Hillbilly Elegy: Not a Book Review (Some Thoughts on Empathy)

With eight flight segments and plenty of downtime over spring break (last one ever!), I was able to crush through some of my reading list, and Hillbilly Elegy by J.D. Vance was at the top.  It’s become very trendy for my more liberal friends (and media) to drop this into conversations as an explanation for how and why Donald Trump has somehow become President of the United States of America, and based on some brief web searching, there are plenty of opinions both ways on Mr. Vance, his book, and what it all means – but that’s not what I’m here for.

For those of you who don’t know, “Hillbilly Elegy is a passionate and personal analysis of a culture in crisis—that of white working-class Americans” – full synopsis here.

I didn’t really have a goal in reading the book, other than to see what everyone was talking about – but I quickly found myself reacting to almost every story in one of two ways; (1) unintentionally condescending (“yep that’s what I’d expect from a redneck”), or (2) viscerally empathetic (“holy shit, I think I might sort of get this”).  I’m sure people across the spectrum would react to each piece of this book differently – but I grew up neither rich, nor poor, and I increasingly have a difficult time relating to those who religiously (small “r”) regurgitate Bill O’Reilly or Rachel Maddow’s talking points.  What struck me the most about those moments of empathy (not sympathy) were that they were orders of magnitude more intense than those things that I found disturbing about Mr. Vance’s upbringing.

Two episodes particularly struck a chord:

In his younger years, J.D. took it upon himself to sucker punch a bully, and though he feared the worst, in the aftermath he sensed a “hint of approval” from his teacher who gave him a token punishment and a seal of approval from his grandmother who told him, “sometimes, honey, you have to fight… it’s just the right thing to do”.

For three years in elementary school I was mercilessly tortured by a classmate (let’s call him Brian).  Unlike Middletown, Ohio (as I imagine it), Milton, MA does not condone playground justice in any way – but after yearof guidance counselor sessions and “friendship meetings”, nothing changed and I was miserable every day at school.  Then, on my first day of fourth grade we had a little scuffle that resulted in another parent conference, in which the guidance counselor suggested that I switch classes to fix the problem.  I was not in this meeting, but it is my understanding that my father (who was quite a large man and happened to have been drafted by the Dallas Cowboys in 1971) called the counselor (who was rotund and whose name was Peggy) “Ms. Piggy” and told her that moving forward “my son has explicit permission to punch this kid in the face the next time he lays a finger on him”.  Well, about 15 hours later, Brian tried to physically remove me from a chair he deemed to be his, and he ended up with a bloody nose amidst a pile of overturned desks and chairs.  I ended up in the principal’s office, listening to how my parents were “promoting violence in the school system”, and much like young J.D. was pretty sure I was going to be in a lot of trouble.  Brian never picked on me again, and the only further mention of the incident in our house was that there was a difference between what I did and starting a fight – and that I was never to do the latter.

In reading his story, I could feel the helplessness of a young boy in a school system that couldn’t/wouldn’t help in the face of bullying, and I can remember the soft approval from family that I knew would have my back, regardless of what else I’d have to face out in the real world.

Fast forward to Yale Law School, and J.D. is at a recruiting event for a prestigious law firm (just think Leo at that dinner on the Titanic).  Not knowing what to say, how to say it, or what fork to eat with (even though he looked the part of a typical white dude), he was flustered and barely keeping above water.

I, weirdly, didn’t own a suit until I was a junior in college (what’s wrong with khackis and a blazer?) – and I remember throwing it on for one of my first big recruiting events at an investment bank, for which I had made it to the in person phase of the interview process (they even paid for my train to NY!).  I believe my discomfort was probably 1/100th of what J.D. felt, but I remember feeling “less than”, and I remember resenting 75% of the people in the room, with their scripted Ivy League recruiting pitches and refined demeanor.  Due to generous financial aid and family that stretched their limits, I was lucky enough to have gone to school with people like this for years – but this was different and I was in over my head.  This was a playing field that I was ill equipped for, and I could feel it (I was also not qualified for the job, which I did not get).

For some reason, both those stories really hit home for me, bringing back memories and emotions that I hadn’t honed in on in a long time.

I started this post by thinking of how to tie this into VC and startups – “you are not always the target customer”, “don’t assume you’re the smartest person in the room”, “figure out why they think this is something to dedicate their lives to”, “diversity is not only right, but it can be profitable”.

But fuck it.  My takeaway is that I am going to try to bring more empathy into my decision making processes, in general.  I could have talked about Mr. Vance’s recollections of attempted murder, abusive relationships and drug-fueled destructive behavior – but for me, in this case, it’s the similarities that I’ll focus on, when comparing my experience to those of someone whose life has been so very different from mine.

The more we can do that, the better conversations we can have, and the more productive we can be in our relationships and in/across our communities.  We normally don’t have the luxury of reading someone’s memoir to hash these things out, but with a little effort, it can be done.

On the Self-Importance of MBAs

Kelly Fee, a Booth alum, recently posted A Call to Re-brand for MBAs (specifically in tech).  It relates to a lot of conversations that I’ve had about the value of an MBA – I’ve seen many fellow students post that they agree and are happy that someone has expressed what they haven’t been able to say.  I’m all for MBAs representing themselves well out there, but I disagree with the crux of her post.

My reaction to Kelly’s “Three petitions for MBAs in tech”:

Please stop belittling the MBA. You make yourself look bad.

“If you got nothing out of your MBA experience intellectually, it’s your own fault” – I agree with this on the surface.  Business school is an awesome place to explore new interests (academic, experiential, etc.), and I’ve viewed it as a sandbox in which to try new things.  Personally, I de-emphasize class/grades, and I spend a ton of time working for free for super smart people in spaces in which I’m interested – this is one of the biggest benefits of Booth.

You can learn cool shit in business school – no argument there – but that is not where the differentiated value is (remember Matt Damon in that Harvard bar?).  The two main things business school does for people (like it or not) are:

  1. Brand you – It’s hard to get in, and top schools do the hard work of vetting out prospective students.  By getting into school, you place yourself in “elite” company and will reap the benefits of this in the eyes of employers who want to hire smart, driven people.
  2. Give you a network – Call it a “2-year ‘break'” if you want, but that’s what it is, and that is OK.  I’ve met incredibly smart, interesting, genuine people during my time at Booth, and the deepest connections that I’ve made have nothing to do with “school”.  Early morning stumbles down 6th street after Austin City Limits, 3am post-TNDC (Thursday Night Drinking Club) tacos with my buddies, watching I Love You, Man four times since September – those are what make school worth it. Business school is awesome and fun, and that is OK – I don’t feel the need to apologize for it.

This is not to discount the knowledge that you can gain, but I can Google how to unlever beta.  You can learn the nuts and bolts of business anywhere – but branding and networks are more elusive, and those are the real competitive advantages that you enjoy as an MBA.  If you think otherwise, I’d be curious as to why you’re a better candidate for a position at Google than the person who has worked there for six years.

I don’t belittle my MBA, but I do have an opinion on what it is (and what it isn’t).  I love school, and I would do it all over again – but don’t tell me what business schools means to me and how I should represent it.

Please own your secretly intense side

“Please be authentic in speaking about your B school experience and stop being a punk” – what does this even mean?

Some people study a ton for the GMAT and some don’t have to (I did); some people freak out during recruiting and some don’t (I didn’t).  Kelly says that “the journey of personal and professional self-discovery accelerates in business school and the majority of people leave changed” – uhh, I guess?

Getting into school is hard.  Getting a job can, of course, be stressful – but it’s easier to do in business school than it is almost anywhere else.  Successfully graduating from business school is a joke.

I don’t understand the plea, so it’s hard for me to take action.

Be honest. Be humble

100% agree.  Kelly correctly says “they care about your value add, so let’s roll up our sleeves do our core jobs well, eh?”, which doesn’t really jive with her apparent disappointment at being asked about powerpoint presentations.

I actually think this is the single biggest reason employers (or other employees), at times, don’t like MBAs.  The impression is that MBAs think they are better than other people; if you want people to respect you (especially in a results-oriented environment like Silicon Valley), do a good job – it doesn’t matter where you went to school.

I recently worked on a project for a startup with someone who said “I’m an MBA student; I’m not here to do grunt work.”  That is fucking insane.

A big part of the reason MBAs get discounted is that people would rather work with people who are cheaper, more humble, and who have been actually working for the past two years.

If I had a plea to business school students, it would be to remember that you’re not that special, so enjoy what you’ve achieved and been given, and recognize that that degree doesn’t mean shit when it comes to winning a deal or getting that new product to market… though that classmate of yours on the customer’s procurement team may be a good first phone call.

Evaluating Products & Markets

I received a lot of great feedback on a previous post about evaluating founders, and the same question came through several times (mainly from people who are starting companies): “what do you look at next?”  Looking at initial diligence, there are a few boxes that need to be checked with any intro meeting, and once I feel that I have a good understanding of the team, I want to dig in on the product and market.  Here is how I try to determine if the product and market represent a real opportunity:

What is the problem that your product is going to solve for?  One of the quickest paths to a “no” from a VC Associate is to fail to convey the existence and magnitude of a problem.  Last spring, I looked at three companies in the pet care space (though only one made it in the door for a pitch) – each one had a solid team of execution-oriented founders, some initial traction, and a unique business model that worked at a unit level.  I was never convinced by the magnitude of the problem.

Do people love their pets?  Yes.  Are they willing to spend money on them?  Yes.  Can you make a business out of caring for pets?  Yes.  Do people need a new way to monitor and care for their pets?  I don’t think so.  Is the process of caring for one’s pets so broken that the market is begging for a tech-enabled solution?  No.  Is this something that I can champion internally?  Definitely not.

That’s not to say that there isn’t an opportunity there.  As an example, people didn’t necessarily realize that we really wanted a new platform for intra-city private transportation – Uber, Lyft, and others have shown us that we did.  There are some ideas that will completely shift paradigms, and as the quote attributed to Henry Ford says, “If I had asked people what they wanted, they would have said faster horses.”  It is true that many of the best ideas will require foresight into problems that are harder to distill, which is why I try not to be dismissive of something like a dog walking app that, while not mind blowing on the surface, could be transformative.  Is it, however, up to the entrepreneur to convince me that this is the case.

What does your product do (e.g. what is your solution)?  Interestingly enough, I often have to jump in early on in a discussion to hit the pause button and ask “OK, can we step back and talk about what exactly it is you are doing” – likely a combination of too many pitch meetings and curse of knowledge.  It’s good to remember that this is the crux of your business, and it is not an area to breeze over.  Who are your customers?  What is your value proposition?  How do you plan to deliver it?  These are not difficult questions, so be sure to give them their due.

How big is the market?  This is one where I often get frustrated by figures that show either (1) a lack of understanding of how a market works, or (2) an intention to mislead.  Neither is good.  The U.S. healthcare market may be $3 trillion, but that is not the addressable market for your wearable.  Not every company has to be a unicorn (depending on who you are pitching to), and it’s important to understand that smaller, earlier stage funds may not be thinking that way at all when it comes portfolio construction.

An airtight understanding of a realistic addressable market and its trends, and a plan for how you will gain your share of that market are key to showing your own understanding of the business and the investment opportunity.  This can be bottom up or top down (ideally a bit of both) and should be a narrowly defined market based on your product offering and target customers.  Don’t throw up a number you can’t justify, as it’s an easy place to start poking holes.

Who else is doing it & why are you better?  Some people hate the generic competition slide, but I don’t.  Once I understand what you’re doing and what problem you are trying to address, I want to know (1) who is doing it now, (2) who else is trying to do it, (3) why hasn’t anyone done what you’re doing, and (4) how are you better?

Having a firm grasp of the competitive landscape is key, and a failure to demonstrate this will be an immediate red flag as to your own precision and thoughtfulness.  Don’t be afraid to bring up the competition because it is my job to turn over every rock in the space during diligence, and if there is something out there, I will find it.  I’d much rather hear it from you, and more importantly, hear why you’re going to beat them.

Deeper evaluation of the value proposition and defensibility will come.  Technical diligence, IP analysis, and references will all be part of a full diligence process, but what I need to see right away is how your idea could be special.

What is your time to market & how do you scale?  These questions can be treated separately, but it’s important for an investor to get a sense for (1) exactly where you are at in the product development/go to market process, and (2) the capital needed and runway you will have with this round of funding.  This helps to set milestones, make strategic decisions, and will ultimately play into other key elements of the diligence process such as the financial and competitive analyses.

What are the risks?  Most startups fail, and even though you may be confident in your idea and your ability to execute, it’s naive and dangerous to assume success.  While much of your pitch will require energy, passion, and confidence, this is a good place to show humility and rationality.  Are there macro risks?  Is there a dangerous incumbent that could wipe you out (hint: if you are eCommerce, this is Amazon)?  How defensible is your IP?  What assumptions have you made about the market and your customers?  What happens in a bear scenario of customer adoption and scalability?

If there were no risk, venture capital wouldn’t exist – and by pre-emptively surfacing these and addressing them, you will earn additional trust and credibility.

Keep in mind, this a preliminary framework to understand if a deal is worth digging in on; these questions will each ultimately generate pages and pages of analysis.  It does two things for me that I find valuable – (1) helps me be as efficient as possible by screening out deals that don’t satisfy high level criteria, and (2) gives me a framework from which I can dive deeply into diligence if it’s something I like.

Agree?  Disagree?  Am I missing something critical?  Let me know!


Recycling in Venture Capital

The topic of recycling in venture capital has come up a lot recently, mainly in talking to GPs who are either (1) thinking about raising a first fund, or (2) raising a second or third fund, while looking to transition to a more institutional LP base.  With a ton of things to worry about, recycling seems to that gets de-prioritized for GPs at this stage – that is a mistake.

Roger Ehrenberg of IA Ventures and Brad Feld of Foundry have both outlined their views on recycling (they like it); my goal here is to succinctly lay out the issue and the math behind it.

The problem – If you have a $100M fund and assume (for simplicity) that you charge a 2% management fee over a 10 year investment period, you end up with $80M to invest in companies, with the remaining $20M going to the management fee.  Thus, even if you deploy that entire $80M, you are only investing 80% of the fund.  VCs are judged on net returns to LPs, so investing only $80M is putting yourself at a disadvantage right out of the gate (on $80M invested, you need to return 1.25x just to return the $100M fund).

The Solution – Recycling.  In the case of an early liquidity event (let’s say a $20M exit), that capital can either be distributed to LPs or recycled back into companies.  S0, if you have a $100M fund, and recycle that early $20M return, you know have $100M to invest into companies out of your $100M fund (the initial $80M plus the recycled $20M).  Taking this a step further, if you are able to recycle $40M in early returns, you could potentially have $120M (original $80M plus $40M in recycling) to invest out of your $100M fund – you’re already $20M “in the money” at cost!  From the funds I’ve seen, 120% is a pretty common recycling ceiling in fund documents.

So why doesn’t everyone do it?  In general, established/successful funds managers know how this works and aim to get over 100% invested, if possible.  The main problem I’ve seen is with funds who scraped together their own capital and an HNWI-heavy LP base for an early fund(s), and who are now hoping to raise from more traditional LPs (e.g. fund of funds and endowments).  Venture capital is a long term game, and institutions with that time horizon prefer to plow early returns back into companies, getting as much out of their fund commitment as possible.  Less experienced GPs and individual investors could potentially be more interested in an early payout, creating a conflict of interest.  While LPs will have different opinions on recycling, GPs who don’t aim to maximize the dollars put to work in companies are doing themselves a disservice and hurting the financial return for both themselves and their LPs.

The Math

To get a 3x net return to LPs on a $100M fund, assuming an annual 2% management fee over 10 years ($20M) and 20% carry ($55M), you need to produce $375M in returns.


So, on a gross basis (at the company level), here is what you have to return at different percent invested levels:


Notice that, without recycling, to generate a 3x net return without recycling (investing $80M), you need a gross return of 4.7x.  Compare that to the scenario where you invest $120M, needing only a 3.1x return.  That is an incredibly large difference, and it is all due to recycling.

Looking at it a different way, assume that you are able to return 4x gross (congrats!) on any amount of deployed capital:


On a gross return basis, each of these scenarios is equal, but comparing the extreme cases of 60% and 120% invested, you get a $192M and $48M swing in payouts for LPs and GPs, respectively.

There are, of course, assumptions above (early liquidity opportunities, recycled dollars being put to work effectively, etc.), but the point remains – recycling benefits both GPs and LPs, and it is critical for fund managers to build an LP base with aligned, long term incentives.

Evaluating Startup Founders

If you ask any early stage investor what is the most important aspect to a deal, she will say, almost without fail, “team”.  Market, product, etc. are all key, but no matter the horse, you need the right jockey.

I always consider my own pillars of execution (aggressiveness, humility, pro activeness, and precision) when evaluating others, but this is the framework through which I evaluate startup founders and their teams:

Do they have domain expertise?  This is a pretty obvious one, but it’s not always quite so simple.  In, for example, a healthcare services company, there are many different vectors along which founders can spike – have they practiced medicine?  Have they run operations at a hospital?  Do they have healthcare (or any) startup track record?  Have they experienced something firsthand and conducted a ton of customer research to validate a problem?  Do they have a deeply drawn out thesis in a relevant area?  Hardi Meybaum of Matrix recently said on Harry Stebbings’ The Twenty Minute VC that MBAs with strong market/industry analysis, but no domain expertise, are able to find great opportunities, but often aren’t able to dig deeper on the underlying reasons why those opportunities have not yet been tackled.  He also adds that “having high empathy for the customer” is key, and without domain expertise, that can be difficult to master.  I agree.

The breadth and depth of a founder’s knowledge will vary, and the expertise will likely comes from a combination of experience and research, but if I meet with someone who doesn’t really understand the customers, suppliers, competition, technology, unit economics, and market dynamics of her startup, I interpret that as a lack of thoughtfulness and precision.

Are they passionate?  I’ve heard people argue that a founder needs to be passionate for the product and problem she is trying to solve; I’ve also heard that while that is great, sometimes a general passion to start a company and be an entrepreneur is enough.  The latter is probably OK sometimes, but I need to see the former to be really interested.  Company building is (generally) not glamorous work, and it’s hard for me to believe that someone who isn’t truly passionate about their idea and space will have the fortitude and commitment to see a company through the inevitable turmoil ahead.

Are they tough/Do they have grit?  Call it whatever you want, but a high level of sticktoitiveness is required to succeed as a founder.  Thinking back to times when you have overcome adversity may give you a flashback to past job interviews or MBA applications, but there is a reason people ask – and that reason is even more important with startup founders.  You will never know for sure without the stress test of real world tribulations, but being confident that a founder can display dogged perseverance in the face of adversity is critical in the evaluation process.

What are their motivations?  Related to passion – this can be tricky because it’s easy to tell investors you want to build a unicorn, but a $20M acquisition when you still own 50% of the company is a life changing amount of money to most founders (and a miss for VCs).  This is another one where you’ll never know for sure just how far a founder is willing to push the envelope, but you can get a feel for it when evaluating their passion and grit.  It’s also good to just ask a founder what her goals are, with the understanding that there is no shame in shooting for a small (by venture standards) win.  There are plenty of good businesses and good CEOs out there – but my job is to find venture-backable businesses and CEOs; those are not the same thing.

Can they execute?  I can generally get a good feel for expertise and passion in an intro conversation (and potentially even before, with some research), but execution can be a bit tougher to gauge.  At the very early stages, the ability of a founder to execute is absolutely critical, yet there is often a chicken and egg problem that you will have to make a bet on.  Best case scenario, you meet a serial entrepreneur who has shown the ability to push a company from zero to one and/or moved the needle elsewhere in some meaningful way.  That, unfortunately, is rarely the case, and I find that the best way to make a call here is to (1) evaluate their skill set (how are they special? domain expertise, rockstars in sales, tech, operations etc.), (2) observe how they handle the diligence process (are they aggressive and precise), and (3) reference the shit out of them (get as many data points as you can).

I have been on a deal before where we loved the idea, believed in the opportunity, and saw a broken business model that could easily be fixed; as the diligence process began, however, it became clear that we simply weren’t dealing with a top performer.  Incoherent pipeline materials, weak financial models, and a general lack of precision and timeliness in response to our inquiries all raised red flags as to the CEO’s ability to execute.  He had built a Potemkin Village – there was no way this guy was ever going to move the needle for us as a fund.  If someone we believed in came in with the exact same company, we would have moved forward – I took this as a good lesson in disciplined investing.

Are they “Truth Seekers”?  I first heard this term from Josh Hannah of Matrix (also on the Twenty Minute VC), and I think it’s an excellent way to evaluate just about anyone that I might be interested in working with.  I love meeting founders with insatiable appetites for knowledge, who devour new information in order to make data-driven decisions.  Founders who are able to preempt my questions about gaps in their business, while acknowledging those weaknesses and exhibiting a willingness and excitement to address them, are incredibly fun to work with.  Hannah says that he likes founders (especially pre-product/market fit) who seek to find and be transparent about bad news, have tempered egos, and know that they don’t have it all figured it out (e.g. not a cult leader with a reality distortion field) – it may not be complicated, but much like humility, it’s not necessarily common.

There are many different ways to evaluate the all important “team” aspect of a startup, and each situation will be different – there is no one size fits all matrix.  I find the above useful as I enter into a conversation, and as things unfold, I press where necessary, remembering that I am being simultaneously evaluated along similar parameters.

Thoughts or comments?  Get at me here.


Venture Capital & Tech Readings

This year at Booth, I’m serving in a Career Advisor role for the venture capital group, and I’ve been asked quite a bit about what people who are interested in the industry should be reading.  There is a ton of stuff out there, and it can be overwhelming, so I tried to put together a page of interesting stuff that would help people get started.

I’ve published the list here, where I’ll periodically make updates.  If you think I’ve missed something important, please let me know and I’ll add!


Four Pillars of Execution

I’ve asked many people a version of the question – “what makes a person successful in this role”, and the answers are pretty standard.  Recently however, I asked this question of someone who was to become a mentor, and he gave an answer that was both concise and comprehensive:

Be humble.  Be aggressive.  Be proactive.  Be precise.

As I’ve begun executing by these principals, I have been able to trace every single error or failure on my part to a violation of one of these pillars.

Humility – This has, admittedly, not always been a strength of mine, but the more I learn and pay attention, the more I think about how wise Plato’s Socrates was when, in The Apology, he said:

For my part, as I went away, I reasoned with regard to myself: “I am wiser than this human being. For probably neither of us knows anything noble and good, but he supposes he knows something when he does not know, while I, just as I do not know, do not even suppose that I do. I am likely to be a little bit wiser than he in this very thing: that whatever I do not know, I do not even suppose I know.”

Most people I know are and should be proud of their accomplishments – but it those who have accomplished great things and who continue to believe that there is so much else out there to learn that impress me the most.  As hubris and arrogance become part of someone’s persona, the absolute value of their contributions as a leader and/or contributor diminish.  People can, of course, get away with this lack of humility, but that does not mask the fact that it is a net negative in the aggregate over the long run; pride and confidence are important (I would argue critical) traits, but when unchecked by humility, they lead to a lack of awareness and limit the ceiling of one’s success.

Aggressiveness – This is something that I had always considered a strength, but by raising the bar and treating tasks as absolutely critical, I can now see that I was not properly calibrated for what it takes to aggressively execute in a startup environment.

An example:

12pm.  We have a mission critical legal document that needs to be proofed and executed by 9am tomorrow to secure financing (though we don’t technically need to send out until 1pm).  I send an email to the lawyer with a note that this is super important and needs to be done by midnight (9 hours early!).

2pm – He responds saying that he will get to it ASAP.

7pm – I follow-up via email just to be sure we are on track (he said we were good, so I’m really being extra diligent on this one).

11pm – I follow-up again via email, a little worried, but I built out that awesome cushion, so shouldn’t be a big deal.

1am – He responds via email – day was crazy and wasn’t able to get to it; will get someone on it first thing in the morning.

1:05am – I thank him via email and say by 8am is fine.

7:30am – I email him with a message of urgency.

9am – Miss deadline.  I fucked up.

This is just one example, but it’s one I lived through, and when that deadline hits, there is only one person responsible here – me.  At each point on the timeline, I made a critical error in aggressively ensuring that we met our goal.  Phone calls are generally more effective than emails, and to make sure that a lawyer (with many clients) has this top of mind, I need to be all over this.  If he can’t promise delivery, he needs to find someone else at his firm to bang it out; if he can’t, there are plenty of law firms out there, and I’m likely no more than a 2nd degree LinkedIn connection away from most.  It doesn’t matter that I prioritized the ask or that I built in wiggle room ahead of the deadline or that I pinged him five times letting him know we need this.  If anything, it shows that I was aware of the importance of the issue, but still failed to find a way to make it happen because email is easier, and I didn’t have his number, and that 9am deadline was a little arbitrary anyways, and he said it would be all set, and “I did my job”.  My job was to get the document executed, thus I did not do my job.

Being aggressive doesn’t mean being a jerk, but you can bet if some other MBA intern called up the lawyer at 1pm with a critical ask and ensured delivery with an explicit set of asks and deadlines, that was getting done ahead of my nice emails sent at socially acceptable intervals.

Pairing humility with aggressiveness is generally a recipe for success.

Pro-activeness – a little more generic, but important to both a company and to personal growth.  Thinking strategically while executing on the ground level can be difficult, but the benefits of looking ahead, both for disasters to avoid and for opportunities to exploit, can be a game changer.  When you have downtime, refresh yourself with a context switch and find a place to add value; maybe it’s a customer in the pipeline where you have the right inroads, maybe it’s a potential advisor that you could catch up with for 15 minutes to give an update, maybe it’s looking at the calendar for a meeting that could use extra prep work.  Don’t wait for someone to tell you what your next task is; find a task that excites you, and do it.

I often hear people complain about stagnation in their role.  In a startup environment, if you feel this way, you’re probably right.  And it’s probably your fault.  I’ve found that there is a lot of correlation between being proactive and being aggressive – but I think the difference is worth calling out.

Precision – While the other three pillars are more character/personality based, this is one that stands a bit on it’s own – delivering good work through attention to detail and precise execution.

This doesn’t need a lot of expounding, but I do think that being aware of the process through which you deliver your most precise work is important.  Some people work better when procrastinating, while others needs to plan well in advance; some like to work alone and finish a project in one go, while others prefer to iterate and get feedback along the way from others.  Regardless, precision is one thing that you absolutely cannot succeed without (especially when you are in more junior positions where granular analysis is so critical).

I recently helped conduct an interview, where each of the other three boxes was checked with ease, and it looked like we had a deal.  When an exercise (sent as a baseline test for competency) was turned in that fell short of the level of precision expected, the process was stopped dead in its tracks.  Non starter.

This isn’t a scientific analysis; others will have opinions on the nuances of the above, and on the weighted importance of each.  For me, I make a concerted effort to align my work with these four pillars, and by tying my failures back to each of them, I have tangibly improved my execution.

The Need for Authoritarian Leaders

On a bit of a 6+ week adventure (SF -> Boston -> Maine -> Greece -> Croatia/Bosnia -> Doha -> India), I’ve been able to make quite a dent in my to-read list; near the top of that list was Nathaniel Philbrick’s excellent In The Heart of The Sea.  It’s the story that inspired Moby Dick, and a bad movie (I’m told) of the same name was recently made.  The book is great; I recommend it.

After feeling a bit like I myself had survived a harrowing expedition through storms and disaster across the Pacific, There was a line towards the end that shook me back to my current context:

“Modern survival psychologists have determined that this “social”—as opposed to “authoritarian”—form of leadership is ill suited to the early stages of a disaster, when decisions must be made quickly and firmly. Only later, as the ordeal drags on and it is necessary to maintain morale, do social leadership skills become important.”

Analysis of leadership is not hard to come by (sand:beach :: leadership discussion:business school), but the balance between social and authoritarian leadership styles is one that I spend a great deal of time thinking about, both on a personal level and in evaluating early stage teams.

The whaleship Essex, while not a startup (it was actually quite a seasoned vessel), encountered great disasters that required decisive action on the part of it’s leader; Philbrick (along with cabin boy Thomas Nickerson, from whose notes Philbrick draws much of his story) contends that Captain George Pollard’s democratic approach to decision making and deferral to his officers played a large role in the ultimate fate of the crew.

While I haven’t heard of a sinking startup that resorted to cannibalism, the path along which startups grow is treacherous, and the authoritarian leadership required to steady the ship amidst the storm (see what I did there?) is certainly a prerequisite for a strong CEO.   Beyond that, however, the dynamic of the company will inevitably change as it goes from a few people in a garage (did you know that’s how some companies start?!) to a larger, more stable (hopefully) company, and as this happens, the skills associate with social leadership will become more important.

Scaling a company, and building a healthy corporate atmosphere is a complicated topic, and there are many schools of thought and accompanying examples of the “best” methods.  As I discussed in Hercules v. Theseus, brilliance and force are best when paired with empathy and humility, but at the earliest stages of a startup, an authoritarian style is a better indicator of a leader’s ability to build a truly great company from scratch.

In his must-read book, Originals, Adam Grant talks about forming coalitions, and the personalities required to get a cause of the ground compared to those required to scale it to a place where it has great impact (great ideas do not equate to success; great execution does).  Using the women’s suffrage movement as an example, he discusses how the original members of a group are generally the most radical, but once momentum is gained,  tempered leaders are more effective in forming coalitions that are required to foster a culture that allows the movement to reach scale.  There is a parallel here (albeit not perfect) where early company leaders must be fanatical about their company, and must be willing to confidently make difficult decisions and execute aggressively in order to get to a point where they can afford to focus more on morale and less on keeping the company alive.

As I think back to some of the deals that I’ve evaluated, the area where I’ve become the most cynical (e.g. where I’ve improved the most) when looking at deals, is team.  There are a lot of great ideas out there, but the number of people capable of executing on these ideas is much smaller; a passionate, authoritarian leader who can get shit done and knows how to coax the same out of others is so critical that when you hear someone say “I’d back her without even hearing the idea”, it’s barely an exaggeration (and it makes a lot of sense).

Bold decision-making does not mean recklessness, and it also doesn’t mean ignoring all advice or being a complete asshole all the time; it is, of course, not that black and white.  Captain Pollard may have been well liked, and he may have been a fine captain under certain circumstances, but he goes down in a storm 10 times out of 10 (in fact, he managed to go down twice before forced retirement), but in industries where storms are frequent (whaling and startups), the leader who, with the appropriate experience and wealth of knowledge, can command the respect of her team through bold decision making and ownership of responsibility, is a ship’s only chance.

Hercules v. Theseus

After an incredibly rewarding/challenging summer working for the venture capital firm, Data Collective (dcvc.com), I took a planned hiatus – some much needed family time up in Maine, along with the more stereotypical MBA summer travels to Greece and Croatia.

Having decompressed a bit, I found myself procrastinating – “this isn’t a travel blog, so I’m not going to post pictures of Santorini and rave about the local wines”, “this isn’t a book review blog, so I’m not going to talk about Edith Hamilton’s Mythology, and how it provided a streamlined escape through the annals of Greek Mythology, while I wandered around Athens”, etc.

I hate excuses, and I dislike inaction – so this should be the beginning of a more consistent cadence of posts – most will loosely tie into the world of startups – technology, markets, trends, leadership, legislation, companies, people, etc.

So – some thoughts on idols and leadership vis a vis Hercules.

When downloading the aforementioned Mythology, I was excited to dive into stories of the gods and heroes, the basics of which I had vague outlines of in my head (either Perseus or Theseus killed Medusa… and the other killed the Minotaur… and someone’s dad jumped off a cliff because of a white sail… the gods were all assholes…)

The Greek hero of whom we hear the most is generally Hercules; the last Hollywood stab at Greek mythology that I saw was The Rock’s excellent confidence man portrayal of the legend in Hercules – though I admit I can not be unbiased when it comes to The Great One.  Hercules is so amazing because (due to his half-divine background) he could do things that no one else could; the tales are too numerous to recount, but he slayed things like this, this, and these as part of his 12 labors; he played life on hard mode, and generally could not be stopped.

The problem with Hercules is that he was also incredibly unhinged, and other suffered.  Among his indiscretions, he killed his music teacher (by accident) because he didn’t like the material, and he murdered his entire family (influenced by Hera; the catalyst for the 12 labors).

Despite the decidedly murky other side of the coin above, Hercules was the revered as the greatest hero of Greece.  In Athens, however, things have been viewed a bit differently.  As Edith Hamilton notes:

The greatest hero of Greece was Hercules. He was a personage of quite another order from the great hero of Athens, Theseus. He was what all Greece except Athens most admired. The Athenians were different from the other Greeks and their hero therefore was different. Theseus was, of course, bravest of the brave as all heroes are, but unlike other heroes he was as compassionate as he was brave and a man of great intellect as well as great bodily strength. It was natural that the Athenians should have such a hero because they valued thought and ideas as no other part of the country did.

Theseus’ accomplishments were also many; he had some labors of his own – none of which were motivated by domestic violence – and he killed The Minotaur.  He also talked Hercules out of suicide after the whole murdering his family thing.  It’s not these feats that distinguish Theseus, however – it’s what he did not do that was so impressive.

His humility especially shines through in two of my favorite stories.

First, upon becoming king of Athens, he relinquished his power to the people in what was a very out of character move for power hungry, *narcissistic* characters of Greek mythology:

So Theseus became King of Athens, a most wise and disinterested king. He declared to the people that he did not wish to rule over them: he wanted a people’s government where all would be equal. He resigned his royal power and organized a commonwealth, building a council hall where the citizens should gather and vote.

As someone who gets chills thinking about George Washington, in the style Cinncinatus, relinquishing the opportunity to run the show as a military dictator, I’m surprised I had never heard (or hadn’t remembered) this version of Athenian democracy’s birth.

My favorite story, however, was his attack of Thebes (something he did not want to do, but did out of a moral obligation).  He marches in and conquers (as one does), but once his objective is complete (allowing the survivors of a previous battle to bury their dead) he leaves.  Again, not a typical move for a victorious Greek.

I see many (mostly good) articles on what makes a good leader today, mainly as it relates to building and running technology companies.  Empathy and team building are always emphasized as top priorities, but oftentimes the people that rise to celebrity status (e.g. Steve Jobs and Elon Musk) seem more like Hercules than Theseus.  It is, of course, not black and white, but the general portrayal of both Jobs and Musk is one of brilliant innovator with disregard for the human beings within his sphere.

While they are surely the exception rather than the rule, I find it interesting that we worship these Herculean figures (who we no doubt need to move mountains), when it is far more impressive to accomplish these massive feats of (innovative/intellectual) strength while remaining humble and empathetic.

When evaluating teams, I have found that there are plenty of smart people out there, but at a certain part, IQ is pretty binary, and in the world of early stage technology, there are diminishing marginal returns.  Very rarely do I come out of a meeting with a company and think “wow, we just met an idiot”, but it’s not uncommon to think something like “smart person… and she knows it – seems to lack self awareness and I worry about her ability to attract good people and overcome the inevitable speed bumps ahead”.

Bring me a true Hercules and I’ll get on board, but for my money, I’d prefer to back, help and commit to a Theseus 11 times out of 10.

The Lives of the Dead

The Lives of the Dead is the final chapter in The Things They Carried, a novel by Tim O’Brien that mixes truth with fiction (and at times argues the latter actually holds more truth than the former), while weaving in and out of the Vietnam War.

I first read The Lives of the Dead in the Spring of 2002 (15 fucking years ago) at a time when I wasn’t reading much, despite being assigned quite a bit by my teachers (I still half nod out of vague recognition when someone makes a Holden Caulfield reference as if I read more than 10 pages of… Catcher in the Rye?).  For whatever reason, this class (John Campanale’s Green Class) motivated me, the book inspired me, and this chapter struck an emotional chord.  15 year old boys at all-male Catholic schools are probably not the best equipped to think deeply about topics like love and death, but Camp really got us thinking.  And we weren’t going through the motions – we were really thinking about shit.

I’ve read hundreds of books since then, and never again have 20 consecutive pages affected me to that degree.  You should go read the whole book – it’s more powerful when framed as part of a whole than as an independent essay, but here’s what he says:

Remembering his first date in fourth grade:

Linda was nine then, as I was, but we were in love. It was real. When I write about her now, three decades later, it’s tempting to dismiss it as a crush, an infatuation of childhood, but I know for a fact that what we felt for each other was as deep and rich as love can ever get. It had all the shadings and complexities of mature adult love, and maybe more, because there were not yet words for it, and because it was not yet fixed to comparisons or chronologies or the ways by which adults measure such things.


And on the power of stories:

But this too is true: stories can save us. I’m forty-three years old, and a writer now, and even still, right here, I keep dreaming Linda alive. And Ted Lavender, too, and Kiowa, and Curt Lemon, and a slim young man I killed, and an old man sprawled beside a pigpen, and several others whose bodies I once lifted and dumped into a truck. They’re all dead. But in a story, which is a kind of dreaming, the dead sometimes smile and sit up and return to the world.

A blog is a really just a way to tell a story – and whether directly or indirectly, a good one will highlight things that you are passionate about and that you love.  That’s what I’ll do here, and while it’s mostly for myself, I can admit that I do like attention – so maybe others will enjoy it as well.