11: Taking Risks & Rising Together

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In this episode, I’m joined by Gillian Morris, co-founder and CEO of Hitlist, an app that alerts users when flight prices drop (and has two million users!). 

Before entering the startup world. Gillian worked as a consultant and journalist in Turkey, Afghanistan, China, the Gulf States, and Syria. Gillian's diverse travel experiences have taught her early on how to take risks and be okay, no matter the outcome. That has helped her become the brave entrepreneur she is today. 

Gillian has also tried a lot of different things in her path, like being an opera singer in Paris and living in an artist residence in Istanbul.

In this episode, we talk about why the pressure of figuring out who you want to be when you grow up is not all that it's made up to be.


“I believe stepping into our genius means taking risks and being willing to put yourself out there and to the degree that you can support those who don't have the same ability to take risks that you do.  So  I think womxn very much rise together. It's very important to help each other out, to reach out for someone to extend a hand to you who's ahead of you, but also to reach behind you and make sure you're pulling people up at the same time.”


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“Travel teaches us that there are so many different ways to be successful, or to be beautiful, or for something to work, you know?  And it's going to be very much in the eye of the beholder. I'm sure there are some people who would make an argument that I should have swallowed the bitter pill, I should have swallowed my pride, given up a little bit of control and built a much bigger company faster.  That's one take. And then, I took the take that has ended up in this very different path.”


Want to know how you can start publishing your travel stories? Download my step-by-step guide to publishing your stories and start sending your ideas out into the world!

What you’ll learn in this episode:

  • [03:08] Early childhood dreams of becoming a cartoonist

  • [08:57] Gillian’s journey in discovering her unique career in travel and tourism

  • [11:33] Gillian’s thoughts on why the travel and tourism industry brings a positive impact on the world

  • [16:24] Gillian sharing school with Mark Zuckerberg and what inspired her to learn and get involved with technology

  • [19:25] Why traveling and taking risks early on in her life gave Gillian the confidence to start her own business

  • [21:26] How the Hitlist app works and unfolding the truth about the best day and time to book flights

  • [23:10] The journey of building the right team to start and grow Hitlist

  • [25:51] Gillian’s blog posts about everything Istanbul

  • [27:28] Talking to 323 investors and the issues Gillian experienced raising money for Hitlist

  • [28:44] The Middle East not commonly seen in the western world

  • [33:13] Gillian shares her stories of persistence while encountering rejections from investors and problems with business partners

  • [42:14] Gillian reflects on a ride on the Trans Mongolian Railroad where she read a life altering quote in a magazine

  • [44:10] Being hopeful and optimistic in these unprecedented times and turning the situation into a eucatastrophe

Featured on the show:

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