Last week I sat down with Patrick O’Shaughnessy as a guest on his podcast.
Patrick has one of the most popular investing podcasts which I have linked to here in the past.
I am grateful for the time he gave me to discuss my style and point of views on investing and glad I got to make him laugh.
In Patrick’s words:
My guest this week aspires to be the Larry David of investing, and we discuss why. Howard Lindzon is hard to categorize. He’s primarily an early stage investor right now, but he’s participated in all types of investing. He describes himself as a trend follower and always has a unique take on popular topics.
In this conversation, we cover his investing history and his take on the fintech investing landscape. What I’ll remember most is the idea that we should focus on what is happening versus what we think will happen or might happen. There is a Peter Lynch-like quality to some of Howard’s thinking, and a willingness to embrace the weird that I find very appealing. The few times I’ve met Howard, I’ve smiled or laughed most of the time, which is about as nice a thing as I could say about someone.
He’s a good example of why I like this podcast format. His investing style bears literally no resemblance to my own, but it got me thinking about a lot of new things. I hope you enjoy our chat.
I think we covered a lot of ground and I hope you enjoy listening.
In our dive into the ‘Larry David’ of investing philosophy, I forgot to point out the alpha to be found by walking the streets and simply using your eyes and ears (our internal quants). There are edges to be found just trusting your own style and instincts and it can come from world travel or just knowing the neighborhood that you have never ventured from.
If you want the summary topics discussed in the podcast…here you go:
0:00 – (First Question) – Why he wants to be the Larry David of investing
0:18 – Why his investing style is best described as trend following
2:23 – The biggest inspirations/influencers on Howard’s investing
4:57 – What made his second mentor, Fred Wilson such a great investor
8:10 – Formation of WallStrip
10:51 – Why weird is so important in his investment philosophy
13:14 – Understanding his investment philosophy through his investment in Rally Road.
19:20 – His assessment of the fintech space
27:12 – Why fintech pushes away from human nature
29:08 – Major trends in fintech that have his attention
33:20 – What stands out about the teams at these companies he invests in
34:55 – Thoughts on fractionalization plays
35:02 – Capital Allocators podcast episode
35:12 – Venture Stories Podcast
38:21 – Any major trends that are changing and worth attention
40:24 – The Tipping Point: How Little Things Can Make a Big Difference
41:44 – His take on the media landscape
43:28 – Kindest thing anyone has done for him
Also published on Medium.