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Chestnut Street Syndicate and Venture Fund

Network-Powered Venture Capital With Fellow Penn Alums

What It Is

A private investing community for Penn alums and invited guests, featuring a diversified venture fund and deal-by-deal syndications. Chestnut Street Ventures invests in cutting-edge startups—by co-investing alongside top-tier venture capital firms. Members benefit from low minimum investments, shared diligence insights, and curated access to exceptional venture opportunities. It is built on the premise that we can do better together.

Who It’s For

Accredited Penn investors (and invited guests) who want strategic exposure to transformative startup and venture capital. Ideal if you believe in innovation, technology and entrepreneurship—and you value investing alongside fellow alums in life-changing ventures.


Takes almost no time to sign up through our EasyVestTM process.


Why Join

Get smart. Get access. Get involved.

Members of our syndicates receive curated access to life-changing ventures, typically about one deal per month. You can choose to invest in any or none. There’s no fund commitment and no pressure. Just opt in when it’s right for you.

It’s free to be in the community and syndicate. Along the way, you’ll receive:

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    Deal Flow:

    About a deal a month (it ebbs and flows).
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    Content:

    Short, sharp investing insights via blogs, webinars, and analysis from trusted voices.
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    Connections:

    Regular in-person events.
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    Founder Access:

    Opportunities to meet the entrepreneurs building the future.

The Types of Ventures We Access for You

Whether you’re looking to invest, learn, or contribute expertise, our syndicates put you at the center of the action — with a group of aligned peers.

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    Pre-seed to Later-Stage:

    We invest as early as possible, but we show you deals at a variety of stages. They are all deals AV funds are investing in.
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    Focus:

    Our syndicate will give you access to deals appropriate to the syndicate, but expect variety.
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    Geography + Leads:

    We look for great deals everywhere and co-invest alongside a wide variety of strong lead VC firms. AV believes in large and diversified venture portfolios — we want to help you build yours.





Fund Overview

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    A community of Penn alumni investors, entrepreneurs, and friends
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    Raises and invests a new fund every year
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    Access to Syndication investment opportunities
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    Notable investments: Burrow, Integrate, data.world, and Ghost Robotics
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    Part of Alumni Ventures, America's Largest Venture Firm for Individuals and a "Top 20 Venture Firm" (CB Insights '24)

See video policy below.


How It Works:

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    Join the community and syndicate (it’s free)

    It takes < 3 minutes with EasyVest.
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    Receive ~1 deal per month with access to our due diligence

    See our "Why We Are Investing" Video Briefs. Participation is Opt-In.
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    Participate – as much or as little as you want

    Read our blogs and white papers, attend zoom webinars, attend IRL events.
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    Get Early Access to our Fund

    Gain entry to our fund with special terms.

About Our Fund

Five Reasons this might be a good choice
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    Simplest Way to a Startup Portfolio

    Easily build a high-quality portfolio of 20-30 startup investments — without sourcing deals yourself, negotiating terms, or managing multiple investments.
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    Co-Invest with Top-Tier VCs

    Invest alongside leading venture capitalists, leveraging their rigorous diligence, extensive networks, and proven expertise to identify promising opportunities.
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    Diversification and Risk Management

    Achieve built-in diversification across sectors and companies, mitigating risk while capturing the potential upside of breakthrough innovations.
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    Early Access to Transformative Tech

    Gain curated, early-stage exposure to breakthrough sectors including AI, biotech, cyber, space, and advanced manufacturing.
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    Participate in the Future of Innovation

    Invest in sectors ripe with innovation — positioning your capital to compound long-term returns as these technologies scale.

Access Curated Deals Led by Top VC Firms

These firms have co-invested in many deals with Alumni Ventures

These leading venture firms have backed some of the most successful companies in the world.
Co-investors are shown for illustrative purposes only, do not represent all co-investors with which Alumni Ventures has invested, and are not necessarily indicative of future co-investors. The identity of a co-investor does not guarantee investment quality or performance.


Takes almost no time to sign up through our EasyVestTM process.


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, spreads risk and upside across stage, sector, and geography.
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    Co-investing with the best.

    AV has partnered on 250+ deals alongside blue-chip firms such as Sequoia, Andreessen Horowitz, and NEA, giving you similar terms and the benefit of their support.
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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.

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 News

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


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)

Review Live Deals & Optionally Invest Alongside Alumni Ventures and Other Elite Venture Capital Firms

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    Easy Sign Up Process:

    Our EasyVest makes accessing deal flow easy as pie, and takes almost no time.
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    Professional-Grade Deal Access:

    Get access to highly-competitive deals typically not available to individuals.
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    Co-Invest with Elite VCs:

    Invest alongside AV and other firms like Andreesen Horowitz, Sequoia, Bessemer, Khosla, and Google.
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    Exclusive Deal Information:

    Review all diligence materials and gain VIP access to live deal discussions with our investment teams. NDA required and enforced.