Series W interviews Hitlist-01

This week Series W spoke to Gill Morris, founder and CEO of Hitlist, a travel app that makes your hitlist of destinations easier to check off. Morris shared her views on how she differentiated herself from every other non-technical founder with no money trying to attracted a technical co-founder, pursuing the right stage of investors, and the difficult choice of walking away from investor money when the terms changed.

How did you develop the idea for Hitlist?

I lived in Istanbul for a number of years and all my friends said they wanted to come visit. For the first year, none of them did. I started emailing friends whenever I saw a great flight  saying ‘you should book your ticket now!’ and they did, to a surprising degree. We thought a bit about why that seemed to work so well: you had an expert (I worked in the transport industry), who knew you and your particular constraints (because I was their friend), giving timely advice that you had to act on immediately. We thought that a machine would be even better at this, because it would know all the best prices in the market. 

The overall goal of Hitlist is to inspire and enable people to travel more. We want people to spend whatever disposable income they have on travel rather than things. A journey to a new place is more rewarding than a fancy bag or TV: there’s strong evidence that it makes you happier and healthier, but it also is more likely to benefit others as you spend money that creates jobs and learn about other cultures. 

How did you pick your co-founders?

I looked for people who were smarter than me, had more experience, had bigger networks, and just didn’t have a project that they were really passionate about yet. 

I really started from zero – I didn’t know how to code, I didn’t know anything about the world of early stage venture-backable tech businesses. So  my first task was to find people who had and figure out how they’d gotten as far as they had.  The universal feedback was that I needed to get technical – ideally learn how to program myself, or bring someone technical onto the team. 

My attempts to teach myself how to code were sort of like a foreign exchange student trying to walk on to the varsity basketball team : ambitious, but also clueless . If I’d had some inherent advantage like being 6’5″, or having a background in mathematics, it might have made more sense to continue down that path. But teaming up with someone who had already been doing this kind of stuff for years would allow me to play to my own strengths. 

I thought about how I could differentiate myself from every other non-technical person with no money who wanted to convince a highly skilled person to work on their idea. One advantage I could think of: I had a great apartment in Istanbul and lots of frequent flyer miles. So I offered to fly someone to Istanbul for two weeks and put them up in my apartment in exchange for some help building our prototype. I ended up having applications from people at Google, Facebook, Expedia, etc… but the one I ended up choosing is my cofounder to this day. 

You pivoted from another idea to form Hitlist – what was it that made you make the switch? 

We spent a year building Tripcommon, a flight finder that would help you plan trips with friends. The more we built the more we began to feel like we were building a niche product that wasn’t relevant to a broad base of users. Plus after a year of trying really, really hard, we had only gained around 9000 registered users and barely any active users. The market told us that they didn’t really want what we had built. Of course if we’d been more experienced we probably could have pushed the idea further but we had also started working on Hitlist and felt like it was a bigger opportunity. 

How did you get your first investors on board? What would you do differently?

Lots of trial and error. I don’t think there’s any substitute for just hitting the road. I made a target list of investors based on who had invested in travel previously, who had invested in companies I liked, and tracked down introductions. In retrospect, I spent too much time at the beginning with VCs, who weren’t realistically going to invest in a nascent product with an inexperienced team. I should have just stuck with angels who I could sell on our vision. Also, I find people who have founded companies themselves to be the best mentors / advisors / investors. 

My first outside investor was the Chairman of Orbitz, who I met through another founder of a travel startup. In general the best introductions come from founders who are already making an investor money, followed by investors who have put money into your business telling their peers.

What has been your greatest WFIO (we’re f*****, it’s over) moment so far?

I don’t think that we’ve ever had a WFIO moment. But probably the low point so far is when an investor who had promised to lead our round tried to change all the terms on us and I had to make a choice between accepting his terms and having $1.3m in the bank or walking away and not having enough to make payroll the next month. We walked away but it definitely changed our trajectory. 

What has been the most exciting moment so far?

Every day gets more exciting. The first day that we passed 10,000 downloads in a single day was pretty heady. But just knowing that there are thousands of people out there using our app, discovering new places to go, and booking tickets is tremendously exciting. If I had a billion dollars I’d be doing the exact same thing.   

What is your favorite placed you’ve visited? Favorite place you’ve lived?

Georgia (the country). The people, the food, the history, the scenery, are all so unique and underappreciated. There’s also a unique musical tradition. I met a diplomat in the hot tub of a Soviet ski resort who invited me to join a rehearsal for a local choir and go out for drinks afterwards. That night remains one of my favorite travel memories of all time. As far as places I’ve lived, Istanbul was wonderful for quality of life, but there’s nowhere I’d rather be than New York City. 

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