ACQ2: The Acquired Interviews

We are joined by Chetan Puttagunta, General Partner on Benchmark, talking his investment philosophies, enterprise technology trends, and the uniqueness of Benchmark. How is this firm with only five partners and no associates so repeatably successful? Chetan shares the story of his very first investment, MongoDB, and lessons learned from his other investments and board positions in Elastic, Sketch, Duffel, Mulesoft, and many others.

Chetan also helps us understand how he balances staying open-minded enough to let founders shape his vision of the future (and not the other way around), while staying educated on areas where he thinks the future is bright.


“The product/market fit question, I don’t find to be a conclusive one…because one of the assumptions is that you’re assuming the market itself is constant, which we all know is not true. Today’s product/market fit might be tomorrow’s outdated solution.” – Chetan Puttagunta, @chetanp


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Show Bookmarks:

[00:00] – Show intro and introduction of Chetan Puttagunta

[05:00] – Operations at Benchmark

[09:20] – How does Benchmark choose where they invest?

[11:20] – Product/Market Fit

[14:50] – Themes, Theses, and Trends and being flexible in investing

[20:32] – How to educate yourself on emerging markets

[29:00] – Enterprise Investing

[34:55] – Thoughts on being a VC vs Entrepreneur, and investing in Enterprise

[44:05] – What Chetan wants to improve

[47:09] – “Two-Sport” athletes at Benchmark


People Worth Knowing:

Andy Rachleff

Don Valentine

Eric Vishria

Peter Fenton

Steve Blank

Warren Buffet


Companies Mentioned in Episode:















Episode Specific Terms:

Cloud Infrastructure

Compounding Effects

Enterprise Infrastructure

Flow State

Fund Cycle

Learn-It-All vs Know-It-All

Leverage on Fiddling


Product/Market Fit

Relational vs Non-Relational Databases

Sharding Issues

VC vs Entrepreneur

Yacht Problems


Ben and David’s Affiliations:

Wave Capital, @WaveCapitalVC

Pioneer Square Labs, @psl

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What is ACQ2: The Acquired Interviews?

ACQ2 is Ben and David's conversations with expert founders and investors. Acquired the stories of great companies — and ACQ2 dives deeper into the lessons we can learn from them, often with the protagonists themselves.