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Building A Successful Travel App In A Competitive Market With Gillian Morris Of Hitlist – Part II

Part II of our interview with Gillian Morris starts with a cautionary tale about taking people for their word, and why a potential investment is never real until you have the money in the bank.

As with every obstacle in her entrepreneurial path, Gillian quickly learned the complicated and sometimes cryptic landscape of dealing with investors to raise more than half a million dollars in her first round.

In the second part of our interview Gillian talks about how she dealt with a co-founder leaving, and how her team ended up monetizing Hitlist to turn it into a profitable company. We also dig into her how her job changed when the company had to adjust its focus on sales, and why she made the decision early on to have a distributed team with no central office.

Show Notes

29:40 – My first investor was actually a friend, who is a lawyer who I met when I was an Opera Singer in Paris.

31:06 – I got this meeting with the chairman of Orbitz through a fellow founder.  I sat down for breakfast with the guy and within 15 minutes he said, “Yea, I’m in for 25 maybe 50k.”

32:31 – Yea, I think a lot of people don’t realize that first of all it’s very difficult in the beginning. You want money and you need money to finance the company, but eventually you can find people that are willing to bet on you.

33:05 – At this point, were you planning on monetizing the app as well?

33:12 – We were already monetizing the app. I think we are making around 80 dollars a month.

39:10 – 2015 was a tough year.

39:13 – So why do you think you were able to make it past that and how were you able to?

39:24 – At that point, it is clear that we needed some money.

39:52 – So at that point, we were 3 people and we just focused on generating revenue as a priority.

40:29 – There were points where we have credible investors coming in saying they are really interested to invest. At that point though, it didn’t seem relevant anymore because why would you give away a big chunk of the company.

41:05 So you mentioned that you moved to Puerto Rico and I am curious, can you give us a little bit of an idea of where the business is now? Is it a distributed team? How many users are you at? What happened, ultimately.

41:20 – We are a distributed team. My main consideration was, I didn’t have to be in San Francisco anymore.

41:45 – At this point, the company is profitable.

42:20 – I’ve been staying in different places in Puerto Rico.

42:50 – It sounds really cool that you’re there. I didn’t know that it was an emerging tech hub though. It’s that true?

42:56 – Absolutely! Right now it’s known as the best place to be if you are a crypto investor

44:05 – After you shifted your mind frame and started focusing on creating a sustainable business, how did your work change? What did you start doing more of and what was your focus?

44:20 – Sales. I hate sales.

45:28 – Your life changes because what you’re doing now on a daily basis, you didn’t want to do. How did you get past that?

45:54 – It turns out that there are people who actually like sales and who are great at sales, so I focused on finding those people. I think the reason why I hate sales is that I don’t think I’m good at it.

46:42 – You can hire someone out, but you can’t do it until you intimately understand what that thing is by trying it yourself. Do you agree with that?

46:48 – Actually no. Our first sales person was someone who’d I hire as part-time marketing. And she was the one who devised our entire B2B strategy.

48:12 – Where there moments when you had massive spikes or was it kinda a little bit more linear?

48:18 – We had massive spikes, but I wouldn’t say they were necessary because of our technical product decisions. Because Apple can feature you. When we got our first Apple product feature it got 104,000 downloads in six days.

48:47 – Did they choose you or was there a process?

48:50 – They chose us.

49:43 – And you have an android app now too?

49:44 – We do. I will admit our android app has some flaws. It’s not as great as our iPhone App.

50:29 – What’s next would you say for Hitlist and what is your focus? Your team is distributed now, right?

50:40 – It’s always been distributed to a degree. We get together periodically.

51:00 – What’s next for Hitlist? We started developing now a premium product which is a subscription upsell.

54:15 – Create the business you want to create. There are going to be difficult times, but it is a beautiful learning experience.

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