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It just makes comparing funding rounds hard to understand, since money in the bank is money in the bank, and a lot of the "committed capital if you reach a milestone" is capital that would be easy to get if you reached that milestone, if it is sufficiently advanced, and has enough outs, etc., that you may as well have just raised another round in the future.
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Note that even that "money in the bank" of traditional venture firm is not really money in the bank. VC, PE, and hedge fund managers usually don't have all the cash for the fund sitting in the bank at all times. Rather, their agreement with the LPs that fund the fund is structured as a series of capital calls: it gives the fund the right to demand that their LPs deposit cash in their bank accounts within 10-30 days, which can then be used to fund the investments that the VC firm makes. The capital calls are backed by legal documents enforceable in court, with pretty stiff penalties for failing to meet a capital call.

Such a funding structure here isn't all that different: the funding agreement gives OpenAI the right to call on their backers to make certain cash deposits, contingent upon milestones being met. Deep down inside, "money in the bank" doesn't actually exist, it's just mutual agreements backed by force of law.

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When a startup raises money without contingencies, typically they do get a large amount of money in the bank all at once.
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If investments are not tranched then the money is not delivered in tranches, yes.

The first rule of tautology club is...

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That’s logically inconsistent. If the company was performing poorly enough that they couldn’t meet their funding milestones from a previous round, they’re not going to have an easy time raising the same money in a future round.

The milestones aren’t a hard-stop that forbids the previous funding round participants from providing the money if they still choose. It’s just an out.

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sure they can. that's the whole point of the "pivot"
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What I am saying is that if you do meet the milestones from your previous round, you're going to have an easy time fundraising anyway, so funding contingent on milestones isn't that different than just saying "well, if we need more money we can do another round"
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Fundraising rounds are difficult, laborious, and distracting. It would be extremely different to try to multiply the number of rounds by 3-5X. There's nothing easy about that.

You're also ignoring that the market changes frequently. If you only raised as much money as you needed for the next 4-6 months with plans to re-raise all the time, you'd have to constantly be sizing your growth plans up or down based on how the market felt about startup investing that month.

Imagine the company having to either do speed hiring or large layoffs every few months to adjust to the size of the fundraising round they were able to get this time around.

Nothing about what you're suggesting would be easier, or easy at all

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It seems pretty simple:

Funding Round A: VC “A” invests 200M (100M immediately and another 100M if sales grow 10% or whatever)

At 6 months the company will either get the other 100M automatically (meaning they grew sales 10%) or they don’t (meaning they grew less than 10%).

Assuming it’s the later they can then do another round during which they try to get the other 100M. In all likelihood VC “A” won’t be interested (or interested at a lesser amount). They could go ask VC “B” for an investment but it will likely be less than 100M as well because they didn’t grow as much as “the market” anticipated.

Nothing complicated at all.

I’ll give you $1 dollar for your banana today and another dollar in a week when it has ripened. If it’s rotten when I come to get my banana I won’t give you the other dollar. You have your original $1 and you can still try to sell your rotten banana to another HN reader but you probably won’t get another dollar this time.If instead you have a ripe banana I’m sure you could easily find a buyer.

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Why not announce the funding after the milestones have been met?
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The funds are committed under the terms of the deal (share price, things like board seats, and other details). There are legal obligations to provide it.

This is a common structure for large investments. It would be really inefficient for all of these investors and companies to have to have the money sitting in cash to do a deal and then transfer it into the company's bank where it sits and earns interest for years until they can deploy it.

Even VC firms who raise funds work this way. The capital is "committed" but investors don't wire all of the money over right away so it can sit in the VC firm's bank accounts, waiting. The VCs do what's called a "capital call" through which they're legally bound to provide the money they committed when requested, under the terms of the deal.

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It's splashier this way, and is meant to shape the narrative, make other companies fear their warchest, and make hiring easier. Of course, those who are in-the-know won't be fooled, but the perception of the general public will be set in stone by the PR framing.
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Most people won’t look at the structure, they’ll just internalize that OpenAI is massively funded.

That effect kicks in well before the money actually does.

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The assumption that's conveniently left out is that the milestones are realistic
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One of the stipulations is that OpenAI achieves "AGI"... Need I say more?

Also a lot of this "money" is in cloud compute and credits not cash so...

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