This Time with Feeling

“As a startup CEO, I slept like a baby. I woke up every two hours and cried.” — Ben Horowitz

After selling Loudcloud’s services business to EDS, Horowitz faced the daunting task of reinventing the company as Opsware, a pure-play software company. With a skeleton crew, a battered reputation, and a stock price hovering near zero, the transformation required everything Horowitz had learned about leadership, resilience, and sheer determination.

The Pivot to Opsware

The transition from Loudcloud to Opsware was not a smooth corporate rebrand—it was a gut-wrenching reinvention. The company went from over a thousand employees to a few hundred. The business model changed entirely, from managed services to enterprise software. And the market had no reason to believe Opsware could succeed.

The Scale of the Challenge

• Stock price had fallen to $0.35 per share
• The company retained only the software assets from Loudcloud
• Most of the revenue disappeared with the EDS sale
• Wall Street analysts wrote the company off as dead
• Remaining employees were demoralized and uncertain about the future

Rebuilding the Product

Horowitz threw himself into rebuilding Opsware’s software product. The company’s data center automation technology was genuinely innovative, but it needed significant development to become a standalone enterprise product. Horowitz made the decision to bet everything on product quality—if the software was not dramatically better than anything else on the market, nothing else would matter.

“In good organizations, people can focus on their work and have confidence that if they get their work done, good things will happen for both the company and them personally.” — Ben Horowitz

Product-First Philosophy

• Invested heavily in engineering despite extreme cash constraints
• Demanded product excellence as a non-negotiable standard
• Focused on solving real customer pain points rather than chasing market trends
• Built the product for enterprise buyers who valued reliability and automation
• Made technical decisions that prioritized long-term quality over short-term revenue

Winning Customers the Hard Way

With a damaged brand and a skeptical market, Opsware had to earn every customer. Horowitz personally participated in sales calls, product demos, and customer negotiations. Each deal was a fight, and losing any single deal could have meant the end of the company.

The Sales Grind

Horowitz recounts going head-to-head with larger, better-funded competitors like BladeLogic. Every competitive deal became a test of the product, the team, and Horowitz’s own stamina. He learned that in enterprise software, the product has to win on merit—there are no shortcuts when you are the underdog. The team developed a relentless focus on competitive intelligence, constantly improving the product based on what they learned in lost deals.

The Long Road to Acquisition

After years of grinding, Opsware built a real business with real revenue and real customers. The stock price climbed from $0.35 to the point where the company attracted acquisition interest. In 2007, Hewlett-Packard acquired Opsware for $1.65 billion—a remarkable outcome for a company that had been left for dead.

What Made the Outcome Possible

• Relentless focus on product quality when everything else was falling apart
• Willingness to make painful personnel decisions to build the right team
• Horowitz’s personal involvement in critical sales and customer relationships
• A culture of transparency that kept remaining employees engaged and motivated
• The refusal to give up even when every external signal said to quit

The Emotional Cost

Horowitz is unflinching about the personal toll of the Opsware years. The constant stress, the sleepless nights, the strain on his family, and the loneliness of leadership all took a heavy price. He writes about this not to seek sympathy, but to prepare other entrepreneurs for the reality of what building a company actually feels like.

Key Takeaways

• Reinventing a company requires courage, clarity, and the willingness to shed everything that does not serve the new vision
• Product quality is the ultimate competitive advantage—there are no shortcuts
• A CEO must be willing to personally engage in the hardest problems, from product to sales to personnel
• The emotional and physical toll of leading through a crisis is real, and founders must find ways to manage it
• Resilience is not a personality trait—it is a daily practice of showing up and making the next decision