Most startups that raise money do it more than once. A typical trajectory might be (1) to get started with a few tens of thousands from something like Y Combinator or individual angels, then (2) raise a few hundred thousand to a few million to build the company, and then (3) once the company is clearly succeeding, raise one or more later rounds to accelerate growth.
Reality can be messier. Some companies raise money twice in phase 2. Others skip phase 1 and go straight to phase 2. And at Y Combinator we get an increasing number of companies that have already raised amounts in the hundreds of thousands. But the three phase path is at least the one about which individual startups' paths oscillate.
This essay focuses on phase 2 fundraising. That's the type the startups we fund are doing on Demo Day, and this essay is the advice we give them.
To founders, the behavior of investors is often opaque—partly because their motivations are obscure, but partly because they deliberately mislead you. And the misleading ways of investors combine horribly with the wishful thinking of inexperienced founders. At YC we're always warning founders about this danger, and investors are probably more circumspect with YC startups than with other companies they talk to, and even so we witness a constant series of explosions as these two volatile components combine.
If you're an inexperienced founder, the only way to survive is by imposing external constraints on yourself. You can't trust your intuitions. I'm going to give you a set of rules here that will get you through this process if anything will. At certain moments you'll be tempted to ignore them. So rule number zero is: these rules exist for a reason. You wouldn't need a rule to keep you going in one direction if there weren't powerful forces pushing you in another.
The ultimate source of the forces acting on you are the forces acting on investors. Investors are pinched between two kinds of fear: fear of investing in startups that fizzle, and fear of missing out on startups that take off. The cause of all this fear is the very thing that makes startups such attractive investments: the successful ones grow very fast. But that fast growth means investors can't wait around. If you wait till a startup is obviously a success, it's too late. To get the really high returns, you have to invest in startups when it's still unclear how they'll do. But that in turn makes investors nervous they're about to invest in a flop. As indeed they often are.
What investors would like to do, if they could, is wait. When a startup is only a few months old, every week that passes gives you significantly more information about them. But if you wait too long, other investors might take the deal away from you. And of course the other investors are all subject to the same forces. So what tends to happen is that they all wait as long as they can, then when some act the rest have to.
Don't raise money unless you want it and it wants you.
The other time not to raise money is when you won't be able to. If you try to raise money before you can
Be in fundraising mode or not.
Because fundraising is so distracting, a startup should either be in fundraising mode or not. And when you do decide to raise money, you should focus your whole attention on it so you can get it done quickly and get back to work.
Investors will try to lure you into fundraising when you're not. It's great for them if they can, because they can thereby get a shot at you before everyone else. They'll send you emails saying they want to meet to learn more about you. If you get cold-emailed by an associate at a VC firm, you shouldn't meet even if you are in fundraising mode. Deals don't happen that way.
Get introductions to investors.
Do you have to be introduced? In phase 2, yes. Some investors will let you email them a business plan, but you can tell from the way their sites are organized that they don't really want startups to approach them directly.
Intros vary greatly in effectiveness. The best type of intro is from a well-known investor who has just invested in you. So when you get an investor to commit, ask them to introduce you to other investors they respect.
There are now sites like AngelList, FundersClub, and WeFunder that can introduce you to investors. We recommend startups treat them as auxiliary sources of money. Raise money first from leads you get yourself. Those will on average be better investors. Plus you'll have an easier time raising money on these sites once you can say you've already raised some from well-known investors.
Hear no till you hear yes.
I mentioned earlier that investors prefer to wait if they can. What's particularly dangerous for founders is the way they wait. Essentially, they lead you on. They seem like they're about to invest right up till the moment they say no. If they even say no. Some of the worse ones never actually do say no; they just stop replying to your emails. They hope that way to get a free option on investing. If they decide later that they want to invest—usually because they've heard you're a hot deal—they can pretend they just got distracted and then restart the conversation as if they'd been about to.
Do breadth-first search weighted by expected value.
Know where you stand.
Never leave a meeting with an investor without asking what happens next. What more do they need in order to decide? Do they need another meeting with you? To talk about what? And how soon? Do they need to do something internally, like talk to their partners, or investigate some issue? How long do they expect it to take? Don't be too pushy, but know where you stand. If investors are vague or resist answering such questions, assume the worst; investors who are seriously interested in you will usually be happy to talk about what has to happen between now and wiring the money, because they're already running through that in their heads.
Getting the first substantial offer can be half the total difficulty of fundraising. What counts as a substantial offer depends on who it's from and how much it is. Money from friends and family doesn't usually count, no matter how much. But if you get $50k from a well known VC firm or angel investor, that will usually be enough to set things rolling.
Inexperienced investors are the ones most likely to get buyer's remorse. Established ones have learned to treat saying yes as like diving off a diving board, and they also have more brand to preserve. But I've heard of cases of even top-tier VC firms welching on deals.
Avoid investors who don't "lead."
Conversely, an investor who will only invest once other investors have is worthless initially. And while most investors are influenced by how interested other investors are in you, there are some who have an explicit policy of only investing after other investors have. You can recognize this contemptible subspecies of investor because they often talk about "leads." They say that they don't lead, or that they'll invest once you have a lead. Sometimes they even claim to be willing to lead themselves, by which they mean they won't invest till you get $x from other investors. (It's great if by "lead" they mean they'll invest unilaterally, and in addition will help you raise more. What's lame is when they use the term to mean they won't invest unless you can raise more elsewhere.)
Series A rounds still work that way, but things now work differently for most fundraising prior to the series A. Now there are rarely actual rounds before the A round, or leads for them. Now startups simply raise money from investors one at a time till they feel they have enough.
Since there are no longer leads, why do investors use that term? Because it's a more legitimate-sounding way of saying what they really mean. All they really mean is that their interest in you is a function of other investors' interest in you. I.e. the spectral signature of all mediocre investors. But when phrased in terms of leads, it sounds like there is something structural and therefore legitimate about their behavior.
When an investor tells you "I want to invest in you, but I don't lead," translate that in your mind to "No, except yes if you turn out to be a hot deal." And since that's the default opinion of any investor about any startup, they've essentially just told you nothing.
When you first start fundraising, the expected value of an investor who won't "lead" is zero, so talk to such investors last if at all.
Have multiple plans.
So why do investors ask how much you plan to raise? For much the same reasons a salesperson in a store will ask "How much were you planning to spend?" if you walk in looking for a gift for a friend. You probably didn't have a precise amount in mind; you just want to find something good, and if it's inexpensive, so much the better. The salesperson asks you this not because you're supposed to have a plan to spend a specific amount, but so they can show you only things that cost the most you'll pay.
Similarly, when investors ask how much you plan to raise, it's not because you're supposed to have a plan. It's to see whether you'd be a suitable recipient for the size of investment they like to make, and also to judge your ambition, reasonableness, and how far you are along with fundraising.
If you're a wizard at fundraising, you can say "We plan to raise a $7 million series A round, and we'll be accepting termsheets next tuesday." I've known a handful of founders who could pull that off without having VCs laugh in their faces. But if you're in the inexperienced but earnest majority, the solution is analogous to the solution I recommend for
And the right strategy, in fundraising, is to have multiple plans depending on how much you can raise. Ideally you should be able to tell investors something like: we can make it to profitability without raising any more money, but if we raise a few hundred thousand we can hire one or two smart friends, and if we raise a couple million, we can hire a whole engineering team, etc.
Different plans match different investors. If you're talking to a VC firm that only does series A rounds (though there are few of those left), it would be a waste of time talking about any but your most expensive plan. Whereas if you're talking to an angel who invests $20k at a time and you haven't raised any money yet, you probably want to focus on your least expensive plan.
If you're so fortunate as to have to think about the upper limit on what you should raise, a good rule of thumb is to multiply the number of people you want to hire times $15k times 18 months. In most startups, nearly all the costs are a function of the number of people, and $15k per month is the conventional total cost (including benefits and even office space) per person. $15k per month is high, so don't actually spend that much. But it's ok to use a high estimate when fundraising to add a margin for error. If you have additional expenses, like manufacturing, add in those at the end. Assuming you have none and you think you might hire 20 people, the most you'd want to raise is 20 x $15k x 18 = $5.4 million.
For example, if you'd like to raise $500k, it's better to say initially that you're trying to raise $250k. Then when you reach $150k you're more than half done. That sends two useful signals to investors: that you're doing well, and that they have to decide quickly because you're running out of room. Whereas if you'd said you were raising $500k, you'd be less than a third done at $150k. If fundraising stalled there for an appreciable time, you'd start to read as a failure.
Saying initially that you're raising $250k doesn't limit you to raising that much. When you reach your initial target and you still have investor interest, you can just decide to raise more. Startups do that all the time. In fact, most startups that are very successful at fundraising end up raising more than they originally intended.
I'm not saying you should lie, but that you should lower your expectations initially. There is almost no downside in starting with a low number. It not only won't cap the amount you raise, but will on the whole tend to increase it.
A good metaphor here is angle of attack. If you try to fly at too steep an angle of attack, you just stall. If you say right out of the gate that you want to raise a $5 million series A round, unless you're in a very strong position, you not only won't get that but won't get anything. Better to start at a low angle of attack, build up speed, and then gradually increase the angle if you want.
Be profitable if you can.
There are many analogies between fundraising and dating, and this is one of the strongest. No one wants you if you seem desperate. And the best way not to seem desperate is not to
There are almost two distinct modes of fundraising: one in which founders who need money knock on doors seeking it, knowing that otherwise the company will die or at the very least people will have to be fired, and one in which founders who don't need money take some to grow faster than they could merely on their own revenues. To emphasize the distinction I'm going to name them: type A fundraising is when you don't need money, and type B fundraising is when you do.
Inexperienced founders read about famous startups doing what was type A fundraising, and decide they should raise money too, since that seems to be how startups work. Except when they raise money they don't have a clear path to profitability and are thus doing type B fundraising. And they are then surprised how difficult and unpleasant it is.
Of course not all startups can make it to ramen profitability in a few months. And some that don't still manage to have the upper hand over investors, if they have some other advantage like extraordinary growth numbers or exceptionally formidable founders. But as time passes it gets increasingly difficult to fundraise from a position of strength without being profitable.
Founders who raise money at high valuations tend to be unduly proud of it. Founders are often competitive people, and since valuation is usually the only visible number attached to a startup, they end up competing to raise money at the highest valuation. This is stupid, because fundraising is not the test that matters. The real test is revenue. Fundraising is just a means to that end. Being proud of how well you did at fundraising is like being proud of your college grades.
Not only is fundraising not the test that matters, valuation is not even the thing to optimize about fundraising. The number one thing you want from phase 2 fundraising is to get the money you need, so you can get back to focusing on the real test, the success of your company. Number two is good investors. Valuation is at best third.
The empirical evidence shows just how unimportant it is. Dropbox and Airbnb are the most successful companies we've funded so far, and they raised money after Y Combinator at premoney valuations of $4 million and $2.6 million respectively. Prices are so much higher now that if you can raise money at all you'll probably raise it at higher valuations than Dropbox and Airbnb. So let that satisfy your competitiveness. You're doing better than Dropbox and Airbnb! At a test that doesn't matter.
When you start fundraising, your initial valuation (or valuation cap) will be set by the deal you make with the first investor who commits. You can increase the price for later investors, if you get a lot of interest, but by default the valuation you got from the first investor becomes your asking price.
So if you're raising money from multiple investors, as most companies do in phase 2, you have to be careful to avoid raising the first from an over-eager investor at a price you won't be able to sustain. You can of course lower your price if you need to (in which case you should give the same terms to investors who invested earlier at a higher price), but you may lose a bunch of leads in the process of realizing you need to do this.
What you can do if you have eager first investors is raise money from them on an uncapped convertible note with an MFN clause. This is essentially a way of saying that the valuation cap of the note will be determined by the next investors you raise money from.
It will be easier to raise money at a lower valuation. It shouldn't be, but it is. Since phase 2 prices vary at most 10x and the big successes generate returns of at least 100x, investors should pick startups entirely based on their estimate of the probability that the company will be a big success and hardly at all on price. But although it's a mistake for investors to care about price, a significant number do. A startup that investors seem to like but won't invest in at a cap of $x will have an easier time at $x/2.
Fortunately there is a way to avoid naming a price in this situation. And it is not just a negotiating trick; it's how you (both) should be operating. Tell them that valuation is not the most important thing to you and that you haven't thought much about it, that you are looking for investors you want to partner with and who want to partner with you, and that you should talk first about whether they want to invest at all. Then if they decide they do want to invest, you can figure out a price. But first things first.
Since valuation isn't that important and getting fundraising rolling is, we usually tell founders to give the first investor who commits as low a price as they need to. This is a safe technique so long as you combine it with the next one.
Ideally you know which investors have a reputation for being "valuation sensitive" and can postpone dealing with them till last, but occasionally one you didn't know about will pop up early on. The rule of doing breadth first search weighted by expected value already tells you what to do in this case: slow down your interactions with them.
There are a handful of investors who will try to invest at a lower valuation even when your price has already been set. Lowering your price is a backup plan you resort to when you discover you've let the price get set too high to close all the money you need. So you'd only want to talk to this sort of investor if you were about to do that anyway. But since investor meetings have to be arranged at least a few days in advance and you can't predict when you'll need to resort to lowering your price, this means in practice that you should approach this type of investor last if at all.
If you're surprised by a lowball offer, treat it as a backup offer and delay responding to it. When someone makes an offer in good faith, you have a moral obligation to respond in a reasonable time. But lowballing you is a dick move that should be met with the corresponding countermove.
Accept offers greedily.
If someone makes you an acceptable offer, take it. If you have multiple incompatible offers, take the best. Don't reject an acceptable offer in the hope of getting a better one in the future.
These simple rules cover a wide variety of cases. If you're raising money from many investors, roll them up as they say yes. As you start to feel you've raised enough, the threshold for acceptable will start to get higher.
In practice offers exist for stretches of time, not points. So when you get an acceptable offer that would be incompatible with others (e.g. an offer to invest most of the money you need), you can tell the other investors you're talking to that you have an offer good enough to accept, and give them a few days to make their own. This could lose you some that might have made an offer if they had more time. But by definition you don't care; the initial offer was acceptable.
Some investors will try to prevent others from having time to decide by giving you an "exploding" offer, meaning one that's only valid for a few days. Offers from the very best investors explode less frequently and less rapidly—Fred Wilson never gives exploding offers, for example—because they're confident you'll pick them. But lower-tier investors sometimes give offers with very short fuses, because they believe no one who had other options would choose them. A deadline of three working days is acceptable. You shouldn't need more than that if you've been talking to investors in parallel. But a deadline any shorter is a sign you're dealing with a sketchy investor. You can usually call their bluff, and you may need to.
(The situation is different in phase 1. You can't apply to all the incubators in parallel, because some offset their schedules to prevent this. In phase 1, "accept offers greedily" and "get the best investors" do conflict, so if you want to apply to multiple incubators, you should do it in such a way that the ones you want most decide first.)
Sometimes when you're raising money from multiple investors, a series A will emerge out of those conversations, and these rules even cover what to do in that case. When an investor starts to talk to you about a series A, keep taking smaller investments till they actually give you a termsheet. There's no practical difficulty. If the smaller investments are on convertible notes, they'll just convert into the series A round. The series A investor won't like having all these other random investors as bedfellows, but if it bothers them so much they should get on with giving you a termsheet. Till they do, you don't know for sure they will, and the greedy algorithm tells you what to do.
Our rule of thumb is not to sell more than 25% in phase 2, on top of whatever you sold in phase 1, which should be less than 15%. If you're raising money on uncapped notes, you'll have to guess what the eventual equity round valuation might be. Guess conservatively.
(Since the goal of this rule is to avoid messing up the series A, there's obviously an exception if you end up raising a series A in phase 2, as a handful of startups do.)
Have one person handle fundraising.
The founder who handles fundraising should be the CEO, who should in turn be the most formidable of the founders. Even if the CEO is a programmer and another founder is a salesperson? Yes. If you happen to be that type of founding team, you're effectively a single founder when it comes to fundraising.
It's ok to bring all the founders to meet an investor who will invest a lot, and who needs this meeting as the final step before deciding. But wait till that point. Introducing an investor to your cofounder(s) should be like introducing a girl/boyfriend to your parents—something you do only when things reach a certain stage of seriousness.
Even if there are still one or more founders focusing on the company during fundraising, growth will slow. But try to get as much growth as you can, because fundraising is a segment of time, not a point, and what happens to the company during that time affects the outcome. If your numbers grow significantly between two investor meetings, investors will be hot to close, and if your numbers are flat or down they'll start to get cold feet.
You'll need an executive summary and (maybe) a deck.
I say "traditionally" because I'm ambivalent about decks, and (though perhaps this is wishful thinking) they seem to be on the way out. A lot of the most successful startups we fund never make decks in phase 2. They just talk to investors and explain what they plan to do. Fundraising usually takes off fast for the startups that are most successful at it, and they're thus able to excuse themselves by saying that they haven't had time to make a deck.
You'll also want an executive summary, which should be no more than a page long and describe in the most matter of fact language what you plan to do, why it's a good idea, and what progress you've made so far. The point of the summary is to remind the investor (who may have met many startups that day) what you talked about.
Assume that if you give someone a copy of your deck or executive summary, it will be passed on to whoever you'd least like to have it. But don't refuse on that account to give copies to investors you meet. You just have to treat such leaks as a cost of doing business. In practice it's not that high a cost. Though founders are rightly indignant when their plans get leaked to competitors, I can't think of a startup whose outcome has been affected by it.
Sometimes an investor will ask you to send them your deck and/or executive summary before they decide whether to meet with you. I wouldn't do that. It's a sign they're not really interested.
Stop fundraising when it stops working.
It's hard to give general advice about this, because there have been cases of startups that kept trying to raise money even when it seemed hopeless, and miraculously succeeded. But what I usually tell founders is to stop fundraising when you start to get a lot of air in the straw. When you're drinking through a straw, you can tell when you get to the end of the liquid because you start to get a lot of air in the straw. When your fundraising options run out, they usually run out in the same way. Don't keep sucking on the straw if you're just getting air. It's not going to get better.
Don't get addicted to fundraising.
When I see a startup with young founders that is fabulously successful at fundraising, I mentally decrease my estimate of the probability that they'll succeed. The press may be writing about them as if they'd been anointed as the next Google, but I'm thinking "this is going to end badly."
Don't raise too much.
A company's valuation is expected to rise each time it raises money. If not it's a sign of a company in trouble, which makes you unattractive to investors. So if you raise money in phase 2 at a post-money valuation of $30 million, the pre-money valuation of your next round, if you want to raise one, is going to have to be at least $50 million. And you have to be doing really, really well to raise money at $50 million.
It's very dangerous to let the competitiveness of your current round set the performance threshold you have to meet to raise your next one, because the two are only loosely coupled.
But the money itself may be more dangerous than the valuation. The more you raise, the more you spend, and spending a lot of money can be disastrous for an early stage startup. Spending a lot makes it harder to become profitable, and perhaps even worse, it makes you more rigid, because the main way to spend money is people, and the more people you have, the harder it is to change directions. So if you do raise a huge amount of money, don't spend it. (You will find that advice almost impossible to follow, so hot will be the money burning a hole in your pocket, but I feel obliged at least to try.)
It's a mistake to behave arrogantly to investors. While there are certain situations in which certain investors like certain kinds of arrogance, investors vary greatly in this respect, and a flick of the whip that will bring one to heel will make another roar with indignation. The only safe strategy is never to seem arrogant at all.
That will require some diplomacy if you follow the advice I've given here, because the advice I've given is essentially how to play hardball back. When you refuse to meet an investor because you're not in fundraising mode, or slow down your interactions with an investor who moves too slow, or treat a contingent offer as the no it actually is and then, by accepting offers greedily, end up leaving that investor out, you're going to be doing things investors don't like. So you must cushion the blow with soft words. At YC we tell startups they can blame us. And now that I've written this, everyone else can blame me if they want. That plus the inexperience card should work in most situations: sorry, we think you're great, but PG said startups shouldn't ___, and since we're new to fundraising, we feel like we have to play it safe.
The danger of behaving arrogantly is greatest when you're doing well. When everyone wants you, it's hard not to let it go to your head. Especially if till recently no one wanted you. But restrain yourself. The startup world is a small place, and startups have lots of ups and downs. This is a domain where it's more true than usual that pride goeth before a fall.
The bar will be higher next time.
Over the past several years, the investment community has evolved from a strategy of anointing a small number of winners early and then supporting them for years to a strategy of spraying money at early stage startups and then ruthlessly culling them at the next stage. This is probably the optimal strategy for investors. It's too hard to pick winners early on. Better to let the market do it for you. But it often comes as a surprise to startups how much harder it is to raise money in phase 3.
When your company is only a couple months old, all it has to be is a promising experiment that's worth funding to see how it turns out. The next time you raise money, the experiment has to have worked. You have to be on a trajectory that leads to going public. And while there are some ideas where the proof that the experiment worked might consist of e.g. query response times, usually the proof is profitability. Usually phase 3 fundraising has to be type A fundraising.
In practice there are two ways startups hose themselves between phases 2 and 3. Some are just too slow to become profitable. They raise enough money to last for two years. There doesn't seem any particular urgency to be profitable. So they don't make any effort to make money for a year. But by that time, not making money has become habitual. When they finally decide to try, they find they can't.
The other way companies hose themselves is by letting their expenses grow too fast. Which almost always means hiring too many people. You usually shouldn't go out and hire 8 people as soon as you raise money at phase 2. Usually you want to wait till you have growth (and thus usually revenues) to justify them. A lot of VCs will encourage you to hire aggressively. VCs generally tell you to spend too much, partly because as money people they err on the side of solving problems by spending money, and partly because they want you to sell them more of your company in subsequent rounds. Don't listen to them.
Don't make things complicated.
Fundraising is not what will make you successful. It's just a means to an end. Your primary goal should be to get it over with and get back to what will make you successful—making things and talking to users—and the path I've described will for most startups be the surest way to that destination.
Be good, take care of yourselves, and
(Not all unpromising-seeming startups do badly. Some are merely ugly ducklings in the sense that they violate current startup fashions.)
It's ok to talk to an associate if you get an intro to a VC firm or they see you at a Demo Day and they begin by having an associate vet you. That's not a promising lead and should therefore get low priority, but it's not as completely worthless as a cold email.
Because the title "associate" has gotten a bad reputation, a few VC firms have started to give their associates the title "partner," which can make things very confusing. If you're a YC startup you can ask us who's who; otherwise you may have to do some research online. There may be a special title for actual partners. If someone speaks for the firm in the press or a blog on the firm's site, they're probably a real partner. If they're on boards of directors they're probably a real partner.
There are titles between "associate" and "partner," including "principal" and "venture partner." The meanings of these titles vary too much to generalize.
Don't ask investors who say no for introductions to other investors. That will in many cases be an anti-recommendation.
Some founders deliberately schedule a handful of lame investors first, to get the bugs out of their pitch.
Investors are fine with funding nerds. So if you're a nerd, just try to be a good nerd, rather than doing a bad imitation of a smooth salesman.
If you have the luxury of choosing among seed investors, you can play it safe by excluding VC firms. But it isn't critical to.
You can relent a little if the potential series A investor has a great reputation and they're clearly working fast to get you a termsheet, particularly if a third party like YC is involved to ensure there are no misunderstandings. But be careful.