Deepak Gupta
Startup careers and founder coach with 15+ years in venture capital
| Hourly rate range | $90 to $185 an hour |
|---|---|
| Focus areas | |
| Works with | Founders and business owners, Professionals and Students |
| Also coaches | Business coach and Executive coach |
| Credentials | MBA, University of Chicago Booth School of Business; M.S. in Biomedical Engineering, Virginia Commonwealth University; B.S. in Mechanical Engineering, Virginia Tech |
| Experience | 11 years coaching |
Deepak Gupta is a startup careers coach who helps MBA students, founders and professionals. He has spent more than 15 years as a venture capitalist and worked as a four-time startup operator through two IPOs. He also serves as a fractional CFO. His investments include OpenAI, Ayar Labs, Coreshell, Trulia, Ancestry and Box. He has advised hundreds of clients over the past 11 years on pay, startup roles, company building and venture capital careers.
What Deepak helps with
Deepak works on career moves inside the startup and venture world. He also guides early-stage founders toward fundraising.
- Understanding equity offers, cap tables and valuation models
- Negotiating salary and equity
- Landing roles at top venture-backed startups
- Choosing the right startup stage and vertical
- Validating an early-stage company idea
- Reaching product-market fit
- Preparing a pitch to raise money
- Breaking into venture capital
Who Deepak works with
Deepak advises MBA students, founders and professionals. His clients face career turning points in Silicon Valley and high-growth startup settings. Some want a startup job, some want to build a company from zero, and some want to enter venture capital.
Background and qualifications
Deepak spent over a decade in the medical startup space in both entrepreneurial and management roles. His operations work led to two exits: Cepheid (NASDAQ: CPHD) and NeuroPace (NASDAQ: NPCE). He then moved into venture capital and has spent more than 15 years as an investor. He has held a Managing Director role at Blue Bear Ventures and been a seed investor in several companies. He is also a four-time startup operator and a fractional CFO. He holds an MBA from Chicago Booth, an M.S. in Biomedical Engineering and a B.S. in Mechanical Engineering.
Deepak Gupta pricing
Programs and services
- One-on-one coaching
- Salary and equity negotiation
- Startup job search support
- Founder coaching from idea to fundraising
- Venture capital recruiting prep
Deepak Gupta reviews
Deepak Gupta has a 5.0 out of 5 rating from 6 reviews on Leland, as of September 2026.
The CoachVouch take
Deepak is a working venture investor and former startup operator with two exits, so he coaches from inside the industry.
Best for MBA students, founders and professionals who want a startup role, a stronger equity offer or a way into venture capital.
Common questions
How much does Deepak Gupta charge?
Coaching with Deepak runs $90 to $185 an hour. Request an intro for an exact quote.
What does Deepak Gupta help with?
Deepak Gupta helps with understanding equity offers, cap tables and valuation models, negotiating salary and equity, landing roles at top venture-backed startups and choosing the right startup stage and vertical.
Does Deepak Gupta have reviews?
Deepak Gupta has a 5.0 out of 5 rating from 6 reviews on Leland, as of September 2026.
Is Deepak Gupta certified?
Deepak Gupta lists: MBA, University of Chicago Booth School of Business; M.S. in Biomedical Engineering, Virginia Commonwealth University; B.S. in Mechanical Engineering, Virginia Tech.
Does Deepak Gupta help people break into venture capital?
Yes. He helps clients tell apart growth equity and early stage VC, build target fund lists and handle VC interview processes.
Does Deepak Gupta coach startup founders?
Yes. He guides founders through early validation, product-market fit and pitch prep so they are ready to fundraise.
How do I contact Deepak Gupta?
Request an intro on this page. It's free, and we'll connect you with Deepak and, if you want, 2 or 3 similar coaches to compare.
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Last updated September 2026. Request a correction.