Winston Weinberg

speaker

1,528 appearances 2 recordings 2 series first heard Jan 2026 last heard 12 May

Winston Weinberg’s voice in public audio — every appearance, attributed to the second.

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recordings per month · last 12 months

Recordings per month over the last 12 months — 2 in all, peaking in May 2026 with 1.

Appearances

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The Knowledge Project · Speed, Stress, and Better Decisions | Winston Weinberg · 12 May 2026 podcast

I mean, we had this with Harvey where we had, you know, we've had so many folks that said, we trialed your product like three years ago.

We didn't think it was good enough and we don't, we're unsure if it's improved.

And then they log in and they're like, I don't even remember trying the product three years ago.

Like, this is so different.

And I think that also that rate of technology change, people aren't really used to, and especially folks that are not in the tech industry, right?

And with what's happening in AI right now, every release is a massive step change.

And I think it's hard for people to wrap their mental model around that and think about, oh, how do I create, how do I become, you know, anti-fragile where I'm okay with making different choices and really think about the future when everything is changing so quickly.

Yes.

I think hiring senior executives, I've been very up and down about it.

I think I was told to hire senior executives very, very early on, and I refused.

And then I refused too long.

I refused, I'd say, about six months too long.

But if I would have taken the advice when it was given, I think it would have been a huge mistake.

How did you know that you were late?

I saw the impact of what happened when I hired them.

The main advantage of being a founder of a company is if you are always on, which I tried to be,

what you have is you have the context from day one, right?

And if you're always on, your brain, all your brain has to do is do the delta between day one and day two, right?

And so the reason founders are so valuable, I think, to understanding their business and looking forward and both looking forward and looking back is actually just because the cognitive load of

taking everything about the business day over day makes it so you can kind of understand everything that's going on.

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