Anti

Anti-portfolio (n): The collection of investment opportunities that a venture capitalist has passed on, but which have later proven to be highly successful.

Primary Venture Partners

Ben Sun founded Primary Venture Partners in 2015 with the goal of reshaping seed investing in New York City.

His accomplishments in NYC venture over the past decade are Unrivaled

• Invested in 8 unicorns out of 40 companies

• Grew Primary AUM to $1B+

• Early investor in Coupang (“the Amazon of Korea”), which now has a $40B market cap

Sun is vocal about underwriting a company’s ability to get to the Series A round

But today we’re not talking about the hits, just the misses

In 2010, a peer told Sun about a company called Pinterest

After evaluating Pinterest and a related competitor, he felt that neither could demonstrate superiority over the other. Without conviction on a clear winner, Sun decided to sit it out.

Today, Pinterest is worth more than $20B on the stock market.

Notation Capital

Notation Capital is a venture capital fund that invested in more than 100 companies, primarily at the pre-seed level. LPs include Invesco, Cendana Capital, Brown Advisory, Andy Weissman from Union Square Ventures, and more

Co-founder Nick Chirls recently left Notation to co-found Asylum Ventures

In venture investing, loss takes time to sink in before you truly feel The Impact.

Headway is a mental health marketplace that helps people find therapists using a free portal. The company launched in 2019 and benefited greatly from the pandemic lockdowns.

Andrew Adams, the founder of Headway, was a NYC resident who moved to California and in the process of doing so, realized how hard it is to find a therapist. His frustration with the situation inspired him to start Headway

Headway makes money by taking a commission from insurance providers, who get value from accessing the large number of therapists in the Headway network. Providers also get value by managing insurance payments through the platform. In essence, the marketplace is three-sided

Nick Chirls / Notation Capital had the opportunity to invest at the pre-seed level in 2019 but passed because there were other mental health provider search products in the market.

This miss represents what could have been a 150-200x home run depending on pre-seed valuation

Today, Headway is worth $2.3B and has raised from a16z, Spark Capital, Accel, and more

Bessemer Venture Partners

Bessemer is one of the oldest and most storied venture funds in the world.

The fund has more than $20B AUM and was founded in 1911

Bessemer is known for a portfolio filled with money Trees.

• 145 IPOs

• Portfolio Companies

  • Pinterest

  • LinkedIn

  • Shopify

  • Yelp

  • Twitch

  • Toast

  • Wix

  • Anthropic

A unique feature of the fund is their transparency about losses

On their website, they list all of the major deals they passed on

It’s a long list

• Airbnb

• Apple

• Atlassian

• eBay

• Facebook

• Fedex

• Google

• Instacart

• Intel

• Intuit

• Kayak

• Okta

• PayPal

• Snapchat

• Zoom

Today, the companies Bessemer passed on are collectively worth $7.6T

Dealflow: Bezel

A friend of mainstreet is investing in Bezel’s seed extension through an SPV.

The company raised an $8M seed round at a $30M valuation last year and are taking on additional capital this year at a significant markup.

Bezel plans on raising an institutional round next year

Other investors include:

• BoxGroup (Plaid, Airtable, Ro)

• Courtside VC (StockX, The Athletic)

• Kevin Hart, Michael Rubin, J Balvin

Minimum investment is $7,500.

If interested, reply to this email for an introduction

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