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Moneyball for Tech Startups

March 1, 2025

Michael Lewis’s Moneyball tells the story of how the Oakland A’s, led by general manager Billy Beane, used statistical analysis to identify undervalued baseball players and compete with far better-funded teams. The core insight was that traditional scouting methods, which relied on gut instinct and conventional wisdom, often overlooked players who could contribute significant value. Instead, the A’s adopted a more analytical approach, using data to challenge biases and make more objective decisions.

This philosophy has clear parallels to early-stage investing, where conventional wisdom often drives decision-making. At RSCM, we take a Moneyball-style approach to identifying promising startups, favoring data and systematic analysis over gut feel and hype.

The Moneyball Principles Applied to Startups

1. Don’t Trust Your Gut Feel

One of the most famous lines from Moneyball comes from Beane himself: “Your gut makes mistakes and makes them all the time.” This applies just as much to investing in startups as it does to scouting baseball players. Research on gut feel (known academically as “expert clinical judgment”) consistently shows that expert intuition alone is unreliable. Statistical models built on substantial datasets outperform human judgment, even in fields like medicine and hiring.

The startup world often relies on unstructured interviews and subjective impressions, but these methods are notoriously poor predictors of long-term success. That’s why we focus on quantifiable factors and structured evaluation processes when assessing early-stage companies.

2. Use a “Player” Rating Algorithm (With Caveats)

In baseball, Moneyball relies on deep statistical analysis, drawing from thousands of recorded plate appearances per player. With startups, the data is far scarcer—most founders have very few “at-bats,” and startup outcomes are highly skewed, with the top 10% generating the vast majority of returns. This means that any attempt to create a founder “rating” algorithm will inherently be more limited.

That said, the Moneyball mindset is still valuable: rather than chasing the same overhyped, high-valuation deals as everyone else, we focus on finding undervalued opportunities. Conventional wisdom often favors founders with elite pedigrees, trendy sectors, and strong “social proof.” But those deals tend to be expensive. Instead, we seek a wide range of founders across diverse sectors and geographies, where valuations are more reasonable and potential upside is greater.

The Future of Moneyball for Startups

Even if you don’t predict massive outliers (“home runs”), a systematic approach can still yield strong returns. Our focus is on building a diversified portfolio of well-valued startups and letting the data work in our favor over time. At RSCM, we’ll keep refining our approach, looking for ways to better identify promising startups before the rest of the market catches on.

In a world where everyone chases the obvious winners, we’ll keep finding value where others aren’t looking. That’s the essence of Moneyball for tech startups.

This post was originally published on 09/28/2011 and was last updated on 03/01/25.

Further Reading

Enjoyed this post? Here are a few more posts that you might find just as insightful and engaging.

Moneyball for Tech Startups

Michael Lewis’s Moneyball tells the story of how the Oakland A’s, led by general manager Billy Beane, used statistical analysis to identify undervalued baseball players and compete with far better-funded teams. The core insight was that traditional scouting methods, which relied on gut instinct and conventional wisdom, often overlooked players who could contribute significant value. Instead, the A’s adopted a more analytical approach, using data to challenge biases and make more objective decisions.

This philosophy has clear parallels to early-stage investing, where conventional wisdom often drives decision-making. At RSCM, we take a Moneyball-style approach to identifying promising startups, favoring data and systematic analysis over gut feel and hype.

The Moneyball Principles Applied to Startups

1. Don’t Trust Your Gut Feel

One of the most famous lines from Moneyball comes from Beane himself: “Your gut makes mistakes and makes them all the time.” This applies just as much to investing in startups as it does to scouting baseball players. Research on gut feel (known academically as “expert clinical judgment”) consistently shows that expert intuition alone is unreliable. Statistical models built on substantial datasets outperform human judgment, even in fields like medicine and hiring.

The startup world often relies on unstructured interviews and subjective impressions, but these methods are notoriously poor predictors of long-term success. That’s why we focus on quantifiable factors and structured evaluation processes when assessing early-stage companies.

2. Use a “Player” Rating Algorithm (With Caveats)

In baseball, Moneyball relies on deep statistical analysis, drawing from thousands of recorded plate appearances per player. With startups, the data is far scarcer—most founders have very few “at-bats,” and startup outcomes are highly skewed, with the top 10% generating the vast majority of returns. This means that any attempt to create a founder “rating” algorithm will inherently be more limited.

That said, the Moneyball mindset is still valuable: rather than chasing the same overhyped, high-valuation deals as everyone else, we focus on finding undervalued opportunities. Conventional wisdom often favors founders with elite pedigrees, trendy sectors, and strong “social proof.” But those deals tend to be expensive. Instead, we seek a wide range of founders across diverse sectors and geographies, where valuations are more reasonable and potential upside is greater.

The Future of Moneyball for Startups

Even if you don’t predict massive outliers (“home runs”), a systematic approach can still yield strong returns. Our focus is on building a diversified portfolio of well-valued startups and letting the data work in our favor over time. At RSCM, we’ll keep refining our approach, looking for ways to better identify promising startups before the rest of the market catches on.

In a world where everyone chases the obvious winners, we’ll keep finding value where others aren’t looking. That’s the essence of Moneyball for tech startups.

This post was originally published on 09/28/2011 and was last updated on 03/01/25.

You Can't Pick Winners at the Pre-Seed Stage

People ike the idea of revolutionizing angel funding. Among the skeptical minority, there are several common objections. Perhaps the weakest is that individual angels can pick winners at the pre-seed stage.

Now, those who make this objection usually don't state it that bluntly. They might say that investors need technical expertise to evaluate the feasibility of a technology, or industry expertise to evaluate the likelihood of demand materializing, or business expertise to evaluate the evaluate the plausibility of the revenue model. But whatever the detailed form of the assertion, it is predicated upon angels possessing specialized knowledge that allows them to reliably predict the future success of pre-seed-stage companies in which they invest.

It should be no surprise to readers that I find this assertion hard to defend. Given the difficulty in principle of predicting the future state of a complex system given its initial state, one should produce very strong evidence to make such a claim and I haven't seen any from proponents of angels' abilities. Moreover, the general evidence of human's ability to predict these sorts of outcomes makes it unlikely for a person to have a significant degree of forecasting skill in this area.

First, there are simply too many random variables. Remember, startups at this stage typically don't have a finished product, significant customers, or even a well-defined market. It's not a stable institution by any means. Unless a lot of things go right, it will fall apart. Consider just a few of the major hurdles a pre-seed-stage startup must clear to succeed.

  1. The team has to be able to work together effectively under difficult conditions for a long period of time. No insurmountable personality conflicts. No major divergences in vision. No adverse life events.
  2. The fundamental idea has to work in the future technology ecology. No insurmountable technical barriers. No other startups with obviously superior approaches. No shifts in the landscape that undermine the infrastructure upon which it relies.
  3. The first wave of employees must execute the initial plan. They must have the technical skills to follow developments in the technical ecology. They must avoid destructive interpersonal conflicts. They must have the right contacts to reach potential early adopters.
  4. Demand must materialize. Early adopters in the near term must be willing to take a risk on an unproven solution. Broader customers in the mid-term must get enough benefit to overcome their tendency towards inaction. A repeatable sales model must emerge.
  5. Expansion must occur. The company must close future rounds of funding. The professional executive team must work together effectively. Operations must scale up reasonably smoothly.

As you can see, I listed three example of minor hurdles associated with each major hurdle. This fan out would expand to 5-10 if I made a serious attempt at exhaustive lists. Then there are at least a dozen or so events associated with each minor hurdle, e.g., identifying and closing an individual hire. Moreover, most micro events occur repeatedly. Compound all the instances together and you have an unstable system bombarded by thousands of random events.

Enter Nassim Taleb.  In Chapter 11 of The Black Swan, he summarizes a famous calculation by mathematician Michael Berry: to predict the 56th impact among a set of billiard balls on a pool table, you need to take into account the the position of every single elementary particle in the universe.  Now, the people in a startup have substantially more degrees of freedom than billiard balls on a pool table and, as my list above illustrates, they participate in vastly more than 56 interactions over the early life of a startup. I think it's clear that there is too much uncertainty to make reliable predictions based on knowledge of a pre-seed-stage startup's current state.

"Wait!" you may be thinking, "Perhaps there are some higher level statistical patterns that angels can detect through experience." True. Of course, I've poured over the academic literature and haven't found any predictive models, let alone seen a real live angel use  one to evaluate a pre-seed stage startup. "Not so fast! " you say, "What if they are intuitively identifying the underlying patterns?" I suppose it's possible.  But most angels don't make enough investments to get a representative sample (1 per year on average).  Moreover, none of them that I know systematically track the startups they don't invest in to see if their decision making is biased towards false negatives. Even if there were a few angels who cleared the hundred mark and made a reasonable effort to keep track of successful companies they passed on, I'd still be leery.

You see, there's actually been a lot of research on just how bad human brains are at identifying and applying statistical patterns. Hastie and Dawes summarize the state of knowledge quite well in Sections 3.2-3.6 of Rational Choice in an Uncertain World. In over a hundred comparisons of human judgment to simple statistical models, humans have never won. Moreover, Dawes went one better. He actually generated random linear models that beat humans in all the subject areas he tried. No statistical mojo to determine optimal weights. Just fed in a priori reasonable predictor variables and a random guess at what their weights should be.

Without some sort of hard data amenable to objective analysis, subjective human judgment just isn't very good. And at the pre-seed stage, there is no hard data. The evidence seems clear. You are better off making a simple list of pluses and minuses than relying on a "gut feel".

The final line of defense I commonly encounter from people who think personal evaluations are important in making pre-seed investments goes something like, "Angels don't predict the success of the company, they evaluate the quality of the people. Good people will respond to uncertainty better and that's why the personal touch yields better results." Sorry, but again, the evidence is against it.

This statement is equivalent to saying that angels can tell how good a person will be at the job of being an entrepreneur. As it turns out, there is a mountain of evidence that unstructured interviews have little value in predicting job performance. See for example, "The Validity and Utility of Selection Methods in Personnel Psychology: Practical and Theoretical Implications of 85 Years of Research Findings" Once you have enough data to determine how smart someone is, performance on an unstructured interview explains very little additional variance in job performance. I would argue this finding is especially true for entrepreneurs where the job tasks aren't clearly defined. Moreover, given that there are so many other random factors involved in startup success than how good a job the founders do, I think it's hard to justify making interviews the limiting factor in how many investments you can make.

Why then are some people so insistent that personal evaluation is important?  Could we be missing something? Always a possibility, but I think the explanation here is simply the illusion of control fallacy. People think they can control random events like coin flips and dice rolls. Lest you think this is merely a laboratory curiosity, check out the abstract from this Fenton-O'Creev, et al study of financial traders. The higher their illusion of control scores, the lower their returns.

I'm always open to new evidence that angels have forecasting skill. But given the overwhelming general evidence against the possibility, it better be specific and conclusive.


This blog post originally published on 04/27/2009 by RSCM founder Kevin Dick and was last updated on 02/14/2025.

Diversification Is a "Fact"

In science, there isn't really any such thing as a "fact".  Just different degrees of how strongly the evidence supports a theory. But diversification is about as close as we get. Closer even than evolution or gravity. In "fact", neither evolution or gravity would work if diversification didn't.So I've been puzzled at some people's reaction to RSCM's startup investing strategy.  They don't seem to truly believe in diversification. I can't tell if they believe it intellectually but not emotionally or rather they think there is some substantial uncertainty about whether it works.In either case, here's my attempt  at making the truth of diversification viscerally clear.  It starts with a question:

Suppose I offered you a choice between the following two options:

(a) You give me $1M today and I give you $3M with certainty in 4 years.

(b) You give me $1M today and we roll a standard six-sided die.  If it comes up a 6, I give you $20M in 4 years. Otherwise, you lose the $1M.

Option (b) has a slightly higher expected value of $3.33M, but an 83.33% chance of total loss. Given the literature on risk preference and loss aversion (again, I highly recommend Kahneman's book as an introduction), I'm quite sure the vast majority of people will chose (a).  There may be some individuals, enterprises, or funds who are wealthy enough that a $1M loss doesn't bother them.  In those cases, I would restate the offer.  Instead of $1M, use $X where $X = 50% of total wealth. Faced with an 83.33% chance of losing 50% of their wealth, even the richest player will almost certainly chose (a).Moreover, if I took (a) off the table and offered (b) or nothing, I'm reasonably certain that almost everyone would choose nothing. There just aren't very many people willing to risk a substantial chance of losing half their wealth. On the other hand, if I walked up to people and credibly guaranteed I'd triple their money in 4 years, almost everyone with any spare wealth would jump at the deal.

Through diversification, you can turn option (b) into option (a).

This "trick" doesn't require fancy math.  I've seen people object to diversification because it relies on Modern Portfolio Theory or assumes rational actors.  Not true.  There is no fancy math and no questionable assumptions. In fact, any high school algebra student with a working knowledge of Excel can easily  demonstrate the results.Avoiding Total LossLet's start with the goal of avoiding a total loss. As Kahneman and Tversky showed, people really don't like the prospect of losing large amounts. If you roll the die once, your chance of total loss is (5/6) = .83.  If you roll it twice, it's (5/6)^2 = .69.  Roll it ten times, it's (5/6)^10 = .16. The following graph shows how the chance of total loss rapidly approaches zero as the number of rolls increases.

By the time you get to 50 rolls, the chance of total loss is about 1 in 10,000.  By 100 rolls, it's about 1 in 100,000,000.  For comparison, the chance of being struck by lightning during those same four years is approximately 1 in 200,000 (based on the NOAA's estimate of an annual probability of 1 in 775,000).

Tripling Your Money

Avoiding a total loss is a great step, but our ultimate question is how close can you get to a guaranteed tripling of your money.  Luckily, there's an easy way to calculate the probability of getting at least a certain number of 6s using the Binomial Theorem (which has been understood for hundreds of years).  One of many online calculator's is here. I used the BINOMDIST function of Excel in my spreadsheet.

The next graph shows the probability of getting back at least 3x your money for different numbers of rolls.  The horizontal axis is logarithmic, with each tick representing 1/4 of a power of 10.

As you can see,  diversification can make tripling your money a near certainty. At 1,000 rolls, your probability of at least tripling up is 93%. And with that many rolls, Excel can't even calculate the probability of getting back less than your original investment. It's too small. At 10,000 rolls, the probability of less than tripling your money is 1 in 365,000.So if you have the opportunity to make legitimate high-risk, high-return investments, your first question should be how to diversify. All other concerns are very secondary.

Now, I will admit that this explanation is not the last word. Our model assumes independent, identical bets with zero transaction costs. If I have time and there's interest, I'll address these issues in future posts. But I'm not sweeping them under the rug. I'm truly not aware of any argument that their practical effect would be significant with regards to startup investments.

This blog post was originally published on 05/02/2012 and was last updated on 02/01/2025.