Caleb Gates

Hey Hey. I'm here to share my personal experience bootstrapping startups in San Francisco, employment at VC funded startups, and most recently supporting operations and fundraising initiatives through my role of Chief of Staff at a 100 person company that is scaling back during this bear market. At the COS Summit in NYC I learned about the variety of roles and responsibilities across all types of COS positions. I'm excited to expand my knowledge in areas outside my expertise like Finance, Legal, Hiring, etc as well as continue to compare and contrast best practices. Fun facts? lol. I'm an Identical twin working as COS to my brother and I have definitely used that to my advantage by impersonating him at business events. How do you go to a concert with a prospective investment firm, stay up to 3am, and then be on investor calls at 8am the next day... you send your identical twin. I love my brother, however, I'm on the lookout for my next thing as a way to regain part of my own identity. You can find me biking, climbing, exploring, and scheming in the best part of NYC (Williamsburg). My latest interest is thrifting as it feeds my love of story telling. I recently discovered that fashion provides a new depth of expression. I'm leaning into crafting new narratives.

Top Areas of Focus

Business Operations
Fundraising and Investor Relations
Growth/Sales & Marketing
Product Development
Strategic Partnerships / BD Strategy & Planning
Strategy & Planning
Fundraising & Investor Relations
Strategic Partnerships / BD

CoS Start Date

Sep 1, 2022

Current Industry

Company Size




Previous Experience

Pro Tip

1. Assistants are told what to do, Leaders tell their others (boss included) what they're going to do. 2. "Why" is the best question. "What" is for engineers and gets into facts. "How" simply focuses on execution. But "Why", Why gets to the core motivation behind everything and unlocks thoughts that cannot be expressed in terms of "What" or "How". Sure they say "Start with the why", but honestly every question should be phrased as a why. 3. Mindset: Learn how to do something new, document it, then hire your replacement.


A technical perspective. The founders perspective. Most recently I spent 1 year pursuing every fundraising avenue so I can certainly dive deep in that discussion. Cold outreach strategies for mentorship & friendships.


Best practices. Accountability. Maybe even friends. I truly feel that I don't know what I don't know. My first goal is observe everything.