TL;DR: Given the often substantial imbalance of experience between first-time entrepreneurs and the investors/VCs they are negotiating with, experienced startup/VC lawyers are often the most important “equalizer” at the negotiation table; both on deals and on high-stakes board-level issues. Smart repeat players know this, and therefore often directly or indirectly push startups to hire lawyers (as company counsel) that they can control. Those “captive” lawyers are, due to their conflict of interest and dependence on institutional investors, incapable of representing the company and common stock objectively; and early common stockholders (including founders) often get hurt as a result. The market needs to stop tolerating this unacceptable mechanism of control.
Background Reading: Why Founders Don’t Trust Startup Lawyers
This post is going to make some people uncomfortable. People who work with me know that I’m not the type who likes to irritate others just for the fun of it. But I’m always willing to say something that needs to be said, and I’ve always structured my business relationships and life in a way that I’m not prevented from saying it.
“It is difficult to get a man to understand something when his salary depends on his not understanding it.” -Upton Sinclair
“One Shot” Inexperience v. Seasoned “Repeat” Veterans
Founders, particularly inexperienced first-time founders, face enormous uncertainty and opacity as they build their companies. In that environment, they’re tasked with making complex long-term decisions, on behalf of themselves and other stakeholders, with very high-stakes implications; including distributional implications as to who gets what share of the limited pie.
More so, as founders raise capital, they engage with highly experienced, sophisticated, repeat player parties who have gone through the same process dozens of times. Those parties (investors) are typically aligned with founders/management in the sense that they want the company to be a success, but there is significant misalignment in the fact that each side wants their share of the pie to be larger than the other, and each side often disagrees on when it’s time to start eating. In the case of institutional investors, they have a legal obligation (to their own investors) to get as high of a return for their investment as possible; in other words, to get as much of the pie for themselves (and as large of a pie) as they can.
Repeat players (institutional investors) are highly experienced, wealthy, diversified, and have downside protection. “One shot” players (founders, early employees) have their net worth highly concentrated in one company, without downside protection; and they’re often highly inexperienced. The misalignment is obvious, and never goes away.
Counsel should level the playing field.
In this environment: inexperienced founders/management working with highly seasoned third-parties with significant misaligned financial motivations, founders/management have to rely on trusted advisors to level the playing field; to ensure that their inexperience is not leveraged unfairly to their detriment.
Without question, one of, if not “the” core advisor that startups turn to for leveling the playing field in interacting with highly seasoned investors, particularly at early stage, is Company Counsel; the lawyers hired to represent the company. Startup lawyers have a front-row seat to deals/activities in the market that cover a much broader, and larger, area than any particular investor sees, and they leverage that expertise to help startup teams navigate what, to them, is brand new territory.
Company counsel’s job is not to represent the founders personally – see A Startup Lawyer is Not a Founder’s Lawyer – nor the investors, but the entire company, including all of its stockholders as a whole. The best analogue I can think of is a family therapist, who doesn’t represent the parents or the children, but is looking for the well-being of the family unit. If someone is threatening the well-being of the family (the company), or trying to unfairly dominate it in a counter-productive way, the therapist (company counsel) helps address it. Sidenote: my job really does resemble that of a therapist sometimes.
The best company lawyers combine a “win-win” attitude (grow the pie) with a long-sighted, subtle skepticism over each individual actor’s motivations; monitoring how actions could result in unfairly taking one person’s part of the pie and handing it to someone else.
Many startup lawyers are “captive” to institutional investors.
So the founders-investor relationship is inherently imbalanced in favor of the seasoned, experienced investors at the table, and company counsel is supposed to play a strong role in correcting the imbalance. Clearly then, any factors that raise doubts as to the independence of company counsel; factors that might make him/her ‘captive’ to the interests of the money at the table, are cause for serious concern.
In “Why Founders Don’t Trust Startup Lawyers” I described how the business development practices of certain startup/vc lawyers give companies every reason to be worried that their company counsel is inherently incapable of providing that ‘balance’ that they are supposed to rely on. Many lawyers know that if they can win a relationship with a VC fund, that relationship can be worth dozens of deals/clients to them in a manner of just a few years; far far more efficient biz dev than going after companies one by one. So building economic ties with those VCs becomes a major source of business for lawyers, including lawyers who act as company counsel.
I don’t waste any breathe or time trying to actually convince anyone that this scenario is a serious conflict of interest problem; certainly not lawyers. See the Upton Sinclair quote above. I simply explain to founders/management in very clear terms how things in fact work, and let smart people arrive at their own conclusions. Sunshine is a great disinfectant.
Chess: Losing the negotiation before it starts.
In my school days before becoming a lawyer, I found negotiation strategy and psychology to be a fascinating area to study. Winning a negotiation and getting what you want in a deal is, to those who are observant, an intricate game of human behavioral chess. To get what I want, I could simply negotiate very aggressively at the negotiation table. That can work. But there’s a cost to it. It spends social capital that I’d prefer to keep. I come off as overly self-interested, when as a long-term player I’d prefer to be seen as a friendly, trustworthy guy; in line my PR/marketing efforts.
A much more effective strategy is to win by preventing the negotiation altogether. A simple checkers player wins by brute force negotiation. But a ‘chess player’ in business wins by controlling the environment of the negotiation, and the people involved, and in many cases preventing negotiation entirely. Ensure companies are using my preferred lawyers, swell guys that they are, and who I know won’t step out of line with the financial ties I have on them. Then deliver an (air quotes) “standard” term sheet. The founders then take that term sheet to those lawyers, maybe there’s a little back-and-forth for good measure, and we move forward, with ‘our guys’ on the inside long-term.
By convincing founders/management to use captive company counsel, investors can get what they want – both in a financing and long-term – without even having to negotiate much for it. When requesting certain terms, making certain decisions, or engaging in certain behaviors, independent company counsel will properly advise the team on how to respond or defend themselves; but captive counsel will just say it’s all normal and standard, lest he anger the people really funding his salary.
I know some people will try to stop me right there. I’m being overly cynical here, they’d say. This is just how the business works. Surely no serious investor would actually use their influence over company counsel to push things unfairly in their favor.
Oh really? Many VC lawyers, including myself personally, have observed situations in which a negotiation is not going in the direction an investor would like, and off-the-record phone calls to company counsel get made. “We’re hoping to preserve our long-term relationship here, beyond just one deal.” “Our fund is actively seeking firms to partner with long-term.” “If this deal goes *as hoped*, we’d love to explore other opportunities to work together.” To a lawyer who plays both sides of the table, you are one deal, while a VC fund’s “favor” can mean many, many deals. Don’t delude yourself into thinking that favor is free.
I am happy to have a discussion about the issues I bring up here, and to be clear, there are many well-respected investors who respect the appropriate boundaries. But please don’t try to feed me or companies candy-coated bullshit about the angelic “professionalism” of business parties when 7, 8, 9 figures are on the line, and a few easy phone calls and veiled threats (or bribes) can ensure they stay in the ‘right place.’ If your investors would never make those phone calls, then there shouldn’t be a problem with selecting company counsel with which they can’t make those phone calls.
Cost control as sleight-of-hand.
Notice the subtleness in how certain investors (including some blogs) talk about lawyers and legal fees. Why can’t we just close a deal for a few thousand dollars? This stuff has become so standard, let’s just keep the negotiations “between the business parties” and close this thing quickly.
Yes, let’s move fast (read: not discuss the terms much) and keep it “between the business parties”; where one side is inexperienced and doing it for the first time, and the other side has done it 50 times. That’ll keep it “fair.”
We’re negotiating and discussing transactions where even small changes could mean millions of dollars in one pocket or another, but let’s “control the legal fees” to save $10-20K right now. Yeah, gotta watch the legal budget. Really appreciate your (air quotes) “concern” there, champ.
If you are building a company on a trajectory to be worth at least a comfortably 8 or 9-figure exit (which if you are talking to serious tech investors, you are), the idea that you should minimize time spent working with counsel, because it’s all just boilerplate and you’re better off keeping the legal fees for something more valuable, is a mirage set up to keep teams ignorant of what they’re getting into, and how they can properly navigate it. Telling a company “don’t ask your lawyers about this” sounds suspicious. “Let’s save some legal fees” sounds much better. But there’s no difference. You are being played.
Balanced, but also competent.
Stepping back a bit, it’s important to also clarify what I am not saying in this post. I am not saying that investors and other stakeholders in a company should not have an interest in ensuring that company counsel is competent and trustworthy. Founders do occasionally engage lawyers, typically for affordability reasons, that simply do not understand the market norms of venture capital financing. Using those types of lawyers ends up being a disaster, because they will slow down deals and offer all kinds of comments that aren’t about ensuring fairness and balance, but are simply the result of their not knowing how these types of deals get done. That will drive the legal bill through the roof, with little benefit.
Company counsel should have strong experience in venture capital deals. Sometimes when investors request a change in company counsel, they have valid concerns about that counsel’s competence. Assess the merits of those concerns. However, it is one thing for your investors to say “this lawyer won’t work,” and then leave it to the company to find new, independent counsel. It is a completely different, and far more questionable, thing for them to insist that you use their preferred lawyer.
Avoiding captive counsel.
Here are a few simple questions to ask a set of lawyers to ensure they can be relied upon as company counsel to fairly represent a VC-backed company, particularly one with inexperienced founders:
- What venture funds / investor funds do you personally (the lawyer you’re directly working with) represent as investor counsel, and how many deals have you done in the past 3 years for them?
- What about your law firm generally? (for very large firms, this is less important)
- How many of your firm’s clients are portfolio companies of X fund, and how did you become connected to those companies? May I reach out to the companies to confirm?
- Can I get your commitment to not pursue investor-side work for X fund while you are our company counsel?
- Are there any other financial ties to VC funds that would potentially compromise your ability to represent and advise us fully in negotiating with those VCs?
Larger ecosystems and larger law firms are generally less prone to this problem, because it is harder for individual players to really throw their weight around as a percentage of a larger firm’s revenue. That is to say, if the lawyer you’re working with doesn’t personally represent/rely upon X fund, but some other lawyer in the large law firm does, it’s less likely those “phone calls” could be effectively made. Although even in Silicon Valley and NYC BigLaw I’ve seen situations in which a fund will ‘nudge’ a set of founders to their preferred partner at a large firm. 100% captive.
In smaller firms, which are significantly more exposed to this problem due to their size, you’ll sometimes find that a single fund accounts for a massive percentage of that firm’s pipeline revenue. Those lawyers will slap their mothers if the fund asks them to, and companies are wise to avoid using them as company counsel.
The costs to companies of having captive counsel can be severe. Rushed, unfair sales because a particular fund’s LPs suddenly decided they need liquidity. Refusals to pursue other potential investors because the ‘right’ term sheet from ‘friendly’ investors has been delivered. Executive changes installing ‘friendly’ new management without an objective recruiting or vetting process. Early firing of founders without reasonable opportunities for coaching. The list goes on.
This is not theoretical. When company counsel is captive, their passivity will allow the preferences of a portion of the cap table to dictate the trajectory of the entire company, without the checks and balances that a properly governed company should have. And yet the sad fact is that inexperienced founders often don’t even have the frame of reference to know it is happening, or that it wasn’t supposed to happen that way. Many just assume, wrongly, that “this is how these things work,” when really that’s only how it works when you hire advisors who can’t, no matter how much they protest basic facts of human behavior, be objective.
“Don’t just go with the lawyer that the VCs insist upon. These lawyers will work with the VC on a hundred financings and with you on only one. Where do you think their loyalties lie? Get your own lawyer, and don’t budge.” – Naval Ravikant, Lawyers or Insurance Salesman?
This issue is not about labeling one group of market players as ‘good’ and the other as ‘bad.’ Hardly. There are many, many investors in the market who are phenomenal people with deep ethics. They should have nothing to worry about in ensuring their portfolio companies hire competent, independent counsel. And the best companies always maintain transparent, friendly relationships with their investors.
This is about acknowledging that no one in any tech ecosystem ever has more skin in the game, financially and emotionally, than first-time entrepreneurs; not even close. And yet at the same time, their inexperience means that their closest advisors play an outsized role in helping them navigate the various relationships and risks that they are exposed to. Pushing startups to use their investors’ preferred lawyers as company counsel is, plainly, an unjustifiable mechanism of control; one that anyone who supports entrepreneurship and tech “ecosystems” should not tolerate.
People with far more experience and power than tech entrepreneurs will demand that their company counsel be independent and objective, because the fairest outcomes result when everyone at the table is well-advised. Ignore all attempts to argue the contrary. Founders should demand the exact same for their companies.