Jared Simon: Today’s Notable Young Entrepreneur

Today’s Notable Young Entrepreneur is HotelTonight Co-founder and COO Jared Simon, whose five-year plan sees himself running the most dominant hotel booking service in the world. Here’s what inspired him towards his career route…

Elevator Pitch: Describe your job in a nutshell.
My job is to make sure our organization is set up to ensure we only hire the best people and that we’ve set things up to allow them to excel – no barriers or obstacles to them doing the best they can do. I make sure they’re empowered to be the best.


Why did you start working at your company? What was the inspiration for this career route?
I started working at HotelTonight because I’m one of the founders. My inspiration came from always being interested in creating new things that solve problems that I’ve had as a consumer. HotelTonight represented a solution to a common problem I’ve had – I like to travel spontaneously and HotelTonight allows that to happen (efficiently, effectively, in style).


What is the best part of what you do on a day-to-day basis? The most challenging part?
Best: working with a talented team, getting challenged by the talented team; seeing hoteliers’ eyes light up when we show them the great solution. Challenging: Getting the word out. We have a great product but there are a lot of companies that have more money to spend. We have to make sure the good ideas don’t get drowned out


What is one sign that you’ve seen over the years to suggest that your work/life balance is off?
Prior to starting HotelTonight, I spent 15-20 days snowboarding in Tahoe. Since starting HotelTonight, I haven’t gone at all.


Where do you see yourself in five years?
I see myself running the most dominant hotel booking service in the world.


What is one major challenge that you’ve had to overcome in your career? How did you overcome it?
By nature, I’m pretty skeptical. I’ve had to overcome that to become an entrepreneur. When you’re an entrepreneur you have to consistently be positive about what you’re doing and truly believe that you’re going to succeed.


What does success look like to you? Does Money = Happiness?
Money does not equal happiness. Success for me is building a company that is big and important and moves the industry and the world, and I want it to be a new approach that never existed before. We don’t want to be a company that gets big by exploiting a wrinkle in the universe.


What is the most memorable milestone in your career?
When someone wanted to hire me and believed that I could do something productive. Getting my first job out of college (investment banking) was unbelievable to me.

Do you have any advice for other young professionals?
I hear people constantly talking about how they have to have a plan and a vision for how their career is going to unfold, but I think that’s not the way it needs to be. I’ve never been able to predict my career – it’s all unfolded based on what I wanted to do and try at the time.  If I’d had a plan and followed it, I definitely wouldn’t be where I am today.

Where is your favourite place to wine/ dine in your city and why?
Fish in Sausalito, California. It’s outdoor on the water, casual, and very low-key. It’s not high end, it’s just authentic and really good, simple seafood.

When you’re not working how do you love to spend your “Me” time?
I love going to concerts – Broken Social Scene, Jack White, Stars.


Where is your favourite place to travel? Why?
Central America is beautiful. I love the food and the people are salt of the earth. I absolutely love meeting new people.

If you had to choose a theme song, what would it be?
Dazed and Confused by Led Zeppelin. In a start-up environment, I am constantly dazed and confused.  

If you weren’t doing what you’re doing, what would you be doing?
I’d be a rockstar.

Do you support any charities? If so, which one(s) and why is that important to you?
I’m a big proponent of my undergraduate school – at university I was in a program that was as little arts college within the university. It’s called PlanII.


What to you is notable?

BlackBerry, iPhone, Android, or Other?
iPhone for great apps, Android for great device features, and BlackBerry for messaging.


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