Integrated Startup Law — Specialists Matter

Without getting bogged down on details, you can largely categorize physicians as general practitioners and specialists. Generalists are the every-day doctors that provide primary care for more routine matters, and also (hopefully) coordinate care with specialists (cardiologists, neurologists, etc.) when appropriate. Unfortunately, the U.S. healthcare system does a terrible job on that second part, but this is a blog about startup law, not healthcare. End of digression.

The practice of transactional law, including startup law, can also be categorized in this way.  A “corporate lawyer” serves the role of the general practitioner. Her job is to handle the more common matters that a client is likely to encounter, and to coordinate with specialists (tax, labor, IP, etc.) when their input is needed.

Biology is Integrated

Anyone who’s studied health policy knows that, by far, the most effective and efficient healthcare delivery models in our country — Kaiser Permanente, Mayo Clinic, etc. — are what many call “integrated.” Specialists and generalists work under the same system, and share information with one another in as frictionless of a manner as possible. The reason for this is that the human body itself is an integrated system. The heart doesn’t operate in complete isolation from the brain any more than my macbook’s hard drive operates in complete isolation from the CPU.  So it makes little sense that medical practitioners who specialize in different systems of the body work alone, as if the knowledge of other specialists is irrelevant to their own work.

Startup Law is Integrated

What I try to ensure that our clients appreciate is that the law itself, including the law that affects startups on a daily basis, is also integrated.  Even at the most standardized of startup legal events — formation — there are at least half a dozen specialties of law that play a role in the steps a client needs to take.  Securities Law, Labor Law, Intellectual Property Law, Commercial Litigation, State Corporate Governance Law, Tax Law, etc.

A view commonly heard about early-stage startup law is that it’s all become so “standardized” that large, sophisticated institutions with specialists (not just generalists) are no longer needed to properly serve clients; the end-result being a retreat to a “cottage industry” mentality where small practices of generalists have set up shops pitching themselves as delivering the same service, but without all that unnecessary “overhead.”  Some have gone so far as to call this trend a “disruption” of law practice.

My response to this perspective is three-fold:

1. “Standardized” and “Simple” are not the same thing. Not even close.

Production of the iPhone is standardized; otherwise no one would be able to afford it. But that doesn’t mean the design and building of the iPhone is “simple” in a sense that it could be produced by a fragmented cottage industry lacking the resources of Apple.  In the same sense, the set of twenty or so documents that we produce for our startup formations has become standardized to the point that we can produce it quickly at scale, but the expertise of at least half a dozen specialties went in to producing it, and is required to constantly update it and ensure it fits the current state of the law.  A set of lone generalists, even brilliant ones, simply wouldn’t cut it.

2. The exact same process, delivered from a smaller office, while wearing denim, does not a disrupter make.

Disruption of an established industry comes from delivering what consumers want, but in a radically different, often cheaper way.  Productizing the expertise of highly educated and specialized individuals and delivering it at scale so that far more people can afford it: that is disruptive – and it’s happening in startup law.  Cutting off the relevant expertise of a large portion of the profession, moving into a smaller office space, and continuing to deliver the product in the exact same way: t’is not disruptive.

Because smaller legal practices often do have salary structures that lower their labor costs, they do tend to have lower hourly rates.  But many (that I’ve encountered) use this lower labor cost as an excuse to avoid adopting the kinds of technology and practices that actually make the delivery of startup law efficient.  In other words, “our hourly rates are lower, so it’s OK if we take longer to do something.”  People operating in Big StartupLaw, particularly techies like myself, are often floored to see how backward some (not all) smaller practices are. This is not a space for “cottage” practitioners, though not all smaller practices fit that definition.

3. Specialists will need to be consulted.

Forming your startup or raising a simple seed financing might be thought of as the legal equivalent of getting a cold (simple service is fine), but actions taken at the not-that-much-later stages of the startup, like drafting executive employment agreements, developing and protecting intellectual property, issuing securities, negotiating commercial contracts to be enforced in multiple jurisdictions; these can touch on legal nuances that are a whole lot more like brain or heart surgery. Leaving everything in the hands of a generalist can end up ugly.  We’ve seen this happen many times.

The high growth nature of tech startups means they can go from playing legal tee-ball to the major leagues very quickly, unlike most kinds of businesses that utilize small firms.  Legal representation that can scale with the startup at all of its stages, rather than max out once the startup becomes successful, is extremely valuable; particularly because the costs of switching law firms are not insignificant. The key is to find an integrated firm that packages and prices its services appropriately for each stage of a startup.

Fragmentation v. Integration

Many smaller practices are well aware of these limitations in their model and have developed informal networks of specialists from other firms to call upon in situations when their expertise is needed.  I’ve touched on this topic here.  While this is definitely a good thing, thus far I’ve been unimpressed with the mechanisms (i.e. none) that smaller practices have put in place for actually drawing upon their “network” in an effective and efficient manner.

Having to formally engage a new law firm (including running a conflicts-check) to ask a question that someone under an integrated system could get answered by walking down the hall doesn’t exactly smell like progress to me.  Even if it works for lengthy, project-based engagements, the kind of quick, 15-minute consults that are commonplace (and necessary) in an integrated firm will inevitably go under-utilized in a system with that much friction.

Some “multi-specialty” firms have done a little better and brought in-house the handful of types of specialists that are most likely to be needed by a startup: employment, tax, and IP seeming to be the most common.  But that’s a tough model to sustain because those specialists almost invariably need to also work for large non-startup clients (the kinds that don’t work with small firms) to keep their practice profitable.

Of course, as in other industries, at some point the right platform for allowing a fragmented system of specialists to coordinate ad-hoc may emerge in a way that can match the quality and breadth of the integrated system. But for now, this “PC” of startup law is nowhere to be found.  For matters beyond the absolute most basic, Apple-like integration wins.  Note, however, that a smaller footprint can actually be the optimal model for attorneys/firms with enough brand recognition (gravity) to dominate a particular niche specialty (not generalist) of the market.

Conclusion: Process efficiency and technology innovation will disrupt legal practice. A “cottage mentality” will not.

Progress and innovation in the startup law space will not come from doing things the same old way, while wearing jeans in a less fancy office space.  It will come from sophisticated parties that, instead of retreating from the web of specialties that make up the field, find smart ways to affordably package and productize their knowledge.  This process is well underway, and it’s incredibly exciting to operate in.

Form Your Austin Startup Yourself Before Hiring a Cheap Lawyer

Note to reader: Please share this with as many low budget startup founders (particularly in Texas) as you know. Friends don’t let friends waste money on crappy lawyers.

So you’re starting a company with virtually no budget for legal fees, and you just found a guy in Austin who’s willing to help you out on the cheap. He even bills $175/hr and seems to come well-recommended by other entrepreneurs. Awesome, right? For me it is.

It’s difficult to overstate just how often clients end up paying our firm more to close a transaction, sometimes substantially more (think 5-6 figures), because we have to clean up a mess created by some cheap local lawyer with “startup friendly” (read: questionably low) rates.  Garbage sold at a low price is just expensive garbage.  There’s one solo practitioner in particular who’s done work for two people I know, separate companies, and screwed up big time on both of them (2/2).   One ended up closing a VC round at 2-3x the usual fees in order to clean up the disaster he created. Cheap is awesome until real investors hire real lawyers to actually read the documents your cheap lawyer drafted… or failed to draft.

I’ve previously articulated my views about going alone on startup legal issues, including a discussion on the growing number of DIY tools available online.  There are so many multi-specialty legal issues that come into play in forming, growing, and financing a company, that I highly advise against trying to do things yourself, at least if you expect to raise professional venture capital and scale your business. The stakes are simply too high.

But, the reality is that no matter what every lawyer with a blog says, founders will keep trying to form their companies on their own.  Given this reality, here’s my suggestion to all of Austin’s startup founders with zero funds budgeted for legal fees (and who can’t find a decent attorney who will be flexible):  meet Docracy, read this post, and follow everything very carefully.

Lawyerless > Crappy Lawyer

The beauty of quality DIY online resources is that, while they will never provide the level of service that an experienced, quality attorney will provide, they sure as hell are better than relying on a crappy one.  With the right contracts available for free online (via Docracy), the right guidance (via blogs, articles, etc.), and the patience to seriously read the instructions, you can stand a much better chance of not screwing your company up by doing things yourself versus hiring an incompetent attorney, trusting him to do things correctly, and then finding out two years later that he didn’t.

So here’s my free guide for using the power of the internet to form your own Delaware C-Corp based in Texas. If you are forming an LLC instead of a C-Corp, then for the love of all things good and holy, please get a competent lawyer.  And again, let me reiterate: I do not think you should try to form your startup on your own. My desire here is to simply provide a helmet and a flashlight for those who are going to do it anyway, so that if they are ever able to afford a real attorney and raise serious funding, their legal history won’t be a complete nightmare.  You will screw some things up, but hopefully the clean-up costs will be much smaller than those caused by Austin’s crappiest lawyers.

DIY Startup Formation – Powered by Docracy, Orrick, and “the Internets”

Background Reading:

Requisite Formation Docs:

Steps (Order is important)

  1. Read all of the Background Reading – very very carefully.
  2. Figure out your Founder Common Stock distribution and Vesting details
  3. Execute and File the Charter in Delaware
  4. Execute the Action by Incorporator
  5. Execute the Board Consent (Make sure you designate at least a CEO and Secretary)
  6. Execute the Common Stock Purchase Agreements for each Founder, including all exhibits.
  7. File your 83(b) Election immediately
  8. Fill out Common Stock Certificates
  9. Execute the Stockholder Consent
  10. Have the Secretary execute the Bylaws
  11. Did you file your 83(b) election yet? (30 days within Stock Issuance, or your toast)
  12. Apply for an EIN at the IRS Website
  13. Have officers and directors execute Indemnification Agreements
  14. Have all founders execute a Confidential Information and Inventions Assignment Agreement
  15. Register as a Foreign Entity in Texas.
  16. Keep digital copies of everything in a safe place.

Useful Forms to Possibly Use Later:

The above does not cover granting options to employees via a formal option plan, because, frankly, by the time you are granting equity to non-founders you’re insane for not having hired a lawyer – and the legal issues around options are complicated – real complicated.

Disclaimer: As I said before, you will screw some things up. And yes, trying this yourself is silly and irrational – much like a lot of things entrepreneurs tend to do.  The above steps and documents might not even be the right ones for your startup’s context.  I did not draft the above-referenced documents, nor do I vouch for their legal enforceability. You absolutely should hire a lawyer before trying to form your startup. But, putting all that side, if you read carefully and follow the above instructions, you will be probably be on better legal footing than 99% of the startups formed by terrible lawyers.

Should I form my Austin startup in Texas or Delaware?

Note: The DE-related info in this post is really applicable to startups based in any state, but I’m speaking mostly to Texas entrepreneurs, particularly in Austin, in writing this.  Because of the depth of startup activity in California, which might translate to more sophisticated case and statutory law, forming a non-DE startup there might make more sense than it would in Texas.

The default incorporation state in forming a company is always the state in which the company operates, but there are several reasons why an Austin/Texas startup might consider DE instead:

  • Well-Established, Sophisticated Statutory and Case Law – Because DE is the legal home of, by far, the largest number of large corporations in the country, you’ll find the least amount of ambiguity in DE as far as corporate governance practices, contractual interpretation, etc. are concerned.  And DE Chancery judges are by far the most knowledgeable in complex business matters of any judges in the country.  Virtually every corporate lawyer in the country who operates a serious practice will be familiar with DE law, so if you call him/her up with a random question about whether a certain transaction is kosher, or how a particular provision would be enforced in court, you’re 10x more likely to get a quick answer if you’re a DE corporation.  For a Texas entity, the answer will often be “I’m not sure,” which leads to “Let me research that for you,” and that research won’t be pro-bono.
  • Sophisticated Investors will expect Delaware – Because of the above, institutional venture capital firms that manage large funds will (very) often refuse to invest in a Texas startup that isn’t a Delaware corporation.  Angel investors are more likely to be OK with Texas, but we’ve encountered a fair amount of professional angels who either insist on DE before making their investments, or at least expect a conversion to a DE entity before the Company’s first venture capital equity round.
  • Protective of Officers and Directors – Delaware courts have a history of deferring to the business judgment of the officers and directors of a Company, meaning that without evidence of gross self-dealing or negligence, they’re unlikely to use hindsight to second-guess business decisions. This makes finding reputable executives and directors easier, for obvious reasons.
  • Response Time – Ever needed to close that bridge financing in the next 2 hours in order to make payroll? I’ve seen it plenty of times, but surely that would never be your company. Ever. Well, just in case, DE has an amazingly well-greased system for filing legal documents.  For extra fees, you can get guaranteed 24-hour, 2-hour, and even 1-hour response times. Suriname should really consult with the Delaware Secretary of State to up its game.
  • Converting Later is More Expensive – When you’re starting out fresh, there are no contracts to review, consents to get signed, etc. You just form the Company where you want to form it. But as time progresses, and you get shareholders, sign contracts, hire employees, etc., the amount of diligence involved in ensuring that you can convert to a DE entity grows exponentially. Pay now, or pay more later.

The Downsides to DE:

  • Fees (Cost): This is really the only reason why a Texas startup that intends to eventually raise professional venture capital will consider not incorporating in DE.  By forming a DE entity that operates in Texas, you’ll have to file a form to qualify to do business in Texas as a “foreign” (non-Texas) entity. This costs about $750. You’ll also need to maintain a “registered agent” in DE, which will run you about $125 a year. Finally, you’ll have to pay franchise taxes in both DE and TX, although the added cost until your startup becomes profitable is likely to only be a few hundred dollars a year.

So the decision to incorporate in TX or DE really boils down to two questions:

Do you ever intend to raise professional venture capital?

If not, then unless you just find Delaware’s sophisticated business-friendly environment really appealing, you’re probably well-served by sticking with a Texas entity.  A lot, if not most, startups will fall into this category. Save your money and use it to build a great product.

If you do intend to raise professional venture capital, are you willing to incur the additional cost of forming a DE entity?

At formation, the up-front cost differential between a DE v. a Texas entity is likely to be about $1,000, with a few hundred extra a year for registered agent services and franchise taxes.  As time progresses, the cost of converting to DE will increase in terms of legal diligence and logistics as you execute contracts, pick up shareholders, etc. While numbers obviously vary, you can probably expect about $5K-10K in fees in converting your TX entity to DE pre-Series A.

Most of our clients bite the bullet and pay the extra ~$1K to form in DE from the beginning. That’s because (1) we don’t really serve startups that don’t intend to raise professional capital, because they don’t need us, and (2) it sends a signal from the beginning that the Company intends to operate in the big leagues. Still, a handful take the approach that 5-10x in fees is fine down the road if, at least at that point, they’ve found investors or a good revenue stream to help pay the costs.  I generally say that, if you’re really that worried about losing $1,000 in a startup that you seriously think will pursue venture capital, perhaps you should reconsider entrepreneurship altogether.  But it’s ultimately a personal judgment call.

When it’s time for your startup lawyer to shut up.

Hypothetical scenario at doctor’s office:

Me: Doc, I’m here for my annual kidney checkup. (note to reader: I donated a kidney)

Doc: Sure, Jose, I’ll take care of that for you. But while you’re here, let’s cover a few other things just to be thorough. How have you been feeling emotionally? Any signs of depression? And what about your sleep habits? Getting 8 hours a day? Your back looks a little arched. We should check for a spinal problem.

Me: I came here for a kidney checkup.

Doc: Your hair seems to be thinning out prematurely. That could be a sign of a hormone imbalance. Your skin also seems a bit pale. Are you getting enough sun? We’ll check you for a Vitamin D deficiency. And how about your sex life?

Me: Please shut up.

Overlawyered.

The billable hour is to startup law what fee-for-service is for most of healthcare. In some contexts it’s necessary, but it often creates incentives for overtreatment; or in the case of law, overlawyering.  There are lawyers who properly see early-stage transactional law through the eyes of their clients: a mechanism to get a deal done, while ensuring that the contract drafting, negotiation and diligence performed are appropriate for the context. And then there are lawyers who, notwithstanding the needs of their clients, try to achieve some kind of legal nirvana on everyone else’s time and dime.

You want to spend hours ruminating on arbitration provisions, or ensuring that the registration rights language in your docs is air tight? Awesome. Go work for Wachtell and get the hell out of early-stage work. This here’s startup law, son, and this deal needs to close.

Perfection v. Materiality

Now, this definitely doesn’t mean that closing the deal is all that matters, and that legal counsel’s role is purely mechanical.  Experienced entrepreneurs understand the transactional insurance mechanism that good lawyering provides.  The point here is that a high quality startup lawyer isn’t the one who drafts perfect contracts, understands every nuance of securities law, and can spot every minute issue while diligencing the deal.  The best startup lawyers build a deep understanding of what’s material to their clients and their business, and aren’t afraid to close the deal knowing that there may be issues in the docs that would make a law review editor cringe. Good enough? Close the deal. These people have a business to run.

An ounce of prevention.

Business Judgment and Experience Matter

This is also not an argument for going with the cheapest lawyer you can find. Remember, the hourly rate is only half the equation. If anything, I’ve found that boutiques (lower hourly rates) are more likely to run the clock in the name of (air quotes) “higher quality”, knowing they can get away with it and that it drives their BigLaw counterparts nuts. BigLaw attorneys (higher rates), without thought-out processes in place, are incentivized to do the opposite: cut corners and close the deal sometimes too quickly.  This is a topic for a later post.

It is, however, an argument for caring very strongly about the business judgment of your attorney, and steering clear of those whose sense of materiality seems wildly disconnected from your own.  You won’t always see eye-to-eye, and that’s a good thing.  Having been to the rodeo many times before, a good lawyer can see risks that you’d miss.  But if you’re paying attention, you’ll notice fairly quickly when mountains are being made of molehills.

A focus on early-stage work is also crucial.  A lawyer with a history of billion-dollar deals or public company work will likely waste everyone’s time far more than a true early-stage lawyer who understands what’s worth negotiating, what’s standard, and when it’s time to shut up and close the deal.

Set Deadlines

This should go without saying: always set an expected closing date.  It doesn’t need to be insanely aggressive, but if your lawyer isn’t capping her fees, at least cap her time. If it needs to be extended, that’s fine, but a sense of urgency can go a long way toward focusing everyone’s eyes on the material.

Read the redlines; Require explanations

Don’t just let your lawyers go through rounds of redlines without business guidance. After the first round or two, get on the phone and start asking questions about comments that are being made. How is this material? What is the likelihood that this is going to actually become a problem? If it becomes a problem, how much would it cost? Is the language clear enough to prevent litigation if there’s a misunderstanding? You’ll pick up very quickly on whether (a) real business needs are driving these comments, or (b) your attorney’s aesthetic sensibilities are.  If the latter, it’s time for him to shut up.

Startup Law is not for law review editors with OCD. It’s for closers. Anyone who thinks otherwise is likely overshooting the needs of early-stage entrepreneurs/investors, and wasting a lot of time and money in the process.

What’s my startup’s stock worth?

Stepping back a bit from current events and meta issues, let’s talk about something more mundane, but nevertheless frequently asked by startup founders. What’s my stock worth, and why should I care?

Categories: I’d say there are three different types of “worth” that could be discussed here:

(1) worth to you,

(2) worth to others (what they would pay), and

(3) fair market value (FMV).

From an economic perspective, (1) and (2) are the most important.  But from a legal perspective, (3) is the one you should care the most about. Think of FMV as something related to, but conceptually distinct from, what others think the stock is worth. And to be as absolutely straight-forward and jargon-free as possible as to why you should care about it, one word: taxes.

Why should I care?

A. Taxable Gain

First, virtually any time that someone gets stock with a fair market value above what they paid, that’s taxable gain. Naturally, whenever possible, you want to ensure that when you issue someone stock or options, they aren’t also being handed a tax bill with it. Unfortunately, the IRS doesn’t let you pay your taxes with options. Equity in your hand + cash out of your wallet = bad.

B. Regulatory Compliance

Second, with the understanding that promoting equity incentives can be valuable to companies and the economy as a whole, the IRS has provided some safe harbors (of sorts) through which you can issue options to employees while being able to defer taxes down the road, preferably around the time of a liquidity event (cash in your hand to pay that tax). Your attorney can discuss details with you in more detail, but the most important one for purposes of this discussion is: the exercise price of the option needs to be at fair market value.

C. Key Relationship between (1) and (3)

Notice the key relationship between (1) the value that you place on your stock and (3) fair market value. To the extent FMV is below what you and your employees view (subjectively) as the value of your startup’s stock, you’re able to give something that, at least to you and them, is worth more than what needs to be paid to avoid taxable gains. If FMV for tax purposes is $0.50 per share, but to me the stock is worth $2.00, I can pay $0.50 per share, get $1.50 worth of (subjective) gain, and not pay tax.

Nutshell: a low FMV relative to subjective value is a good thing.

So what’s the fair market value of my startup’s stock?

It depends.

Never Sell Common Stock in an Outside Financing

The number one determinant of FMV is always (2) in the above list: what people are willing to pay for it. If/when the IRS chooses to look back at the FMVs you applied to your stock, that will be the first thing they look for. This is precisely why any competent startup lawyer will tell you that, while Common Stock is good for founders and equity incentives for services, you should almost never sell Common Stock in a financing. This will likely “taint” the FMV of your Common Stock, and effectively force you to set a significantly higher FMV for your stock options than you otherwise would have to. For that reason, it’s almost always recommended to do a financing either through preferred stock or convertible notes that will eventually convert into preferred stock. Because preferred stock has various preferences/privileges that Common Stock does not, you can sell preferred stock for, say, $2.00 per share, while still making a credible claim that the Common Stock is worth a fraction of that.

At Formation

So how is it that founders and early employees are able to get millions of shares in their startups for practically nothing, without being taxed? Simple. At formation, the FMV of your startup’s stock is considered virtually nothing. Now, it’s certainly not worth nothing to you. But because you haven’t built an actual Company yet, the IRS accepts the argument that the huge amount of uncertainty and risk of failure make the stock worth fractions of a penny. We generally issue founder stock at a price per share equivalent to par value (usually $0.0001 per share). So an issuance of 2,000,000 shares to a Founder would require a check for $200.00. Assuming that founder files her 83(b) election (bad news if she doesn’t), she won’t realize taxable gains until she decides to sell her stock.

Note that this is also an argument for getting your founder shares and early employee equity issued as soon as possible.  The further along in your Company’s trajectory that you are (customers, revenue, investors), the greater likelihood that your Common Stock will have a higher FMV, and that the recipient will need to hand over meaningful cash either to you or the IRS in order to receive it.

After Formation, Financing

After formation, and as you move into seed funding, setting the fair market value of your Company’s stock becomes much more complex. Section 409A of the Internal Revenue Code is largely what drives that complexity, which this post is not meant to cover. The nutshell is that before a full venture capital financing, your lawyer will recommend that your Board of Directors use various “illiquid startup” guidelines to set the FMV of your stock.  After a VC financing, you’ll likely get a formal 409A valuation from a bank or valuation firm, and use that to set the exercise prices of your options. There are a number of reputable valuation firms in Austin that we recommend to our startup clients, and, as with hiring a lawyer, you should be careful about going with the firm that offers the lowest price. That can come back to bite you.

Take-home message:

  • FMV is related to (but not the same as) your or a potential investor’s value of your stock.
  • Issue equity and equity incentives as early as possible to avoid taxable gains.
  • To avoid “tainting” the FMV of your Common Stock, never sell Common Stock in a cash financing.
  • Consult with your attorney about setting the FMV of your stock as your company progresses.

Obligatory Disclaimer: I know you’re smart enough to know this, but this is not tax or legal advice. Things might be different in your particular context. Contact a professional before making a decision you might regret.

DIY Startup Legal Tools: Self-Diagnosis v. Self-Treatment

Image by Barbara Krawcowicz via Flickr

I have an awesome idea for a startup. Let’s call it LunaDoc. LunaDoc will be a website where you answer a series of algorithm-based questions about a health-related issue you’re dealing with, and then it will suggest to you a diagnosis. Sounds great, right? That’s probably why dozens of these exist already.

But let’s go one step further. After diagnosing you, LunaDoc will generate a prescription and send it to your pharmacy of choice, after which you can pick it up without the hassle or expense of ever having to talk with an actual physician.

If you’re half sane, you should have suddenly thought something along the lines of, “Whoa there, tiger.” Why is that? Because self-diagnosis, or educating someone enough to better understand their problem, is great. But self-treatment, or turning that new knowledge into a high-stakes action with potentially permanent consequences, without consulting a professional, can be absolutely nuts.

Sidenote: As I’ve done many times before, I’m going to leverage this healthcare example into a metaphor for the startup law context.  I truly believe there’s a lot that people in startup law can learn from the healthcare profession, so I’m going to milk this metaphor until the cows come home.

Self-Diagnosis

For years entrepreneurs have been fortunate enough to have an incredible amount of accurate, well-articulated, and free knowledge about startup law issues on the web; some in the form of blog posts and some in the form of articles. I’m a huge fan of recommending online resources to clients as a way to educate themselves without being billed hundreds of dollars an hour for it. And it makes the time that I personally spend with them more efficient (and cost-effective) because we can get right down to business without having to go through basic stuff. I keep my stash of helpful online reading here: SHL – Startup Law Links. 

Startup law blogs and articles are the legal equivalent of healthcare websites that help with self-diagnosis. Their role is simply educational, and can help a client (patient) better engage a professional in turning the diagnosis into a solution. While some doctors might complain about patients becoming “google doctors,” a more educated client base is uncontroversially a net positive.

Self-Treatment: Guided v. Unguided

Lately, however, we’re starting to see the web do what it always does: provide tools that attempt to dis-intermediate an economic relationship and let people completely handle things themselves. Self-diagnosis is evolving into self-treatment.

Major law firms have started posting standardized contracts on their websites for free.  Capography, a really cool new tool, lets entrepreneurs manage their own cap tables and even run a limited number of waterfall analyses to see how funds would flow in an exit. Docracy has emerged as an incredible source for hundreds of free contract forms for a wide variety of contexts, and they even let you execute the contract from the comfort of your own home, without ever having to go through the hassle or expense of talking with an actual lawyer (sound familiar)?

The much greater danger with these kinds of tools, much like with LunaDoc, is the issue of permanence. Education is flexible and easily correctable, but treatments are forever. Or perhaps better said, contractual and transactional mistakes are often extremely expensive to fix, if they’re fixable at all.

While everyone knows how much of a fan I am of standardization, automation, and any tool (toy) that allows attorneys to avoid repetitive, boring tasks, the fact of the matter is that tech startups are not coffee shops, and startup contracts are not wills. As I’ve mentioned before, startup law is a multi-specialty, highly contextual sport.  There are countless tax, employment law, securities law, and other state law issues that might come into play in your particular context, some of which need to be handled in the contract, and others that are completely separate from it. Signing the wrong contract, or taking the wrong legal action, isn’t that different from taking the wrong pill.  The side effects may be serious, or even lethal.

But, wait, aren’t law firms themselves putting up these standardized forms? Read the terms of service, my friend. Zero liability. Their skin isn’t in the game. Just yours. Those are marketing tools.

Attorney-Directed Self-Help

There’s a slightly different approach that a few companies are taking to allow entrepreneurs to do some things themselves and minimize their legal spend, while ensuring that a professional who understands the context is guiding the process. Brightleaf has a brilliant concept called a Leaflet. After speaking with a client and understanding what they’re trying to do, an attorney can easily turn a form into a self-help, automated tool. For example, you can turn the Company’s board-approved Option Grant form into a leaflet that allows the client to input the name, date, etc., and auto-generate option grant forms without bothering his law firm. Of course, every time you generate a form, the attorney sees it. Self-help, but with an experienced and invested professional making sure you don’t blow something up.

VCExpert’s Private Company Analysis Tool (PCAT) allows a law firm to input and update a Company’s capitalization info, and a client can then run any number of reports using that data without having to consult the attorney. Again, someone’s there making sure the inputs are correct and that things don’t go awry, but the client doesn’t have to ask his attorney to generate a different report (often hours of work) every time he wants to see the vesting status of options or the funds flow of a potential exit.

Empowering clients and unlocking information from artificial silos is awesome. Pretending that technology can completely replace professional judgment and contextual understanding when it simply can’t… not so much.

Yes, I understand that self-help tools are really about the under/un-served.

Of course, downloading a free contract form drafted by someone who at least knew what they were doing is light-years better than issuing stock with a 3-line contract written on a napkin.  And that’s why I’m not going to say that un-guided self-help tools aren’t a benefit to the startup ecosystem.

Much like how cheap, mass-market contract websites have made wills and basic corporate forms available to people who would never have contacted an attorney to begin with, I get that there’s an underserved market here that needs these tools.  Just keep in mind that how much effort and expense you’re willing to incur in protecting your startup is, in many ways, a reflection of how seriously you take its prospects.  If you’re sitting on a dud, who cares if your employment forms aren’t enforceable in your state, or if you didn’t fill out your stock issuance forms correctly? But if you think it’s a home run (and why would you waste your time on something that you think isn’t?)… well, you get the idea. Investors will too.

Why law firms should act more like medical practices.

If I try to schedule an appointment at my doctor’s office and my general practitioner or nurse practitioner (we’re assigned to both) aren’t available, either because they’re out of the office or don’t have time, guess what happens? I see someone else. If a client calls or e-mails her law firm and the partner & associate (usually assigned both as well) are either out or too busy to respond, which is often the case, guess what happens? She waits for them to become available.

Why the difference? Healthcare patients can be flexibly transitioned between different practitioners for general matters, while legal clients are generally stuck with the people they always work with, even for completely basic stuff.  You’d think that with the cost of a medical error seeming to be much higher than the cost of a legal error, reality would be reversed… but it’s not. While part of the answer has to do with professional culture and the way law firms are structured, the more practical reason has really to do with only one thing: records.

Any remotely competent medical practice maintains a thorough set of internal historical records on its patients. More importantly for purposes of this discussion, they maintain a narrow set of standardized, easily reviewable information that a physician could quickly read to understand the most critical issues that are likely to interact with whatever the patient needs addressed at the moment: prescriptions, previous medical conditions, previous procedures, family history, etc. Let’s call this an electronic health record, noting that we are talking about internal records within a practice, not the bigger problem that standards for maintaining records across practices in our healthcare system leave a lot to be desired.

Shockingly, for most law firms anything remotely resembling a well-organized, easily reviewable electronic legal record is completely absent from their business processes.  Want to know the key info about a company that needs you to quickly draft them some bridge documents? Start reviewing the documents the last guy drafted.  This is equivalent to a doctor having to review all of another physician’s dictated notes every time he’s assigned to a new patient. It’s inefficient, if not frustratingly moronic.

In our office I introduced a very simple concept that addresses this problem only for the most basic of information. We call it a Company Snapshot – a single page document that anyone assigned to a client can review in 3 minutes to know the exact name of the Company, state of incorporation,address, key contact info, who’s on the board, and a few pieces of other useful information.  It doesn’t go anywhere near addressing the fundamental problem described above, but it still prevents a fair amount of pointless document reviewing whenever a junior attorney needs to draft a simple document for a newly assigned client. One could easily imagine the concept being extended to providing a clear timeline of key events/transactions in a Company’s history, a summary of its capital structure, and notes regarding any abnormal issues that would usually throw a wrench in getting some basic legal work done (equivalent to an uncommon medical condition –mine would be having only one kidney– that any physician treating a patient needs to know about).

I don’t have the clout, at least not yet, to push anything broader in scope than the Snapshot, but I would hope that other firms are working toward a similar goal.  The lives of attorneys would be much-improved if they could optimally shift work among themselves when a single attorney is too busy to serve all of his usual clients. And clients would be better-served if, when all they need is to grant some options or issue some bridge notes, they don’t have to wait for their attorney to close that big M&A or VC deal that’s been consuming his week.  One partner in our firm described it as a shift from tribal knowledge to institutional knowledge. Whatever you want to call it, it needs to happen.

Why experienced entrepreneurs hire better lawyers.

There are goods and services for which quality is apparent to the consumer from the beginning, and then there are those where what you actually got for your money can take years to figure out.  Transactional lawyering is decidedly in the latter category, although it often takes a client some personal seasoning (or good advice) to figure that out.

Fundamentally, there are two “jobs” that a client will typically hire outside corporate counsel for in a transaction. The first is getting the transaction done. This is the job that all clients are aware of, no matter how much experience is under their belt.  As long as the client gets his/her desired economic terms, papers get signed, and wires get initiated, all seems to have gone as planned.

But the more experienced entrepreneurs (and unfortunately that experience often isn’t pleasant) know that good legal counsel will serve a second function. While not as simple to define as the first, let’s call it transactional insuranceSome illustrations would be helpful here.

Formation. You have a great startup idea, got together with some co-founders, and want to make it official. You incorporate, issue some founder stock, perhaps authorize an equity plan, and you’re good to go. Put the papers away and forget about them. No worries here, right?

  • What if one of the founders later claims that some of the Company’s IP is his/hers and not the Company’s?
  • What if some of that founder’s work was done on a prior employer’s time/hardware, and that employer now claims ownership of the IP?
  • What if one of the founders dies? Where does their stock go?
  • What if one of the founders gets divorced. Where does their stock go?
  • What if a founder decides to leave the Company after  a year? Where does their stock go?
  • What if someone sues the Company and you personally?
  • What if the IRS comes back 4 years from now and says you owe them a bunch of $ on your vested stock?
  • What if it turns out that a founder had a non-compete agreement with a prior employer with deep pockets, and working at your Company violates it?
  • Insert 3 dozen other scenarios here.

VC/Angel Financing: Everyone signed the papers and sent you checks. Awesome. No worries, right?

  • What happens if we decide to sell the Company early?
  • What happens if we want to raise a new financing, but not all of our current investors are on board?
  • What if an investor decides 5 years from now that he wants his money back?
  • What happens if the IRS claims 3 years from now that we issued stock at too cheap of a price and tax is owed?
  • What happens if an angel investor sues the Company claiming that we fraudulently withheld information from them?
  • What happens if the SEC claims that we sold stock illegally to unqualified investors? Wait, what does college football have to do with this?
  • Insert 3 dozen other scenarios here as well.

The quality of the process and legal drafting that took place in the above scenarios will determine whether a resolution could be as simple as (i) pulling up a document, (ii) pointing to Section 2.3(a)(i), and (iii) getting back to work, or something that could destroy years of hard work in an instant.

From the perspective of a lean entrepreneur who just wants Minimum Viable Lawyering, signing some papers provided for free or a few hundred bucks felt like success.  But experienced entrepreneurs typically have a better sense of the nightmare they may be inheriting by going with the attorney or firm who claims to do the exact same thing as the “overpriced” guys, but at a substantial discount.

Granted, there is a lot to be said for Job #1, and there’s no shortage of movement in the legal industry toward getting the transaction done quickly and cost-effectively.  That topic is the subject of perhaps 80% of my blog posts.  But something is only truly cost-effective when it efficiently accomplishes all of the tasks that you hired it for – not when it provides the trappings of a job-well-done, but kicks any number of disasters down the road.  

I can’t tell you how much time we spend cleaning up the work of bad lawyers who looked, at the time, like a bargain. Experienced entrepreneurs hire efficient lawyers. Inexperienced entrepreneurs hire cheap ones.

The Economic Deflation of Startup Law

News.  Two big issues have been floating around the startup law space lately. First, Yokum Taku introduced “convertible equity” in an attempt to address the potential downsides (for entrepreneurs) of convertible debt, which set off a debate that Antone Johnson spectacularly Storified. More interesting to me, however, was AngelList’s announcement that seed rounds can now be closed, soup-to-nuts, on their platform.  The real news there, for lawyers at least, is that Wilson Sonsini will close those rounds for free.  Yes, as in nothing.

Startup Law – Deflation Accelerating

Much has been written about the “deflationary economics” concerning startups and the web, with Mark Suster’s post probably being one of the best articulations that come to mind.  Not as much has been written about the indirect effects that industries experiencing economic deflation can have on other sectors they interact with.  Wilson Sonsini’s AngelList pronouncement is, in my opinion, the clearest sign that the portion of the legal sector working with technology startups is itself experiencing rapid deflation — and not because lawyers have suddenly shed their luddite tendencies and read ‘The Innovator’s Dilemma’ (though they should).

What’s happened, essentially, is that with literally every other service used by their clients becoming radically cheaper, and the resulting downsizing of investment rounds, startup lawyers simply couldn’t maintain their usual fees and keep a straight face.  This deflation started out with what you might call Stage 1 deflation, with standardized docs emerging, fixed fee packages, etc.  Startup Law was just efficient at this stage, especially compared to other areas of the law.  But with free, dynamically generated documents from high-end firms available online, and now with one of the best firms in the country saying they will close seed rounds for free, I’d say its reached Stage 2, where commoditized is the more appropriate adjective.  And I’d argue that this has some serious implications going forward.

How We Got Here

First, it’s worth reflecting on the different steps that startup law firms have been (or should be) taking in order to compete in this deflationary environment.  I’d break those steps into 3 categories: contractual, technological, and operational.  These steps could also serve as a model for other parts of the legal field that, while not as aggressively deflationary as startup law, will likely eventually follow a similar path.

Contractual. 

  • Standard Firm Docs – In order to make contract drafting more efficient, firms started modularizing the language of their own documents.  If an investor gets a 1x participating liquidation preference with a 3x cap as opposed to the 1x non-participating currently in the document, ‘drafting’ involves mostly cutting and pasting bracketed language, with minimal tinkering.  While this cut down on internal drafting, it still left room for bickering about language with the other side of the deal.
  • Universal Standard Docs - Going one step further, standardized investor docs like the Series AA and the NVCA Model docs emerged, allowing for parties on both sides to have a common language framework to work from.

Technological.

The contractual efficiencies developed in startup law still required the usual process of opening a word document, filling in blanks, moving around language in a very straight-line fashion, and then proofing to make sure everything is coherent.  Closing required creating signature packets, then tracking signatures and assembling them back into fully executed copies.  But then technology emerged to streamline a lot of this process.

  • Proofing Software – A significant amount of time on a transaction used to be spent by junior attorneys flipping through pages to make sure names are properly spelled, commas are in the right place, and defined terms are properly in place.  Software like Deal Proof emerged that can scan a document and generate a proofing list for an attorney, cutting down on that proofing time by anywhere from (my estimate) 50-75%.
  • Document Automation – Companies like Brightleaf have emerged to turn the cut-paste-and-proof process of working with form docs into one of simply clicking certain options in a form.  Want that 1x participating LP w/ 3X Cap? Just click the right box in your template, and the language will get filled-in automatically, and every other area of the document that is impacted will also be modified. No need to proof.
  • Electronic Closing.  -  With multiple parties often signing dozens of documents, the usual closing process involved creating “signature packets” where you PDF’ed the signature pages of each contract, and created single files containing all the pages that each individual party had to sign.  Without doing this, mistakes would be inevitable.  With electronic signature software like Docusign, this process is largely removed.  Put the ‘Sign Here’ tabs for each person in the appropriate places, and Docusign will (1) guide them to where they need to sign, and (2) generate fully executed documents.

Operational.

One obvious end-result of the contractual and technological developments has been that drafting simply takes a lot less time, which naturally means less money billed.  But what they’ve also done is made the drafting and closing process a lot simpler.  To modify a vesting schedule or a liquidation preference, you don’t really need to understand the actual mechanics of the language. Just click the box.  And to get a deal signed up, you don’t need to create complicated signature packets and coordinate signatures.  Just drop the Docusign tags in the right place, and it’ll do the rest.

Firms have taken advantage of this simplicity by pushing work down to junior attorneys and even paralegals, who bill a lot less per hour.  Where it might have previously required an experienced attorney to draft and close a seed financing, an innovative firm might have a paralegal do 95% of the work, with zero drop in quality.  A partner or senior attorney might spend a few minutes discussing very high-level issues with the client, but that’s it.

The Next Step: Deal Platforms

I have zero doubt that Wilson Sonsini is taking advantage of all three of the above categories.  But the key to really get the kind of deflation reflected in the free AngelList closings is the next step of legal technology: Deal Platforms.  Rather than just the initial drafting of docs being automated, with negotiation over terms and language to follow, the automation becomes bilateral.  If the investor wants a better liquidation preference, he simply fills in a field or checks a different box, and if the Company disagrees, they uncheck that box.

Contract language becomes completely secondary – commoditized – on a deal platform.  One can easily envision a time in which the negotiation of a full venture deal, not just a convertible note financing, involves nothing more than checking boxes and filling in a few fields, with full documents automatically generated and then electronically signed.  The chances of closing such a deal for free are practically zero, but all that automation could make a ~$10K legal bill for a full institutional venture capital financing a reality, which would be about a 50-80% cut on current rates.

Takehome: Nobody should be myopic enough to expect AngelList-like automation to stop at the seed deal stage.  Again, The Innovator’s Dilemma, legal version.  See below from AngelList’s Q&A.

Does Docs support Series A rounds?

No. Docs only supports seed rounds right now. (emphasis added)

Implications: Freemium Startup Law

There are a number of ways that this rapid deflation has and likely will impact the structure of startup law practices.  One result of the already-occurring deflation has been the growth of boutique firms competing with BigLaw by offering similar, albeit more limited, services at lower billable rates.  I wrote about this previously: ‘In Startup Law, Big Can Be Beautiful.

The economic advantage of a boutique practice is that firms can avoid the high billable rates necessary to sustain the breadth and overhead of large law firms, while still offering their experienced attorneys comfortable salaries.  That works well in an environment where the demand is for cheaper seed financings and venture deals. But what happens when free or practically free becomes the dominant expectation?

Cross-subsidize.  As Wilson Sonsini’s move has made absolutely clear, large firms have their own economic advantage with respect to legal fees: cross-subsidizing low-end work with profits from larger deals.  Large firms don’t just handle formations, seed financings, and venture deals, they also handle cash cow M&A and IPO transactions that are not experiencing anywhere near the kind of deflation going on at the low end.  Those deep pockets make offering free startup work a lot easier, provided enough of the loss-leaders generate big deals down the pipeline.

This model of offering a lot of stuff for free and profiting off of the high-end users should look very familiar to techies: it’s the freemium model, applied to law.  And it distinctly favors large, brand-name firms.  Boutique firms lack the institutional capacity to handle the large transactions that a larger firm can use to cross-subsidize free work.  Without more radical change, their only hope is to make up for deflation with volume.  But [insert large number] * free doesn’t pay the bills.  Commoditized deal work favors the cross-subsidization of large firms over the lower labor costs of boutique practices.

Conclusion: Move Fast, Move Up, or Move Out

At this point (when deal platforms become ubiquitous), I see smaller startup law practices having to either (A) get used to operating at much lower margins, or (B) find a way to move up-market and take a piece of the larger deals.  I wrote previously about the possibility of boutiques using technology to scale for large transactions here: The Ad-hoc Law Firm? Granted, I don’t have much visibility into how boutique practices are doing, though I’d love to hear from other attorneys or knowledgeable people on how they see the future panning out.

As for large firms operating in this space, the choice is much more straight-forward: either become radically efficient with your commoditized startup work in order to keep the pipeline flowing, or get out.  I’ve seen firms here in Austin completely exit startup work for exactly this reason.  Thankfully, we’re going with the other option.

Legal Startups: All Chasm, No Revenue

Kenneth Adams over at Koncision wrote a blog post recently that caught my attention: The Perils of Innovation, about the challenges of true innovation in the corporate law field.  Take-home point:

Bringing innovation to the transactional world is like competing against a giant cartel. It’s like competing against faith. That’s what makes it so bracing, but it’s also why most people offering technology solutions to the transactional world will fail.

I started commenting on his post until I realized I was writing a mini-essay and that, given the relevance to other topics I cover, it made more sense to post here.  Ken talks about the recent shut-down of Ridacto, a little contract analysis tool that I came across – wait, now that I think about it, Ken was the one who introduced me to it, via Twitter – and found interesting, but a bit shy on execution. You uploaded a contract (more on that later), it ran an analysis, and then produced a proofing report that pointed out issues with defined terms, section references, etc. Much like a simpler version of Deal Proof, which my firm licenses but for some reason no-one used until I discovered it.  It’s highly imperfect, but has honestly saved my life as a junior associate, and has saved the clients I’ve worked with probably about 5-figures so far.

Here’s my comment to Ken’s post:

I’m pretty optimistic about the future of transactional legal tech, but I think that any startup trying to enter the space has to be incredibly strategic about how they build momentum.  I tried Ridacto – it seemed interesting, though the UI was a bit confusing.  But I think the real issue was that their approach to how they analyzed contracts would simply be a non-starter at a law firm of almost any size – hey, upload this contract for a private transaction that hasn’t occurred or been announced yet, we’ll analyze it for you, but we promise we’ll delete it afterwards!  Umm, yeah, good luck with that one.  I got my hand slapped by my IT overlords because Box, not Dropbox, but crazy-secure used by like the CIA Box, wasn’t secure enough for them.  Just suggesting Ridacto would get me laughed at.

Lesson: If you’re a legal startup, your customers, or at least those controlling their buying/use decisions, are pathologically paranoid about security and credibility.  You simply can’t be a $100K, bootstrapped, “lean startup” and expect to get any momentum in this space.  In some ways, you never get to truly enjoy the Early Adopter phases of most tech startups. You start out right in the middle of Geoff Moore’s famous “Chasm” – all the problems of a startup – burning cash, an un-proven business model or product + all the problems of a scaling tech co. that usually has revenue to rely on, like gaining credibility and convincing conservative customers.

The last sentence or two is a point I want to drive home.  The transactional legal field does have early adopters who love playing with new toys, myself included, but we’re (i) few and far between, (ii) usually at the junior level, and (iii) as a result, don’t control the purchasing decisions of our firms.  As a junior, I’ve recently been able to convince our firm of about 4-500 lawyers to trial two pieces of tech that can, and already are, transforming parts of our practice.   One of those is a true startup – BrightLeaf. But there are a number of factors that had to be in place before I could do that:
  • Price – low up-front cost, subscription based. If it doesn’t work out, we make a clean break, little money lost.
  • Trial Period/Demo – don’t expect any firm to consider your product unless you offer a trial, or at least a demo that they can play with.  Demos can be helpful where the firm would need to build in a bunch of of its own information to truly get a feel for the product.
  • Security – I’d have every single aspect of our firm in the cloud if I could, but I have to answer to IT people who get panic attacks at hearing the word “dropbox.”  If you’re handling anything with sensitive information, you need security credentials, and that isn’t cheap.
  • Credibility –  Hire ex-corporate lawyers that can sell – good luck finding them.  Network and get in contact with a single firm that (i) is an industry leader, (ii) has people who are willing to trial software – most likely tech-focused lawyers, and (iii) would allow you to mention their name in marketing materials.  Lavish them with attention.  Most law firms are sheep. Nothing perks the ears of a corporate partner better than “Well, X and X LLP are using it.”  That’s how legal language gets adopted. Same with legal tech.

Low up-front costs for customers and trial periods/demos, so not much revenue to rely on up-front – classic startup.  Security and credibility to convince conservative decision-makers that you’re legit, will make it past their IT people, and truly understand their problems – that’s the Chasm, and it costs money.  Usually a tech co. has some revenue from early adopters to rely on when its dealing with the Chasm, but not a legal startup.  You start out right in the middle of it.

Good luck being a true “lean startup” in this space.  Frankly, I think that an intrapraneur – operating with the brand and budget of a large Co., but with the freedom to innovate – has much better odds than a true entrepreneur running a legal startup. I know many VCs aren’t (yet?) pouring money into the legal space, but we’ll see.  We desperately need innovation, but it’ll take serious, well-funded risk-takers with a strong understanding of corporate law practice (not an easy combination to find) to make it happen.

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