Mar 23, 2013 · 5 minutes

There used to be an old saying, "A jack-of-all-trades is a master of none." That was a great concept at one point in time, but now we must discard that outdated notion and admit that we live in an era when “experts” are on their way out.

Ron Johnson is an expert in retail — how is he doing at JC Penny?

Mark Hurd is an expert in hardware — and Oracle has had a miserable impact on my portfolio the last few days.

Arianna Huffington is an expert in journalism — what has she done to improve AOL’s branded content in the last two years?

I could spend the next two pages giving examples of so-called "experts" who have no idea how to run a company, but I’d rather approach this in a few different ways.

At various points, I ran the engineering, product, and revenue teams at Bleacher Report, and I have never written a line of Ruby code, nor have I sold one impression of advertising to a client. Am I an expert in technology? No. Am I an expert in editorial? No. Am I an expert in sales? No. But I’ll wager that there aren’t many people on the planet who understand the confluence of technology, editorial, and advertising better than me.

And I have intentionally built my skillset around being a "generalist," because I do not believe that "experts" are the wave of the future. I think that they are an outdated CEO mold.

I’ll contrast my preferred approach with that of an “expert-driven” one. Few would argue that AOL’s management team is rife with expert executives. But let’s use them as a case study for how a bunch of seasoned authorities can end up creating a Frankenstein’s monster of a company:

Take a look at their most recent financial filing:

aol financials

Notice that their owned and operated properties — ie the real AOL — saw virtually no increase in advertising revenue. This occurred at a time when the industry itself performed quite nicely, as demonstrated by their strong third party performance — ie the sites that are not AOL.

If I were the “experts” at AOL, I would be pissing my pants right now.

If I were the “experts” on Wall Street, who have poured money into AOL stock recently, I would prepare myself for some disappointing outcomes.

Because I, Bryan Goldberg, am not an expert in anything — but I will gladly point out the following holes in this really atrocious business:

  • Their typical user looks a lot like the geriatric technophobes who are still captive to their legacy subscription business. No advertiser wants to reach 75-year-old women.
  • They have "bet the farm" on their largest owned property, Huffington Post, and are furiously pumping traffic to The problem, though, is that advertisers don’t love the Politics business. They prefer topics like Entertainment and Sports, where users are happy and the content is not controversial. The properties that they have acquired, TechCrunch and Engadget, are losing mindshare to new entrants like TheVerge. Patch was an ambitious but poorly executed endeavor. I didn’t even realize that MapQuest and MovieFone still existed until I read their 10K. In short, their "portfolio of properties" is a hospice of properties."
  • Their legacy subscription business is far more closely linked to their media business than Wall Street understands. A lot of these people — like my own grandmother — go to to read their mail, and then follow those links to the media properties. That traffic source is not a stable one.
  • They have yet to launch a single brand with any efficacy. They do not know how to create a media property. Their only option to buy one. And they just gave away their cash in a special dividend.
  • Their weak presence in mobile is currently a benign problem — perhaps even a temporary strength — but that will change radically in the coming years, when innovators begin "cracking the code" on mobile, and dollars start to move there faster.
  • HuffingtonPost hemorrhaged way too much talent. AOL kept the least valuable person on that executive team.
AOL is the walking dead — if I were an investor, I would short the company. But I’m not picking on AOL just to be a jerk. I’m doing it, because AOL is the poster child of a company that is run by “experts."

Tim Armstrong is celebrated as one of the world’s greatest authorities on advertising sales. Arianna Huffington is the face of modern journalism. Until recently, they had one of the most respected COO’s in the business. And this panel of experts is failing, because they don’t have any person who really understands the coming together of these three distinct trades. The best thing they did was to sell some patents. Starting a company, though, is a different matter.

Bleacher Report thrived because we had some very seasoned experts in our company who held executive positions. But what really catalyzed our success was that the founding team could bring it all together. Short of that, you would have had a boardroom where the editors, engineers, and salespeople were talking past each other and growing frustrated.

And I’ll bet that AOL is rife with editors, engineers, and salespeople talking past each other, getting very little done.

Let’s face it — was Steve Jobs really an expert in anything? Would a typography professor give him much credit? Would Steve Wozniak really credit him with any great hardware expertise? Would Tim Cook or Ron Johnson concede that Steve knew supply-chain or retail better than they did?


Apple thrived because its CEO was a jack-of-all-trades who stood atop a mountain of experts. And he knew when to listen to each one, and when to stop listening to each one. He knew when he was being bull shitted, and he knew when to dig deeper.

And what about Jack Dorsey? He knows as much about sailing boats and tailoring clothes as he does about technology or credit processing. I’d rather get my suit fitted by Cable Car Clothiers or trust a naval veteran with my sailboat. But Jack Dorsey is the guy to invest in. And don’t even get me started on Elon Musk...

I’m no Steve Jobs or Jack Dorsey, but I’m definitely no Tim Armstrong or Arianna Huffington. I intend to launch a Web company that is highly competitive with AOL, and I plan to do it in the near term. Because I will be able to hire expert engineers, expert editors, and expert salespeople, and I will be able to bring it all together.

Me, the guy who is an expert in absolutely nothing.

This century belongs to the jack-of-all-trades, and the VCs and Wall Streeters who put their confidence in the esteemed “experts” are going to get very badly burned.

[Illustration by Hallie Bateman]