Moving (Too) Fast and Breaking Startup Cap Tables

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As I’ve written many times before, the “move fast and break things” ethos, which makes absolute sense in a software environment where fixing “bugs” is quite easy and low-stakes, becomes monstrously expensive and reckless when applied to areas where the cost of a mistake is orders of magnitude higher to fix (if it’s fixable at all). Silicon Valley got a very visible and expensive (to investors in terms of capital, and founders in terms of legal errors and terrible legal advice) lesson in this reality a while back with a very well-funded (but ultimately failed) legal startup heavily promoted as enabling (via over-hyped vaporware) startups to “move faster” and save significant costs. That legal startup was, perhaps unsurprisingly, controlled by money players with all kinds of reasons to profit from startups (that they invest in) getting weak legal and negotiation guidance. No one wants an in-experienced founder to move fast and mindlessly do what investors want more than… those investors.

That fundamental point is one that inexperienced founders need to keep their eye on throughout their entire fundraising and growth strategy. Notice how, for example, certain Silicon Valley groups adamantly argue that SV’s exorbitant rents and salaries are nevertheless worth spending capital on, and yet simultaneously they will howl about how essential it is that startups minimize their legal spend (a small fraction of what is spent on rent and salaries) in fundraising, and move as quickly as possible; usually by mindlessly signing some template the investors created? Why? Because they know that the one set of advisors most capable of “equalizing” the playing field between inexperienced startup teams and their far more seasoned investors is experienced, independent counsel. Aggressive (and clever) investors say they want you to adopt their preferred automation tools and templates because they care so much about saving you money, but the real chess strategy is to remove your best advisors from the table so that the money can then, without “friction,” leverage its experience and knowledge advantage.

At some obvious level, technology is an excellent tool for preventing errors, especially at scale when the amount of data and complexity simply overwhelms any kind of skilled labor-driven quality control mechanism. But there is a point at which people who sell the technology can, for obvious financial incentives, over-sell things so much that they encourage buyers to become over-dependent on it, or adopt it too early, under the delusion that it is far more powerful than it really is. This drive to over-sell and over-adopt tech for “moving really fast” is driven by the imbalance in who bears the cost of fixing “broken things.”

Ultimately the technology seller still gets paid, and puts all kinds of impenetrable CYA language in their terms of service to ensure that no one can sue them when users zealously over-rely on their products in ways clearly implied as safe by the tech’s marketing. Founders and companies are the ones who pay the (sometimes permanent) costs of a poorly negotiated deal or contract, or in the case of cap tables incorrect calculations and promises to employees or investors.

In the world of cap tables, automation and tracking tools like Carta (the dominant player, justifiably, by far) are enormously valuable, and doubtlessly worth their cost, in helping the skilled people who manage the cap tables keep numbers “clean.” In the early days of Carta’s growth (once called eShares), there was a general understanding that cap tables rarely “break” before the number of people on the table exceeds maybe 20-30 stakeholders as long as someone skilled at managing cap tables (in excel) is overseeing things. That last part about someone skilled is key.

There are in fact two broad sources of cap table errors:

  • Using Excel for too long, which creates version control problems as the number of stakeholders grows; and
  • Management of cap tables by people who are simply too inexperienced, or moving too quickly, to appreciate nuances and avoid errors.

Technology is the solution to the first one. But today it’s increasingly becoming the cause of the second one. The competitive advantage of technology is speed and efficiency at processing large amounts of formulaic data. But the advantage of highly-trained people is flexibility and ability to safely navigate nuanced contexts that simply don’t fit within the narrow parameters of an algorithm. In the extremely human, and therefore subjective and nuanced, world of forming, recruiting, and funding startups in complex labor and investor markets, pretending that software will do what it simply can’t do –  delusionally over-confident engineers notwithstanding – is a recipe for disaster. The combination of new software and skilled expertise, however, is where the magic happens.

The Carta folks have been at this game long enough to have seen how often over-dependance on automation software, and under-utilization of highly trained and experienced people in managing that software, can magnify cap table problems, because it creates a false sense of security in founders that leads them to continue flying solo for far too long. Sell your cap table software as some kind of auto-pilot, when the actual engineering behind it doesn’t at all replace all the things skilled experts do and know to prevent errors, and you can easily expect ugly crashes.

That’s why Carta very quickly stopped promoting itself as a DIY “manage your cap table by yourself and stop wasting money on experts” tool and evolved to highly integrate outside cap table management expertise, like emerging companies/vc law firms and CFOs; who spend all day dealing with cap table math. They realized that the value proposition of their tool was sufficiently high that they didn’t need to over-sell it as some reckless “you can manage cap tables all by yourself!” nonsense to inexperienced teams who’ve never touched a cap table before. The teams that use Carta effectively and efficiently see it as a tool to be leveraged by and with law firms, because startup teams are rarely connected to anyone who is as experienced and trustworthy (conflicts of interest matter) in managing complex cap table math better than their startup/vc law firm.

But as is often the case, the cap table management software market has its own “race to the bottom” dynamics – but a better name may be the “race to free and DIY.” If I’m a company like Carta, and I know that truthfully very few companies need my tool before maybe a seed or Series A round (excel is perfectly fine, flexible, and simple until then), I’m still extremely worried that someone will use the time period before seed/Series A to get a foothold in the market and then squeeze me out as their users grow. That someone is almost always a “move fast and break things” bottom-feeder that will, once again, over-sell founders on the idea that their magical lower-cost DIY software is so powerful that founders should adopt it from day 1 to save so much money by no longer paying for expertise they don’t need.

Thus Carta has to create a free slimmed down version, and they did. But they’ve stuck to their guns that cap tables are extremely high-stakes, and even the best software is still extremely prone to high-cost errors if utilized solely by inexperienced founders. That’s why Carta Launch has heavy ties to a network of startup-specialized law firms. It’s free as in beer, but honest people know that it still needs to be used responsibly by people who fully understand the specific context in which it’s being used, and how to apply it to that context.

But the bottom-feeders of cap table management are of course showing up, with funding from the same people who were previously happy to impose costs (errors, cleanup) on inexperienced teams as long as their software gets adopted and their influence over the ecosystem therefore grows. The playbook is tired and predictable.

Why are you using that other (widely adopted and respected) technology that still relies (horror of horrors) on skilled humans? It’s 2020, you need :: something something automation, machine learning, AI, etc. etc. :: to stop wasting money and move even faster. Our new lower-cost, whiz-bang-pow software lets you save even more time and manage your cap table on your own, like the bad ass genius that you are.

We know where this is going. Many of us already have our popcorn ready. While before I might run into startups who handled only a formation on their own, and show up with a fairly basic and hard-to-screw-up cap table, I’m increasingly seeing startups who arrive with seed rounds closed on a fully DIY basis, and totally screwed up cap tables involving investors and real money. They also often have given up more dilution than they should’ve, because no independent, skilled expertise was used to help them choose and negotiate what funding structure to use. Clean-up is always 10x of what it costs to have simply done it right, with a thoughtfully chosen (responsible) mix of technology and skilled people, on Day 1.

Technology is wonderful. It makes our lives as startup/vc lawyers so much better, by allowing us to focus on more interesting things than tracking numbers or inputting data. The stale narrative that all VC lawyers are anti-technology really gets old. We were one of the first firms to adopt and promote Carta, along with numerous other legal tech tools. Not a single serious law firm views helping their clients manage cap tables as a significant money driver. But that’s like saying no serious medical practice views X or Y low-$ medical service as a significant money driver. Something can be a small part of a professional’s expertise, and yet still way too contextual, nuanced, and high-stakes to leave to a piece of software pretending to be an auto-pilot.

When the cost of fixing something is low, move as fast as you want and break whatever necessary. But that’s not contracts, and it’s not cap tables. In those areas, technology is a tool to be utilized by still-experienced people who regularly integrate new technology into their workflows, while maintaining skilled oversight over it. Be mindful of software companies, and the clever investors behind them, who are more than happy to encourage you to break your entire company and cap table as long as you utilize their half-baked faux-DIY tool. Their profit is your – often much larger than whatever money you thought you were saving – loss.

Bundled v. Unbundled Startup Capital

TL;DR: The market for early-stage startup financing has reached a level of fragmentation and hyper-competition (among capitalists) never seen before. This competition has led to an increasingly atomized market, with a multitude of players offering different takes on the traditional “bundled” offering of smart venture capital. Startups and founders should understand the reasons behind the marketing narratives pushed by each of these players, so they don’t get too swept up in an overly simplistic strategy for how to raise capital. The best strategy is to diversify your capital sources, while still allowing room for smart leads writing large enough checks to provide real value add.

The world of early-stage startup financing looks extremely different today than it did even 5 years ago, and completely unrecognizable to the market of a decade ago. The reasons are fairly straightforward. Near-zero interest rates and slowing of international economic growth, together with government policies of quantitative easing (which inflate traditional asset prices and make further returns harder to achieve) have produced a surge in the amount of capital seeking any kind of “alpha” in the seemingly “final frontier” of early-stage startups. There is far more money chasing startups than perhaps any time in history.

This surge in early capital naturally produces a surge in competition among early capitalists. In order to navigate that competition, capitalists, just like any other service provider, seek ways to differentiate themselves in the market to avoid appearing too much like a commodity. It’s this need for early capitalists to differentiate themselves that has produced the “atomization” or unbundling of startup finance that is increasingly visible in the market. The point of this post is to help founders and early teams understand that unbundling in assessing their own financing strategies.

To speak of unbundling of course requires first understanding the original bundle. Historically, conventional venture capitalists “sold” the following bundle to startups:

  • Green cash money (obvious)
  • Signal – a brand that credibly signaled “eliteness” to the market (de-risking to an early startup), making it easier to further attract capital, employees, commercial partners, etc.
  • Network – a deep rolodex/LinkedIn network of contacts to leverage in recruiting and expansion
  • Advisory – active involvement on Boards and “coaching” to inexperienced executive teams.

In the very early days of conventional venture capital, VC was very scarce. In many markets there was quite literally one, maybe two funds, who served as gatekeepers to the market; and unhesitatingly used their market dominance to squeeze teams on valuation and corporate governance power. This “asshole” behavior inevitably produced demand for alternatives.

Enter the new “friendly” venture capitalists. Very large VC funds started to break up because the personal brands of high-profile VCs incentivized them to form their own funds with fewer mouths to feed. Growing interest in early-stage also brought in new market entrants. As the VC market evolved from a more oligopolistic structure to an increasingly fragmented and competitive market, the need for differentiation increased. “Friendliness” (or at least the well-calculated appearance of it) became a successful way to achieve that differentiation. You now had VCs actually competing with each other based on their reputation. But the general bundle offered by those VCs largely remained the same.

Another successful form of differentiation in this era involved going deep on “value add” services. Particularly in SV but now also in other markets, VC funds began to hire non-partner staff whose purpose was to, completely apart from providing money and Board service, help CEOs with recruiting, marketing, sales, etc. as a kind of external extension of their internal team. All that extra staff naturally costs money, and increases the overhead structure of the fund, which then increases their pressure to achieve highly outsized returns and avoid overly generous valuations.

So in the initial era of startup funding growth, VCs became “friendlier” (though caveats are worth emphasizing, see Trust, “Friendliness,” and Zero-Sum Startup Games) – and bulkier. But the flood of new capital kept on coming. VCs continued splintering off and forming micro-funds. More entrants arrived. Successful exits produced new, younger teams interested in trying their luck at the VC game. What to do with the VC market becoming even more competitive? Differentiate even further.

Enter accelerators and seed funds, and eventually pre-seed funds. As the true Series A market became increasingly crowded, continued competition among capitalists led many to conclude that the new way to avoid commoditization was to go earlier in the life cycle, closer to the territory once filled exclusively by angels (named as such because of their willingness to take risks once deemed off the table for professional investors). Rather than continuing the game of bulking up and emphasizing the “full package” bundle of traditional VCs, these new institutions sought differentiation by slimming down, and emphasizing their ability and willingness to move fast and early. Those old-school VCs are slow and over-bearing, the marketing content says. They don’t really provide any value-add. Take our cheaper, faster, “friendlier” money instead.

We are now entering a new era where “solo capitalists” are the hot topic. New in some ways, but the same dynamics of market competition and necessary differentiation are quite old. Why take money from a fund at all, when you can just raise from a set of successful solo founders? They’re super friendly, don’t care about a board seat, and will move lightning fast without pestering you with “negotiation” or other trivialities. Their ultra-low overhead also means they can pay higher valuations. And of course they’re enabled by new tech platforms for raising and distributing capital that are very much invested in the increasing atomization of startup capital, which increases demand for technology to coordinate and facilitate that atomization.

In 2020, the market of very early-stage funding for startups now looks like this:

  • Solo angel investors
  • Angel networks
  • Angel “syndicates”
  • Accelerators of various flavors
  • Scout money from “bulky” traditional VCs
  • Pre-seed funds
  • Seed funds
  • Series A funds that invest in seed rounds
  • Solo VCs
  • “Lean” startup lenders

Throw in the reality that geography is hardly a barrier to capital flows now – especially in the COVID era – and the early-stage funding market has reached a level of hyper-fragmentation and competition that was unimaginable a decade ago. Within a particular market, the number of players has shot up dramatically, and now those players are increasingly happy to cross state lines.

This is undeniably a fantastic environment for top-tier teams looking to raise early funding. It’s also undeniably a far more stressful environment to be a startup investor. Ten years ago being a VC meant everyone came to you, very warm intro required, and you called the shots. Now VCs hustle so hard for visibility some are even engaging production studios to help them create polished youtube channels. Others don’t even require intros anymore and have opened their DMs on twitter. There are even jokes about VCs trying to create viral memes to get eyeballs. Life comes at you fast.

The important message for startup teams is to understand why the landscape now looks the way it does, and the incentives behind why any particular type of investor markets itself the way it does. Accelerators, for example, now face far more competition than they did in their golden era, particularly from seed funds with legitimate “value add” offerings. See: Why Accelerators Compete with Smart Money. Because the “bundle” of an accelerator is heavily weighted toward its network and signaling value, accelerators have for some time been incentivized to promote a narrative of “dumbing down” early capital that doesn’t have its own competing network, thus keeping the accelerator’s value proposition somewhat relevant.

Similarly, ultra-lean funds and Solo VCs lack by design the resources of larger funds, and thus they are incentivized to push a narrative that traditional “hands on” VCs don’t really add value. The new lean players don’t have the time or the resources to add value themselves, so best to talk as if that particular part of the traditional bundle isn’t that meaningful anyway.  This all, of course, is easily disproven by the number of founders in the market who credibly testify to the value (in advisory, network, deep long-term pockets) in having a large fund with full skin-in-the-game on your Board and cap table. Some (not all) large funds really do provide significant added value.

And of course, traditional VC funds talk their own books with the exact opposite story. The fragmented lean investors are all spray-and-pray “dumb money” looking for party rounds. Teams need value add from seasoned, steady hands willing to roll up their sleeves on Boards. You need more than atomized money. You need a trusted “partner” to shepherd you toward success.

There is absolutely no need to take sides in all of these narratives. Why should you? Every player in the market offers a grain of truth, but also exaggeration and over-simplification, in what they’re saying. The most important thing is not to get too swept up in moralizing or marketing. Understand what each player is selling, and understand what your particular needs are.

Often times the smartest teams do a bit of “shopping” across various aisles in the new VC supermarket. Team up with a reputable seed fund, but use your optionality to ensure the terms are reasonable. Let them write a large enough check to be emotionally invested, but fill the rest of the round with smaller high-signal checks that will also be motivated to connect you with their networks. For good measure, if you have interest from a traditional Series A VC fund, let them write a small check in your seed round to keep the connection warm when Series A discussions start. The fact that they know how well networked you are (thanks to the other players on your cap table) will ensure good behavior at the Series A term sheet stage.

Contexts will vary and team needs will vary, so the particular mix of early capital any particular startup takes will naturally vary as well. Stay flexible and avoid rigid theories about the (air quotes) “right” way to raise funding. But in all cases, make an effort to diversify your network and capital sources. Nothing ensures good behavior from the money better than making it crystal clear that you are well-networked and happy to take someone else’s check if your current investors don’t play ball. You can do so while still building strong connections with your investors, demonstrating that you value their relationship. This is a great time to be an entrepreneur, whether in or outside of Silicon Valley. In navigating the new early-stage funding market, don’t drink too much of anyone’s kool-aid, and shop wisely.

Independent Counsel in an Economic Downturn

TL;DR: In all parts of an economic cycle, up or down, there is significant value in having independent (from investors) strategic counsel that you can trust to protect the common stock in navigating negotiations with investors who are 20x as experienced as the founding team. In a downturn, however, the number of “company unfriendly” possibilities in deal and governance terms goes up ten-fold. That means the value of independent, trustworthy counsel shoots up as well.

Background reading:

I’ve written multiple posts on the topic of how first-time entrepreneurs place themselves at an enormous disadvantage when they hire, as a company counsel, lawyers with deep ties to their lead investors. To people with good instincts, the reasons are obvious, but for those who need it spelled out:

A. First time entrepreneurs are regularly interacting, on financing and governance issues, with market players who are (i) misaligned economically with the common stock, and (ii) 20x as experienced as the management team and largest common stockholders. They rely heavily on experienced outside advisors to “level the playing field” in the negotiations.

B. One of the most impactful strategic advisors an early set of founders/management can look to for navigating this high-stakes environment is an experienced “emerging companies” specialized corporate lawyer (startup lawyer), who (if vetted properly) sees far more deals and board matters in any given month than many sophisticated investors see in an entire year.

C. Because investors have contacts with/access to lots of potential deal work, and corporate lawyers need deal work, aggressive investors have come to realize that their “deal flow” is a valuable currency that can be leveraged with an overly eager portion of the “startup lawyer” community; shall we say, “nudging” them to follow the investors’ preferred protocols in exchange for referrals. By pretending that only a handful of firms have credible/quality lawyers, they also try to block law firms with more independent, but still highly experienced, lawyers from getting a foothold in the market.

D. Founders, because they lack their own contacts and experience vetting lawyers, often find themselves influenced into hiring these “captive” lawyers. As a result, they are deprived of some of the most strategic and high-value guidance that smarter teams are able to tap into for protecting the common stock.

For a deeper dive into how this game is fully played out in the market, read the above-linked posts. The point here is not to promote an exaggeratedly adversarial take on startup-investor relations, but to emphasize a simple reality of how things really work.

The main point of this post is: in an economic downturn, when company “unfriendly’ terms are going to be far more on the table than they were in years past, the value of independent strategic counsel is magnified ten-fold. In go-go times when competition for deals and excess amounts of capital shoot valuations up and “bad terms” down, deal terms gravitate toward a closer-to cookie-cutter, minimalist kind of flavor: good valuation, 1x liquidation preference non-participating, minimal covenants, and sign the deal.

That doesn’t mean there’s really a “standard” – I’ve also written extensively about how saying “this is standard” has become the preferred method for clever investors to trick startup teams into mindlessly signing docs that are against their company’s long-term interests. But, in good times deals do tend to start looking a lot more like each other in a way that makes negotiation a little easier.

But when there’s an economic shock like what we’re experiencing right now from COVID-19, and the investor community starts to improve in their leverage, it’s inevitable that you start seeing a lot more “creativity” from VCs with terms: higher liquidation preferences, participating preferred, broader covenants and veto rights, more aggressive anti-dilution, tighter maturity dates on convertible notes, etc. etc.

In this environment, it is incalculably valuable to have people to turn to, including independent deal lawyers, who can tell you what really is within the range of reasonableness, what to accept v. push-back on, and generally what is “fair” given the environment you’re fundraising in. Independent counsel will help you protect the common stockholders, while granting your investors some terms that you may not have needed to accept a year or two ago. Captive counsel, however, will know that his/her “good behavior” (for the investors) in structuring the terms will ensure more deal flow from their real clients. And because most startup teams are understandably lacking in market visibility, they have no way to quality-check the advice they’re getting. Trust is everything here.

Research and diligence your legal counsel just like how you’d diligence any high-stakes advisor. Importantly, ask them what VCs they (and their firm) represent and/or rely on for referrals. They may be great, very smart people, but if the answers you get make it clear that they are closely tied to people likely to write you checks, find someone with more independence. A muzzled corporate lawyer is ultimately an over-priced paper pusher.

 

Startup Legal Fee Cost Containment (Safely)

Given the COVID-19 crisis, every startup (every company really) is laser-focused on cost-containment. The below are some guidelines for getting legal work done efficiently, without relying on low-quality providers who will ultimately cost you far more in the long-run because of mistakes and missteps.

Related reading: Lies About Startup Legal Fees

1. Consider working with experienced, specialized lawyers in lower-cost geographies.

Bay Area and NYC lawyers have the highest rates, for obvious reasons like that the cost of living in those cities is much higher, and the firms in those markets tend to cater to unicorns with very large, multi-national transactions requiring extremely high-cost infrastructure. While it’s already been happening for years, I suspect more startups are going to realize that ECVC (Startup) lawyers in places like Seattle, Austin, and Denver have just as much visibility and specialization, but have rates that are more accessible.

In case it hasn’t already been made clear, there is nothing about corporate/securities legal work that requires you to meet in person with your legal team. You can usually shave a few hundred dollars per hour off your bills by simply using lawyers in smaller tech markets who still have the right experience.

2. Ensure your lawyers have the right specialization, and precedent/template resources for minimizing time burn.

While parts of the ecosystem have exaggerated the extent to which a “standard” startup financing really exists – stay away from Post-Money SAFEs – every serious Startup/VC lawyer has precedent and template forms they can use as starting points to avoid reinventing the wheel. A “Corporate Lawyer” is not good enough here. There are corporate lawyers who specialize in healthcare, energy, and other industries that will have no clue about ECVC norms. Read their bio, talk to clients, and/or ask about their deal experience. “Emerging Companies” and “Venture Capital” are key words to look for, unless you’re talking about an M&A deal, in which case obviously you want an M&A lawyer.

3. Unless you really are on a unicorn track, use boutiques instead of BigLaw.

“BigLaw” refers to the largest, multi-national law firms in the country; often with armies of staff and resources designed for the most complex and largest deals in the market. For the vast majority of the startup ecosystem, these firms are overkill. We’ve closed countless VC and M&A deals where the Partner on our side was $300 per hour leaner than the Partner on the other side of the table, and their bios were virtually indistinguishable.

Using a high-end boutique can dramatically lower your overall legal costs. The key issue is assessing the background/expertise of the boutique firm’s lawyers to ensure the drop in rates isn’t resulting in a drop in quality. Top-tier boutiques achieve their efficiency by eliminating infrastructure (overhead) that non-unicorn clients don’t need; not by recruiting B-player lawyers.

4. Leverage non-Partner staff (paralegals, junior and mid-level attorneys).

Some startups think they’re going to save fees by hiring a highly-seasoned solo lawyer, but this can backfire, because that solo doesn’t have any lower-cost staff. Maybe 10-30% of the legal work a typical VC-backed startup needs will require true Partner-level attention. The rest can be safely and far more efficiently handled by well-trained and monitored lower-level staff (paralegals, and non-Partner attorneys). You want a firm that has these resources available, while still having an accessible Partner that you can go to for the most high-level strategic issues.

Having a single lawyer with 10-20 years of experience do all of your legal work is like expecting a cardiologist to take your temperature, collect your insurance info, and treat your toddler for their sniffles. It’s inefficient and unnecessary.

5. For financings, opt for “simplified” deal structures if feasible.

I suspect that during the worst of the COVID-19 crisis, you’re going to see a lot more investors opting for convertible notes, because they’ll value the downside (debt) protection in case the outlook doesn’t improve in the mid-term. Convertible notes are also far simpler (lower cost) to negotiate and close than an equity round.

This is fine, and convertible notes are used hundreds/thousands of times across the country every year without problems. Just ensure you are working with specialized counsel who knows what to accept, and what to reject, in the terms. Maturity, conversion cap economics, and what happens in a down-round scenario are all key things they’ll need to pay close attention to.

If you’re able to convince investors to do an equity round, and it’s less than $2 million in total investment, you might consider a “seed equity” structure. Seed equity docs are much simpler than the classic NVCA-style VC docs, and are about 75% cheaper to close on, in terms of legal fees. They can include a provision that will allow your investors to get more robust “full” VC rights in a future round.

“Cost cutting” tips that don’t work

A. Solo lawyers won’t save you money. As mentioned above, using solo lawyers for corporate/securities (deal) work rarely results in that much efficiency. While the solo’s rates might be lower than a firm’s, the savings will be burned up by the absence of paralegals/lower-level attorneys. You also risk running into serious bottlenecks that will slow-down urgently needed work, because solos don’t have a team to help triage projects. See: Startups Scale. Solo Lawyer’s Don’t.

B. Fixed fees are more likely to result in mistakes/weak counsel than cost-saving. Fixed fees aren’t magical. Ultimately a firm has to charge a fee that aligns with what it costs to do the deal, and using a fixed fee won’t change that. But the real danger with fixed fees is that they incentivize lawyers to cut corners, because by rushing work (not negotiating/reviewing), the lawyers make more money. Ask for budget ranges, and you can talk with other founders to ensure the cost is aligned with what’s been delivered. See: The Race to the Bottom in Startup Law.

C. DIY work with fully-automated tools or templates found online will blow up in your face. Are you building a plumbing business or coffee shop? Great. Go use one of those $39.99 automated templates you can find online. Investor-backed startups are not cookie-cutter companies, and thinking you’re actually going to save money by using a fully automated template is delusional. You’re simply turning on a time bomb in your legal history that will eventually go off.

D. Do not let junior lawyers run your legal work. A huge mistake startups often make is hiring BigLaw (very high-cost firm) but thinking that by using a junior lawyer for virtually everything, they’re saving money. You do not want a junior negotiating your financing, or giving you high-stakes advice. They are great for doing checklist-oriented tasks while a Partner oversees things and interacts with the client, but not as the main legal contact. Their inexperience will cost you 10x in the long-run of whatever you think you’re saving today. If you’re struggling to cover BigLaw’s rates, the answer is to use a high-end boutique where you can still access senior lawyers but at leaner rates; not to use the most inexperienced person on BigLaw’s payroll.

There are a lot of good strategies for getting lean, but still high-quality legal counsel. The key thing is to ensure you are trimming fat from your legal budget, but not muscle.

Crisis, Relationships, and VCs

TL;DR: Startups who resisted building durable relationships with professional institutional investors, and instead pursued the “party round” competitive fundraising mindset promoted heavily by certain SV voices, are going to get a rude awakening in this current crisis. But the same may be true of startups who failed to reasonably diversify their funding options. The easiest money in good times is the first to leave the stadium in scarier times.

In talking with various market players in startup ecosystems, you’ll hear a wide spectrum of philosophies on how early-stage startups should engage with investors, particularly institutional investors (VCs). On one end of the spectrum are, of course, the VCs themselves. Predictably they tend to favor fundraising philosophies that minimize competition between investors, emphasize qualitative over quantitative (valuation, ownership %) variables, and keep the number of players on the cap table low; which improves their leverage and ability to get a bigger piece of the limited pie. Terms like “marriage” “value add” and “partnership” tend to dominate this perspective. We’ll call this “relationship maximalism.”

On the other end of the spectrum are players who might be called “competitive maximalists” as it relates to VC funding. From their perspective, there is so much capital chasing deals, and the true “value add” of institutional investors is minimal, so any smart set of founders will focus on maximizing valuation, and minimizing control given to investors. This often means “party rounds” in which lots of funds write smaller checks with no true lead. This perspective finds its greatest proponents in Silicon Valley, where the largest concentration of capital (and therefore competition among capital) can be found.

It’s important to point out that there are “money players” in the market who, at least historically, have themselves promoted the competitive maximalist view of early-stage fundraising. Prestigious startup accelerators are, effectively, a service provider whose “bundle” of value is in many ways competitive with “smart” relationship-oriented venture capital, which encourages them to promote a narrative that downplays relationship-based fundraising and promotes competitive processes. See: Why Startup Accelerators Compete with Smart Money.

In order to get more control over their pipelines, institutional VCs have moved much earlier-stage in their investing, often writing seed checks for a few hundred K as a way to get a meaningful foot in the door on a promising but very early startup. If you manage to build strong relationships very early on with VCs and “value add” angels whose brand/signal can give you access to a helpful network of talent, resources, and other investors, then your need for an “accelerator” is reduced significantly. The whole point of an accelerator is to make it easier to access talent, money, and other resources. That means your willingness to pay their “fee” of 6-8% of your cap table goes down if you can access that “bundle” via smart money, or other people, that you’ve hustled connections to on your own.

Naturally, those accelerators don’t like that, so they’re incentivized to promote a philosophy that makes founders believe all institutional investors are effectively the same, and that relationship-oriented early-stage VCs who resist competitive fundraising processes and very high valuations are largely blowing smoke. They want to, in the eyes of startups, marginalize a potential substitute (smart VCs with their own networks and value add) and promote a complement (dumb money).

Now how does this all relate to the current environment, in which the COVID-19 market shock has clearly slowed down early-stage funding? The length and intensity of the slow-down is still of course an open question with all the uncertainties around how long quarantines/lock-downs will last, and the fact that many funds are sitting on cash that they still need to deploy; but it is certainly real. How should founders approach VCs? As a venture lawyer who doesn’t represent a single institutional investor – see: Relationships and Power in Startup Ecosystems if you want to understand why – my opinion from experience is that the correct approach for most startups lies somewhere in the middle.

I have seen “party round” culture result in so many blowups that it clearly is reckless and should be avoided. Even some of its most vocal evangelists find themselves back-tracking on the approach as the results play out in the market. But I’ve also seen the extremely negative consequences from becoming too dependent on a single VC or syndicate of closely affiliated VCs, which increases their ability to play power games on Boards and extract value that they otherwise wouldn’t have if the cap table were slightly more competitive.

Relationships matter, and it is unquestionably the case that some institutional investors truly are worth accepting a lower valuation, a larger “lead” check, and giving more control away to, in order to “partner” with them long-term. This is obviously the case in a bear market, but it’s also true in a bull market because even in bull markets no founder team ever knows when a crisis – personal or systemic – will slap them in the face. A VC with a sizable percentage of your cap table has “skin in the game” to help you through a crisis. A party round investor for which you are one of 40 investments is far more likely to sit out a crisis and play it safe.

That being said, you can still build strong relationships with VCs, and give them meaningful skin in the game, without being foolishly over-dependent on them. It is wise, if you have options, to include on your cap table a sufficient diversity of un-affiliated investors such that if one group becomes unreasonably “uppity” you have other supporters to turn to. Too much optionality turns into a party round, but some optionality is wise and valuable.

Clearly the startups that will have the easiest time in this crisis, however long it lasts, are those with enough cash in the bank to weather the storm. But for those who will need to enter the fundraising market in the next 3-6 months, without a doubt the competitive maximalists who’ve filled their cap tables with lots of small checks, and refused to let anyone participate in governance and build a relationship with the executive team, are going to be in for a rude awakening. They’re going to learn the hard way how “easy come, easy go” applies to early-stage fundraising.

Build meaningful, durable relationships with professional investors with the character and resources that can provide valuable insurance when an unpredictable crisis hits. Just ensure you’re well-advised throughout the process, so the “relationship” develops in a way that is balanced, and your company isn’t over-exposed.