Scaling Strategic Counsel

TL;DR: There is no shortage of entrants into the legal market who pretend that some magical formula, or piece of technology, or amount of money, is the key to “disrupting” law firms with prominent reputations. For the kinds of lawyers who do far more than just push paper, it usually ends up as different versions of the same flawed story.

Background reading:

I’ve spent a lot of time analyzing how the consumers of legal services think and behave. In doing so, I’ve had a fun time watching the evolution of various hypotheses held by legal market entrants (firms, solo lawyers, technology companies), and predicting where they would go. Success in any business (including the legal business) doesn’t require psychic abilities, but if you have good instincts for human behavior and psychology, you can surprise people with how accurately you can predict the future.

“Faster and cheaper” can take you far in many industries. And while “startup law” isn’t entirely an exception to that rule, there are subtle but extremely material factors that make it particularly challenging to build and scale a serious emerging tech law firm.  The below are some personal thoughts on how emerging companies (startups) select their lawyers, the flawed hypotheses that lead many players in the legal market to fail or stall, and principles we’ve held as we’ve patiently grown E/N from a handful of people into a leading emerging tech/vc boutique law brand scaling outward from Texas.

1. Long-term, quality really matters. A lot.

“The bitterness of poor quality remains long after the sweetness of low price is forgotten.” – Benjamin Franklin

When you purchase a family vehicle, or select a surgeon, more likely than not price is not the final determining factor in what you end up buying. But for a lot of people, I would bet price plays a bigger role in purchasing a meal, or a piece of clothing.

Why? Because the stakes, and consequences of a serious error, are much higher for the former. Long-term thinking purchasers of legal counsel understand this extremely well, and it’s the reason why despite there being a glut of lawyers broadly, those in the top quartile, particularly those who serve the C-level among companies, have never done better. “Minimally viable lawyers” are not doing very well.

“Move fast and break things” is an extremely valuable philosophy in a context where mistakes are easily, and unilaterally, fixable; which is why it emerged from software entrepreneurs. In the legal world, where something broken very often cannot be fixed, and something as minute as the absence of a few words, or a single missed step, can completely and permanently alter the outcome, it is a stupid and dangerously reckless way of approaching things.

Efficiency is absolutely important. To say that quality really matters is not at all to say that cost is irrelevant, or that smart clients don’t dislike seeing waste. We love adopting new technology, and the speed at which we (as a boutique) can do it makes us a magnet for legal tech startups. However, a foundational principle of E/N’s sustainable growth has been that we deliberately filter out prospective clients who clearly do not value legal counsel; no matter how promising their business may be.

Just like the economic viability of Tesla, or any high quality brand, requires consumers who are willing to pay what it takes to deliver quality, the viability of any serious law firm requires clients for whom low cost is not their primary principle in assessing legal services. All early-stage startups face challenges with legal budgets, but smart law firms learn to identify when the issues are coming from real budget pressures that can be accommodated v. a personal sentiment that legal services are just overhead spend to be minimized.

I’ve seen many law firms fail by thinking that “we can do it cheaper” is, alone, an effective business development strategy. First, that strategy inevitably attracts the worst, most disloyal, clients; who treat lawyers as fungible commoditized vendors. Second, the smartest clients know that, without trustworthy evidence that quality has not been hit, very low prices signal very low quality, which is too risky for a high-stakes service.

2. For strategic advisory, independence and creative judgment really matter.

There are two levels of legal work that a serious corporate law firm can provide. One is transactional counsel, where the goal is to get it done, correctly. Precision (quality) and efficiency are the primary values for transactional legal work. You definitely want a law firm that can demonstrate that they take precision and efficiency seriously.

The next level of service is a lot rarer in the market, but the smartest clients seek it out: strategic counsel. Strategic counsel isn’t about executing a plan of action with precision.  It’s about creating a plan, and that requires creativity (stepping outside of a standard playbook) and social intelligence (what does this specific client care most about?). What should you do? Why should you do it? What will happen if you do X or Y? How will other players respond?

To use metaphors, merely transactional lawyers help you play checkers, but strategic counsel helps you play chess. And at the highest C-level issues in complex markets, you better believe you are playing chess. For that kind of work, the judgment of the particular lawyer (apart from the firm) you are working with is extremely critical, and it’s why I’ve written before that avoiding “captive” counsel (getting independent judgment) in this context is essential. For startups/emerging companies, very very few advisors are able to integrate deep knowledge of legal issues, market norms, contract comprehension, financial structures, and strategic analysis the way that a top VC lawyer can.

A big area where I’ve seen law firms fail in recruiting is a lack of appreciation for this transactional v. strategic divide. They care so much about credentials and “IQ” skills, which are important for accuracy, that they neglect to hire for the kind of strategic judgment that the smartest clients seek out, and are willing to pay for. Good strategic judgment is as much about instincts, situational awareness, and character as it is about intelligence. Fail to recruit for them, and you’ll get high-precision paper pushers. 

Even within large firms with very prominent brands, you often notice a wide disparity among partners in terms of their ability to attract clients. The driving force behind that disparity is judgment. Clients know most of the lawyers at that firm can execute a task properly, but the number of lawyers who can really advise on core strategic matters (like a term sheet, or a key hire) – and particularly the ones who will do so for a small (but promising) company – is significantly smaller.

3. You cannot assess quality without diligencing reputation.

As I wrote in “Ask the Users,” for the most important people building your team of advisors, service providers and investors, you cannot afford to rely on highly ‘noisy’ signals like social media, PR, public reviews, or even blogs. The level of BS spin that money can buy you on the internet is boundless. You must go directly, and confidentially, to people who’ve worked directly with those people, and get their off-the-record feedback.

There are certain qualitative aspects of legal counsel that are highly visible to a client very quickly in their relationship with a law firm. These are usually things like responsiveness, soundness of advice, efficiency, technology, etc., and they are very important. Delivering on these variables is very complex and hard for a law firm, so hearing good user feedback on them is a good sign.

However, legal services are somewhat unique in that the full truth about their quality can take years to reveal itself to a client. At very early stage, where a lot of documentation is heavily precedent driven and transactions move fast to keep bills down, founders/executives often don’t spend very much time actually reviewing the work product of lawyers in depth. They assume it says what it should, and they often don’t even know what it should say. 

It’s in Series A or M&A diligence, with serious counsel on the other side of the table reviewing the legal history, that the wheat really gets separated from the chaff among VC counsel. And people who’ve played the VC/Emerging Tech game in depth know that there’s a lot of “chaff” even among prominent law firm brands.

You can think of the end-product of a law firm as software code that truly only gets reviewed/run every few years in major milestones. Major “bugs” can sit there for years, compounding enormous legal technical debt, without anyone on the business team being aware. When you diligence counsel, you want to hear about what errors/mistakes were discovered in VC or M&A diligence, which means talking to companies that actually got there. Doing a great job at pumping out option grants or convertible notes is not a reflection of the kind of legal quality that matters long-term; nor, frankly, is having worked for a few years at a prominent law firm brand. People deep in the game have many horror stories about how the B or C-player at a firm with a marquee brand screwed something up badly. 

Conclusion: This sh** is hard. Really hard. Way more complicated, if you want to scale sustainably, than putting together a few half-decent lawyers, having them put on jeans, and buying them MacBooks; which is pretty much the extent of what many boutique firms do.

With respect to serious emerging tech legal services, including strategic counsel, you’re talking about building something at scale that addresses all of the following:

(i) extremely small details can have extremely large and often irreversible consequences that are undiscovered until years later;
(ii) because every client’s needs are widely different, you are squarely in highly customized services, not automatable product, territory;
(iii) your ability to attract (and pay for) highly-educated human talent with very subtle behavioral differences dramatically influences the quality of your highest level service;
(iv) you have to be able to filter out the prospective clients who simply won’t pay the real cost of your service, regardless of their budget or how efficient you are, while being flexible/patient on budgets with (hopefully) good clients in their very early days;
(v) there is a part of your industry that is hell-bent on proving that some magical piece of technology is suddenly going to render you irrelevant; and
(vi) aggressive, influential players are sometimes trying to undermine your ability to provide your clients honest advisory.

Though you will endlessly hear opinions to the contrary, there simply is no “move fast and break things,” “mvp and iterate,” “just throw lots of money at it” formula that gets the job done in complex legal services; not if you take quality seriously. And this is why “disrupting” the status quo has proven so difficult despite the fact that it’s a large industry totally exposed to people whose entire MO is to disrupt things.

And yet here we are, patiently putting together the intricate pieces of this unique puzzle, and continuing to grow. Lawyers have popped up claiming to be cheaper, and yet we’ve kept growing. Software tools have popped up pretending that the primary challenge of our industry is a technological one (it’s not), and yet we’ve kept growing. Influential market players have tried to convince our clients to switch to “captive” firms, and yet we’ve kept growing. This is not some “scale fast at all costs” game we’re playing; not when the cost would be exposing good, hard-working people to extremely costly errors.

While we’ve definitely broken more than a few rules of conventional wisdom for how law firms are usually run, we are still here to do our job, correctly, honestly, and efficiently; and to win the trust and loyalty of people who truly value what we are built to deliver.

And for the many people out there who might find all of this a bit passé, no worries. There are plenty of alternatives out there to suit you.

Ask the Users

TL;DR: Blogs, social media, and public endorsements are all noisy, and often false, signals about a person’s real reputation in the market. The only way to get the truth is to “ask the users,” and in a way that allows them to speak the truth without negative repercussions.

I’m going to keep this post as simple as possible, because the message, though extremely important and often lost on people, is quite simple.

Should you join a particular accelerator?

Ask the users – the companies that have already gone through it.

Should you accept money from a particular fund or investor?

Ask the users – the portfolio companies that have already taken money from them and gone through ups and downs.

Should you work with a particular mentor / advisor?

Ask the users – the companies they’ve already advised.

Should you use a particular law firm, accountant, or other service provider?

Ask the users – their existing clients, particularly the ones who’ve gone through a major transaction.

One of the most dramatic, impactful things that the internet (and services like LinkedIn, AngelList, FB, Twitter) has done is made it 10x easier to connect with other people to get direct, unfiltered, off the record feedback on their experiences in working with others. It has made BS a whole lot harder, and ultimately improved behavior across the board. But that brings up some important points worth keeping in mind as you “ask the users”:

A. As much as the web has made finding direct feedback easier, it’s also magnified the opportunities for untruthful marketing.

Blogging and social media are great ways to get a feel for a person’s persona – or at a minimum the persona they want to display publicly, which itself is a valuable, albeit noisy, signal. However, never underestimate the capacity for sophisticated players to whitewash their online reputations. What you see on a blog, on Medium, or on Twitter is marketing, and it’s only with due diligence that you verify it’s accuracy.

And yes, that speaks for this blog and my own social media presence as well.

B. Do not assume that a public-facing endorsement is reflective of that person’s true opinion.

Reality check: people use public endorsements as currency. A VC will make their investment, or assistance on some project, contingent on the expectation that founders say a few glowing things about them on Twitter. A lawyer will agree to discount a fee if they can get a great LinkedIn recommendation. An accelerator will make an intro if the founders will write a great Medium post.

Public endorsements, though valuable as a signal, are fraught with ulterior motives. In short, they can be, and often are, bought.  I know plenty of people who, for some quid-pro-quo arrangement, have given public endorsements for market players whom they would NEVER recommend privately. Do not take a favorable public comment as reason to avoid doing private, off the record diligence.

C. Ignore the opinions of sycophants.

Every ecosystem is full of people who will sing the praises of anyone influential simply because that influential person could get them business. It may be too far to call some of them spineless, but ultimately they lack the personal brand independence to speak accurately about other peoples’ behavior. No one is perfect, and if someone’s review of a particular player feels totally over-polished, it’s probably because they’re not telling you the truth.

You want feedback from serious, honest people who are willing to speak their mind (but see below).  Not a bunch of random cheerleaders.

D. Talk privately, and don’t reveal whom you’ve spoken to. 

No one who has an active, ongoing relationship with someone wants to damage that relationship, even if they’re not entirely happy with it. Doing so is irrational. If I’m in an accelerator, I still depend on that accelerator’s support, so don’t expect me to go on the record for badmouthing them. The same goes if I’m in a particular VC’s portfolio, or working with a particular law or accounting firm.

This is why it’s extremely important to do “blind” diligence; meaning if you are diligencing X by asking Y, you absolutely do not want X knowing that you asked Y. If a VC tells you to ask a specific company about their experience in working with them, then they know exactly whom to punish if you end up walking. If you go through their portfolio and personally decide whom to ask, you remove that ability, and therefore dramatically increase the likelihood that you’ll get honest answers.

And it should go without saying: phone calls or in-person meetings. Don’t expect honesty in a forward-able e-mail.

E. Focus on patterns, not a single review.

Even the best restaurants have the occasional negative review because they either were having a bad day, they simply weren’t a good fit for the particular patron, or – and let’s be honest here – sometimes the user is a pain in the ass. The customer is always right? Nope, sometimes the customer is a moron.

Don’t assume that you’ve got the full picture from simply asking one person. Ask a few, and the line drawn from the dots will matter much more than the individual data points.

F. If you can’t diligence, you need a right of exit. 

The stakes are highest for relationships that you really can’t extricate yourself from. A serious investor is the clearest example. Never take money from a VC without performing diligence.

However, for other service providers – take an advisor/mentor for example – there are other mechanisms to de-risk things. If they’re getting equity (which they often are), a “cliff” on their vesting schedule is the best one; typically 3 or 6 months. That should be enough time to understand the reality of working with them, and make corrections if it’s a terrible experience. Solid contracts help here, with clear, painless rights of termination.

However, a word of caution – all the contracts and lawyers in the world will not protect you from the enormous cost and time suck of working with sociopaths. Even if you don’t have the time or ability to diligence their “users,” you should at a bare minimum vet them personally with interviews, questions, and other ways to get a general feel for their personality and values. If you have good instincts for judging people – and if you’re a CEO I hope you do – you will be able to filter out most assholes.

Lies About Startup Legal Fees

It usually takes experience in the market for business people to truly understand the realities of hiring and working with lawyers. I can’t tell you how many times I run into first-time founders who’ve been fed absolute nonsense from ‘advisors’ ‘mentors’ or similarly named people about their ‘secrets’ for managing legal spend. The truth is that unless you’ve taken a company from seed to Series A, Series B, Series C, to an exit in which a serious party on the other side actually diligenced the legal history your ‘secrets’ put together, your theories about lawyers are hot air.

Failed companies never pay the price for poorly managed legal; unless the failure was the result of the legal problems, which does happen. Successful companies, however, pay deeply for legal mistakes. It’s  just a question of timing. There are definitely steps you can take to prevent legal spend from getting out of control, but it requires separating reality from delusion. The below is my attempt at doing that.

1. Software automation (or free templates) will not replace your lawyers, or dramatically cut legal spend.

See: Luddites v. Tech Utopians. New market entrants in technology have a tendency to come out with guns blazing, promising their ability to cut out enormous amounts of waste as reason to adopt them. Sometimes they’re telling the truth. Other times it’s well-calculated hyperbole.

Virtually every serious automation tool that has emerged with “cut huge amounts of legal spend” as its primary selling point has evolved into a tool for lawyers. Why? Because, contrary to some popular opinion (and marketing talk), good lawyers really aren’t charging hundreds of dollars an hour to just fill in numbers or check off boxes. Good tools are very helpful for making lawyers/firms more efficient, and you want lawyers who use those tools, but a piece of software isn’t going to replace your lawyers any more than a piece of software will replace your software developers.

Yes, there is form-filling and box-checking ripe for automation, but it’s not nearly as large of a percentage of legal spend as some let on; and the low-hanging fruit is already eaten by software like Clerky or Ironclad.

2. Handling it yourself won’t save you legal fees.

I could write an entire book listing all the “hold my beer” moments I’ve encountered with someone on a management team thinking that they were wisely saving legal fees by taking an issue into their own hands, and it then predictably blowing up in their faces.  Part of it boils down to simple sloppiness. Other times it’s a clear case of someone not knowing what they don’t know.

There’s a related dynamic here to the first point about technology companies overstating their ability to cut legal spend. Anyone selling anything (a product, a service, themselves) has to justify it somehow, and “those damn lawyers” are a great bullseye. A COO / CFO wants to justify his salary, and an easy way to do that is by claiming to ‘save’ you legal fees via DIY legal work. You’re not saving anything. You’re magnifying your fees (cleanup is $$$), but deferring them temporarily.

3. Quickly hiring an “in house” lawyer won’t save you a dime.

CEO: “We’re thinking about hiring an in-house lawyer to save some legal fees.”
Me: “Great. What’s his/her starting salary?”
CEO: “$95K”
Me: “Going to be complete shit, and will cost you 10x more long-term.”
CEO: “What? That’s more than some of our execs make.”
Me: “Senior lawyers worth having won’t even talk to us if we’re recruiting with less than $200K. And our lawyers have fantastic work-life balance. You’re recruiting in the same legal talent market I’m in. You really think you found some magic button that cuts the market rate in half?”

Look, I get it. Good lawyers are expensive. Really good lawyers are even more expensive. Fact: Talent is expensive. Everywhere. Make it incur three years of opportunity costs (law school) and a small mortgage (about $200-225k for law school, all in) before it can hit the market, and it gets a whole lot more expensive. 

Last time I checked a solid software developer will cost you six figures in salary; ignoring equity. And ‘coding’ mistakes are 10x more fixable, and potentially less costly, than legal mistakes. It is absolutely the case that a small portion of the tech community arrogantly believes that engineering talent is the only talent really worth paying for. Good luck with that.

I’m not trying to defend what lawyers make here (I don’t need to), but what I am saying is hiring lawyers has the exact same talent market dynamics of hiring any other kind of professional.  So you say you’ve found a lawyer willing to work for a lot less. Congratulations, you caught lightning in a bottle; found a rupture in the space-time continuum.

Or you just found a lawyer completely lacking in the experience/skillset needed to actually replace the work outside counsel (including a set of specialists) is doing for you. There is definitely a time to hire a general counsel, but for it to actually make sense mathematically and not result in extremely expensive mistakes, it’s usually much later in the company’s history than you think. Past “startup” territory.

4. Flat/fixed fees don’t “align” incentives with your lawyers. They lead to rushed work and poorly negotiated deals. 

Take two law firms that charge you the exact same amount to close a deal: one firm bills by the time they actually worked, the other on a flat fee. The flat fee firm is rewarded for (i) not negotiating deal terms, (ii) delegating to inexperienced staff who are “cheaper” (to them), and (iii) working off of rigid rules/checklists that can be automated, instead of flexibly assessing the context. In other words, flat fees incentivize lawyers to rush their work, which is dangerous for high-stakes legal issues where the “client” (often at early-stage an inexperienced entrepreneur) doesn’t know how to fully assess quality.

For more on this, See: Startup Law Pricing: Fixed v. Hourly. Flat fees don’t “align” incentives with your lawyers. They reverse them, often making them more dangerous. For low-stakes, highly standardized work (like formations), fixed fees can be generally benign. For high-stakes and high-complexity work where the “client” doesn’t have the experience to assess quality, don’t reward lawyers for cutting corners.

5. A few real truths about legal spend. 

A. Compensation and specialization drive talent quality. Quality prevents errors, and therefore controls fees long-term.

Fundamentally, two things drive lawyer recruitment (I know, because I recruit for E/N): compensation and quality of life. Very large firms generally have terrible quality of life for their lawyers, for a number of reasons too complex to discuss here. But that’s why large firms have to pay their lawyers the most.

In-house positions and boutique firms are recruiting pipelines for what I call “BigLaw refugees”; talented lawyers looking to still get paid well, but take a moderate pay cut (sometimes) in exchange for the ability to keep their marriages in tact, and their kids out of therapy. But as discussed above, to get the full-time attention of those lawyers, even with great work-life balance, you still have to pony up in amounts virtually no true startup can afford. That’s why outside counsel (‘fractional’ lawyering) is valuable.

And working with lawyers who specialize in emerging tech/VC work will ensure you’re paying for talent experienced in the kind of legal work you actually need. See: Startups Need Specialist Lawyers.

B. Law firm “overhead” increases legal spend above base lawyer compensation, but enables scalability and quality. 

On top of the money paying a particular lawyer’s salary, you have the ‘institutional overhead’ of the firm that employs the lawyer. For a deeper discussion of law firm overhead, see: Startups Scale. Solo Lawyers Don’t. 

Companies who think only large firms with the highest rates have the best lawyers (compensation) are ignoring the interplay of overhead and compensation. If you cut overhead intelligently, you can still pay lawyers very well, but at lower rates to clients. The issue is how much overhead to cut out.

Institutional overhead, properly structured and right-sized, is not wasted money any more than the ‘overhead’ (on top of salaries) of any company is wasteful. In law, it enables recruitment, technology, training, staff, and other infrastructure that turns a set of lawyers into an integrated legal services provider, with bandwidth that can be optimized to keep work moving.

Think about what type of company you want to build long-term, or at least expect to be for the next 5 years, and ensure you engage a firm with the right institutional infrastructure (overhead) to serve that company. Very very large firms are designed for unicorns, and require the most ‘infrastructure,’ and therefore overhead.  In fact, the majority of what you pay large firms is paying for infrastructure. Are you planning to be a unicorn?

We are quite honest in saying that, as a high-end boutique firm, our target client is looking to (realistically) exit at under $300MM. We don’t work for unicorns; nor do we try to.  But we also don’t work for small businesses hoping to sell for a few million.

We pay our lawyers compensation that is highly competitive with large firms, which (again, a talent market) ensures quality. Our lawyers also bill about 25% fewer hours per year than BigLaw lawyers, which improves their quality of life (helps recruiting/retention).  But because we have dramatically lower institutional overhead, our rates are lower; although nowhere near the lowest.

In my experience, the size of your Series A round is usually a pretty good indication of the type of company (exit size) you’re trying to build; companies truly going for unicorn status raise much larger rounds. Pre-Series A, the majority of serious tech companies require some accommodation to manage their legal budget; no matter how efficient their lawyers are.

If Post-Series A, your company’s legal bills still seem completely unmanageable, that’s often a good indication that the law firm you hired is too big for what you’re building (non-unicorn-track using a high-infrastructure unicorn law firm); assuming your expectations on what the bill should be simply aren’t unhinged. Remember, small firms can have very high quality lawyers, because they aren’t paying them less. They just have a leaner infrastructure designed for non-billion-dollar clients.

C. Flexible pricing / payment from a quality firm is 1,000 times better than “going cheap.” But be realistic about the budget. 

If you get anything from this post, it is this: good, scalable legal counsel costs real money, like any talent. There is no magical software, recruiting strategy, or template on google that will get around that. Anyone who thinks they are cheating this rule, and have somehow found bargain-basement counsel that works, is just not yet hearing the ticking of the time bomb they’ve turned on in their company.

The absolute best strategy for engaging serious legal counsel, but not going bankrupt on legal fees is to ensure that:

  • you’re working with lawyers who have the right specialization for what you need;
  • at the right quality level, and with right-sized overhead for the scalability you need; and
  • who will flexibly work with you on budget/payment at the very early stages.

Law firms who specialize in emerging tech work are not new to the challenges of very early-stage startups trying to manage a legal budget; at all. It is deeply engrained to each lawyer’s expectations. And there are a lot of levers that those firms can and will pull for clients they want to work with: discounted fees, deferred fees, equity arrangements, etc.

The key part is “clients they want to work with.” They are selective, because they have to be.  Serious law firms are not in the game to work on mickey mouse fixed-fee or discounted projects to eternity; nor can they afford to be. They do that to scale down for valuable prospects with the right potential lifetime value (LTV) as clients, but who need help when the budget is slim. That’s why any early-stage, limited budget company that approaches a serious law firm should be ready to “pitch” their company to the firm.

For high potential companies, great tech/VC lawyers will be flexible on budget and payment as long as the founders are reasonable in their expectations. And the best way to be reasonable is to follow the points in this post. Accept that you need good legal talent, badly. Accept that it costs real money, and that you likely can’t afford the full cost up-front, and that’s normal.  If you’re as good as you hope you are, you will find a way to navigate that reality.