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Matt LeMay

Published podcast speaker

Claims
17
Episodes
1
Shows
1
Named items
2

Books, apps, and tools

The evidenced stack.

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book / recommends

The Wisdom of Insecurity

“Radical Focus, by Christina Wodtke, is obviously, I cite it a lot in my book, I think it's the best book about OKRs. I love her style of writing. I love the way she tells stories. I love the focus on focus, this idea that again, the way you do it is less important than the result of the way of doing it. I just find that so inspiring, always. The other book, this is a bit of a curveball, is by Alan Watts, the Buddhist philosopher. It's called The Wisdom of Insecurity. And a lot of the way I talk about control, and giving up control, comes from that book. It also has a concept. It opens with a concept called the law of reverse effort, which is that sometimes, the harder you try, the worse you make things. When it comes to setting goals, doing OKRs, doing strategy, I think about this a lot, that there is a tendency sometimes to put effort towards the overcomplication of things, which in turn makes those things less effective, what they're ultimately intended to achieve. So, highly recommend that book. It helped me a lot through some dark times, mentally. There's an idea in the book. He talks about how trying to keep yourself perpetually safe in an imagined future is effectively killing yourself to the present. And ooh, that hit hard. That hit me really, really, really hard. So, highly recommend that book. If the things we've talked about today make you even a fraction of, as anxious and fearful as they make me when I navigate them in my work, then I highly recommend The Wisdom of Insecurity, by Alan Watts.”

Lenny's Podcast · 14 Aug 2025

Evidence receipt · Source ↗

book / recommends

Radical Focus

“Radical Focus, by Christina Wodtke, is obviously, I cite it a lot in my book, I think it's the best book about OKRs. I love her style of writing. I love the way she tells stories. I love the focus on focus, this idea that again, the way you do it is less important than the result of the way of doing it. I just find that so inspiring, always. The other book, this is a bit of a curveball, is by Alan Watts, the Buddhist philosopher. It's called The Wisdom of Insecurity. And a lot of the way I talk about control, and giving up control, comes from that book. It also has a concept. It opens with a concept called the law of reverse effort, which is that sometimes, the harder you try, the worse you make things. When it comes to setting goals, doing OKRs, doing strategy, I think about this a lot, that there is a tendency sometimes to put effort towards the overcomplication of things, which in turn makes those things less effective, what they're ultimately intended to achieve. So, highly recommend that book. It helped me a lot through some dark times, mentally. There's an idea in the book. He talks about how trying to keep yourself perpetually safe in an imagined future is effectively killing yourself to the present. And ooh, that hit hard. That hit me really, really, really hard. So, highly recommend that book. If the things we've talked about today make you even a fraction of, as anxious and fearful as they make me when I navigate them in my work, then I highly recommend The Wisdom of Insecurity, by Alan Watts.”

Lenny's Podcast · 14 Aug 2025

Evidence receipt · Source ↗

Claim ledger

What Matt said.

2 transcript-backed records

02 / commitment

I think especially given that we are no longer in a zero interest rate environment, given that hiring and retaining employees is expensive, given that companies are looking at cost savings, I think we are in a moment where it is really incumbent upon each product team and each member of each product team to be able to understand, articulate, and work towards the top line business impact of their own work.

“I think especially given that we are no longer in a zero interest rate environment, given that hiring and retaining employees is expensive, given that companies are looking at cost savings, I think we are in a moment where it is really incumbent upon each product team and each member of each product team to be able to understand, articulate, and work towards the top line business impact of their own work.”
Speaker
Matt LeMay
Publisher
Lenny's Podcast
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