Posted by:DJ DiDonna | Published: December 7, 2021

Boilermaker and former Angie's CEO's 3 tips

Advice for business and life

The following article on Bill Oesterle (Alpha Delta/Purdue 1987) was written by DJ DiDonna and can be found here

Bill Oesterle headshot

One of my first tasks at my first job out of college was to buy an old fire truck, drive it across the country, and figure out a way to get it into—as in physically inside—the office. This is a sentence that sounds normal only to those who worked at Angie’s List during the breakneck growth years leading up to their IPO.

But it’s neither the weirdest, nor in any way out of the ordinary for life as a Lister.

My budget was $2,500, and my timeline was three weeks, both of which were completely absurd parameters. But, like Steve Jobs, former Angie’s List CEO Bill Oesterle is a marketing genius with a reality-distortion-field which has a way of empowering people to produce the impossible. 

Bill also recently announced his diagnosis with ALS, which spurred hundreds of Listers from all over the country to reconvene for a reunion at Angie’s List headquarters on the east side of Indianapolis. Rarely do we get time to express gratitude to someone before it’s too late, so I wanted to take a moment to share three lessons from my time at Angie’s List that have stayed with me for over a decade since my departure.

Lesson #1: no job is beneath you

First of all, obviously jobs like the fire truck weren’t high stakes, but like so many similar stories—say tasking one of your most important employees (Chris Austin) with finding a Kiss vending machine while we launched a dozen new markets across the country—they remain top of mind for more than just their absurdity. They instilled an ethos of scrapiness and magical realism which enabled everyone from bottom to top to try the impossible. But first, you had to start at the bottom.

I had a degree from a relatively fancy University, and an even fancier title of Governor Orr Fellow, but that didn’t stop either the COO from putting me in the customer service call center for 3 months to really learn the business, or the CEO from yanking me out from time to time to give me odd jobs (in the most literal sense of the word) like the firetruck mission. When I joined in 2005, just about every employee had to strap on a headset, plug into our soul-destroying telephony software, and take hundreds of successive calls from customers.

Working in a call center should be required curriculum for every human on earth; it’s like being a server at a restaurant, but instead of simply being hungry, crankiness is the base requirement for your customers. Trying to keep your cool while someone blows up at you while struggling through the inane script which determines your bonus has given me more patience and compassion for others than any sermon or lecture. In its best moments, working in customer service illuminates the humanity of those on the other line—I vividly remember looking through the notes during a call with an elderly woman where my colleagues had urged those who took a particular caller to be gentle, as she liked to talk because her husband had recently passed away. We kept giving her the same plumber recommendation, regardless.

I sat between a middle-aged pastor and a biology major who was trying to steady his spiraling world after getting rejected from med school. The former was an uncomfortably good salesperson. The latter ultimately rose to lead a sales team responsible for tens of millions of dollars of revenue.

One day, I got my big break: my manager Ed Sherman was leaving for vacation, and I asked if I could help him by taking over the weekly sales report, an email painstakingly constructed by compiling spreadsheets from several departments. I took the opportunity to reformat it, so that it would be easier to read, and to make a few other tweaks. I held my breath when I sent it out to the entire company, but was relieved when positive responses started pouring in—I was getting noticed! But, my heart stopped when I got a reply from the COO Scott Brenton, saying “come see me in the conference room ASAP.”

If Angie—yes, there’s really an Angie—was the face of the List, and Bill was the heart, Scott was its passionate spirit. Scott also hired me, so I felt his praise—or criticism—acutely. He famously carried two markers, one red and one blue, and visibly marked up all papers in his vicinity in real time during meetings. You didn’t want the red pen, but you knew which one you got as the color of his face approached the pen's hue. This meeting was a red pen meeting.

Scott had already printed out the weekly sales report, and there was not a blue mark in sight. “Why is this number wrong,” he asked. I had no idea—I’d just copied and pasted the formulas from Ed’s sheet, and had run it both ways to make sure they were the same. I told him as much, and that it was Ed’s formulas, not mine, that were off. I figured we were done. We were not.

“You just sent this out to the entire company, so these are now your numbers. Just because you’re smart, it doesn’t mean that this job is beneath you. Have some f*cking pride in your work, and take some g***amn responsibility, man! ”

I tucked my tail and scurried back to the cubicle farm that was the call center. Scott was right, of course, and it’s a lesson that has never left me. Over the next three years, I was promoted several times, leading teams of temporary data entry positions, sales teams and creating analytics teams, but I never forgot to own my mistakes, be kind to customer service reps, or to think from the perspective of the customer. 

Lesson #2: give people first chances... and also second ones

Bill has the gift of x-ray vision for talent. Unlike most folks I’ve met with his pedigree—especially ivy-league MBAs—Bill is quick to give people a chance, and to judge them by their performance, instead of their resume. This characteristic could be a double-edged sword.

In his weekly “Bitch with Bill” sessions, where he took very live, unfiltered Q&A from staff at all levels, Bill would be more than eager to take suggestions. But there was a catch: the asker would almost always be deputized on the spot to solve the issue they brought up. This resulted in a lot of “special project” assignments which could frustrate the managers of the deputized employee.

Bill’s propensity to give people a chance at things certainly benefited me: after just six weeks in the call center, I sold someone a “lifetime membership,” which to be clear, we definitely did not have, prompting him to promote me to manage a team of twenty, effective immediately. I was completely in over my head, hiring, managing, and training a team of hourly data entry workers, most of whom were twice my age. In true Bill fashion, as if that wasn’t enough to take on, he suggested (read: insisted) that I hire a recently released felon who wasn’t on my radar. I have no idea how Bill found the guy, but it was clear that he was not to be fired, no matter how much management it took for him to be successful.

While at the time I was frustrated—and a little scared, to be honest—in retrospect, it was an example of how Bill constantly went out of his way to help others. Our office was a constant parade of (questionably behaved and named) rescue animals. Our mailroom was run by, and, it was rumored, housed, a former homeless person who Bill hired and who ultimately grew the team to manage five. I shouldn’t have been surprised that a part time widower who ran our books was in the front row of Angie’s List’s IPO shot in Times Square. 

Angie's on NASDAQ

When Bill took you out to lunch, it was to a dive bar owned by the struggling entrepreneur down the street. When big shot VCs were in town, he brought local HVAC small business owners, plumbers or handymen to the meetings so they could talk about the difference Angie’s List had made to their businesses and in their lives. Bill gave me my first chance and countless others their second chances; in doing so, I learned that kindness and success didn’t have to be a tradeoff.

Lesson #3: every business can be a social enterprise

“Save cats, drink beer and grow the business, it’s not that complicated, really.”

For a while, this was the unofficial motto of Angie’s List, emblazoned on t-shirts given to its highest performers on our quarterly “Stan’s Club” celebratory trip away from the office. But it wasn’t until I started my own company, that I realized both how difficult, and how profound Bill’s perspective towards helping others was.

If I’m being honest, I was a bit of a social impact snob coming out of college. The only reason I’d taken the job at Angie’s List—which I’d dismissed after getting an offer as a fancy yellow pages—was because I had gotten denied by several international service organizations. Throughout college, I’d been set on helping people...only to end up at a job which helped people fix a leaky toilet? I was determined to make my time at Angie’s List only a quick stopover onto a more impactful career.

In my last weeks before going to business school, Bill pulled me aside to offer some advice. We were on a cruise ship, along with dozens of people from every department who’d earned a Stan’s Club trip.

“Listen, I know you want to get out of Indiana and go help people abroad,” Bill said to me, over the howl of bad karaoke in the cruise ship’s bar, “but take a moment to look around you. Many of these people don’t have college degrees. Some are single parents who have never been out of the state. Don’t underestimate the value of providing a good, stable job, with benefits, camaraderie and the hope of a better future.”

A dozen years later, the social impact of Bill’s very much for-profit endeavor continue to pay dividends. Angie’s List alums have started dozens of companies, employing hundreds of people in the tech industry in central Indiana. While propelling the company to a $500 million IPO, Bill single-handedly reinvigorated a downtrodden area of town, and changed the lives of thousands of employees, neighbors, and (who could forget?) rescue animals.

Bill taught me that company culture was not just good for hiring—it’s one of the highest-order things you can do as an entrepreneur. Five years after I left the List, HBS published a case about my company’s culture, which shamelessly copied the retreats, celebrations, flexibility and soul on which Angie’s List ran; Bill’s impact had spread to all corners of the planet.

The three years I spent at Angie’s List were, without a doubt, the most formative and educational of my life. I learned more about management than I did at Harvard Business School—though it helped that the executive leadership team all had degrees from the place. I also owe the fact that I even considered going to HBS, let alone got in, to Bill, Angie, Scott and Michael, who were invaluable mentors along the way. More importantly, I am forever indebted to those who managed me, from above (Ed and Michael and Scott and Scott), laterally (Mumau) and for those who were kind enough to manage me from inside my team, even though I didn’t realize they were doing so (and how much I needed it!) - this list is incomplete due to my memory and my ability to find folks online.