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[00:03:13] - [First question] - Some of his early key formative experiences that shaped his worldview as an investor
[00:06:29] - How much software businesses have changed since he started investing in them
[00:08:28] - The key insight that led him to create TCV
[00:11:36] - Generating returns by swinging less and raising your average
[00:15:06] - Understanding and evaluating a value proposition in its early stages
[00:22:08] - What slightly crazy founders look like and why it’s important for a company
[00:25:47] - Whether or not we’re in the golden age of content already
[00:28:27] - Why Peloton was rejected so many times before TCV invested in them
[00:32:32] - Things founders often need from him and how he helps them succeed
[00:36:15] - Lessons learned from investing in public markets versus private ones
[00:41:35] - Advice for founders when it comes to conveying their ideas to investors
[00:44:55] - The social dimension of interactive and network building content
[00:46:18] - How important maintaining a focus in the early days is for a new company
[00:48:07] - The most challenging aspect of executing his strategy today
[00:50:48] - One of the most emotionally stressful episodes while launching TCV
[00:53:44] - Supporting your founders during the good and tough times
[00:55:16] - New potential headwinds and tailwinds in the tech space writ large
[00:59:14] - Things people might be overlooking today that could be great opportunities later
[01:02:58] - Whether or not internet companies are threatened by the crypto boom
[01:04:32] - What most has him most excited about the world today
[01:06:20] - Advice for company building in the investing world in general
[01:09:48] - The kindest thing anyone has ever done for him