Professional Development
Business development

That time I split my pants in a pitch meeting: a CEO failure story

On the road to his company's first five-figure contract, cofounder and CEO Christopher Wink made a series of humiliating gaffes. He's better for it. You will be, too.

Sometimes we aren't as prepared as we think we are. (Photo by Marten Bjork via Unsplash)
This is part of a semi-regular series about embracing failure.
It took me eight years to become CEO of the company I founded and led. This is an example of why.

I’m now the CEO of a 20-person company that publishes, the site you’re reading now. In February, we celebrated 10 years of reporting on local economies in change, including daily reporting in D.C., Philadelphia, Baltimore and Delaware, and extended coverage of Pittsburgh and Brooklyn and a half dozen other cities.

Like a lot of startups, particularly those that produce journalism, we didn’t always know exactly who our customer was. Even more because we didn’t know who we were. But we have always bootstrapped, built on our own revenue, so we’ve had to figure out fast.

I remember how I led to our first-ever five-figure client. It was a months-long series of humiliations that helped me grow into the better leader I am today. Like most series of failures, there are at least three lessons from the experience.

1. The difference between iconoclast and being an ass

First, on lead generation. Toward’s beginnings in 2009, I was maybe 25 and asked to join three very accomplished journalists on a panel at a very blue-blooded club of 300 regional executives in Philadelphia. The topic was the future of news. It was a polite crowd of gray-haired executive directors and CEOs and VPs interested in what was happening to the Great Recession-sped decline of newspapers. I was on the panel to be some kind of foil to the esteemed veterans.

From my own experience and reporting on others for years, I’m here to tell you that often young founders have a telling handle on the future. Rarely do they know how to get there. We should listen to them more than we should follow them. Looking back at us, we fit the mold: our vision of the local news world was prescient, but we stumbled on our way of getting there.

During the hour-long conversation with news veterans,  I grew frustrated with what I felt was outdated thinking how to support and grow a journalism environment in a post-advertising digital world. I began to curse, liberally, in front of a staid and polished audience.

I finally interrupted one of the newspaper executives whose career tracked the decline of a 20th century news model by shocking a bundle of patricians. I said: “You just don’t fucking understand.”

There were audible gasps. The moderator scolded me, to several claps of agreement. I thought of myself as truth telling but I was misreading the room I was in. I could have captured the attention of hundreds of potential funders. Instead I was embarrassed.

[Editor’s note: This is a recording of a version of this story being told a public event last month.]

2. Being prepared and professional

Second, on fitting the part. From the ashes of my early erratic public performance, I was not overwhelmed with opportunities. I did get a single voicemail from an executive who appreciated my “colorful presentation” and was interested in learning more. He wanted to hear our advice on publishing strategy for brand building and where the future of news was going. This felt important. I scheduled this big meeting with the chief executive of a 100-person company.

At this point, I was making more money by landscaping and performing other odd jobs than I was with my fledging news organization. My two cofounders and I held our meetings in our respective apartments. Mine had a mouse problem and a couch that sat on crates. Sometimes I’d buy pizza from around the corner with loose change.

Meeting with the CEO of a 100-person company might as well have meant that I was meeting with the U.S. president.

The morning of the meeting, I put on the best outfit I had. This included the blue blazer I wore to my junior prom and the good khakis I bought from Goodwill. I arrived to his offices 45 minutes early and did laps to shake my nervous energy. His assistant brought me into his office. It had both a desk and a separate seating area. I imagined that I would someday have my own separate seating area.

The meeting started well. He was amused by my energy, interested in my perspective. I was discovering my way, despite not quite understanding what I was supposed to do in a meeting like this.

About halfway through our conversation, when I shifted my crossed-legs, I went white with fright. I realized what I remembered to be a small tear in my secondhand khakis had become a baseball-sized hole in the crotch of my pants. I pulled my legs tight together and stammered. Already unfocused, I relied even more heavily on my prospective CEO client to lead me through the meeting.

Patient and luckily charmed by me, he guided us. Not to a place that was most strategic for us and our goals — that would have taken real preparation on my part. But he graciously let me leave with a nugget of how I might help share insights we were using to build our news organization for his content strategy plans. I would be starting my company’s revenue-generating work off-focus, because of my lack of preparation and vision.

3. Valuing yourself in a marketplace

Third, on valuing yourself. I prepared the proposal with my cofounder in his apartment’s backyard. He nervously smoked cigarettes. The extent of our market research and price comparing was a direct message I sent to the only person I knew who had what I perceived as a serious job, a 30-something who was a junior manager at a big corporate. I likely asked something no more nuanced than, “uh, how much are contracts for?”

We simply started to estimate how many hours it might take us to complete the project. The best paying job I had at that point in my life was working for a plumber at $15 an hour, so I started there. I made it $20 an hour instead. “Because I’ll need to buy new khakis,” I said.

After putting the proposal together and totaling the math, my cofounder and I looked at what was the largest dollar figure we had ever considered: $12,000. We were giddy. I looked at him, and I said: “I think we should double it.” With a few adjustments, we did, finalizing a $24,000 proposal, more than either of us had ever made in a year, to be done in just a few short months.

We sent the proposal to the client, and it was approved faster than we ever imagined. We put nearly full-time hours into the project, conceiving of an editorial, social and branding strategy. We became junior crystal ball readers of where the web would be going. Annoyed executives questioned what these 20-something consultants were doing in important meetings.

Toward the end of the project, the CEO, who had taken a liking to me, pulled me aside. He wanted to give me advice on the proposal cost. He said to me: “You should have doubled it.”


I laugh quite heartily at these memories now. Then, though, they each were heart-wrenching moments of embarrassment. I wasn’t ready to be CEO then. I wasn’t even ready to be a professional. But we pushed through. We worked hard. We matured. I started buying pants that fit me, and got rid of them when they turned threadbare.

We all grow at different paces. Failure can help speed the process.

Companies: Technically Media /
Series: Behind the Scenes

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