Gaingels And Khosla Ventures Pick Up The Pace

This is a monthly feature that runs down some of the most active investors in U.S.-based companies, looks at some of their most interesting investments, and includes some odds and ends of who spent what. Read last month’s entry here.

In September, both California’s Khosla Ventures and Vermont-based Gaingels tied for third place among most active U.S. investors. One month later, the two firms moved up the list as the most and second-most active investors among those making deals in the U.S.

In fact, both made more domestic investments in one month than either had in any previous month this year.

Let’s take a look at which firms did the most in the spooky month of October:

Gaingels, 14 deals

After a prolific investment cadence last year, Gaingels has slowed this year. October was only the second month in 2023 in which the firm hit double digits in U.S. deals, and the 14 deals represents its largest amount in one month since last November.

The firm mainly concentrated last month on seed through Series B deals, which is pretty usual for the Gaingels. The biggest round it participated in was a $16 million Series A for New York-based Modal Labs, which develops machine-learning software to help run code in the cloud.

Gaingels investments last month included everything from AI tax filing startup TaxGPT to Anyplace, a startup that helps people find furnished live/work places.

Khosla Ventures, 10 deals

Khosla had its busiest month since May of last year in terms of investing in U.S. startups.

In fact, the firm has been getting progressively busier on that front, investing in at least a half-dozen deals in each of the last five months.

The biggest U.S. deal Khosla took part in last month was co-leading a $43.5 million Series A for Saratoga, California-based micro-LED display developer Mojo Vision. The round is interesting because in January the company announced a pivot from developing augmented reality contact lenses to its new focus of high-resolution micro-LED displays.

Andreessen Horowitz, 8 deals

Andreessen Horowitz topped this list in September with 14 deals, but last month was a little slower.

A year ago, a16z actually was one of the top investors, announcing 13 deals in October 2022. But as we pointed out in a piece last month, the firm has continued to slow its pace in the last two quarters — investing in its lowest number of deals in both Q2 and Q3 since the final quarter of 2020, Crunchbase figures show.

The fourth quarter may continue that trend.

However, it didn’t shy away from taking part in a big $125 million Series C for New York-based mental health startup Headway that values the company at $1 billion, per Reuters. It also continued its interest in AI, participating in a $1.7 million pre-seed for San Francisco-based generative AI startup Klu.ai.

Nevertheless, the firm may be “optimistic” about tech, but it is treading lighter than in the past.

Index Ventures, 6 deals

Index Ventures kind of came out of nowhere last month with a half-dozen announced deals in U.S. startups.

The San Francisco-based firm had not made more than two deals in the U.S. in any other month this year, and it’s the most such deals the firm has pulled off since February of last year.

Index actually announced no deals domestically in July, August and September, per Crunchbase.

Perhaps it was saving them up for October.

Index also caught a little bit of the AI bug — as has every VC firm. The firm helped co-lead a seed and participated in a Series A for New York-based Siro, an AI coach for field sales, and led a seed for San Francisco-based Class Companion, which has created an AI technology that allows professors to provide students with feedback.

Also notable:

Methodology

This is a list of investors which took part in the most rounds involving U.S.-based startups. It does not include incubators or accelerators due to the fluctuations their investment numbers can have.

Illustration: Dom Guzman