Des Moines adman Connor Flynn began a project last March that may be impossible to complete, but which will undoubtedly be of interest to many older business leaders. 

The 66-year-old, semi-retired head of Lessing-Flynn, Des Moines’ oldest advertising agency, is compiling a history of local advertising firms. 

So far, he has a list of more than 80 agencies that have operated in the metro area since 1907, which was when Paul Lessing started producing direct-mail pieces to help farm equipment and seed dealers reach rural customers.  

Flynn’s grandfather, Roy Flynn joined Lessing in 1913 and took over the business when Lessing died of a heart attack in 1933. 

Lessing was a talented copywriter and Roy Flynn was a super salesman. The pair made a strong combination at a time when advertising was handled in-house by most businesses. 

Connor Flynn describes his grandfather Roy as “a diminutive 5’4” and says he “earned his nickname, Tuffy, at local bars.” 

Tuffy would, at times, “leave on client calls and not return for days,” Flynn said. In fact, on one occasion after a rather lengthy “client call” in Clarinda, Flynn said his grandfather “showed up several days later curled up inside his roll-top desk.”

Flynn’s notes on the first two decades of the 20th century are pretty sketchy, but he records two noteworthy events from the 1930s. 

One was the creation in about 1935 of Carey-Hill Advertising to handle franchisee communications for Roto-Rooter, the drain-cleaning business created by Des Moines businessman Samuel Blanc. Carey-Hill was successful for many years, but folded not long after it lost the Roto-Rooter account to Lessing Flynn in 1955.

Carey-Hill was an early example of a phenomenon that became more widespread during the 1960s and 70s: one-client agencies, created by former employees of the client. Most either merged with a larger agency or failed when another agency captured the client’s business. 

Also during the 1930s, a Cedar Rapids agency was founded that was originally named for its founder, W.D. Lyon, but which eventually merged with others, eventually becoming CMF&Z when successful Des Moines adman Bill Fultz joined the group during the 1970s, helping to make it one of the best known agencies in the state. 

Much modern lore of the local ad industry has its roots in the post World War II era, when a man named Wesley Day left the news desk of the Des Moines Register and Tribune to create his own agency. 

The way Flynn and others tell the story, fear had as much to do with Day’s move as opportunity. “He was terrified of the spikes which were used to route edited copy around the rim of the old news desk,” Flynn said. 

That may sound absurd today, but I retired one of those spikes to my home office years ago and it is 15 inches long, pointed and sturdy; it would be a formidable weapon in a knife fight. 

Other R&T employees also left the newspaper to join Wesley Day & Co, including such well-known reporters as Walt Shotwell and Bob Hullihan. My father-in-law Knox Craig, a talented editor whose career had stalled on the city desk, also made the switch. 

All three later were lured back to the Register by Michael Gartner during the 1970s, but not before Shotwell had helped turn Wesley Day into the largest agency in the state by signing the Iowa Republican Party as a client. 

Wesley Day & Co., eventually disbanded after the founder suffered a massive debilitating stroke, but many of its alumni went on to form their own agencies or become stars at other agencies, including Abe Goldstien, Jim Bowermaster, Louie Laurent, James O’Malley Boyt, Celia Wright and Al Essman.