Burnout, Depression, and Suicide

Background Reading: Founder Burnout and Long-Distance Thinking 

This is going to be another personal post; less about how to close a financing or avoid legal issues, and more about the bigger fundamental issue of life outside of work. Because if you think what happens outside of work doesn’t heavily influence what you achieve at work, you’re clueless. Please move onto another SHL post if you want Startup/VC law advice.  This post is prompted by the very unfortunate passing of Anthony Bourdain, whom I admired as a voice of authenticity in a world that sterilizes and bullshits far too much.

Depression and suicide are two things with which my bloodline is far too familiar. Since I was a young kid – watching family members lock themselves in rooms for days and weeks in the dark, and openly discuss swerving their car into oncoming traffic, sometimes while I was in it – it’s been at the top of my mind.

Despite my many faults – my wife of 10 years is always happy to provide a list – one thing I know I’m good at is being observant. I watch people very closely, and pick up on patterns and subtleties that others miss.  As the old saying goes: the wise learn from the mistakes of others, the smart learn from their own mistakes, and fools never learn.

Another thing I’m particularly fond of is what I call asking the “meta question,” meaning trying to separate symptoms from the disease, and talk about the root cause of something. Because far too often people get caught up with trying to band-aid the symptoms of something, without digging deeper and probing into fundamentals.

What’s absolutely crystal clear is that suicide and depression are way up in America. It is clearly a paradox, given that on many objective metrics, life has never been better: life expectancy, technological advancement, overall wealth, homicide/major crime rates, gender equality, etc.

The standard reaction to this rise in depression/suicide is to focus on mental health. If we just had more infrastructure for affordable therapists and anti-depressants, all would be better. But that obviously misses the bigger historical point. Life was, on many levelsway harder even just 50 years ago, and we didn’t have an army of public therapists then; yet depression and suicide were less prevalent. Clearly there is a meta issue here worth discussing.

To share my thoughts and observations on the topic, I’m going to first list out a few concepts that I’ve picked up over the years from reading, education, having good conversations over coffee, etc.:

Maslow’s Hierarchy of Needs – This is the idea that as peoples’ more physiological needs are met (shelter, food, etc.) and become less of a top-of-mind concern, their psychology shifts to prioritize “higher” needs, like love, belonging, art/beauty, etc.  People who grow up in more stable, loving environments (or societies) tend to be more open, creative, and communal, but that can also result in being more sensitive and emotionally vulnerable.

Specialization v. Generalism – Economic development inevitably leads to human specialization. People in rural communities are often decent at a lot of things, and more self-reliant, because they have to be. They’re also poorer. People in advanced markets tend to have much narrower, specialized skillsets, which they then sell in the market to earn surplus income to buy everything else.

Grit – The idea that exposure to hardship/struggle can build mental resilience, in the same way that exposing muscle to pressure makes it stronger, as long as it doesn’t go so far that things start to break. Moderate stress is good. Too little or too much is bad.

Dopamine v. Serotonin  – D and S are neurotransmitters. Without getting too bogged down in details that I certainly will botch, D is largely the “desire/drive” brain chemical. Heavily involved in addiction. Serotonin is heavily involved in calmness, satisfaction, a feeling of fulfillment. D and S have a tension with each other. If D overruns things, S decreases, which leads to depression.

Higher Pleasures v. Lower Pleasures – In the way that complex carbs are longer-lasting while simple carbs are often tastier but shorter-lasting, lower pleasures tend to be activities in life that are thrilling, fun, and even memorable, but don’t have much of an on-going positive effect. Lower pleasures drive dopamine. Higher pleasures, on the other hand, tend to be less thrilling, and in specific moments may actually be difficult/painful, but they have significantly longer-lasting positive impacts. Lower pleasures tend to cost you mostly money. Higher pleasures tend to cost you mostly time, but increase serotonin.

Traditional Culture v. Market Culture – Culture is largely the set of narratives and values that swirl in our brain to tell us how we should live, our role in the world, and the underlying purpose/meaning behind it. Many moderns dramatically under-appreciate the complexity and nuance in how culture plays into life satisfaction and progress.

Without culture, humans are just advanced monkeys. Traditional culture is the accumulation of centuries of slow-changing values and life-structures interacting with history, human psychology, social dynamics, etc. Market culture is the result of marketing/advertising messaging, often informed by PhDs in psychology and neuroscience, nudging people to engage in activities that ultimately maximize economic growth for someone.

Bottom-up Organic v. Top-Down Theoretical – There are two ways that cultural values, systems, and ideas in general emerge. A bottom-up “organic” approach starts from the ground, interacting with all the nuances and variables of reality, and iterates “upward” over time to arrive at an equilibrium.  A top-down structure starts with logic or theoretical principles, focusing on a kind of abstract consistency, and then imposes itself “downward” on reality. Organic emergence is messy, iterative, and often slow. Top-down is “cleaner” and more consistent, and usually faster. But also more prone to extreme errors. Traditionalists (at least those who aren’t dogmatic) tend to favor organic emergence of ideas. Intellectuals tend to favor the top-down.

Individualism v. Communalism – The free market pushes individualism as a primary value, because it maximizes economic growth. The more differences we can parse out among people, slowly nudging them to like different things, pursue different paths, the more things we can sell to them. It may feel like “discovering yourself,” but there’s a lot of outside nudging involved. Communalism, on the other hand, emphasizes similarities and long-standing histories between people. It’s driven by more traditional value structures, which focus less on peoples’ economic outputs, and more on their deep relationships to one another. It also is more constraining on individual freedom/choice.

Age-Mixing – Somewhere along the way, society got the idea that it’s better for everyone if people of the same age spend all of their time with each other. I suspect industrial-age schooling, and the efficiencies of standardizing education, are partially at play. Yet the evidence is clear that age-mixing produces significantly better outcomes on a psychological level. When you age-mix, older people (including older children) learn responsibility and empathy, and how to teach the younger. They also feel more “needed,” which gives life a sense of meaningful purpose apart from their market value.

And the younger benefit from the longer-term perspective of people who’ve “been there” and know how life progresses, instead of just being focused on immediate wants/needs. When people fail to age mix in their lives, they tend to be more hierarchical, competitive, myopic, and neurotic.

Ok, that’s a lot, and it took a while. But hopefully at least some of the concepts were enlightening. Now, using those concepts, here are my own personal observations/thoughts from my own life, my family’s history, and observation of others regarding the “meta” question of why society is so much more depressed and suicidal:

Affluence has taken away a lot of the hardship and struggle that once was a defining feature and motivator of people’s lives. Obviously, this is not necessarily a bad thing. I know so many people today whose life largely boils down to specialized work and leisure. They do one narrow thing that someone pays them for, and they buy everything else, so that they have “free time” to do things they enjoy; which usually involve seeking entertainment in the market. Specialization obviously makes people wealthier. But is there a point beyond which it makes people less happy?

Now you can order any meal you want on Uber Eats, and it’ll be delivered right to your door. That’s fantastic. It’s efficient. But what if the act of cooking, and even the act of picking out ingredients has some deeper psychological benefit that we missed? Now we can Lyft or drive to wherever we want, but what if the act of walking does something for us that we missed (and I don’t just mean burn calories)?

Market economics (and culture) says to specialize. Only do what has the highest market value, and you can just buy everything else. But traditional culture says hyper-specialization makes you fragile. You may become wealthier, but you also become less self-reliant and therefore more dependent on the market. And the idea that everyone should just do one narrowly defined thing, and then seek “entertainment” the rest of the time, is a speck in humanity’s evolutionary history.

Is the person who works their own garden and cooks on the weekends  just wasting their time on inefficient activities? Should the person who works on their car in their garage just stop wasting time and send it to a mechanic? Maybe. Or maybe there’s something more there than top-down market theory can grasp.

Social revolutions told people to throw away traditional, organic culture and “be themselves.” Modern “top-down” market culture then filled the void. The idea that you are born with some inner core “you” that you must discover over time, free from the influences of everything external, has a very romantic sound to it. It’s also totally false, or at best extremely incomplete. “You” are heavily a by-product of your environment. You don’t “free” yourself from culture; you simply adopt one over another.

So as age-mixing gave way to age-sorting, and people stopped taking advice from grandparents, family, traditions, etc., the market was there to fill the void. But the values of the market are top-down and profit-driven.  When a grandparent tries to teach their grandchild about life, one can assume that in most circumstances the child’s long-term well-being is an end-goal. When a market actor teaches a child something, there can be any number of other incentives; often tied in the end to economics.

Remember that organic, bottom-up progression involves slow evolution; strongly path-dependent on the past, which is assumed to carry a kind of underlying wisdom/understanding that is perhaps difficult to articulate, but is nevertheless there. On the other hand, top-down progression is about intellectual consistency with some defining value structure, like freedom, or fairness.

Older generations had their views on family, life roles, responsibility, money, work, and they were the product of slow evolution over time, integrating feedback from history’s experiments and mistakes. They had their problems, for sure, but evidently large-scale depression and suicide was not one of them. Then social revolutions came in and demanded corrections, many of which made sense at a theoretical level, and were amplified by market incentives. But top-down theory breaks down when it hits messy, multi-variate reality.

Without getting too bogged down in specifics, there is a meta issue here: a theoretical framework that hyper-emphasizes individuality and freedom may be more productive economically, and intellectually “purer” but it breaks-down, or at least reveals fundamental flaws, when it hits the reality of human psychology; which evolved on older, more organically evolved values.

Modern market culture pushes us to pursue things that lead to greater economic activity (dopamine), while neglecting those that may actually make us happier (serotonin), but can’t be monetized.

There’s a better job for you in another state. Go, pursue “your” dreams. You can visit your parents, childhood friends, and cousins on holidays.

If you have kids now, you’ll get “tied down.” You can always have them later (maybe…). Build your career. Travel the world.

Why are you wasting time cooking for yourself? Bill a few extra hours, and have the food delivered.

Your parents’ and grandparents’ views on life are out-dated. “Be yourself” and “follow your own path” with your peers, who largely feel the same.

Apologies to my millennial friends with romantic notions about how the “experience” of travel “expands your mind” and is “life changing.” I love traveling too. But that doesn’t mean I don’t recognize really good marketing when I see it.

There’s a big difference between what makes you wealthier, free-er, or more “empowered” (abstract concepts that, conveniently, have a way of increasing GDP) and what actually makes you – advanced monkey with a brain evolved over millennia – happier and more resilient.

The market’s individualism (liberating, but cold and detached) and traditional communalism (constraining, but warm and connected) are competing goods that need to be balanced. We are sucking at that balancing. 

It is much harder to balance competing goods than to simply let one take over our lives, even if the former is far better for us in the long run. When virtually all of the messaging/reinforcement in our environments supports only one side (because that’s the side that literally pays for messaging/reinforcement, including advertising and our educational infrastructure), that’s where so many of us end up.

Individuality, freedom, and financial wealth (all quintessential American, market values) – “following your own path” “pursuing your dreams” “not getting bogged down” “crushing it” – are real, valuable things. They’ve all played a key role in my life, for sure.

But the happiest, most resilient people I’ve known (men and women) have never “bought” fully into the market ideology (and it is ideology) that they are the be-all end-all of life. They understand that what’s old may be flawed and constraining, but if it’s old, that means it’s lasted. And things last for a reason; even if that reason isn’t easy to explain or fit within a theoretical framework. Freedom, empowerment, etc. are surely valuable. But so are durability and longevity; in other words, life paths and values that have been proven to “work” in the long-run.

As another old saying goes, winning is not the same as winning an argument; not even close.  The human brain is not designed in logic.  There’s no reason to expect an optimal human life to be either.

So if someone asks me for my thoughts on depression and suicide: sure, more therapists, discussion, and anti-depressants; certainly for the specific people who need emergency help now. But the meta-answer is to ask deeper questions about humanity, and to start questioning the life values that have been sold (and I do mean sold) to us; no matter how much we think they are supreme. Because we’ve clearly broken something, and it’s worthwhile to look back and examine a time when it wasn’t broken. 

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. 

Why I left a big law firm, but not BigLaw.

While I’ve devoted the majority of this blog to providing free resources on startup law and finance to startup entrepreneurs, I occasionally take the time to write about the economics of law firms and why entrepreneurs would be wise to understand it at a high-level.  This post will start out with a historical summary of positions I’ve taken on the subject, with links to applicable posts, and then branch into my decision to move my own practice and clients to a new type of firm – not BigLaw, but not quite traditional BoutiqueLaw.

  • The Economic Deflation of Startup Law – Early stage startup law, much to the benefit of entrepreneurs and top-tier lawyers, has become increasingly automated and commoditized. The end result is a form of “freemium” law practice, where (i) entrepreneurs can obtain quality representation for very little money, and (ii) quality lawyers can, thanks to automation, engage entrepreneurs early on without having to discount fees, defer, or any of the other old-school ways of obscuring the cost of legal services. Low-quality or narrowly focused “cottage” lawyers will struggle because their bread-and-butter work will have little to no margin, while higher-tier lawyers will thrive on their pipeline of later-stage, funded clients, which cross-subsidize early-stage work.
  • In Startup Law, Big Can Be Beautiful – Breadth and scalability are absolutely essential to the proper representation of a startup, and large firms have historically been where to get that.
  • Integrated Startup Law – Specialists Matter – Technology startups do not need and should not want unscalable, narrow “small business” legal representation. By their nature, they will need a broad set of legal specialties – Tax, Labor, IP, Regulatory, etc. – along the course of their business cycle, and failing to choose a firm at the beginning that can efficiently coordinate all those specialists will become a big problem. The analogy to healthcare is important. Also see – The Cost of “Staging” Your Startup Lawyers.
  • The Ad-Hoc Law Firm – The ability of networks of small law firms to coordinate efficiently will allow for (i) the replication of BigLaw’s breadth and experience, without its overhead and inflexibility, and (ii) the scalability that boutique firms alone can’t provide.

Nutshell Summary: BigLaw offers experience and breadth, but is largely over-priced and inflexible. Boutiques are cheaper, but often narrow and incapable of truly scaling, and their work is being commoditized.

BigLaw Beginning

So in my own career, I started out at a big firm with a group of fantastic lawyers whom any startup would be well-served by, but I increasingly butted heads against the firm’s (separating the lawyers from the institution is important) policies, including (i) IT policies with respect to new technology that needed to be adopted, (ii) billing policies around how to charge startup clients, and (iii) personnel that simply didn’t want to do things differently and weren’t incentivized to care anyway.

Your Boutique Can’t Scale

I watched the market, and had some overtures from boutiques in the area, but every time I came away underwhelmed:

  • Lower Pay, Lower Lawyers – Often the boutiques had very low rates, but their lawyers made a lot less income.  True innovation is about doing more for less while earning more – it should be win-win economically on both the client and the lawyer’s end. That’s why the most disruptive startups aren’t in it to make less money, they’re in it to make more money, but on a model that makes the end-price lower by cutting out fat, not muscle. If your firm is built on paying lawyers less – guess what? You’re just going to attract lower-quality, less ambitious lawyers. Surprise, surprise. Anyone can lower their price tag.
  • Where are the partners? – A lot of BoutiqueLaw firms will advertise that their attorneys offer “partner-level” service.  The reality is that most boutiques are run by senior “associates” (never made partner) from large firms who started their own firms and donned the partner label.  Early-stage clients might not care about this because their interactions are usually with associates anyway, but a lack of true partner experience within a firm can mean (i) your late-stage company is effectively funding on-the-job training, and (ii) that training can lead to mistakes.  A scalable firm needs true partners with the credentials and experience to actually provide partner-level service, otherwise top clients will have to go elsewhere.
  • Where are the specialists? – No one had a good answer for how to efficiently provide full service legal representation to clients. Asking them to engage a dozen firms on a piece-meal basis and manage a dozen different bills is not the right answer.
  • Where’s the technology? – If you think a lot of law firms haven’t joined the 20th century with respect to technology, check out some boutique law firms.  A lower rate is often used as an excuse for being inefficient and taking longer to do something.  Smart clients realize that their legal bill is a two-part equation: rate * time spent.  And if their lawyer is taking forever to do basic stuff, the lower rate is a mirage.  Startup law is for technologists, not cottage industry practitioners.

So why did I move my practice to a smaller firm (Miller Egan)?  Addressing the above issues in order:

  • The compensation structure is designed to attract top talent lawyers, not people who are looking for semi-retirement.
  • The firm is built and run by partners who were partners at the country’s leading law firms, but got fed up with the bureaucracy and inflexibility.  This means the firm can truly provide the “partner-level” counseling that is traditionally found only in BigLaw and that large, late-stage clients will require.
  • The firm has a well-developed network and process for coordinating specialist counsel for clients when needed, so clients can get the full service representation they’d receive at a big firm, but under a far more efficient model.
  • Technology? I’m CTO. #Howyalikedemapples

The above post should be read as a clear message to both traditional BigLaw and traditional BoutiqueLaw. Big can be important, and boutique can be cheap, but small, flexible, and scalable may eventually eat your lunch.  And let me tell you, that lunch is delicious.

Why I Chose Austin

A certain article has been making its way around the Austin twittersphere as of late, highlighting pros and cons of austin as a startup/tech hub.  I actually don’t have much to comment on Trevor’s thoughts on our city, other than that his portrayal of the angel scene is perhaps a bit exaggerated, although not entirely off mark.  Obviously in comparison to Silicon Valley there aren’t that many value-add angels walking around Austin, but I’d argue that, at least at the seed stage, capital and advice/mentoring don’t necessarily need to be linked. There are tons of highly knowledgeable mentors and advisors here, even if they aren’t the people writing checks.

On a personal level, my wife and I didn’t have to think twice about moving to Austin after spending 3 years in Massachusetts for law school.  The east coast was simply out of the question – neither of us can stand 6 months of painfully cold weather.  And to all the Bostonians out there, spare me the comments about our heat. Walk outside at 7am or 7pm on the hottest day of the year, and it’s gorgeous.  In the Boston winter, it sucks ALL DAY.

My wife grew up in Southern California, I’m Texan, and I knew that I (i) didn’t want to work for billion-dollar multi-national companies, and (ii) wanted to work as closely with tech startups and entrepreneurs as I could.  I’ve never had the classic “lawyer personality,” and to be honest, I don’t like working with them much either – though my co-workers are awesome. I prefer people who are always looking for ways to tinker with things or build new ones, and who aren’t afraid to ruffle a few feathers about it.

So Austin and Silicon Valley were really our only options. Since we both went to UT for undergrad, knew about Austin’s growing tech scene, and that you didn’t have to be a millionaire to live in something larger than a cardboard box, ATX was a no-brainer.  The legal market is small and hard to crack, particularly because every lawyer and his mother in TX wants to work here, but thankfully Andrews Kurth gave me an offer.

Best decision of my professional life… so far.  If I had to argue for Austin as an excellent startup/tech hub, here’s what I’d say:

  • No need to argue for Quality of Life – just look at how we rank on all those annoying lists that magazines/journals pump out all the time
  • UT is starting to see itself more and more as a source for pumping out entrepreneurial talent, as reflected by the growing number of startup-focused programs
  • There’s an enormous sense of community among people involved in startups.  Call yourself a startup founder, and someone will start plugging you in.
  • Bootstrapping and forming businesses that aren’t necessarily targeted at world domination gets you much more respect than in the valley. There isn’t nearly as much of a sense of urgency to slap a VC brand on your LinkedIn page.
  • Growing diversity of capital – sure, we could use more big-named local VCs, but in my own practice I’ve seen enough east and west coast money flowing in to know that we are on everyone’s radar.
  • Growing diversity of companies – I’ve seen a growing number of biotech and consumer-focused startups coming up in Austin, notwithstanding our enterprise-heavy funding environment.
  • The city itself feels like a startup.  Ask someone in Austin how they feel about the city, and you’ll often see a glimmer in their eye.  People feel invested and connected in this town, not as if they’re just one more developer or founder in a sea of others fighting for the prize.

I love it here. I get calls all the time from recruiters offering jobs in other cities, including Silicon Valley, and my response is always the same: if you hear about something interesting in Austin, let me know. Otherwise, I’m not going anywhere.