Leader of the Week – Around the Ivies

For this week’s Leader of the Week – Around the Ivies, we spoke with Rob Karp ’19, student at Cornell. Rob is the founder and CEO of Miles Ahead, a high-end travel advisory firm. *Interview minorly edited for length and clarity.

Please tell us about Miles Ahead and what it does.

Miles Ahead was founded four years ago when I was a sophomore in high school. We are a high-end travel advisory firm; we help our clients optimize miles and credit card and hotel points and turn them into free airfare. We design experiences around the world and give our clients the high-end treatment. We’ll do anything from planning a 17-day African safari to a honeymoon to getting someone from New York to L.A. tomorrow night using only points.

We actually do a lot of consulting for different small businesses, companies, and individuals on setting up optimal credit cards. We’re a team of 10 — a lot are at Cornell, in the hotel school, some at the architecture school. We have people at Boston University at the hospitality school there. We have some at Vanderbilt. We have some on gap years going to Babson and Harvard next semester or next year.

How did your interest in travel begin?

My aunt and my cousin live in Minneapolis, Minnesota. Starting when I was 6 months old, we flew back and forth between Westchester’s airport on Northwest on an RJ185. We’d fly once or twice a year back and forth. And I loved flying. I loved getting on a plane and taking off. I get chills down my back. So, when I was 7 or 8 years old my parents got me Microsoft Flight Simulator. During middle school, I would wake up in the morning. Go on. Take off. File a flight plan to go to London or L.A. or wherever it might be. And I would come home from school and land the plane. When I was 9 years old, I started flying for Delta virtual airlines. So that’s where my passion began. Today if there’s a plane in the sky, I can tell you what airline it is and their exact model.

I have always been so excited about getting on the planes, but I started to think about what it takes to get on a plane. Are my parents paying for this? Are they using miles? What are all these different magazines? I started helping my parents book these flights to Minneapolis. That turned into my becoming my dad’s corporate booking assistant for all his work travel when I was 11 or 12 years old. By the time 13 or 14 rolled around, my dad was basically freelancing me out to his friends and colleagues. There was a network of people I was doing this for and they kept coming back to me saying, “You should do this professionally — you’re really good at it.” And I would always respond “No, no, I’m 14.” But they kept encouraging me. So I started a business on November 26, 2012. It was originally called Karp Enterprises LLC with an LLC with New York state. That business took off. We re-branded a few years after as Miles Ahead. Our slogan is “Travel on Point” as in we’re going to nail your travel for you but also you can travel with points… It’s a play on words. That’s where the passion started. In high school, I was also part of a science research program. With my program, I did research on airline mergers, specifically on the Delta/Northwest merger in 2007. I also worked for two summers in Delta’s risk management department. I spent time at their headquarters interning. I got to meet the president of Delta and other really interesting people and that added to my exposure and interest.

How do you balance doing this and being in school?

I’m a sophomore now; when I came as a freshman last year, the first semester was pretty easy. It was not very overwhelming. I kind of shut down for a few weeks as I was transitioning in, but I felt like I was missing a part of myself. I don’t really see it as work; it’s a passion. So then I started working for Miles Ahead again. Great first semester. Second semester came around, and things became more difficult. Second semester was a challenge of how to balance and how to keep everything going. I worked this summer on putting together the organizational structure to create a way for me to balance my social life, my professional life, and my academic life and be able to prioritize whichever in that moment is most important. And this semester in the fall has been phenomenal. I am doing so much better in school. I am so much happier. We had our best month ever in September. We’ve had lots of different challenges and obstacles but we’re doing our best to tackle it. One of those things has been saying, “Hey, you have 24 hours in the day. You have to sleep. You’re still a college student.” I have to realize school is important. Thursday night rolls around, Friday night rolls around, Saturday night rolls around, and I’m putting my phone down and not talking about the business. I also manage a very meticulous calendar… I have three Google calendars. My motto is: if there’s something you love, you’re going to find time for it. If it’s important enough to you, you will find the time.

Who inspires you?

My dad professionally inspires me every single day. He always works long hours and works very hard. As a dad, he’s been phenomenal. We still talk every day about strategy. We’ll go back and forth from talking about something causal to, “Hey, did you do this with your workers compensation model?” My mom has been so supportive. She doesn’t necessarily have the business mind, but she’s helped me become a much better listener and learner and people person and understanding things. Because of my mom, my emotional intelligence is so much greater than what it was. My uncle has always been there. Really amazing. Sometimes you don’t want to talk to your parents about certain things and he’s always been there.

And my parents have always supported me with everything I want to do. I started this business day one with $0. I worked as a soccer referee my sophomore year of high school and made $600 doing that. I’ve taken that $600 and now the company is generating over a hundred thousand dollars in revenue. That has been a journey. This is mine that I took and grew from the ground up. I took that $600 and built a website and hoped that people would come. And they came. This is a service business where if you make someone happy they’re going to talk to their friends. You don’t know if this is going to be tomorrow or in a year or could be a month but you just sort of have to have that mindset.

Where do you see yourself and this company in 10 years?

I never want to give it up. I love what I do every day, and I work 50 hours a week. I’m a full time student at Cornell; I have so much other stuff going on. And I love it. Keeping busy and keeping me excited every day. Are we going to be a new type of travel agency in ten years? I don’t know. Maybe we’re going to be something else. We just got into eLab which is the top incubator at Cornell. They’re working with us to take our company to the next level. Every other company there is made of graduate students with a business plan and a concept. We’re the only company that already exists, that has revenue and is profitable. We’ve gone to them and said, “Look. Here’s what we have, here are challenges, here are all the ideas we have. How can you help us moving forward? How can we learn? How can we learn how to be better?”

So in ten years, I still see myself at Miles Ahead, but I’m really excited to see what Miles Ahead will be in ten years. It’s really a dream that every single day I get to do what I’m doing and do it with other people who also love it. I’m just excited for what the future holds.

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