📺 Stream EntrepreneurTV for Free 📺

4 Tips for Success From a Multi-Millionaire Serial Entrepreneur Entrepreneur Network partner Kelsey Humphreys talks to serial entrepreneur Kenny Ditcher about his track record building and selling one successful business after another.

By Kelsey Humphreys Edited by Dan Bova

entrepreneur daily

Opinions expressed by Entrepreneur contributors are their own.

The story of the hustling D-student who built a business from a dorm room never gets old, which is why I loved interviewing Kenny Dichter. That's exactly how the serial entrepreneur, now the CEO and founder of Wheels Up, got his start. But what sets Dichter apart is his track record since then: building and selling one successful business after another.

In college, Dichter and a friend began creating and selling T-shirts with "Wisconsin flair" at the University of Wisconsin-Madison. The apparel line started to gain traction, so Dichter moved the operation from his dorm to a nearby storefront. That business grew to three locations before Dichter sold it upon graduation.

After his first success, the father of one of his friends, a clothing manufacturer, decided to back Dichter's next apparel venture. His operation moved from Wisconsin to New York City, and he was soon fulfilling orders for the likes of Wal-Mart and Sears. As the company reached a tipping point, Dichter decided to sell it and start a new venture, a process he would repeat over and over again.

His next business took him into the world of sports marketing. His friend Jesse Itzler, a jingle writer, saw an opportunity to build a business around the music that played in arenas during sporting events. Dichter provided the strategy for Itzler's idea, and the two sold that business to SFX Entertainment for more than $4 million in 1998.

By that point, Dichter had experienced substantial success firsthand, and he noticed that no one in his social circles flew commercial anymore. On one of his first private flights, the idea for Marquis Jet was born. Marquis Jet was the first aviation option that allowed members to reduce travel costs by buying blocks of hours on a pre-paid card instead of purchasing their own aircraft. Again, Dichter grew his idea and made an exit, selling Marquis Jet to Warren Buffet's NetJets in 2010. Before returning to aviation with Wheels Up in 2014, Dichter built and sold another business, Tequila Avion, an ultra-premium brand that sold for $100 million.

His latest success offers the private aviation industry a membership model without spending requirements or hourly minimums. Wheels Up raised $115 million in funding in February 2016, and according to Ditcher, it now holds a valuation of $521.5 million with a projected worth of $1 to $1.5 billion by 2020.

Clearly, Dichter knows what he's doing. Here are his top four pieces of advice for entrepreneurial success.

1. Embrace rejection.

Dichter explains that as an entrepreneur, belief in one's self is paramount. One must be able to pivot -- and realize that hearing "no" is a good thing. Why? Because it means you are innovating.

"If everyone saw what you see, they'd all be doing it themselves," Dichter says.

To embrace rejection does not mean to accept rejection, however. Dichter believes that "no" just means "not now."

"Never take no for an answer," he says. "You have to have the belief in yourself that you can sit at the big table."

2. Value relationships.

Dichter often says "my friend" or "my buddy" when referring to his partners. He also emphasizes that if you want your employees to treat customers like rockstars, you need to treat your employees like rockstars. Dichter clearly values relationships, and he cautions entrepreneurs never to burn a bridge. "As an entrepreneur you touch a lot of lives," Dichter says. "Just be fair, have integrity, do what you say you're going to do."

He encourages entrepreneurs to cherish existing customer relationships. Try to take someone who is "interested" and convert them into a "believer." His advice for everyone trying to build the next Birchbox or Dollar Shave Club is simple: "The only thing that matters in a subscription business is, can you keep [your customers]? Retention is the number-one value metric."

3. Create a clear map.

Dichter is a huge believer in business plans. When Itzler approached him about a music business, all he had was an idea. It was Dichter's job to make the plan turn into a business. This is a step many entrepreneurs don't execute well, Ditcher says.

"Ideas are fragile," he says. "Ideas are not enough. You need to have a concrete plan that can serve as a map."

4. Know your numbers.

An idea and a plan are also not enough, Ditcher says. You have to have the proof. Now that Wheels Up has 3,500 members, Ditcher can start to rest a little easier. Is there a certain number one needs to hit before a successful exit? Ditcher explains that the average life cycle of a great idea is five to seven years. If you want to maintain success, and you've taken outside investments, you need to prepare for your exit, Ditcher says. "If a restaurant is given five stars, sell the restaurant, because it doesn't get any better than that."

Ditcher, like many serial entrepreneurs, is in it for the climb, not the destination. And right now, he's on the way up.

Watch more videos from "The Pursuit" on the show's YouTube channel.

Related: 7 Refreshing Do's and Don'ts for Success

Entrepreneur Network is a premium video network providing entertainment, education and inspiration from successful entrepreneurs and thought leaders. We provide expertise and opportunities to accelerate brand growth and effectively monetize video and audio content distributed across all digital platforms for the business genre.

EN is partnered with hundreds of top YouTube channels in the business vertical and provides partners with distribution on Entrepreneur.com as well as our apps on Amazon Fire, Roku and Apple TV.

Click here to become a part of this growing video network.

Kelsey Humphreys

Producer, Host, Entrepreneur, Journalist, Author

Kelsey Humphreys is a media entrepreneur, journalist and author on a mission to break down "success for the rest of us." She is the author of the Amazon bestseller Go Solo. Catch interviews with today's leaders on her show, The Pursuit

 

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

More from Kelsey Humphreys

5 Tips on Being a Disruptor in the Fitness Industry

How to Turn Your Tipping Point Into Lasting, Next-Level Success

How to Successfully Transition From Passion to Passion in Business

This Viral Video Star Explains How to Survive Beyond Your 15 Minutes of Fame

Side Hustle

These Coworkers-Turned-Friends Started a Side Hustle on Amazon — Now It's a 'Full Hustle' Earning Over $20 Million a Year: 'Jump in With Both Feet'

Achal Patel and Russell Gong met at a large consulting firm and "bonded over a shared vision to create a mission-led company."

Productivity

Want to Be More Productive? Here's How Google Executives Structure Their Schedules

These five tactics from inside Google will help you focus and protect your time.

Side Hustle

How to Turn Your Hobby Into a Successful Business

A hobby, interest or charity project can turn into a money-making business if you know the right steps to take.

Business News

These Are the 10 Most Profitable Cities for Airbnb Hosts, According to a New Report

Here's where Airbnb property owners and hosts are making the most money.

Business Ideas

63 Small Business Ideas to Start in 2024

We put together a list of the best, most profitable small business ideas for entrepreneurs to pursue in 2024.