Five Creative Leadership Take-Aways from David Oakley

To gear up for an innovative and successful year, Endeavor’s first Collaborators & Cocktails event of 2022 featured David Oakley, president, co-founder and chief creative officer at the critically-acclaimed, Charlotte, NC-based advertising agency, BooneOakley.

A self-proclaimed trickster, hustler and white liar, Oakley easily held an attentive (and amused) audience as he shared a few key tenets of life that he’s gained from his more than 20-years leading BooneOakley and helping grow their clients’ businesses.

“It’s okay to make mistakes. Sometimes mistakes turn into something great.”

Just take a look at the first ad BooneOakley ever produced.

Anything seem off? CNN thought so, too. The “Bush-Gore” billboard made BooneOakley a laughingstock, even though they revealed later that the idea was intentional, getting their first client,, phenomenal coverage on Good Morning America, USA Today and The Wall Street Journal. “After that, nothing scared us anymore,” Oakley said.

“It’s all about relationships.”

Before Oakley started his agency, he met with the head of a “creative superpower” agency in Seattle who he admired. When Oakley told him that BooneOakley would be the best creative agency in the Southeast, the agency head told him he would fail.

Why? Because great creative is really only a 7 or an 8 on an agency’s top 10 list. What’s number one? Relationships.

“It’s all about trust, getting to know your clients and building a relationship,” Oakley said. “You are never going to do the work you want to do if people don’t believe in you and trust you. You get permission to be creative when you have the trust, and you are a partner with your client. That’s when the magic happens.”

“Do great work for people you like.” Or rather, “Do great work WITH people you like.”

From day one, BooneOakley’s mantra was, “Do great work for people you like.” More than 20 years later, the agency has only changed one word. That one word made all the difference.

“Do great work with people you like.”

“Today, it is all about collaboration. It’s a relationship. It’s about working together. It’s better when we work together” said Oakley.

“Don’t do things people remember. Do things people will never forget.”

Oakley has one RULE:

  • Be Relevant – stay true to the core of the brand.
  • Be Unexpected – if it doesn’t surprise people, they won’t notice it.
  • Be Likeable – create something people can connect to on an emotional level.
  • If it’s all three of these things, it’s E

Oakley attested to Maya Angelou’s famous words, “People will forget what you said, people will forget what you did, but people will never forget how you made them feel.”

“Don’t take no for an answer. Go around the roadblocks.”

When the “Bush-Gore” billboard made national headlines, Oakley had no idea that 22 years later, he would top that.

Like many during the pandemic, the team at BooneOakley wanted to help increase vaccination rates. The plan? Another billboard, but with just a few words, – “Don’t get vaccinated,” and a fake funeral home logo.

Multiple “no’s” and roadblocks later, they found a way.

Oakley found Garrett Crenshaw, a recent Clemson graduate who owned a mobile billboard company. Deciding that this was even better than a static billboard (since it also looked like a funeral truck), BooneOakley and Crenshaw were quick to begin. On September 19, 2021, this mobile billboard drove around Charlotte for 6 hours during the Panthers/Saints tailgate. When onlookers would search Wilmore Funeral Home, they were met with a bold message: “Get vaccinated now. If not, see you soon.” The website drove users to StarMed Healthcare, where they could quickly and easily schedule a Covid vaccine appointment.

The campaign went viral and garnered national attention – and increased vaccine appointment rates 22% in the following weeks.

David Oakley is truly one-of-a-kind, full of stories and life lessons that go well beyond advice for advertising professionals. Collaborators & Cocktails range of attendees left the event smiling – energized and inspired to make the most of their time with this brilliant original.