Rob Karp, MilesAhead

Rob Karp, CEO and Founder of MilesAhead

Rob Karp

Founder and CEO


IG: @milesaheadco

Personal IG: @robkarp_

I’m sure you’ve received this question more times than you can count, but take me back to when you were fourteen; what planted the seed for you to start your own business?

It’s kinda funny, I never expected to start a business. Growing up, I loved airplanes; flying on, watching and even (virtually) flying them. As my passion for aviation developed, I became fascinated with purchasing flights and the world of miles and points.

I started helping our family get to Minneapolis and my dad with his work travel – I was a math kid and it was like one big game for me. Soon enough, I was helping family and friends out of pure enjoyment. After school fun was calling the airlines!

I explained what I was doing to my cousin’s grandparents at a family event and they (along with my parents) encouraged me to start a business. Three weeks later, Karp Enterprises (later to be MilesAhead) was born.

MilesAhead did about $12 million in sales before you even graduated from Cornell. How did you balance coursework with running a business?

It’s not something they teach you in school! I learned to make the most of each day (or at least, I tried!). Calls between class, emails at all hours of the day and staying focused on the task at hand.

I quickly realized I couldn’t do this alone and I needed a team by my side. Fortunately, I met (and hired) many peers along the way who allowed me to delegate and shape MilesAhead into what it is today. 

There’s a lot of competition in the travel industry, how have you positioned MilesAhead to be so successful in the luxury market?

MilesAhead was born helping travelers optimize their frequent flyer miles for (nearly) free flights. We helped you get from point A to point B using the least amount of dollars or miles. As we evolved over time, our focus shifted to providing an “elevated luxury” experience, putting knowledge, expertise and service at the forefront.

We’ve traveled to dozens of countries, seen hundreds of hotels and spent thousands of hours networking with hospitality leaders across the globe. That being said, we continue to stay true to our roots and highlight our airline and miles/points knowledge as a key point of difference. And it’s a thrill to put it to use for our clients.

What are some of the setbacks that you’ve faced? How did you overcome them?

The mother of all setbacks has been COVID-19; running a travel business through the pandemic has been a challenging and humbling experience. We started off 2020 with our two best months yet, to be followed by some of the lowest demand periods, personnel changes and an ever-evolving landscape of travel restrictions.

During this time of uncertainty and limited travel, we have stayed close to our clients, brainstormed ways to stay relevant, and considered what MilesAhead is going to look like coming out of the pandemic.

On another note, I remember our first booking at one of my favorite luxury brands, when the clients showed up and things were not as advertised. I felt it was a good idea to call the Global Head of Rooms to voice my concerns. While happy to help, I learned that sometimes you don’t need the big boss to solve every problem 🙂

Do you have a favorite destination?

Florence, Italy!

In July you shared an Instagram post with the caption; “Last Friday, I returned from 46 days of responsible travel during the pandemic. I stayed in 14 hotels, took 10 flights and visited 7 states.” How do you define responsible travel?

I was fortunate and excited to travel early on during COVID-19, when many were not comfortable leaving their homes. In a sense, I felt it was my responsibility to get on the road and see what the experience was like, how things were different, and to tell the story.

That being said, it was very important to me to be respectful of my surroundings and the communities I was visiting, whether that meant wearing a mask, social distancing or getting tested. In a time full of controversy and unknowns, responsible travel meant being extra self-aware and thoughtful, putting others before you.

Rob Karp of MilesAhead

Were there experiential differences that you encountered throughout your stays, prompted by the pandemic, that might surprise people?

On the whole, I was pleased with my hotel experiences and wouldn’t say there were too many surprises.

All the hotels reached out ahead of check-in to proactively share their new policies and any limitations. Most indoor facilities, touch points (e.g. dining menus) and interaction with staff was limited.

A big difference is the added aspect of pre-planning; if you want to work out or eat on a whim, that isn’t possible anymore. Reservations – from tennis, to the spa, to the gym – have become a must. 

What does the travel industry look like today? How do envision the future of travel?

The travel industry is going through perhaps its most challenging times in the past century. Remarkably so, I find the industry and my colleagues in particular to be full of resiliency. There is a positive outlook toward 2021, optimism post-vaccine and lots of creativity flowing. I’m confident travel will be more thoughtful and intentional moving forward. It will be with more of a purpose than ever before; whether it be why, where or who you are going with.

What advice would you offer to young entrepreneurs that look to you as a role model?

The best thing you can do is get started, keep an open mind and enjoy the ride. Starting a business sounds sexy, but is fundamentally challenging and requires serious commitment. You’re identifying a problem, creating a solution and convincing others to use your product or service.

Write down all your thoughts and ideas. Don’t be afraid to try new ideas and be honest with yourself. Most great ideas fail before they see the light of day.

If you were to leave us with something to think about, what would it be?

More than ever this year, I’ve seen people re-evaluate what’s important to them and what they really want in life. Asking questions they never would before, taking pivots in new directions and prioritizing themselves.

While this is a crisis, it’s also an exciting time, one when great new ventures, ideas and discoveries are born. And it’s brought a smile to my face. I know you talk about this too, Kaitlin. Life is too short, find what makes you happy, see if you can integrate it professionally and share it with those who you care about. 

Visit MilesAhead to learn more.

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