How to Avoid “Captive” Company Counsel

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

Inexperience v. Seasoned 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, and who gets to decide when the pie gets eaten.

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.

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 a “fair” 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 “concern” there.

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?

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 RavikantLawyers 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’ 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.

Protect Your Angel Investors

Background Reading:

A lot of writing, including my own, breaks the world of startup  funding “players” into 2 broad categories: founders and investors. While that is helpful, it’s also important for founders to understand that within the investor category, there’s an important distinction between angel investors and institutional investors; in terms of incentives, behavior, and their overall relationship with the company.

Institutional investors are sophisticated (… usually), repeat players who are working with large amounts of other people’s money; and those other people expect (demand) great returns. They have their own lawyers (and therefore usually negotiate harder), have much deeper pockets, and usually invest much later in the game than true angels; when the company is a much more attractive investment from a risk-adjusted perspective.

Angel Investment: faster, easier, but more exposed. 

Angel investors are investing their own money.  Seed funds / angel groups do work with a broader pool of money, but they are more accurately described as an organized group of angels than a true institutional fund.  Angels often do not utilize their own lawyers in executing deals (because the check sizes don’t justify it), which means they rely more on trust in the team, and on standard, more lenient terms. Their money goes in much earlier in the stage of the company, so at a point where the company is much riskier. Angels are accurately described as betting as much on a founder team as they are on the business.  Prominent angels also regularly serve as “social proof” for gaining the interest of VC funds.

Because angels invest much earlier in a company (than VCs), usually without lawyers, and usually on standard documents with minimal investor protections, their relationship with founders/management is often much more informal and trusting, and less about “the numbers,” than the founder-VC fund relationship. Accelerators usually also fall in the same category. This is all very much a good thing. It’s what allows seed investments to move quickly, at a time where the company doesn’t need or want to spend a lot of hours going back and forth on deal nuances when they could be building the foundation of the business.  But it also means that angel investors are exposed to gaming by later investors (or, sometimes, bad actor founders) who take advantage of key inflection points to push the angels’ investment away from the “deal” they thought they were going to get. 

The broad context in which this happens is fairly simple: an angel round has been closed for a while – usually convertible notes or SAFEs, but sometimes seed equity – and the company is raising a Series A. After negotiation and modeling, the parties have not aligned on numbers. The VC doesn’t like the terms that the angels are ‘getting’ in the round (from their notes/SAFEs), because after accounting for his own share, too much of the cap table is taken.  So he makes his check contingent on the founders going back to their angels and convincing them to accept modified terms.

The angels, not happy about it, are exposed because their money is already sunk, and much worse things could happen if the deal dies. So they cave; accepting worse terms so that, effectively, the new money can get better ones.  Requiring earlier seed money to raise their valuation caps is a common way to make lower Series A valuations more swallowable.

But to be totally honest here, sometimes the gaming is not led by the VCs, but by the founders. They see what the angels are getting in the deal, and might collude with the new money to force a change. I’ve never had one of my personal clients play that sort of game, but I have seen it happen.

There are situations, of course, in which terms simply need to be re-negotiated; usually because the company’s path took a number of unexpected negative turns, and things just won’t work if a reset doesn’t happen. Those situations should be distinguished from the ones in which a deal really can close, but someone is just using the exposure of angels to get more of the pie.

Reputation is capital. Don’t waste it.

The job of company counsel is not to do whatever founders / management want; it’s to advise on what is best for the company and all of its stockholders long-term. On a whole host of issues, people who’ve seen the life cycles of companies play out over time (like VC lawyers) can bring a long-term perspective that a fresh team may not understand intuitively.

My advice to founders, which I put down in Burned Relationships Burn Down Companies, is that relationships matter. A lot. Especially with your early money, which often acts both as your cheerleaders in the market, and as a safety net if things get rough. Putting aside the purely ethical aspects of gaming angel investors (which are important, mind you), burning your early investors is bad for the company.  It’s also just bad for founders personally, whose relationships can mean a soft landing if their company fails, or support for their next venture. 

As a startup and new team, you don’t have buckets of money, or a rock-solid reputation, to insulate you from everything that can go wrong with a company. Your reputation and social capital are some of your most valuable assets; don’t waste them. If anyone is asking you to hurt your social capital, stand your ground. They’re asking you to incur a cost, but for their benefit.

In fact, real chess players sometimes want to burn your other relationships, because it reduces your optionality, which increases their leverage. Always think multiple steps ahead.

Pro-rata rights are core economics.

And on a final note, it’s important for founders to understand that when angel/seed funds request “pro rata rights” for future rounds, those rights are not a nice-to-have that is independent from the economics of their existing investment. Successful angel investment depends on the ability to double down on winners (put in additional investment), because the vast majority of an angel’s investments are losers. That’s the core economics of angel investment. If you deny angels their pro-rata in a Series A, you are taking away a part of their deal that allowed them to invest in you in the first place. The long-term consequences for a company and a founder team are usually not worth the near-term benefit.

Promising Equity v. Issuing Equity

Background Reading:

An underlying theme of a number of SHL posts has been the common misunderstanding among young, first-time founders around what startup/vc lawyers in fact do. As I wrote in Legal Technical Debt, a mindset has emerged from certain startup circles suggesting that virtually anything legal that startups do at early-stage, from forming their company to raising seed financing, can be automated with software.

That confused mindset leads founders to (i) assume that all lawyers are just luddites over-charging startups for effectively filling in forms, and (ii) results in founders accruing an enormous amount of compounding ‘legal technical debt’ from badly drafted documents, mis-matched contracts, missed legal steps, etc. For companies that fail fast, the debt never comes due. And yes, there is a clear correlation, from my experience, between founders who arrogantly think lawyers are worthless and those that never build anything of significance.  Dumb people believe and do dumb things.

For those founders that do end up building a real business, however, the 10x cleanup cost of legal technical debt (relative to what it would’ve cost to do it correctly from the start) is often brutally painful. There are a lot of very interesting new tools out there being built to streamline and optimize how tech/vc lawyers work, and you should certainly look for lawyers who are using them. But if you think for a second that you’re going to build a real tech company without needing serious lawyers who can safely manage significant legal complexity, you are, without question, deluding yourself.  

A significant source of “automation confusion” arises from founders not understanding the difference between promising equity and actually issuing equity. I’ve noticed this from how many of our own (very early stage) clients will randomly e-mail us a set of contracts executed over a period of several months with a short message like: “we went ahead and *issued* some equity on our own.  just FYI.”  This blog post will save me from having to write the same e-mail 30 times in the future.

Promising Equity 

I can promise someone equity in 5 seconds, and 1 sentence.

“I promise to issue you 10,000 shares.”

See, it’s not hard. Promising equity is exactly as easy, and as automatable, as it sounds.  Anyone who automates a contract for promising equity, which usually means filling in numbers into a static template, doesn’t deserve the slightest bit of praise for innovation. It’s been do-able for decades.

Sure, people still make mistakes in promising equity all the time. They calculate the number of shares incorrectly, or they get the vesting schedule wrong (or don’t offer one at all), or they simply grabbed the wrong form to begin with.  But the point is that, perhaps with a little guidance from educational materials and a boilerplate form, promising someone equity is do-able as a DIY project.

Reality Check

The problem, of course, is that promising equity is 2% of the much more complicated process needed to actually issue equity. To correctly accomplish the issuance of equity from your company and into the hands of the intended recipient, a web of highly contextual legal analysis needs to occur. Just a short (non-exhaustive) example:

  • What kind of entity are you? That influences the type of equity you can issue.
  • Stock? Option?
    • If Stock, at what price?
    • If Option, at what price? To an employee, or a contractor?
  • Vesting schedule? 83(b)? Acceleration?
  • Was the price set correctly to avoid tax consequences?
  • Enough authorized shares?
  • Correct class of equity?
  • Is it being issued under an equity plan?
  • Was the plan adopted correctly?
  • Are there enough shares in the plan?
  • Is the recipient eligible to receive the equity under securities laws and tax rules?
  • Any state-specific rules/filings to comply with?
  • Any contractual approvals needed?
  • Any cap table adjustments needed, like anti-dilution?
  • Approved by Board?
  • Anyone else that needs to be notified about the Board action?
  • Any spouses we need to worry about for community property purposes?

I could go on, but you get the idea.

Want to try automating that? Good luck to you. Medical care will be fully automated before complex legal work is. Why? Because there’s far less variability in biology than there is between the legal structures of companies. You simply cannot automate (not in a commercially viable way, at least) in an environment where every use case has a totally different starting point, context, and history, in an infinite number of combinations. Even less so where high-stakes errors are cemented in ways (via contract execution and enforceability) that do not allow for quick and easy bug fixes. That is precisely the world in which serious VC lawyers operate.

Believe me, I empathize deeply with the disdain for lawyers held by many entrepreneurs, and share some of it myself. As someone who manages recruiting for our firm, I constantly find myself fighting a sense that the legal field is a magnet for people who think that perfecting their punctuation matters more than learning to actually advise clients on the what, why, and how of startup law.

But there are lawyers in the market who know how to get things done efficiently and correctly. I hire those lawyers. You can either (i) pay them now, (ii) pay them 10x later, or (iii) assume your company will fail before the debt comes due.

Startup Advisors: Best Practices

Background Reading:

Advisors. The best startups have great ones. They save you lots of headaches, time, and money. In fact, I’m not sure I’ve come across any successful client that didn’t have a strong set of advisors. Here’s some advice on how to not screw it up:

Advisory ‘Boards’ Rarely Exist.

A set of advisors is sometimes referred to as an advisory ‘board,’ but 99% of the time that’s just a term to make it sound cool. The advisory ‘board’ never meets as a group, and often doesn’t even know each other. They’re just a loose set of advisors that a company works with 1:1, or occasionally in smaller groups. Nothing like a Board of Directors, which actually does have to coordinate schedules.

Don’t Stay Local.

As the first linked post above explains in depth, 20 minutes on the phone with someone who has the right expertise is 1000x more valuable than days spent with someone who is more accessible, but can’t provide real insight that isn’t available already via blog posts or books. This means that if you’re relying solely on the very limited pool of people available via your local business ecosystem, you’re doing it wrong.

LinkedIn, Twitter, Angellist, E-mail, Phone. Work ’em. Connect with the key people in your local ecosystem who can make things happen, but don’t fish only in your little pond.

Don’t Confuse Mentors with Advisors.

Mentors can be really valuable to new founders. They can provide emotional support, friendship, coaching, and all kinds of other things. But are those the kinds of things that deserve an equity grant?

It’s ultimately the team’s call. But just realize that those are not the kinds of things that real advisors are meant for. Advisors provide real strategic insight, connections, recruiting, investor introductions, things that go beyond moral support for the founders and actually move the ball forward for the company in an obvious way. That’s the kind of value-add that typically merits equity.

Get Independent Viewpoints

For high-stakes, complex questions for which the answer isn’t clear, advice needs to be triangulated. You don’t treat any particular person’s perspective as gospel; instead you speak with multiple people and combine all of their viewpoints to make your judgment call.

That sort of triangulation is not possible when all of your advisors have the same background, are part of the same circles, etc. Especially when the questions involve big decisions for which various stakeholders have incentives to favor one option over another, you want advisors who are detached from those incentives, so their advice is objective. This, btw, is also the case with lawyers.

Favor Intellectual Honesty over Politeness

The whole point of getting outside advice is to help you see things you can’t see on your own. If your strategy for choosing advisors is to work only with the people who are agreeable to your own opinions, you’re wasting your time. People who are blunt with their advice, but deliver real insight when they give it, can be game changers for a company. 

Use an Advisor Agreement.

It’s not magical; templates abound. The Founder Institute’s FAST Agreement is perfectly acceptable, and even simplifies equity calculations. The most important thing is that an Advisor Agreement removes any ambiguity as to (i) compensation owed for advisory services, (ii) who owns the contributions, IP, etc. that result from the advisory (the company), and (iii) confidentiality of any info shared. Yes, any vc lawyer has seen founders get in trouble with these issues for not taking the time to document it properly.

Equity; %, Vesting Schedule, Cliff, Acceleration.

If an advisor expects cash from an early-stage startup, that’s usually a red flag, short of a really unusual circumstance.

The FAST Agreement has pretty solid guidelines for what’s appropriate in terms of equity %, depending on the Company stage. Pre-equity round, 0.25%-0.5% is a typical advisor. 1% is someone extremely strategic whose name you absolutely want behind your company. After an equity round, the %s naturally shift down a bit because the company is more valuable.

1 or 2-year vesting schedule and a 3-month cliff, and full single-trigger acceleration on a change of control.  Advisors get full acceleration because acquirers never expect them to stick around after a sale, unlike founders or executives.

Use that cliff.

We regularly see founders engage an advisor expecting tons of value to be provided, and then crickets once the equity is granted. But the founders don’t do anything about it. 3-months should be more than enough time to know whether a new advisor will really deliver the goods, and if not cut the cord and get that equity back for re-use.

 The hard part, of course, is finding the right advisors and selling them on your vision, so they’ll give you the time. If no one on your team knows how to hustle and sell, either start learning yesterday, find someone who can, or (honestly) just give up now. Selling, in a dozen different ways (including to advisors), is 75% of what a competent founder CEO does.

When You’re Not CEO Material

TL;DR: Before you even talk to VCs, know your own strengths and weaknesses as a leader, and work on them. Know your VCs by asking honest questions early on, and verifying answers in the market. And be proactive and honest about what you really want to be doing at your company, and what matters most to you. When CEO succession drama starts to damage a company, it’s almost always because the founder and the VCs failed to (i) align themselves on their approach to Company management and recruiting early on, and (ii) create an environment of trust and transparency where founders can give up some control without fearing that the fruits of their hard work are being given up as well.

Background Reading:

No matter how much certain investors market themselves as “founder friendly,” no competent VC can guarantee a Founder CEO that they will stay CEO. VCs have a job to do: to turn other people’s money into more money. To the extent they are convinced that keeping a founder as CEO will maximize their chances of doing that (long-term), they will do so. Otherwise, they will tell a founder CEO, sooner or later, that a new CEO is needed.

“Founder Friendly” VCs are the ones who’ve concluded that being friendly to founders helps them make more money.  They are not your BFFs, and you shouldn’t need them to be.

The below are some thoughts, from someone who’s seen it play out many times, on how founders should approach the “Are you CEO material?” issue; both before the hard conversation has arrived, and after.

First: Answer Your Founder’s Dilemma: Rich or King?

If staying in control of your company is much more important to you than achieving an excellent financial return, you should significantly reconsider whether venture capital is right for you at all.  Remember: VCs have a job to do, which is to make lots of money. You bring them on to align yourself with them so that when they make lots of money, you make lots of money.

It’s fine and common if you have a certain ‘mission’ that runs alongside the goal of building successful, profitable business; most great founders do.  But if you’re working with VCs, (i) that mission better be the kind of mission that unlocks lots of benjamins, and (ii) you better be OK at some point handing over the crown and becoming a part of, but not the leader of, management. Because, statistically, most founder CEOs eventually get replaced; voluntarily or involuntarily.

Second: Find Out if a VC is a Coach or Underminer

While all VCs are in it to make money, their philosophies regarding how much “coaching” to give founder CEOs vary wildly. Some VCs know that a founder CEO most likely will need to be replaced once the company has become a true enterprise, but they see value in keeping a founder in the CEO seat for some time and coaching them on their gaps, and also helping them fill some those gaps with other senior hires.  Other VCs virtually never let a first-time founder CEO remain in their position post-Series A. They are fine having them as CTO or COO, but they will almost always make their large check contingent on bringing in one of their preferred professionals.

There is no way to know whether you are working with a Coach or an Underminer other than to (i) directly ask (early) the VC what their perspective is on senior management post-closing, and (ii) examine the existing portfolio of the VC to see what has in fact happened every time they’ve closed a round. Trustworthy advisors who are active in the market are helpful here, as is LinkedIn.

If you’re working with an Underminer, and there are no other options, it is what it is. Work within that reality (see Step 4).

Third: Realize that you are being “sized up” from the moment you first speak to investors.

No one should pretend that “good CEOs” fit neatly into some contrived stereotype. Their personalities, appearance, backgrounds, etc. can vary significantly. However, the core jobs of a CEO, particularly at early stage, are quite uniform: (i) recruit employees, (ii) recruit investors and strategic partners, & (iii) manage and lead everyone to execute effectively on the strategy. From the moment you first interact with investors, they are asking themselves whether a founder CEO can do those things.

Fact: everything about your interactions with lead investors, from the tone and confidence of your communications, to body language and eye contact, and how you respond to push-back and calculated aggression, will influence their perception of whether you are “CEO material.” Complain all you want about prejudices, bias, judging books from covers, etc., but that is just reality. Leadership is not handed charitably. It’s asserted by behavior and results. The concept of “executive presence” is something worth familiarizing yourself with.

No, this does not mean you need to pretend to be some gun-slinging, type A alpha executive. Many great CEOs are calm and collected. But the fact of the matter is that being a CEO of any company requires the ability to have hard conversations and take some heat. If you can’t hold your own in a direct conversation with a VC, they will infer that you can’t do so in the many other key conversations that a CEO needs to have to lead a company.

I’ve lost track of how many times I’ve heard something like “That founder? He’s got a bit of an ego,” to which I usually respond, “What do you think it takes?” Ego? Thick skin? Stubborn? Chip on their shoulder? A little prickly? You better f***ing believe it.  Industries usually don’t get blasted open by people overflowing with tenderness and sensitivity.

Fourth: Focus long-term on transparency and influence; not control.

I’ve found over time that many founder CEOs do not actually enjoy being CEO, especially as the company starts growing significantly (~post Series B). They insist on staying in the CEO seat, not because they truly think it best suits their skillset, but because of a fear that stepping down from the top automatically means totally losing influence and visibility into where the company is headed. A culture of transparency and clear communication at the board level can resolve this disconnect and avoid dysfunction.

The key issue here is not whether the Company needs a new CEO, but how to handle succession. The perfect way to create mistrust between founders and their board/management is for VCs to parachute in C-level hires with minimal founder involvement in the recruitment and selection process. It looks something like “We are getting a new CEO, and it’s X (often who was a CEO at a prior portfolio company).” In this scenario, the recruitment of new executives feels far less like the leveraging of much-needed, independent new talent for the benefit of everyone, and more like the investors taking control over management by hiring their loyalists under the pretense of ‘upgrading’ the team. 

When a founder CEO is able to propose her own candidates for the CEO position (and other C-level positions), and play a lead role in interviewing, vetting, and training the prospects, succession goes substantially smoother for everyone. In that scenario, much like a truly independent director, the founders will view the new CEO and other C-level hires as balanced people whose long-term vision and values are closely aligned with the original team. Trust is preserved, and that trust, along with a continued seat at the Board table and contractual protections around their equity and compensation, frees founders to move to positions in the company that are better suited for their skills (CTO, Chief of Product, Chief of Strategy, COO, etc. etc.), and which they usually enjoy more.

Again, different VCs have different philosophies on how to approach CEO/Executive succession, including timing. The only way to find out is to get a dialogue going early on, before term sheets are delivered, and verify the answers by talking, privately, to portfolio companies. As always, having your inner circle of advisors to, confidentially and off-the-record, help you gather that information is key.