Subsequent allocation of funds can be friction-free after "account" is setup at particular VC fund. I have heard it someone agreed with their VC on a schedule where money flows one way and shares flow the other way. They have bailed half-way too, since they were doing well enough.
Of course now that you are holding an extra advantage over VCs they will expect higher compensation for their disadvantage, if they know what's good for them.
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Now, if you were asking for infinitely elastic fund, that presents a bigger problem. When you buy things from AWS they know the value of what they get in return - dollars. When you ask for dollars and provide equity in exchange the other party does not know what the value of your proposition is. To assign value requires a lot of labor.
What would work here is some sort of automatic way to establish value of stock. For large companies there exists one. it's called stock marker and its very elastic - you can keep issuing shares as long as you want, until your balance sheet starts looking bad for all the cash you are sitting on (or squandering). Stock markets price the equity based on SEC reports, news and analysts opinions. All of these things cost money and only make sense when such cost can be amortized over large pool of shares.
If the value of shares issued is identical to cost of valuation process the whole thing is wash.
So for this idea to work at minimum process of valuation needs to be (a lot) less expensive than the total stock price itself. Additionally, several VC funds would have to share the cost somehow.
Normally valuation is quite expensive, but if you do it every month maybe it could be less so. In essence, VCs already kind of do it for the companies they invested into. The only problem is that they will not share this information with others.
The extra advantage held over the VCs can be balanced by their ability to cut their losses at any time. Let's say you get $1M/month for 2%/month. If the VC gets cold feet, they can pull out after a few months rather than wait for a long and expensive failure, rather than having to offer $12 Million up front for 24% of what could turn out to be nothing.
Trading ability to cut your losses at 50% of typical investment for inevitability of being cut off at 50% of a hugely successful return will balance out.
However, a hugely successful investment will bail sooner than 50% is reached. Thus the skew is in favor of startup.
Of course the actual negotiation may not take math into account. :-)
This could be good from the entreprenuer's point of view, but would it work for the investors? VCs want to hit home runs so they want to pour loads of cash in and take a big stake. If they minimize (optimize) funding to align with startup's expenditure, they will presumably give up equity - their profit - for cash, which they have loads of. They'll also have more overhang - unless they overcommit and invest in more companies like seats on an airline, which might result in a run on their capital!
From the startup's perspective, there's also the risk of the VC changing their mind with a "we're withdrawing the rest of your funding - sue us if you want, but the lawsuit will last longer than your company can stay in business", which would suck.
I'm thinking in terms of a deal, say, $1m guaranteed funding, withdraw cash as you like, equity will be priced at 5% + 1% per $100k (so the option on $1m is quite expensive). Is there another way it could be structured that would make more sense?
I think a deal like you describe would make a lot of sense... but given the way that VCs are funded, I don't think they'd like it very much. If you've raised X dollars for a fund, and you're already worried about keeping some money in reserve so that you can participate in future funding rounds, the last thing you want is to have even more uncertainty about how much money you have left in the fund.
Of course now that you are holding an extra advantage over VCs they will expect higher compensation for their disadvantage, if they know what's good for them.
.
Now, if you were asking for infinitely elastic fund, that presents a bigger problem. When you buy things from AWS they know the value of what they get in return - dollars. When you ask for dollars and provide equity in exchange the other party does not know what the value of your proposition is. To assign value requires a lot of labor.
What would work here is some sort of automatic way to establish value of stock. For large companies there exists one. it's called stock marker and its very elastic - you can keep issuing shares as long as you want, until your balance sheet starts looking bad for all the cash you are sitting on (or squandering). Stock markets price the equity based on SEC reports, news and analysts opinions. All of these things cost money and only make sense when such cost can be amortized over large pool of shares.
If the value of shares issued is identical to cost of valuation process the whole thing is wash.
So for this idea to work at minimum process of valuation needs to be (a lot) less expensive than the total stock price itself. Additionally, several VC funds would have to share the cost somehow.
Normally valuation is quite expensive, but if you do it every month maybe it could be less so. In essence, VCs already kind of do it for the companies they invested into. The only problem is that they will not share this information with others.
There is opportunity in here somewhere.