4 Life-Changing Lessons Learned Chatting on a Flight to Florida

A young entrepreneur struck up a conversation with an interested stranger, not knowing he had the attention of Subway co-founder Frank DeLuca.

learn more about Jason Weingarten

By Jason Weingarten

Getty Images

Opinions expressed by Entrepreneur contributors are their own.

In spring 2000, I was a recent college grad working as a project manager and analyst at Capital One. As a young professional still transitioning into life post-college, I planned a spring break trip to unwind with friends. My trip didn't start out as smoothly as I had planned, with my flight from DC to Fort Lauderdale facing severe delays. While the delays seemed like a hassle at the time, what happened next helped pave the way for my success as an entrepreneur today.

At the time, airlines were much more lenient. I schmoozed my way onto a different flight and helped another gentleman switch flights. We ended up sitting next to each other, and at the beginning of the flight he opened up a business plan, which we discussed.

I told him about my own business plan for an idea to help college students find jobs online (the concept that ultimately led to my current business, Yello). He expressed genuine interest. I told him my passion was to build something that didn't exist, and I couldn't make a real impact until I set out on my own. It wasn't until the end of our flight, when my seatmate and I exchanged contact information that I found out he was Fred DeLuca, Subway co-founder and incredibly successful entrepreneur.

I got off the plane and immediately called my co-founder, Dan Bartfield, and asked him to look up Fred DeLuca.

Dan said, "Wow! Entrepreneur Hall of Fame, Forbes List, Subway."

Next thing you know, Dan was on a flight to Florida so we could meet with Fred at his house. Once we showed up, we discussed our opportunity, sales model, addressable market and the financing our business needed to get off the ground.

From that day until Fred passed away in September 2015, he served as a mentor and helped Dan and I get our business off the ground. We also had some fun adventures along the way, including watching fireworks on his yacht in New York and attending a Super Bowl party at Fred's house - none of which I ever imagined would happen as the result of setting out on a post-grad spring break trip.

Here are several business lessons I learned from Fred in 15 years of mentorship.

1. Set your business goals higher than what you believe is possible.

One of the first business books I read was Fred's "Start Small, Finish Big."

Many entrepreneurs underestimate the level of success they have the potential to achieve. They set conservative goals they know they can hit, which can hinder business in the long run, rather than setting aspirational targets.

With Yello, my initial goal was to get 100 companies on our hiring platform, but Fred pushed me to imagine what it would take to get 100,000 companies instead. He also attended one of Yello's user conferences and stood in a room full of customers repeatedly saying, "Think big. Think bigger!" It was thrilling to see him motivate the crowd. His excitement and positivity spread contagiously, and Fred encouraged our company and customers to always strive for aspirational goals.

Related: 7 Timeless Lessons About Getting Rich From a Book Your Grandparents Read

2. Shape the public's perception of your success.

Fred opened five or six Subway stores while the first location's sales were declining.

One reason for this is, if businesses appear successful - such as opening several locations -- potential customers will be more compelled to give the business a try.

The same goes for investors, the media and any other key stakeholders a business is trying to reach. As an entrepreneur, you have the power to shape your own success story. Taking a risk, such as opening several locations or advertising on a billboard can ultimately give your business the push it needs to become profitable.

Related: 7 Management Lessons From a 7-Time CEO

3. The smallest details can make the largest impact.

As a business owner, dedication to the details will set you apart.

Fred explained when Subway added cookies to the menu, the franchise experimented with the batter over and over again, not just prioritizing taste but also considering other things their customers care about when buying cookies, such as lactose intolerance and gluten allergies.

It might seem simple to just add cookies to the menu, but Fred said the details behind these types of decisions generated the most successful results.

At Yello, many of our solutions are the result of listening to our clients' challenges and working closely with them during the development period to provide the direct benefits they need - not what we perceive they might need.

We recently collaborated closely with a client to launch a product that met their specific requirements, which will soon be available universally.

Several rigorous months later, we were proud to launch a product that exceeded their particular specifications. Our client was so thrilled with the results that they not only flew our team to New York for a celebratory dinner, we all signed the wireframes, which are now prominently framed in both our offices.

Related: From Broke to Millionaire: 4 Lessons a Serial Entrepreneur Can Teach Us

4. Approach people, and strike up a real conversation.

From the moment we met on the plane, Fred taught me the importance of striking up a friendly, genuine conversation with anyone who crosses your path.

As a CEO, I enjoy engaging in conversations with every employee possible. I'm truly interested in their perceptions and opinions and try to meet with everyone individually.

I value the rapport that results from building one-on-one relationships. The same goes for meeting just about anyone outside the office.

Regardless of level or title, it's important to be approachable, have an interest in people and to not be afraid of having a candid conversation.

Through our initial conversation, Fred taught me never to place anyone on a pedestal or be intimidated to speak with people due to a perceived fear of seeing them as a celebrity.

As recently as a few months ago, I applied this lesson by walking up to Mark Cuban at an event and introducing myself. In many ways, these casual conversations can lead to some of your most valuable business and personal connections.

Sitting next to Fred DeLuca on a plane many years ago was a pivotal moment in my career. In addition to these lessons, he always stressed the importance of chasing my dreams as an entrepreneur. Every day, I strive to help others by paying Fred's lessons forward. I encourage all entrepreneurs to also learn from Fred's advice, and to think bigger.

Jason Weingarten

Co-founder and CEO of Yello

Jason Weingarten is the co-founder and CEO of Yello, which provides recruitment technology solutions for enterprise companies on a global scale -- from campus and event recruiting to talent relationship management. As one of Chicago’s fastest-growing tech companies, Yello helps organizations go from “hello” to “hire” on a single platform developed to meet, engage, capture and nurture the right job candidates.

Related Topics

Editor's Pick

Have More Responsibilities at Work, But No Pay Bump? Use This Script to Get the Raise You Deserve.
Black and Asian Founders Face Opposition at All Levels — Here's Why That Has to Change

The Greasy, Glamorous Rise of Mascara

You won't believe the grimy gunk people used to smear on their eyelashes -- and still do.

Business News

'Our Kids Aren't Even Safe To Order Food': Mother Outraged After DoorDash Employee Uses App to Flirt With Teen Daughter

One mom is going viral on TikTok after catching a DoorDash employee attempting to flirt with her 15-year-old daughter through the messaging service provided through the platform.

Business News

An NFL Rookie Scores a $514,000 Jackpot in Las Vegas

Los Angeles Rams running back Ronnie Rivers sat down to play 3-card poker and left a half million dollars richer.


This Is the Overlooked Tool Your Business Needs to Reach Your Target Audience

Voice search is growing, and your business can utilize this important functionality to get more customers. Here's how.

Business Ideas

How to Make Thousands of Dollars on the Side As a Virtual Assistant

Apply your skills and experience to create a lucrative virtual assistant side hustle or full-time business.