Dylan Kaplan

Dylan Kaplan

Early-Stage Venture Capitalist | Startup Mentor at MassChallenge | Tony Award-Winning Broadway Producer

I specialize in

Fundraising 101
VC & Angel Advice
Idea to Launch
Fundraising strategy
Story & narrative
Pitch deck
Product validation

Tony-winning producer turned VC funding deep tech startups

Background & Highlights

VC Scout

Alumni Ventures

2025 – Present

Alumni Ventures

Startup Mentor

18X Elite Impact

2025 – Present

Startup Mentor

MassChallenge Israel

2024 – Present

About me

Early-Stage Venture Capitalist | Startup Mentor at MassChallenge | Tony Award-Winning Broadway Producer I’ve built my career on one core principle: relationships drive results. My journey began on Broadway, where I produced award-winning shows alongside world-class creative teams, investors, and global brands. That chapter earned me a Tony Award, three additional Tony nominations, an Emmy nomination, and a Grammy nomination — but more importantly, it taught me the power of uniting diverse talents around a shared vision. After graduating from NYU’s Stern School of Business MBA program, I pivoted into the startup ecosystem. I worked for both semiconductor and consumer startups before joining an early-stage deep tech fund, where I focused on advanced automation, robotics, and semiconductor investments. Today, I’m a Venture Capitalist at Alumni Ventures supporting startups worldwide across all stages. I’m particularly passionate about helping international startups break into the US market. As a mentor with MassChallenge, I guide founders through critical early-stage hurdles — from refining business models to navigating fundraising and growing their visions. My mission is to connect corporations, startups, and venture capitalists in ways that accelerate innovation and unlock lasting impact.

You'll get advice on

  • The Art of Storytelling
  • Strategic Networking To Build Meaningful Influence
  • Mastering Fundraising: Pitch Decks and VC Mindset
  • Own Your Audience: Customer Retention Strategy
  • Business Model Makeover: Validate, Pivot, and Grow

Real feedback from real sessions

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