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Pat Grady

Pat Grady

Search complete. 11 mentions across 7 episodes found for "Pat Grady".

Sep 22, 2026

Patrick O'ShaughnessyHOST
43:42
What about aggression? Like, that seems kind of like a trope.
Gabe StengelGUEST
43:45
You've interviewed Pat Grady.
Gabe StengelGUEST
43:46
Pat Grady was at our board meeting on Wednesday, and we presented what was a extremely aggressive plan for next year in terms of hiring goals, commercial goals, product goals.
Gabe StengelGUEST
43:57
And one of the reasons I love Pat is because he boils everything down into, like, two bullet points, and it's logically infallible.
Gabe StengelGUEST
44:06
And, you know, he's just like, "Premise one, premise two, this is the result." And he goes, "Gabe, well, if everyone in finance is gonna make a buying decision on AI in the next eighteen months, and they are definitely gonna buy something no matter what, even if you're not there, then the only thing that matters is that you can blitz the market as quickly as possible to make sure that you are there.
Patrick BoyleHOST
37:31
and no individual investor actually receives the average.
Patrick BoyleHOST
37:35
Each one gets the PAT they happen to land on.
Patrick BoyleHOST
37:39
It's just that with a distribution this skewed, the overwhelming majority of those PATs cluster down near the median, in loss territory, while the handful that would deliver the advertised average are off in a tail that almost nobody reaches.
Patrick BoyleHOST
37:56
Leopold isn't betting on a bad expected value.
Patrick BoyleHOST
38:00
He's betting that the math applies to other people.
Ollie ForsythHOST
28:35
We have longevity in supporting companies, but also inside venture funds, creating longevity around stewardships and, you know, making sure these venture funds actually, like, outlive the founders, right? How do you guys think about building that? You know, we've seen the likes of Sequoia.
Ollie ForsythHOST
28:49
You mentioned Alfred Lin earlier, Pat Grady, who are now taking over Sequoia.
Ollie ForsythHOST
28:53
I think they've done a really interesting job, and it's not talked about enough, I don't think.
Ollie ForsythHOST
28:58
How do you think about creating longevity and stewardship?
Tanay TandonGUEST
0:49
That's really what we get excited about.
Siddhartha AhluwaliaHOST
0:55
I'd love to start by the letter that you wrote to your team that Pat Grady shared on Twitter.
Siddhartha AhluwaliaHOST
1:02
that you're looking for people who are almost like heat-seeking missiles for pain.
Siddhartha AhluwaliaHOST
1:07
Can you elaborate more about it?
Chris OlsenGUEST
13:27
This is a stereotypically very hard working group of people, and that continues to this day.
Chris OlsenGUEST
13:35
I remember when You know, the week after Pat Grady had Zoom go public amidst COVID, you know, this meteoric successful investment, he did something like 75 meetings the next week.
Chris OlsenGUEST
13:47
Like it's that kind of mentality that the firm has where it's a, you're only as great as your next investment.
Chris OlsenGUEST
13:55
And it's driven by this understanding that like, this is an extraordinarily hard thing to do and to be successful at this challenge, you need to show up with an appropriate level of standards and discipline and work ethic.

1 HR 7 MINS LATER

Turner NovakHOST
81:25
How did that usually go?
Chris OlsenGUEST
81:27
Yeah, it does happen.
Chris OlsenGUEST
81:28
Now, you know, it's usually not like, you know, it's not Pat Grady showing up in Atlanta.
Chris OlsenGUEST
81:35
It's usually like the junior person or it's usually let's meet on Zoom or, you know, it's a it's a remote approach to it.
Harry StebbingsHOST
40:43
Okay.
Harry StebbingsHOST
40:44
There's Doug Leone, there's Pat Grady, there's Alfred Lin, there's Sean Maguire.
Harry StebbingsHOST
40:47
I'm gonna choose one lesson from each.
Harry StebbingsHOST
40:50
Start with Doug.
Harry StebbingsHOST
44:22
We must always bring energy, bring preparation to every single company meeting we have.
Harry StebbingsHOST
44:27
It's never enough." I, I just love that humility.
Harry StebbingsHOST
44:30
Like, this is, this fucking Pat Grady-
Julien BekGUEST
44:32
Yeah
speaker_1NARRATOR
3:16
Shaun Maguire uses an ELO-style lens.
speaker_1NARRATOR
3:20
Pat Grady thinks in vectors, and Alfred Lin warns against mistaking an outlier operator for an outlier founder.
speaker_1NARRATOR
3:28
The firm values judgment, political skill, and intensity over polished resumes.
speaker_0NARRATOR
3:34
That's especially important in AI, where CV bias can be dangerous.

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