Founder Compensation: Cash, Equity, Liquidity

TL;DR: Before investor money shows up, founders should pay themselves very little, if anything. As the company reaches milestones, including fundraising milestones, founder compensation increases as a % of market comp, although it rarely reaches full ‘market’ until a Series B/C or later. As a general matter, investors want founders (i) focused on the long-term success of the company’s stock and not on a lofty cash compensation arrangement, but (ii) also comfortable enough financially to pay their bills and not be distracted by financial worries.

Background Reading:

As with many things, how different parties assess and calculate appropriate founder compensation is far more of an art than a science.  One thing to keep in mind is that all comp numbers at each stage are heavily influenced by (i) location and cost of living, (ii) industry, and (iii) life circumstances of the founders.  Older founders with families tend to have slightly higher salaries than younger single founders. The same goes for founders in more expensive cities, and for founders in industries (like biotech, energy) where the founder team is made up of seasoned executives that have taken very large pay cuts to join the venture.

There are also tax nuances involved that are not the scope of this article. That being said, the below is an outline of the overarching common principles that I’ve observed among companies along the various stages of their life cycle.

Pre-Seed: Cash In, Not Out

Money in should be documented as a Founder Note or SAFE. Paying yourself a salary  at this stage makes little sense, unless there’s substantial revenue. If you need to get some money back, a small bonus upon raising a larger ($2MM+) round is sometimes kosher. 

If a startup is currently bootstrapped and not running on a sizable amount of customer revenue, paying founder salaries amounts to taking cash from one pocket and placing it in the other, while allowing the IRS to take a percentage of it. It is very rarely rational. Keep what you need to survive in your own bank account, and only fund the company with the rest.

Contributions of capital from founders beyond minimal amounts should usually be documented as a founder convertible note or SAFE (see articles above), with the expectation that it will convert later into preferred stock, providing that founder a “little extra” on the cap table and eventually in a liquidity event. It should not, however, be expected to be paid back.

However, occasionally founders will put in such a large amount of money that they really need to get some of it back much earlier than in an exit. In those instances, discussing a small ‘performance bonus’ with your seed or Series A investors can often work, as long as the amount isn’t too large of a percentage of the overall round. I’ve seen founders get a $50K ‘performance bonus’ upon raising a $2MM+ Series A, with the logic being that they were taking barely subsistence salaries for the past year and need something to help cover deferred expenses. Sometimes it works. Sometimes it doesn’t. Usually founders with personal obligations, like student loans or families to support, are able to make a more credible case for an early cash bonus. 

I would also put “Friends and Family” round territory in this category, although it depends. If you’ve raised $250K or less, which is usually what I see for F&F, paying yourself any kind of salary often doesn’t make sense. For larger F&F rounds that are meant to last for over a year, very small founder salaries can work. As a general matter, however, anyone looking to build a company without at a minimum 6-12 months of cash reserves to live off of should re-consider whether they are in the right position to start a company.

Seed/Series A: Enough to pay the bills

Founders get paid ‘subsistence’ salaries; enough to cover expenses, but low enough to where they’re still hungry for growth. 

Once investors are on the cap table and/or the company is generating real revenue, discussions about founder salaries start to make more sense. The core principle to understand in this stage is that investors will want to avoid paying founders such high salaries that they’re no longer hungry and are just enjoying the ride. The vast majority of a founder’s long-term payout should come from their equity stake in the company, and investors want founders laser focused on turning that stake (and the investors’ stakes) into cash with a successful liquidity event.   That being said, most investors also do not want founders to be so desperate for cash that they are worried about paying their mortgage, or their kids’ schooling, which will be distracting from company matters. 

While this is an extremely rough benchmark and there are all kinds of variations, if you assume 100% as being the aggregate cash compensation of a C-level executive in a respectable, matured middle-market company in a startup’s industry and geography, seed-stage founders will often get paid 20-25% of market, and Series A founders bump up to something like 35-50%. So, as an example, if $250K is ‘market’, a seed-stage founder CEO might earn $50-60K a year, and $85K-$125K at Series A; with the universal understanding that industry, cost of living, and the personal circumstances of founders will push it in either direction.

At this stage, any discussions of founder liquidity (taking some money off the table via a secondary sale) will be non-starters, and even send a negative signal to investors that the founder isn’t as bullish as he/she should be on the company’s long-term prospects. If a founder needs more money (often family circumstances), cash comp, like a special bonus, should be the focus.

Series B/C and BeyondEdging Toward Market, Liquidity

Now we’re running a real enterprise, with the market compensation to prove it. 

It’s at true “growth” rounds when cash compensation starts to edge closer to ‘market,’ and when discussions about some small founder liquidity start to make more sense.  A ‘growth round’ would generally mean that the company has found strong product-market fit, growth is going strong, and they just need gasoline (cash) to propel the rocket ship. At this stage, founder cash comp would usually be closer to 75-100% of market for the founders’ position in the company, which may still be C-level, but might not be. See: Rich v. King: The (Core) Founder’s Dilemma.

A dynamic that starts to arise at the growth stage of a company is the feeling among a founder team (and, frankly, their spouses and families), that even though the company hasn’t exited yet, they’ve ‘made it.’ They’ve made it through the sleepless nights, the chaotic weekends, and the strained personal lives, and have built something with sustainable, sizable market value… but the ‘big pay day’ may still be years away.

It’s at this stage that a spouse might ask a question like, “So… you’ve been at this 5 years and your company just raised $20MM. Why can we still not afford to buy that house I told you about?” Those types of thoughts, which are often not unreasonable, prompt discussions about founder liquidity; meaning the sale of a portion of a founders’ common stock for cash beyond an amount that would be reasonable as a cash compensation package directly from the company.

Some VCs, when prompted by a founder looking to take a little money off the table, will respond bluntly, “absolutely not.” The logic being the conventional “I want you to be hungry” mindset. Over the past few years a counterpoint to that perspective has emerged that is reflected in It All Changes When the Founder Drives a Porsche and Some Thoughts on Founder Liquidity. The logic goes something like this:

  • Once a founder has built demonstrable enterprise value and their equity stake represents a life-changing amount of money, personal psychology and (often) family dynamics can lead them to become impatient toward converting that stake into cash;
  • This impatience can lead founders to become overly conservative in company decisions, edging toward smaller, but earlier exits (early acquisition), when a little more patience and longer horizon could achieve a significantly larger outcome (larger acquisition, IPO);
  • Therefore, allowing founders a small amount of liquidity in growth stage – enough to bring something significant home to their spouses/families/friends to reflect their achievement and calm the financial impatience, but not enough to take their eyes off the much larger pot at the end of the rainbow – can maximize the value of the company, and the eventual payout to investors, in the long run. 

You’ll still often run into both the “keep them hungry” and “let them take a little off the table” mindsets within a single cap table, but I would say the latter view, that some founder liquidity (think 5-10% of their stake) in true growth rounds can push founders to achieve bigger exits, is winning out. It depends a lot on the context, and on the particular investors.

So to summarize, while there are wide variations in the market, some reasonable, rough guidelines for founder comp are:

Pre-Seed / F&F: All equity, minimal or no cash comp, liquidity impossible.

Seed: 20-25% of market cash comp, liquidity impossible.

Series A: 35-50% of market cash comp, don’t ask about liquidity.

Series B-C+: 75-100% of market cash comp, small liquidity possible in right circumstances.

Did you get a “good” valuation?

TL;DR: What a “good” valuation is depends highly on context: geography, industry, timing, size, team experience, value-add of money, control terms, and a dozen other variables. Be careful using very fuzzy guidelines/statistics, or anecdotes, for assessing whether you got a good deal. The best valuation for your company is ultimately the one that closes.

VC lawyers get asked all the time by their clients to judge whether their financing terms are good, fair, etc; especially valuation. And that’s for good reason. There are very few players in ecosystems who see enough volume and breadth of deals to provide a truly informed assessment of a financing’s terms. Executives have usually only seen their own companies. Accelerators see only their cohort’s. Most advisors/mentors have even more limited visibility.

But VC lawyers/firms with well-established practices see deals that cross geographic, industry, stage, etc. boundaries.  In addition to a firm’s internal deal flow, there are third-party resources that can be subscribed to with data on VC valuations across the country and the world. Those resources tend to be expensive (5-figure annual subscriptions), and only firms with deep VC practices will pay for them. Given how much you’ll be relying on your lawyers for advice on your financing terms (for the above-mentioned reasons), ensuring that they are objective (and not biased in favor of your investors) is crucial. 

The above all being said, founders should understand that determining valuation at the early stages of a company (seed, Series A, B) is far far more an art than a science. It is for the investor making the investment, and it is for the people judging whether the terms are “good.” That’s why relying on broad metrics like “median Series A valuation is X” is problematic; there are simply too many variables for each company that could justify deviating from the median, in either direction (lower or higher).

What some people call a seed round, others might call a Series A. Some companies raise a Series A very early on in their company’s history because the nature of their product requires serious capital expense to even get to early milestones. Other companies bootstrap for a decade and only use a Series A as true growth capital (the way others would use a Series C or D). I saw a $150MM ‘Series A’ once. I’ve also seen $500K ‘Series A’s. And everything in between as well. So whenever someone asks me “what’s a good Seed or Series A valuation?” the answer has to start out with: “it depends.” 

Below is a break-down of the mental analysis that I might use in assessing a company’s valuation. Remember, it is an art, not a science. There are widely varying opinions here, and this is just one of them. Consider it a set of suggested guidelines, not rules.

1. What was the last valuation a professional investor was willing to pay, and what progress has been made since then?

The easiest answer to “what is X worth?” is “whatever price someone was willing to pay.” While not entirely helpful in the VC context, it certainly is relevant. If you’re doing a Series A and you have institutionals who invested in a convertible note at a $5MM cap a year ago, the obvious question then is “how much progress has been made since then?” This, btw, is why it’s dangerous for companies to set their own valuations without a true market check from professional investors. Your earlier valuations will influence your later ones.

2. What city are you in?

Location. Location. Location. One of the strongest determinants of valuations is the density of startup capital in the city your company operates in; because density means competition. Silicon Valley valuations are not 2-3x those of the rest of the country because the VCs there are just nice guys who are willing to pay more. It’s a function of market competition. SV has the highest valuations. NYC follows. And then there’s the rest of the country, with variations by city. Austin valuations are generally higher than Atlanta’s, which are generally higher than Houston’s or Miami’s. General deal terms are also more company-friendly where there is more investment density.

While the entire concept of “founder friendly” investors does have an important moral/human dynamic to it, people who play in the space enough know that at some foundational level it is a form of self-interested brand differentiation. The ‘friendliest’ investors are the ones in the most competitive, transparent (reputationally) markets. Why take our money over theirs? Because we’re ‘founder friendly’… which can mean a whole lot of things; some of which are relevant, and others which are nonsense.

Yes, online networks are breaking down geographic barriers and you are seeing more capital flow between cities/states, but the data is still crystal clear that if a Silicon Valley VC is investing in an Atlanta or Austin company, they are going to want to pay something closer to Atlanta or Austin (not SV) prices. Much like all the Ex-Californians buying up Austin homes, they likely will pay slightly above the local market (and in both cases, it pisses off local buyers), but not much. 

3. How much is being raised?

Valuations can (and often do) vary widely between markets, while the actual dilution that founders absorb doesn’t vary as much. How is that? Because founders in markets with higher valuations raise larger amounts of money, and founders in markets with lower valuations raise smaller amounts of money; in each case getting the VCs/investors to their desired %. A $1MM raise at a $4MM valuation produces the same dilution as a $5MM raise at a $20MM valuation.

You should never close any round without modeling (lawyers often help here) the actual dilution you are going to absorb from the round, including any changes required to your option pool. Many investors focus first on their desired % and then back into the right valuation and round size. Smart founders should focus on %s as well. It’s not intuitive; especially if you have multiple rounds involved.

4. Who are the investors?

Value-add, known-brand institutional VCs and professional angels that will be deeply engaged in building your company after the check hits are (obviously) worth a lot more than investors who just bring money. And they will often price themselves accordingly (lower valuations). Some money is greener.

Diligencing the valuations your specific investors were willing to pay for their past investments is a smart move. Again, it still requires discussions about the differences between companies, but it can help address any statements like “we never pay more than $X MM for Series A.”

5. What are the other terms?

A $4MM valuation with a 1x non-participating liquidation preference looks very very different in an exit from a $6MM valuation with a 2x participating liquidation preference. So does a $3.5MM valuation with investors getting 1 out of 3 Board seats v. a $5MM valuation with them getting 2/3. The non-valuation terms matter. A lot. Juicing up valuations by accepting terrible ‘other’ terms gets a lot of companies in trouble. 

6. Other Business-Focused Variables

  • What are valuations within this specific industry looking like over the past 12 months?
  • What are the obvious acquirers paying for companies they buy?
  • Where is the company in terms of revenue? Revenue-multiples generally don’t have a place in early-stage, but a $25K MRR v. $300K MRR absolutely influences valuation.
  • Any serial entrepreneurs on the team? Good schools? Other de-risking signals?
  • What’s growth look like?
  • Size of market?
  • etc. etc. etc.

Obviously, multiple term sheets are a great way to have a very clear idea of where your valuation should be, but in most non-SV markets that is a privilege bestowed on a small fraction of companies.

Take-homes:

A. If your friend’s startup got X valuation for their Series A round, that can be totally irrelevant to what valuation you should get,

B. Other terms of the financing matter a lot too, as well as who is delivering them, and

C. If you have in your hand a deal that isn’t exactly at the valuation you wanted, remember that there are thousands of founders out there who got a valuation of $0.

Over-optimizing for valuation can mean under-optimizing on a host of things that matter far more for building your business. Get the best deal that you can actually get, given your business, location, and investors, and then move forward. And ignore the broad market data, particularly the Silicon Valley data, that isn’t relevant to your own company.

It’s Not Introvert v. Extrovert. It’s Whether You Can Sell.

TL;DR: People from various intellectual/technical backgrounds tend to over-value IQ and undervalue EQ; meaning that they neglect just how crucial communication/sales skills are for executives/founders, especially a CEO.

I spend a good amount of my time training lawyers not only on how to use technology effectively (because lawyers are second only to doctors in sucking at tech adoption), but on the key ‘soft’ skills that underly client satisfaction. As a profession, lawyers dramatically over-value their credentials and under-value basic human skills like the ability to charismatically start, lead, and end a serious conversation. But when you step back and analyze how lawyers perform throughout their careers, it becomes extremely clear that far less ‘intelligent’ lawyers are the employers of lawyers with significantly better credentials.

Why would that be? Because for lawyers, legal skills get you a job, but communication skills get you clients. And without clients, no one has jobs. Any lawyer who wants to move from being a “worker bee” to leading client relationships needs to self-critically assess and devote serious attention to her/his communication skills: reading people for their pain points/values and adjusting your message, building rapport with diverse people, speaking crisply and confidently, etc. And the exact same can be said about a founder who wants to be and stay CEO.

Everything is Selling

When investors want to discuss investment, when employees want to discuss employment, or when key early customers want to discuss the product/business, whom do they ask for? The company’s technological savant? No. They want to talk to the CEO. The 3 core jobs of a founder CEO are to find customers, recruit employees, and close on investment. All three of those require strong sales and communication skills, because 90% of the work is deep, serious conversation. As the company scales, those tasks become more segmented, but at early-stage the CEO, and only the CEO, can get them done effectively.

All the time I see founder teams full of MIT, Stanford, etc. technical degrees, and a CEO who went to an unremarkable school. But 5 minutes into a conversation with them you know exactly why he’s CEO. He can sell. And I’ll see VCs who are fine keeping X founder as CEO, but insist that Y step aside for an outside CEO. Why? Because Y can’t sell. Sure, I may be over-simplifying a bit, but not by much. Assuming you aren’t dealing with a VC who always replaces founders purely for control purposes, whether or not a VC trusts you in the CEO seat often boils down to whether you can look them straight in the eye and convince them, through well-articulated conversation, that you are ‘CEO material.’

Sales Skills ≠ Extrovert. Find a Coach.

Like any other skill, sales skills can be learned, practiced, and taught, but it takes honest self-criticism and time. And they do not even remotely boil down to whether or not you are an extrovert. Shyness/social anxiety/bad communication are dysfunctions. Introversion is not a dysfunction; it’s just a personality orientation. Sales/communication skills tend to come more naturally to extroverts, but there are extroverts who are terrible at sales (often because they are glad-hander loudmouths), and there are introverts who are fantastic at it. Apart from self-practice, there are excellent executive coaches who can be engaged to help founders improve their ‘presence’ in conversation.

By no means should the above be interpreted by smart, technical founders as that they absolutely need to go out and find a schmoozer MBA to put on their team. The best lawyers (and executives) are extremely technically smart and know how to communicate. It should, however, be read to mean that you should rid yourself of the delusion that your technical skills/intelligence alone will ensure your position on your company’s executive team. ‘Soft skills’ are at least as important as ‘hard’ ones, and the faster you improve yours, the greater chances you’ll have of getting customers, employees, and investors to not only ‘buy’ your product and company, but ‘buy’ you as an executive as well.

Why Your [Specialist] Lawyer Sucks

TL;DR Nutshell: A common complaint from startups about their law firms is that, while they like their corporate counsel, the ‘specialists’ (patent, employment, benefits, export, etc.) that they end up working with suck. The core reason for this usually has to do with the incentives of large, outdated law firms to cross-sell their poorly-fitted specialists, even when better suited alternatives can be found elsewhere.

Background Reading:

Here are some very common complaints I’ve heard from funded startup founders about their law firms:

  • The patent lawyer I got connected to knew nothing about the background technology of our product. I spent half a day explaining the basic tech/science, and frankly had to do all the legwork myself.
  • The benefits/ERISA lawyer I spoke with took me through all kinds of corner cases/issues that seem far more relevant to a large company than to my startup, when all I want is an off-the-shelf equity plan and to grant a basic employee option.
  • I e-mailed the employment law specialist they referred me to about a time-sensitive executive termination issue, and it took 5 days to get a response, and it ended up being a junior lawyer they ‘throw’ to companies at my stage.
  • My TOS needed to cover some touchy healthcare privacy issues because of the nature of our (med-tech) product, but the guy my lawyer sent me to could barely tell me the basics of HIPAA.

Specialists and Sub-Specialists

One of the most important concepts founders need to understand in interacting with lawyers is that lawyers, just like doctors, have specialties and even sub-specialties; at least the good ones do. Corporate law is a specialty. Startup/VC Law is a sub-specialty of corporate law. There are also energy-focused corporate lawyers, healthcare-focused corporate lawyers, etc. The sub-specialties available in a city mirror the types of industries that dominate the local economy. That’s why Houston startups often use Austin tech/vc lawyers, and Austin energy companies often use Houston energy lawyers.

If you work with a generalist lawyer who dabbles in a little real estate, corporate law, litigation, and maybe does a few tax returns on the side, you’re asking for a world of pain if you’re building a scale-seeking tech company. But even if you work with a general corporate lawyer, failing to work with one who focuses on technology and venture capital (sub-specialty), you will waste time and money.

In the end, it’s all about incentives. 

OK, so now you understand that depending on the issue, you need corporate, tax, patent, trademark, employment, etc. etc. specialist lawyers. The question then is: which one should you use? Large, traditional law firms (BigLaw) always have the same answer: “use ours!” Nevermind that the benefits lawyer I’m sending you to spends 95% of her time talking to billion-dollar companies and will take 10 days to respond to your itty-bitty (to her) issue. Nevermind that “my patent guy” has a BS in chemical engineering and still uses a Blackberry, and you’re trying to patent a piece of consumer hardware. Nevermind that the lawyer I just sent you to keeps (as compensation) only 20% of the $650/hr he charges you, and there are far smarter lawyers in his specialty at a boutique charging half his rate.

Two law firm concepts: “origination credit” (I make money off of the lawyers in my firm that you use) and “cross-selling” (my firm expects you to use our firm’s specialists) are at the core of why so many startups end up wasting time, energy, and money dealing with specialist lawyers who (for startups) suck; because they are either over-kill, not responsive enough, or simply unnecessarily expensive.

Ecosystem v. BigLaw

You would think that, as a startup/VC lawyer at a boutique law firm, I would always tell companies that they should avoid BigLaw and choose focused boutiques instead (the “ecosystem” I write about). You’d be wrong. No matter how much disruption occurs in healthcare, pushing medicine out of hospitals and closer to the patient, you will always need the Mayo Clinics of the world. In that sense, BigLaw still “works” very well in a very specific context, and that context is very large, complex M&A transactions and IPOs.

We regularly tell clients that, while our senior partners have closed and managed $750MM, even billion-dollar deals as partners in BigLaw, boutique firms are institutionally not designed for fast, complex, very large transactions requiring armies of lawyers and other staff who can be rapidly deployed onto a large deal. That being said, the vast majority of startups, even successful ones, will never, not even in their exit transaction, need those kinds of resources. 

Right-Sized Lawyers. 

The “max out” size of boutique firms varies with their structure and the credentials of their attorneys (particularly partners, who manage the large deals). At MEMN, we say about $400MM is where our model usually stops making sense, and we’ll even assist a client in finding successor counsel to handle that size of deal. At that point, you’re probably not worried too much about your legal bill as a proportion of the overall transaction proceeds, and the players you’re working with (particularly I-Bankers in IPOs) will often require you to use a short list of brands simply for marketing and insurance purposes.

But a $100MM acquisition? $200MM? With the right boutique corporate partners running the deal (trust me, you want real partners running your exit; read bios), and the right specialists chosen for the project, wherever they are, that is not (and has not been) a problem. The newly emerging ecosystem of top-tier boutique law firms can easily thrive while still being totally honest about its limitations. It cannot represent Uber. Uber needs BigLaw. But there are plenty of successful tech companies who aren’t Uber but still need serious legal counsel.

If you have decided that you want and need BigLaw, my completely honest suggestion to you is that you go all-in and choose one of the very small number of Silicon Valley based brands that regularly represent the tech unicorns of the world. While you will still deal with several of the “poor fit” issues that plague young startups using over-sized law firms, those firms are the most likely to at least have specialists and sub-specialists who understand issues faced by technology companies, and they at least try to work well with startups.  You’re “locked in,” but at least you’re locked into a place with lawyers who can competently address your needs.

Choosing a BigLaw firm that is not one of the top tech brands will be like going on your once-in-a-lifetime luxury off-roading trip in the mountains, and buying a $200K Ferrari for the task. Your friends (who aren’t morons) will show up in souped-up Range Rovers. If you’re going big on bling, at least do it correctly.

For the rest of the world’s founders who need serious legal counsel, but honestly don’t see themselves needing the institutional resources of BigLaw any time soon, the emerging boutique ecosystem (which is thriving outside of Silicon Valley) offers a serious answer to the “my specialist lawyers suck” problem: well-compensated, top-tier, responsive lawyers at right-sized firms, chosen not because of background economic incentives, but because they are the right lawyers for the job. 

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 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.