to go, but I truly believe that Boston can be the best city for female founders in the country if we let ourselves.

GH: What is the Boston ecosystem lacking from your perspective?

Unfortunately, we’re not there yet. I was astounded by a statistic I learned at an event recently that less than 10% of venture-backed companies have a woman on their founding team. That means that over 90% of companies that get VC funding are all-male teams. That’s not just a Boston statistic; that’s an everywhere statistic. Only  20% of firms with paid employees are owned by minorities, black women only receive  0.2% of venture capitalwomen founders are often excluded from tech awards, and  Massachusetts is 46 out of 50 in terms of states supporting women entrepreneurs.
The City of Boston, professional organizations, and many VC are taking steps to close these gaps, which is really exciting. We’re seeing a lot of initiatives pop up to support female founders and get them pitching, and that’s great. But we’re still not seeing the needle move in terms of how many checks are written. That’s a problem.

GH: What’s the best/worst piece of advice you were given along the way?

The worst advice? That I had to decide if I wanted to focus my time 100% on being an entrepreneur or 100% on being a mom. I have gotten that advice twice.
The best advice? Maybe not so much advice as a comment. I once had a career coach look deep into my eyes and say to me, “Beth, there is absolutely no reason why you cannot get everything you want in the world.” In that moment, I felt completely empowered. Oftentimes I think about that moment before I deliver a big pitch or a sales call. I remind myself that there’s absolutely no reason I can’t get what I want out of this life. I have a great head on my shoulders. I’m thoughtful and confident. So why not just go for it? Those words have carried me when times were hard (and I have felt less thoughtful or less confident).

GH: What was the best thing that happened to you last year?

Last year I gave birth to my daughter, Nora. I entered a whole other world at that point — the world of being a mother while also running a startup. A very challenging road, to say the least, and one that we need to be talking more about as a society, by the way.
Just a couple days before giving birth I found out I was accepted to a pitch competition. I actually worked on my pitch in the hospital. Five days after giving birth to my first child I squeezed myself into a pair of nylons, slowly maneuvered myself on stage and pitched my heart out. I won second place. I went home and slept. I used the money to help pay my team while I was on maternity leave.

GH: What does the future hold for Wanderful?

We are putting our women-to-women homesharing platform to work for the 2019 Women’s March. We are activating our network of tens of thousands of women globally to connect women traveling to the 2019 Women’s Marches with local hosts.
To do this, we’ve created a free service that pairs marchers needing a secure place to stay with trusted women who have extra bedrooms and space in their homes. We believe it’s our responsibility as women to help each other travel the world, which is why we want to make sure no woman feels like she can’t march because she doesn’t have a secure place to stay.

Learn more about the Wanderful!

*pictures are courtesy of Wanderful’s website

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