The columnist who crossed to the other side of the billboard

The first bank advertisement I took apart was one I had admired. In 2001, as a business reporter at the Lakeward Sentinel, I was comparing savings accounts across Milwaukee for my column and called a bank about a promotional rate on its billboards. The rate was real. It applied for three months, to balances above US$25,000, if the customer also opened a checking account with direct deposit. The banker who explained this was apologetic, and the column that followed was fair to the bank, but I remember thinking that nobody who drove past that billboard could have known what it meant. I have spent the twenty-five years since on the other side of it.

I grew up in Racine, Wisconsin, and studied journalism at Ostwick College in Iowa, graduating in 1998. The Sentinel hired me that July to cover small businesses, and in 2000 I took over its weekly personal-finance column. Readers wrote to me about mortgages they did not understand, balance transfers that had cost more than promised and annuities sold to their parents. I learnt to read a disclosure from the back, to call the company before writing and to separate what a product did from what its advertising implied. I also learnt that a careful explanation helped readers who already trusted themselves to read it, and rarely reached anyone else.

In 2003 a Milwaukee agency, Kessel & Marr, asked me to write for its financial clients: two banks, several credit unions and an insurer. I accepted partly out of curiosity about how the billboards were made. I found that most misleading advertising was not designed to mislead. It was assembled by people who each owned one piece: a product manager who wanted the highest rate in the headline, a lawyer who wanted the conditions somewhere on the page, a designer who wanted white space. Nobody owned what a reader would take away. I became the copywriter who asked compliance reviewers to read a draft aloud to someone outside the building.

Strathmere Home Lending recruited me in 2007 to rewrite its customer letters. Within a year the work had changed. As delinquencies rose, I spent most of 2008 and 2009 on the letters Strathmere's servicing division sent to borrowers who were behind, including offers of loan modification under the federal programme introduced in 2009. Our first letters drew responses from fewer than one borrower in five. Rewritten with the borrower's own figures on the first page and a single telephone number, they drew responses from more than two in five. I have never had a clearer lesson in what plain language is worth, or in how much harm a confusing letter can do. I completed a part-time MBA at Tamsworth University in those years, in the evenings, mostly to understand the economics of the business I was writing for.

From 2012 I ran Strathmere's consumer marketing. My most consequential decision there was to stop headlining a mortgage rate that most of our borrowers could not obtain. It taught me that honest advertising has to be designed with the people who price a product and sell it, not handed to them afterwards.

In 2016 I joined Quillmark Investing, a Chicago online brokerage for people opening their first investment account. I was responsible for the brand and for acquisition as the firm grew from about 400,000 funded accounts to 2.1 million. In 2019 we began paying finance creators on social platforms for each funded account they referred. By mid-2020 they supplied 29% of our new accounts, and I had approved most of them. When one described an options strategy as free money to almost a million followers, I proposed ending per-account payments altogether. The board agreed, our growth slowed and the accounts that did arrive stayed. It remains the clearest test I have faced of whether I believed what I said about advertising.

I came home to Milwaukee in April 2021 as Ledgemoor's chief marketing officer. Our chief executive wanted one brand in place of five product-line advertising teams, and a measurement model our finance colleagues would accept. The deposit scare of March 2023 tested both. In that fortnight I learnt that a bank's advertising and its crisis communication are the same activity at different speeds, and that the most useful thing marketing can do in a frightened week is supply facts quickly and stop selling. The following spring our fair-lending officer showed me that our digital mortgage campaigns, tuned for cost, had nearly stopped reaching some of the neighbourhoods closest to our headquarters. Correcting that has cost money and taken longer than I expected.

Colleagues would probably say that I read the conditions before the headline, that I am more comfortable with compliance officers than most marketers are and that I am slow to approve a campaign whose claim I cannot explain to a customer in two sentences. I would add that I still write. I draft the first version of every rate advertisement we run and of every customer letter announcing a change in terms, because if I cannot write it plainly, the product usually needs to change before the advertising does.

Open to Board appointments · Advisory roles · Speaking invitations

Languages / English