Listen to This Podcast Episode Here

by Patrick O’Shaughnessy

My guest this week is a good friend and a business mentor of
mine. Chetan Puttagunta is a general partner at Benchmark Capital and has a
remarkable track record of investing in early stage software businesses,
including several like Mulesoft, MongoDB, and Elastic that went on to be public

Chetan has been my key guide for understanding the world of
enterprise software as we at O’Shaughnessy Asset Management have built an
investing platform called Canvas. His advice has been critical to our early
success. In this episode we explore the history of software and software
investing, and go into the details on how to build and grow new software
businesses. We discuss product, sales and marketing, recruiting, scaling, and
everything in between.

Please enjoy this great conversation with one of my favorite business and investing thinkers.

Show Notes

1:34 – (First Question) – How Chetan found MongoDB and
decided to invest in it

8:01 – The evolution of databases in the growth of

16:19 – Market penetration of this space and what investors
should be thinking about

21:46 – Advice how companies can build software effectively

25:12 – Tactics to effectively implement empathy led product

30:33 – Companies asking users what to build vs telling
users what they want

34:26 – The need for the right capital, and patient capital
in particular

37:55 – Creating the perfect customer experience

44:37 – Common reasons they don’t invest in a company

48:48 – Lessons on scaling, especially in sales and

52:47 – Best recruiting pipeline strategies

59:56 – Pitfalls of unit economic traps

            1:00:23 – The
Dangerous Seduction of the Lifetime Value (LTV) Formula

            1:01:34– The
Hierarchy of Engagement

1:02:18 – What has changed for Chetan in his time working
with the team at Benchmark

1:06:009 – Later stage life cycle business considerations
and Amazon’s AWS

1:13:29 – Business model of open source software

1:15:54 – Being default open

1:17:53 – Kindest thing anyone has done for Chetan

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