Lots of people love to travel, but how do you turn a hobby into a real business? Gillian Morris had a full time job in Istanbul and she figured out that she could get her friends to visit her there if she found cheap flights for them for specific dates. Soon, she was getting weekly requests from dozens of people to send them cheap flight deals, taking up nearly all of her free time.
In part one of our two part interview with Gillian we learn how she was able to turn her idea into a real business after deciding to attend a conference in Europe that would lead to a press release that grew her user base to 25,000. Gillian talks about how as a first time founder she had to learn everything, from how to build a product and understand user data, to marketing and learning how to talk to investors.
In part two you will hear how she ended up getting her first investor, what she did to monetize the app, and why she decided to build a distributed team at Hitlist.
1:38 – Vadim: I was introduced to Gillian by a good friend of mine, Emily who I work with now at the NYU Entrepreneurial Institute.
1:52 – Sergei: Apparently you live on a barge somewhere in San Francisco or outside of San Francisco? Tell me about that.
2:00 – It’s a retired car ferry that used to run around Iceland. I was not officially living there, no one officially lives there. It was a place where we had a number of people monitoring it because insurance requires that we have someone on the boat 24/7.
2:56 – Sergei: Do you the history of how that car ferry boat started?
3:00 – I do know the history of that particular car ferry.
4:10 – Vadim: What lead you to start Hitlist?
4:12 – I was living in Istanbul when I started Hitlist. Moved there after graduation working all throughout the Middle East and Central Asia.
4:27 – I was a journalist, I worked briefly for CNN. And then I became a consultant and worked on security projects for the most part.
5:08 – I didn’t feel like I had any real impact but I learned a ton. I like to think of it as my master’s degree that instead of paying for, I got paid very well for.
5:40 – I always loved to travel. And I would always try to get my friends to come and visit Istanbul.
5:48 – I wrote this script that would do hundreds of searches every day and every time I would find good cheap flights to Istanbul; I would send them to my friends.
5:58 – Vadim: Were you a self-taught engineer?
6:04 – Yes, I learned using Code Academy and just by talking to other developers.
6:36 – I think it’s very common in the tech industry. People are excited when you are trying to build something and they’re happy to help.
6:47 – Vadim – Did you learn with the actual intention to build something? Where did the curiosity to learn how to code came from?
6:53 – I definitely was interested in building something.
7:15 – I had a lot of friends who had started companies and the tech industry is something that is really interesting.
7:23 – Vadim – So you’re in Istanbul, you’re learning how to code. Trying to figure out what’s gonna be the next thing for you and you’re trying to make your friends come to Istanbul. How did this turn into a business?
7:40 – I noticed that all these people said they were going to come and visit Istanbul and then they didn’t. But then when I started sending them emails saying, “Here’s an amazing flight deal, you should book it!” they would. 4 out of 5 emails would book the flight.
8:44 – I noticed that friends started asking if I can you let them know when there are cheap flights to San Francisco or to London, So I started expanding this in a spreadsheet and it was taking too much of my time.
9:00 – Meanwhile, I actually started working on a different idea with friends and I was building this thing called Tripcommon. And that wasn’t really going anywhere.
9:26 – Vadim – So when you were thinking about the other idea, were you spending more time on this side project spreadsheet that you were managing or this new idea?
9:36 – I definitely was spending more time on TripCommon to start. At that time, I’ve been thinking about it for 6 years and I have always wanted to have this tool.
9:54 – I had entered a hackathon with a friend and we won that. It was really a great first step. And we were building TripCommon for 9 months, but it wasn’t going anywhere. No one used it.
10:30 – We eventually switched to Hitlist, pretty much everyone is interested to receive an email when prices dropped.
10:40 – Sergei – Once you decided to pivot into that business, how did you start growing your user base and what was the next step there?
11:03 – I had no idea what I was doing.
11:15 – Our real breakthrough came when we were at the conference called Web Summit. And a reporter from The Next Web wrote a piece about Hitlist.
11:45 – Sergei – It started off as a newsletter, right? It wasn’t even an app yet.
11:52 – It has a newsletter like component, but it was more of a one to one and it was totally personal. But we knew we wanted to make it self-service.
12:05 – Vadim – You decided to go to the Web Summit, was that something that you planned?
12:21 – I got a targeted email inviting me to pitch for a pitch competition and there was a chance to win 50,000 USD and get some exposure.
13:10 – Vadim – Do you remember at what point when you were managing this one on one that you decided that you should build an app to help scale this.
13:45 – We were at this point where we knew TripCommon wasn’t working out. One afternoon we mocked up what the app would look like. From then, we built it relatively quickly.
14:18 – How many user sign ups did you have before Web Summit?
14:25 – About one hundred.
14:30 – So it was pretty much growing organically. What’s the timeline there? You got back from the conference and the article was written? How long did it take for it to actually come out?
14:41 – The article is written at the conference and it sort of sparked the series of exposure. A random Greek blog picked it up and it was clearly an impactful Greek blog.
15:15 – Overnight you got all of these users, what did you do? Did it crash your server?
15:20 – It didn’t, and this is a huge testament to my co-founder who engineered something that was able to scale.
16:45 – You got all these users and you have to build a bunch of functionality. Did you know how to manage product at this point?
17:01 – We both were very much learning as we went along. I was the product manager and he was the head of engineering.
17:36 – So how did you figure out which features to build and when? Did you talk to users at that point?
17:41 – Yes, looking at the data and talking to users is very important.
18:44 – What is the right amount of data to have? Did you have to wait for a certain amount of users to know whether the data is meaningful?
19:00 – You do need to have enough data to go on.
20:00 – Were you able to get back to people? Did they leave their email address so you can still market to them?
20:00 – We didn’t ask for their email address early on but then we started to.
20:45 – To this date, we don’t require any email address or anything like that.
21:00 – What was your idea to grow your audience? Also, did you think about fundraising at this point?
21:44 – Absolutely, we did fundraised at this point with the initial 25,000 users and we used that to completely rebuild the app.
22:50 – We release the app and we started contacting the press.
23:00 – 2 important points where you can always get coverage and that is initial launch and coming out of beta.
24:38 – Tell us about that fundraising experience. How did you go about it?
25:01 – I always say that the best introductions from investors come from other founders that the investors had invested in.
25:35 – I built up a list that I wanted to target through AngelList and my own research.
27:20 – Vadim: So you made a list targeting people that you thought are going to be travel-friendly.
27:24 – Yes
27:50 – Vadim: So how many do you think you reached out to, how many meetings you think you had to have before you got people to invest?
28:08 – I haven’t actively fundraised in a couple of years, but I’ve talked to 325 investors. And I talked to over 100 before I got my first yes.