Investing in Service: Interview with Regal Wings Founder Eli Ostreicher

by / ⠀Entrepreneur Interviews Entrepreneurship / July 15, 2014

Eli Regal WingsEvery business requires investments, but not all investments are monetary. When Eli Ostreicher started New York City based boutique travel agency Regal Wings, startup capital was not the most important investment made in the company. “It wasn’t so much about investing financially, but investing effort and everything that I could give to it.” Regal Wings acts as both a travel consolidator and business travel management provider.

The company was founded in 2006 and started as a single booking made by Eli in the bedroom of a small apartment in Miami. His first customer was his uncle. Word quickly spread among his uncle’s friends and Regal Wings took-off. Eli admits that he started Regal Wings with basically nothing. “I knew no business tools. I didn’t know what payroll meant.” Eli didn’t know much about how to run a business, but he did know how to work hard and how to provide exceptional service to others.

Regal Wings Logo

The effort invested in the company and service has not gone unrecognized by customers. Regal Wings has focused on customer service from the start and it remains their strongest competitive advantage. In my interview with the young entrepreneur (audio below), he told the story of a regular client who flew often from New York to Hong Kong. On one occasion he needed a last minute ticket for the trip. He needed a kosher meal, but due to the last minute booking of the ticket, they couldn’t confirm that a kosher meal would be available on the flight. Eli woke up at 4 am, made several kosher sandwiches and met the customer at the check-in desk before his flight. Their efforts and success in customer service are a clear product of Eli’s passion, hard work, and determination.

Life as an Entrepreneur

Eli on being an entrepreneur: “It’s a choice that a person makes. You can either have a typical life (9-5), or you can do it on a different type of scale. It comes at a price, but it’s rewarding.”

Asked when he first recognized that he had an entrepreneurial spirit, Eli replied, “As a kid, I was called different titles. I was given the name of ADD and ADHD. I was a hyper kid and I always came up with these interesting ideas.” Later in life, Eli conducted his own research and realized that although he had some traits of being a dreamer and hyperactive, there was one big difference between himself and the traditional traits of someone who has ADHD – the ability to complete tasks. Eli lives and breathes with to-do lists and has trouble sleeping if he still has incomplete tasks.

As an adult Eli is just as active as in childhood, but he remains focused and goal oriented. On any given night you may find Regal Wings founder Eli Ostreicher at one of his several offices, on one of his two cell phones, looking at one of his three computer screens.

Harei At Staff Meet-

Working hard and keeping his mind on the business has worked out well for Eli and Regal Wings. Regal Wings was listed on the 2013 Inc. 500 list and was the fastest growing travel company in the US, which Eli said was a “big honor.” After being notified this past week that Regal Wings has once again made the Inc. 500 list, Eli said, “we are exstatic!” 

Perfecting the Niche

Eli’s successful ventures all capitalize on a niche market. In addition to Regal Wings, which focuses on first class and business class travelers, Eli started Harei At, an Orthodox Jewish dating service with tens of thousands of active members. Eli stated that within the community it is a necessity to get married. He built Harei At as an alternative to going to a matchmaker.

Harei At Logo

Eli was told by a smart friend that “every business man knows each company needs a USP – Unique Selling Point. If you want to take it to the next level, work in a niche market.” It’s not always possible to target a niche, but it has worked very well for Eli. He couldn’t share the details, but he did hint at an upcoming launch that will have a much broader focus.


It’s refreshing to see a young entrepreneur focus on service beyond the popular trend in building tech businesses. Regal Wings’ investment in customer service is paying dividends, and helps to set them apart from larger, less-personal touch based companies and services.

Listen to the full interview with Eli Ostreicher below!

Interview Highlights

  • Why Monday is his favorite day of the week.

  • On something he previously struggled with: letting go of an employee. “When someone doesn’t do their job the right way, do not let the damage continue.”

  • Eli’s best piece of advice for young entrepreneurs: “If you try hard enough, you will succeed.”

  • A discussion about niche businesses and targeting a specific market instead of ‘everyone.’

Quick-Fire Questions

How many hours a week do you work on Regal Wings and other business ventures? “Basically, I work non-stop.”

How much sleep do you get a night? “It depends. I love to sleep. I make up for it when I do sleep in.”

What was your worst business idea? A solution to fix cracks in car tire rims caused by potholes. The more research he did, the more he realized the idea wasn’t feasible.

If you could not be an entrepreneur – if you were banned as an entrepreneur, what would you be? “Ouch, that sounds like a punishment. Thank god that’s not the case. It would probably be something in IT. I’d probably be a really geeky Cisco network administrator somewhere.”

If you could add one entrepreneur in the world to Regal Wings, who would it be and why? “A very wild answer would be Warren Buffet. On a more realistic level I would say Barry Liben, CEO of New York City based travel agency called Tzell. I find him as the most brilliant entrepreneur as well as a friendly nice man.” 

Listen to the full interview here:


*Eli Ostreicher is a member of the Young Entrepreneurs’ Council (YEC). Special thanks to the YEC for the interview. 

About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.