Yotam Rosenbaum’s Post

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YC Founder, Mentor, Investor

I’ve invested in 255 Y Combinator companies. Here is why and how: In 2017, a couple of years after Earbits was acquired, my co-founder and I wanted to start investing in other startups. As YC alumni, we have early access to YC deals, which arguably offers the best deal flow an investor could hope for. However, identifying unicorns before they turn into unicorns is nearly impossible. So instead of cherry-picking, we decided to take a different approach: index investing in YC companies. Our thesis was that by building a diversified portfolio, we would be able to produce better results while lowering risk. So we put the theory to the test. Our first fund was fairly small, and we invested in 19 companies from the S17 batch. Within a few years, two of the companies turned into unicorns, and another was acquired by the NY Times. So, we did it again in W21. This time, we invested in 50 companies. To our delight, the second fund performed as well as the first. Both funds are outperforming 90% of benchmarked funds from their respective vintages. To date, we’ve invested in 255 companies across 5 batches. We take great pleasure in writing easy and often first checks to exceptional founders. ____ 𝐓𝐰𝐢𝐜𝐞 𝐚 𝐲𝐞𝐚𝐫 𝐰𝐞 𝐢𝐧𝐝𝐞𝐱 𝐢𝐧𝐯𝐞𝐬𝐭 𝐢𝐧 𝐘 𝐂𝐨𝐦𝐛𝐢𝐧𝐚𝐭𝐨𝐫 𝐜𝐨𝐦𝐩𝐚𝐧𝐢𝐞𝐬. 𝐖𝐞 𝐛𝐞𝐥𝐢𝐞𝐯𝐞 𝐝𝐢𝐯𝐞𝐫𝐬𝐢𝐟𝐢𝐞𝐝 𝐩𝐨𝐫𝐭𝐟𝐨𝐥𝐢𝐨𝐬 𝐰𝐢𝐧. 𝐃𝐌 𝐦𝐞 𝐢𝐟 𝐲𝐨𝐮’𝐝 𝐥𝐢𝐤𝐞 𝐭𝐨 𝐥𝐞𝐚𝐫𝐧 𝐦𝐨𝐫𝐞. #founder #entrepreneur #startup #venturecapital #vc

you basically saying that you do not understand anything about what you invest in, as old Munger would say: "The idea of diversification makes sense to a point if you don't know what you're doing"

I agree that when it comes to very early-stage investing, being selective is not as important as being fast and profligate. Dragging an early-stage company through 6 months of due diligence actually strangles the very startup you are trying to evaluate. Better to be more humble, just accept that it's impossible to know, and just invest in as many as possible to take advantage of the law of large numbers.

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John Linford

I build decks (sales + pitches, not patios) | brand articulation >> beautiful presentations >> $$ | professional magician (no, really) | co-founder @ Deckability

1mo

This is like the Chik-fil-a principle: you know CFA is always going to choose good real estate. Buy up and build next to them, you're far more likely to succeed. This is the 'you're the average of the 5 people you surround yourself with' taken to a new level.

Kevin Jurovich

Co-founder, CEO at Circles | Startups & VC

1mo

Love this…talk about next level deal flow

Konstantin Bolshukhin

CEO at mgmate. App to run insightful managers' 1:1s.

1mo

Thats what they call a "track record"

Curious to hear what you guys put in on the unicorns and what the value is today.

Paul Brezovsky III

NYU Stern MBA Candidate | Venture Capital Enthusiast

1mo

Would love to learn what the breakdown of those 255 companies are, as well as some of their stories! I’m sure there’s some really great journeys in there

Gareth Adams

Co-Founder at Atandem

1mo

There are many ways to invest and indexing can be as good as any. My question is a simple one - across the 255 how many are cash flow positive?

Jamal K, ACA

On a Mission to Raise $200M in 12 Months for Founders Using the S.E.E.D System | Guaranteed Investor Meetings To Close Your Round| $400M Raised

1mo

That's awesome! Your approach of investing in a bunch of YC companies instead of just a few is really smart. 

Anric Blatt

🆎 builds client 🧲 capital ⚙️ for entrepreneurs to generate IMMENSE sustainable WEALTH, IMPACT & INFLUENCE

3w

its actually a great model Yotam for those of us that want to invest in that space but dont have the time or interest to go into each of these individual opportunities and are not on their radar. Normally I am not a fan of funds (or pooled investments) - even though I spent 30 years building fund management companies, but this one does make sense to me ...

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