Raise less money

Over the last few years, I’ve noticed that good companies are increasingly over-diluting themselves in their seed and A rounds. Counterintuitively, dilution seems to rise along with price. One would expect the opposite correlation. Strong founders who command high prices should be using that higher price to sell less of their companies in exchange for money to grow. As I’ve tried to understand what’s going on, I’ve tried several arguments.

Somewhere in the last week, I’ve come to understand an error I’ve been making when talking to founders about how much money to raise. I realized that the conversation about raising always anchors back to the idea of adding “months of runway.” That always seemed appropriate to me because it was a measure of the amount of time a company had to stay alive. Staying alive seemed good since it increased the time a company had to find product market fit and to grow.

But I now realize that this is the wrong framing because simply staying alive is an inadequate goal for a company.  Founders start companies to find product market fit and grow. Venture capital is designed to speed growth, not to extend runway.

As a result, in recent conversations, I’ve started to ask founders: “How much could you get done in the next 12 months with the amount of capital you are planning to raise? If you’re a good company, you’re either going to raise your Series A - or Series B - in the next 12 months or have significant revenue such that you won’t need more capital.[1] If you’re doing badly, why would you want to keep working on this for 24 or 36 months? That’s a waste of your time.”

Founders who raise too much capital are acting out of fear rather than acting out of confidence. This fear made sense ten years ago when seed financing was relatively scarce. This is when much of the fundraising advice I read as a founder was written. However, the world has changed and so should the advice

Financing is more accessible to good founders than it has ever been.[2] Confident, competent founders should take the risk of running out of money vs. the certainty of over-dilution.

Good founders respond to this framework as it shifts the argument from one in which “winning” is about adding months of runway to the bank to one in which “winning” is fast and high quality execution - as evidenced by hitting milestones. It’s also easy to draw a straight line from this framing to the best companies. When a company raises a Series A nine months after launch - or Demo Day - with 80% of its seed funds in the bank, it’s apparent that those founders sold too much.[3]

A founder’s decision on how much money to raise in any given round is more art than science. It is a fraught decision since it necessarily forces founders to make predictions about the future. There is no perfect answer, and over-optimizing around any single factor is a mistake. However, it seems clear that shifting the goal of fundraising from adding runway to progress would limit both the amount of money companies believe they need and the dilution that founders take in the process of building successful startups.

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[1] And if this is true, investors will chase you anyway.

[2] Even during COVID. I did not expect this to be true, however, this market is one of the most active I've ever seen.

[3] Seeing this dynamic on a regular basis while running YC's Series A program is what led me to realize my mistake. Without fail, the founders raising the most competitive rounds have the most capital left, and thereby the most unnecessary dilution.

Thank you to Daniel Gackle and Michael Seibel for your thoughts and edits.

Asking questions

Small children are great at asking questions. Their questions are simple, direct, and utterly without ego. If you spend time with 2-5 year olds, you’ll find yourself answering a near infinite series of progressively more challenging questions. This is one of the main paths by which children learn about the world.

ex. Child question: “Why is the sky blue?”


Adults are generally bad at asking questions. Adult questions come with long preambles, caveats, and agendas. Adult questions don’t seem to be designed to learn about the world, they seem to be designed to avoid looking dumb.

ex. Adult question: “I know the sky isn’t actually blue, and that if I look up, I know there’s nothing between me and outer space except air and maybe some clouds. Beyond that, there’s outer space. Outer space is effectively black because there isn’t light. Yet the sky often, though not always, appears to be various shades of blue. What triggers that blue? Is it something about how light interacts with air? Or gravity? Magnetic fields?”

The contrast between child questions and adult questions is striking, but it isn’t a function of age, it’s a function of conditioning. At some point, children get social signals that asking questions makes them appear stupid. This can come from a frustrated parent, annoyed teacher, or mocking friend.

Kids internalize this feedback and start to ask fewer questions as they grow up. The scope of things about which adults ask questions get narrower and narrower, shying away from things that are new or hard to understand. At the same time, adult questions get longer and longer. Most of this length isn’t important for the question, it is meant to prevent the audience from thinking the questioner is stupid.

These questions aren’t terribly useful to either the questioner or the questionee. If you’re not sure what this type of question looks like, watch a congressional hearing. The questions are meant to prove points, not produce knowledge.

Adult questions reinforce their own badness. When an adult spends most of a question proving his own intelligence, the question doesn’t produce new knowledge. This reinforces the perception that questions aren’t worth practicing. Without that practice, the questions continue to get worse.

I’ve been thinking about questions because I noticed that I’ve become increasingly self conscious about not knowing things, and cover for that by asking adult questions. Some of this is a function of the fact that I’m older and some of it is a function of the fact that my job involves giving a significant amount of advice. I noticed, as well, that conversations in which I ask simpler questions are more enjoyable and more interesting. These conversations lead to new ideas and better plans.

I’m particularly conscious of this dynamic in conversations with founders. Many founders believe that adult questions are the best questions because of their interactions with investors. On the one hand, investors tell founders that asking questions is a good thing. On the other hand, founders are judged for asking questions that are “too basic.” Founders who do things without asking questions first are generally rewarded for being “fast” whereas those that ask some questions first are derided as being “slow.”

However, successful startups are not defined by the questions that a founder asks. They are defined by what a founder does with the information at hand, and how quickly. Founders who acquire new information quickly and act are more successful. Founders who dither or get caught in infinite loops of ignorant execution generally fail.

Founders and investors would have better conversations if each side dropped the pretense of needing to “look” smart and asked child questions. This isn’t a complex task, but it does require focus.

The way I’m working on this is to stop myself each time I’m about to ask a question and figure out what I actually want to know, and then see if I can just ask that specific question in no more than a single simple sentence. If the question does not produce a satisfying answer, I’ll try to understand if it is because I worded the question poorly, or did not provide enough context. If I need more context, I’ll add one or two sentences of context, and ask the question again.

This strategy does not always work: I don’t always catch myself in time, I sometimes ask poorly worded questions, sometimes the question requires more context than is practical. However, I’ve found that the act of thinking about the question I want to ask and examining it in this child/adult dichotomy has helped me ask better questions, have better conversations, and learn more things. That’s enough of a reason to continue doing it.

Fooled by experts

Experts are generally right until they're wrong. Unfortunately, it's very easy to get fooled into thinking that experts are always right. This is because they are...experts. They are authoritative and knowledgeable. This is especially true when it comes to trying new things in existing fields. We are biased into believing that knowing a lot about something confers an ability to predict the future.

The problem with expertise is that it doesn't necessarily come paired with an openness to new ideas. Expertise can be used to shut down new ideas and avenues of exploration just as easily as it can aid in invention. I've been guilty of this when hearing about new ideas. In fact, it often feels easier to shut things down than to use what I know to figure out how to make something new actually work.[1] Perversely, being negative may make someone seem like more of an expert than they are, creating a negative feedback cycle.

When you don't know much about a subject, you're free of the constraints of what has been tried. That means people who are inexpert will often have wilder ideas. Sometimes, that's called naive or stupid. However, when those ideas happen to work, then it's called genius or groundbreaking.

That doesn't mean that every problem can be solved by creative ignoramuses. There seems to be a level of expertise which, when paired with the right environment, is conducive to productive creativity. I wish I had a way to know those levels for different areas.

Without a clear set of rules to use in evaluating expertise, I instead try to evaluate founders based on what I can learn from talking to them. This is especially true in areas that I understand fairly well. While there are certain things I might expect a founder to understand about what they're doing, I'm much more interested in how they think and test assumptions. This is part of how I try to figure out if I'm investing in potential (good) or track record (not so good).

One of the tricks in doing this is to see whether or not the tests that founders run cause them to ask increasingly interesting questions. Coming up with questions is a good sign of creativity, while answering them well builds the expertise necessary to actually get something done.

Technology increases the likelihood that a seemingly naive approach to a problem will work because it reduces the iterative cycle of trying that approach. Given enough time and resources, you could try every single solution[2]. In the real world, though, we have to pick solutions to work on. This is where the good founders are separated from the bad ones. The good ones get better and more open as time goes on, while the bad ones get more closed down and start rejecting ideas out of hand.

The same is true for investors. The best ones use new knowledge to open up new ideas, while the worst use it to close out entire categories of ideas.[3] That's short sighted because the world constantly changes, which makes new things possible. Founding and an investing in those new possibilities is what creates the companies that change the world. That creates new areas in which to be expert, starting the cycle all over again.

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[1] https://archive.org/stream/ERIC_ED211573#page/n0/mode/2up

[2] And enough monkeys at enough typewriters will eventually produce Hamlet.

[3] This is different than investors who understand the limits of their expertise and focus on specific sectors. An investor can be sector focused and open to lots of new ideas within that sector, just as an investor can say they'll invest in anything only to shoot down every idea.

Thanks to Craig Cannon for feedback.

Why VCs sometimes push companies to burn

Originally posted on the YC blog, here: https://blog.ycombinator.com/why-vcs-sometimes-push-companies-to-burn-too-fast/

In Investors and their incentives, I tried to give a broad breakdown of the incentives that drive the major types of startup investors. I want to dig deeper into a behavior that VCs sometimes exhibit which seems strange from the point of view of founders. Despite praising frugality, VCs sometimes push companies to spend more money, faster. Sometimes this leads to faster growth. More often it leads to empty bank accounts. I've seen a number of companies get killed by this dynamic, and it took me a long time to understand why it happens.

Misaligned Incentives

Though VC firms generally act in ways that they believe are most likely to help a company succeed, their incentives can become misaligned around questions of burn because of uncertainty and time. Since VCs know that most of their returns come from a very small number of bets, they need individual partners to spend large amounts of time with the companies that they've funded. That time is required to help (in the best scenarios) and to figure out which bet is actually worth further investment of time and capital. In an ideal world, VC firms would be able to increase partners and investing capital whenever they want to add investments. That would, however, require infinite accessible capital and ever larger partnerships. The first doesn't exist and the second would be hard to manage and support.

Funds are also under pressure to produce returns within a given timeframe in order to demonstrate quality for raising further funds. These capital raises are important because many VCs make more off of management fees than they do from investing well.[1] The most important thing for the near and medium term success of a firm is its ability to generate more fees. With an average fund life for early stage investors of 10 years - and a pattern of raising a new fund every 2-4 years - VCs must show some kind of progress. There is rarely enough time for a firm to return capital to LPs before raising a new fund, so they use private valuations to mark their portfolios up or down. If a fund can show a material markup, they have an edge in marketing for their capital raise. While funds that don't produce meaningful returns to investors generally fail after a while, it takes a really long time for that to happen.

Combining these two incentives creates a situation in which it is better for a VC firm to push a company to demonstrate success or failure quickly rather than move more slowly. Companies that succeed quickly lower the uncertainty involved in investing further in that company, and justify the amount of time spent by an individual partner on that investment. If a company is doing well it is also likely to attract new investments at higher valuations, which allows the firm to mark up its investment.

Conversely, companies that fail remove themselves as a time commitment for a partner. That's not an ideal outcome, but it means that the VC firm can refocus energy on companies that are doing well and on finding new companies to make up the valuation lost through the failure of one piece of the portfolio. The faster this happens, the better for the investor.

The worst situation for a VC is one in which the firm has made a significant investment in a company that just muddles along, constantly threatening success and failure. These companies require a lot of time and effort to figure out whether or not they can be saved. They generally generate significant team drama which investors sometimes mediate. They often present difficult bridge financing questions, and they rarely function as good marketing fodder.

How Founders Should Respond

Figuring out how to deal with these pressures is important, and varies depending on your relationship with your investor. The most important thing to remember is that the CEO controls the bank account. Investors can pressure founders to spend faster, but they cannot force them to do so. Founders need to have their own understanding of where and when to spend money, and what rate of spending makes sense.

Next, remember that promises of more funding made when things are going well aren't worth much. All that matters is the money currently in your bank account. It can be easy, during heady days of growth, to justify any and all expenditures. I've talked to founders who have done just that, saying that they need to hire more engineers to develop new features for new users or that they need to spend on advertising to ramp up acquisition. Invariably, they talk about how investor x or y told them that they're special and had promised to keep funding them no matter what. Investors will often point to the burn at successful companies like Uber to prove that spending is good. Founders will sometimes accept this logic without thinking deeply enough about whether or not the lesson applies to their own situations.[2] A company can get away with this so long as growth is working, but as soon as that company goes sideways, spending becomes problematic.[3]

The closer your company edges towards “not likely to return a meaningful part of the fund,” the faster investor capital will dry up, no matter the promises made early on. This is where investor incentives diverge from those of the company. As the investor gets surer that the company will fail, the investor usually pulls back. As the founder gets closer to failure, the founder's need for active engagement and help grows. This mismatch can kill companies and relationships.

It may not be surprising, then, that the more money a founder has in the bank, the stronger their position when fundraising. In fact, we've seen a few YC companies raise financing rounds without having spent any of the money from a prior round. They do this because they get offered very friendly terms. They can do this because they've figured out how to grow without spending lots of money.

The Second-Worst Case

When incentives start to diverge, one of two things can happen. The first case is a bit better, though not great for the founders. There are times where the VC will see a failing company and decide that success is still possible. When this happens, the VC may invest more into the company but will only do so on terms materially more favorable to the investor than would otherwise be the case. This results in significant loss of control and equity for the founder, and may involve the founder being replaced. Whether or not this happens depends on how much leverage the founder has left, and as a bank account approaches 0, leverage decreases asymptotically.

Still, the company may survive.

The Worst Case

The company runs out of money.
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[1] https://hbr.org/2014/08/venture-capitalists-get-paid-well-to-lose-money
[2] I addressed a bit of this here: http://www.aaronkharris.com/exceptionalism
[3] My partner, Dalton Caldwell, wrote a great post about what you should do if you find yourself in this situation: http://www.themacro.com/articles/2016/01/advice-startups-running-out-of-money/.

Thanks to Craig Cannon, Paul Buchheit and Dalton Caldwell for your edits. Thanks to Paul Graham for initially explaining this dynamic.

Fundraising isn't predictable

I recently had a conversation with a founder who'd just finished a number of unsatisfying conversations with investors. The founder's company was growing well, had crossed $1mm ARR, but still couldn't raise money. According to conventional wisdom, that should have been enough to open some checkbooks. Unfortunately, that's not how fundraising works.

This is strange because of the way we generally talk about startups. In attempting to set up the kinds of experiments on which startups are built, we tend to put precise milestones in place to gauge results. This is great when measuring progress, but it implies a false sense of precision with regard to raising money.

I've started borrowing a concept from insurance to frame this problem: Parametric triggers. Parametric triggers are a tool used by insurance companies to govern payouts from policies. These triggers remove subjectivity from the claims process by using independently verifiable, empirical evidence as the decision tree for claims.[1] Applying this concept to fundraising would mean that there is a precise set of things a startup could do to get funding. That's how we'd all like it to work, but there are no specific events that will automatically get money from an investor.

In reality, fundraising happens for companies under a ranged set of conditions. Those ranges and the accompanying outcomes are generally different for different companies, or even for the same company at different times. To make matters even trickier, those ranges are only apparent in hindsight when looking at aggregate information about a large number of deals. What those ranges don't tell you is where the actually successful companies sat in those ranges.

This dynamic is apparent in the aftermath of Demo Day at YC. If you were to isolate on a single characteristic of companies within a batch (say, revenue), you'd find companies with impressive revenue growth failing to raise capital, and ones without much revenue raising significant capital. In a parametric world, this wouldn't happen.

The reason this does happen is that parametric triggers are a great tool for deciding what to do about something that happened in the past. In insurance, parametric triggers determine a specific payout for a specific event - an earthquake of 4.7 magnitude will pay a policy, while one of 4.6 will not. Parametric insurance doesn't account for costs after the event or the payout. The system has all the information it needs to make a decision at the decision point.

Investing in startups isn't about what has happened. Investing in startups is about what will happen. Investors are trying to find small companies that will become multibillion dollar ones. They use past performance as an indication of the quality of the founders and the idea, but no metric is a perfect predictor of the future. The ranged conditions that investors often use as filters - i.e. 15-20% growth per month for SAAS companies [2] - are useful tools to use when sorting for worthwhile conversations given limited time. Those filters are never sufficient for actually making an investment, and every investor has a different framework for making that final decision.

When investors turn down a deal, the good ones will give the founders at least one reason. This may take the form of “we don't understand how you can scale,” “we think there are too many competitors,” or “we don't think you're growing fast enough.” While it is important to think about the reasons given, never assume that the only thing between you and the investment is proving that you can solve for that condition.

What you actually need to do is figure out what pieces of evidence you can use to create a future for your company that investors would be foolish to ignore. This will likely require some mix of your traction, the market you are attacking, and how impressive you and your team are. You also need to recognize that there are contra-indicators of success which investors have been trained to recognize. If they see a small ultimate market with no adjacencies, then incredible early growth has no chance of producing a big company, so they will pass.

Much has been written on how to pitch and fundraise, which is part of the problem. Founders are drowning in examples that seek to turn fundraising into a deterministic process. Accepting that it isn't is a counterintuitive and critical lesson in fundraising successfully.

Here are examples of meaningful achievements that won't automatically get you funded but will get an investor's attention and can be used as part of the story you tell:
  • $1mm ARR
  • 10% weekly growth
  • Repeat founders who were previously funded
  • 2 Fortune 500 pilots, 5 in pipeline
  • Engagement rates that are higher than Facebook

Fundraising is a frustrating process that resists well-meaning attempts to make it into a predictable science. That's actually quite fitting, though, since while much about startups can be measured, that measurement never guarantees success. Success comes from using the unique advantages you have and combining them into a coherent, self-reinforcing story and product.
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[1] https://www.wikiwand.com/en/Parametric_insurance
[2] http://tomtunguz.com/mrr-growth/

Thanks to Craig Cannon, Dalton Caldwell, Sam Altman, and Andy Weissman for your edits.