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[Startup People] Eli Ostreicher – Founder Of The World’s Only Dating Site For Orthodox Jews

YEC Member Spotlight: Eli Ostreicher, CEO Of Regal Wings

Eli Ostreicher founded and runs several online companies within the luxury travel industry, employs over 100 people across several office in NYC & in Chennai, India. His company Regal Wings was #1 in Travel & Hospitality on the Inc. 500 list. Eli also founded the world’s only dating site for orthodox Jewish marriage-minded singles, which now boasts over 50,000 members.





Who is your hero?

Barry Liben, CEO of Tzell Travel.


What’s the single best piece of business advice that helped shape who you are as an entrepreneur today, and why?

Although a very old proverb with no official author, “Where there’s a will, there’s a way” has been and is my daily motto in business. When I went into business, people were saying that selling travel is a ‘gone industry’ because of the competing online giants. But will power, determination and ambition is proving them all wrong.


We found a powerful niche in the industry and focus on luxury travel. Being adamant brought us to where we are today. We have high-profile clients including Berkshire Hathaway, the United Nations, Bayer and the Maroon 5 band.


What’s the biggest mistake you ever made in your business, and what did you learn from it that others can learn from too?

There is a very fine line between being a good boss and too good of a boss.


In the first years of being in business, I was stuck with employees that were on payroll as charity – literally. They were the opposite of an asset to the company. They came every day because I was unable to let them go. I couldn’t face telling them they were fired. That was a hard lesson to learn. Nowadays, no new employee joins W-2 payroll or even gets an office keycard before a 60-90 day preliminary trial period.


What do you do during the first hour of your business day and why?

I live by to-do lists and my calendar. Having a clear understanding of the tasks ahead of me for the day is integral.


What’s your best financial or cash-flow related tip for entrepreneurs just getting started?

Honestly, I am terrible at financials and I find that most young entrepreneurs are too. Being good at money management and being a business visionary usually don’t go hand-in-hand.


My CFO signs the checks and makes budget decisions. You should find a person you trust to run the monies. He will tell you why a Superbowl commercial is a far-fetched dream.


Quick: What’s ONE thing you recommend ALL aspiring or current entrepreneurs do right now to take their biz to the next level?

Never give up! Unless you are trying to become the next Messiah, nothing is too farfetched or beyond reach.


Be focused, buckle up tight and you WILL get there.


What’s your definition of success? How will you know when you’ve finally “succeeded” in your business?

I once sat on a flight from India to New York next to an elderly respected businessman. He told me something I will never forget:


“Eli, before a company is systemized it is not a company. If you can’t be out of the office for three weeks straight without worrying that things might be going haywire, you don’t have a company.”


Thus my underlying goal in the companies I build is to systemize them to perfection. Think: conveyor belt!


Photo Credits

The YEC | Regal Wings

Author : Young Entrepreneur Council

The Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world's most promising young entrepreneurs. In partnership with Citi, YEC recently launched StartupCollective, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses.

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