Chestnut Street Ventures

Smart, Simple Venture Portfolios with Community

What Is Chestnut Street Ventures?


A smart, simple way for Penn alums and friends of the community to add venture capital to their portfolio. We are also…

  • A full-time alumni investment team
  • An Investment Committee with broad professional, investing, and entrepreneurial experience
  • 31k subscribers and community members
  • Private, for-profit, and not officially sanctioned by the university


Follow the Fund

Meet the MP: Brian Keil


“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 You May Want to Add Venture Capital to Your Portfolio

  1. VC returns have been strong over many periods1
  2. VC returns are largely uncorrelated with other asset classes2
  3. A great way to be an impact investor

1. Cambridge Associates, Venture Capital Benchmarks
2. Top Tier, The Inverse Correlation Between Venture and Public Markets

Investment Strategy

Smart, Simple Venture Investing

Diversified Venture Portfolio

~20 – 30 deals per fund, diversified by stage, sector, and geography

Co-Invest with Established Lead Investors

We exclusively invest alongside established VC investors

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 Established 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

AVG has invested alongside the firms listed above, but they are listed for illustrative purposes only. There is no guarantee that a particular fund or deal will invest alongside one of the firms listed above.

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 broad professional, investing, and entrepreneurial 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 an established lead investor, often 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

The AVG Syndicate


Syndications are opportunities to invest in single asset funds that give you more exposure to a specific company you may be excited about and in which one or more of our AVG Funds will also be investing.


How it works:

  • Investors can opt into Syndications as they wish.
  • Opportunities are sourced by our 40+ full-time investment professionals and our Office of Investments.
  • All opportunities have passed our diligence process and are being invested in by one or more of our funds.
  • Minimums are typically $25K per opportunity, or $10K for opportunities offered through your Venture Club(s).
  • Typically, only about 5-10% of our investments are offered to our Syndicate - normally when we are able to acquire a larger investment allocation.


Rigetti is a full-stack quantum computing start-up. It focuses on designing and manufacturing superconducting quantum integrated circuits, building software to enable quantum computing, and integrating its systems into a cloud infrastructure.

Co-investors include Andreessen Horowitz, Data Collective, and Y Combinator.



Tembo Health provides a telemedicine platform connecting nursing home residents with specialized care providers through an intuitive video chat platform. This enables patients to access convenient, high-value specialty medical care at a safe distance.

Co-investors include Bloomberg Beta Founder and General Partner Karen Klein.