Engineering Career and Sailing Background:
Diane Greene, the founder and CEO of VMware, has an impressive engineering background. She holds a mechanical engineering degree, a master’s in naval architecture from MIT, and a master’s in computer science from Berkeley.

Passion for Engineering:
Greene’s passion for engineering developed through her interest in sailing. Tuning up sailboats requires technical knowledge and engineering skills.

Mechanical Engineering Project:
In high school, Greene built a bridge with aluminum trusses for an independent project, showcasing her engineering prowess. She also installed a strain gauge and instrumented it to measure deflection.

Statis Course Experience:
Greene initially planned to major in psychology but switched to mechanical engineering after taking a statics course. In a class of mostly males, she declared mechanical engineering to avoid feeling out of place.

Transfer of Credits and Four-Year Graduation:
As she transferred between three different colleges during her undergrad, only her engineering credits carried over. This allowed her to complete her undergraduate studies in four years, despite changing her major.

Early Career and Sybase Experience:
Began her career as a software engineer at Sybase and worked in the maintenance group, where she encountered data corruption issues. Wrote a program to automatically fix the Sybase logs, greatly improving the efficiency of the support team’s work. Collaborated with a Sun engineer, a fellow windsurfer, to create the first asynchronous IO for a database.

Leadership and Restructuring at Tandem Computers:
Joined Tandem Computers with Roberta Henderson, a former Sybase executive known for her technical expertise. Worked with Henderson to transition Sybase to symmetric multiprocessing, increasing the database’s performance. Witness the firing of Henderson due to internal conflicts and left Tandem in solidarity.

Women in Engineering and Education:
Experienced a low representation of women in the engineering field, despite being an undergraduate engineer herself. Observed a decline in women pursuing engineering degrees, dropping from 37% in 1985 to around 18%, but noted an increase at elite schools. Shared an anecdote about a rear admiral’s speech at MIT highlighting the importance of promoting women and underrepresented minorities in faculty positions.

Founding V Extreme and Early Video Streaming:
Co-founded V Extreme with a Stanford friend who wanted to develop a startup focused on low bandwidth streaming video. Envisioned a platform similar to YouTube but faced limitations in technology at the time. Eventually sold V Extreme to Microsoft due to difficulties in hiring a CEO and integrating the company’s vision.

Early Career:
Greene took a break from her career after having a child. She was approached by a VC friend to help out a small company called Newport, which was focused on internet ad serving. Greene’s involvement led to the successful operation of the ad serving technology.

Birth of VMware:
Greene’s husband, a professor at Stanford, shared a paper he had written on virtual session with her. Recognizing the potential, Greene encouraged her husband to file for a patent and discussed bringing the technology to market. Inspired by his work, Greene decided to help start VMware, a company focused on virtualization.

AdForce and Beyond:
Greene helped AdForce find a CEO and guided them through the process of going public. She was instrumental in the company’s success before it was acquired by CMG. Greene’s contributions to AdForce’s product development were previously unknown to her peers.

Virtualization Explained:
Greene describes virtualization as inserting a layer between hardware and the operating system, allowing multiple machines and operating systems to run on the same hardware. This approach enables maximum utilization of resources, eliminating the need to run one application per machine and boosting efficiency.

Virtualization Revolution and VMware Success:
Diane Greene and Gordy Davidson discuss the rise of VMware, a revolutionary company that pioneered virtualization technology. As a pioneer in the field, VMware enabled users to run different operating systems and software side by side, leading to increased utilization and availability. With its innovative vMotion feature, VMware allowed for live migration of virtual machines, enabling seamless upgrades without downtime.

Rapid Growth and Acquisition:
VMware experienced exceptional growth under Greene’s leadership, achieving over 100% annual growth during her tenure. In 2008, EMC acquired VMware for $630 million, a deal that initially raised skepticism but later proved to be a strategic move for both companies.

Challenges Post-Acquisition:
Greene highlights the initial challenges faced by VMware post-acquisition due to a lack of understanding and interference from EMC. To address this, Greene implemented a strategy of transparency and single-threaded communication, which helped streamline operations and prevent disruptions.

VMware’s IPO and Market Success:
EMC eventually took VMware public, selling 20% of its shares and retaining the remaining 80%. The IPO was a resounding success, valuing VMware at $19 billion, with its market cap surpassing the rest of EMC’s businesses.

Campus Design Innovations at VMware:
Greene discusses the creation of VMware’s sustainable campus, showcasing her vision for transparency and collaboration. The campus featured four buildings surrounding a piazza, with transparent glass offices and central atriums. Greene’s insistence on maximizing transparency allowed for visual connectivity across the campus, creating a unique and inspiring workspace.

Recruiting in a Competitive Market:
Recruiting is challenging in today’s tight market, where individuals command high salaries. Startups have an advantage in attracting talent by offering equity and a compelling mission.

Understanding the Generational Divide:
The workforce spans three generations, each with distinct working styles and expectations. Adapting to the preferences of younger generations is a challenge for older leaders.

Communicating the Company Vision:
Initially, communicating the startup’s vision to potential hires can be difficult. As the company gains traction, explaining its mission becomes easier.

Reaching a Critical Mass:
The early stages of a startup, when hiring the first few employees, are the most challenging. VMware faced similar difficulties during the dot-com era, as traditional enterprise software was considered outdated.

Service-Centered Business Landscape:
The business world has shifted towards a service-oriented model, similar to software as a service, platforms as a service, and service as a service. Law, as a service, involves open source seed financing documents published to digitize the world.

Communication and Collaboration Trends:
Social coding platforms like GitHub enable engineers to share best practices and collaborate on code writing. Real-time communication through chat services like Slack keeps employees connected and informed. Slack and Google Docs facilitate knowledge sharing and coordination within the company.

Managing Multiple Generations in the Workplace:
Younger generations prefer daily task discussions over long-term planning, leading to a challenge in aligning with traditional planning structures. Balancing daily tasks with long-term planning requires an adaptable approach.

Distributed Workspace and Flexibility:
To facilitate collaboration, the company established two offices, one in downtown Los Altos and another in San Francisco. Employees rotate between offices on specific days, with quiet days for flexible remote work. This hybrid work model has simplified the hiring process and provided employees with location options.

Open Office Spaces:
Google redesigned its offices to create open spaces with no more than six people in one area. Each office is customized to meet the needs of different teams and employees.

Cost of Startups:
Cloud services like Amazon Web Services and Google Compute Engine have made starting a business cheaper. Free open source software eliminates the need to build everything from scratch. However, office space and salaries have become more expensive, balancing out the savings from virtual resources.

High Valuations:
Companies like WhatsApp have achieved high valuations due to their potential for monetization and user base. This can be rationalized by considering the potential revenue per user. However, inflated valuations can lead to problems when companies want to go public and face the risk of a down round.

Conclusion:
Startups today have both advantages and challenges compared to the past. While cloud resources and open source software reduce costs, expensive office space and high salaries offset these savings. Additionally, while high valuations can be achieved, companies need to be mindful of maintaining a rationale for these valuations to avoid issues when going public.

Remote Work Advantages:
Encourages collaboration and knowledge sharing among employees. Flexible work hours allow employees to manage personal responsibilities. Remote work builds trust and accountability among employees.

Importance of In-person Collaboration:
Critical for effective communication and decision-making. Fosters a sense of camaraderie, innovation, and shared purpose. In-person interactions facilitate spontaneous problem-solving and idea generation.

Pivoting and Alignment:
Regular communication and updates keep employees informed of changes and progress. Leadership plays a crucial role in explaining the rationale behind pivots. A shared sense of purpose and values helps employees understand and embrace changes.

Weekly Discipline:
Greene sends a weekly update to the company summarizing the previous week’s accomplishments and plans for the upcoming week. This practice ensures that everyone is on the same page and understands the company’s priorities. It also provides an opportunity for employees to provide feedback and input.

Interviewing as a Test:
Greene uses interviews to assess whether employees have a clear understanding of the company’s goals and priorities. This helps her identify areas where communication or alignment may need to be improved.

Understanding the Importance of Culture:
Diane Greene highlights the critical role of fostering a strong, positive culture within organizations. She emphasizes the need for inclusivity and ensuring that everyone feels a sense of purpose and belonging.

Fostering Merit-Based, Transparent Cultures:
Greene stresses the importance of creating a culture based on merit and transparency. She believes that encouraging high standards and a culture of self-accountability is essential for a company’s success.

Open Communication and Accessibility:
Greene advocates for a culture of open communication and transparency. She emphasizes the significance of allowing everyone in the company to have access to information and encourages a culture where people feel comfortable expressing their opinions and concerns.

Eliminating Politics from the Workplace:
Greene strongly believes in a politics-free environment. She views dysfunctional behavior and misaligned agendas as detrimental to a company’s success and promotes a zero-tolerance policy for politics.

Taking Breaks Between Startups:
Greene acknowledges the need to find a balance between starting companies and taking breaks. While she is currently focused on her current company, she recognizes the importance of ensuring a healthy work-life balance and avoiding overextension.

Observing Engineering Education and Innovation:
As a board member of prestigious institutions, Greene shares her insights into the exciting developments in engineering education. She highlights the increasing recognition of engineering’s role in solving global challenges and the growing interest among women in the field.

Witnessing Transformations at Intuit and Google:
Greene reflects on her privileged position as a board member at Intuit and Google. She discusses Intuit’s impressive transformation from a shrink-wrapped desktop software company to a leading software-as-a-service provider, serving as an example of a successful pivot.

Looking Back with Lessons Learned:
Diane Greene expresses her regret for not having more confidence when she started her entrepreneurial journey. She believes that having more self-assurance could have led to thinking bigger earlier, which would have been impactful.

Key Lessons:
Diane Greene shares an experience where she was windsurfing from Maui to Molokai with two friends and faced a challenging situation when the wind dropped, forcing them to spend the night on Molokai. During their return trip, Greene’s friend’s wife ripped her sail, and Greene had to make a choice between staying with them or sailing back alone. Despite the risks, Greene decided to sail back solo, encountering strong winds and using her focus and intensity to navigate through the challenging conditions. Greene describes this experience as an “entrepreneurial zen moment” that taught her the importance of rising to the occasion and using that focus and intensity in her future endeavors. She also emphasizes the difficulty of the crossing, recounting a rough sail she experienced in a larger boat from Maui to Molokai. The chapter concludes with an anecdote where a lifeguard offered Greene a ride home after witnessing her impressive sailing feat.