Kelsey Hightower - On retiring as Distinguished Engineer from Google at 42 (Part 2)
Aug 3, 2023
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Former Google Distinguished Engineer, Kelsey Hightower, discusses financial planning for early retirement at 42, advising startups, turning down Microsoft, and meeting Satya Nadella. He reflects on valuing time, shifting priorities, overcoming ego, and career impact.
Early retirement at 42 enabled by strategic financial planning and turning down lucrative job offers.
Questioning traditional notions of meaning and purpose in retirement; emphasizes self-discovery in intentional living.
Navigating intentional living post-retirement through personal growth, health, finance, and experiential travel choices.
Mentoring startups with ethical boundaries, focusing on product development, pricing strategies, and impactful storytelling.
Deep dives
Financial Planning for Early Retirement
Early retirement at 42 was enabled by strategic financial planning for Kao Si. He walked away from a substantial offer from Microsoft to retire. This decision was driven by his desire for freedom from artificial deadlines and the corporate grind. By carefully managing his finances and investments, he reached a point where he could retire and focus on personal priorities.
Reevaluating Meaning and Purpose
Kao Si questions traditional ideas of meaning and purpose in retirement. He emphasizes unlearning the conventional need for meaning and delves into the process of discovery in a world structured around societal norms. With a focus on self-accountability and intentional living, he explores finding value in personal productivity and defining a new path beyond traditional success measures.
Personal Growth and Intentional Living
Post-retirement, Kao Si navigates intentional living by focusing on personal growth and well-being. He engages in self-discovery and plans meticulously for various aspects of his life, including health metrics, financial strategies, and experiential travel. By prioritizing purposeful actions and sustainable habits, he aims to cultivate a fulfilling post-career lifestyle.
Startup Advising and Mentorship Role
Kao Si excels in his role as a part-time PM and mentor for startups. He leverages his expertise to guide founders on product development, pricing strategies, and effective storytelling. Through coaching and support, he empowers founders to communicate their vision authentically, engage with stakeholders, and navigate challenges to drive business growth and success.
Startup Advising and Equity Impact
Engaging in startup advising while maintaining a full-time job involves establishing ethical boundaries, ensuring non-conflict with the employer's activities. By requesting a monthly retainer and equity from startups, tangible impact and value exchange can be established. This approach was illustrated in a successful partnership where advising led to pivotal website changes and ultimately influenced acquisition decisions.
Negotiating Retainers and Equity in Startup Engagements
Determining retainer and equity terms for startup engagements is linked to personal expenses and future investment potentials. In the process, setting a retainer aligned with living costs and negotiating fair equity stakes, considering vesting cycles and exercise windows, can create mutually beneficial agreements. This approach seeks to balance immediate financial needs with long-term investment aims.
Philosophy of Saying Yes to Opportunities and Collaborations
Approaching career decisions and collaborative opportunities is rooted in a philosophy of impactful engagements. By assessing the potential impact of interactions, whether advising startups, sharing knowledge on podcasts, or engaging in new ventures, a focus on genuine value exchange and meaningful contributions guides decision-making. This approach prioritizes authenticity, impact, and the potential to positively influence others' trajectories.
Kelsey Hightower was a Distinguished Engineer at Google, where he worked on Google Cloud Platform. In this second part of the conversation, we focus on Kelsey’s retirement - the financial planning that enabled him to retire at 42, how he got started advising startups and his perspectives on compensation, turning down a substantial offer from Microsoft and meeting Satya Nadella in person. And, of course, plans for the future.
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