Age 38 | Digital strategy director, Lessing-Flynn Advertising Co.


Josh Fleming has been known to dance to the hit PSY song “Gangnam Style” in the office of Lessing-Flynn Advertising Co., mostly just for fun. People have endorsed him on LinkedIn for “being snarky” and “being ginger” – making fun of his red hair. 

When you feel like you’ve gotten a second chance at life, it may be easier to have a sense of humor.

Fleming’s life changed course when he was 14 years old living in Miami. A boat propeller nearly took his left leg in a water-skiing accident that he says should have taken his life. He spent three months unable to walk and lost the ability to play baseball, which was his passion at the time.

“You kind of build a thick skin and kind of have to laugh it off sometimes, as opposed to just feeling sorry and down on myself,” Fleming said.

That sense of humor, combined with strengths others describe as passion and creativity, has helped Fleming excel at Lessing-Flynn for the past four years.

Fleming moved to Des Moines with his wife about 14 years ago and worked at The Integer Group and Dice Inc. before getting a job at Lessing-Flynn. He initially didn’t see a future in the area, but his job with Lessing-Flynn, combined with more community engagement, has turned Des Moines into a place that “we really kind of fell in love with.” 

One thing he particularly likes about the community is the burgeoning technology startup scene, which he participated in with the launch of his own photo-sharing website, VineMe. Google Inc. and Facebook Inc. have launched similar products, which have made future growth of Fleming’s site virtually impossible. But through the experience, Fleming says he learned how to look at the bigger picture of an organization, something he now uses to help clients focus their marketing strategies.

Fleming has also found a passion for the American Marketing Association of Iowa; he is currently president of that organization.


Five reasons he’s a 40:

• Created AdMavericks.com for Lessing-Flynn, which is now one of Iowa’s most-read marketing blogs.

• In 2010, created Lessing-Flynn’s Battle of the Brands, a social media contest focused on Iowa brands.

• Serves as president-elect of the American Marketing Association of Iowa and on the board of Prevent Blindness Iowa.

• He’s a national public speaker on topics ranging from branding to digital marketing strategies.

• ”Josh has an uncanny knack of unleashing his enthusiasm on projects he feels strongly about and inspiring others to get involved,” said Tom Flynn III, president of Lessing-Flynn. 

Mentor: Jess Held, vice president of client services at Lessing-Flynn

Fun fact: Fleming, who was an English major at the University of Missouri, likes to hone his creative writing skills, and has done so recently by writing screenplays. One, a murder mystery, he is entering into a contest, and two more are in the works.