“Fixing” Convertible Note and SAFE Economics in Seed Rounds

TL;DR: In an equity round, including seed equity, any post-closing dilution is shared proportionately between investors and common stockholders (founders and employees). This is fair. Assuming no shenanigans and the business is increasing in value, why shouldn’t dilution be shared? Convertible notes and pre-money SAFEs have a math formula that makes them more dilutive to founders than an equity round with an equivalent valuation, by “protecting” seed investors from some post-closing dilution. Post-Money SAFEs are even worse. The solution is fairly simple: “fix” or harden the denominator in the conversion price formula, instead of having it dependent on complex language and variables. This gives everyone the benefit of a “floating” valuation that is so valuable in convertible instruments, while making post-closing dilution mechanics equivalent to an equity round.

Broadly speaking, there are 3 main instruments being used by startups in seed rounds: equity, convertible notes, and SAFEs. From a historical standpoint, equity (issuing actual stock at a fixed price) is the default instrument, but for reasons of speed and flexibility (on pricing), convertible notes and SAFEs have gained traction in early rounds smaller than about $2 million in total funding (the number in Silicon Valley is a bit higher).

Equity Math

While glossing over a few nuances, the formula for setting the price of stock sold in an equity round is fairly simple: pre-money valuation divided by capitalization. The higher the valuation, obviously the higher price. But importantly, the higher the capitalization (the denominator), the lower the price. In equity term sheet negotiations there is often some (necessary) back-and-forth around what actually gets included in the capitalization denominator. For example, being forced to put any increases in the option pool is fairly common. Somewhat less common but still extremely impactful is being forced to put all of your existing convertible instruments (notes or SAFEs) in the denominator. In this sense, two startups can have the same “pre-money valuation” but dramatically different actual stock prices (price paid by investors) if they negotiated different denominators.

Assumptions:

Pre-money Valuation: $10 million

Capitalization on your date of closing, including option pool increase in the round: 10 million shares

Math: valuation ($10 million) / capitalization (10 million shares) = investors pay $1 per share of preferred stock.

Simple enough. Fixed valuation, fixed capitalization, and you get a fixed price for easy modeling. Any financings (excluding down rounds) that happen after your equity round dilute the entire cap table proportionately. But the “math” for convertible notes and SAFEs is not so simple, and not as favorable as an equity round.

Convertible Note and Pre-Money SAFE Math (more dilutive)

In Why Convertible Notes and SAFES are extra dilutive I explained how the typical math of convertible notes and SAFEs makes them extra dilutive to founders/startups compared to an equity round. To summarize: because convertibles fail to “harden” the conversion math for the investors, convertibles allow seed investors to pack more shares into the denominator. Remember: higher denominator = lower price, which means the seed investors pay less and get more of the cap table even without changing the “valuation.” In an equity round, increases to the option pool after you close get absorbed by your seed investors pro-rata, but not so in typical convertible note math. Your seed note holders get “protected” from that dilution by including the pool increases in their denominator up until closing.

The fact that the denominator in convertible notes (and SAFEs, which are derived from convertible notes) isn’t fixed is actually a remnant from when convertible notes were traditionally used mostly for “bridge” rounds closed only a few weeks or months before a Series A. When your convertible round is truly a “bridge” for an equity raise in a few weeks, having your note investors get the same denominator as your Series A investors makes sense. But today seed rounds are being closed 2-3 years before a Series A. Keeping the denominator “open” for that long does not make sense.

So, keeping valuation constant, convertible notes and traditional pre-money SAFEs are more dilutive than an equity round because the denominator is larger. Why do startups use them then? Speed and flexibility.

First, given how early-stage fundraising and company-building has evolved, many (but certainly not all) seed rounds lack a true lead willing to hire their own counsel and negotiate hardened seed equity terms. Also, at the very early stages of a startup, pegging the exact valuation that investors are willing to pay can be difficult given the lack of data and track record. The valuation cap concept in Notes and SAFEs allows startups to set a proxy for the valuation, while flexibly allowing seed investors to get a lower price if the Series A valuation ends up in fact being lower than what was originally expected. Valuation flexibility (via a cap, as opposed to a fixed valuation) is a big reason why, despite the advantages of seed equity, many young startups still opt for convertibles. The ability to incrementally increase the cap over time, as milestones are reached, is also seen as valuable flexibility offered by convertible instruments.

Post-Money SAFE Math (even more dilutive)

A while back Y Combinator completely re-vamped the math behind their SAFEs, converting it to a post-money formula. See: Why Startups shouldn’t use YC’s Post-Money SAFE. Rather than setting a pre-money valuation cap, startups using the post-money SAFE are now required to set a post-money valuation, including all money they expect to raise as seed. YC’s stated reason for changing the math on the SAFE was to make it “easier” to model how much a company is giving to seed investors, but as discussed in the blog post, anyone who’s deep in this game and unbiased knows that claim is smoke and mirrors. The formula change made the SAFE structure far more favorable to investors (including YC) economically.

What was really happening was that because pre-money SAFEs had exactly zero accountability protections relative to seed equity and convertible notes – the maturity date in notes constrains the ability of startups to keep raising more and more rounds without converting the seed round into equity – seed investors in SAFEs were getting burned by startups raising SAFE rounds for years and years without ever converting. As an investor, YC itself was getting burned. So they changed the SAFE to be more investor friendly, benefiting YC and all seed investors.

But in the opinion of many ecosystem players, including lawyers focused on representing companies (and not the investor community), the change was egregiously one-sided. It effectively forces founders and employees (common stockholders) to absorb all dilution for any other convertible note or SAFE rounds that they raise after the post-money SAFE round, even if the valuation cap is higher. That’s an extremely high price to pay just for making modeling seed rounds a little easier. I have a better (fairer) idea.

“Fix” the Denominator in Notes and Pre-Money SAFEs (same dilution as equity round)

The benefit of convertible notes and SAFEs is flexibility and speed. They are simpler, and allow you to have a “floating” (flexible) valuation (cap) that helps companies and investors get aligned despite the uncertainty. This “floating numerator” is important and valuable.

But as discussed above, while the benefit of notes/SAFEs is a more flexible numerator (valuation), the benefit of seed equity math is you get a hardened denominator. That hardened denominator ensures that everyone (common stock and investors) shares pro-rata in post-closing capitalization changes, like future rounds and option pool changes. Everyone has appropriately-apportioned “skin in the game.” Another benefit of this hardened capitalization (denominator) is that it makes modeling the round easier. Wasn’t that what YC says they were trying to do with the Post-Money SAFE? Why not make modeling easier without hurting founders with harsher dilution?

So the “best of both worlds” solution is: do a convertible note or pre-money SAFE, but harden the denominator with the capitalization at the time of closing. You can even ensure it has an appropriately sized pool to account for expected equity grants until the next raise, much like you would in an equity round. Flexible numerator, but hardened denominator.

Making this change in a convertible note or SAFE is extremely easy. You simply delete all the language used for describing the denominator (the fully-diluted capitalization) and replace it with a number: your capitalization at the time of closing. Now both sides have the benefit of a valuation cap that adjusts if there is a “down round,” but a hardened denominator that allows everyone to model the expected dilution of the round; while ensuring that future dilution is shared proportionately between both founders and investors.

On top of being far more aligned with equity round economics (the default approach to fundraising), this approach can save common stockholders several percentage points on their cap table; a very high impact from just deleting a few words and replacing them with a number. When a seed equity raise won’t do, my recommendation is usually a low-interest, lengthy (2-3 yrs) maturity convertible note with a valuation cap and hardened denominator. As a lawyer who represents zero investors (all companies), I’ve felt that pre-money SAFEs are too company-biased, and post-money SAFEs are too investor-biased. SAFEs in general are also far less respected by investors outside of Silicon Valley than convertible notes are.

We’ve been explaining this issue to clients and investors and are happy to say that there has been a positive reception. We hope to see it utilized more broadly in the market over time. See: A Convertible Note Template for Startup Seed Rounds for a convertible note template that startups can utilize (with appropriate lawyers) for their seed rounds.

Do I expect all seed investors to adopt this approach? Of course not. They’re investors, and will naturally prefer something far more aggressive in their favor, like YC’s post-money SAFE. It all depends on context, character, and leverage. Nevertheless, founders should go into seed rounds with their eyes wide open about the significant economic implications of the various structures and formulas, and not give into any hot air about there being a single (air quotes) “standard” approach, when what investors are really promoting is their preferred “standard.”  Pushing misleading “standards” is a far-too-common negotiation tactic for getting inexperienced founders to mindlessly pursue financing strategies that are against their company’s interests.

Bundled v. Unbundled Startup Capital

TL;DR: The market for early-stage startup financing has reached a level of fragmentation and hyper-competition (among capitalists) never seen before. This competition has led to an increasingly atomized market, with a multitude of players offering different takes on the traditional “bundled” offering of smart venture capital. Startups and founders should understand the reasons behind the marketing narratives pushed by each of these players, so they don’t get too swept up in an overly simplistic strategy for how to raise capital. The best strategy is to diversify your capital sources, while still allowing room for smart leads writing large enough checks to provide real value add.

The world of early-stage startup financing looks extremely different today than it did even 5 years ago, and completely unrecognizable to the market of a decade ago. The reasons are fairly straightforward. Near-zero interest rates and slowing of international economic growth, together with government policies of quantitative easing (which inflate traditional asset prices and make further returns harder to achieve) have produced a surge in the amount of capital seeking any kind of “alpha” in the seemingly “final frontier” of early-stage startups. There is far more money chasing startups than perhaps any time in history.

This surge in early capital naturally produces a surge in competition among early capitalists. In order to navigate that competition, capitalists, just like any other service provider, seek ways to differentiate themselves in the market to avoid appearing too much like a commodity. It’s this need for early capitalists to differentiate themselves that has produced the “atomization” or unbundling of startup finance that is increasingly visible in the market. The point of this post is to help founders and early teams understand that unbundling in assessing their own financing strategies.

To speak of unbundling of course requires first understanding the original bundle. Historically, conventional venture capitalists “sold” the following bundle to startups:

  • Green cash money (obvious)
  • Signal – a brand that credibly signaled “eliteness” to the market (de-risking to an early startup), making it easier to further attract capital, employees, commercial partners, etc.
  • Network – a deep rolodex/LinkedIn network of contacts to leverage in recruiting and expansion
  • Advisory – active involvement on Boards and “coaching” to inexperienced executive teams.

In the very early days of conventional venture capital, VC was very scarce. In many markets there was quite literally one, maybe two funds, who served as gatekeepers to the market; and unhesitatingly used their market dominance to squeeze teams on valuation and corporate governance power. This “asshole” behavior inevitably produced demand for alternatives.

Enter the new “friendly” venture capitalists. Very large VC funds started to break up because the personal brands of high-profile VCs incentivized them to form their own funds with fewer mouths to feed. Growing interest in early-stage also brought in new market entrants. As the VC market evolved from a more oligopolistic structure to an increasingly fragmented and competitive market, the need for differentiation increased. “Friendliness” (or at least the well-calculated appearance of it) became a successful way to achieve that differentiation. You now had VCs actually competing with each other based on their reputation. But the general bundle offered by those VCs largely remained the same.

Another successful form of differentiation in this era involved going deep on “value add” services. Particularly in SV but now also in other markets, VC funds began to hire non-partner staff whose purpose was to, completely apart from providing money and Board service, help CEOs with recruiting, marketing, sales, etc. as a kind of external extension of their internal team. All that extra staff naturally costs money, and increases the overhead structure of the fund, which then increases their pressure to achieve highly outsized returns and avoid overly generous valuations.

So in the initial era of startup funding growth, VCs became “friendlier” (though caveats are worth emphasizing, see Trust, “Friendliness,” and Zero-Sum Startup Games) – and bulkier. But the flood of new capital kept on coming. VCs continued splintering off and forming micro-funds. More entrants arrived. Successful exits produced new, younger teams interested in trying their luck at the VC game. What to do with the VC market becoming even more competitive? Differentiate even further.

Enter accelerators and seed funds, and eventually pre-seed funds. As the true Series A market became increasingly crowded, continued competition among capitalists led many to conclude that the new way to avoid commoditization was to go earlier in the life cycle, closer to the territory once filled exclusively by angels (named as such because of their willingness to take risks once deemed off the table for professional investors). Rather than continuing the game of bulking up and emphasizing the “full package” bundle of traditional VCs, these new institutions sought differentiation by slimming down, and emphasizing their ability and willingness to move fast and early. Those old-school VCs are slow and over-bearing, the marketing content says. They don’t really provide any value-add. Take our cheaper, faster, “friendlier” money instead.

We are now entering a new era where “solo capitalists” are the hot topic. New in some ways, but the same dynamics of market competition and necessary differentiation are quite old. Why take money from a fund at all, when you can just raise from a set of successful solo founders? They’re super friendly, don’t care about a board seat, and will move lightning fast without pestering you with “negotiation” or other trivialities. Their ultra-low overhead also means they can pay higher valuations. And of course they’re enabled by new tech platforms for raising and distributing capital that are very much invested in the increasing atomization of startup capital, which increases demand for technology to coordinate and facilitate that atomization.

In 2020, the market of very early-stage funding for startups now looks like this:

  • Solo angel investors
  • Angel networks
  • Angel “syndicates”
  • Accelerators of various flavors
  • Scout money from “bulky” traditional VCs
  • Pre-seed funds
  • Seed funds
  • Series A funds that invest in seed rounds
  • Solo VCs
  • “Lean” startup lenders

Throw in the reality that geography is hardly a barrier to capital flows now – especially in the COVID era – and the early-stage funding market has reached a level of hyper-fragmentation and competition that was unimaginable a decade ago. Within a particular market, the number of players has shot up dramatically, and now those players are increasingly happy to cross state lines.

This is undeniably a fantastic environment for top-tier teams looking to raise early funding. It’s also undeniably a far more stressful environment to be a startup investor. Ten years ago being a VC meant everyone came to you, very warm intro required, and you called the shots. Now VCs hustle so hard for visibility some are even engaging production studios to help them create polished youtube channels. Others don’t even require intros anymore and have opened their DMs on twitter. There are even jokes about VCs trying to create viral memes to get eyeballs. Life comes at you fast.

The important message for startup teams is to understand why the landscape now looks the way it does, and the incentives behind why any particular type of investor markets itself the way it does. Accelerators, for example, now face far more competition than they did in their golden era, particularly from seed funds with legitimate “value add” offerings. See: Why Accelerators Compete with Smart Money. Because the “bundle” of an accelerator is heavily weighted toward its network and signaling value, accelerators have for some time been incentivized to promote a narrative of “dumbing down” early capital that doesn’t have its own competing network, thus keeping the accelerator’s value proposition somewhat relevant.

Similarly, ultra-lean funds and Solo VCs lack by design the resources of larger funds, and thus they are incentivized to push a narrative that traditional “hands on” VCs don’t really add value. The new lean players don’t have the time or the resources to add value themselves, so best to talk as if that particular part of the traditional bundle isn’t that meaningful anyway.  This all, of course, is easily disproven by the number of founders in the market who credibly testify to the value (in advisory, network, deep long-term pockets) in having a large fund with full skin-in-the-game on your Board and cap table. Some (not all) large funds really do provide significant added value.

And of course, traditional VC funds talk their own books with the exact opposite story. The fragmented lean investors are all spray-and-pray “dumb money” looking for party rounds. Teams need value add from seasoned, steady hands willing to roll up their sleeves on Boards. You need more than atomized money. You need a trusted “partner” to shepherd you toward success.

There is absolutely no need to take sides in all of these narratives. Why should you? Every player in the market offers a grain of truth, but also exaggeration and over-simplification, in what they’re saying. The most important thing is not to get too swept up in moralizing or marketing. Understand what each player is selling, and understand what your particular needs are.

Often times the smartest teams do a bit of “shopping” across various aisles in the new VC supermarket. Team up with a reputable seed fund, but use your optionality to ensure the terms are reasonable. Let them write a large enough check to be emotionally invested, but fill the rest of the round with smaller high-signal checks that will also be motivated to connect you with their networks. For good measure, if you have interest from a traditional Series A VC fund, let them write a small check in your seed round to keep the connection warm when Series A discussions start. The fact that they know how well networked you are (thanks to the other players on your cap table) will ensure good behavior at the Series A term sheet stage.

Contexts will vary and team needs will vary, so the particular mix of early capital any particular startup takes will naturally vary as well. Stay flexible and avoid rigid theories about the (air quotes) “right” way to raise funding. But in all cases, make an effort to diversify your network and capital sources. Nothing ensures good behavior from the money better than making it crystal clear that you are well-networked and happy to take someone else’s check if your current investors don’t play ball. You can do so while still building strong connections with your investors, demonstrating that you value their relationship. This is a great time to be an entrepreneur, whether in or outside of Silicon Valley. In navigating the new early-stage funding market, don’t drink too much of anyone’s kool-aid, and shop wisely.

The Weaponization of Diversity

This is an unusually extra lengthy essay, because the issue is so complex, sensitive, and nuanced that it deserves an appropriate level of patience and attention. It includes my deeply honest, personal, and some would say risky perspective on the topic of diversity in high-performance elite careers, including tech entrepreneurship; and my concern, as a latino who grew up low-income, that the decision by some to “weaponize” diversity is backfiring and causing harm to under-represented minority (URM) groups.

I would like to emphasize the distinction between “American Latino” and “Latin American” in this essay. By American Latino, I refer to Latin Americans (and their children) who migrate to the United States, and as a result are a sub-group (with various selection biases) of Latin America. The importance of that distinction will become clearer as you read on. 

I grew up in a very “colorful” part of Northside Houston, with neighbors and schoolmates who were usually a mix of latino (immigrants and 2nd generation), black, asian and white; and a general socioeconomic range hovering between welfare, blue collar, and sort-of-middle class. My parents (Mexican immigrants) started a produce business selling avocados and tomatoes, which eventually grew but then unfortunately imploded. By the time I was sending off college applications, my two sisters and I were supported by our single mother who sold perfumes at an indoor flea market. After public K-12, I ended up attending the University of Texas and Harvard Law School, graduating in both cases with various honors. Today, with three healthy kids, happily married over a decade and a successful legal practice/leadership position at an elite boutique law firm, my cozy “1%” life definitely does not suck.

But this isn’t your classic self-congratulatory American Dream story. There’s a key twist, and that twist has given me a unique perspective on issues of socioeconomic inequality and diversity. My mother, despite ending up in a struggling, unstable situation, was actually a computer science graduate of the top technology university in Mexico; the Tecnologico de Monterrey. Basically the MIT of Mexico. And her family background includes a nationally celebrated Mexican artist and a biological (but estranged) father considered one of the top medical doctors and medical school professors in his field.

How did my mom go from a top-tier student with a strong family background to selling perfumes at a flea market as a single mother hovering preciously close to Medicaid-level poverty? This isn’t my autobiography, so I’ll cut that part of the story short and summarize: very difficult mental illness. Many people fail to appreciate how success is just as much about emotional stability and health as it is about intellectual and analytical capacity; and the formula for producing the former is often far more complex and nuanced than what’s necessary for the latter.

I mentioned these details about my mother because they are historical elements that keep me, if I’m honest, from painting for you a perfect “everything is totally fine because I made it” story; the kind of story that is too-often used to ignore real problems in society. My mother’s emphasis on academics and her love of computers – which she made every effort to expose me to, within her limited means – were key strategic assets in my childhood that differentiated me from my peer group, and undoubtedly propelled me forward. The truth is the vast majority of people who give you these “rags to riches” stories can, if they’re sincere enough, come up with their own kinds of privilege (including familial privilege) that they depended on growing up. If anything, simply being born “gifted” (to use a very broad but frequently used term) is itself an unearned privilege reserved for a lucky few who often like to conveniently overlook their luck.

Yes, we were poor latinos living in a low-income area and a broken home, speaking a blend of spanish and english and having our fair share of tamales, frijoles, barbacoa, etc. A (candidly) stereotypical and recognizable American Latino household portrait. But as it related to school, my home culture (driven by my mother) was different, and my latino peers noticed. I studied hard, taking advanced coursework beginning in elementary and through high school. I entered college on a full academic scholarship with enough advanced credit to almost qualify as a junior; some of that credit having been earned from reading textbooks on my own because my high school didn’t offer a particular course. My level of academic discipline got me labeled as “acting white” (by other latinos) more than enough times. There was even a special term for it: “coconut.” Brown on the outside, white on the inside. I had friends growing up who studied as hard as I did, but none of them were latino.

I didn’t know it at the time as a boy or young man, but the gulf in home culture between myself (via my mother) and my latino peers in Houston was encapsulated in a phrase I often heard from mom: “we don’t behave like those latinos.” It was all class cultural conflict reflected via playground insults (coconut) and maternal chastising (to succeed, don’t replicate “poor” culture). I struggled with this tension of identity growing up – I was definitely not “white” but somehow a different, less familiar and far less common (in the U.S.) kind of “Mexican,” and my latino friends could tell.

Very very few of my childhood American latino friends have ended up as successful doctors, lawyers, engineers, executives, or entrepreneurs, including some who had more money and far more stable families than we did. Many didn’t even go to college. Whenever I hear someone bring up statistics about the under-representation of latinos among the top economic strata in the U.S., I think about my childhood experiences and how differently I saw the world from my friends, because of the expectations I had at home; my “coconut” expectations. Rare among Mexican-Americans, yet not so for other American immigrant groups (more on that below), I grew up with a low socioeconomic status but cultural education expectations more typically aligned with upper classes.

I often think about how much I heard, and sometimes still hear, underachieving peers lash out at the world for its supposed racism and prejudice against latinos; and yet, with a name like Jose, there was no hiding my own ethnicity. If the world I was living in had deep, systemic discrimination against latinos, surely I was an easy target. Certainly I’ve encountered some bona fide racists, but rarely were they in positions of influence to alter my trajectory. And of course there are stereotypes that I’ve had to overcome. But, again, given the progressiveness and merit-driven nature of the people and institutions of influence I’ve encountered (and thank God for that), the stereotypes eventually gave way to what I could actually deliver.

I’ve learned to not be so offended by weak stereotypes, because given my experiences growing up, I understand full well why they exist. Stereotyping is at some level a normal, even if often unfortunate, function of human behavior. We had plenty of stereotype jokes in our household growing up, particularly about white people. Stereotypes alone do not really make you a racist. They make you human. It’s how strongly you hold onto a stereotype, and your willingness to give individuals the benefit of the doubt, that determines whether or not you deserve the label.

Yes, bias exists, and we should work to overcome it. But it doesn’t and hasn’t existed solely for modern-day under-represented minorities. Jews, Asians, Indians, and all kinds of immigrant and religious groups have historically faced discriminatory bias in America (and all over the world). For American Latinos to dwell on “unconscious bias” as the primary reason for their under-representation is to ignore the reality that dozens of other groups found ways to overcome the biases they faced in society. So why would the bias we face be so much more, and uniquely, insurmountable?

Constant discussion of bias in the market amounts to what I would call, frankly, “unfairness porn.” Addictive to some, and even a lucrative career for others, but ultimately of questionable impact relative to more actionable topics. It’s not entirely wrong, and there’s some value in it. I empathize with those who work in that area. But big picture it feels like a time-consuming distraction from deeper issues which, if addressed, would naturally resolve negative bias over time. Nothing is more impactful at overcoming bias than creating a record of unambiguous and credible results.

Let’s jump back to the unfortunate above-mentioned personal fact: very few of my latino friends ended up successful. Why? Racism? Systemic discrimination? I’m sorry, but you won’t convince me of that. I will acknowledge that stereotypes are out there, and they do impact latinos at the margins, but my own experiences, observations, and reflections make it impossible for me to accept that the dramatic under-representation of American latinos in high-performance industries today is the result of their being discriminated against for being latinos. The gap is simply too large, reflected across numerous top-tier industries, and many of these industries are simply too competitive and lucrative for key players to ignore truly untapped talent being kept on the sidelines.

If you want to argue for strong, systemic discrimination against latinos, you’ll have to explain the very big gaps in outcomes between, say, Cuban-Americans and Mexican-Americans. A reflective and honest latino can explain that gap very quickly. Cuba had a “brain drain” thanks to Castro. Mexico did not. Every major country has different strata with their own subcultures and attitudes, including about education, work, family building, and many other life factors. Mexicans certainly share a common culture, but a Mexican banker or professor has a very different attitude toward education than a Mexican laborer or restaurant owner; much like how the general culture of Cambridge, MA is very different from that of West Virginia.

History has caused Cuban immigration to the United States to select more for Cubans with values that help them succeed at higher levels of performance in an education and capitalism driven society, while Mexicans with similar values have disproportionately chosen to stay home, with their much more blue collar counterparts (with far less emphasis on academics) leaving to America. But because of relative population sizes and geography, the number of Mexicans who have migrated to America completely dwarfs Cubans, and so the generalized data (and outcomes) of American latinos reflects more the outcome of Mexican-American culture (laborer, blue-collar) instead of affluent Cuban-American culture (academics, entrepreneurship). Nevertheless, they are both American latinos, and would face similar “racism” and “bias” in American society. The dramatic difference in their economic outcomes is telling.

You see this issue pop up between black Americans of recent African descent – like Nigerians and Ghanaians – relative to African-Americans with lengthy American histories, including with slavery and Jim Crow. Nigerian and Ghanaian Americans, and their children, are far more economically successful on average than other black Americans, including by some measures more successful than average white Americans. But just as between Cubans and Mexicans, any “racists” would have a hard time distinguishing them from appearances. Clearly this systemic discrimination narrative is more complex than some make it out to be. Immigration patterns have generated a “brain drain” from various African countries that selects for members of those populations with values that generate more positive outcomes.

Of course, this isn’t to pretend that the selection process of differential migration alone explains the full outcomes of different groups. Confucianism goes a long way in explaining why certain “Asian” cultures are obsessive about academic achievement for their children. China broadly cares a whole lot more about school performance than Mexico does (or anyone else for that matter). Talmudic history similarly explains the strong outcomes of Jews. Explaining Mormons is a little more complicated. But the general message is centuries of distinct history produce distinct cultures with distinct values that generate distinct kinds of performance in distinct environments. How many elite Chinese-American baseball players are you aware of? Culture matters. A lot.

So why is there such a disproportionately small number of American latinos in high-achievement careers? To give a full answer, it would take a day’s worth of conversations, and hours of writing. On a socioeconomic level, latinos in America obviously face barriers like higher amounts of poverty, poor schools, cramped housing, and all the challenges of being in the lower economic brackets typically reserved for recent immigrants. Regardless of what minority group you are talking about, these factors push down long-term performance.

Yet the data unavoidably shows that, even when controlling for socioeconomic barriers, certain groups still dramatically outperform others in school and long-term economic outcomes. It also shows that even in affluent environments, wide achievement gaps between groups persist, and are linked to parental educational engagement, expectations, and perceptions about how educational achievement impacts market success. There are even studies demonstrating that among under-represented minority students, there is a negative correlation between high academic achievement and popularity among their same-ethnicity peers.

Do not interpret this as suggesting that economic inequality is not a serious problem in America. Without a doubt, it is. But the point here is that given the number of under-represented minorities “of color” who aren’t poor, and even attend decent schools, if poverty and weak schools were the main issues we would see much better representation of URMs in high-performance industries than we currently do. The fact that, on average, even middle and upper middle class URMs continue to reflect an educational performance gap, but that the gap narrows and even disappears for specific sub-cultures of URMs, necessitates acknowledging that something deeper is at play.

To ignore the reality of cultural values is to cowardly stick your head in the sand, and therefore never fully address the main source of the problem. American Latino culture (generally) heavily promotes short-term economic gain over the kind of long-term success requiring what’s often called “delayed gratification.” If you find a decent job right outside of high school (and even during high school) that can afford you a relatively nice car and possibly a modest home, your “network” as an American latino is far more likely to celebrate your achievement. If you grind out your high school years acing AP classes (having taken advanced classes in middle school), forgoing short-term economic opportunities in hopes of getting a BA and even a masters degree, you’re more likely to be called a coconut.

American Latino culture (specifically the culture of the strata of latinos who come to America, which is very different from Latin American culture generally), for all of the above-covered reasons having to do with history and immigration selection, disproportionately prioritizes blue collar and middle-class success over the long-term delayed training required to reach the upper tiers of high-performance professions. Where are the millions of Mexican parents who demand academic excellence from their kids? Largely in Mexico, where, because of a dynamic economy (tied closely to the U.S.) that functions quite well for the upper classes, they are successful and have no reason to leave.

High-performance professions, like law, engineering, and medicine, are heavily oriented toward the kinds of skills that depend on long-term, compounding training and achievement. Unlike, say, marketing or sales, where someone with a natural gift could possibly not do that well in K-12 and still quickly absorb necessary skills for high-performance post-school, it is very hard to make up, in a matter of a few months or even years, for extremely weak math and science training if you want to be an engineer or doctor.

Heaven knows many universities try (and bless them for it), but they simply cannot waive a magic wand and erase a poor public education and home environment (culture) that failed to instill academic rigor over the course of over a decade, including during a child’s most formative years. They have made great strides in helping students with weak backgrounds “catch up” for middle class oriented careers, but the gap for top-tier achievement is simply too high. Think of what it takes to be a world class violinist. How many of them started training only when they got to university, or even high school? Virtually none. How a child spends their time heavily influences the performance level they are able to attain as an adult, especially in careers dependent on compounding skillsets with high-performance requirements.

Thus, these career tracks by their nature – a nature that has absolutely nothing to do with racial discrimination, mind you – heavily disfavor anyone who doesn’t show up to college with a relatively solid academic background. That means, disproportionately, American latinos (and also other subcultures, like rural whites in Appalachia). To really address this problem requires a lengthy, candid discussion about childhood, parenting, family structure, and cultural identity. Calling “the system” and its performance standards racist gets you nowhere.

Yes, certain groups do better than others in the system, but that’s generally because they better prepare children to meet its logical and unavoidable requirements, with a home environment that emphasizes high educational expectations from an early age. Rather than pretending that reasonable and necessary meritocratic standards, which an enormously diverse set of ethnic groups and nationalities are able to succeed within, are “racist” and oppressive – a logic that has more to do with defeatist Marxist ideology than racial supremacy – we should be addressing the background sociocultural and educational reasons (originating in early childhood and education policy) behind why certain groups struggle disproportionately with the standards.

To be clear, one can reasonably acknowledge that the historical origin of the educational values of certain URMs is directly tied to oppression and lack of opportunity. This is certainly the case with laborers and low-income migrants from Latin America, where social mobility is generally worse than it is in the United States. Latin American laborers have, because of colonialism and its legacy, historically been denied access to viable education and thus, over generations, a distrust and skepticism of the real payout of long-term academic effort (and starting very early in that effort) became engrained in their values. Contrast that with China, where for centuries the entire basis for virtually all social mobility rested literally on a standardized exam (the keju, or imperial examination). China invented standardized testing, so guess who is really good at studying for tests? History matters.

But with all of that being said, even if oppression is the historical cause of cultural values that now generate underperformance, that doesn’t at all mean that today URMs are (on average) underperforming because they are academically or professionally oppressed. History can’t be changed, but culture can evolve, if we’re willing to be honest about it. These groups have the opportunity to begin learning and integrating more successful strategies into their identities and cultures today, just like others have done so in the past. Unfortunately, some of the strongest interference in this process comes from confused third-parties who want to pretend that there really is nothing new to learn, other than a few statistics about “unconscious bias.”

Acknowledging the cultural underpinnings behind educational performance gaps, and how they directly align with under-representation in top-tier industries, is not about blaming under-represented minority groups for their challenges. No one chooses the culture of their childhood, or the history of that culture, any more than they choose their parents or skin color. But acknowledging the issue, no matter how much certain misguided commentators demand silence, is essential for ultimately resolving it. In fact, the combative tendency to immediately shout down anyone as “racist” or offensive for sincerely raising these issues is precisely why discussion remains stuck in a phase of stale and exhausted, but easier-to-discuss ideas; like “trying harder” to find qualified candidates.

Now speaking even more narrowly for the audience that frequents this blog: why are there so few successful latino tech entrepreneurs? I’ve already explained part of the answer. As much as we celebrate people like Mark Zuckerberg and Bill Gates dropping out of Harvard to start tech companies, it’s worth emphasizing that first they still got into Harvard, and second they surely must’ve learned the skills necessary to start tech companies somewhere before getting to Harvard. Tech entrepreneurship is dependent on a compounding skillset that, again, filters out people whose childhoods failed to help them develop that skillset. Zuck and Bill didn’t learn to code during their freshman years.

But let’s put aside the compounding/technical skill issue for a moment, because there’s a more nuanced issue at play here, and it relates to the point I made when discussing my mother’s poor outcome despite her clear academic intelligence: success depends on technical skill but also, particularly in certain environments, on emotional/psychological resilience.

There’s a frequently cited John Adams line that I am going to paraphrase and somewhat modernize: people become farmers, so that their children can become merchants, so that their children can become professionals, so that their children can become artists and entrepreneurs.

What is this line telling us? That there is often a generational progression to career trajectories, and that progression is tied to economic stability, which itself is tied to psychological resilience and willingness to take risk. I can tell you, having worked with and observed hundreds of entrepreneurial ventures, your average tech entrepreneur is not coming from a low-income or even blue collar/middle class background. Zuck and Bill certainly did not.

It often takes a childhood environment that infuses a person with confidence about their family/network’s overall economic stability to enable that person to confidently take the enormous personal risk of becoming an entrepreneur; instead of going into a nicely salaried career. Wealthy kids are far more likely to grow up to become entrepreneurs, because they know that going “bust” doesn’t mean actually going homeless, but instead there’s an enormous set of resources there to serve as a parachute.  Kids with similar technical or “intellectual” ability, but with families living on the precipice of poverty, or at least with very few excess resources to manage a blowup, do not have that luxury.

This is not to say that tech entrepreneurs with wealthy backgrounds are not big risk takers. Most of their equally wealthy friends probably still went into consulting and other salaried jobs. But it is to at least acknowledge that having an affluent background dramatically subsidizes personal risk tolerance.

I do not regret for a second becoming a VC lawyer instead of becoming an entrepreneur. Neither of my parents had any substantial savings. In fact, I support my mother in her retirement, and most of the rest of my family struggles on a daily basis to even stay in the middle class (loosely defined). Unlike Zuck or Bill, failure in my case would’ve, quite literally, risked homelessness. I have met entrepreneurs who really did risk homelessness/poverty in starting their entrepreneurial ventures, but they are a far smaller minority than is suggested from the heroic “risk absolutely everything” stories one often hears in the media.

So I went into a career that made sense for my low-income family background/history. No regrets. I can guarantee you countless high-achieving latinos (and other minorities) make this exact decision on a daily basis. Startup? Sorry, I’ve got parents and other extended family to help out. I’ll take that high-salaried job I busted my tail and sacrificed for. Maybe my kids will have a better parachute.

Many high-achieving under-represented minorities simply do not have the luxury of parents, aunts, uncles, and cousins all with stable incomes and savings to provide them a parachute for an entrepreneurial adventure. Now, their kids might (see the John Adams line), but that’s why changing the long-term economic success of any broad group simply cannot be wished into existence. The most challenging forms of success take an entire childhood of compounding learning, and going even further, the very highest risk paths often take generational building of wealth and resilience.

We like to think of entrepreneurship, including tech entrepreneurship, as a very democratizing, equalizing playing field where anyone with the right motivation and persistence can succeed; but my honest experience is that today, in fact, it’s the opposite. High-achieving entrepreneurship takes a spectacularly rare and complex combination of analytical and technical skills, communication skills, social skills, and creative judgment about current and changing market conditions, on top of incredible psychological resilience. Rather than an easily accessible field for anyone who wants to play, modern hyper-competitive tech entrepreneurship represents the apex of human abilities, creativity, and endurance. We should not be surprised that, for most people, the necessary (but not sufficient) conditions for reaching that apex start well before adulthood; and include a childhood environment that supports high achievement.

Tying this all together: first, the compounding technical skill “filter” disproportionately impacts American Latinos (and similar groups) because cultural, not just socioeconomic, factors lead fewer of them to develop the compounding skills in childhood that make tech entrepreneurship (or many other high-performance careers) feasible. Second, for the disproportionately small number of them who still end up getting there, they are far less likely than other groups to come from the kinds of stable economic backgrounds that make high-risk paths like entrepreneurship attractive. Among under-represented minorities like American latinos, the “best and brightest” are, much more so than other groups (but certainly not always), drawn toward stable high-income professions and away from high-risk paths like startup employment and entrepreneurship.

Now, let’s ask ourselves a hard question. How much of this unfortunate reality can actually be materially impacted by recruiters and investors in any short-term sense? It takes time for the descendants of low-income immigrants to build the kind of economic stability and resilience that encourages very high-risk, very high-reward paths. Anyone expecting to actually impact long-term collective outcomes needs to face, head on and without unproductive outrage or finger-pointing, the fact that helping people meet the requirements of high-performance takes time. It also takes honesty about the cultural/behavioral values that build up children to face those requirements as adults. The requirements themselves, no matter how much we might wish otherwise, are not going to budge.

I want to see more “people of color” in tech entrepreneurship and other high-performance careers just like all other good, honest, progressive people. But I’m afraid that a segment of the community – either well-intentioned or not – has chosen to weaponize the issue of diversity in a way that is not only hostile and disingenuous, but counterproductive to its own cause.

There are historical, cultural, and socioeconomic reasons – all of which have been exhaustively studied – that explain why a disproportionately small number of people in certain ethnic/minority groups are able to achieve the high levels of performance and economic success attained by other groups. The number of high-performing candidates “of color,” in the sense we are discussing, is in fact smaller. Throwing the label “racist” around indiscriminately, and trying to guilt decision makers – like recruiters and investors – into hiring or investing in more of these candidates than realistically exist (today) can backfire. Dramatically. I’ve seen it happen.

I’ve seen very well-intentioned “diversity” accelerators created with much fan-fare and PR. But because they didn’t actually dig into the deep, complex reasons for the low representation of certain groups in their industry, and instead wanted quick and easy results, what actually ended up happening is that they promoted companies that underperformed and underachieved. The end-result? They very loudly and publicly reinforced the very stereotypes they were trying to break. Even more sadly, already successful/wealthy people, usually white, still get their PR and photo ops from these initiatives, while minorities are, once again, left holding an empty bag. On the most important issues, good intentions are not enough. Instead of stereotypes truly holding us back, we are foolishly incentivizing their amplification.

In the case of many mission-driven “diversity” venture funds, they’ll often amplify the idea that venture capital is racist or systemically discriminatory, but a quick glance at their portfolio makes it clear that they are sourcing and funding various kinds of businesses that do not generate true venture capital returns (but fulfill their mission). That they are choosing to fund other lower-margin, lower-scale kinds of businesses is great, and yet their claims that venture capitalists seeking high-scale, high-margin venture level returns are “racist” are still disingenuous.

The more exposed any position is to the harsh, unforgiving reality of the market, the harder it is to compensate for underperformance. This is why large organizations, like the government (including the military) have historically been the best environments for “affirmative action” type initiatives that acknowledged some preferential treatment of under-represented minorities, but are able to contain and address any performance issues with the “slack” of the large organization. Very high-performance, high-stakes positions, like startup entrepreneurship (and also complex law, by the way) unfortunately don’t have this luxury. If there are nuanced, complex reasons for why a disproportionately small number of American latinos meet the requirements of medical schools, I doubt anyone wants to suggest we guilt and shame the schools into graduating more of them anyway.

Tech startups operate in the most performance-driven, cut-throat, “figure it out or die” segment of the economy. Unlike large organizations with many layers of staff and substantial buffer resources for training, bringing on anyone who underperforms risks catastrophic failure for a startup team. The reasons they underperform may be totally unfair: disadvantaged background, low-income, poor education, etc., but, again, customers don’t care. Can an NFL team afford to take into account “fairness” in whom they put on the field? No, and neither can startups. Once we clear out true discrimination, any attempts at increasing representation must involve actually improving the performance of the underrepresented groups.

The world of startups is one of the most culturally progressive environments I have ever encountered in my life. But it is also, by necessity, fiercely (even if imperfectly) meritocratic. This fact makes it quite “colorful” in terms of the full diversity of ethnicities and nationalities one encounters – hardly all white American-born men, but it also means wide performance differentials between groups are going to be unavoidably visible in outcomes.

The great “myth” of the tech sector, or really of the entire high end of the modern economy, isn’t a myth of meritocracy. Competitive markets make it very expensive to hire under-performers, or to discriminate against available talent. We have, perhaps more than any time in history, meritocracy. The myth is that meritocracy (alone) means equal opportunity. To the contrary, hyper-meritocracy puts an enormous premium on having a strong (socioeconomic and cultural) background that prepared you with compounding training, because you need to show up on Day 1 ready to perform. Meritocracy massively privileges having a good childhood, including a home culture that enables, from very early on, high achievement. Appealing to racism and prejudice among the decision-makers in elite institutions (including employers) isn’t necessary at all for explaining the wide disparities we see in our increasingly meritocratic market economy. The problems aren’t post-college, but pre-high school; going as deep as early-childhood development and parenting.

The fact is that, in the United States, equal opportunity largely stops at who your parents are. Relative to other developed countries, America is particularly egregious in how little it does, especially in early childhood, to prevent young kids’ educational trajectories from becoming extremely dependent on the private initiative (and resources) of their parents. Meritocracy ensures people are measured by the skillset they bring to the market, but without additional public policies it does nothing for the kids who aren’t born into families that, from a very young age, help them develop their skills so that they benefit from the kind of long-term compounding that produces very high-performing adults. Some of those kids start to take control of their educations around high school when they begin thinking about financial independence as adolescents, but by then high achievers have had a 5-10 year head start. The nature of compounding is that gaps widen over time; they rarely close.

It’s these “late bloomer” strivers who often struggle the most with observed performance differentials in the market. They are just as intelligent and hard-working (as adults) as higher-achieving peers, and so they understandably conclude that employers and universities must somehow be stacked against them unfairly. The variable they’re missing is the 5-10 year head-start (late elementary, middle and high school), with compounding learning and training, that high-achievers typically leveraged before even arriving in college; virtually always driven by parents with high educational expectations of their young children.

Raw intelligence and effort are inputs. The market rewards outputs, and years of extra studying and training, especially during childhood and adolescent years that are dramatically influential on a person’s cognitive and social development, adds an enormous boost to any person’s output. That’s uncomfortable to acknowledge, and extremely challenging (if not impossible in many cases) to rectify decades later in life. But it is nevertheless the reality clearly visible in the market to anyone with their eyes wide open. If in college you suddenly decide you want to learn and play golf or basketball professionally, you may make it to the top if you are exceptionally talented and train like crazy. But more often than not you will find that other exceptionally talented players, who’ve also been playing the game competitively since they were 10 yrs old, will run laps around you.

Industries like tech and law may be different in the sense that there are far more “slots” to make a comfortable middle class living, but the requirements and challenges of making it to the top – a wealthy entrepreneur, an elite managing partner – are far closer to those of professional athletes. Simplistically demanding “representation” at this tier of the economy is as vacuous and fruitless as expecting the NBA or the PGA, or perhaps more appropriately the Olympic Committee (business is international), to adopt affirmative action quotas for “proportionate” ethnic representation. Given the constraints and demands of international competition, there is no HR department or recruiting committee with power over who can fill these positions. Once you step onto the field, into the arena, or into the C-suite, there is only performance today. The scoreboard or financial results make everything else secondary.

Promoting diversity in tech entrepreneurship and startups is an extremely noble and good goal. I support it. Wholeheartedly. But for the love of God, let’s please be honest, decent, and smart about it. If we’re honest, we’ll first acknowledge all of the nuances and complexities – some of them clearly uncomfortable – about the background sources of the problem. We’ll also acknowledge that extremely competitive industries – like venture capital – are heavily incentivized to look for and exploit “undervalued” talent. Literally hundreds of funds, many of them led by people hardly from the kinds of backwater places simmering with racism, are all competing to the death to find successes. If they still are not substantially moving the needle on finding numerous tech ventures led by teams of underrepresented color capable of generating venture returns, maybe racism isn’t the real problem.

Second, if we’re decent about it, we will not play this unfair game of simply looking at a team or portfolio, finding that there’s no one “of color” on it, and throwing a racist label at someone. We will stop weaponizing diversity. Many recruiters in certain high-performance industries know how much extra effort it can take to find truly high-performing “diverse” candidates. It is not because they do not exist. It is because they, for all of the discussed reasons, are in shorter supply; and because they are in shorter supply, they get taken up by employers with the best brands and compensation packages. When a particular A-level firm – whether it’s a law firm or a venture capital firm – loudly promotes their “diverse” roster, it does not mean every company with less “diverse” rosters is full of racists. It means that in a market increasingly looking for these scarcer candidates, those with the most “pull” (better brand, better pay, lower risk) are able to win, and those with less pull lose. In many cases “inclusiveness” has absolutely nothing to do with it.

This last fact is a real problem with arguing simplistically that “more diverse teams outperform.” Of course if you hire meritocratically from the broadest pool of talent (including all ethnicities and international talent), you are going to get more high performers. If we count the full spectrum of ethnicities and nationalities, together with gender diversity, in “diversity” (broad diversity), the argument that diversity improves performance is almost certainly accurate. It’s the story of American immigration and outperformance. Even Silicon Valley is extremely “diverse” in this sense. Bigger talent pool, more meritocracy. But people who use that data to then justify weaponized diversity initiatives for specific under-represented groups (narrow diversity, just URMs) are engaging in a sleight-of-hand with the term “diverse.” There is no data suggesting that early-stage founding teams comprised of those specific groups outperform.

If we expand the discussion to later-stage teams hiring employees (not entrepreneurs or senior executives), the causation between “diversity” (in the narrow sense of URMs only) and performance can easily run in the opposite direction. The highest performing companies raise from the most prestigious funds, pay the best, and are able to absorb the high-achieving under-represented minorities in the talent pool. Because high-performing URMs are, for the discussed reasons, in more limited supply, lower performing companies have fewer to recruit; thus top companies are more “diverse”, and lower-tier companies are less so.

All of these attempts at using misapplied data to force overly-aggressive hiring of under-represented minorities are at best unhelpful, and at worst disingenuous; and they distract us from addressing the real problems behind under-representation. I cannot stress this enough: our unwillingness to openly talk about the uncomfortable reality, and instead continue with the same “we just need to try harder at ending racism” stories, is exactly why we are making so little progress.

Relatedly, the weaponization (and in some cases monetization) of diversity heavily incentivizes tokenism. As long as I can secure enough people who, from outer appearances, check the “diverse” box, I can move on and totally avoid actually addressing the systemic issues that demonstrably disadvantage certain people over others, i.e. actual poor people. For example, many latinos at elite universities are the children of doctors, lawyers, and executives, from stable homes and private prep schools. Are these really the “diverse” candidates we want to pour substantial resources into helping? Does a Jose who summers in the Hamptons and got a BMW for his 16th birthday bring “color” to your workplace in the way diversity initiatives intend? Maybe. But if that’s what we really want, let’s be honest and open about it. Filling your workplace or portfolio with people from objectively affluent and privileged backgrounds, who nevertheless have the right names or skin tones, feels different to some of us than really putting in effort to level the playing field for people facing real structural barriers.

Finally, if we’re smart about diversity in high-performance areas, we’ll acknowledge how important patience is. Instead of pretending that a few well-intentioned initiatives are going to suddenly erase decades and even generations of differences with compounding effects, we’ll start going after long-term policies that will really change the landscape. Policies like:

-equalized public school funding and school choice
-funding for schools to engage with low-income homes and communities on educational culture
-public daycare and pre-K
-criminal justice reform
-public funding for healthcare, including mental healthcare
-social and economic support initiatives

Evidence is mounting that the charter schools most successful at breaking cycles of poverty, and closing the early achievement gap of URMs (which widens over time when left unaddressed), are those that go well beyond educational instruction; directly engaging with parents and households to instill a culture of high educational expectations. Achieving results requires intervention into household environments, and that requires letting go of our misguided and self-defeating fears of discussing family cultural differences.

Recklessly and indiscriminately warmongering over diversity is the business world’s equivalent of breaking windows and looting. The anger and frustration over the slow pace of results are understandable and worthy of empathy. And yet angrily pointing fingers at people who are sincerely trying to improve an issue that they really did not cause, and in truth are very limited in their ability to quickly fix, is counterproductive. If we push them to promote candidates who truly are not ready, the resulting underperformance will not only ruin the confidence of people who otherwise might’ve had very positive outcomes in a more appropriate environment, but it will also harden stereotypes that we should instead be, strategically, weakening.

For too long we’ve allowed discussions of diversity in tech and other high-performing professions to be hijacked and unjustifiably dominated by those who want us endlessly distracted by searching for racism and systemic discrimination as the supreme, seemingly supernatural explanation for all our challenges; and who at times see a profitable opportunity in that distraction. Their often vitriolic refusals to even engage in respectful substantive discussion about other explanations, and other solutions – including long-term policy solutions – are, unfortunately, a significant reason why our community is stalling in its progress.

I’m thankful every day that the decision-makers I encountered throughout my life didn’t just see “a latino.” They didn’t see a stereotype to be quickly discarded, nor a token to be pushed in directions driven by a political agenda. They saw Jose Ancer – a specific kid with some challenges but also some abilities – and gave me a shot at showing what I could really deliver within the background and life I was actually living. We should want nothing less for every single child that enters the school system, and adult that enters the market. How many individual people are we failing to objectively help, because we are paralyzed by grand theories chasing rushed collective goals that have never been feasible on any short timeline?

Results over misdirected rage. Adult discussion over childish tantrums. Equal opportunity over unrealistic expectations of quickly equal outcomes. But getting there requires all of us to talk honestly, empathetically, and carefully about the real issues, without demonizing those who sincerely feel like we are spinning our wheels. That’s the only way we will finally get past the anger and frustration that understandably result from misguided quick fixes that ignore the complexity and depth of the challenges.

I want to see, on top of the public policies that directly address the social and economic challenges of poverty in America, an environment in which every young latino can throw him or herself into whatever subject they want, and make long-term sacrifices to succeed, without facing labels like “coconut” or other counterproductive messaging from other latinos that children from other ethnic backgrounds simply never have to face. We absolutely know how to work hard, but as it relates to high academic and business achievement, we too often celebrate working on the wrong things, and wait too long to correct course.

Without a doubt, let’s ensure we’re rooting out whatever racism and non-meritocratic discrimination that exists in our high-performance industries. I’m sure some does, though we too often exaggerate (dramatically) its explanatory power for disparities in outcomes. Importantly, we also shouldn’t deny the personal responsibility necessary in our own communities to evolve our identities so that no child is ever forced to choose between high achievement and culture. In doing so, we must not forget to support socioeconomic and educational public policies that can legitimately level the playing field for everyone.

The evidence is nevertheless quite clear that no amount of public policy or reconciliation over historical injustices will ever replace the profound, long-lasting impact of private household cultural values, including about education and long-term training, on the performance level children are able to reach as adults. Sometimes the very hardest problems are the ones that no one else can fully solve for us. Yet at the same time, there can be hope in realizing that many of the long-term solutions are much more in our control, and we don’t have to wait for outsider heroes to be our saviors.

It’s time for the most honest among us to demand that the level of diversity discourse be elevated and civilized; above the yells and sand-pounding of those who continue pretending that the key to increasing true high achievement in our community lies in another inclusiveness seminar, another infantilizing apology from a colleague, or another lecture from self-appointed “experts” on our universal, never-ending victimization. The truth is that it lies far closer to our communities, our families, and our homes.

On a closing note, I was careful to keep this discussion personal, and about my own experiences as a latino. I don’t pretend to speak in any way for other minority groups; and certainly not for the black community, which has faced a very different and legitimately harsher historical reality in America. I cannot pretend to know what it is like to be a black American, or to fully understand the incredibly justifiable outrage sparked by George Floyd’s murder. This essay was not at all about police brutality, for which there is seemingly limitless evidence, or well-documented racism and discrimination in segments of society outside of tech entrepreneurship and other high-performance career paths. It by no means is an argument that we live in a perfect, fully meritocratic world; but rather a personal observation and reflection on whether we are completely missing the mark on the real reasons – or at a minimum, the most impactful reasons – why certain groups, like American latinos, remain so under-represented in the very high-performance, high-risk world of tech entrepreneurship.

I do hope, however, that some of my thoughts might be helpful for other people of color to assess and chart their own paths on the issue of diversity, and what changes they hope to effect in the market. I hope we will no longer allow legitimate voices and perspectives to be silenced in favor of the same mono-narrative that wastes precious time and fails at delivering durable results. Anger and frustration can be fuel for enormously productive action, but only if we channel them in ways that truly hit the source of a problem; even if that source is more complex and uncomfortable, and less responsive to simplistic outrage and politicization, than we want to admit.

Post-Script: The following is a shorter, more practical post targeted toward CEOs and Boards of startups, on how they can respond constructively to “weaponized” diversity attacks in the market: Diversity in Startups: Whining, Warring, Winning.

Legal Office Hours for Remote and Distributed Startups

TL;DR: Though I work with all kinds of startups in various locations, I’ve become particularly interested in, and connected to, the distributed/remote startup ecosystem; and decided to throw in a few hours of my time each week to support new teams growing specifically under that model via free virtual office hours. Info on that is near the end of the post.

Over the past several years, I’ve become fascinating with the idea of a startup ecosystem largely detached from geographic constraints, with companies recruiting talent based on fit and merit, regardless of where they live. For years I lived in the Hill Country outside of Austin, barely ever working from the firm’s downtown office because I just didn’t see a need to; and my clients didn’t care. Highly regarded Startup Lawyers don’t really need to spend much time in coffee shops or conventional offices. All they really need is a solid internet connection. Sidenote: I think Elon Musk’s StarLink (high-speed broadband anywhere) could be a game changer for the gorgeous Colorado mountain towns around where I presently live.

As my family – particularly my wife, who grew up in SoCal – realized that my growing client base didn’t care at all about my physical location, their willingness to continue putting up with Austin’s mosquitoes and deadly snakes (big problem outside of urban core), humidity, horrible traffic, decidedly limited outdoor beauty (save for a lake) and seemingly endless scorching summers (Mid-May through mid-October really sucks) reached a breaking point. Austin is an amazing and thriving city for many reasons, but it is not for anyone who likes needs the outdoors. No city is for everyone.

Because my wife and I had already decided to homeschool our three young kids, we had almost total freedom to pick a destination; and ultimately we landed on living near the mountains about an hour outside of Denver. Amazing weather and mountain views, literally limitless outdoor recreation, and a short flight or road trip to almost anywhere we needed to go. And yes, still rock solid broadband so I can close deals and work with clients just as easily as I did before. Little did we know that with both “homeschooling” and “remote” work, we’d started riding waves that would suddenly turn into a massive tsunami because of a pandemic.

I bring up this background to highlight how escaping the “tyranny of geography,” and the growing comfort with distributed startup teams, is not just an intellectual curiosity to me; it’s a core part of my life. When we’d announced that we were leaving Austin, there was no shortage of people who thought I was absolutely nuts and lighting a match to my legal career. They didn’t know I’d already been living in “the Texas countryside,” with a thriving ECVC client base and firm, for years. If my clients – all scattered across the U.S. and world – didn’t care that I was living on acreage in the Texas hill country, I knew they wouldn’t care about my living in the mountains of Colorado.

As our own adventures with remote/distributed work have continued, I’ve watched the broader ecosystem of “remote” startups mature as well. The number of companies using a distributed team, with few if any people in the Bay Area, has grown exponentially over the past 5 years or so; and we’re also increasingly seeing institutional investors who are happy to “venture” outside of their local markets in search of high-potential businesses that aren’t on the classic Silicon-Valley style VC circuit. Suddenly the distributed startup ecosystem has moved from a fringe quirk to a desirable asset with distinct competitive advantages.

But there’s one distinct disadvantage of “remote” startups that I keep seeing come up over and over again: they don’t connect as easily with serious lawyers. Most ECVC (emerging companies and venture capital) lawyers are still heavily tied down to local geographies, particularly the Bay Area. Strong teams in non-traditional markets often end up either using nearby lawyers who are totally lacking in the appropriate expertise/specialization, or they just wait until their investors happily “recommend” their favorite $1,000/hr Bay Area lawyer whose firm represents Uber and Apple. People who read SHL regularly know that I’ve discussed ad nauseam the deep problems (conflicts of interest) with using your investors’ pet lawyers; and also how the Bay Area market often promotes norms/practices (“unicorn or bust”) that are a poor fit for “normal” startups.

As I’ve been living through this pandemic and watching the growing zeitgeist around distributed startups, it occurred to me that I’m in a place where I could contribute some of my time to supporting the ecosystem. So I’ve decided to allocate a few hours of my time each week to free virtual “office hours” specifically for distributed teams. We can spend, via a phone call or Zoom, up to an hour talking about any legal/strategic issue on the team’s mind: formation, founder relationships, fundraising and structuring, governance, hiring, etc. No expectation of billing or future engagement. I really just want to get more visibility into how this growing ecosystem is evolving, and how existing market players can help it thrive.

My personal thesis is that America’s size and unique geo/climate diversity is an enormously under-utilized asset in tech. Why should entrepreneurs and employees be forced to live in a handful of narrow, crowded, and increasingly over-priced concrete jungles when there are an endless number of beautiful, affordable, perfectly livable places that need high-potential residents but just don’t have the “tech” base to employ people locally? Because of some nonsense about the importance of “body language” and regular in-person meetings? Please. I think this pandemic is not just helping everyone realize the superficiality in some of their assumptions about remote work, but about a lot of virtual interactions: education, healthcare, and even connecting with the investor community.

A secondary thesis of mine is that the more geographically diversified a startup team’s network becomes, the less exposed they are to local startup power politics. Every geographically constrained ecosystem has organizations that have consolidated a level of local influence/control so high that it can feel like you need to kiss a brass ring in order to access resources you need. That dynamic is the opposite of what a real ecosystem should be; a decentralized resource where no single player can play gatekeeper and extract more value than their own value-add really merits. Promoting a more distributed startup ecosystem reduces the influence of overly self-interested power players, and enhances the kind of transparent meritocracy that helps teams access the right people with minimal wasted time.

Startup ecosystems are ultimately about relationships and people; not about artificial city or state borders. It’s time we talked more about the American ecosystem, and freed entrepreneurs and talented employees to work and live wherever is best for their companies and families. In the process, we’ll spread economic opportunity further across the country, and reduce many of the ills that have resulted from cramming people into too few of cities with not enough space and resources to make “living” affordable and accessible.

Summary of my background: Practicing over 10 years exclusively in emerging companies and venture capital law. Honors graduate from Harvard Law with various awards. Over half a billion in transactions covered, including with top VCs like a16z, sequoia, accel as counterparties. Built out one of the top elite ECVC law practices as managing partner.

Info on participating in virtual legal office hours for remote/distributed teams:

My LinkedIn Profile

Shoot me an invite request on LinkedIn (preferable), or send me an e-mail at [email protected].

Criteria (please explain in intro connection how you meet the below):

  • You already have, or expect to have, a distributed team. Not a 1 or 2 people that you “let” work remotely, but a full orientation around enabling remote work such that no one outside of whatever you might call “HQ” is disadvantaged in opportunities, because the whole team is included in events/meetings. It is fine to still have an informal HQ in the Bay Area, or other classic markets like Austin, LA, Seattle, NYC, etc.
  • The market you are going after has a credible shot at producing an at least $50 million (enterprise value) business. Unfortunately my domain expertise is really poorly fitted for mom-and-pop style businesses, or small apps.

This isn’t any kind of formal program with a hardened schedule, because my own availability varies day to day with deal/client work and firm admin, and I’ll scale my time allocation up or down as the number of teams fluctuates. Some of these calls surely will (and have) turn into long-term client relationships, but that is most certainly not an expectation here. I find no-agenda discussions with new founding teams extremely fun.

Independent Counsel in an Economic Downturn

TL;DR: In all parts of an economic cycle, up or down, there is significant value in having independent (from investors) strategic counsel that you can trust to protect the common stock in navigating negotiations with investors who are 20x as experienced as the founding team. In a downturn, however, the number of “company unfriendly” possibilities in deal and governance terms goes up ten-fold. That means the value of independent, trustworthy counsel shoots up as well.

Background reading:

I’ve written multiple posts on the topic of how first-time entrepreneurs place themselves at an enormous disadvantage when they hire, as a company counsel, lawyers with deep ties to their lead investors. To people with good instincts, the reasons are obvious, but for those who need it spelled out:

A. First time entrepreneurs are regularly interacting, on financing and governance issues, with market players who are (i) misaligned economically with the common stock, and (ii) 20x as experienced as the management team and largest common stockholders. They rely heavily on experienced outside advisors to “level the playing field” in the negotiations.

B. One of the most impactful strategic advisors an early set of founders/management can look to for navigating this high-stakes environment is an experienced “emerging companies” specialized corporate lawyer (startup lawyer), who (if vetted properly) sees far more deals and board matters in any given month than many sophisticated investors see in an entire year.

C. Because investors have contacts with/access to lots of potential deal work, and corporate lawyers need deal work, aggressive investors have come to realize that their “deal flow” is a valuable currency that can be leveraged with an overly eager portion of the “startup lawyer” community; shall we say, “nudging” them to follow the investors’ preferred protocols in exchange for referrals. By pretending that only a handful of firms have credible/quality lawyers, they also try to block law firms with more independent, but still highly experienced, lawyers from getting a foothold in the market.

D. Founders, because they lack their own contacts and experience vetting lawyers, often find themselves influenced into hiring these “captive” lawyers. As a result, they are deprived of some of the most strategic and high-value guidance that smarter teams are able to tap into for protecting the common stock.

For a deeper dive into how this game is fully played out in the market, read the above-linked posts. The point here is not to promote an exaggeratedly adversarial take on startup-investor relations, but to emphasize a simple reality of how things really work.

The main point of this post is: in an economic downturn, when company “unfriendly’ terms are going to be far more on the table than they were in years past, the value of independent strategic counsel is magnified ten-fold. In go-go times when competition for deals and excess amounts of capital shoot valuations up and “bad terms” down, deal terms gravitate toward a closer-to cookie-cutter, minimalist kind of flavor: good valuation, 1x liquidation preference non-participating, minimal covenants, and sign the deal.

That doesn’t mean there’s really a “standard” – I’ve also written extensively about how saying “this is standard” has become the preferred method for clever investors to trick startup teams into mindlessly signing docs that are against their company’s long-term interests. But, in good times deals do tend to start looking a lot more like each other in a way that makes negotiation a little easier.

But when there’s an economic shock like what we’re experiencing right now from COVID-19, and the investor community starts to improve in their leverage, it’s inevitable that you start seeing a lot more “creativity” from VCs with terms: higher liquidation preferences, participating preferred, broader covenants and veto rights, more aggressive anti-dilution, tighter maturity dates on convertible notes, etc. etc.

In this environment, it is incalculably valuable to have people to turn to, including independent deal lawyers, who can tell you what really is within the range of reasonableness, what to accept v. push-back on, and generally what is “fair” given the environment you’re fundraising in. Independent counsel will help you protect the common stockholders, while granting your investors some terms that you may not have needed to accept a year or two ago. Captive counsel, however, will know that his/her “good behavior” (for the investors) in structuring the terms will ensure more deal flow from their real clients. And because most startup teams are understandably lacking in market visibility, they have no way to quality-check the advice they’re getting. Trust is everything here.

Research and diligence your legal counsel just like how you’d diligence any high-stakes advisor. Importantly, ask them what VCs they (and their firm) represent and/or rely on for referrals. They may be great, very smart people, but if the answers you get make it clear that they are closely tied to people likely to write you checks, find someone with more independence. A muzzled corporate lawyer is ultimately an over-priced paper pusher.