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Winston Weinberg

๐Ÿ‘ค Speaker
1528 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

So I'll basically be like, like, I know who I want to lead the next fundraise.

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

My point here is we almost every single time we probably could have gotten much higher valuations than we took.

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 instead we chose the best investors and the ones that I trusted and personally wanted to work with.

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 the main thing about fundraising is you should always think of it as start it six months ahead of time and you will do much less work than if you actually go out and do the process.

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 what I mean by this is, and I learned this from some other founders who are really good at this, is what they do is they try to basically get folks to come in for a couple million dollars, like just like one or two, and you give them information rights.

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 you say, here, we're going to tell you how we're doing.

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 what you do with that is now they can check on the business, 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 the most important thing, at least that I have found, I think VCs care about this the most, and hopefully they do, because it would be a good thing if they do.

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'll tell you.

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

Is trusting that when the founder says something's going to happen, it's going to happen.

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 do that over enough times, hopefully VCs really trust you.

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 so going back to that strategy, if you let them invest a little bit in the beginning,

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 say, hey, in three months, we're going to do X, Y, Z. And then you say, in six months, we're going to do X, Y, Z. And then in nine months, we're going to do 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 at the end of the year, this is what's going to happen.

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 those things come true, they start to really trust you and they start to believe you.

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 when you go out to do that fundraising process, it can happen in 12 hours.

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 don't need to make tons of materials.

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 don't need to go out and do this massive, massive process.

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

The problem with this is you're then not optimizing price.

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 that is assuming that you are not trying to optimize price.