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

Yitzi Weiner
Thrive Global
Published in
10 min readMar 27, 2018

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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…

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Yitzi Weiner
Thrive Global

A “Positive” Influencer, Founder & Editor of Authority Magazine, CEO of Thought Leader Incubator