As the media industry starts to look more and more like the technology industry, we’re learning some of the language and practices the Bay Area and Silicon Valley.

“Agile development” is used across many media businesses (including TheMediaBriefing), the concept of “lean” is embedded in many and the product-focused, user-driven approach is gaining traction.

But what about one of the most enduring tech maxims: fail fast? Surely for legacy (and new) media businesses, failure isn’t an option?

Entrepreneur Tim O’Reilly, famous for his eponymous computer book publishing company, has written a thoughtful and fascinating account of the things he got wrong over the last 20 years, as well as his successes. There are several lessons in failure there for media business leaders today that are worth spelling out:

Is your message really getting through?  

O’Reilly started and ran his business as one with a social conscience, not as a corporate juggernaut hell-bent on making money. Cash generation was necessary but not the end game. But did staff take this the wrong way? As he says:

As a result, we’ve had countless struggles to have employees take the business of the business as seriously as they should. I was always pretty good at finding the sweet spot where idealism and business reality meet, but I didn’t spend enough time teaching that skill to everyone on my team

Re-think what HR is for

O’Reilly wrote an inspiring HR manual that left staff to their own devices, allowed them unlimited leave as long as “no balls got dropped” and set out no formal salary structure. When the company expanded to 60 and then 100 staff it became harder to manage and little by little the traditional HR practices came in. He now says:

I focused my energy on product, marketing, finance, and strategy, and didn’t put enough time in to make sure I was building the organization I wanted.

Cash is king

You might be profitable, but how much money is flowing into your business on a weekly basis? The dotcom boom hit O’Reilly hard – it was making $250,000 on average per title i the 1990s, which fell to less than $100,000 after the bubble popped.

Yet during the 90s, we were always bleeding cash, while since the bust, we have put tens of millions of dollars in the bank through positive cash flow. That has given us money to invest in new ventures and business transformation as the world continues to change around us.

Choosing the right people… to stay

This will ring true for a hundred media businesses. When laying off staff in 2001, O’Reilly says that while some people were talented, he was “appalled to learn there were some people who had built themselves a nice, cozy position but weren’t working very hard.”

O’Reilly stresses the importance of working with HR and financial professionals to find out where the wastage is and where the new talent might come from. when  it comes to firing people, he warns of the tempation “to accept 60 percent or 70 percent of what you wanted because you think you can’t afford the time and trouble to find a replacement.”

Again, I reccommend you read the whole piece in full if you haven’t already.


There are many more we could add to a media-specific list, such as the slowness to move to rival platforms at the risk of cannibalising print revenue, leaving the door wide open to classified advertising aggregators. Or mistaking experimentation with investing in the cheapest, most cost-effective digital products available. Or cutting budgets to maintain profitability at the expense of product quality. We could go on.

So I must ask: would you admit your biggest failure in business, and if so what is it?