Post Category → Startup Law Firms

Legal AI and the Future of Startup Law

It’s been a while since I’ve written on legal tech and startup law, and given recent developments in AI, it feels like an update is in order. For context, I’m a Partner and legal CTO at Optimal, an elite boutique law firm focused on ECVC, M&A, and Tech Transactions for VC-backed startups. We’re about 20 lawyers, company-side focused, and negotiate across from all the top VCs (and lesser ones too) and the usual suspects of Bay Area and NYC-based BigLaw.

Over the past two years I’ve reviewed and/or tested a tremendous number of new AI-based legal tech products that have hit, or will soon hit, the market. The notion that the new generation of LLMs will make a material impact on the legal industry is accurate. The capabilities being released go well beyond the typical automation tools that law firms have been integrating over the past decade or so. Lawyers of all stripes are going to get a lot more productive.

However, what’s also become clear is that (predictably) shysters are coming out of the woodwork, exaggerating where this new tech is going and what can be done with it. For just one example of that, see this X thread. Given what I’ve observed over the years regarding the very short-term memory of the entrepreneurial ecosystem, I am not surprised at all that, thanks to AI, we are going to see the second, third, fourth, and on and on attempts at building the same flawed and untenable business model of some supposed new kind of law firm or legal service provider infused (somehow) so extensively with super-advanced technology that they dominate and transform the industry.

Alas, it’s just not meant to be, even if many of us tech-forward lawyers eagerly await every new tool that makes legal practice faster, smoother, more productive, etc. For those who don’t remember, Atrium was the most visible failed attempt at building the tech-driven startup law firm “of the future.” There are a lot of views out there for explaining why Atrium failed, some (in my opinion) more honest than others. I’ll summarize my views here:

A. It was controlled by a founder (Justin Kan) who, despite being extremely successful and brilliant in his own way, not only didn’t understand the real drivers of the elite legal industry – on the supply or demand side – but had no real interest in learning them. He assumed that his personal brand had enough gravitational pull to cover up impossible economics and a weak value proposition dependent on exaggerated technology capabilities.

B. Kan also assumed that his connections with Y Combinator, which funneled both cash investment and portfolio companies to Atrium, amplified his pull even further.

C. Not nearly discussed enough, Atrium’s organizational structure hid massively problematic ethical conflicts of interest that were a ticking time bomb. Company counsel, what Atrium purported to be, is supposed to help startups negotiate against VCs, serving as an equalizer for entrepreneurs and other common stockholders negotiating super high-stakes contracts and board decisions with financially misaligned elite counterparties. Yet Atrium was funded by the VC community, had VCs on its Board, and used all of those connections to funnel portfolio companies of its investors (including YC) into its client base.

In short, over-confidence and naivete, vaporware technology, and a go-to-market strategy dependent on pretending professional rules around conflicts of interest (for protecting clients) could just be hand-waived out of existence.

I could go on and on about how doomed Atrium was from the start, including how it depended on inexperienced de-skilled (read: no real partner oversight) young lawyers dreaming of VC-like payouts, and how its fixed-fee pricing model itself incentivized rushed work and not properly serving clients. But this post isn’t about Atrium; it’s about the people who are going to be using AI vaporware to try to resurrect it.

The narrative emerging today is something like “Atrium was just too early. Now, with AI, is the right time.” I’m sorry, but it’s really not. Even if the new generation of legal AI is more powerful than what Atrium was building – and it is – nothing coming down the pike of legal AI with the current generation of algorithms is going to be so transformational as to overcome all of the other flaws of the business concept.

At the low end of law, I can certainly see new legal AI creating something like a more dynamic version of LegalZoom, backed by highly de-skilled humans shuffling paper around in the background. But this wouldn’t be that transformational, because legal automation has already been eating up the bottom two quartiles of the legal industry doing work like small business law, simple divorces, estate planning, low-stakes dispute resolution, etc. It’s why the majority of law graduates today, even many from decent schools, can barely earn enough to pay their student loans. Sidenote: I think about half of law schools should just be shut down if they can’t find a way to operate at half the cost or less.

Startups even have their own LegalZoom: Clerky for the very earliest pre-seed stages, when everything can most easily be cookie-cutter. It works great in many (not all) very early-stage contexts, and many lawyers, myself included, integrate with it.

But unlike automation tools, we (VC-backed startup lawyers) play at the elite end of law, where the stakes are much higher, and the context on the ground is far more variable and complex.

The new LLM-based generation of legal AI tools are going to make elite lawyers much more productive. We already see it happening within our own firm, and it’s influencing hiring decisions, particularly on the junior side. They will make drafting, document review, research, and other lawyer work meaningfully more productive to the point of probably shrinking the footprint of elite firms, concentrating earnings further toward the top as the real “mandarins” of elite law don’t need nearly as much on-the-ground junior labor to serve clients.

But the notion that this new technology eliminates the need for those legal mandarins – the people who not only have the years of technical training, but also the personal understanding of the client and the mix of IQ/EQ to apply legal + strategic insight to unique dynamic human contexts, is preposterous.

There is simply no way to use AI (with presently attainable capabilities) to de-skill this top end of the industry such that a new organizational structure full of lower-paid “legal technicians” can actually deliver what clients want, at a quality level that doesn’t touch malpractice. This generation of AI will, as it plays out, be the equivalent of armies of tireless and supernaturally fast paralegals and junior lawyers, at a tiny fraction of what the human equivalent would cost.

Super valuable. But as anyone who has actually worked in legal (or the military) knows, even the largest and fastest infantry can be useless (even dangerous) without sufficiently smart hands-on strategic leadership. Interesting theoretical discussions on new AI algorithms point out that even if AI isn’t really “reasoning” in an abstract sense (it’s not), many lower-end white-collar workers aren’t either. I actually agree with that, even if some find it insulting (sorry).

But the elite lawyers in high-end law firms? They’re being paid to actually reason in complex high-stakes ways that no present AI breakthroughs anywhere on the horizon, in university or corporate research labs and certainly not in the market, can supplant. That being said, their work is also embedded in workflows that include numerous mundane (boring) tasks they’d gladly outsource to a diligent and reliable tool. This is why literally every single elite law firm is working on integrating AI right now.

Hardly luddites, they understand this tech is going to make their partnerships much more profitable, while improving efficiency for clients. It’s also going to make it a lot harder for junior lawyers to enter elite ranks. Such is life in the race against the machines, or perhaps better said: against the mandarins using machines.

The shysters that will be peddling AI to create pretend startup law firms and alternative legal services will be taking one of a few (predictable) strategies:

They will exaggerate the extent to which elite legal work is or can be standardized, because their unit economics can’t work without hyper standardization.

See Standardization and Flexibility in Startup Law. VC-backed tech companies going after 9, 10, and larger-figure opportunities are not coffee shops. They all operate in different competitive contexts, with different investors, different growth expectations, different team cultures, and all sorts of other contextual dynamics that influence their approach to legal and Board issues. This is why even at the earliest stages Founders CEOs talk to human lawyers.

You see this play out with other automation tools that have tried (and failed) to hyper-standardize startup law: see Carta. They know their technology breaks down beyond a small level of parameters, and so they try to get clients (Founder CEOs) to believe that narrow set of parameters is all they need. But the ROI – millions – for actually negotiating contracts (flexibility) is often so high that only the most foolish entrepreneurs trust their key decisions to an automation tool.

They will de-skill their rosters in order to create margins (potentially) attractive to investors, while covering up the (significant) drop in quality.

The most expensive people at any law firm are the Partners, just as the most expensive people at a hospital are the top doctors, all for good reason. They are the ultimate quality control in a service where low quality is extremely expensive, even dangerous.

Elite law firms are built, funded, and run by a hybrid form of capital – elite Partners. They provide the financial capital, but also the extremely nuanced technical knowledge required to train and run the operation: professional human capital.

If you just layer investors, like VCs, onto this model you are not going to have a competitive advantage in the industry. Too many mouths to feed, and not enough margin. So entrants, like Atrium, rely on de-skilling – eliminating real (highly skilled) Partners, and trying to convince clients this doesn’t result in a drop in quality.

What will a drop in quality look like? Rushed (or non-existent) negotiation. Poorly thought-out legal strategy. Technical errors that even the best LLMs just aren’t algorithmically capable of catching, but now without senior expertise to correct them.

Law firms are far lower margin relative to the kinds of tech products funded by VCs. There’s no real magic to trying to create VC-like margins in professional services. It requires getting rid of a lot of the most elite talent, because that’s where the money (rightfully) goes. In healthcare, this can work at the low end (de-skilled), like nurse practitioners using tech to treat sniffles faster and cheaper than GPs. In high-end specialty care, it can be (and has at times been) disastrous.

They will be funded by, and partner with, ecosystem players who profit from a drop in the quality of legal service provided to startups.

This is exactly what happened with Atrium, which relied extensively on pushing so-called “standards” created by Y Combinator, an accelerator and VC, because YC funded Atrium, sat on its board, and pushed a lot of its portfolio companies to use Atrium. Unsurprisingly, those standards were designed to benefit investors financially, which means they cost entrepreneurs significantly, far more (orders of magnitude) than whatever they “saved” in legal fees.

This is fundamentally what so many people in the startup ecosystem misunderstand about the role of company counsel, and some even put in effort toward ensuring entrepreneurs don’t understand it. Startup Law is, at a foundational level, adversarial* and (unavoidably) zero-sum. See: Negotiation is Relationship Building. Many people want to pretend otherwise, but at the end of the day institutional investors and common stockholders see the world differently, have different goals (often), and in an exit the money can only go into one pocket or the other.

One of the most clever things I observed about how Justin Kan structured Atrium is it offered his investors a double value proposition. The first was obvious: we’ll build this supposedly massively disruptive whiz-bang-pow legal tech firm. But the second one was more subtle: send your portfolio companies our way, and we’ll ensure they negotiate the “right” way and sign the “right” contracts – meaning the ones that make more money for and give more power to… those same investors.

A brilliant move, even if profoundly illegal (it flouted rules against conflicts of interest), and ultimately not enough to overcome the bigger business model flaws. Too many smart entrepreneurs – fools can always be tricked – saw through the charade and weren’t willing to bite. I expect the same to happen with the new generation of Atriums that will be attempted in the ecosystem.

Fiction: New LLMs will disrupt the legal industry, paving the way for entirely new organizational structures taking enormous amounts of business from the old guard.

Fact: At the bottom end of the market, new legal AI will incrementally allow existing automation providers to move up-market, perhaps from the 40th percentile to something like the 50th or 60th, but nowhere near the elite firms that are most-often talked about. At the high end, everyone and their mother is working to adopt legal AI into their existing firms. Elite firms will likely be smaller and more profitable, but still very much headed by elite legal mandarins wielding more powerful productivity tech.

Post-script on Healthcare: A brief point about the new generation of AI as it applies to healthcare, perhaps the field most often compared to elite law. From my vantagepoint, I expect AI to be much more impactful in the long-run to healthcare than law, for reasons I will call (i) less competitive subjectivity and (ii) more compartmentalized service.

What I mean by less competitive subjectivity is that in healthcare the goals are more straight-forward – treat/heal the patient, and the playing field is much more standardized: biology. More straightforward goals and (relatively) uniform biological science lend themselves much more towards the implementation of algorithms and high-volume data crunching. In elite law, however, the goals are much more subjective and contextual: there are multiple players, often with their own worldviews and strategic priorities. Further, every company is very different. Different people, industries, business models, etc. EQ and human-oriented “reading the room” play a much bigger role here, and I believe that limits how far technology – in its currently developing iteration – can go in displacing humans as opposed to augmenting their productivity.

By more compartmentalized service, I mean that healthcare breaks down into much more discrete tasks that can be walled off and modularized, outsourced entirely to third-parties and technology, and then re-integrated into the patient’s treatment without a problem. Think blood labs, diagnostic testing, monitoring, pharma, etc. Elite law just doesn’t work that way for a number of reasons – largely having to do with the more contextualized and subjective nature of the work, which amplifies the friction involved in integrating third-parties lacking the full context of the “patient” (the client). This is why in healthcare I expect to see a flourishing of third-party AI-centric services woven into the market, whereas in legal far more of the development will be tools for law firms.

* When I speak of ECVC law as being “adversarial” I mean in the technical sense. It is (obviously) not to suggest overtly hostile intentions or behavior, but to acknowledge openly and honestly that there are numerous zero-sum issues on which entrepreneurs (and their employees) are misaligned with investors, and each constituency is maneuvering in order to gain an advantage. When certain players suggest that it is “no big deal” for lawyers representing companies to have close relationships with the VCs investing in those same companies, I consider that little more than a rhetorical sleight-of-hand to give investors a tremendous negotiating advantage. See Negotiation is Relationship Building. 

Lessons from Elon Musk (Mistakes) for Startup Governance

“Thou shalt have no other gods before Me.” – The 1st Commandment

This post is going to discuss certain high-stakes financial happenings with one of the great heroes of the Startup / Tech Ecosystem of recent decades, and indeed someone I deeply admire for his technical acumen (political opinions are more hit and miss): Elon Musk. Depending on your orientation, I might even be called a “fanboi.” I am particularly a big fan of his achievements at Tesla and SpaceX, as well as his efforts (however imperfect and ham-fisted) to reorient X fka Twitter toward a more free speech philosophy.

Elon Musk had his hand slapped big time by Delaware courts, having his >$50 billion Tesla compensation package annulled for lack of appropriate Board governance and process. He is now very angry and campaigning to have Delaware dethroned as the international destination of choice for corporate law. His view is that Delaware has treated him unfairly by overriding the choices Tesla’s Board, clearly controlled by him, chose with respect to determining Elon’s compensation package.

On numerous occasions I’ve heard Elon referred to, particularly among startup players, as a “god.” That is understandable, because his technical and business talents certainly get close to once-in-a-generation ultra ultra elite level. An apex Navy Seal of an entrepreneur.

For that reason, I included the 1st commandment above. Completely putting aside religious theology, the intellectualized interpretation of the 1st commandment goes something like this: do not deify – in the sense of treating as infallible and entitled to unconstrained deference – something or someone that doesn’t deserve it; which is to say no one and nothing deserves complete worship like “God.” Everything and everyone, no matter how good in a particular context or domain, has limits and points beyond which they need to be constrained, lest very bad things begin to happen.

Inarguably (I think) good advice. Only the naïve treat talent within a specific technical domain – legendary impressiveness notwithstanding – as reason for a single person (or even group of people) to override the 100s of other kinds of expertise and talent that the world also depends on.

As someone who’s worked deeply for over a decade in various startup ecosystems, watching numerous companies rise and fall (for all kinds of reasons), I’ve come to analogize entrepreneurial energy to something like uranium, gasoline, or the sun. All highly concentrated, tremendously powerful sources of energy. The core drivers of the economy. Immensely valuable and important.

And yet, used in the wrong way, without appropriate processes, checks and balances, they kill and destroy: explosions, cancer, apocalyptic painful fire. It takes an appropriate system to channel that energy into something productive and valuable. Our sources of entrepreneurial energy deserve tremendous respect and freedom – something which American culture is uniquely good at, but they’re not gods. They too need refinement and constraints, or they’ll kill us (or at least wastefully burn enormous amounts of money).

Notice the word system in the term startup ecosystem. What has turned the world of American venture-backed startups into an economic powerhouse that is envied by the world is not, and never has been, simply bowing to entrepreneurs wholesale, giving them 100% unconstrained power to build whatever and however they see fit. The actual startup ecosystem has never deified genius entrepreneurs. Instead, it has placed their energy and talent within a dynamic, evolving system of independent forces, each with their own guiding principles and incentives, that shapes and channels that energy into world-changing enterprises.

Professional venture capitalists – not the unbundled dumb money funds swirling the ecosystem in recent years but actual professionals with deep networks and expertise about startup and growth playbooks – are one example of a countervailing force on entrepreneurs. You will hear propaganda in the market suggesting that all VCs are useless and just waste time beyond their willingness to write checks, but this is self-evidently false from even a half-hearted review of the history. Numerous household names in tech were deeply shaped by elite VCs coaching, guiding, and even constraining entrepreneurs when experienced judgment suggested doing so was necessary to keep the energy flowing in a productive direction.

That is not to overstate the role elite VCs have played in the ecosystem. They too are not gods, and absolutely need their own constraints and monitoring to avoid excesses. Many of them are at least as mercenary and capable of financial destruction as the hyper aggressive entrepreneurs who make headlines. But they are a valuable and necessary part of the system that shapes entrepreneurial energy into our elite economy.

Other not-quite revered but still important forces in the ecosystem include lawyers – representatives of the legal system for protecting and aligning interests in a high-stakes economy of diverse players acting as fiduciaries for huge amounts of money – and accountants (auditors) also play an important role. Employees as well. Accelerators, despite their overall decline, are also worth mentioning even if fundamentally they are just VCs of a particular flavor.

The startup ecosystem as we know it is built by setting these players – these forces – to interact, engage, and when appropriate constrain each other. These different constituencies of players do not need to like each other to engage productively – you’ll regularly hear VCs, for example, whine about lawyers. That’s because lawyers on the side of startups very often prevent aggressive VCs from getting their way on contested company issues, when the overall governance calculus doesn’t warrant it. The semi adversarial way in which the players interact is by design; a feature, not a bug.

Imagine a weather system with different forces constantly swirling around and engaging, pushing and pulling, mixing, unmixing, and remixing. That’s kind of how an entrepreneurial ecosystem works. No single force – yes, not even ultra elite entrepreneurs – is so universally good and important that it should completely override all the other forces that have proven themselves time and time again as essential toward channeling all the energy toward a constructive, durable outcome.

Over centralizing such a dynamic ecosystem, allowing one set of forces to take over another, weakening the checks and balances, is usually bad for the market as a whole. One example of this would be venture capitalists controlling the lawyers who advise companies, biasing their advice on conflicted high-stakes issues. I’ve written about this quite a bit. Another example would be businesses hiring sycophants as legal advisors or accountants to misinterpret or misstate laws or financials, denying the open market the transparency and protections that the system has evolved to provide. We see this quite often as well.

The fact of the matter is that Elon had a kind of kangaroo Board of Directors, including his own divorce lawyer, his brother, and supposed “independent” directors who in fact owed much of their wealth to Elon and even vacationed with him; something which may seem innocuous in smaller cases but is material when the executive in question is one of the world’s wealthiest people and can fund some really nice vacations.

Thus when Elon’s compensation package and the process for determining it were reviewed, it was a joke. Amateur hour of the highest order, inappropriate for a Series B startup let alone a public company like Tesla. There was not even a feigned attempt at a professional process. Elon thought himself a god who didn’t need to listen to the legal system or lawyers. The Delaware Chancery Court, a global force in corporate law with tremendous gravitation pull, just gave him a reality check.

While Elon is understandably not happy about that, in the bigger picture it actually reinforces why the American business economy – and Delaware law specifically – is so respected internationally. Nothing says “rule of law” (music to the ears of high-stakes economic players responsible for ginormous amounts of other peoples’ money) like enforcing the rules against the (in this case arrogant) resistance of the wealthiest person on earth.

To be very clear, this is not to say that laws are all-important and inviolable all the time. Sometimes laws should be fudged, even changed. Uber is a great example of a company that thoughtfully broke some laws in order to improve them. Incidentally, it’s also an example of an entrepreneur (Kalanick) ultimately getting out of hand and smart VCs + lawyers playing a constructive role to get the business back on track.

Laws are, in many respects, like speed limits. We can always assume they’re going to be fudged on the margins, and yet where you set them still plays an important role for determining how far the fudging goes. Elon clearly went too far, pushing (metaphorically) 150mph in a 75 zone. However special of a person he may be, and however important his achievements, there is always a point at which the system simply cannot tolerate anyone setting such reckless behavior as an example.

The lessons here for startup governance are straightforward. Legal advisors should not be sycophants – they should not be beholden to the VCs or the entrepreneurs wholesale. The most aggressive players on either side of the table will very often try to hire gladhander advisors so desperate for the work that they’ll rubberstamp whatever, and yet somehow professionals with actual backbones and principles need to be allowed into the room. If the insiders don’t let that happen (because they are colluding), outsiders with their own lawyers will get it done for you, at much higher cost (just ask Tesla).

Founders sometimes misinterpret my writings about corporate governance and “independent” company counsel as suggesting that I’m going to just be a founder CEO’s lap dog. Being independent from the VCs so that company counsel can properly assist the Board in pursuing the interests of the common stock as a constituency (which usually includes all founders and early employees) is not the exact same thing as working for a particular founder. Usually those interests are all aligned, but not always, particularly when someone is excessively aggressive, immature, or uncoachable.

Independent directors should be meaningfully independent, not the CEO’s or the VC’s BFF. Credible processes for setting very high-stakes compensation matter. And no, simply getting a fragmented stockholder vote at the end to “cleanse” an otherwise horrible process is unlikely to be sufficient, particularly in cases fraught with time constraints, information asymmetries, and coordination problems among the stockholders.

This is also not to say that Elon did not deserve to be extremely handsomely rewarded for his spectacular performance as Tesla’s leader. I’m sure his compensation will still be very juicy. I’m sure it would have been juicy even if he had not consciously chosen a captive clown show as his Board governance model. Elon simply should have respected the process – the system – in which he was operating. He chose not to; a classic (quite common) case of an aggressive entrepreneur treating sensible legal advice as handwavy bureaucratic nonsense.

The system pushed back in a language that, short of imprisonment, even someone as powerful as Elon can learn to respect: lots and lots of money lost. Whether he likes it is irrelevant. That kind of assertive pushback is exactly what ecosystems must do in order to stay durable, dynamic, and not beholden to any single fallible, imperfect, definitely not a god player. To repeat: the system is designed to have power clashes. That’s part of how it self-regulates to avoid disasters. There is no other way of going about it.

Elite entrepreneurs are like the star players on the football team. Super important, deserving of reverence, fame, and lots of wealth, but they aren’t – they can’t be – above the game and rules (which can change and evolve) themselves, or the whole thing will collapse.

Corporate governance isn’t everything, but it matters, requiring constant monitoring and calibration to prevent conflict, collusion, and corruption. It has proven itself to serve a very important function in the startup ecosystem. Take it seriously, even if you’re an aspiring Elon Musk.

Postscript: You will notice plenty of VCs using this Delaware <> Musk case to pump up their “founder friendly” credentials on social media, decrying it as judicial activism and whatnot. Always watch incentives. When VCs feel like their own money is being wasted by an entrepreneur, or that their own portfolio company’s governance has gone off the rails, their first thought is “call our lawyers.”

But in this context, all their incentives are to give a soapbox speech about how they believe in founder-led companies and support Elon’s perspective. Costless marketing. I wrote in Trust, Friendliness, and Zero-Sum Games about the marketing dynamics of investors creating excessively “friendly” PR portrayals of themselves. It’s understandable, but founding teams shouldn’t fully drink the Kool-Aid.

The (Real) Problem with Carta for Startups

TL;DR: Carta has forever sold itself as friction-reducing “infrastructure” for the startup ecosystem. What this recent debacle around shady secondary sales pitches reveals is that “reducing friction” often comes at a cost of over-centralizing the market. We need to think more broadly about whether keeping the startup ecosystem a bit more decentralized, even if that may seem “inefficient,” is actually a net positive in terms of trust and security for startups.

Carta, the cap table tool and self-proclaimed “infrastructure” for startup ecosystems, was all over the news recently in startup circles, because of the following:

In short, it appears that sales people for Carta’s secondary liquidity platform (for selling early startup shares to interested later-stage investors) were accessing cap table data, including investor contact info, of startups using Carta and directly pitching investors as to liquidity opportunities – all without (importantly) the knowledge of CEOs or Boards. A clever (in a mercenary sense) revenue-building strategy, but a spectacular breach of trust. No CEO or Board wants to be worrying about potential huge shifts in their cap table because their cap table software is out trying to get their angels/seed investors to sell their shares.

After a lot of back-and-forth, including some peculiarly aggressive accusations by its CEO, Carta eventually decided to exit the secondary market entirely; a smart move in my opinion even if it’s criticized by some as too reactive. 

What I want to write about on this post is that this whole debacle reveals something concerning about Carta’s long-stated aspirations as it relates to the startup ecosystem. What does it really mean when Carta repeatedly states that it wants to become foundational “infrastructure” for startup equity, and that it seeks to reduce “friction” in startup equity markets? Being a great cap table tool – what Carta originally was – has always been an obvious positive for startups, even if Carta has repeatedly been criticized for being overpriced and too complicated and has since started receiving more heated competition from leaner alternatives; particularly Pulley.

But should founders, VCs, and other startup ecosystem players actually want a centralizing tool to maximally unify the ecosystem and reduce so-called “friction,” as Carta has repeatedly pursued, or is there something about the decentralized nature of the startup market that is actually good? Is it possible that some “friction” in how the startup ecosystem functions is desirable and positive for founders and startups?

Analogies to the decentralization philosophy of crypto, and perhaps also open source software, are appropriate here. Crypto gets lambasted for all the energy that is expended in maintaining blockchains, but the regular response is that “inefficiency” is worth the added security of not having any centralized node that market participants need to trust to behave “nicely.” Friction is a price that is sometimes worth paying in high-stakes situations where trust and security are paramount.

You see similar concerns when discussing proprietary v. open source approaches to various forms of software and hardware. Yes, there is some benefit in some contexts to relying on proprietary “infrastructure” – scale economies, data aggregation, etc. – but obviously concerns about monopolistic rent extraction loom large and very often push markets toward decentralized or even open source standards.

I’ve raised my own concerns about conflicts and interest in startup ecosystems, when self-interested players with broad brands pretend to be helping founders but are in fact using their market power to effectively extract rent from the market. For example, I wrote about how YC’s Post-Money SAFE is actually a horrible instrument (economically) for many startups, and many founders don’t get advised about how to make its terms more balanced. YC has made a ton of money from pushing the Post-Money SAFE as a “standard.”

But the selling point of YC’s templates has always been “efficiency” and “reducing friction.” Again, we see a trade-off: trusting a self-interested party (in this case an influential investor) to set so-called “standards” may in some sense reduce “friction,” but the cost of that friction reduction is significantly more dilution to startup founders. Friction reduction, and trusting a centralized party to provide it, is not a free lunch. We need to assess the full costs before determining that it’s actually a good idea.

I’ve advocated for a more open source approach to startup financing templates, where we don’t pretend anything is a “standard” that shouldn’t be negotiated, but still allow for a github-like repository of well-known starting points for negotiation. This allows for some measured benefit of standardization, while maintaining decentralized adversarial players who negotiate and ensure each deal truly makes sense for the context.

I’m also an advocate for open source cap table templates. I think automated cap table tools have over-sold themselves, particularly at the earliest stages, and founders would be wise to understand that Excel is perfectly fine (and free) until perhaps Series A, or at least post-Seed.

I’ve also written about the tendency for startup law firms to flout conflicts of interest with the VC community. They’ll build deep relationships with VCs, while parlaying those relationships into representing the companies those same VCs invest in. The founders are often told that these counsel<>investor ties will “help” them – it will reduce “friction” because the lawyers know the VCs well – but it’s complete nonsense and even contradictory to the entire point behind rules around conflicts of interest in law.

You simply can’t trust lawyers to advise you properly in negotiating with a VC if that same VC regularly sends work to those same lawyers. This is why we designed Optimal to be a company-focused firm, and we regularly turn down VCs who ask to work with us. That has a cost in terms of limiting our revenue opportunities, but not unlike Carta’s decision to exit secondaries, it’s about preserving client trust. It’s a bet that the market needs and wants a player, in our case a law firm, offering trusted advocacy above what more conflicted players can provide.

All of this suggests that friction, though sometimes spoken of exclusively in negative terms, often serves a purpose. Negotiation is friction. Diligence (including of a VC’s reputation) is friction. Competition and independent review (even if redundant) is friction. Having multiple sets of advisors representing different parties instead of everyone mindlessly trusting one conflicted group is friction. Assessed holistically, sometimes friction is worth it when interests are fundamentally misaligned. 

So my advice as a VC lawyer watching how this has all played out with Carta is: the outcome here is good. It’s good that the ecosystem spoke its voice, and Carta acknowledged a fundamental problem with its business model. But let’s not miss the much broader lesson here as it relates to the many other situations in which some influential ecosystem player will promise startups “less friction” in exchange for trusting them perhaps far more than they really deserve.

I like Carta as a cap table tool, even if I think it needs to simplify itself and lower costs. I am, and have been, much more deeply skeptical of Carta as centralized “infrastructure” for the entire startup ecosystem, promising all of these wonderful benefits so long as we trust it with enormous amounts of power and data. This most recent debacle (I think) shows why others should be a bit more skeptical too.