Chestnut Street Ventures

Smart, Simple Venture Investing

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
  • 26k 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 Shenoy

“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 Curley

“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 Miller

“As a member of the Investment Committee, I’m reviewing incredibly innovative deals and engaging with a powerful Penn Alum network. Penn entrepreneurs are transforming the world and, the Investment Committee is helping to make that happen.”

Justin Shreve

“Being included in the monthly spotlight was a wonderful opportunity for Near-Miss Management to gain exposure among a large group of Penn Alumni, who are accomplished, forward looking individuals. We have been able to share this honor with those interested in our company, which has been very valuable.  At a time when research has made it unequivocally clear that women entrepreneurs face particular difficulties in raising funds, Chestnut Street Ventures is shining a light on a progressive path forward – demonstrating their commitment and vision to advancing women.”

Ulku Oktem

Why Invest in Venture Capital?

Consistently Strong Returns

Benefits of Venture Investing

Your chance to invest like an insider in game-changing innovation.

Participate in huge value creation pre-IPO and pre-acquisition.

Higher quality investment opportunities than angel investing or going it alone.

VC is not tied to the stock market, offering diversification during a downturn.

Invest directly in your interests: seed-stage startups, social impact, women entrepreneurs and more.


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
  • DFJ Capital
  • Drive Capital
  • 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

The leading venture capital firms are provided for illustrative purposes only; there is no guarantee that any fund will invest alongside of any other venture capital firm.

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 alumni 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 Snyder

“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 Shreve

“As an IC member, I have participated in a number of in-depth examinations of potential investments, and have been impressed by the breath of knowledge and experience that Gail and Ven bring to CSV. The fund provides individual investors an uncomplicated entry into the dynamic venture capital space, while supporting fellow Penn alumni.”

Rebecca Singer

“I met Gail at a pitch night at the Penn Club in New York. She had actionable feedback to advance the company’s goals. I mentioned I was looking for an advisor with a specific skillset and she kindly offered to include our ask in the CSV newsletter that was going out a week later. She made it happen and a few days later we had connected to a fantastic person that we’ll continue to collaborate with and who we believe can help us move the needle in some of our forthcoming goals. I’m thankful for CSV’s commitment to help the Penn entrepreneurial community.”

Adriana Vazquez