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Chestnut Street Ventures’ Fund and Syndicate

Venture Investing With Fellow Penn Alums

What It Is

A private investing community for Penn alums, featuring both a diversified venture fund and deal-by-deal syndications. Chestnut Street invests in cutting-edge ventures, co-invested alongside leading venture capital firms. Members have access to venture deals with low minimums and due diligence sharing on each deal. Chestnut Street is built on the premise that we do better together.

Who It Is For

Accredited Penn alumni who want strategic exposure to venture capital. Ideal if you believe in innovation, technology and entrepreneurship—and you value investing with fellow alums (alongside leading venture capitalists).

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It’s All About Access to Life-Changing Deals

You Get Access to Deals Led by Top VC Firms: Quality, Quantity, Diversification.

Designed for Retail Investors

Build a venture portfolio to fit your goals. Alumni Ventures invests across stages and geographies, co-investing with elite firms.

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    Pre-seed to Later-Stage

    We invest at a variety of stages, always evaluating upside vs. price.
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    Diverse Geographies + Leads

    We look for great deals everywhere and co-invest alongside a wide variety of strong lead VC firms.
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    Due Diligence by Alumni Ventures

    America's Largest Venture Firm for Individuals and an “America’s Top 20 Venture Capital Firm of 2025” (Time ’25).
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    You Decide

    Invest in funds for maximum coverage. Invest deal-by-deal for maximum exposure.

Co-Invest With Elite VCs

The best ventures have their pick of lead investors — it only makes sense to invest alongside them. These firms have co-invested in many deals with Alumni Ventures:

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    Andreessen Horowitz

    51 investments with AV
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    Sequoia

    25 investments with AV
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    Bessemer Venture Partners

    22 investments with AV
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    Y Combinator

    56 investments with AV
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    Founders Fund

    28 investments with AV
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    Kleiner Perkins

    23 investments with AV
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    Khosla Ventures

    56 investments with AV

Two Ways to Participate

How You Want to Partner With Us Is Up to You.

Our Fund

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    Simplest Way to a Startup Portfolio

    An annual fund of 20-30 high-quality diversified investments — offering you the most efficient way to build a large portfolio.
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    Diversification Across Many Dimensions

    Diversification across sector, stage, geography, and lead investor — mitigating risk while capturing the potential upside of breakthrough innovations.
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    Leave It up to Us

    Our team gets up every day to strategically deploy your capital over ~12-18 months, reserving ~20% to pursue follow-on opportunities in the most promising portfolio investments.

Our Syndicate

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    Real-Time Deal Flow

    You see deals as we see them - about a deal a month (it ebbs and flows). Deals move fast and sometimes fill up.
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    Access to Our Diligence Portal

    Access due diligence and view "Why We Are Investing" video briefs.
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    Hands-On Capital Management

    You decide which investment opportunities are right for you and how much to invest.

Timeline for the Annual Chestnut Street  Fund

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About Alumni Ventures

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    Top-Tier and Battle Tested

    PitchBook names AV the #1 most active VC in the U.S. (’22–’23) and CB Insights slots us in its 2024 Top 20; our 2016-20 funds sit in Cambridge Associates’ top-quartile performance ranks.
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    Diversification From Day One

    $1.4B+ deployed across 1,400+ venture-backed companies, with ~250-300 new investments added annually; diversification spreads risk and upside across stage, sector, and geography.
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    Co-Investing With the Best

    AV routinely co-invests alongside leading venture firms such as Andreessen Horowitz, Sequoia, and NEA, giving you the benefits of their negotiated terms and their support to portco companies.
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    Network You Can Lean On

    11,000 accredited investors and an 850,000-strong alumni & entrepreneur community create proprietary deal flow, talent pipelines, and follow-on capital impossible to assemble alone.
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    Dedicated, Nationwide Team

    40 full-time venture professionals spread across five U.S. offices source 50-75 fresh opportunities each quarter, vet them rigorously, and present only the deals we commit to doing for our funds.

See video policy below.

Meet the Team

Your classmates and community members who wake up everyday to assemble a great venture portfolio.

  • Investment Team
  • Investment Committee
  • Venture Fellows
  • AV Support Team

Chestnut Street Ventures Content & News

Content at the intersection of entrepreneurship, venture capital, and our shared alma mater.

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The Chestnut Street Portfolio

We invest alongside other established venture firms in a broad range of ventures to help build you a diversified venture portfolio.

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Join Us (For Free)

Start Investing With the Penn Alumni Community Today.

Every new member who completes the sign-up process in October will receive a $100 credit
to the AV Swag Store and be entered to win $800 worth of high-quality AV apparel.
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    Easy Sign-Up

    Enroll in < 3 minutes.
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    High-Quality Deals

    Typically unavailable to individual investors.
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    Co-Invest with Elite VCs

    AV co-investors include VCs like Andreessen Horowitz, Sequoia, Khosla, Accel, and more.
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    Exclusive Deal Information

    Diligence materials, investor decks, company financials all provided. NDA required & enforced.

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AV Headquarters
670 N. Commercial Street
Suite 403
Manchester, NH 03101
General inquiries: [email protected]

Press inquiries: [email protected]

603-518-8112

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Neither Alumni Ventures nor any of its fund are sponsored by, affiliated with, or endorsed by any school. Venture capital investing involves substantial risk, including risk of loss of all capital invested. Achievement of investment objectives cannot be guaranteed. Past performance does not guarantee future results. To see information on all AV fund investment performance, please see here. To see additional risk factors and considerations, please see here.

No content hosted on this website is an offer to sell, or a solicitation of an offer to purchase, any security. Such offers are made only pursuant to the formal offering documents for the funds concerned, which describe the risks, terms, and other important information that must be carefully considered before an investment is made. Alumni Ventures and its affiliates provide advice only to venture capital funds affiliated with AV. No information on this website may be relied upon as personalized advice to any recipient.

Please see Alumni Ventures’ Legal & Privacy Policy here and additional Investor Policies here.

Testimonial/Endorsement Policy: Testimonials and Endorsements were provided without compensation but each provider has a relationship with AV from which they benefit. Management of portfolio companies have received, and may in the future receive, investments from AV, which constitutes a conflict of interest. All views expressed are the speaker’s own. The providers of the testimonials/endorsements were not selected on objective or random criteria, but rather were selected based on AV’s understanding of its relationship with the providers of the testimonials/endorsements. The testimonials and endorsements do not represent the experience of all AV fund investors or all companies in which AV funds invest.

Alumni Ventures is America’s largest VC firm for individual investors based on the combination of total capital raised, number of investments, and number of investors of leading VC firms as reported by Pitchbook and other publicly available information reviewed by AV.

Video Policy: By consuming this content I acknowledge that I may be considering an investment with AV funds for my own or my client’s account. I agree that information contained herein may not be relied upon or used for any other purpose.

Co-investors: Co-investors are shown for illustrative purposes only, do not reflect the universe of all organizations with which AV has co-invested, and do not necessarily represent future co-investors. The identity of a co-investor does not necessarily indicate investment quality or performance.

© 2025, Alumni Ventures. All rights reserved.