Everyone likes the idea of going on a spontaneous adventure but when flight and costs get in the way, the once great idea turns into just a dream. Seeing all of your “must-see bucket list destinations” just got a lot easier. Rama Poola, CEO of SkyHi is ready to turn your dream  into a reality by making it easy for you to claim seats on flights all over the world for one low monthly price. As a traveler himself, he knows that some of your best adventures are the ones that are done on a whim and he’s ready to help you make the best memories of your life!

Tell us about SkyHi.

SkyHi gives travelers a seamless, on demand way to claim empty seats on commercial airlines for a low monthly subscription fee. Members can see flights leaving within the week, flying to destinations up to 1500 miles from their current location. Flights are one-way and a user can only hold one ticket at a time. SkyHi is creating a new way of thinking about travel by providing freedom and spontaneity for everyone. Our clientele is young professionals with job flexibility and some disposable income. Freelancers, creatives, gap year students, and even early stage startups can benefit from a service like ours. The first time I booked through  SkyHi, the process took 30 seconds from not knowing where I wanted to go, to having a ticket in my email. This is a huge win, since making travel plans usually takes me hours before I book a flight on traditional OTAs (online tour operators).

What experience did you encounter that helped you create SkyHi?

I came up with the idea for SkyHi on a trip back from Berlin. I was at the Tegel airport and met a few backpackers who didn’t have a ticket to anywhere specific, yet. They were waiting for a flight that went under 50 euro, going to any of the cities they had on their travel list. They ended up going to Lisbon, Portugal. I got on my plane back to New York and was frustrated to see that it was fairly empty. The inefficiency bothered me and I thought to myself, if the price was low enough, would those backpackers have flown to New York on a whim? I drew up the business model and software architecture on a few napkins, pitched it to my now co-founder the next day, and quit my job the day after that.

How does SkyHi differ from other flight booking apps?

I have yet to come across a flight booking app that has a good user experience. The apps are cluttered, confusing, and not intuitive for a traveler like me. Myself, as well as pretty much every traveler I talk to, constantly change settings/filters to try to get a ticket that is exactly the right price. It takes too much time and is frustrating. SkyHi is dead simple. See places you can travel to in the upcoming week, pick a flight and claim your seat. Every flight costs the same amount of money. All you are thinking of is where and when you want to fly. Flights are one-way only and last minute, so it really is on demand flight travel.

SkyHi went through rebranding at one point. What were the struggles you encountered during rebranding and how has this helped the brand?  

We had to rebrand in the beginning of the year, and at the time it was the last thing we wanted to do. We were heads down building the app, talking to potential partners, along with a whole slew of unknown questions we were trying to answer. The main struggle we had was how do we look at the brand with a fresh set of eyes. We had been operating under our previous name and had become emotionally attached to it. Once we could let go of that, look at the audience we had created, and start to do branding exercises to determine our brand direction, the rebranding effort became really enjoyable.

If you could start over creating SkyHi, what you would you do differently?

Great question. This question is  a bit hard for me to answer. I’m one of those believers in the universe guiding me along my path. I’ve learned things about the travel industry well into developing SkyHi that could have been useful and saved us time and money. However, if I knew all those things up front, I may have never started SkyHi. I may have become overwhelmed by the hurdles. I’m grateful that we’ve hit hurdles one at a time along the way, allowing us to be thoughtful in how we make forward progress without being overwhelmed. I’d say the one thing that would have helped in hindsight is building deeper relationships with travel industry experts earlier.

What do you find to be most challenging about running a company, specifically in the travel space?

I think the biggest challenge is that the industry is very resistant to change. I see so many inefficiencies, but it’s hard to even begin to improve them. Outdated technology and an unwillingness to shift from old ways of doing things makes the industry stagnant and difficult to innovate in. We’ve run into walls regarding regulations, integration with old technology, and have had conversations that ended with, “we know it’s not ideal, but we’ve been doing it for so long.” As someone who has consistently built innovative products, this was both challenging to my personal psyche as well as challenging to navigate as an innovative startup.

How has working in the music industry at SFX Entertainment and Beatport prepare you for life as a CEO?

At my time and SFX/Beatport, I was thrown into handling situations that felt way out of my depth, but just kept trying my best and really grew a lot from the experience. I got to help integrate two very different technology groups into one cohesive team. I got to help craft a reduction in force strategy that was fair. I got to think of large scale problems in the music industry and think of solutions. I got to be a part of hiring practically every new member of the technology team. Overall, what I really learned was how to properly grow a team of talented people while holding and sharing the overall vision. So, in short, it was the exact preparation I needed to become a CEO.

During your time at Arc90 you led the startup Readability. What hurdles were you able to foresee and avoid due to this experience?

Readability was one of the more difficult products I led. Mainly because I was still so green to having so much responsibility. Readability was a small team with a small budget and a short timeframe to launch. The team was talented and all had strong personalities. At times, I felt that I didn’t have enough to offer and was often indecisive when it came to important decisions. What I learned from that experience was how NOT to be an effective leader. In the products I led after Readability, I was more cognizant of how to effectively motivate team members, how to hire properly, and how to be decisive. I carry all that experience now as the CEO of SkyHi. We have been able to build a team that works well together and have been able to take a product to launch in a notoriously difficult industry in roughly 18 months.

Do you have any mentors or people who have deeply influenced you to become the entrepreneur you are today?

Many of my mentors are family members I’m first generation Indian-American. My parents and immediate family immigrated here with nothing and have all had incredibly successful careers. I’d say the most influential person I have in my life is my older brother. He paved the way for me as a kid, supported my crazy endeavors, believed in me, and instilled me with a positive outlook on life. He’s also been incredibly adventurous with his life direction. He’s currently living in Berlin with his wife and baby daughter while attending wine school in London. Just three years ago he knew very little about wine and now is writing for one of the most prestigious wine publications and being flown to vineyards around Europe. He constantly reminds me that I’m capable and deserving of doing what makes me happy.

If you were going to book a flight using SkyHi today, where would you go and why?

The first place I want to go to is Montreal. The food, architecture, art, and culture really appeals to me. I’m also a bit of a Francophile, so anything that’s French influenced draws me in. As close as it is to NYC, I haven’t been to Montreal since I was a child.

What are some of the main goals you most want to accomplish in your professional career?

Around the same time, I was starting SkyHi, I was exploring the possibility of starting a company to help the tech community in Kenya. Over the past few years, I have been following the tech community there and have really been drawn to how they are solving hyper local problems. I was hoping to start a consulting company to help early stage startups with mentorship, software architecture help, and any other services they would need to get their ideas launched. I traveled out there in January 2016, but ultimately decided that it was not the right time to pursue. At some point in my career, I want to share my expertise to help product creators solve community needs.

What would someone be surprised to know about you?

I LOVE to dance! My close friends know this, but most people don’t. When I was a lead at Beatport, I decided to take DJ lessons to better understand our user base. I learned then, that I loved DJing and dancing. I now DJ around New York City and go dancing several times a week. The dance floor is one of the few places where I can be truly present.

What key piece of advice would you give to someone who wants to create their first app?

If your gut tells you that you have a good idea, listen to it and start building. You’re never going to have all the answers to determine if it is the right idea or exactly the right time. There were so many things we learned along the way that if we had known up front may have prevented us from ever starting SkyHi. We hit so many walls, but we were resilient and found ways through them. For me, it’s been the growth along the way that has been the most rewarding.

Anything else you would like to share with our readers?

You’re obviously interested in travel since you’re part of the TWIP community. I’d say, for me, the experiences I’ve had on the countless travels in my life have fundamentally shaped me to be a better human being. I have learned so much from other cultures and people. I’ve seen things that are awe inspiring. I’ve been on spontaneous adventures that have become some of my favorite moments in life. Travel has made me more compassionate, more patient, more adventurous, more understanding, more confident and happier. When I think back on my life so far, it’s all those experiences that fill me with joy. So, keep getting your passport stamped and exploring. You’ll be better for it.

More facts about Rama:
De-Stress Technique: Dancing, running and meditation
Latest Gadget: Native Instruments Traktor F1
Favorite App: Instagram forever
Favorite Travel Brand: Airbnb
Next Vacation Destination: Thailand