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 Today’s product/market fit might be tomorrow’s outdated solution.”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   Be sure to follow the Acquired Podcast: Acquired.fm @AcquiredFM Let People Know You’re An LP on Twitter!   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: Acquia Benchmark Duffel Elastic Glow MongoDB MuleSoft Pachyderm ReplyYes Shopify Sketch Stripe Twilio   Episode Specific Terms: Cloud Infrastructure Compounding Effects Enterprise Infrastructure Flow State Fund Cycle Learn-It-All vs Know-It-All Leverage on Fiddling Luck 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 Follow Acquired: @AcquiredFM, acquired.fm Let People Know You’re an LP on Twitter! Suggestions and Feedback: acquiredfm@gmail.com