Post Category → Board of Directors

Rich v. King: The (Core) Founder’s Dilemma

TL;DR Nutshell: Much of the tension between founders and outside investors lies with one question, highlighted (years ago) by Noam Wasserman (HBS) as the core “founder dilemma”: do you want to be rich, or do you want to be king? When both founders and investors are honest with each other (and themselves) about their feelings about, and approach to, this dilemma, their relationship ends up running far more smoothly.

Background Reading:

Rich or King

In the majority of circumstances (statistically) the wealth accrued by entrepreneurs is inversely correlated with their percentage ownership stake in companies. In other words, founders who give away more equity and control in their companies (to other employees, investors, etc.) end up, on average, building larger, more valuable companies, and therefore become much richer than founders unwilling to give up control. That inverse relationship is the foundation of what Noam Wasserman, a professor at Harvard Business School, calls the “Founder’s Dilemma.”

Obviously, when any particular company (in isolation) is extremely successful, founders are able to maintain more control and ownership relative to companies that are less successful. We all know stories about the (rare) Facebooks of the world in which founders have maintained significant control through many rounds of funding and even IPO.  But overall the types (categories) of businesses in which entrepreneurs give up control in order to attract capital, talent, and other resources will grow much much larger (and enrich the founders) relative to the types of companies in which entrepreneurs maintain a tighter grip.

This is why Mr. Wasserman says that if founders want to avoid significant headache and heartache in the course of building their business, one of the first questions they need to ask themselves, and be honest about, is: do you want to be rich, or do you want to be king? Because very very very rarely can you be both.

Some founders legitimately care less about money than about ensuring that their business stays in alignment with their long-term vision/mission. They certainly want to be successful, but a removal from the leadership position in their company would, in their mind, mean personal failure, no matter how much gold they can expect to line their pockets with.

Other founders want to retain control/influence in their company as long as they feel that doing so will increase their chances of becoming financially successful, but the true, primary end-goal is financial success, and they will willingly step down if they feel someone else can scale the company better and faster.

Kings and VCs Don’t Mix

If you are very heavily a “King” founder, you need to think very very carefully about whether you should take institutional venture capital at all. VCs fall along a spectrum in terms of how much deference/respect they give to founder CEOs. Some (the good ones) will assume a coaching perspective, respecting a founder CEO as the head of the company and pushing her/him to learn and become a great leader. Others (the bad ones) will move as fast as they can to undermine founders and fill management with their handpicked roster of outsiders. The best way to find out who the Coaches and Underminers are is to ask people (privately and off-the-record) who’ve worked with them, particularly other founder CEOs.

However, while the best VCs give founders real opportunities to learn and excel, every-single-one will replace a founder if/when it becomes clear that doing so is required to continue scaling the business. Why? Because VCs are profit-obsessed vultures? No, because they have bosses who hired them to make them money, by achieving big exits. It’s their job.  So even if you have the best, most respectful set of VCs on the planet, the clock is ticking once that money hits the bank. If you can’t handle the thought of not being CEO of your company, no matter how large it gets, don’t take VC money. Ever.

The Jungle, The Dirt Road, and The Highway

What many first-time founders don’t realize, though, is that as many startups scale and become large enterprises, there often comes a time when a founder CEO wants to be replaced. Jeff Bussgang’s three stages of companies: the jungle (earliest stages), the dirt road (early scaling), and the highway (mature company/late-stage growth) help explain why.

To be a successful founder, you usually need a personality that thrives in, or at least is highly capable of handling, chaos (the jungle). Meetings, committees, structure, process, reporting obligations, policies, policies on meetings, meetings on policies, etc. are often the exact kinds of things that founders are avoiding by starting up their own companies instead of taking jobs at BigCo. They thrive in following their intuition/judgments, tackling tough problems, and being on the ground strategizing about product and selling the Company’s vision.

But as companies become full-scale enterprises with hundreds of employees, all of that “structure” becomes necessary. You simply cannot run a 500 employee multi-national company like a Series A startup. Great founders often succeed in the jungle, and thrive on the dirt road (when the company is a startup), but start feeling suffocated, uninspired, and disengaged on the highway. And of course, professional CEOs are the reverse: they are trained to keep the rocketship steady and fueled once its cleared the roughest atmosphere, but their skillset breaks down if required to operate in the iterative, intuitive, grassroots environment of early-stage companies.

“Rich” founders who understand their strengths, and when those strengths are no longer optimal for the stage of their company, are able to actively participate in the executive succession planning of their companies, rather than putting up a fight with their Board.  Some decide to completely step away from the company they’ve built in order to go build something new. Others will take a role in their company that leverages their strengths – removed from the day-to-day processes and bureaucracy of the enterprise, and focused exclusively (as an example) on higher-level product and strategy.  Some founders will (happily) make the transition between jungle, dirt road, and highway without giving up the CEO title, but those are few and far between.

The important thing in all circumstances is that founders not fight the reality of what it means to take on institutional capital and build a large, scaled company. Work within that reality to achieve financial and personal success. Know yourself. 

Start Off With Transparency of Values and Vision

Control-freak founders are not alone to blame for the ‘founder’s dilemma’ dysfunctions of the VC-founder relationship. Certain VCs fail to be upfront with founders about their expectations and style of corporate governance. In order to “get the deal,” they’ll talk up how supportive and founder friendly they are, and once the cash is deposited immediately start running through the playbook described in How Founders Lose Control of Their Companies.  A founder who wants to be King and a VC who pretends (temporarily) to be OK with that is a perfect recipe for dysfunction at the Board level, which usually ends up destroying value.

As trite as it sounds, honesty and transparency go a very long way here. Founders should be open about their vision for the Company, their expectations for how they’ll interact with their Board, and their attitude towards when and how to recruit outside management.  VCs shouldn’t beat around the bush about what the job of a venture capitalist is, and their approach to Board governance and executive recruitment.

The narrative of the founder CEO pushed out by VCs he now hates isn’t the only narrative out there. There are plenty of success stories of founders who built strong, trusting relationships with investors who still did their jobs as VCs and ensured professional management (that the founders can trust) was brought in at the right time. It just depends on the people.  Building and maintaining trust is hard. But so is building and scaling a company. Cut the BS, communicate like adults, and then focus on building something awesome and getting rich, together. 

The Fiduciary Duties of Founders

TL;DR Nutshell: The moment someone is added to a startup’s cap table, founders (as majority stockholders, directors, and officers) becomes fiduciaries of that stockholder. This means that, regardless of how much control founders may have over a company, corporate governance law draws a hard line on how that control can be used. Crossing that line can result in a lawsuit.

This is one of those “core concepts” posts that, to lawyers and professional investors, will seem laughably basic; and yet the topic is something that I regularly see first-time founders get very wrong. And like most SHL posts, I’m going to explain things without referencing statutes or complicated terms. Founders need to understand the concept of Fiduciary Duties. The details they can learn from their lawyers or on-the-job.

State Corporate Law

Most Angel/VC-backed startups are Delaware corps. If they are not Delaware corps, they are usually incorporated in their home state and will be required by institutional investors to become Delaware corps if/when they ever are offered a check.  Whether you are a Delaware corp or not, your state certainly has corporate governance rules giving founders (as directors and majority stockholders) varying degrees of fiduciary responsibility to minority holders in their company. The concept is the same.

At the most fundamental level, to say that founders have fiduciary duties to their stockholders means that they cannot, without seriously risking a lawsuit, unfairly enrich themselves at the expense of other people on their cap table. They can certainly get rich by making everyone on the cap table rich; by growing the pie. But they can’t, without some kind of very credible case that it is necessary for the well-being of the entire business, improve their part of the pie at the expense of the rest of it. 

Hypothetical: Founders X and Y hired Employee A and gave her 5% of the Company that, because of some big contributions she made, was 40% fully vested on the date of issuance (meaning 2% of the Company’s equity, of her holdings, is fully vested). After a few months after the issuance, they have a big dispute and the founders fire Employee A, which they are certainly entitled to do. Under the Stock Issuance Agreement terms, 3% worth of the Company gets returned (because it wasn’t vested yet), and Employee A walks away with the 2% she had vested.

But Founders X and Y are pissed off that Employee A has that 2%. “She doesn’t deserve it. She totally ruined the product” they say. Then the light bulb switches on. “We control the Board and the stockholder vote! We’ll just dilute the hell out of her by issuing ourselves more shares!” they say.

Sorry, dudes. If it was that easy to screw minority stockholders, no one would ever invest in a company.

Delaware and other states have rules around “Interested Party Transactions.”  Without getting in the weeds, Interested Party rules boil down to:

  • A Board of Directors has a duty (a fiduciary duty) to do what’s best for the company and all of its stockholders taken as a whole, without unfairly enriching its own members.
  • Any transaction in which the Board members themselves are specific beneficiaries – meaning they are getting something that others are not – is inherently suspect. It is an “Interested Party Transaction” and is open to claims by minority stockholders (the people who didn’t benefit from the transaction) that it was a fiduciary duty violation.
  • In order to “cleanse” (so-to-speak) the transaction and, in some cases, give it a safe harbor protection from lawsuits, extra steps must be followed to ensure the transaction really was fair. Those steps usually are (i) obtaining approval by the disinterested members of the Board (if any) and/or (ii) obtaining approval by the disinterested stockholders of the company. The disinterested people are the ones who aren’t getting the special benefits.

Put the above 3 bullets together, and it’s clear that Founders X and Y (i) are planning an Interested Party Transaction and (ii) without getting a “cleansing” vote of that transaction, are assuming a very serious risk of a lawsuit. If there were 5 people on the Board, and the planned dilutive issuance to X/Y was approved by the rest of the Board, then the risk profile of the transaction would be very different. Similarly, if there are other people on the cap table besides Founders X/Y and Employee A, then if their votes make up a majority of the stock not held by X/Y (the disinterested stockholders) and they approve the dilutive new stock, we’re again in much safer territory.

The key is that, in an interested party transaction, you need to get a majority of the people who aren’t getting the ‘special benefits’ to approve the deal. If you can’t, then you’re asking for pain. 

If the entire cap table is X, Y, and A, then X & Y are just asking for trouble and (frankly) deluding themselves by thinking that they can dilute A (without her consent) in a legally air-tight manner. I’ve seen founders throw out a phrase like “let’s just do a recap” (short for recapitalization) as if recaps are a magical get-out-of-fiduciary-duties card. I think that idea was spread by ‘The Social Network,’ but I’m not entirely sure. Recaps are complicated, and you still have to worry about fiduciary duties to get them done properly.

Corporate Governance is Real

The overarching umbrella of the rules, processes, etc. that govern how corporate directors and officers interact with stockholders is called ‘corporate governance.’ Founders sometimes think it’s all silliness reserved for when they go IPO, but it’s not. From Day 1, corporate governance matters. Yes, it becomes more formalized as you grow as a company and the stakes get higher, but it’s the same rules at Seed v. at Series D, just being applied differently. You better believe it matters the moment a VC is on your cap table.

Fiduciary duties do not mean that you always have to do what your minority stockholders want. That would be impossible. It just means that, as a director/officer, you have to do what’s best for the Company (the whole pie), and not just for yourself. If there’s a financing coming up that some of your stockholders don’t like, you should be safe if disinterested parties approve it as something that is the best move for the entire company. I say should, because the rules, the process, and even the language in your board resolutions matter. They can be (and often are) the difference between moving forward knowing that your decisions can’t be challenged v. handing disgruntled stockholders a loaded gun to use against you when you least want them to.

VCs and Founder CEOs: Coaching v. Undermining

TL;DR Nutshell: For a first-time founder CEO, the process of acquiring the skills to run a successful, scaled company will inevitably involve mistakes, learning, refining, iterating, etc. The best VCs engage founder CEOs as coaches, constructively pointing out weaknesses and pushing them to become great leaders. The worst VCs go into an investment having already decided that the company needs a “real CEO” and will use every mistake, no matter how common, as a reason to reinforce their viewpoint.  Know how to distinguish between the two, or you’ll be sorry.

Background Reading:

One of the great things about being a VC lawyer is that you get to observe a volume and breadth of companies and founder teams that really isn’t accessible to most ecosystem players. Executives see only their own companies. Investors see only the ones they’ve invested in. But VC lawyers interact with teams that cross geographical, investor, industry, and all kinds of other boundaries.  More data points means more opportunities for pattern recognition, and I’ve noticed that the relationship dynamics between a first-time founder CEO and her lead investors – one of the most important relationships in the trajectory of a startup – often fall broadly into one of two categories:

  • Coaching – The functional category – The founder CEO understands, from Day 1, her role as the leader of the Company and that, cap tables and corporate governance issues notwithstanding, the Board and VCs are there to provide input, guidance, constructive criticism, and whatever else is needed to help the CEO exercise her judgment in leading the Company.  If the CEO makes a mistake – the budget was missed, some projections were off, a new hire turned out to be a dud, all mistakes that happen very often, especially in the very early days of a startup – everyone acknowledges the error, provides guidance on how to improve, and keeps moving. Investors offer suggestions, connections, and other resources all built around developing the CEOs personal skillset.
  • Undermining – The dysfunctional category – Because of the differences in experience, influence, and often age, an almost parent and child-like relationship develops between VCs and the founder CEO.  Very common mistakes like those described above don’t result in constructive advice for improvement, but in “this should NEVER happen” scoldings and early discussions about what kind of ‘talent’ is missing on the team. Communications become far more about what the founder CEO is doing wrong than about how she could start doing them right.

No one is born with the skillset needed to run a successful, scaling company. Founders know that, and experienced investors absolutely know it. Even more so, the early days of a startup are often so fast-moving and full of uncertainty that problems arise through no fault of the management team, but just because sh** happens. A lot.

A group of VCs who are committed to giving the founder CEO the necessary runway and resources to become a great leader is an invaluable asset to a founder team. But, unfortunately, in every ecosystem there are also investors whose routine playbook is to pretend that every hiccup, every miss, is just another reason why they need to pull out their rolodex and bring in some ‘adult supervision.’

Coaching ≠ Entrenchment

To be crystal clear, founder CEOs sometimes do need to be replaced, particularly when the Company has reached a size/scale where it really isn’t a ‘startup’ anymore; think Series B/C+. A Board of Directors has a fiduciary duty to do what maximizes the value of the entire Company, and if it has become clear that, after repeated attempts at building the necessary skillset, a CEO simply doesn’t have what it takes, she should step aside or be removed.  If the ship is sinking, it’s unfair to let everyone drown when you could’ve replaced the captain. 

My experience is that great founders are often (but not always) quite good at acknowledging when they’ve reached their limit– they obviously want their ownership stake to produce a great exit just like everyone else’s, and if they feel like bringing in new management will get that done, they will move aside. But not until they’ve been given a real chance. Even if we all universally accept that no one who raises outside capital is entitled to run a company forever, the best investors and advisors should all agree that, given the massive personal sacrifices that founders make to build their companies, every founder CEO deserves an opportunity to make mistakes, learn from them, and mature into her leadership role without being constantly undermined.

If it’s been 2 years post-investment, you’ve cycled through ideas suggested by your Board, done the reps, studied the books, met with the mentors, things still just aren’t clicking and your Board is throwing out some names, think hard about it. That is just the Board doing its job.

But if you haven’t even closed a decent A round, your VC has you on a “tight leash” because you missed last quarter’s projections, and names (from the VCs own network) are already being suggested for new management, that is bullsh**. What you have there is an investor who planned to replace you before the ink even dried on the check.

The Importance of Transparency and Competition in Ecosystems

When I work with founder CEOs who’ve found themselves in the unfortunate situation of having an “underminer” on their cap table, my first piece of advice is simple: whining will get you nowhere. If a VC has managed to build a decent personal brand all while maintaining a consistent playbook of undermining a CEO’s leadership role from the very beginning, then he’ll respond only to consequences, not complaints.

Scarcity and opacity are the mothers of bad behavior in almost any market. If a market participant has thrived while being an a**hole, it’s because the market mechanisms needed for punishing that behavior, transparency and competition, have been absent. If you want to change the behavior, you have to change the environment. That means:

A. Never stop meeting with outside investors, and avoid contractual provisions that lock you in, early on, to a particular group of investors. Founders do themselves, their companies, and (frankly) their ecosystems a massive disservice by deciding that, once they’ve found ‘their VC,’ it’s time to stop investor discussions and ‘focus on the business.’

This does not mean that you should spend all of your time in full pitch mode – of course not – but you better believe that an investor’s knowing that you may be taking meetings with deep-pocketed California or East Coast VCs (who are increasingly looking outside of their core markets) will make them think twice about their behavior on the Board. It should not surprise anyone that the country’s VCs with the best reputations for how they treat founders (in addition to financial returns) are predominantly located in ecosystems with much more capital (and hence competition among capital) than the rest of the country.

B. Find Truly Independent Perspectives for both the Board and the management team. See: How Founders Lost Control of Their Startups, Apart from Ownership. Your independent director(s) should be actually independent – not people whom your ‘underminer’ has picked for 4 other boards before yours.  And you should know that pushing executives from their personal network onto the management team is a common way that ‘underminer’ VCs slowly unhinge the existing leadership. People remember who really got them their job.

C. Talk to other founders. Every founder approaching a VC round should be talking to the companies who’ve already taken money from their prospective VCs.  And I don’t mean just the rocket ships your VC suggested you talk to.  Recruiters know that the real data on a recruit comes from the people she didn’t list as references. You want to know how a VC treated the companies that hit road bumps, and that means doing your own diligence.

And when future founders come to you for feedback on a particular VC, play your proper role in the ecosystem and be honest. I certainly will be.  The best VCs deserve your praise – every ecosystem needs more of them, and the underminers deserve to be called out.

In any ecosystem, the best way to increase the number of coaches and marginalize the underminers is to (i) bring in new, competitive outside capital, and (ii) be transparent and honest about the capital that is currently available. Don’t whine about the players. Change the game.