Post Category → Texas

Luddites v. Tech Utopians: 409A and Legal

Background Reading:

TL;DR: Luddites pretend that technology can’t out-do them at anything. Tech utopians pretend tech can do everything. The truth lies in the middle.

In my sphere of the world, I interact with two profiles of people, both of whom I find somewhat obnoxious.

The first are luddites; often lawyers. These people cannot fathom the idea of clients wanting anything less than hand-crafted, white-glove attention to every legal matter. The compromises on quality and customization brought about by software and automation tools are an offense to their professionalism. They’ll walk you through 10 ways in which they can beat a piece of software, completely oblivious to the fact that 99.9% of the market doesn’t give a damn, if the software’s output is good enough.

The second are the opposite of luddites; what I’d call tech utopians, often young founders or engineers. To these folks, effectively everything legal professionals do is hand-waiving non-sense, charging hundreds of dollars an hour to fill in forms.  Build a simple automation tool, or DIY checklist for them, and their eyes light up; enraptured with how ‘smart’ they are for not ‘wasting’ money on legal services. And I happily admit to a bit of schadenfreude when they end up paying 10x later for cleanup, as part of their education in the value of legal counsel.

Luddites are in self-denial regarding how much of their work can actually be done quite well, and sometimes better, by technology. Tech Utopians are in denial about how much work still requires, and will require for a very very long time, highly-trained, highly-intelligent people who aren’t conflicted, and who can analyze and deliver things that even the most advanced technology cannot. And yes, those people are way more expensive than software.

The bottom 25% of most professions is probably dead in the water relative to software; think TurboTax and LegalZoom. As AI becomes more sophisticated, that will probably move up to something closer to 50%. This is quite visible in law as lower ranked schools (many of which are a racket) are getting sued by debt-saddled graduates who can’t find jobs, and the credentials of lawyers at well-paying firms edge up each year.  To some extent, it’s never been better to be an elite lawyer. It’s never been worse to be any other kind.

Tech-Enabled Lawyers

The truth about almost every profession, at least when you move beyond the lower rungs, is that technology is a supplement, not a replacement, for people. It’s a tool. And a very powerful one for those who can figure out how to leverage it.

E/N’s recruiting process is designed to systematically filter out luddites. That’s because, not only do I simply not have the time or desire to waste hours of my life trying to train them, but technology (automation, machine learning, communication tech, project management, etc. etc.) is so deeply integrated into our workflows that to add anyone who doesn’t ‘get it’ into the mix would cause a total breakdown. Before I look at emotional or analytical intelligence, or communication skills (all of which are important), I want to know what kinds of technology this person already uses in her/his life.

When lawyers from other firms ask how they might operate and scale leanly like E/N, my answer is as swift as it is depressing: “first, you have to fire half of your payroll.” They usually start laughing, until they see the dead serious look on my face. The legal profession is full of luddites, everywhere; even among the younger generation and in firms that service tech clients. And there’s no room for them in tech-enabled law firms. “Get it” or get out.

And yet with all of the technology that we leverage, I tell every single E/N client that we are not cheap, and never will be. Cheaper than our true competitors, certainly. And dramatically more responsive. But talent costs money.

409A: Trim that fat

When I wrote 409A as a Service: Cash Cows Get Slaughtered a few years ago, highlighting how eShares was using their own technology to trim the fat in an industry that (in my opinion) really was in many cases extorting startups, the response from the luddites was predictable. “Here are 10 reasons why you can’t automate a 409A valuation.”

Over the years, eShares as a platform has grown (as I knew they would), and many of our clients have been thrilled to take advantage of their service. Tech-enabled 409A; not fully automated. They recently published a blog post called The art and science behind an eShares 409A breaking down how automation is used in their reports, and how it’s not.

The future of professional services belongs to people who embrace technology and let it do what it does best, without diminishing the areas where human intelligence and creativity are superior, and will continue to be so for a very long time. Not tech-less. Not tech-only. Tech-enabled. 

Local v. Out-of-State VCs

Some things in life are certainties. The sun will rise tomorrow, you will be taxed for something… and startup ecosystem players across the world, outside of Silicon Valley and NYC, will complain about the lack of local VC capital, and the need for more foreign capital. Are they correct in complaining? I’m not going to answer that question. Too debatable, and the debate gets you nowhere.

What I am going to say, and I’m saying this as someone who manages a legal practice with visibility into a decent number of 2nd/3rd ‘tier’ ecosystems in the U.S., is that there are a lot of reasons to be optimistic about the overall trends in this area.

The Historical ‘Scarcity Culture’ of Local Venture Capital

Not just in Austin, but in many tech ecosystems that have a similar profile, there’s historically been a culture among the institutional investor community that directly reflected the scarcity of local capital, and of information about that capital. I will call this ‘scarcity culture.’ Trying not to come off as too judgmental, because all institutional capital plays a vital role in the business community, regardless of its approach, I would say that scarcity culture is largely summarized with the following statement:

“You don’t like our terms or our behavior? What can you do about it? What alternatives do you actually have?”

Does this mean that all local VCs outside of the densest markets think that way? Of course not. But it is definitely there, in a variety of ways.

Anyone with a broad enough visibility into American venture capital knows it is an absolute fact that California VCs are generally ‘friendlier’ than the VCs of any other ecosystem. By ‘friendlier,’ I mean that they are OK with higher valuations, they are more transparent in their intentions, and they tend to show significantly more deference to a founder team in terms of providing coaching/opportunities for growth as opposed to an early pink slip.  Why is that?

Is it something in the water? The weather? Have they achieved a new level of enlightenment? Hell no. California VCs have the same job as VCs anywhere else: to make money.  The answer lies in one very simple word: competition. And increasingly over the past few years it is magnified by one more factor: increased transparency through technology and decreased friction in networks. 

Competition and Reputation. 

Let’s use an analogy here.  Do you think that restaurant service is better or worse in dense urban environments relative to small rural areas? Obviously it’s better. There’s more competition.

Do you think the existence of Yelp, and the ability of restaurant goers to (i) easily find information on the past experiences of patrons of a specific restaurant and (ii) easily express their own experience about those restaurants, has improved or reduced the quality of restaurant service? It obviously has improved it. There’s a million times more transparency, which dramatically raises the reputational stakes.

In an environment where a quality founder team can, if they don’t like one particular set of VCs, walk almost literally across the street and talk to 10 more, investors have learned (rightly) that to be an asshole is to step right into a massive adverse selection problem. Combine a truly competitive market with inter-connected networks where reputational information flows freely, and you have a system that naturally corrects for bad behavior.  The really good companies, the one’s that everyone would want to invest in, don’t have to put up with anyone’s nonsense; and they do their homework. 

Contrast that with ecosystems where only a handful of investors, many of whom collude with one another, are available for companies that need serious funds, and you have a very clear explanation for why California capital is ‘sunnier.’  California VCs are more “founder friendly,’ because their circumstances make founder friendliness an almost essential requirement for deal flow. Most assholes can’t even survive in that environment, so it selects for ‘nicer’ people.

I am not saying that west coast money is all cotton candy and rainbows; nor am I saying that non-SV local VCs are all difficult to work with. But broadly and relatively speaking California VCs tend to be much easier for a founder/management team to get along with. It is also no surprise that the rise of industry/vertical-focused VC and VC ‘value-add services’ has come out of California. They’ve got to find a way of differentiating themselves in the noise.

Transparency and Friction.

A decade ago, if you needed to connect with X person for whatever reason – to diligence an investor, to connect to an investor, to find out some piece of information – you faced enormous opacity in finding a path to doing so. This opacity added friction not only to connecting with people far outside of your personal network, but also to obtaining information, including reputational information, about market players. Information is essential for separating marketing/branding from reality.

Blogging is marketing. Twitter is marketing. Talking on panels is marketing. Free office hours is marketing. That free beer at the ‘get to meet investors’ meet-up is marketing. This should be obvious to smart CEOs. Yes, this blog is marketing. Calling something marketing doesn’t mean it’s false; it just means you’re acknowledging the incentives behind it. And that you need a mechanism for verifying what you’re being told.

My method in biz dev is simple: “here’s a list of my clients. reach out to any of them, and don’t tell me which one. Ask them about our rates, and our responsiveness, and the independence of our counsel. I welcome diligence.”

Today, if I run into a set of founders who are talking to VCs, whether they are clients or not, I say “Here is a list of their past investments. Get connected to the founders of those companies, and start asking questions. And don’t tell anyone which ones you are talking to. Don’t treat any single ‘review’ as gospel, because it is a one-sided story. But look for patterns.” For a team that is even mildly good at networking, that is a fairly straightforward task. LinkedIn does 80% of the work for them by letting them know exactly who in their existing network, whether they’re local or not, can connect them to their target.

Tools like LinkedIn, AngelList, Facebook, and Twitter, and the way in which they eliminate huge amounts of friction and opacity in networking, have done two game-changing things for founders: (1) they’ve made expanding their networks beyond their local ecosystem 10x easier (I didn’t say easy, I said easier), and (2) in doing so, they have made finding accurate reputational information about market players 100x easier. That ease of accessing accurate information influences the behavior of investors in exactly the same way that Yelp influences the behavior of restaurants.

In an opaque market in which influencers can control access to people and information, you can reap the benefits of being an asshole without facing many of the costs. Today, the transparency brought about by modern tools and networks has made the costs of bad behavior 10x higher. Technology makes technology investors ‘nicer’ by opening up access to accurate information on market players. Knowledge is power. 

Improving Local VC. Accessing out-of-state VC. 

Thinking of this issue broadly with the above concepts: improving transparent access to accurate information, removing friction in expanding networks, increasing competition, I think we can arrive at some useful ideas for both improving the local investor environment in non-SV markets, and in increasing the flow of capital between markets; beyond the “great companies attract great capital” truism that rightfully causes eye-rolls among founders.

1. Founders/management need to talk to each other more, in places that aren’t controlled by the investor community. 

Information flows most freely when the consequences of sharing it are minimized. You better believe that in some markets where key players serve as gatekeepers (see: Gatekeepers and Ecosystems) the threat of being black-listed somehow for speaking honestly is real. You will never get accurate market information on blogs, on twitter, on panels, or in highly public events where anyone and everyone is watching.

To use Brad Feld’s categories: there are entrepreneurs, and then there are “feeders,” which sort of means everyone else. Events and communities where the whole ecosystem is invited are great. But that entrepreneur v. feeder divide is crucial, and there need to be ways for entrepreneurs to share information with each other, confidentially and alone.

That is the best way to create the following causal chain: (1) bad market behavior -> (2) information shared to broader entrepreneurial community -> (3) adverse selection for bad market player -> (4) correction to behavior.  You get along much better with the VC community when, instead of moralizing about their tactics and behavior, you try to understand their goals and their incentives; and find ways to align them with yours.

2. Outreach to foreign capital needs to come from people who don’t benefit from a scarcity/opacity environment.

Do not expect for a second that market players who benefit from scarcity of local capital and opacity of information will improve the environment for you. In a variety of ecosystems, I have seen circumstances in which local capital deliberately tries to keep out-of-state capital off of a cap table if it is not willing to enter on their terms. If a founder team builds local support and then themselves builds independent relationships with out-of-state capital (directly or via local relationships), that will create very different dynamics relative to a situation in which their local capital syndicates with its own existing out-of-state syndicate partners.

Is building those out-of-state relationship easy? Of course not. But it needs to start early. The companies that successfully receive out-of-state participation in their Series A round often were building those relationships at seed.  And the best intro to a particular investor is through a founder that they already invested in, so local founders who’ve accepted out-of-state capital are vital to encouraging that capital to engage more local companies. Once a foreign VC has made an investment in a city, it is a lot easier for them to look at others.

The angel v. institutional capital divide, highlighted somewhat in “Protect Your Angel Investors” is important here too. True angel investors – not the ones that behave essentially like micro-VCs, but the ones who are playing with their own money and who are really in it for more than just a return – typically behave very differently from institutional capital. They are usually more patient, more attached to the founder team, and usually aren’t laser-set on a “10x or bust” mindset that institutional investment often brings. Angel investors with broad networks can play a huge role in encouraging out-of-state capital to enter new ecosystems.

Just please for all things holy ignore any set of lawyers pretending to provide ‘special access’ to out-of-state investors. There is a hierarchy of paths to investors. If lawyers are even on it, they are near the bottom.

3. De-risk long-distance investment by improving communication.

If I’m an investor deciding whether to invest locally or make a bet on a team 1,000 miles away, I see substantial additional risk in the latter simply because of the added friction in communication. This is particularly important at seed/Series A, where feedback loops between investors and founders are more important. Think of ways to signal to long-distance investors that you will actively remove that friction.

Videoconferencing, well-done regular investor updates like through AngelSpan, committing to flying to meet-up in person regularly, are a few ways to do this. If entire companies can run with remote teams, leverage similar mechanics/tools to make long-distance startup investment seem natural and logical.

4. Reduce search costs. Successful curation is king. 

Finally, while communication issues often make long-distance investment at least seem difficult, you should never ignore the fact that to any investor, simply vetting out-of-state companies is much harder than vetting local ones. Most institutional investors build in various filters and qualification mechanisms into their pipeline/deal flow, and they often break down when looking at companies that are mostly outside of their usual network.

So creating credible, successful curation mechanisms to reduce the ‘search costs’ of institutional investors exploring non-local markets is essential. The obvious answer here is, and has been, accelerators; at least to the extent that accelerators aren’t beholden to particular local funds (in some markets, they are). The most prominent accelerators are playing extremely important roles in connecting companies in one market to investors in other markets, because those investors trust that the accelerator has done a significant amount of pre-qualifying for them. In fact, this curation dynamic is part of the core value proposition of accelerators in the first place.

Another obvious answer is angel investors with prominent personal brands. As angel investors develop broader reputations for selecting winners, out-of-state institutional capital can leverage them to reduce the search costs of exploring other markets.

So, is raising a Series A outside of Silicon Valley and NYC really hard? Absolutely. Then why the reason for optimism? Because every single variable/dynamic mentioned above is improving, and at an accelerated pace. Founders are finding each other and communicating directly, sharing accurate information about the investor community and other market players; aided by modern networking and communication tools. Local angels and entrepreneurs are actively using those same tools to expand their networks far beyond their local ecosystem. Tools for long-distance communication and investor relations are maturing. And accelerators and prominent angels are increasingly becoming curation mechanisms leveraged by institutional investors to reduce search costs and explore new markets.

We are certainly seeing all of this happening at an increasing rate in our work in the market. As additional funds that are more comfortable operating in the new environment pop up, and as geographic barriers are reduced for capital flows, the more established players are increasingly more concerned with their brands and reputation. Instead of a “scarcity culture,” an open, transparent market culture favors investors that deliver real value and build durable, authentic brands.

Raising local and out-of-state institutional capital, and ensuring you’re working with good people, is still extremely hard if you’re not in a top-tier ecosystem. And speaking as ‘just’ a lawyer, I don’t want to minimize that fact in any way.  But the truth is that it’s also never been easier, and the core trends suggest it will keep getting better. 

Founder Education

TL;DR: Accelerators have emerged as elite universities of sorts for tech entrepreneurs. But they offer a bundled value proposition at a price (in terms of time and equity) that doesn’t work for everyone. For those teams in need of just the educational aspects of an accelerator, other (quality, but lower cost) offerings are starting to be developed that should be considered.

I’m a huge proponent of curation and leveraging the knowledge of trustworthy domain experts to avoid burning time; time that could otherwise be spent running a company.

The value of curation in the lives of founders is perhaps reflected best, above all else, in the rise of accelerators. Accelerators’ core value proposition to founders is that, in exchange for (i) several weeks of their time, (ii) an equity stake, and (iii) rights to invest in future investment rounds, founders in accelerators gain virtually immediate access to significantly curated resources: investors, mentors, other founder teams, prime office space, educational content, etc.

And on the flip side, great accelerators are able to attract quality resources by promising the people who provide those resources access to a curated set of startups; saving them time from having to sort them out in the general marketplace.

Of course, the value of those resources and their curation varies wildly depending on the quality of the accelerator. Top accelerators have proven invaluable to many young, inexperienced founder teams who’ve saved countless time searching, networking, vetting, etc. by tapping into an accelerator’s network and resources. Lower quality accelerators, however, are often a time suck, and much like the “Top Startups to Watch” lists we all see get thrown around, can serve as a damaging and distracting vanity metric.

But as much of a fan as I am of great accelerators, the reality remains that accelerators offer a bundled value proposition. And not every founder team needs, or is willing to ‘pay’ for, the entire bundle. Some founders have already arrived at a successful business model showing strong traction, and are good in the advisor department, but just need connections to Series A investors.  Other teams are well-funded, and already have their own office space, but could really use some guidance on the ‘fundamentals’ of recruiting, managing a scaling company, etc. It shouldn’t surprise anyone if resources are developed in startup ecosystems to address these types of companies for which a typical accelerator isn’t the right fit.

Every now and then I use SHL to spread awareness about new resources in the market that I feel are really adding something differentiated and high value for founders relative to what’s currently available. Years ago I wrote about Clerky and how it filled a void in the market of startups that just need a super-fast, totally standard incorporation and corporate organization, and due to capital constraints are willing to go through it without a lawyer. I also wrote about how eShares was using a SaaS model to liberate early-stage startups form burning money on 409A valuations. I later wrote about how services like Bad Ass Advisors can help companies connect with specialized advisors/mentors beyond the limited roster of people available in their local market.

Today, I’m writing about another topic: Founder Education; meaning how founders can get access to the wisdom/pattern recognition of people who’ve observed dozens, or even hundreds, of startups. It includes best practices on topics like starting a company, finding advisors, finding product-market fit, using advisors, compensating people with equity, targeting investors, understanding metrics, building sales/distribution channels, etc. etc. Books and blogs are great, but they can only go so far, and sorting gold from garbage gets hard. Top accelerators have developed internal curriculums for these sorts of topics, but (remember) they come bundled with a lot of other resources, and at a price, that don’t necessarily work for all companies.

In Austin, I was recently introduced to Founders Academy; an educational curriculum designed for tech founders. It’s run by Gordon Daugherty, a very well-known and respected (including by me, and SHL readers know I’m jaded from experience) startup advisor in Austin who’s had a front seat for some time at one of Austin’s best known accelerators, Capital Factory. Gordon’s built Founders Academy into a packaged, structured curriculum for new tech founders; offered both as a set of online videos that you can buy, and also as an in-person course (taught by Gordon over a few days) that founders can sign up for.

I got some feedback from a few teams that participated in the in-person course, and they all said it was extremely valuable for the price of a few hundred dollars.  I’ve reviewed much of the material myself, and have also interacted with Gordon enough, to say that he knows what he’s talking about, and because his background is in Austin / Texas, his curriculum will resonate well with founders operating in markets that aren’t Silicon Valley.

As I’ve written about before on: Bad Advisors: The Problem with Localism, many tech entrepreneurs operating in second and third-tier ecosystems run into a serious problem when they limit their pool of advisors to their city’s geographic boundaries: they get bad (sometimes really bad) advice. Founders Academy, and other programs like it (if you know of them, leave comments please) thankfully help solve that problem by scaling the wisdom of domain experts (advisors who aren’t charlatans) in ways that are more structured and digestible than just blog posts or books.

Education means leveraging the wisdom of others, so you can avoid the mistakes that they made. For tech entrepreneurs who don’t have time or money to waste, the right kind of education is invaluable. And while top accelerators have emerged as the elite universities of the tech startup world, they clearly aren’t for everyone. It’s great to see quality educational resources popping up to fill the void.

p.s. Like Clerky, eShares, and Bad Ass Advisors, I don’t have any ownership interest in Founder Academy. The mention was entirely earned.