When Startup Law Firms Don’t Sell Legal Services

TL;DR: Law firms inflate their costs when, instead of selling legal services, they’re actually selling prestige, luxurious offices, fun social events, fundraising connections, and all kinds of other things that aren’t legal services. The emergence of the lean boutique ecosystem is driven by pragmatic clients who just want to pay for highly experienced and specialized legal counsel, not all of that “other stuff.”

Background reading: Startup Lawyers – Explained.

If you want to understand the economics of law firms down to its most essential form, including “emerging companies” law firms that play the startup game, you can look at it this way: the main “costs” of law firms are (a) lawyers/legal talent, and then (b) literally everything else.

Analyzing the direct compensation cost of lawyers/legal talent makes it clear why no serious law firm is ever “cheap.” Serious lawyers with the rare intellectual horse power and experience (Partners and senior lawyers, not juniors) to manage massive non-routine complexity while avoiding expensive “bugs” that can’t be fixed unilaterally (the way code can be), and who’ve gone through 3 years of an over-priced education (did I say that out loud?) costing over $200K all-in, do not work for middle class compensation. Especially not the Partners who keep the whole thing together and manage the highest-level issues.

The core cost of serious legal talent sets a hard floor on the bare minimum a law firm can charge just for delivering the A-players.  Firms lacking the credibility to charge above that floor simply can’t hire the right people, and therefore can’t safely manage the kind of legal work that the top-tier handles. Those firms I refer to, lovingly, as “B-players.” The best software developers don’t work for cheap, and neither do the best lawyers. Some firms try to play games by pushing clients to work mainly with juniors and paralegals in order to save on their compensation costs – called “de-skilling” in the professional world – but the smartest clients see what’s happening and don’t trust their most high-stakes, strategic legal matters to less-skilled people operating on checklists and scripts.

Analyzing the “everything else” in the typical law firm cost structure starts to highlight just why many law firms charge prices that are dramatically higher than the cost of their legal talent. Some law firms, including many who market themselves to startups, are actually selling many things other than legal services. Those “other things” include:

  • Prestige – “We represented Apple and Uber. Using us signals your intent to be the next Apple or Uber.”
  • Extremely expensive real estate (offices), where you can feel amazing about working with lawyers who have such great taste in architecture.
  • Extremely expensive marketing events where you can mingle with other “exclusive” people and signal how amazing you are for working with such prestigious lawyers with great taste in architecture.
  • Support staff who purportedly are there to hold your hand to fundraise, work on pitch decks, talk to investors, etc.
  • Other staff building and managing things that many clients simply don’t need.

How can some law firms charge $750+/hr, and yet at the end of the day only generate “comfortable” professional services margins – nothing remotely close to the kinds of margins that draw in VCs? After paying for their extremely expensive legal talent, they also pay for this “other stuff.” You might say that firms are being wasteful, but eliminating these costs is far easier said than done for the largest firms. At the very highest end of every market, clients expect an enormous amount of polish and velvet rope. Those law firms are status symbols. Ferrari law firms are effectively selling a luxury service, and it takes money to deliver a luxury experience.

When clients ask us what we mean at E/N by a “lean” boutique law firm, we point to the above list. Lean means not paying for all of that other stuff, because many pragmatic clients know they don’t need it from a law firm. What do clients hire us for? Legal services. Highly specialized emerging companies, commercial, and M&A legal services delivered by highly experienced legal talent. When clients peruse our bios, they understand very fast that this is not a roster of B-players. They want to hire that, and not:

Prestige? No client I work with has ever suffered from the delusion that they are the next Uber, and they therefore have no desire to embarrass themselves by trying to use a law firm to signal that they’re a Unicorn. See: Not Building a “Unicorn.”

High-end offices? Please. My clients don’t give two sh**s about what my office looks like, as long as I deliver the goods (legal services).

Fun events? There are enough startup events being thrown by enough people who actually know how to throw events. Too many, some might say. Hard pass.

Fundraising connections? We negotiate and close deals, and help clients avoid being taken advantage of by the money. But there are plenty of other people and resources in the market who are far better, and more cost/time-effective, at helping with the non-legal side of fundraising than a law firm. Smart entrepreneurs know that (i) relying on a law firm to connect you to money sends a really bad signal (paid intros are weak intros), and (ii) more often than not, law firms just connect you to other VCs that they themselves work for and have long-standing relationships with, which means dangerous conflicts of interest. See: How to avoid “captive” company counsel.

We’ve told our clients for some time that they shouldn’t ask us to connect them to investors, for the above reasons; and, remarkably, somehow they still find funding without a law firm holding their hand. Apparently there are other ways to get warm intros to investors than through a law firm. Who knew? Maybe someone should write a blog post (or 30) about it.

The law firm that is super close to your money (investors) is the last firm you want representing you in taking that money, because between you (a single company) and them (a fund with lots of deals/investments and connections) their loyalty will always be owned by an influential repeat money player. Law firms that over-play their connections to investors are unethically spinning a blatant conflict of interest into a marketing ploy, so you’ll ignore the fact that they’re not actually that good at what you should really be hiring them for: high-stakes legal.

Other staff? The other day I heard about a group of lawyers dropping millions of dollars building proprietary software, and after 2 years what do they have to show? Something that looks a whole lot like Clerky, Gust Launch, or Carta. My clients aren’t going to pay me to build something that I can buy for far less money from someone else. We sell legal services. We buy (not build) software. Try to run a professional services business like a VC-backed startup, and you’ll either burn enormous amounts of money, or never ever generate a profit for your Partners, which means you won’t actually have (real) Partners, so you’re a firm of B-players. There are no VC returns in high-end legal. The margins aren’t there. Math.

Do lean boutiques have overhead? Of course. It’s what makes them more scalable and coordinated than solo lawyers. Docusign (we’re paperless), Box (all of our clients get a Box folder to access their files), Knowledge and Project Management systems, and other off-the-shelf tech tools that smart law firms know how to integrate and use, all cost money; so do recruiting and training resources. But not that much. Any serious business has overhead, but boutiques focus on overhead actually required to deliver (guess what?) legal services; not “other stuff.”

I spend a good amount of my time talking to legal tech entrepreneurs, and adopting new tools into our firm. But I don’t burn our fees on rube goldberg tools that offer more techno-BS than actual value to our clients; and therefore aren’t worth their cost.  Come at me with some nonsense about how (air quotes) “machine learning” or analyzing the “data” in contracts (is it “big data” or smaller artisanal data?) is going to DISRUPT highly complex, highly contextualized legal services from top-tier lawyers, and the bucket of water I splash in your face will be ice cold.

That lean focus on not burning money on things that don’t directly promote our end-service is what allows us to take, just as an example, a Partner who was $750/hr in BigLaw and drop their rate to $425, without changing their aggregate compensation, and while allowing them to have far better work-life balance. A win-win for both lawyer and client.

On the work-life balance point, lawyers tend to become much more skeptical of the “other stuff” their firms are paying for once they realize that all the extra overhead is directly tied to why they have to work themselves into the ground (so many hours), instead of being able to go home at a reasonable hour. More overhead means a smaller % of fees going to the actual talent, which means that talent has to work far more hours to make their comp. Again, Math. Lawyers who care about their personal lives don’t tolerate their firms burning money on nonsense. This “rationalizing” (cutting out fat) in the legal market is producing a thriving ecosystem of lean, high-end boutique law firms in various specialties; of which we are one.

We have very close relationships to many lawyers in the “Ferrari” tier of big TechLaw, in many cases because we see them on deals. Most of them intuitively understand that we are not really competing with each other. The highest end unicorn-track clients able and willing to drop $800/hr for lawyers really do expect prestige, gorgeous offices, fun events, and all kinds of other miscellaneous things from their law firm. Ours don’t. We are really selling to different people. There is no way they could run their firm like ours, and there’s no way we could run our firm like theirs. The future of the legal market is a broad ecosystem of varying firm structures catering to a broad diversity of clients with different needs, expectations, and price-points.

Our clients are very pragmatic about what they’re building, and what they want from a law firm. They’re not unicorns or even aspiring unicorns, so they see no need to use law firms that manage billion-dollar deals and IPOs. Selling for $75MM, $150MM, or $250MM is a “win” for them. They also understand that it takes real money to get serious senior lawyers and Partners who can deliver specialized and experienced high-stakes legal services for a scaling tech company. They’re willing to pay for that, but not for “everything else.”

Startup Accelerators and Ecosystem Gatekeeping

TL;DR: Startup accelerators face a fundamental challenge to their value proposition: they don’t “own” their networks, and therefore struggle to continue extracting fees for accessing them. Classic disintermediation. Their responses to that challenge take a number of forms, and generally involve either dropping their price or attempts at controlling ecosystem players; the latter of which is misaligned with the interests of entrepreneurs and startups.

Related reading:

As I’ve written before in the above posts, Startup Accelerators became “a thing” in ecosystems because they were a reasonably optimal method for solving the “noise” problem faced both by startups and investors; a problem which became more visible as the cost of starting a company went down. With far more people “starting up,” early-stage investors needed someone to help them filter out duds. The solution, referred generally as “sorting,” is similar to the value prop offered by elite universities to employers needing talented labor, and students needing credible ways to signal their talent.

By creating credible brands (signals) for quality entrepreneurs, accelerators reduced the search costs for early-stage investors who, instead of needing to filter through lots of duds themselves, had a concentrated place to build their pipeline. That value proposition attracted investors, advisors, great employee hires, etc., and over time successful “alumni,” which magnifies the value proposition to entrepreneurs who, in exchange for equity, got a fast-track to building their network and raising capital.

For some time, you had a virtuous cycle with clear “network effects.” Attract great entrepreneurs, which then attracts investors and other key people, which then attracts more great entrepreneurs, and so on and so forth; just like a classic network effect for a software platform. During this period, accelerators can build significant leverage over their ecosystems as gatekeepers to talented entrepreneurs, and use that leverage to push the market in directions the accelerator wants.

The “Network” Can’t Be Controlled

But accelerators face a distinct problem that doesn’t get talked about a lot publicly, but local market players absolutely know is there: they can’t lock in (air quotes) “their” network. It’s not proprietary. The “networks” of startup accelerators are really just compilations of individual peoples’ networks; not at all like a “network” of a tech platform for which the tech “owner” can sustainably charge access fees. Those people in the accelerator’s “network” aren’t employees of the accelerator, nor are they paid out of its returns, and so they aren’t aligned in propping up the network’s “access fee.” Inevitably, people find it worth their while to simply bypass the accelerator and makes themselves accessible to founders directly, after having built their own personal brands with a few iterations with the accelerators’ initial cohorts. If a team needs X, Y, and Z, and I know X, Y, and Z and can help them get access with my own branding/signal, why should they have to pay this 3rd-party a fee to access those people?

So after a few years of an accelerator having filtered and aggregated a network, helping great people find great founders, and great founders find great people, the network takes on a life of its own. Suddenly with a little hustle and networking, it’s not nearly as hard as it was 5 years ago to simply navigate the “network” without ever needing to pay the gatekeeper. I’ve seen this play out in a number of startup ecosystems across the country, where accelerators faced an initial golden age when they were seen as prime “sorters” of an opaque ecosystem willing to pay for the sorting, and then suddenly the quality of entrepreneurs they can get to pay their “fee” starts to take a clear downward turn. Top entrepreneurs are, by definition, fantastic hustlers. They aren’t going to pay you for something once they’ve realized they can do it themselves with a little effort, or that someone else is offering similar “access” at a lower “fee.”

Once top entrepreneurs realize that they can bypass the accelerator and access its “network” directly, and word gets around, the value proposition of the accelerator can begin to unwind. Suddenly the accelerator cohorts start to fill not with the most highly skilled entrepreneurs (those hustle it out on their own now), but with lower quality entrepreneurs less capable of making things happen “in the wild” and therefore more needy of the accelerator’s high-touch, high-priced assistance. As the quality of the accelerator’s average entrepreneur goes down, the leverage over key people on the other side of the “market” – investors, advisors, etc. – goes down, and fewer of them show up to the accelerator; which then reduces the value prop for entrepreneurs, and you get the exact reverse of the original virtuous cycle.

Seeing this dynamic play out, accelerators have three ways of responding, and I’ve seen them in different markets.

Drop the Price

The first is to simply acknowledge that the accelerator cannot maintain the original value proposition they had before the ecosystem/network had matured, and drop their price accordingly. With less significant of a signal, and less leverage over the market, the high 6-8% fee can’t be sustained, so build something leaner that can be offered at a 1-2% level perhaps. I’ve seen these “leaner” accelerators enjoy some success. Some accelerators started out with the expectation that they were going to dominate a startup ecosystem with high “access” fees, and then over time got humbled when the market delivered a reality check.

Employ the Network

Another option is to convert the accelerator into a kind of “startup studio,” where the main pieces of the network are actually employees paid by the accelerator, or at least with deeper economic ties to the accelerators’ performance; reducing their incentive to leak out of the network. The key challenge here is whether the accelerator really has the cachet/leverage, and resources, to employ those people; or whether A-players find it far better to simply stay outside and keep their pipelines more open.

Another way to “employ” certain network players doesn’t require actually employing them, but simply maintaining some economic control over them. For example, a prominent accelerator might use referral relationships with certain law firms as a way to keep those firms from questioning the accelerators’ behavior, even if it’s clearly at times not in the best interest of the startups the firms represent. That strategy is straight out of the playbook of VCs. See: When VCs “own” your startup’s lawyers and Relationships and Power in Startup Ecosystems. Offering or restricting “access” to potential investments, clients, employers, etc. has always been a currency used by startup power players to keep other market participants loyal and “well-behaved.”

Try to Lock Down the Network

This is where things start to get interesting. So I’m an accelerator enjoying success, but I can clearly see that over time my ability to keep extracting gatekeeping fees over my “network” is weakened by my inability to maintain control over the investors, founders, advisors, etc. within it. Possible solutions:

  • Lock Down Demo Day – Maintain tighter control over who gets access to demo day and, importantly, “discourage” founders from raising financing outside of demo day.
  • Lock Down Financing Structures – Maintain tighter control over how financings within the network occur, by “soft mandating” that they follow templates created and controlled by the accelerator.
  • Lock Down Network Communication with Technology – Create proprietary message boards, mail lists, and other media platforms for communicating within and navigating the network, to “incentivize” networking in ways that give the accelerator visibility and control.

Of course, none of this will ever be communicated openly as mechanisms for the accelerator to maintain power over an ecosystem/network, including founders. They’ll be spun as ways to provide efficiency and value for founders and other people. But as with much spin, there is a point at which it fails to pass the laugh test.

Listen in the market (what gets said privately rarely mirrors what is said publicly), and it becomes clear that the more aggressive accelerators have for some time been building local resistance; irritating investors who resent having a “big brother” dictating how to do biz dev and deals, irritating founders who don’t want to pay a gatekeeping fee for accessing specific ecosystem resources, and irritating other market players who don’t want a rent-seeker standing in-between them and potential business.

When an accelerator “discourages” a startup team from fundraising outside of demo day, it’s going to offer some paternalistic platitude about how having a controlled process helps “protect” the entrepreneurs, but what it’s really about is ensuring the accelerator has (i) leverage over the investor community via ability to deny and control access to its founders, and (ii) leverage over founders by controlling the venue in which they fundraise; which sustains the power of the accelerator to charge high gatekeeping fees.

Once I’ve publicly announced my cohort, the sorting is done and the signal is out. Investors don’t need me (the accelerator) anymore, and in many cases nor do the founders whose main purpose of joining the accelerator was to get “branded” to make getting meetings with investors easier. That threatens the power of the accelerator, which wants to charge not just for sorting/signaling, but for access to a network. “Locking down” outside fundraising, with some clever spin as to why it’s good for startups, is the response.

If an accelerator builds proprietary communication channels for alumni to utilize, maybe that’s to be helpful. Or maybe it’s a way of preventing the network from doing exactly what networks do organically, which is resist gatekeeping and build multiple nodes/channels to prevent a single point of entry through which a rent-seeker can extract access fees. Accelerator’s don’t hold monopolies on brands/signals that startups can leverage to get funding, and therefore other people (like angels, seed funds, and respected founders) within a “network” who can connect founders to money/other resources (offer cheaper “signaling”) are, in a sense, competitors whom the accelerator has a strong incentive to control. Maintaining control / visibility over communication channels is a way for accelerators to prevent leaner competition.

Accelerators are Service Providers, Like Everyone Else

The general conclusion from all of the above should not be that startup accelerators are bad or good; on an individual level many are of course full of great people. Instead, it should be that accelerators are profit-driven service providers and political actors, just like everyone else. They want to charge a higher price, and will do what they can to maintain their power to charge that higher price. Other market players will attempt to build alternatives, and drop that price, and the accelerators will respond by trying to compete with, block, or control those other market players. It’s just like VC, Law, and any other industry that caters to startups.

When transparent meritocracy and markets start to challenge a player’s ability to charge high fees, they often turn to politics; using backdoor relationships to build loyalties and amplify supportive messaging. Accelerators who maintain tight referral and economic relationships with specific funds, firms, and other market players do so in order to ensure there’s a loyal base of people out there toeing the party line, even as opposing voices in the ecosystem start to emerge.

For entrepreneurs, the message is simply to understand where their interests are aligned, and where they’re misaligned, with the interests of accelerators. Branding and signaling are useful. To the extent they are useful to you, use them, at the appropriate price. But by no means allow them to dictate how or when to fundraise, or how to navigate the network. It’s in startups’ interest (and that of ecosystems generally) to stay flexible and keep their options open, even if accelerators would prefer having a tight grip. The golden era of accelerators is almost certainly over, as startup ecosystems and networks have begun to mature, offering multiple accessible paths to networking and investment. But they will still have a place and function for a pocket of the ecosystem that needs them.

To the extent accelerators use politics and leverage to lock down ecosystem resources that founders could otherwise access on their own just fine, or demand that startups and investors do things in a specific way favored by the accelerator, they are no longer transparent market players; they’re rent-seeking gatekeepers. If there’s anyone that startup entrepreneurs love painting a bullseye on, it’s gatekeepers.

After-note: see Why Startup Accelerators Compete with Smart Money for some observations on how early-stage VCs are eroding the value proposition of accelerators further by bundling new roles/services alongside their investments, and moving up-stream.

Trust, “Friendliness,” and Zero-Sum Startup Games

Background reading: Relationships and Power in Startup Ecosystems

TL;DR: In many areas of business (and in broader society) rhetoric around “positive sum” thinking and “friendliness” is used to disarm the inexperienced, so that seasoned players can then take advantage. Startups shouldn’t drink too much of the kool-aid. Smile and be “friendly,” but CYA.

An underlying theme of much of my writing on SHL is that first-time founders and employees of startups, being completely new to the highly complex “game” of building high-growth companies and raising funding, are heavily exposed to manipulation by sophisticated repeat players who’ve been playing the same game for years or even decades. There are many important tactical topics in that game – around funding, recruiting, sales, exits – all of which merit different conversations, but the point of this post is really a more “meta” issue. I’m going to talk about the perspective that should be brought to the table in navigating this environment.

A concept you often hear in startup ecosystems is the distinction between zero-sum and positive-sum games. The former are where there’s a fixed/scarce resource (like $), and so people behave more competitively/aggressively to get a larger share, and there’s less cooperation between players. In positive-sum games, the thinking goes, acting competitively is destructive and everyone wins by being more cooperative and sharing the larger pie. Sports are the quintessential zero-sum game. Someone wins, and someone loses. Capitalism is, broadly, a positive-sum game because in a business deal, both sides generally make more money than if the deal had never happened.

The reality – and its a reality that clever players try to obscure from the naive – is that business relationships (including startup ecosystems) are full of both positive and zero-sum games, many of which are unavoidably linked. It is, therefore, a false dichotomy. In many cases, there are zero-sum games within positive sum games. In fact, rhetoric about “positive-sum” thinking, friendliness, trust, and “win-win” is a common tactic used by powerful players to keep their status from being threatened.

For a better understanding of how this plays out in broader society (not startup ecosystems), I’d recommend reading “Winners Take All: The Elite Charade of Changing the World” by Anand Giridharadas, who deep-dives into how, in many cases, very wealthy and powerful people (i) on the one hand, fund politicians/legislation that cut taxes and funding for democratically solving social problems while (ii) simultaneously, spending a smaller portion of the saved money on “philanthropic” or “social enterprise” initiatives aimed at addressing those same social problems, but in a privatized way where they are in more control. The latter of course comes with a hefty share of feel-good messaging about “giving back” and helping people.

The net outcome is that those powerful players direct discussion away from the full spectrum of solutions that may require addressing some unavoidable zero-sum realities, and instead get society to myopically focus on a narrower segment of purportedly “win-win” options that don’t actually threaten the power and status of the elite priesthood. There is much room to debate the degree to which Giridharadas’ perspective is an accurate representation of American philanthropy/social enterprise, but anyone with an ounce of honesty will acknowledge that it is definitely there, and large.

Sidenote: Anand is a clear hardcore socialist, and I’m not exactly a fan, but life is complicated and I’ll acknowledge when someone makes an accurate point. An enormous amount of “save the world” rhetoric is just kabuki theatre to maintain power and keep your money.

While the details are clearly different, this dynamic plays out all over startup ecosystems. They are full of influential market actors (accelerators, investors, executives) acting as agents for profit/returns driven principals, and in many cases legally obligated to maximize returns, and yet listen to much of the language they use on blogs, social media, events, etc. and an outsider might think they were all employees of UNICEF. This is especially the case in Silicon Valley, which seems to have gone all “namaste” over the past few years; with SV’s investor microphones full of messages about mindfulness, empathy, “positive sum” thinking, and whatever other type of virtue signaling is in vogue.  Come take our money, or join our accelerator, or both. We’re such nice people, you can just let your guard down as we hold hands and build wealth together.

Scratch the surface of the “kumbaya” narratives, and what becomes clear is that visible “friendliness” has become part of these startup players’ profit-driven marketing strategies. With enough competition, market actors look for ways of differentiating themselves, and “friendliness” (or at least the appearance of it) becomes one variable among many to offer some differentiation; but it doesn’t change any of the fundamentals of the relationship. Just like how “win-win” private social enterprise initiatives can be a clever strategy of the wealthy to distract society away from public initiatives that actually threaten oligarchic power, excessive “friendliness” is often used by startup money players to disarm and manipulate inexperienced companies into taking actions that are sub-optimal, because they lack the perspective and experience to understand the game in full context.

With enough inequality of experience and influence between players (which is absolutely the case between “one shot” entrepreneurs and sophisticated repeat player investors) you can play all kinds of hidden and obscure zero-sum games in the background and – as long you do a good enough job of ensuring no one calls them out in the open – still maintain a public facade of friendliness and selflessness. 

As startup lawyers, the way that we see this game played out is often in the selection of legal counsel and negotiation of financings/corporate governance. In most business contexts, there’s a clear, unambiguous understanding that the relationship between companies and their investors – and between “one shot” common stockholders v. repeat player investors – has numerous areas of unavoidable misalignment and zero-sum dynamics. Every cap table adds up to 100%. A Board of Directors, which has almost maximal power over the Company, has a finite number of directors. Every dollar in an exit goes either to common stock (founders/employees) or investors. Kind of hard to avoid “zero sum” dynamics here. As acknowledgement of all this misalignment, working with counsel (and other advisors) who are experienced but independent from the money is seen, by seasoned players, as a no-brainer.

But then the cotton candy “kumbaya” crowd of the startup world shows up. We’re all “aligned” here. Let’s just use this (air quotes) “standard” document (nevermind that I or another investor created it) and close quickly without negotiation, to “save money.” Go ahead and hire this executive that I (the VC) have known for 10 years, instead of following an objective recruiting process, because we all “trust” each other here. Go ahead and hire this law firm (that also works for us on 10x more deals) because they “know us” well and will help you (again) “save money.” Conflicts of interest? Come on. We’re all “friendly” here. Mindfulness, empathy, something something “positive sum” and save the whales, remember?

Call out the problems in this perspective, even as diplomatically as remotely possible, and some will accuse you of being overly “adversarial.” That’s the same zero-sum v. positive-sum false dichotomy rearing its head in the startup game. Are “adversarial” and “namaste” the only two options here? Of course not. You can be friendly without being a naive “sucker.” Countless successful business people know how to combine a cooperative positive-sum perspective generally with a smart skepticism that ensures they won’t be taken advantage of. That’s the mindset entrepreneurs should adopt in navigating startup ecosystems.

I’ve found myself in numerous discussions with startup ecosystem players where I’m forced to address this false dichotomy head on and, at times, bluntly. I’m known as a pretty friendly, relationship driven guy. But I will be the last person at the table, and on the planet, to accept some “mickey mouse club” bullshit suggesting that startups, accelerators, investors, etc. are all just going to hold hands and sing kumbaya as they build shareholder value together in a positive-sum nirvana. Please. Let’s talk about our business relationships like straight-shooting adults; and not mislead new entrepreneurs and employees with nonsensical platitudes that obscure how the game is really played.

Some of the most aggressive (money driven) startup players are the most aggressive in marketing themselves as “friendly” people. But experienced and honest observers can watch their moves and see what’s really happening. Relationships in startup ecosystems have numerous high-stakes zero-sum games intertwined with positive-sum ones; and the former make caution and trustworthy advisors a necessity. Yes, the broader relationship is win-win. You hand me money or advice/connections, and I hopefully use it to make more money, and we all “win” in the long run. But that doesn’t, in the slightest, mean that within the course of that relationship there aren’t countless areas of financial and power-driven misalignment; and therefore opportunities for seasoned players to take advantage of inexperienced ones, if they’re not well advised.

Be friendly, when it’s reciprocated. Build transparent relationships. There’s no need to be an asshole. Startups are definitely a long-term game where politeness and optimism are assets; and it’s not at all a bad thing that the money has started using “niceness” in order to make more money. But don’t drink anyone’s kool-aid suggesting that everything is smiles and rainbows, so just “trust” them to make high-stakes decisions for you, without independent oversight. Those players are the most dangerous of all.