Post Category → Advisors

The problem with chasing whales.

TL;DR: Always trying to work with “the best” people in any category – investors, advisors, accelerators, service providers – can result in your company getting far less attention and value than if you’d worked with people and firms who were more “right sized.”

Background reading:

Founders instinctively think that pursuing the “best” people in any category is always what’s best for their Company. Need VC? Try to get Sequoia or A16Z. Need an advisor? Who advised the founders of Uber and Facebook? Need an accounting or law firm? Who do the top tech companies use?

The problem with this approach is that it confuses “product” value delivery – where what you get is mass produced and therefore uniform – with “service” value delivery – which is heavily influenced by the individual attention you are given by specific people of varying quality within an organization.

If you buy the “best” car, it doesn’t matter whether you’re a billionaire or just comfortable, you paid for it, and you get effectively the same thing. Buying the “best” product gets you the best value.

Don’t chase whales if you’re not a whale.

However, if you hire the “best” accounting firm, that firm will have an “A” team, a “B” team, and possibly even a “C” team within it. That is a fact. Every large service-oriented organization has an understanding of who their best clients are, and allocates their best people and time to those clients, with the “lesser” clients often getting terrible service. To get the “best” service from one of the best service organizations, you need them to view you as one of their best clients; otherwise you’re going to get scraps.

To get real value from a “whale,” you need to be a whale yourself. Chase whales (the absolute best people in their category) without having the necessary weight to get their full attention, and they’ll just drown you. In many areas of business, getting the full attention and motivation of someone who is great, but not olympic medal level, can be far better for your company than trying to chase those who may take your money or your time, but will always treat you as second-class, or a number. I call this hiring “right sized” people. 

Firms matter, but specific people matter more.

I use this reasoning a lot in helping founders work through what VC funds they are talking to. The brand of the firm matters, but you want to know exactly what partners you are going to work with, and you want to talk to companies they specifically have worked on, to understand how much bandwidth you’re going to get. There is a wide range of quality levels between partners of VC firms, and going with someone local who will view you as their A-company and give you the time you need can be much more important than being second or third fiddle at a national marquee firm.

We also use this reasoning in explaining to clients how we see ourselves in the legal services market. We do not work for Uber or Facebook, and we are not even trying to work with the future Ubers or Facebooks, or other IPO-seeking companies of the world. The very high-growth, raise very large rounds in pursuit of an eventual billion-dollar exit via acquisition or IPO approach is suited for certain kinds of law firms and practices designed for those kinds of companies. Most of those firms are in Silicon Valley, because most of those companies are in Silicon Valley.

There was a time when every tech ecosystem looked to Silicon Valley for guidance, and did everything it could to get its attention. Now a lot of people outside of the largest tech ecosystems have come to realize that, in fact, Silicon Valley isn’t really that interested in them; and thats ok. Those SV funds, firms, and people are whales looking for other whales. That is totally fine – the world needs whales, but the rest of the world needs help too.

If you are a unicorn, or legitimately are viewed as on the track to be a unicorn, then working with VCs, advisors, law firms, and other service providers that cater to unicorns will get you great service by ensuring you are working with the top quality individual people within them.

Hire within your class.

However, a recurring trend we’ve seen in many areas, including legal, is companies initially hiring one of the national marquee firms because they wanted the “best,” only to realize that not only were they working with that firm’s B-player or C-player, but even getting responses to e-mails from a specific person was a matter of days and even weeks. By “right sizing” their service providers, they fixed the problem.

In short: be honest with yourself about what you’re building, and then be honest about whom you should build it with. If a $100MM or $200MM, or whatever non-unicorn number, exit would be a true win for you, that is nothing to apologize for. The world needs those kinds of companies; lots of them. But to avoid a nightmare, align yourself with people truly “right sized” for a company on that kind of track.

When hiring any firm in any service industry, ask who exactly your main contact will be, and talk to the clients/portfolio companies of that specific person. Does their client base look a lot like the company you’re building? How responsive are they to you in your initial communications? That can tell you a lot about what level of bandwidth/priority you’re going to get from them.

For the kinds of strategic relationships that really matter, where the quality of advice depends on specific people and the attention they’ll give you, focus on “right sized” people; not just engaging the “best” firms. Don’t get pulled under water by chasing a whale that isn’t really that interested in you.

Vesting Schedules – Beyond the Standard

TL;DR: The standard 4-year with a 1-year cliff vesting schedule is not the only option. Companies can use a number of alternatives to better align incentives, and even select for employees/founders with more loyalty and interest in long-term commitment.

This is not a post explaining what vesting schedules are – I make it a point to (try to) not duplicate content that others have already written about 10x on the web. See this post for a quick run-down.

Most people know that the “market standard” vesting schedule is 4-years with a 1-year cliff. That’s standard for employees, but also quite common for founders. I occasionally hear founders say that a founder team shouldn’t subject each other to a cliff, but generally I think that’s a bad idea. Some kind of cliff is a great way of ensuring that anyone there on Day 1 intends to be there for some meaningful amount of time. If they balk at a cliff, it says something; not entirely clear what it says, but it certainly says something of significance.

Advisors tend to have shorter schedules, like 1-2 years, because their grants are smaller and tenure tends to also be shorter. At least a 3-month cliff is always a good idea for advisors, in my opinion. If they balk, it, again, says something.  Making small, reasonable requests in any kind of relationship, and observing the response carefully, can be a great way to gauge a person’s personality, motivations, and perspective; even if you consider the request itself immaterial and easy to drop. 

However, for companies that feel like the standard approach doesn’t fit their context, or align incentives properly, there are a lot of smart alternatives that we’ve seen our client base adopt. Here are a few:

Milestone Vesting

Instead of vesting based on time, you set it to occur upon certain milestones. These can be any number of things: achieving a certain financing, a certain revenue level, hitting a sales quota, etc. Whenever we see milestone vesting, the milestones tend to be contextualized for the individual. And certainly it only makes sense to have milestones that the individual recipient of the stock actually plays a lead role in achieving.

The benefit of milestone vesting is it can, when it works, better align “earning” equity with actually delivering results, as opposed to simple tenure based on time. However, the challenges that arise are (i) in the drafting – getting people to agree on reasonable milestones, (ii) in deciding when they’ve been achieved – who ultimately decides? the Board? the CEO?, and (iii) when circumstances change and ambiguity arises as to whether the milestone has been met. And of course, it is just more of a hassle to have to track milestones for vesting purposes as opposed to just letting the clock tick.

My strong suggestion to clients whenever they go with milestone vesting is to stick to milestones with objective, unambiguous metrics. Stay away from anything that depends on someone’s opinion – like “doing X to the satisfaction of Y person.” You’re just asking for trouble if you go there. Something like “achieving $X in cumulative customer revenue” will result in far far fewer disputes. And remember to use milestones that the stock recipient plays a significant role in helping the Company achieve. That too will prevent arguments over unfairness or bad faith as to person Y being responsible for why person X didn’t get their vested equity.

Longer Schedules (5-6 years)

There is a lot of value in attracting employees who intend to be with your company for the long-haul, as opposed to those who hop between employers. The sense of long-term thinking and loyalty that a long-term employee can bring to key projects can be hugely important strategically. I’ve always found the “perk wars” of certain tech ecosystems to be somewhat counter-productive, as they tend (in my mind) to select for employees with more mercenary personalities, as opposed to people who want to be there for much more important reasons.

I’ve certainly applied that thinking to how I recruit for MEMN.  Honestly, if whether or not we offer free lunch or doggy sitting will influence your decision to work for us, I’d prefer you not.

Companies that deeply value long-term commitment will often consider having longer-than-standard vesting schedules; maybe 5 or 6 years. Of course, for this to work you generally need to provide an appropriately larger equity stake.  Someone might ask why not, instead of one grant with a longer schedule, simply committing to do another grant after the standard 4-years?

It’s true that you can do that, and the standard approach is to provide ‘fresh’ grants to employees, for retention purposes, once their original vesting schedules run their course. However, (i) a grant made years later will have a higher exercise/purchase price (for tax purposes), so it’s actually tax favorable to do an earlier grant with a larger schedule, and (ii) there’s something about a longer schedule that just signals a person’s long-term commitment better, particularly if coupled with back-weighted vesting (see below).

Back-Weighted Schedules

If you’re looking to use vesting schedules as a way to gauge long-term commitment, back-weighted vesting is definitely an option worth considering. The concept is quite simple. Instead of vesting in equal installments over a schedule, the back-end of the schedule provides more vesting than the front-end. So instead of 25% vesting per year, Year 1 may be only 10%, but Year 4 may be 40%. There is definitely some logic to this idea, because the value someone delivers to their employer tends to go up over time, as they’ve become integrated into the culture, moved up in rank, taken on more responsibility, etc.

A longer-than-standard schedule with back-weighted vesting is one of the strongest messages you can send as to how much significance the Company places on loyalty and long-term employment. And as I mentioned before, if someone really balks at the idea, pay attention to what that tells you, because it definitely tells you something.

For key hires, the standard doesn’t always fit. 

I hear it all the time: “just go with what’s standard.” I understand that approach, and it’s sometimes driven by an attitude that all of this legal mumbo jumbo doesn’t matter. Except for when it does.

For strategic hires, particularly in the very early days of a Company when your core team will totally make or break you, non-standard vesting schedules can be a valuable tool to align incentives, and “filter” for people who may not be as committed to the cause as you think they are. Remember: when someone says “no” to something you think is reasonable, it may not be fully clear why, but it tells you something. And that something can be very important. 

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.