"Nobody Knows What They're Doing"

Don't let your assumptions about others' greatness kick you in the ass

Watching the big dogs of advertising at the Cannes Lions Festival

I’ve always felt like an underdog in the business world. I didn’t get an MBA from Harvard. I don’t have millions of followers awaiting every Tweet. I’m still waiting for an invitation to Davos and Sun Valley. I’ve not been a 30-under-30 or 40-under-40. Now I’m over 50.

I’ve had some solid business successes in a medium-sized city known for odd-flavored chili and being ten years behind the times. This is not a complaint! I’m proud of my businesses and love this town. But sometimes, I wonder what it’s like to be in the room with the global business heroes. I daydream of sitting at the feet of Bezos or Buffett and long for the wisdom to bring my own game up several notches.

I’ve had the chance to rub elbows with the movers and shakers a handful of times, and it usually reminds me of a critical lesson in life…

The A-List Agency Pitch

It’s a Monday in October 2008, and I’m on a 6:07 am flight from CVG to LGA. That’s Cincinnati to New York/LaGuardia for those who have not logged a million SkyMiles. I’m 6’3” and stuck in the middle seat, sandwiched between two sweaty guys in suits who have stolen my precious elbow space. I’m the meat in a manwich today because this trip was a last-minute opportunity for my little digital agency to join a +$100 million new business pitch led by a massive, accomplished sister agency within the holding company that bought our business a few years earlier.

We sold our company at the end of 2005 in a deal where 90% of the purchase price was based on our revenue and profit growth at the end of a 5-year earn-out. My fellow shareholder execs and I had a lot riding on hitting a significant growth number. Our expectation—and the promise from our buyer—was that other agencies in their network would be excited to partner with us to help deliver digital campaigns. We had real expertise in the emerging digital world, and we were put into a group called “Special Services.” In theory, this position meant we could freely partner with any of the dozens of other sister agency brands.

But 2.5 years in, with some big number goals still far on the horizon, we had zero business from the network. Our CEO had spent these past years flying around the country pitching us for partnerships, but nothing was doing. We learned that being in Special Services was like living in the Land of Misfit Toys. Our agency was independent, so the big sisters couldn’t get credit for our revenue. They’d rather fake digital on their own than make it with us.

And the Madmen on Madison Avenue looked down on us as a puny little “job shop” in Cincinnati, Ohio. We had no fancy creative awards on our walls, and our executive team came from the brand marketing world.

No one was looking for us until we finally got a call from one of the very top agencies in New York City. They had a chance to pitch for the global launch of a new brand—a financial services business being spun out from one of the big car companies. They were told they needed a legit digital solution—no faking it this time—and all their preferred partners were conflicted out.

So I’m on the plane, headed in for the biggest pitch in our company’s history. I was somewhat nervous. This was a massive opportunity for our business, and I didn’t want to screw it up. But I was mainly excited—this was getting called up in the major leagues and a chance to experience a massive agency pitch with an A-list firm. As the little guys, we always wondered what it was like at this elite level, and I couldn’t wait to learn and improve through the experience.

I get off the plane, make it through traffic to Agency HQ, and find the company's President—let’s call him James—who will lead the pitch personally. He tells me to grab a desk and wait for a bit. Several hours later, at 2 pm, he finds me and says we’re going to lunch. We head to a sushi place where everyone on the staff seems to know him, and we’re escorted back to a tatami room. For the next 2.5 hours, James orders us round after round of sushi plates and sake bombs as he shares story upon story of his exploits and celebrity encounters from a career in the advertising big leagues. My learning has begun.

We stumble back to the office that evening, and the rest of his pitch team—basically his entire executive group—wander in for the kick-off to the big event. The strategists start strategizing, and the research guy whiteboards some questions. Then a new guy enters the room—it’s the global creative director I’ve read about. Let’s call him “Barr.” Barr asks a few questions, says a few things, and heads out. Other people wander in and out, and I eventually leave for my hotel room.

The rest of the week was more of the same. There were no firm schedules or agendas, but there were more long, boozy lunches and zero progress. I flew home that Friday and flew right back on Monday—to more of the same.

By the third week, tensions were increasing as the first client presentation was coming up fast. We had no strategy or creative direction. We minions asked James for direction, and he replied: “No worries, Barr will present The Big Idea tomorrow.”

Tomorrow is here, and I’m in our conference War Room, which is beginning to get that funky grease smell from pizza boxes that have sat out for too long. We’re waiting expectedly for Barr to arrive and bring us the glorious pitch idea. I’m a cocktail of anxiety and curiosity because I’m not sure we’ve given Barr any box to think creatively outside of. But he’s won multiple awards and produced Super Bowl ad campaigns that we’ve all laughed and cried over. This is where the magic happens…

Barr enters the room carrying one of those black-paneled cases that creatives use to transport their work. He’s smiling and looking confident. He announces, “Here’s the idea: A 10-story woman lumbering through a city. She’s a puppet without strings. The Big Girl.” And he pulls out a sketch of this frightening kaiju.

Everyone in the room is smiling, nodding, and saying things like “Yeah!” and “Perfect!” I bow, cover my face, and think, “What? The? Fuck?”

I hit my breaking point in that meeting. The absolute cluster of a process and the Big Girl outcome blew my mind. There was no greatness to observe here. There was no A-Game. There was nothing to learn, and it was a giant waste of time. We pitched, lost badly, and never got any big business from this or any of the other sister agencies.

Years later, “James” was terminated for a MeToo incident. And “Barr” became the head creative leader of one of the most successful consumer brands in the world. Half of you are currently reading this post with one of its products. Oh, and that Big Girl commercial? The agency re-used the concept for another client who bought it. You can even see it for yourself.

But it all worked out for our company. With no partnership assistance, we grew our revenue from $10 million to $40 million in 5 years. We maxed our earn-out and even won some big-time creative awards. And I learned that the best and the brightest industry stars are often just the luckiest—and that everyone is making stuff up as they go along.

The Mighty Usually Fall

Instead of assuming that other companies or people are better than you can ever hope to become, it’s often better to carve your own path and trust your ability to learn and improve.

Need more convincing? Just look at news stories from the past few weeks. The largest, most trusted, and most successful people and organizations in business show a consistent pattern of screwing up:

• Microsoft launches an A.I. search tool that insults its users.

• Southwest Airlines cancels 17,000 flights over Christmas.

• Venture Capitalists did zero diligence on FTX.

• NORAD misses weather balloons—or are they UFOs? They don’t know.

• Google, Amazon, Facebook, and nearly every giant tech company hire thousands more people than they need.

• Elon…

Why do they all fall? Many reasons: The world is moving quickly, with Black Swans landing earlier and more often. Successful people and companies get arrogant, distracted, and lazy. They stick to an old rulebook that doesn’t matter anymore. Everyone is copying everyone else to cover their asses. There are few single decision-makers with real accountability. The founders who took things personally gave the reins to managers more interested in personal gain.

And everyone’s making up this shit as they go along.

So don’t beat yourself up. Don’t assume that someone bigger than you is better than you. Success stories are just stories, usually amplified by the media and our natural desire to compare ourselves to others in seeking self-esteem. Don’t let them beat you before you get in the game.

But watch and learn from these players in their natural habitat if you can. You can pull out parts of their playbook that work and laugh off the rest.

Bob Gilbreath is a 2x-exit entrepreneur and co-founder of Hearty, a curated matchmaking service that combines top software developers with early-stage, venture-backed startups.