Chestnut Street Ventures

Smart, Simple Venture Investing for Penn Alums

What Is Chestnut Street Ventures?


The smartest, simplest way for Penn alums to add venture capital to their portfolio. We are also…

  • A full-time alumni investment team
  • An Investment Committee with over 250 years of investing experience
  • 15K+ alumni followers
  • The only fund of its kind for Penn alumni
  • Private, for-profit, and not officially sanctioned by the university


Follow the Fund

“The most valuable gift that an Investor can offer an entrepreneur is a transparent, predictable and efficient path to an investment decision. We give Chestnut Street Ventures high marks for their commitment to an investment consideration and due diligence process that was as efficient as we’ve seen in our multiple rounds of financing. It’s an exceptional way to start a long term relationship and speaks volumes to their empathy and understanding of the needs of a startup team.”

Neal ShenoyCEO @ Begin

“As an investor in Chestnut Street Ventures, I have had the opportunity to participate in some exciting early stage companies led by Penn Alums. Co-investors have included a group of elite Venture Capital Funds that I would not have had access to as an individual investor.”

Carol CurleyCFA & Investor in Chestnut Street Ventures

“Gail and her team at Chestnut Street Ventures are the perfect vc partner – super smart, incredibly well-connected and lightning fast responsive.  Chestnut Street leverages the Penn network in deep and profound ways to bring value to investors and portfolio companies alike.   And the connection to the broader universe of other Alumni Ventures Group funds makes the network even more powerful.”

Dean MillerPresident of PACT

Why Invest in Venture Capital?

VC Outperforms the S&P

Key Takeaways

VC has consistently outperformed the S&P

VC can do well, even when other asset classes don’t

Sophisticated investors put 5-15% of their portfolios in VC

Investment Strategy

Smart, Simple Venture Investing

Diversified Venture Portfolio

15 – 30 investments per fund, diversified by stage, sector, and geography

Co-Invest with Strong Lead Investors

We only invest when a strong, established investor (often a fellow alum) is leading the financing

Deal Access via Alumni Connections

Entrepreneurial teams desire our investment because we are a meaningful check, low friction, and have a large rolodex

Co-Invest Alongside Top Venture Firms

Invest In Deals Most Individuals Never Know About or Get Access To

  • 3M New Ventures
  • 500 Startups
  • Accel Partners
  • Accomplice
  • Alsop Louie Partners
  • Andreessen Horowitz
  • Arena Ventures
  • Aspect Venture Partners
  • Atlas Ventures
  • Benchmark
  • Bessemer Venture Partners
  • Bezos Expeditions
  • BlackRock
  • Blockchain Capital
  • Borealis Ventures
  • Comcast Ventures
  • CrunchFund
  • Drive Capital Jurvetson (DFJ Capital)
  • Draper Fisher
  • Flybridge Capital
  • Elephant Partners
  • Founder Collective
  • Foundry Group
  • F-Prime Capital (Fidelity)
  • General Catalyst Partners
  • Golden Seeds
  • Goldman Sachs Ventures
  • Google Ventures
  • Greylock Partners
  • Highland Capital
  • Javelin Partners
  • Khosla Ventures
  • Kleiner Perkins Caufield & Byers
  • Lightspeed Venture Partners
  • Link Ventures
  • Maveron
  • Menlo Ventures
  • ML Capital
  • New Enterprise Associates (NEA)
  • Nokia Growth Partners
  • Norwest Venture Partners
  • NXT Ventures
  • Obvious Ventures
  • OrbiMed
  • Pelion Venture Partners
  • Relay Ventures
  • Resolute Ventures
  • Sequoia Capital
  • Summit Partners
  • Space Angels
  • SV Angel
  • Thiel Capital
  • Venrock
  • Winklevoss Capital
  • Y Combinator

How does Chestnut Street assemble a great portfolio for me?

  • Full-time investment team wakes up every morning dedicated to delivering a diverse portfolio to investors
  • An Investment Committee with over 250 years of investing experience
  • We use our Penn and broader Alumni Ventures Group network to access deals that simply are not available to most individuals
  • We only invest in deals with a strong lead investor with sector expertise, combining their due diligence with our own


See The Chestnut Street Portfolio

“Chestnut Street Ventures has quickly come on the scene in Philly to become a catalyst for early stage companies with their unique access to funding and expertise through the Penn alumni network and relationships with sister funds connected with other top schools. They have been a great partner to Safeguard and our partner companies including Cloudmine and Cosy where they have been active in bringing timely capital and market support to help these companies reach the next stage of growth.”

Scott SnyderPhD & CTO, Chestnut Street Ventures Ambassador

“I feel I have joined a truly committed partner in Chestnut Street Ventures that will offer terrific investment opportunities as well as valuable connections to new companies and other funds. I am confidently excited about the insights and wisdom that Chestnut Street Ventures brings to the table, along with Chestnut’s upside potential for future growth!”

Jim ShreveChestnut Street Ventures Investor