Subscribe to Entrepreneur for $5

How to Scale From a Small Business to a Billion-Dollar Empire

Radio mogul John Dickey talks about how he built one radio station into a $2 billion media company.

Opinions expressed by Entrepreneur contributors are their own.

You may not know John Dickey by name, but you may have heard of the company he and his brother started in the '90s: Cumulus Media. The duo bought a radio station in Atlanta then continued acquiring stations until their business, which has an estimated net worth of $2 billion, became the nation's second largest radio company.

The brothers' journey began after college, when they founded a media buying consulting company. Dickey has seen the media industry turn upside down, and continues to stay on the cutting edge with digital video. He was recently named the new CEO of Ora TV, a digital broadcast network co-founded by billionaire Carlos Slim and broadcasting legend Larry King.

Related: 10 Ways to Build Trust and Credibility With Your Customers

I sat down with Dickey to learn how he navigated the ups and downs of a changing landscape and ended up on top.

1. Find and fill a need.

It's worth noting that the Dickey brothers majored in English and history -- not business, entrepreneurship or broadcasting. They did have a knack for business and statistics, and after college they decided they wanted to start consulting businesses, so they searched for a need and discovered that most small businesses didn't have access to market research data and were making misguided media buys. They formed Stratford Research going door to door to small businesses with a great hook that spoke to the pain point of the potential customer.

"When you said, 'Would you like to know which half of your marketing dollars are wasted?' They found a way to give you 10 minutes." Dickey says.

2. Look at both sides.

The Dickeys achieved massive success later in part because as consultants, the brothers realized they could serve not just media buyers but also media properties selling ad space. Their knowledge of how to invest marketing dollars into television, radio, print ads and direct mail put them in a unique position to advise media companies on programming decisions. This addition led to continued growth of Stratford research for 15 years. Dickey realizes they entered the industry at an opportune time, but timing is only part of the equation.

"We got lucky and we were pretty good," he says.

3. Don't give in to marketing FOMO.

Dickey says it's common for busy owners to just buy into what's hot or trendy, or even simply what's being pitched to them by a "marketing expert." Don't let the fear of missing out rule your marketing dollars. Trust your instincts, Dickey advises. When you see a marketing opportunity, ask tons of questions and make a strategy and avoid jumping on every new platform.

"To use a military metaphor, there's nothing wrong with standing still if you don't know," he says. "Where you blow a leg off in a minefield is if you keep walking when you don't know what you're doing."

4. Start small and replicate what works.

After advising for almost two decades, the brothers decided they wanted to get in the game themselves. They decided to buy a radio station in Atlanta, then two, then a few stations in Nashville.

"We basically just applied what we were doing for other people to stations we'd placed our own bet on," he says. "Lo and behold, it worked."

Related: A 3-Step Startup Guide to Connecting With Consumers

They continued buying stations in different markets, until the Communications Act of 1934 was altered in 1996, allowing them to expand rapidly. The brothers knew their competitor Clear Channel, now iHeartMedia, were focusing on large markets, so they decided to buy stations in small and mid-range markets.

5. Know your media business model.

Dickey pointed out that a strong media strategy is key, and that strategy will be different for a media company vs. a media personality. If you're trying to grow your personality brand, a la the Kardashians, Dickey recommends you view each platform as a tool for that goal, not as goals within themselves.

"Get around as many people as you can that have experience in building multi-platform brands or even people that have experience in one type of platform, and pick their brain non-stop until they're tired of talking to you," he says.

He also advises to focus on engagement, creating unique, compelling content and building a believable brand, even it's a persona. Trying to build a podcast or YouTube network of channels? Dickey says you're in for a rough road because there is so much more supply than demand, a problem that will only get worse with the low cost of entry into today's media platforms.

6. Look at the whole picture.

A new media platform seems to pop up every day, but change does not mean Snapchat vs. YouTube vs. broadcast television. Instead, Dickey says, media entrepreneurs today must ask, "How can they all work together?" He also pointed out that brands no longer progress from legacy media, radio and television to mobile apps and podcasts. The sequence can now be vice versa or simultaneous and, once you start achieving success in one area, the bridge between platforms shortens.

"You have to be willing to think about the media landscape in a way that's never been thought of before," he says. "The giant media companies of tomorrow are going to look very different from anything we have thought of thus far."

One key point for the future is mobile, he explains. If you have a mobile strategy, you're behind, because they world has moved to a mobile culture.

7. Always focus on quality.

Again noting the low cost of entry, Dickey explains that producing large quantities of sub-par content is not going to cut it. On the other hand, amazing content at exorbitant production prices won't work for much longer either. Dickey is excited about the possibilities for Ora TV because it marries the quality and integrity of the Larry King brand with a mobile-first and digital-first strategy.

"That level of quality is always going to be in demand," he says.

The demands and changes of the industry can be overwhelming, but Dickey reminds media entrepreneurs to stick with the basics.

"Creativity, hard work, understanding an audience, being able to go out and bring a technology perspective into your craft and not being afraid of it, embrace it."

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

Related: The World-Changing Power of Sharing Your Story

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 as well as our apps on Amazon Fire, Roku and Apple TV.

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


How a Throwaway Joke Became an Award-Winning Ad Campaign

In our 'Creative Conversations in Advertising' series, Creative Director at Goodby Silverstein & Partners Tristan Graham and Entrepreneur magazine Editor in Chief Jason Feifer discuss the birth of a very funny (and impactful) commercial.

How This Amazing Campaign Succeeded in Changing a Brand's Perception and People's Lives at the Same Time

In our series 'Anatomy of an Ad,' Group Creative Director Tony Jones gives the heartwarming story of how Operation Santa finally took off.

How this Tech Entrepreneur, Biohacker, and Author is Helping Women with Their Periods

The founder and CEO of Flo Living on the future of biohacking and hormonal healthcare.

Duce Raymond of Sweet Baby Ray's BBQ on Using Social Media Like a Boss

Interview with Sweet Baby Ray's BBQ Catering Culinary Director Duce Raymond about his fresh approach to social media content marketing and huge results with short video for the already world-famous brand.

The Key to Effectively Communicating Important Messages Is All About Simplicity

In our 'Creative Conversations in Advertising' series, award-winning Group Creative Director Giancarlo Rodas and Entrepreneur magazine Editor in Chief Jason Feifer discuss distilling complex ideas down to a simple message.

How to Deliver a Serious Message Through Humor

In our series 'Anatomy of an Ad,' Creative Director David Stevanov explains how humor can be a storyteller's most effective tool.

This Successful Shark Tank Entrepreneur Shares His Latest Innovation

The Founder of Ooonimals, Club 44, and the OOO Studio Lab talks about his current projects and what you need to know about the risks and rewards that exist in the NFT space.

Brendan Sweeney of Popmenu on How Ego is the Root of All Evil

Interview with Popmenu CEO Brendan Sweeney about building a positive user experience, the state of restaurant technology, and the importance of providing answers.

Recession-Proof Your Mindset with Neuroscience

With top economists fearing a recession, award-winning author Ben Angel teaches how to recession-proof your mindset with neuroscience to manage stress levels.

How to Find Your "Oxygen Points" to Sustain and Grow Your Business, According to an Investment CEO

Entrepreneur Network Partner Ashley Crouch sits down with the CEO of Al Zarooni Emirates Investments, Dr. Adil Alzarooni.

How to Get Investment Funding for Your Business

Entrepreneur magazine's Editor-in-Chief Jason Feifer and Narya Partner Falon Donohue have a lively and informative conversation about securing the funding you need to launch your dream.

Keith Koo Explains How Angel Investors Prioritize Startup Funding Decisions

Entrepreneur Network Partner Ashley Crouch sits down with the Managing Partner of Guardian Insight Group and Angel Investor, Keith Koo.

Why this Popular Web3 Esports Game Was Designed with a Play-to-Earn Model

The Chief Product Officer of MonkeyLeague discusses his company, why monkeys are all the rage for NFTs and gaming, and his advice for developers.

Want to Get Customers' Attention? Tell Them a Great Story.

In our 'Creative Conversations in Advertising' series, award-winning creative director Josh DiMarcantonio and Entrepreneur magazine Editor in Chief discuss the power of storytelling.

Discover Entrepreneur Series

Whether you need advice on how to get your business off the ground or you’re just looking for inspiration, our video series have something for everyone. Browse our library below to find a series that speaks to you and your interests.