Founder Burnout and Long-Distance Thinking

TL;DR: “Life ain’t a track meet; it’s a marathon.” – Ice Cube

Related Reading: Burnout, Depression, and Suicide

I’m prone to deep thinking about life. It’s why I quit the honors program in a great business school within weeks of entering college, and switched to Philosophy (adding Economics later). Best career decision of my life. No offense to the business school grads out there.

I’ve always had this feeling that people devote far too much brainpower toward things that ultimately amount to nonsense, and yet things that are infinitely consequential – like what you want to do in life, where and how you want to live, whom and when to marry, whether and when to have kids – people seem to either follow a script, or just let their surrounding culture/peers push them in the direction of the current zeitgeist. And the truth is, the zeitgeist doesn’t give a shit about you. Slow down, and think it through. You get one shot.

And instead of asking your friends, ask people who’ve gone the distance. It’s well documented culturally / sociologically that spending all of your time with people your own age leads to all kind of mental dysfunctions and myopic thinking. The only way to get real perspective is to listen to other perspectives, and that means age / generational diversity.

A lot of the advice out there on founder burnout amounts to a kind of checklist on health and wellness. Let’s go ahead and get that checklist out of the way:

  • Sleep – Don’t delude yourself into thinking that pulling all-nighters and not hitting your 7/8 hour a day quota will make you more productive. It won’t. The data is clear.
  • Exercise – Same. Go for a run. Lift some weights. It’s not time wasted. Again, it makes you more productive.
  • Eat well – Eat shit, and you’ll feel like shit. Read up on carbohydrates, insulin, inflammation, and energy. You’ll learn some things.
  • Delegate – Build systems, and then hand those systems over to other people. If you can’t figure out a way to scale your skills, you will fail at life and at work.

But in my opinion, and from what I’ve observed among certain entrepreneurs, there’s a deeper, longer-term issue at play regarding founder burnout (and life burnout in general) than just getting overworked and not taking care of your body. The best way I can explain it is using some old school philosophy concepts: higher and lower pleasures.

Speaking very generally, lower pleasures require constant replenishment, because the feeling they generate just doesn’t last. They’re the “simple carbs” of life. Sex, drugs, and rock n’ roll are the typical go-to’s when someone wants to explain lower pleasures, but lots of cleaner forms of activities in life fit this category. Once they’re over, all you’re left with is a memory, and a desire for another one.

In contrast, higher pleasures have a kind of lasting effect. They have staying power and can bring satisfaction to life even when you’re not at the moment “doing” anything about them. Long-term friendships, love, family, and a sense of meaningful (not just financial) achievement are all classic examples of higher pleasures. They can be entertaining (or the opposite) and take up your time, but that time is a kind of investment toward building something that carries you forward in life, and is still there when you’re in your 40s, 50s, 60s, and later. David Brooks wrote a good op-ed called The Moral Bucket List that is worth reading.

The deeper kind of life burnout that goes beyond health/wellness results from years, or even decades, of failing to build durable “higher” pleasures into your life. You can ensure that you’ve slept enough, exercised, eat well, and have built a great management team, and yet at 40, 45, 50, find yourself sipping martinis on Christmas Eve, alone, or with someone who means absolutely nothing to you. That end-result really burns, because there’s no checklist for resolving it. Fail to build/invest into things in life that last and will help you really go the distance, and it can eat you alive in the long run.

When asked by young law students about how to vet law firms for employment, I’ve always said to look at the older partners, and watch/listen very closely. Look for divorces, kids in therapy, anger management issues, drug addiction, alcoholism. In the legal profession, and in all areas full of high performance personalities – including entrepreneurs – they’re everywhere. People who treated life like it’s a track meet – narrow your vision and run as fast as you can – when it’s really a much longer, much more intricate marathon.  Rock stars in their earlier years, but they failed to go the distance.

So my personal advice to ambitious entrepreneurs about preventing burnout long-term is, yes, sleep, exercise, eat well, and delegate, but also build a real life, not just a company. Emphasis on the word build; as in, activities that contribute to relationships and things that will be there tomorrow, and next year, and a decade later, when you’re a different person, with different priorities. Look ahead, and plan for the distance.  Most of the people around you telling you to just “keep hustling” care more about your stock than they do about you personally, or are themselves ignoring how long the marathon is.

Look for mentors who’ve built their own companies, but while maintaining a sense of balance (even if loosely defined).  Even if zen-like balance isn’t really achievable, the simple act of trying hard to achieve it will ensure you land somewhere sustainable. Like a speed limit, you know you’ll break it, but it’ll still help pace you.  

Think things through, and spend some of your time really building a life, apart from your company. The building may take longer than just narrowing your goals and running as fast as you can, but the end-result will be something much more durable. 

Lawyers and NPS

TL;DR: Net Promoter Scores provide a clear, simple opportunity for law firms and clients to cut through the obfuscation and marketing nonsense of the legal industry, and understand who really delivers.

From my earliest days of law school, I knew I was going to have a little trouble relating to my chosen profession. Virtually all of my peers were devoting large amounts of their non-class time to something called “blue-booking,” which means learning a bunch of arbitrary rules for proper formatting of citations in legal journals, and “spotting” the errors in a long list of citations; a kind of hazing ritual to get onto a journal. I simply could not get over how the entire thing looked like a spectacularly boring, unproductive waste of my time. I was the only law student in my class at Harvard that I was aware of (I’m sure there were a few others) who never even applied to a journal or law review, and never touched a blue book.  I’ve done alright.

This “WTF are you all doing?” feeling carried on post law school. Moving into a large law firm setting, it was absolutely breathtaking how backward the workflows of lawyers were, and how powerless law firms, as institutions, were to change it. Why are they powerless? Here is my core diagnosis for the “problem” of most large law firms: they are not really firms. Or perhaps better said, no one is really in control. The vast majority of large law firms are decentralized, weakly unified collections of fiefdoms, each controlled by a partner who isn’t truly accountable to other partners, or a central hierarchy. Within a “firm,” a small group of people may have a great idea, or tool, for implementation, but absolutely zero ability to get it adopted firmwide.

Combine that with a power structure concentrated in the hands of (usually) traditional 50 and 60 year olds, and the fact that you usually have dozens of totally unrelated practice groups with independent needs, incentives, etc., and you see that the inertia and inefficiency of law firms is structural and cultural. People who blame the billable hour are focusing way too myopically on one thing, and ignoring the broader, deeper problem. Most law firms are simply too large, too broad, too decentralized, and too lacking in institutional brand power relative to the personal brands of their old school partners to implement needed changes. The only solution, in many cases, is a reset button.

So joining and building out a small boutique firm was my opportunity for a reset button, and I got it, along with an AMEX card to buy what I needed, without having to ask anyone for permission. Starting with a clean slate, and supported by a handful of senior partners with the right mindset, I was able to build a law practice that cut out all the bullshit and delivers what good clients want. What do clients really want, btw? Here are a few examples of what they don’t want:

What isn’t bullshit?

(i) awesome lawyers with specialized expertise,

(ii) who are responsive and DON’T LOSE E-MAILS,

(iii) provide real strategic insight and not just paper pushing,

(iv) are transparent about costs (w/o BS-ing that legal can be cheap), and

(v) can demonstrate their consistent efficiency and quality.

In building out our firm, I searched for a single, objective metric, minimally exposed to BS, for building accountability and clarity around our mission of delivering the above, and I found it: the Net Promoter Score. Our most recently calculated NPS is 77. Apple’s, Amazon’s, and Costco’s NPS range from the 70s and 80s, depending on where you check. Is it as high as we want to be? No. Every year we learn more, and iterate as we scale sustainably. The beauty of NPS, in addition to its simplicity, is how every client’s voice counts. Many law firms have built their brands around the 1% of their clients, with the complaints about slowness, low quality, conflicts of interest, costs, and other issues of the 99% drowned out.

NPS imposes a level of transparency that punishes anyone who isn’t disciplined with what clients they take on, to ensure consistent quality. It actually forces you to focus, because the needs of an unfocused client base are so broad, that you can’t deliver consistency. NPS punishes bloated, unfocused, overly extended scale. 

While we don’t have the structural problems of large firms, we definitely deal every day with the training, recruiting, technological, cultural, and business development challenges of any high-end service provider that handles complex, high-stakes human (as opposed to automated or manufactured) services.  But what matters most is that we have a score for today, for last year, and for next year, to gauge whether we are doing our job, instead of the 100 other things that other people love to talk about, but are not actually our job.

And what I’ve found most interesting, and compelling, is how when you focus your strategy around NPS, the competitive advantages you build are durable. So many of the ways that law firms try to compete in the market can be easily bought: a piece of software, a key lawyer with a big book of business,  a sponsored event where influencers get together, a side deal to a market player in exchange for referrals. But by being purchasable, they’re also easily replicable by anyone else with money.

Delivering scalable, consistent, long-term quality – what results in a high NPS score – is infinitely more complex and time consuming to build, especially when you’re dealing with lawyers. There’s no main “secret” behind what we’re doing. It’s 1,000 little insights and implementations, compounding daily.

My advice to lawyers contemplating starting their own firms is to always, first and foremost, get absolute clarity around (i) what clients they want and don’t want, and (ii) then ask those clients what they want; then start building, and collect your NPS regularly. Focus, and the ability to learn and iterate quickly, is the core strategic advantage of the boutique law firm ecosystem.

And my advice to potential clients when diligencing lawyers is to start out with one question: “What’s your NPS?”  The answer, even if it’s not a number, always speaks volumes.

More Tech Startups are LLCs

TL;DR: Years ago, it was an “obvious” decision for almost every tech startup founder that they would form their company as a “classic” C-Corp designed for venture capital investment. As entrepreneurs have become far more aware of the downsides of VC money with very high-growth expectations, and the diversity and number of tech investors comfortable with LLC investment grows, that is less the case today.

Background Reading:

If you have spent almost any time reading about the basics of startup legal issues, you know that Delaware C-corps are the default organizational structure for a “classic” tech startup (software, hardware) planning to raise angel/VC money and scale. I’m not going to repeat what you can read elsewhere, so I’ll summarize the core reasons in 2 sentences:

Delaware because DE is the “english language” of corporate law and all serious US-based corporate lawyers (and many foreign lawyers) know DE corporate law.  C-Corp largely because (i) VCs have historically favored C-Corps for nuanced tax and other reasons, and (ii) virtually all of the standardized legal infrastructure around startup finance and equity compensation assumes a C-Corp.

However, times are changing. Over the past few years, we’ve seen a noticeable increase in the number of emerging tech companies that, despite knowing all of the reasons why startups favor C-Corps, deliberately choose to organize their company, at least initially, as an LLC. To be clear, C-Corps are still the norm, by far. But the C-Corp / LLC mix has, for us at least, moved maybe from 95/5 percentage-wise to about 85/15. That’s an increase worth paying attention to.

The growth in interest around LLCs has very little, or really nothing, to do with legal issues, in the sense that nothing much has changed about LLCs or C-Corps to drive people in one direction or the other.  The main drivers, from our viewpoint, are:

  • Many tech entrepreneurs no longer view venture capital as an inevitability in their growth path, and have grown skeptical of the traditional “growth at all costs” mindset found in many startup circles; and
  • An increasing number of technology investors are growing comfortable with LLCs.

Profitability is now a serious consideration among tech entrepreneurs. 

C-Corps have 2 “layers” of tax: corporate-level tax, and then tax at the shareholder level. LLCs don’t have a corporate-level tax, and therefore have only 1 layer. Speaking in broad terms, this “disadvantage” of the C-Corp structure has not deterred tech startups for one simple reason: the corporate level tax is on profits, and many tech startups don’t intend to be truly profitably any time soon. Achieving very fast growth through reinvestment of any ‘profits’ has been the dominant growth path among tech entrepreneurs, which means no “profits,” which means being a C-Corp doesn’t really result in more tax.

However, the zeitgeist among startup ecosystems is shifting from “focus on growth, and raise VC” to “unless you’re absolutely positive you’ll raise VC, keep your options open.” Keeping your options open favors starting out as an LLC, because converting an LLC to a C-Corp is way easier than converting a C-Corp to an LLC. The reason for that is simple: the IRS welcomes you with open arms if you choose to move from 1 tax layer to 2. But going in the opposite direction costs you significantly.

As more tech entrepreneurs take seriously the possibility of building a profitable, self-sustaining business, their interest in starting their companies as LLCs is growing, because building a truly profitable business as a C-Corp is much more expensive (tax wise) than it is as an LLC. Many angel investors, and also strategic investors, are comfortable investing in LLCs, particularly under a convertible security structure that doesn’t immediately result in equity holdings.

So starting as an LLC allows you to build your company, and even raise some early capital, while letting things develop to see if you’re really building a business that needs conventional venture capital (and then convert to a C-Corp), or if you’re building one that may instead become profitable and distribute profits to investors (stay an LLC).

VCs are also growing more comfortable with LLCs.

The conventional line given for why VCs “must” invest in C-Corps is that the “pass through” treatment of LLCs can result in various negative consequences to their own investors (LPs), many of whom are tax exempt – so the C-Corp structure prevents the tax problems. However, more sophisticated VCs have realized that in most cases this problem is quite fixable. They can set up what’s often called a “blocker corp” that eliminates the possibility of pass-through income negatively impacting their tax-exempt LPs. Problem solved. It’s not that hard to do.

Truth be told, a lot of VCs still don’t want to mess with LLCs. But at this point it has more to do with inertia and a desire to minimize their own legal bills than any real legal issue. Also, most VCs are only looking for companies in a high-growth track where any net revenue will be reinvested for growth (no corporate profits, no corporate tax), so they are selecting for companies for whom an LLC structure isn’t really that appealing.

But not all VCs think that way. In fact, the types of investors putting money into tech startups has been diversifying significantly. Angel syndicates have grown in size, seed funds have multiplied and grown bigger, with larger checks. And strategic investors now invest very early. Many of these groups are far more comfortable with LLCs than “classic” VCs, because they aren’t as constrained in the types of companies they can invest in.

If you are an LLC tech startup, you need tax counsel.

If you are a tech startup that wants to be an LLC, realize that while LLCs may save you taxes, they will not save you legal fees. Equity compensation, particularly to employees, is much more complex under LLCs, and requires the oversight of true tax lawyers. It is not something to be handled solely by a “startup lawyer.” Any law firm working with LLCs should have access to tax specialists, and if they don’t, that is a red flag.

Also, as startups move from a uniform growth path to one that considers a wider variety of sources of capital (angel, non-traditional seed, strategic, private equity, debt, royalty-based, etc.), they need to accept that the standardization found in conventional Silicon Valley-style fundraising is simply not a possibility. The huge push to standardize investment documentation into templates that can be almost automated stems from the “billion or bust” mindset of classic VC-backed startups. In that world, everyone is a Delaware C-Corp. Everyone is trying to be a billion-dollar company that will eventually get acquired or go IPO. All the angels talk about the same things on twitter and are comfortable investing on the same docs. So just automate a template, plug in some numbers, and focus on growth.

But in a world where everyone isn’t a Delaware C-Corp; everyone isn’t on the same “billion or bust” growth path, and there is far more diversity among companies and investors, the conditions for heavy automation and standardization simply aren’t there, and likely never will be. It requires real financial, tax, legal, etc. advisors to handle real complexity, while right-sizing it for the stage and size of each particular business.

The truth is that outside of a few large startup ecosystems, there has always been much less uniformity among financing structures. Software engineers – frustrated with their inability to force everyone into uniform documentation that can be automated – have criticized this reality as backward and just needing to “catch up,” but to people on the ground it’s been pretty obvious they’re just hammers screaming at everyone to become a nail. More entrepreneurs are no longer comfortable being pigeon-holed into a one-size-fits-all growth path or legal structure, and long-term that’s a good thing for everyone.