CANONICAL LABS · LOOKALIKE FINDER

Nikhil Raman

Investor · Union Square Ventures · New York, New York, United States

Nikhil Raman

Investor · Union Square Ventures · New York, New York, United States

Career arc

Nikhil Raman transitioned from a software engineering background at Google, where he developed mobile ad products, to a founding engineer role at the fintech startup Daffy. He then moved into venture capital, joining Union Square Ventures as an Investor in January 2023, where he leverages his technical and operational experience to identify and support founders building innovative solutions, particularly in emerging technologies like AI and decentralized systems.

Defining traits

Deep technical builder (Google SWE, founding engineer) who crossed into venture capital, maintaining hands-on engineering sensibility while evaluating marketsBuilding custom software and AI agents to reimagine what an AI-native VC firm looks like—applying engineering to the investment process itselfBridges the language gap between engineers building products and investors evaluating markets; evaluates implementation feasibility alongside market potentialSpecializes in the liminal space between 'interesting experiment' and 'potential unicorn'—comfortable with emerging, unproven categoriesFounding engineer at Daffy fintech startup, bringing zero-to-one product building experience to investment evaluationInvests across generative AI, decentralized systems (NFTs), climate tech—drawn to technological paradigm shifts rather than established categoriesSpans fintech, programmatic ads, developer tools, AI—technical breadth with product development depth across domains

People with similar career DNA

Shilpi Nayak

Founder & Managing Partner · 434 VC

Product and engineering leader with 15+ years building large-scale systems at Google, Akamai, and Intel who transitioned to founding 434 VC. Invests in AI, fintech, private markets, and vertical AI while maintaining deep product and engineering expertise.

Why: Nearly identical arc: Google engineer to VC founder, investing in AI and fintech with hands-on product/engineering background. Strong match on technical depth and emerging tech focus. Differs in having longer tenure at Google and broader enterprise systems experience.

Nikhil Kapur

Investor

Former Microsoft engineer building Excel who transitioned to early-stage investing in AI infrastructure, DevTools, and open source. 2x operator, 1x founder making day-zero investments in pre-seed infrastructure startups.

Why: Similar trajectory from big tech engineering (MSFT vs Google) to early-stage investing with operator/founder experience. Strong focus on developer tools and AI infrastructure. Differs in specializing more narrowly on infra/devtools rather than broader emerging tech categories.

Haomiao Huang

Founding Partner · Matter Venture Partners

Engineer turned startup founder turned venture investor with passion for bringing digital innovation into physical economy businesses. Focuses on robotics, AI, and software transforming logistics, manufacturing, retail, and mobility.

Why: Classic engineer→founder→investor path with founding partner role. Strong on translating between technical and market perspectives. Differs in focusing on physical economy/robotics rather than pure software, and less emphasis on building investment infrastructure itself.

Bogdan Cristei

Founder · OPTIM · SHACK15 · OMNI

Engineer turned investor-operator investing and building in real-world AI, robotics, automation, and industrial systems. Backed 35 companies that raised $1B+ while maintaining operator role across multiple ventures.

Why: Engineer-to-investor with strong operator DNA and emerging tech focus (AI, robotics). Maintains hands-on building role. Differs in focusing on industrial/physical systems rather than software/fintech, and less emphasis on developer tools or investment process innovation.

Clement Pang

Entrepreneur in Residence · Sutter Hill Ventures

20+ years building data infrastructure at scale from Google to founding Wavefront (acquired by VMware for $400M) to investing in technical founders. Now EIR at Sutter Hill Ventures exploring next venture.

Why: Google engineer to successful founder ($400M exit) to investor—strong parallel path. Deep data infrastructure expertise and technical founder evaluation skills. Differs in being at established VC firm rather than building new investment model, and currently in EIR exploration phase.

Deedy Das

Partner · Menlo Ventures

Technical VC at Menlo Ventures bringing engineering expertise to AI investments. Known for strategic insights combining technical depth with investment acumen, transforming how AI companies are evaluated.

Why: Technical VC specializing in AI with strong engineering background and translator skills. Excellent at bridging technical and investment perspectives. Differs in lacking founding operator experience and working within established VC rather than building new investment infrastructure.

Liron Langer

Founder & MD · Meta3Ventures

Serial entrepreneur progressing from CTO to CEO to VC, with 30+ companies and multiple exits. Former CIO of Nielsen Innovate Fund, now building AI-native ventures as venture builder and operator-investor.

Why: CTO→CEO→VC path with strong focus on building AI-native ventures and investment infrastructure. Venture builder model aligns with reimagining VC. Differs in broader enterprise focus and less emphasis on specific emerging tech categories like crypto/climate.

Anupam Rastogi

Managing Partner · Emergent Ventures

Early-stage VC partnering with ambitious founders building enterprise AI, infrastructure, and deep-tech companies. Works closely with founders through highest-leverage moments: finding PMF, designing GTM, and scaling teams.

Why: Early-stage investor in AI and deep tech with strong focus on ambiguity navigation and emerging categories. Good translator between technical and business. Differs in less clear engineering background and founding operator experience; more traditional VC partner role.

Borys Musielak

Investor · SMOK Ventures

Engineer turned founder turned investor, building communities from Linux/open source through startup founders to angel investors in Central and Eastern Europe. Actively deploying capital into pre-seed and seed stage startups.

Why: Classic engineer→founder→investor trajectory with community-building focus. Strong on early-stage and technical evaluation. Differs in geographic focus (CEE vs US), less emphasis on specific emerging tech theses, and more traditional venture model.

Latest activity

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LinkedIn · Nikhil Raman

LinkedIn · Nikhil Kapur

LinkedIn · Nikhil Raman