Beware the smart billionaire at your pitch

I had just wrapped our AOL pitch when Ted Leonsis asked me a fatal question I didn't have on my bingo card. And the worst thing was, he was right to ask.

Jun 16, 2025

At DDB, I’d been consulting to AOL, and we’d earned a shot in a shoot-out for a new AOL campaign.

With good buzz in the room at the end of the presentation, I’m standing front and center opening the Q&A when Ted Leonsis leans forward, hand raised, with what seemed like an innocent request: “Can I just ask you a quick process question first?”

“Why of course,” I say, with a welcoming smile and a come-ahead wave.

A few seconds later, we keel over dead.

A little back story…

It was 1999, and AOL was partying like it was—you know.

And they had plenty to celebrate.

The Dot Com Boom was stratospheric, and AOL was selling massive ad buys directly to marketers while brushing lowly ad agencies aside as Luddite meddlers.

Their arrogance was understandable, if not excusable. While agencies were struggling to crack the digital advertising code, several AOL salespeople were flying over agencies on their own private jets, laughing all the way to the bank. (Yes, not just the AOL jets—their own personal jets…)

New millennium, new realities

The millennium turned, and so did AOL’s reputation. Agencies and marketers got smarter, had more digital ad options, and AOL’s arrogance started wearing thin as the Boom turned Bust in the spring of 2000.

A close friend from my FCB San Francisco days, Richard Ward, was at AOL at the time, and reached out to me with a crazy idea: Would DDB be willing to consult to AOL and help them mend fences with the agency world?

The bait was juicy—I bit

We nailed down a $100k/month deal for me and DDB to help redeem AOL with ad agencies.

Here’s a day on the road as Richard and I try to inflate our wobbly AOL/DDB dirigible:

I’m in Paris, working with leaders of our French agency before an AOL EU summit meeting
Next day, DDB assembles at the appointed hour—but where’s AOL?
I finally get a text from an embarrassed Richard letting on that his boss had detoured them for a quick personal errand
An hour late, in they stroll, strained smiles and greetings all around, and we get down to work. But despite Richard’s savvy leadership and all our pre-work, I have no memory of any output because nothing ever came of it

But I do remember the errand: The boss had to swing by his bespoke French cobbler for a shoe tree fitting to help maintain his custom oxfords. I had to ask: $3,000 trees to maintain $15,000 shoes. That’s about $33,000 total in today’s dollars.

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The fall of Rome was well underway

A year later, AOL and Time Warner merge in an infamous $165 billion deal. In less than two years, they take a record-breaking $99 billion goodwill write-down, and the net value destruction exceeded $200 billion, widely rated the worst deal in history.

Back to the Leonsis pitch question

Waving a pointed finger back and forth across the wall behind me, Leonsis asks me, “Did I hear it correctly that you did all this work for no money?”

I shot a glance at the stone-faced consultant who ran the pitch, then looked back at Leonsis, nodding, and said, “Yes, that’s how it works.”

My answer hung in the air like Sarin gas.

I take the chump-fall for decades of agency giveaways

Leonsis slowly leaned back in his chair, shaking his head while looking around at a few colleagues, enlisting their participation in group shrugs and eyebrow lifts, miming, “can you believe these fucking idiots!?”

From there, how could we be considered worthy to shine their fancy shoes, much less be responsible for their precious new brand campaign?!

A fair and fabulous question

I don’t believe that was a planned ambush. I think Leonsis was a board member, far removed from pitch-world, gob-smacked by learning the stupidity of the pitch process. (And yes, back then, agencies often signed away rights to anything and everything presented in pitches for either no money or a tiny token payment.)

Ten years later, I step in it again

You’d think I would have remembered that.

When I had my NY agency Protagonist, a great young account person brought in the owner of a hot new beverage brand for a credentials pitch.

The meeting goes well, and I agree to a second “chemistry session” to, in the brand owner’s words, “see if we’d be a good fit.” At one point I say two words in a conversation about the brand’s points of difference, and lo and behold, we are ghosted, and I had the distinct thrill of seeing my two words rolling by me for months on the sides of New York City buses and subway cars, the anchor slogan of their new campaign.

What have we learned here

Never give away your insights or creative work.
1. When fishing for clients, it’s easy to dangle juicy idea-bait in front of prospects. But once bit, it’s hard to pull that bait back.
If leaders of an advertiser or media company make mountains of money that just don’t make sense, given the value they deliver, beware.
1. A current example: according to The NY Times last week, the CEO of The Trade Desk, a big digital ad platform, made $589,380,201 last year in what the NYTimes calls “‘Compensation Actually Paid,’ the newer accounting measure emphasizing the annual changes in the value of an executive’s current and potential stock holdings.”
2. Yet experts have pointed out for years that fraudsters—from individual bad actors to rogue states—have penetrated these “programmatic” platforms so deeply that most client ad dollars are stolen, with the vast majority of ads ”served” likely never seen by a human being. (I covered this topic at length in April—see link to my story below if you missed it.)
If your friend and client’s boss is paying $33,000 for a pair of shoes and shoe trees, maybe ask for a raise (Yup, didn’t do that, either.)