Why I left a big law firm, but not BigLaw.

While I’ve devoted the majority of this blog to providing free resources on startup law and finance to startup entrepreneurs, I occasionally take the time to write about the economics of law firms and why entrepreneurs would be wise to understand it at a high-level.  This post will start out with a historical summary of positions I’ve taken on the subject, with links to applicable posts, and then branch into my decision to move my own practice and clients to a new type of firm – not BigLaw, but not quite traditional BoutiqueLaw.

  • The Economic Deflation of Startup Law – Early stage startup law, much to the benefit of entrepreneurs and top-tier lawyers, has become increasingly automated and commoditized. The end result is a form of “freemium” law practice, where (i) entrepreneurs can obtain quality representation for very little money, and (ii) quality lawyers can, thanks to automation, engage entrepreneurs early on without having to discount fees, defer, or any of the other old-school ways of obscuring the cost of legal services. Low-quality or narrowly focused “cottage” lawyers will struggle because their bread-and-butter work will have little to no margin, while higher-tier lawyers will thrive on their pipeline of later-stage, funded clients, which cross-subsidize early-stage work.
  • In Startup Law, Big Can Be Beautiful – Breadth and scalability are absolutely essential to the proper representation of a startup, and large firms have historically been where to get that.
  • Integrated Startup Law – Specialists Matter – Technology startups do not need and should not want unscalable, narrow “small business” legal representation. By their nature, they will need a broad set of legal specialties – Tax, Labor, IP, Regulatory, etc. – along the course of their business cycle, and failing to choose a firm at the beginning that can efficiently coordinate all those specialists will become a big problem. The analogy to healthcare is important. Also see – The Cost of “Staging” Your Startup Lawyers.
  • The Ad-Hoc Law Firm – The ability of networks of small law firms to coordinate efficiently will allow for (i) the replication of BigLaw’s breadth and experience, without its overhead and inflexibility, and (ii) the scalability that boutique firms alone can’t provide.

Nutshell Summary: BigLaw offers experience and breadth, but is largely over-priced and inflexible. Boutiques are cheaper, but often narrow and incapable of truly scaling, and their work is being commoditized.

BigLaw Beginning

So in my own career, I started out at a big firm with a group of fantastic lawyers whom any startup would be well-served by, but I increasingly butted heads against the firm’s (separating the lawyers from the institution is important) policies, including (i) IT policies with respect to new technology that needed to be adopted, (ii) billing policies around how to charge startup clients, and (iii) personnel that simply didn’t want to do things differently and weren’t incentivized to care anyway.

Your Boutique Can’t Scale

I watched the market, and had some overtures from boutiques in the area, but every time I came away underwhelmed:

  • Lower Pay, Lower Lawyers – Often the boutiques had very low rates, but their lawyers made a lot less income.  True innovation is about doing more for less while earning more – it should be win-win economically on both the client and the lawyer’s end. That’s why the most disruptive startups aren’t in it to make less money, they’re in it to make more money, but on a model that makes the end-price lower by cutting out fat, not bone. If your firm is built on paying lawyers less – guess what? You’re just going to attract lower-quality, less ambitious lawyers. Surprise, surprise. Anyone can lower their price tag.
  • Where are the partners? – Many firms were effectively run by senior “associates” (attorneys from big firms who never built the experience or client base to become partners) who started their own firms and donned the partner label.  Early-stage clients might not care about this because their interactions are usually with associates anyway, but they should if they intend to become later-stage clients.  A lack of true partner experience within a firm can mean (i) your late-stage startup is effectively funding on-the-job training, and (ii) that training can lead to mistakes.  A scalable firm needs true partners that have played the end-game and won, otherwise top clients will have to leave.
  • Where are the specialists? – No one had a good answer for how to efficiently provide full service legal representation to clients. Asking them to engage a dozen firms on a piece-meal basis and manage a dozen different bills is not the right answer.
  • Luddites – If you think a lot of law firms haven’t joined the 20th century with respect to technology, check out some boutique law firms.  A lower rate is often used as an excuse for being inefficient and taking longer to do something.  Smart clients realize that their legal bill is a two-part equation: rate * time spent.  And if their lawyer is taking forever to do basic stuff, the lower rate is a mirage.  Startup law is for technologists, not cottage industry practitioners.

So why did I move my practice to a smaller firm (Miller Egan)?  Addressing the above issues in order:

  • The compensation structure is designed to attract top talent lawyers, not people who are looking for semi-retirement.
  • The firm is built and run by partners who were partners at the country’s leading law firms, but got fed up with the bureaucracy and inflexibility.  This means the firm can truly handle, and investors know they can handle, scaled, late-stage clients.
  • The firm has a well-developed network and process for coordinating specialist counsel for clients when needed, so clients can get the full service representation they’d receive at a big firm, but under a far more efficient model.
  • Technology? I’m CTO. #Howyalikedemapples

The above post should be read as a clear message to both traditional BigLaw and traditional BoutiqueLaw. Big can be important, and boutique can be cheap, but small and scalable may eventually eat your lunch.  And let me tell you, that lunch is delicious.

When do I “really” need to qualify my Delaware-formed startup in Texas?

So you’ve formed your Texas-based startup in Delaware.  You’ve paid your filing fees, filed your 83(b)s, and, if applicable, paid your lawyer. What’s left? Qualifying as a “foreign” entity to do business in Texas. Think of it as Texas’ way to punish you, via a $750 fee, for not incorporating in the mother land. It’s also the mechanism by which Texas can begin to bill you annually for state franchise taxes.

Link to Qualification Form

Do I really need to pay this?

While the gut reaction of most lawyers is to just make you pay the fee at formation, $750 is a pretty sizable amount of money relative to a formation’s total cost. So the inevitable question is, can I hold off on paying it? Maybe. Registration must occur within 90 days of “transacting business” in Texas under the Texas Business Organizations Code. But what exactly is “transacting business?”

Under TBOC 9.251, these are some activities (the list is non-exclusive) that do not constitute “transacting business,” and hence don’t require registration (shortened for relevance):

  • Holding a meeting of officers or shareholders re: internal affairs of the Company;
  • Maintaining a bank account;
  • Effecting sales through an independent contractor;
  • Transacting business in interstate commerce;
  • Conducting an isolated transaction that’s (i) complete within 30 days, and (ii) not part of a longer series of transactions;
  • Owning real or personal property.

A general rule of thumb is that it’s time to qualify when you have employees in Texas, apart from founders.

What happens if I don’t pay?

Failing to register in Texas at the right time leads to the following:

  • Inability to maintain an action/suit in Texas court;
  • Possible injunction from the state of Texas;
  • Civil penalty equal to fees and state taxes that would’ve been imposed if you’d registered at right time;
  • Late filing fees equal to (i) number of whole and partial calendar years unregistered, multiplied by (ii) $750.


A. Issuing shares, having a bank account, performing internal corporate activities, selling through independent contractors, and doing one-off short transactions do not require you to qualify in Texas. Doesn’t this sound like a lot of pre-seed startups with one or two founders (no full-time paid employees) coding away on their MVP?

B. If you ever need to maintain/defend a suit in Texas courts, or if for some crazy reason the State of Texas decides to file an injunction, you can just register at that time, and

C. If it turns out you register too late, the penalty is $750 for each year you were unregistered, and any taxes you would’ve had to pay anyway.

I’m not going to make any recommendations here, but I think a lot of founders might read between the lines and choose to delay that $750 check to the State of Texas until either (i) funding is on the horizon, (ii) they’re actually doing deals instead of just building a product, or (iii) it’s otherwise more clear that they’re “transacting business” in Texas.

The Deflation of Startup Law Continues: Clerky

Almost exactly a year go, I wrote a post (The Economic Deflation of Startup Law) in which I (i) documented how the rapid adoption of technology and standardized contract language in early-stage startup law was dramatically deflating the cost of quality (crappy law has always been affordable) legal services available for founders, and (ii) made a few predictions about how this might affect the segment of the legal market that serves early-stage tech entrepreneurs.


  • Contractual Changes – Standardization of contract language within law firms  & the emergence of universally standardized documents like the NVCA model docs, Series AA, and Techstars Docs, to name a few.
  • Technological Changes – Proofing software, Document Automation, Electronic Closing, etc. – reducing the amount of lawyer time required to complete a formation, bridge financing, etc.
  • Operational Changes – Technology and standardization simplify the labor input required to complete a transaction, allowing less trained, less expensive professionals to perform more of the back-end work.
  • Deal Platforms – Technology is moving from being merely a tool within the traditional law firm process to a bilateral platform that allows parties on both sides of a transaction to close, from beginning to end, with significantly less lawyer time required.
  • Freemium Startup Law – Very early-stage legal work (formations, bridge/seed financings, routine forms), once the bread-and-butter of solo lawyers and boutiques serving entrepreneurs, will no longer support those practices, no matter how efficient they try to be.  The margins will be too thin.  Those attorneys able to serve higher-quality, later-stage clients (those that make it to Series B, C, exit) where legal work will remain much more high-touch, high-margin will dominate the market and cross-subsidize their work for premium early-stage clients.  In short, Startup Law will move closer to a freemium model, where standard work is free (or almost-free) and being able to attract “premium” clients is essential for profitability.

The point of this post is not to comment on the accuracy of my predictions. One year is too short a time-frame to judge (we’ll see in 3-4 more years), though I will say that in Austin’s legal market I’ve seen a definite trend of solo and almost-solo lawyers attempting to expand their practices into multi-specialty firms, suggesting their desire (or need) to move up-market. Nationwide, I’ve also encountered a few small firms with much higher-caliber partners/associates, broad networks of specialists, and low-overhead platforms to compete head-on with BigLaw: this is where things will get very interesting.

Deflation 2.0 – Clerky

Instead, I’d like to talk about how the above developments have manifested themselves in the form of a Y-Combinator startup called Clerky. Details:

  • Founders are UPenn and Harvard (represent!) JDs of Orrick pedigree, and the head partner of Orrick’s Emerging Companies Group is an advisor; lest you question the quality of the drafting.
  • Appears to have handled formations for several Y-Combinator classes (note: classes – hundreds of companies) over the past several years; lest you think they haven’t been vetted and won’t get traction.
  • For formations, founders fill out online questionnaires very similar to those used by startup-focused law firms, and documents are automatically populated with the appropriate names, numbers, vesting schedules, etc.
  • There is a “reviewer” option where the founders can designate a person (an attorney) to review the final documents pre-execution to give a thumbs-up.
  • Execution is handled electronically on the platform.
  • Delaware filings and registered agent registrations are handled by Clerky.
  • Final executed documents are stored online.
  • Currently Available: Simple Incorporation (no equity, IP docs, etc.) – $99. Full formation (equity docs with vesting, IP assignment, bylaws, etc. – option plans and indemnification agreements coming soon) – $398.
  • Coming Soon (In Private Beta): Employee Offer Letters, Consulting Agreements, Advisor Agreements, NDAs, Convertible Notes., LLC to C-Corp Conversion

So what exactly has Clerky done? Once they get option plans and indemnification agreements up and running, they will have taken what would cost $5K-10K in legal fees at an inefficient law firm (or $2.5K-$5K at a more efficient one) and reduced it to $398 by going one step past building tools for lawyers to developing a platform that effectively replaces them – or at least ~95% of the work they do for early-stage clients. LegalZoom prices, but for premium, startup-focused documents.

What about free options?

Major law firms have attempted to address the large portion of the founder population for which even $2.5K-$5K is too high a formation price tag by offering documents online for free. I even wrote this post offering my own checklist for forming your own startup and issuing equity, lawyer-free, via publicly available documents.  But $398 is close enough to free that founders in this same category will be willing to pay for peace-of-mind, knowing that their docs are filled-out and filed properly, and that a reputable service is helping them maintain them. Plus it’ll save them hours of having to read the forms themselves.

Curmudgeon Criticism 1: Founders will want more customization than Clerky Offers

Yes, there will always be a segment of the founder population that wants high-touch, custom lawyering from the very beginning and will pay for it; just as there are people for whom Nordstrom or Macy’s isn’t good enough for their clothing and require tailors and boutiques.  But the reality is that for the large swath of the pre-funding founder population (95%+) that just wants to “get the job done” and focus on their product, Clerky, with its 80-90% discount on even the most efficient startup lawyers, will be a viable option. Those lawyers who’ve offered quality startup formations for $2.5K have themselves done so by limiting the amount of customizability and focusing on standard terms, so the difference in terms of documents between what you would get from a lawyer v. from Clerky will be very small.

Curmudgeon Criticism 2 Good lawyers will never accept a third-party service’s drafting language for their own clients.

After an inevitable phase of whining, kicking, and screaming, smart lawyers will accept whatever good clients and the market dictate, or they’ll just leave the space.  As stated above, there will always be clients who are willing to pay a premium for ensuring that all of their lawyering is 100% airtight, but those clients will be fewer and farther between.  And you can certainly expect a chorus of lawyers poking through the Clerky docs with a laundry list of ways their own documents are better. But like many disruptive innovations, it’s about the ratio of quality to cost, not absolute quality. At $398 for documents based on those used by one of the country’s leading tech firms and delivered by a YC company run by Ivy-League JDs, the value for founders is unquestionable. Quality, both in terms of legal drafting and user experience, will also improve over time.

Clerky will allow founders to engage quality, scalable lawyers earlier on.

Clerky’s “reviewer” option and its clear intent to incorporate lawyers in their processes shows that the goal here is not to completely replace lawyers, which would clearly be silly and reckless. The nuances of individual circumstances, the need for sound professional judgment that can’t be reduced to an algorithm, and the general realities of running a company will always require good, human legal counsel.

What a service like Clerky does is allow founders with very low legal budgets to stop having to settle for low-quality, mismatched lawyers who end up costing a whole lot more money (in mistakes) than founders expect. As I wrote in a previous post, a lot of founders know they need a lawyer, but can’t afford a good one, so they take the “staging” approach of going cheap up-front with plans to “upgrade” later. The consequences of this approach can be very expensive, and often disastrous.  Founders need lawyers that can serve them at all stages of development, not just when they’re tiny and the stakes seem low.

With Clerky, the “cost” of hiring a good lawyer at the very early stages of a startup can be the time it takes to quickly review some Clerky docs and answer any questions a founder might have about non-standard matters. For quality startup lawyers who stop pretending that all document drafting, no matter how routine, needs to occur in private silos, this is liberating. They can focus their practices on more complex matters that are far more profitable and interesting from a professional standpoint, while still maintaining relationships with early-stage clients who might one day require their skills. It also means the need for deferring fees will be dramatically reduced.

A missing piece: what do the documents say?

One issue that has gone under-addressed in the startup legal landscape is how to make all these automated legal documents understandable to founders.  While no founder should care to understand all the nuances of their option plan, stock purchase agreements, etc., they should at last be able to grasp at a high-level the concepts that they contain.  And sitting down with a lawyer for every explanation is and always will be too expensive for most founders.

Offering lists of books and links to founders is very helpful.  A “customer support” model of cheaper professionals without JDs who can easily answer common founder questions will also likely emerge.

One startup here in Austin is taking an interesting approach: crowdsourced annotations of contracts (Lawful.ly). They call themselves the “Rapgenius for Law.” Imagine having all of the legal forms that your startup uses available online with annotations, so you can click around the document and get plain-english explanations of what a particular provision means. That’s what they are working on, and hopefully it (or something similar) will fill a gaping hole in the early-stage startup law landscape.

For lawyers who’ve built their practices on charging clients thousands of dollars for basically filling in forms and doing some cutting-and-pasting, the future looks increasingly grim. For those of us who love working with entrepreneurs and tech companies, but find cookie-cutter legal work utterly boring and a waste of our intellect, life is getting a whole lot better.

Founder Convertible Notes – Put Your Money on the Cap Table

It’s quite the norm for a startup to run on its own founders’ sweat equity and personal funds (bootstrapping) until the Company is able to raise outside capital.  A very important question that isn’t asked often enough is, “how do I paper the money I’m putting in?” Does it just go in and disappear? Does it pay for my stock?  While there are + and -s to different approaches, the answer that I almost always arrive at is: treat yourself like an investor.  In other words, paper your bootstrapping in a way so that it goes (eventually) on the cap table.  You benefit economically, and investors actually like to see evidence that you put more skin in the game than just your time.

  • Don’t use it to buy Common Stock – Your Common Stock should almost always be issued at par value ($0.0001 per share or some similar number in your Certificate of Incorporation) at the very beginning of the Company. This is proper because the Company is worth very little from a “fair market value” perspective, and issuing it at a higher price sets a FMV precedent that ends up hurting later employees because they then have to pay that higher price too.
  • Don’t buy Preferred Stock – Unless you’re a seasoned entrepreneur, the documentation and terms are too complicated for you to handle at the very early stages, and you’re not experienced enough to set a valuation. You’ll likely end up setting a bad precedent that will come back to bite you if you bring on real investors.
  • Don’t treat it as a loan – How do you think it looks to an investor if you’re asking them to actually invest (not loan) their money and risk losing it all, but you’re only willing to loan your personal funds? Bad.
  • Answer: Founder Convertible Notes – Issue yourselves convertible notes. Pre-financing, they are effectively a debt claim on your own company.  But upon raising the threshold amount that you set in the notes, they’ll convert into Series A Preferred Stock. This means (1) you now have a liquidation preference that will ensure you at least get that money back on an exit alongside future investors (unlike your Common Stock, which will likely sit beneath them), and (2) you get to vote those shares alongside future Series A investors.  Papering this is also a lot easier than buying preferred stock, and you don’t have to set a valuation.

Background Reading

Issues to Consider

  • Interest rate on the notes: 5-8% is fair
  • Discount on conversion: 20% is fair
  • Qualified financing threshold – $500K-$1M is fair
  • Cap on Conversion Valuation – Probably not a good idea for a founder note.
  • Maturity – Give yourself enough time to raise funding. 18-24 months is fair.
  • What happens at maturity? – Realize that at maturity, the notes will become “due.” This means the person holding the note can, if they want to, demand repayment (they could just extend otherwise) and cause all kinds of problems if they don’t get repaid.  If it’s just one founder or a couple of people you trust, this likely won’t be a problem. Make sure the maturity period is long enough, and be aware of the risk.  A lawyer could draft in extra protections to kick in at maturity, but that customization will cost money.

Good Forms to Use

  • Techstars has a great free set of Convertible Note docs to use here under “Debt Financing Structure. For founder notes, you don’t need the term sheet. While these aren’t rocket science, it’s still best to hire a lawyer if you want to completely avoid mistakes. But if it’s just one founder, or a small group of founders with no legal budget, they could probably handle this on a DIY basis if they read carefully.
  • Note that the Company’s Board of Directors should formally consent to the note financing. If you have a lawyer, ask for a simple board consent.  The reality is, however, because only the founders are involved, you can just ratify later when you’ve hired decent counsel.

The Cost of “Staging” Your Startup Lawyers

An unfortunately common problem that successful startup entrepreneurs have to deal with is outgrowing their first law firm or lawyer.  The reason for this is two-fold:

  1. High-Growth – Unlike traditional “small businesses,” startups that seek angel/venture capital are by their nature meant to be very high-growth oriented: they start out simple and small with tiny legal budgets, but within a matter of a few years (sometimes months) they can be raising capital from sophisticated parties, striking complex commercial deals, developing valuable intellectual property, and otherwise requiring serious legal advice.
  2. Short-sightedness – Because startups start out so small and often with non-existent legal budgets, founders will often plan to go with an attorney or firm that markets itself as serving “small businesses” at very low rates. The problem, of course, is that a “startup” and a usual “small business” are not the same thing, because of the first point above.

My thoughts on the “go cheap at first” attitude are already articulated in another post. In a nutshell, I’m of the mindset that because of the high-quality DIY resources available online for startups, founders might often be better off going it alone, until they can afford real lawyers, instead of relying on a mis-matched provider whose mistakes can cost serious money to fix as the company scales.

But the goal of this post is really to emphasize a different, but related point: switching law firms can be a lot more expensive than you think.  Put differently, you might think you’re saving money by going with a “starter” attorney, knowing you’ll just “upgrade” if you’re successful, but make sure you understand the full cost of staging your legal providers in this way. It’s likely substantially higher than you expected. Here’s why.

Diligence Cost – What’s in that “other lawyer’s” contracts?

Startup-focused legal practices, particularly at large firms built to serve startups at all growth stages, will have their own set of contract/agreement templates that they regularly work with.  All of the attorneys at a particular firm will have deep experience working with those templates and know, without having to review them every time, what they do and don’t contain.  So if a new transaction ever comes up and an attorney ever has to make a decision or answer a question that depends on what a historical contract does or doesn’t contain, they won’t have to fully review (and hence you won’t be billed for) having to re-diligence all of the Company’s history.

Naturally, when you switch firms, you bring with you all of the legal foundation that you’ve built on someone else’s contract forms, but are now using attorneys who have no idea what those forms contain.  This means your new attorneys will need to fully review the work you’ve done in the past to be confident that the documents are kosher. On top of the cost of fixing any problems, this review process alone will carry a sizable bill.

Drafting Cost – Making everything fit.

On top of having standardized forms, properly run startup law practices draft their forms to integrate with one another. Defined terms, section references, and contract provisions are in sync between sets.  Formation docs -> Seed Docs -> VC docs -> Acquisition Docs, etc. This integration saves a startup money by allowing an attorney to pick up a set of, for example, venture capital deal forms knowing that it it’s designed from the get-go to sync with the Company’s previously signed contracts.  She can focus on the core deal terms instead of having to tinker with what should be standard language.

Introducing a foreign firm’s contracts into this “legal chain” produces a serious disturbance in “the force.” Everything on a going-forward basis will need to be tailored to fit the foreign legal docs that the Company executed with another firm.  And, unfortunately, that tinkering won’t be pro-bono.

Conflict Risk – Something lost in translation.

It’s also worth mentioning that by requiring your attorneys to engage in all this diligence and custom drafting that they otherwise wouldn’t have needed to do if you’d used them from the beginning, you are automatically taking on the risk that something will be messed up.  A provision in your old contracts might be missed (because your attorneys were working quickly to try to keep the bill low), or the “tailoring” to your old docs might not have been done perfectly (for similar reasons), and a straight conflict within your contracts will arise.  Hopefully it’s a small one. But it might not be. Just know the risk is there.

Think Ahead in Hiring Your Startup Lawyers

So how much can all of these “transition” costs add up to? It depends.  The longer you spend with your “starter” lawyer, the higher it will likely be, but it can easily reach 5-figures.  Keep that in mind when making decisions about how to provide for your startup’s legal needs.  For a successful startup that inevitably has to switch firms, the transition costs of staging, along with those of fixing the mistakes of “starter” lawyers, will likely eclipse what the startup would’ve paid if efficient and scalable legal counsel had been engaged from the beginning.


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