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Zach Holman

Zach Holman

Startup founder, angel investor, developer, and sports enthusiast

holman
San Francisco, California
Joined March 2025

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Summary

Zach Holman is a serial entrepreneur and startup founder, currently building Signed and Calendearing. His ventures often reflect his passion for developer tools and sports, evidenced by his investments through Tifo and co-founding WorkOn, a sports-tech startup. zachholman+3
A foundational engineer at GitHub, Zach Holman was instrumental in its early growth from 9 to 250 employees (2010-2015). He has extensively written and spoken about GitHub's culture and operational philosophies, including his experience being 'fired' and insights into scaling software teams. zachholman+3
Beyond building companies, Zach Holman is an active angel investor through his fund Tifo, focusing on early-stage developer tools and sports companies. He shares his investment philosophy, including practical advice on tender offers and understanding startup finances, noting his focus on revenue-generating and B2B SaaS businesses. tifo+2
Deeply engaged in the soccer community, Zach Holman is a minority owner of Oakland Roots Sports Club and Oakland Soul Sports Club, and serves as the Director of Technology for The American Outlaws Inc., the largest US Soccer supporters' group. He played soccer and actively supports its growth, co-founding the sports-tech startup WorkOn. zachholman+2
Zach Holman is a vocal advocate for work-life balance in the demanding startup world, reflecting on his own burnout experience at GitHub. He promotes a philosophy of prioritizing happiness and productivity, embracing remote work, and cutting loose when needed to maintain long-term engagement and creativity. balancethegrind
A prolific writer and speaker, Zach Holman maintains a personal blog where he shares insights on startups, software development, work culture, and his personal experiences. His posts range from technical topics like 'How GitHub Works' to personal reflections on career changes and his involvement in sports. zachholman+2

Work

Education

Projects

Writing

Taking Money off the Table

October 30, 2025

A blog post offering advice on tender offers and managing equity gains for startup employees, advocating for taking profits to de-risk and avoid burnout.

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Shipping Calendearing

September 29, 2025

A blog post discussing the development and philosophy behind his Calendearing product, emphasizing 'Do One Thing Well' and his return to building personal side projects.

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From Cold DM to Owning a Soccer Club

January 30, 2025

A detailed blog post on his personal journey to becoming a minority owner of Oakland Roots Sports Club, discussing the differences between sports ownership and tech startups, and the financial transparency of his investments.

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Fired

February 1, 2015

A blog post reflecting on his departure from GitHub in 2015, discussing the taboo nature of being fired, and sharing personal insights into career transitions and resilience.

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How GitHub Works

August 15, 2011

A three-part series from 2011 detailing how GitHub operated in its early days, covering topics like 'Hours are Bullshit,' 'Be Asynchronous,' and 'Creativity is Important,' and offering insights into running effective technical companies.

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Graduated with a Major in Startups

February 7, 2011

A blog post reflecting on his education at Carnegie Mellon and the disconnect between traditional university education and the practical needs of the startup world, advocating for more hands-on, project-based learning.

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Losing Money is the Point

A blog post explaining that for many growing companies, 'losing money' is often a strategic investment for future larger returns, particularly in venture-backed firms and sports organizations.

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Hobbies

A lifelong soccer fan, he played in high school, continues to play, and is deeply involved with the American Outlaws, a major US Soccer supporters' group. zachholman