“How I Failed” By Tim O’Reilly

In a candid post on LinkedIn, the founder of O’Reilly Media shares “some of the things that kept me, my employees, and our company from achieving our full potential.”

“How I Failed” By Tim O’Reilly

The “Oracle of Silicon Valley” is known for popularizing terms like Web 2.0 and supporting the growth of the Maker movement. His publishing empire of technical and technology-related books, software, and conferences has nearly 500 employees and collective revenues approaching $200 million. But in a reflective, personal post on LinkedIn, Tim O’Reilly writes this week about what he’s gotten wrong over the years.


Not listening–to himself and to others

O’Reilly talks and writes a lot, but he says he didn’t always practice “reflective listening,” including understanding how well people were hearing his messages. “I talked so much about our ideals, our goal to create more value than we capture, to change the world by spreading the knowledge of innovators, that I forgot to make sure that everyone understood that we were still a business…we’ve had countless struggles to have employees take the business of the business as seriously as they should.”

Not innovating as hard in HR as he did in the core business

O’Reilly says that as his organization grew, he drifted away from practices like merit-only raises, and letting his people manage their own time, and toward more conventional HR policies. Mediocre performers sometimes got a free ride, especially when the business was growing.

“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.”

The experimental flat management hierarchies at new companies like Valve and GitHub make him want to look at “fresh approaches to the questions of how to manage an organization.”

Not counting the beans hard enough

When times got tough, O’Reilly was forced to focus on financials in a way he says he should have done all along. “Where the shit really hit the fan was after the dot com bust of 2001. We were seriously in debt again, our business was in free fall (shrinking by 30% over the next 3 years before rebuilding), our banks pulled our loans and nearly put us out of business….I still remember the day I had to decide which employees to cut in our first-ever layoffs. As I pored over the worksheets, I noticed hair all over my papers. I was so stressed that my hair was falling out.”

O’Reilly Media laid off 20% of its staff; hired a new CFO, Laura Baldwin, who became a core team member and is now company president; and recommitted itself to running lean.


Not delegating

Most entrepreneurs, most leaders, and really, most workers can probably relate to this one.

“…my first instinct was not to hire the team to go after a new product or market, but to do it myself, or with the team I already had.” Gradually he learned to think more abstractly and to invest in people with talents complementary to his own skill set.

[Image: Flickr user Lindsey Turner]

About the author

Anya Kamenetz is the author of Generation Debt (Riverhead, 2006) and DIY U: Edupunks, Edupreneurs, and the Coming Transformation of Higher Education, (Chelsea Green, 2010). Her 2011 ebook The Edupunks’ Guide was funded by the Gates Foundation.