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Winston Weinberg

๐Ÿ‘ค Speaker
814 total appearances

Appearances Over Time

Podcast Appearances

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

And a lot of I think what's happening to AI companies or is going to happen to them, and it happened to us in early 2024, is you do a bunch of front end and you make really pretty UIs and really nice demos, right?

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

And then you use that to land all the customers.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

And now you have a lot of actual active customers and you haven't invested in the architecture and the infrastructure of hundreds of thousands, millions of customers using your product.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

And we kind of made that mistake in 2023.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

And in the beginning of 2024, something that kind of slowed down our shipping velocity is we added just tens of thousands of users in like the Q4 before that, right?

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

And we didn't quite have the infrastructure like to support that.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

And now if you look at our team, it's almost like 40% of our entire EPD org is very senior from like a Databricks or something like that, infrastructure engineers.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

And it's a long term bet that as you get these agentic systems that are processing tens of millions for us, I think last year we almost did like half a billion documents or something like that, that you need the infrastructure to actually support that.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

So it's not just about how do you win the demo and how do you win the deal, but how do you actually create an enterprise, very scalable infrastructure on your product?

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

And I see a lot of AI application layer companies not doing this.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

What I would tell them actually is your GRR matters.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

And I think like one thing that a lot of investors in the AI space have been not paying attention to is GRR.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

They've been basically just looking at net new ARR and kind of being like, ah, churn is fine because they're going so fast that maybe they'll pivot or they have some customers.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

I think that's a huge mistake.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

You're going to see a lot of companies in a lot of verticals that go really, really fast to signing a bunch of customers because maybe there was only one in the vertical and now there's a second player, etc.,

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

But then they have to actually support all of those customers.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

And if you don't have the infrastructure in place and you make a bunch of promises up front and then all of that falls down, you'll start losing customers really, really fast.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

And I see a lot of AI companies not focusing on this.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

And I think that's going to be like a huge reckoning for folks once they get past 100 million ARR.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

Agree.