Oh Ship! What’s Your Biggest Professional Regret?

Sean Finnegan and Freddie Laker talk about career mistakes, what they’d do differently, and what they’d never change.

Sean Finnegan, a co-founder of Chameleon Collective, has also been the CEO of Omnicom Media Group’s digital division. A serial entrepreneur, he also advises startups and has founded other companies of his own. He’s held a head role with Publicis as well. A digital veteran, he started his career in New York in 1993 during the rise of the Internet and the dotcom boom. It was a time rife with speculation, uncertainty, and opportunity, and no one could have predicted exactly how things would play out. We spoke with Sean about his biggest professional regrets, how he’s overcome them, and what advice he’d give to young entrepreneurs today.

Coping with missed opportunities

Sean was invited to join some big companies in their startup phase before they became superstars. Sergey Brin and Mark Zuckerberg were talking with him about having him join Google and Facebook, but he turned them down. At one point, Mark Bezos asked him about coming to work at his brother’s firm, and he thought, “There are bookstores on every block. I don’t know what you’re doing, but good luck with your career.”

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His kids now ask him how their lives would be different if he’d gone for it. But he accepts that in the business world and in life, some opportunities are bound to slip away. In terms of which companies will “go galactic,” as he puts it, it’s like a lottery—you can’t know for sure which ones will make it. So many didn’t even survive through the dotcom era, let alone become major players.

Friends at companies that did go galactic truly didn’t know it was going to happen, either. “Retroactively, they became these visionaries,” Sean says. It only seems inevitable after the fact.

Hindsight is 20/20 for some of the advice he’d given in his early days, too. When he sat down with Sergey Brin and Tim Armstrong of Google, they asked him what it would take for Google to succeed in terms of publicity. Sean told them a bunch of average students from state schools could easily handle the job—advice he laughs at now. 

Working with high-profile people

Sean is currently working with his daughter to create a coffee table book on how to network with celebrities. “The number one thing in dealing with people that are influential and of note is to make sure that they realize that you have a genuine interest in working with them doing something mutually productive; that you have something to trade as much as they do, that there’s the ability to bring something to the table, and that you’re not just there to be a fanboy. You see what they represent, you see their platform,” he explains. 

Let them know your specialty and vertical area, conveying what you can do for them. In his case, it’s access to brands. Don’t ask for anything in turn—relationships will become mutually beneficial as you build them, but don’t force it, Sean says. “Don’t be that guy or gal,” Freddie chimes in. They’re used to everyone trying to get something from them, so differentiate yourself by offering something valuable instead.

“Whatever that first question is that you want to ask, don’t ask it,” says Sean. Get to know them as a human instead. If you have that mentality, everything else will follow. 

Advice for new entrepreneurs

With the wealth of tools available today for starting your own business and brands bringing in agency resources and skills, Sean advises young people to start out on their own. He’s currently helping his children build microbusinesses to get their feet wet. 

Spending four to five years in the agency world is a great way to cut your teeth, says Freddie. You can work on a lot of different types of projects and get great experience in agencies in that time. If you stay too long, though, you can get stuck, being pegged as “the agency guy or gal.” 

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Agencies are often more nimble and flexible—they can make quick decisions on culture, investments, and other things, says Sean. He’s marveled at their autonomy. They’re not typically good at building things up inside, but they’re good at acquiring them from the outside and reformatting them within, he explains. You can learn a lot in a short time in this environment.

In fact, working with the C4 Group, his digital media consulting agency, has been the most exciting part of his career so far. Building things from the ground up is much more rewarding than acquiring them from somewhere else, he says, and when you start to hear people talking about your brand for the first time, that’s really exciting.

Like Sean, if you accept the inevitable missed opportunities you’ll encounter and focus on doing the work that you’re excited about, you’ll not only succeed but be genuinely happy as well. And that’s a benchmark we should all strive for!

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“Oh Ship!” is about celebrating the failures, sharing those stories, learning, and laughing along the way.

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Freddie Laker

A veteran digital marketer with experience working with some of the world's biggest global brands. He now focuses on providing interim leadership to PE-backed firms.

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