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.


Presenting the 2013 winners:

Desmund Adams, Principal, AdamsDouglas
Lindsay Alderman, Client operations manager, LightEdge Solutions Inc.
Erica Axiotis, Director of development, Mercy Foundation
Kate Banasiak, President and CEO, Diversified Management Services Inc.
Erin Beamis, Senior vice president of logistics and operations, IronWorks
Jonathan Brendemuehl, Marketing events coordinator, Bankers Trust Co.
Curtis Brown, Economic development director, city of Ankeny
Matt Connolly, President, Generation Green Builders Co.
Lawrence Cunningham, Director of business development, Catchfire Media LLC
Angela Dethlefs-Trettin, Director of community investment and initiatives, Community Foundation of Greater Des Moines
Josh Fleming, Digital strategy director, Lessing-Flynn Advertising Co.
Felix Gallagher, Principal, PharmServ Solutions
Lori Gelhaar, Director of career services/ corporate relations, Kaplan University
Tina Gray Carstensen, Marketing coordinator, Shive-Hattery Inc.
Shane Greenleaf, Vice president/commercial banker, First American Bank
Danielle Haindfield, Shareholder attorney, Ahlers & Cooney P.C.
Emily Harris, Patent attorney and shareholder at Davis Brown Law Firm
Matthew Harris, Division administrator, Iowa Arts Council, Iowa Department of Cultural Affairs
Angela Hilbert, Sales and marketing director, Deerfield Retirement Community
Joey Hinke, President, Miller, Fidler & Hinke Insurance Agency Inc.
Hannah Inman, Director of communications, Iowa Natural Heritage Foundation
Keegan Kautzky, Director of national education programs, The World Food Prize Foundationn
John Lozier, Pediatric interventional cardiologist, Pediatric Cardiology P.C.
Dennis McDaniel, Police chief, Windsor Heights
Rachel McLean, Vice president/consultant, Ruan Cos
John Mickelson, Associate managing director, The PrivateBank & Trust Co.
Keith Olson, Commercial associate, NAI Ruhl & Ruhl Commercial Co.
Matt Ostanik, President, Submittal Exchange LLC
Benjamin Page, Director, Des Moines park and recreation
Dustin Peterson, Partner, McGladrey LLP
Nick Renkoski, Director of marketing and communications, Des Moines Metro Opera
Rachel Rowley, Partner, BrownWinick PLC
John Ruan IV, Vice president, financial institutions, Bankers Trust Co.
Jennifer Soma, Business lead, IDI Actuarial and Product Development Group, Principal Financial Group Inc.
Heather Starr, Real estate agent, RE/MAX Innovations
Aimee Staudt, Director of development, Knapp Properties Inc.
Courtney Strutt Todd, Shareholder attorney, Davis Brown Law Firm
Nikki Sylverson, Event Director, Des Moines Wine Festival Foundation
Howard Tempero, Experience design strategist, Spindustry Digital
Tony Timm, Executive director, Central Iowa Shelter & Services