How A Travel Idea Turned Into A Multi Million Dollar Business With Scott Keyes

On today’s show, we have Scott Keyes. He is the founder of Scott’s Cheap Flights. This is a website that allows people to be alerted when super cheap international airfare pops up. It began as an informal hobby with him and his friends in 2013, before opening its doors to the public on August of 2015. Scott’s Cheap Flights currently serves the United States, Canada, Latin America, the Caribbean, all of Europe, Asia, Australia, New Zealand and soon to be, Africa.

April 24, 2018 43 mins Download (MP3)


01:50 Imagine you just had the best day of your life. Where are you going to eat, and what are you ordering in order to make your day complete?
04:56 Tell me about a time you felt lost or blind in business. What was it like, and how did you overcome it?
08:10 Could you tell us briefly on how you started the business?
11:41 What were some of the ways in which you were able to obtain your first 100 customers?
16:10 Now that you have this base of constant referrals, do you see something in future that you could possibly hint at, or would you rather keep it in the ‘real’ space of just genuinely helping people?
18:39 Was any of this philosophy regarding work and life; was there any inspiration from it?
23:08 What was it like to find a well-known magazine with your face on it?
24:37 There’s this picture of you with your business partner here. Is he your core business partner?
28:05 There’s this picture of you in what I believe to be Japan. What was the experience like?
30:51 Are you a huge wrestling fan?
32:38 With the current state of the world, and Americans in particular, is there anything that you wish that, being a world traveler, Americans could take with them to those that may not have traveled before?
35:20 The Blind Entrepreneur podcast was created for those individuals that may be temporarily blind in business. To those individuals, what are 3 pieces of advice that you could share with them?

How Scott Keyes Obtained His First 100 Customers

What I had at the time was this list of 5,000 emails from persons that were getting the service for free. But as you know, it can be quite difficult to convert these into customers that are willing to pay for the same service. I was then contemplating whether I could get even a fraction of this list to start paying for the service. What I ended up doing was employing a freemium model – premium members would get more deals whereas free users would only get a third of them, there would be no ads bundled with deals for premium members, things like that.

In addition to sending such an announcement out, I also set a very low price point in an attempt to get people to actually pull out their credit cards for this. I initially set a goal of 20 persons by the end of my first month. Not only did I surpass this goal, I was actually closer to 100 signups as well. As the months went on, the member list kept growing and the recurring revenue was always a welcome bonus to the growing email list.

One thing that I also tend to do is put a little teaser in all free emails to encourage people to upgrade to a paid membership – usually it’s in the form of showcasing a paid member that saved significantly on a trip. That way, I can show free members what they might be missing out on, but simultaneously not pressuring them to buy.

Three Pieces of Advice From Scott Keyes

First, it’s super important to find that product/market fit before you head all in with your venture. I find entrepreneurial subreddits with people talking about wanting to quit their job and start their business, etc. Find some way to make it a side hustle – what you may have in mind may work, but you need to tread lightly. There’s a good chance that you may fail at first; you need to have a contingency plan.

For me, it took up to 6 months for me to stop freelance journalism and go all in with Scott’s Cheap Flights. Another thing I find important is thinking about your voice and overall branding. People like when companies act as people as opposed to corporations. Be warm and humane in your correspondence – try to avoid being too boring. Lastly, you will want to find mentors or role models that are in the field you’re interested in so that you can get questions answered, as well as advice. But this may be difficult due to their schedules. If you are just starting out and you want these mentors’ attention, keeping a blog or podcast is a great excuse to get the opportunity to converse with them.