Miles Grimshaw - The DNA of Software Companies

**Patrick O'Shaughnessy** (0:00)
This episode is brought to you by Tegus.
Over the years of our partnership with Tegus, they have evolved from a pure expert network into a full company intelligence platform. I've been so impressed by the platform that my firm, Positive Sum, recently made an investment in Tegus. We did so because we feel that Tegus will be the gold standard platform for investing research for decades to come. Tegus streamlines the investing research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard to get qualitative insights, gives instant access to critical public financial data through BamSEC and helps you set up customized expert calls. It's all done on a single modern Saas platform that offers 360 degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co.uk/patrick.
Hello and welcome everyone. I'm Patrick O'Shaughnessy and this is Invest Like the Best. This show is an open-ended exploration of markets, ideas, stories and strategies that will help you better invest both your time and your money. Invest Like the Best is part of the Colossus family of podcasts and you can access all our podcasts, including edited transcripts, show notes and other resources to keep learning at joincolossus.com.

**SPEAKER_2** (1:17)
Patrick O'Shaughnessy is the CEO and founding partner of Positive Sum and the CEO of O'Shaughnessy Asset Management. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of Positive Sum or O'Shaughnessy Asset Management. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.
Clients of Positive Sum or O'Shaughnessy Asset Management may maintain positions in the securities discussed in this podcast.

**Patrick O'Shaughnessy** (1:49)
My guest today is Miles Grimshaw. Miles is in his early thirties and is a general partner at Benchmark. His experience and success belie his age. He was an early investor in Segment, Benchling and Airtable all before they had 30 employees. I have learned a ton from Miles about software investing and that's why I was excited to have him on the show. We discuss his biological approach to investing, whether pure API companies can be good businesses and what most has his attention right now.
Before we transition to the episode, I want to highlight the Founders Podcast, which is part of our Colossus Network. David Senra, who hosts Founders, has devoted his life to learning from history's greatest entrepreneurs and every week he distills the lessons of a different founder. If you want an entry point, I highly recommend starting with episode 136 on Estee Lauder. I hosted David on Invest Like the Best this summer and it's hard not to walk away insanely energized after listening to any episode with him. You can find a link to Founders and that episode in the show notes of this conversation. And you can search all past transcripts on our website, joincolossus.com.
Please enjoy this conversation with Miles Grimshaw.
Miles, so a great place to begin is with this notion of the investor as biologist versus the investor as physicist. And the reason I start here is because when you look at the successful investments that you've made so far across your career, they sort of can't be categorized. Across all the major categories of our style of investing. And so I think this opening frame will help people understand where you're coming from as an investor and sort of what you've done so far before we start to dig in on the specifics of some of the companies and some of the bigger ideas that you formulated so far in your career. So start us with this idea of biologist versus physicist.

**Miles Grimshaw** (3:34)
I don't know that I picked the easy way to go about it. In some sense, I think the easier way is that of a physicist.
And the lens I use there is the idea of having to try and divine a set of rules, a set of axioms that are unbreakable, that you follow, that you look for repetition of, that are consistent and applicable. That's the physicist. You can imagine that these days as the Saas playbook, as Saas metrics, as the comparables of, okay, if you got from one to five really fast with this efficiency, it's all gonna work. And I personally don't think like that. I think of myself and the exploration, what we get to do in early stage, more is that of a biologist. You might imagine Darwin getting off the HMS Beagle, exploring new lands and just amazed at the new species and wondering where they fit into the world and how they mutated to have these adaptations to this environment. And if you think of constantly changing environment, it sort of begets looking for constant adaptations and evolutions and starting with a lens of why, of curiosity, of imagination. At the end of the day, I also think the best companies don't want to be versions of what has been. They want to be the best versions of themselves. And the journey we can go on together is to then be asking, what is our best version of ourselves? YouTube didn't want to be the flicker for video.