Show Notes

[00:00:00] – (First Question) – Why he wants to be the Larry David of investing

[00:00:18] – Why his investing style is best described as trend following

[00:02:23] – The biggest inspirations/influencers on Howard’s investing

[00:04:57] – What made his second mentor, Fred Wilson such a great investor

[00:08:10] – Formation of Wall Strip

[00:10:51] – Why weird is so important in his investment philosophy

[00:13:14] – Understanding his investment philosophy through his investment in Rally Road.

[00:19:20] – His assessment of the fintech space

[00:27:12] – Why fintech pushes away from human nature

[00:29:08] – Major trends in fintech that have his attention

[00:33:20] – What stands out about the teams at these companies he invests in

[00:34:55] – Thoughts on fractionalization plays

[00:35:02] – Capital Allocators podcast episode

[00:35:12] – Venture Stories Podcast

[00:38:21] – Any major trends that are changing and worth attention

[00:40:24] – The Tipping Point: How Little Things Can Make a Big Difference

[00:41:44] – His take on the media landscape

[00:43:28] – Kindest thing anyone has done for him