“You Never Fully “Clock Out” When You’re Starting Up A Business” With Jennifer Fein, Bron Thulke, and Caitlin Wynne

Yitzi Weiner
Mar 27, 2018 · 10 min read

I had the pleasure of interviewing Jennifer Fein, Bron Thulke, and Caitlin Wynne, Founders of YouLi , the digital platform that is making big waves in the travel industry. The three women are passionate about travel and technology, and lead a team that is building tools to make it simpler for organizers to create transformational group travel experiences. Named by Huffington Post as 2017 limit-breaking female founders, their travel management platform has powered Hacker.Exchange trips to bring people to Silicon Valley to become entrepreneurs, Humankind Enterprises trips to take people to Bhutan to learn about slow change, and even Jennifer’s own trip to lead a group climb up Mt. Kilimanjaro. YouLi’s vision is to make it easier for people to experience the world and empower them to bring others along.

Thank you so much for doing this with us! What is your “backstory”?

Jen: I spent many years working in technology in large corporations, and moved across the world for different projects. After many years building one of the earliest global digital marketing platforms in New York, I led a Product team in the Asia-Pacific region, launching digital marketing products in China, Japan, Singapore, Hong Kong and Australia.

After 15 years, I decided to leave my corporate job to travel the world. I’m a traveler, but even more, I’m a planner. When I travel somewhere, I do all the research to make it super special. In my mind it’s a vivid, beautiful journey, but on my spreadsheet, it’s a pile of dates, numbers and links. I hated emailing around Word docs and spreadsheets that no one read, and I was frustrated with managing disjointed feedback and updates.

I was inspired to make simpler, better tools for people to experience the world and empower them to bring others along. I decided to test my idea with a personal milestone of my own — my destination wedding in Jordan. Most of my closest family and friends had never traveled to that part of the world. Coordinating a seven-day trip for 100 invited guests from all over the world was met with challenges: tracking itineraries, payments, and currency conversions. At the end of the day, my guests loved the ease of their online experience and had a memorable time visiting a beautiful middle eastern country.

I teamed up with my two co-founders, Bron Thulke, our Lead Developer, and Caitlin Wynne, our User Experience Designer, to bring our dream to reality. A shortened form of “you live to travel,” YouLi was borne. Launched in November 2017, YouLi is already providing services to a growing number of businesses globally.

YouLi is a women-led team passionate about travel and technology. We do things a little differently because we know that algorithms don’t know the best places to go. Only humans can create truly transformational experiences. We are building technology to empower those organizers to create the travel experiences that will change the way their travelers see the world.

Can you share the funniest or most interesting story that happened to you since you started your company

Bron: Since starting working on the YouLi team, there have honestly been too many funny stories to come up with a favorite. Every time we get together something seems to happen that has us all in stitches, whether it’s an anecdote about something that’s happened on the weekend, or a dry humor response to a conversation that takes everyone by surprise. I’m proud to say I’ve had the whole team (including non-programmers) super excited about things like successfully pushing a file directly to a cloud storage service, just because we all get involved in each other’s wins!

Jen: As I was descending the summit of Mt. Kilimanjaro on one of the trips powered by YouLi, I watched a man tumble down past me and into one of our guides. Our guide broke his fall and kept him from rolling off the edge of the mountain. I was so nervous I’d end up like him, that I slowed down and took very careful steps. Two of our guides decided that would take too long. They each took an arm and started running down the hill with me, as I limply pinwheeled my legs between them. Alex was a broad shouldered man and Elija was thin and tall. As I watched the terrain fly by, it struck me that I was the Scarecrow being carried by the Lion and the Tin man. I started to sing “we’re off to see the wizard, the wonderful wizard of Oz!”. Turns out they didn’t get the reference, so it must have made them even more worried about how altitude sickness was affecting me!

What do you think makes your company stand out? Can you share a story?

Jen: There are other travel planning apps out there. What makes us different is that we are a white-labelled platform for travel organizers. That means it’s important for us to have our clients’ branding take front and center when they use our tools. We want travel organizers to be successful by helping them deliver a consistent, beautifully branded experience for their guests. Also, since we are a women-led business with a passion for purpose-driven travel, we love championing other women-led businesses who are creating transformational travel experiences!

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

Bron: A big influence over my career in recent years has been Jen, actually. We met a SheHacks hackathon (run by Girl Geek Academy) in 2016, and at the start of 2017 when she asked me to work with her on building YouLi, it was a huge jump for me. To start from scratch building a new project myself took courage, because I had to trust my own skills and abilities to build a solid solution and push my own self doubts aside. Jen constantly encourages me and nudges me towards putting myself out there and blowing my own trumpet a little bit where it counts! We developers can tend to be a very introverted bunch, imposter syndrome is a huge struggle for the majority of us, but there is also a strong community out there who are very supportive and compassionate. If you put yourself out there, you’ll be amazed at how appreciative others are of your efforts in development.

Jen: Besides my incredible co-founders, I couldn’t do this without the backing of my angel investor. He also joined me on the Kilimanjaro climb. When I sank to my knees a few meters from the summit, struggling to get my footing in the loose gravel, he took my arm and said, “You can do this, you’re the strongest woman I know”. I don’t remember a lot of details from the summit climb, but that moment I will never forget.

How have you used your success to bring goodness to the world?

Caitlin: YouLi gives travellers an easy way to travel with purpose. The movement away from pure tourism travel to travelling with purpose is an exciting one and one YouLi is growing.

Jennifer: We are all about shining a light on the creators of travel with purpose, so we use YouLi as a platform to make sure more people know that travel can be more than an escape, it can having meaning and impact. We amplify our clients who are delivering impact more than we could on our own.

For example, one of our clients, Hands On Development, designs trips to create sustainable long term changes for the participants and the communities they visit by focusing on social, financial and environmental sustainability. Their founder, Stephanie Woollard, and her organizations empower women in Nepal through education, training and employment — they have impacted the lives of over 5000 marginalized women.

Do you have a favorite book that made a deep impact on your life? Can you share a story?

Caitlin: One of our amazing clients from Denmark sent a list of recommended books to her travelers, one of which was The Alchemist by Paulo Coelho. I quickly grabbed a copy and read it in a weekend. This book is simple and yet powerful in giving you a perspective on life that we may have forgotten over the years or may never have considered. Follow your dreams with purpose and enjoy being in each moment of your journey.

Bron: On a personal level, I recently got back into reading for the first time in over 5 years (having young children pretty much killed my “free time” or a while!). One of the first fiction books I read last year was “Eat, Pray, Love” by Elizabeth Gilbert, and it had a big impact on my mindset for life, as well as injecting a newfound interest in travel and experiences. Since reading it we’ve started a trend of organizing at least one trip away every school holidays (even if it’s just to somewhere nearby for a night or two). I’ve convinced my husband that we should start camping with our girls, and I’m looking at options to take our adventures overseas in the next couple of years!

Jennifer: I wish I could say my favorite book was In A Sunburnt Country by Bill Bryson since I now live in the land he so amusingly traversed. But as much as I love his books, I often return to Tao of Pooh by Benjamin Hoff. I think I tend towards being a “bisy backson” (like the Rabbit in Pooh) and I love how Hoff weaves the familiar Pooh characters into his explanation of the Dao de Ching. I find a lot of value in Eastern philosophy and Hoff has made it very accessible. When I feel I’ve worked myself into a “bisy backson” state of mind, doing too much and accomplishing too little, I re-read the Tao of Pooh to center myself.

What are your “5 things I wish someone told me before I started my company” and why. Please share a story or example for each.

Jennifer, Bron and Caitlin:

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this. :-)

Jennifer: We applied for an Oprah casting call for Female Entrepreneurs ready to take their business to the next level. We didn’t make the cut, but I would love to have the chance to meet Oprah. She’s been a larger than life figure for me while growing up, and I respect how she’s persevered through various stages of success to become an even more powerful symbol today. I accidentally built an all-female team, an oddity in the startup world, but I wonder if it is actually a sign of the new dawn that she talked about. Maybe we are closer than we think to a day when we see it as normal when women come together to create businesses that change the world.

This was very inspiring. Thank you so much for joining us!

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If you would like to see the entire “5 Things I Wish Someone Told Me” Series In Huffpost, ThriveGlobal, and Buzzfeed, click HERE.

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