Howard Lindzon – Fintech and Trend Following – [Invest Like the Best, EP.109]

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.

Show Notes

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 Wall Strip

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