handshake
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Garrett Lord and the geography of a first chance
A Michigan Tech student found his way into Palantir and wondered why the route was so hard to see. Garrett Lord built Handshake around that question. Now he is taking its network into the AI economy.
Darshdeep Hora and the Last 22 Percent
The engineer's revealing work is not the first 80 percent an AI can do. It is the stubborn remainder where judgment, trust, and one wrong customer name can undo everything.
Aniruddha Pai Keeps Building at the Moment a Student Becomes a User
From a Reddit bot for bewildered students to a catalog of prompt patterns for large language models, Pai's public work reveals a practical instinct: make complicated systems easier to ask, search, and use.
Handshake
Handshake is a San Francisco company that began as the career network for Gen Z, connecting tens of millions of students and recent grads with employers and university career centers. Built by three Michigan Tech computer science students to give kids from non-elite schools a fair shot at good jobs, it grew into the dominant early-career recruiting platform. In January 2025 it launched Handshake AI, turning its network of students, PhDs and domain experts into a human data-labeling marketplace that supplies high-quality training data to frontier AI labs - a pivot that has grown into a roughly $1B annualized gross revenue business.
Ashish Desai
Ashish Desai is the CEO of Monograph, the San Francisco software company that helps architecture and engineering firms run the business side of the practice - budgets, staffing, forecasting and billing. An electrical engineer turned product leader, he scaled product at 99designs, Handshake and Shutterfly before joining Monograph as Chief Product Officer in July 2023 and stepping up to CEO in 2026, succeeding co-founder Robert Yuen. His pitch is simple: software that understands how architects actually work, so firms can spend more time on design and less time guessing at their numbers.
Yang Zhao
Yang Zhao is the Chief Business Officer of Handshake AI, where he runs business and operations for a fast-scaling human-data business serving frontier AI labs. He spent four years at Scale AI as Head of Product Deployment and Operations before joining Handshake, and earlier led growth and strategy at the consumer-rentals company Zumper. He pitches Handshake's edge not as tooling but as raw access to the largest expert network in the US.
Jennifer Carolan
Jennifer Carolan is co-founder and general partner at Reach Capital, a San Francisco-based venture capital firm she helped build from the ground up to become the most active dedicated edtech investor in the US. A former K-12 history teacher in Chicago who spent nine years learning venture capital at NewSchools Venture Fund, she has since deployed four funds totaling over $500M across 100+ education technology companies. Her portfolio has produced five unicorns including ClassDojo and Handshake, and she continues to teach at Stanford while backing the entrepreneurs she believes are removing the obstacles standing between people and opportunity.