Deepak Gupta

He/Him

Chicago Booth
University of California, Berkeley
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About

Having spent 15+ years as a venture capitalist, 4-time startup operator, fractional CFO, and career advisor, Deepak knows firsthand how opaque, intimidating, and fragmented Silicon Valley and high-growth ecosystems can be. When he was starting out, having the right mentor made all the difference. Today, he brings that firsthand experience to helping others navigate these environments with greater clarity and confidence. Deepak’s investment portfolio includes category-defining companies such as OpenAI, Ayar Labs, Coreshell, Trulia, Ancestry, and Box. Before transitioning to venture, he spent over a decade in the medical startup space, serving in both entrepreneurial and management capacities. His tenure in operations was marked by two successful exits: Cepheid (NASDAQ: CPHD) and NeuroPace (NASDAQ: NPCE). He holds an MBA from the University of Chicago Booth School of Business, an M.S. in Biomedical Engineering from Virginia Commonwealth University, and a B.S. in Mechanical Engineering from Virginia Tech.

Why do I coach?

Coaching matters to me because I believe nobody should have to navigate complex career inflection points alone. Over the past 11+ years advising hundreds of MBA students, founders, and professionals, my goal has been to demystify the hidden rules of Silicon Valley and empower clients to achieve life-changing career outcomes across four key areas: 1) Salary & Equity Negotiation: Demystifying complex equity offers, cap tables, and valuation models so you leave no money on the table. 2) Landing Roles at Top-Tier Venture-Backed Startups: Position yourself effectively, target the right stage/vertical, and secure direct introductions to high-growth leadership teams. 3) Building Companies (0 to 1): Guiding founders through early-stage validation, product-market fit, and pitch preparation to become fundraising-ready. 4) Breaking into Venture Capital: Unlike standard hiring, VC recruiting is heavily relationship-driven. I help clients differentiate GE and early stage VC, build targeted fund pipelines, and navigate opaque interview processes. Nothing is more rewarding to me than seeing a client unlock their true potential, land their dream offer, or launch a venture with confidence.

Work Experience

Managing Director

Blue Bear Ventures

2017 - 2023

UC Berkeley Shared Carry Fund

Senior Associate Director & Industry Professional, Startups & VC

University of California, Berkeley

2014 - Present

Fractional CFO

Various startups

2013 - 2023

Named one of the Top 20 Fractional CFOs for driving capital efficiency and financial clarity across diverse startups, providing executive-level financial leadership when full-time roles weren’t yet feasible. (https://kruzeconsulting.com/fractional-cfos/) Supported CFOs across Bessemer Venture Partners' portfolio as part of the Operating Group since 2015, leveraging financial and operational expertise to help startups scale effectively amid early-stage complexity. Built and implemented financial and organizational structures that empowered founders to focus on product and growth, addressing the common startup challenge of scaling without operational overload. Established financial discipline and investment readiness processes to optimize resource allocation and drive valuation growth, ensuring startups could confidently raise and deploy capital. Led board meeting preparation and participation by shaping clear, data-driven narratives that aligned investors and executives, strengthening strategic direction and trust at key inflection points.

Vice President

Propel Venture Partners

2012 - 2013

Developed a thesis around emerging technologies such as Big Data, Security & Fraud, and Mobile Payments, leading to strategic investments in Radius and SaveUp by leveraging market research and founder diligence, driving exposure to high-growth sectors addressing trust, access, and data transparency in digital finance.

Investment Professional

Hercules Capital

2008 - 2012

Analyzed financials of 500+ companies and built financial models to support investment decisions, contributing to key deals (Box, Trulia, Ancestry, Wageworks), while collaborating with the Group Head of Energy and Climate Tech to grow the firm’s climate tech practice from inception to $500M AUM, driving capital toward scalable environmental solutions.