Against Optionality.

Make no choices. Keep all options open. Pay the price.

Coming out of the worst of the pandemic, everyone has all this pent up energy to make big life changes at once. Changing jobs, moving cities, getting into or out of serious relationships - it’s all the same impulse and it’s understandable. After 12+ months of The Same, now is the time for Different.

It’s a national phenomenon (at least) and tech people seem like they’re leading the charge by doing the most and doing it the most publicly. What’s new.

But what may feel like a unique moment is just the apotheosis of a particular strain of contemporary (tech) thinking that prizes optionality and flexibility over everything else.

The tech ideal of being a bi-coastal, sexually-unmoored IC with a paid newsletter and a scout fund is fundamentally about optionality and flexibility.¹ Total freedom with fallback options and alternatives aplenty. That desire for optionality and flexibility is a reflection of the belief that there might, at some point in the near future, be something/someone better to do/be. 

Tech folks are primed to love optionality because in tech the outlier outcomes are so much better than the rest. The upper bound of possibility is so lucrative and fantastic (joining a company that goes public and mints you millions practically overnight, for example) that it’s so obviously worth it to continuously optimize around that.

This mode of thinking is so fundamental that it seems impossible that it wouldn’t pervade the rest of our lives; not just what work I do but how I live, where, and with whom. I need fingers in lots of pies and to shut no doors to alternatives because the gulf between the best and second best versions of my life is vast. It’s power law optimization for the everyday.

Counterintuitively, being optionality-obsessed is just as fearful as it is optimistic. It reflects the fear of making the wrong choice just as much as hope for making the right one. What happens if I stay too long in the “wrong” job or date someone and it doesn’t work out or I miss out on that next shiny object that would have changed my life? I’d be ruined by opportunity cost! Optionality lets you preserve the chance that you’ll strike gold and minimize the risk of committing to the wrong thing but only by avoiding commitment at all. 

Options aren’t free. They come with hard and soft costs. So if you want to keep all options open, you have to be prepared to pay for it.

As Byrne Hobart put it, an open calendar gives you maximum flexibility to say yes at the expense of intermittent loneliness and an Uber gives you flexibility in your transit plans at the expense of a $40 trip from Manhattan to Brooklyn. Want the flexibility of a month to month lease? It’s yours for a cool 30% premium over a long term lease. 

And if you want to bounce between jobs, you need to figure out new politics, adjust to new workflows, develop a new internal track record, etc. before you can even do your job competently/effectively. Beyond transaction costs, if you leave before your work bears fruit, you lose the opportunity to learn from it and improve meaningfully on the process that went into the work in the first place.

You need to let positions ride to compound the gains. If you keep taking risk off the table (as it were) along the way to reallocate to some juicier, higher potential outcome/position, you might be kneecapping yourself and your own growth. If you never risk commitment to the wrong thing, you might not have enough experience to confidently commit to the right thing when it comes along. Finally, if you’re always focused on the next thing, it seems hard or impossible to simultaneously focus on the task or opportunity at hand.

I’m a believer that we ought to “disagree and commit” when making decisions as a group. We can apply a similar idea in our own lives. Accept that something might be wrong but, based on the belief that the worst choice is no choice, do it anyway and do it with gusto until you’re demonstrably right or wrong, or have gotten from it all you can. Then move on and do it again.

Having been in one job for nearly five years right out of college, I’m obviously talking my own book here - perhaps even to the point of self-delusion. But while I can’t say what the future holds, I am comfortable and confident in my assessment that had I left my firm after two or three years (typically of someone entering venture), the loss would be far greater than 50% of what I’ve learned and grown into.

Commitment need not be for life or even particularly long term, but the refusal to commit to something at all can defeat the purpose of doing it in the first place. It’s a Faustian bargain: trading away impact for optionality.

Make no choices, keep all options open, pay the price.

In other words, burn the boats.

1. Sorry to sound like a prudish sourpuss but I’m trying to paint a picture here. Bear with me.

Be a star or a janitor.

How to prioritize at work early in your career.

I talk a lot of shit and give a lot of negative career advice. Don’t be a generalist. Don’t work in venture capital. I stand by that but I’d be remiss not to present a more constructive viewpoint on how to think about early career building.

For most people, especially early in their careers, there’s just not a lot of agency at work. By and large, junior people are told what to do and it’s on them to execute as instructed. Even if you’re well paid knowledge worker, you’re mostly carrying out marching orders from your boss early in your career.¹

Mostly.

What you do with the agency you DO have, however small, is probably more important than anything else beyond basic competency. And if you’re lucky/privileged enough to be in a junior role with significant autonomy and agency, how you choose to use it isn’t the most important thing - it’s the only thing.

When do you raise your hand? What do you volunteer for? When do you ask for permission first? How do you define, measure, and communicate success? How do you prioritize your goals vs the team’s priorities?

In short, how do you earn your colleagues’ trust, make yourself valuable, and grow into the job you want?

Here’s what I’ve learned and the rough framework I’ve found. You should always strive to do the work either 1) no one else can do or 2) no one else wants to do. Be a star or a janitor. Be like Mr Clean - the perfect mix of sex appeal and down and dirty effort.

As a janitor, you should enthusiastically tackle the projects and tasks that are just miserable. Find what is going to be most painful and take it on with gusto. Shovel shit for your team and they’ll love you for making their lives easier. Do that and you’ll find yourself in the guts of the business, indispensable to your team whose gratitude you’ve earned through brute force. Along the way, you’ll learn much faster by getting into the messy process and mechanics than you would have otherwise.

As a star, you should seek out the work you are uniquely capable of or the opportunities where you have some comparative advantage. Take the initiative to do things that might not have otherwise happened and your team will value you for your unique contributions. Do well, and the leash will get longer until eventually those things you’re best at are your primary function.

The corollary here is to avoid (as best you can) anything that is “replacement level;” the hum-drum tasks that neither drive outsized value nor relieve disproportionate pain. This the mushy middle of “just doing your job.”

Of course most jobs most of the time are just that - jobs to just be done. That’s fine. Do what’s needed and do it well. Obviously. The point is to define your role (through actions) to look as  bipolar as possible.²

Pull this off and you can initiate a flywheel whereby you get more autonomy and a better fitting role over time. You’ll be increasingly doing only the work you’re either best at or most appreciated for.

But how do you avoid becoming a full time janitor? How, for example, do you avoid the trap of becoming a de facto assistant/bandaid applier for your boss or winding up in a job you never wanted at all?

The key is to focus on projects rather than ongoing maintenance. This is the difference between a salesperson on a small team with no support stepping in to project manage a CRM migration or major cleanup and being the sales ops person responsible for maintaining the CRM on behalf of the whole team day to day. The former is a pain in the ass that someone needs to own and do well once. The latter is just a different job that you, as a salesperson, might not want.³

Last year I built a new operating model for my fund from the ground up. It was not a fun time and no one much wanted to do it. In doing this rather miserable, janitorial work I 1) learned a ton about how venture funds really work on a granular level and 2) earned the right to help drive conversations about strategy going forward. Having built it, I don’t spend much time/effort inputting new data into the model on an ongoing basis myself: I took on the major pain of the initiative but not the “job.”

Ideally, the janitorial aspects of your job should fall within your role as “person who gets shit done” rather than “person whose job it is to this one annoying thing or collection of annoying things.” 

You can apply a similar logic in your role as a star. There’s a fine line between taking the initiative on opportunities to drive unique value and just being an asshole not willing to help out the team.

To make it personal again: I have generally tried to source deals through my own networks (younger founders, more under the radar, etc.) and through brute force (junior folks have the least valuable/constrained time) rather than trying to do a worse version of what my partners do. I could try to compete with them and with their peers at other firms or I could try to find some angle that wasn’t necessarily better or worse but was certainly harder for my partners to replicate, especially earlier in my career. I tried to add something different knowing that I couldn’t possibly outperform on an equal playing field. 

Those angles and avenues for both janitorial work and stardom won’t present themselves on day one and they may not ever be obvious at all but I promise you they do exist. Find them.

The point of this framework isn’t to guide your every decision; it’s to help you prioritize at the margins. But all those marginal choices add up over time. More than that, they compound and collectively form the basis of your role and reputation. So choose wisely.

Thank you to Chris Brown and Justin Gage for editing and feedback.

1. NB: this is written from a place of privilege and is generally (though not exclusivity) meant for similarly privileged readers. For many if not most people outside of high status white collar work, jobs don’t work this way.

2. I cannot over-emphasize the extent to which you should not present this framework to manager as an excuse to not do something. Do not do that. If you are told/asked to do something by your manager, do not for a second think that it will ever be to your benefit to do anything less than your best at it.

3. If, in this example, you are the sales ops person then there will almost undoubtedly be a different version of the same paradigm within your role. Do not take any of this to mean that some roles are inherently low value or lacking opportunities to excel beyond the hum-drum. In my experience, that is just not true.

Don't be a generalist.

You can have generalist knowledge or a generalist skill set — not both.

My thinking here started, as it often does, with a Justin Gage tweet.

A few weeks ago Justin tweeted that “be a generalist” was the worst piece of career advice he’s ever gotten. Good or bad, it’s at least broadly accepted as a Smart Take to have. There are numerous books extolling the virtues of being a generalist. I think it’s terrible advice... generally speaking ;)

justin g. @itunpredictable

thinking about the worst advice i've gotten in my (short) career, "being a generalist" is probably the most destructive thing i was told. actively set me back my a couple of years

January 4th 2021

25 Retweets728 Likes

NB: this is confined to non-technical folks (“biz side”) at startups.

TL;DR when people describe themselves as “generalists” what they often mean is “overall smart person with/seeking high status but unspecific job.” That’s not helpful. But founders/startups DO need executors, some of whom have general skill sets rather than highly specialized or technical ones.

The advice to “be a generalist” is the close cousin of “retain optionality.” It sounds smart and has reasonable parallels elsewhere. You’d never put your whole life savings in a single stock, right?

But keeping all options open whether by avoiding the appearance of specialization or by running from professional “lock in”, has diminishing returns. You’ll wind up treading water and passing on good opportunities for fear of losing your precious optionality.

Being “a generalist” in a generic context doesn’t mean anything. It’s an excuse by people who fancy themselves clever and scrappy enough to do most anything without prior knowledge or experience. So long as “anything” is high status and interesting, that is.

Very often, the Clever Generalist is a recent grad (BA or MBA) looking for Chief of Staff, Biz Ops, or Strategy roles, usually sprinkled with a “bit of product” or “growth but not sales” for good measure.

They don’t necessarily have specific qualifications but they know they’re smart and, more importantly, insightful enough to slot right in and contribute Big Ideas. FP&A or customer service or coordinating the new lease or cold calling prospects or re-stocking the fridge is a waste of their talents. They are “big picture” people looking for big picture work. 

We all know these people. Some of us are or have been them. I certainly have been.

However, in specific contexts and with the right attitude, generalists can be essential: when either 1) resources are so tight that you need people to pick up the slack and fill holes or 2) orgs become big and specialized enough that they need to be forced into cohesion/translated across.

In the first case, the generalist plays janitor and does all the unglamorous things that the CEO has only just herself stopped doing. In the second, the generalist is functionally a project manager, part of the professional managerial class within the company that makes shit work, even if they’re a step or two removed from the doing of said shit.

There’s an animating purpose for the role and a skill set/domain expertise required to do it well. You can’t just waltz in and declare yourself “capable of all things, generally.”

If I left VC, I’d likely work in a “generalist” role. I can do a bit of corporate finance, sales/BD, recruiting, and brute force operations. I can prioritize and manage politics well. These tools have some generalizable usefulness but are *specific* skills built up over particular experience and applicable (at least by me) in only a narrow range of circumstances.

I’d probably have some vague title like BD, Biz Ops, corp dev, GM, etc. Much of my job would be project management. Karl Yang has more on that if you’re interested.

Jon Coffey, a noted MBA and Generally Clever Person, put it like this: people often conflate "cross-functional" and "generalist" but to do most of these jobs you need a specific set of skills and expertise that other people in the organization probably don't have. So find or develop that skill set. Figure out a way to be uniquely, and specifically valuable.

You can have generalist knowledge or a generalist skill set — not both.

Assess opportunities by your ability to make an impact with what you have, whatever that may be. And if all you have is work ethic and smarts, roll with that until you can develop something more.

Start as operations associate, BDR, or finance manager and just fucking crush it. Move up within that org chart. Take on more responsibility and find new arenas in which to apply that skillset and domain expertise.

Being smart and hardworking is not enough on its own. Assuming otherwise (and assuming that people will just recognize your innate brilliance) is a short path to disappointment when there is real, if unglamorous, work to be done.

So don’t be a generalist if you can help it. Build a skillset and put it to work.

---

Many thanks to Jon Coffey for his feedback and edits on this.

2020 reading list

A weird year for books

If 2019 was the year I made a concerted effort to start reading whole books again, it was even better as practice for the nightmare of 2020. This year has been nothing but books, video games, cooking, and work.

Once again, I thought it might be fun to share a bit about what I read this year. Last year’s reading list was almost entirely fiction and mostly science fiction, specifically. 2020 was a bit more diverse but I think it also lacked any of the singular pleasures of 2019. Tl;dr my favorite book of 2020 was probably The Sympathizer.

Here’s my 2020 reading list in chronological order with shout outs to those that recommended each book to me:

Nothing to See Here - Kevin Wilson

This was a really fun one. It’s got an absurd premise - a nanny takes care of the neglected twins of a rising political star who has the unfortunate habit of spontaneous combustion - but pairs that with a really sweet heart. It’s pretty fun and an easy read. If you’ve ever done weird babysitting, this one is for you.

Thanks to my sister Liya for getting me this as a Hannukah last year.

Exhalation - Ted Chiang

Last year I read Story of Your Life and Others by Chiang and it was one of my favorites of the year. Exhalation, another collection of short stories, is even better. The titular story (Exhalation - about a scientist discovering the key to human cognition and its eventual end) wasn’t my favorite but through the eight or so stories, but Chiang is always exceptionally imaginative and entertaining. Despite being a sci-fi writer, he never feels particularly bound by any one style, theme, or type - you’re at no risk of boredom or repetition.

The Spy Who Came in From the Cold - John le Carré

This was the year I really got into John le Carré. I don’t know what exactly got me to finally pick him up after hearing the name for so long but at least some credit has to go to The Watch podcast. I am so glad I that I did get to read him before le Carré sadly passed away just a few weeks ago. He was an absolutely iconic author and master of the literary spy novel, both of practitioner (he served in MI6) and chronicler of the Cold War and the slow erosion of British imperial power. If you want to get into le Carré, you may as well start off here. The Spy really gets at the dingy cruelty and pain of the Cold War. It’s also a great introduction to some of the iconic characters (namely George Smiley) who are mainstays of le Carré’s writing.

Tinker Tailor Solider Spy - John le Carré

I liked The Spy so much that I moved straight into Tinker Tailor, undoubtedly his best known, most iconic work. It’s just such a slow burn and such a painstaking portrait of its subjects: the characters and the British bureaucracy. I was introduced to Smiley in The Spy and got to really spend time with him as a person in Tinker Tailor. It was also pretty fun to watch the movie and read the book in sequence together.

The Plot Against America - Phillip Roth

I bought this one the first week of March in preparation for the HBO adaptation and started reading it as a we went into lockdown. Let me tell you, that was a fucking trip and I do not recommend it. Plot Against America is a speculative fiction about a Jewish family in New Jersey in the 1940s as America succumbs to fascism and home-grown Nazism sympathizers. It’s a painfully tense and anxious build up, made more so by its pre-teen POV character just trying to be a kid as his world falls apart. I found it deeply unsettling and didn’t even bother starting the TV show.

Legacy of Spies - John le Carré

The last of my 2020 le Carré kick, Legacy is one of the last books he wrote at 86. Fittingly, it’s a series of short stories told by wizened retirees from the service to newly minted agents ready to launch their careers. It’s something of a capstone on his writing in that you really feel both his age and that of his characters, and that it speaks to the ultimate futility of the Cold War. It’s rich and entertaining - everything he writes is - but it’s also pretty gloomy. Regimes rise and fall. Young people die. Spies betray each other and defect. Ground is gained and lost. To what end? The world keeps spinning.

The Great Influenza - John Barry

The pandemic really blew up my ability to read for a while. I was so anxious I couldn’t really focus. Reading about the 1918 flu helped, in its own way. Obviously we’re living in a different world and we’re dealing with a different pathogen than we were 100 years ago but reading about how humanity made it through (that humanity made it through) certainly brought me some solace. The 1918 pandemic came at a liminal moment in medical history, just as the germ theory of disease and epidemiology were becoming widespread enough to shape possibly the first scientifically grounded public health response to a crisis. Barry does a fantastic job weaving together that medical history with its political counterpart: the first World War and President Wilson’s determination to preserve public morale, even at the cost of public health. Sound familiar?

Three Body Problem - Liu Cixin

I read the full Remembrance of Earth’s Past trilogy this year. Each of the books deserves recognition on their own but before I get there, I want to address the elephant in the room. Cixin is a pretty brilliant science fiction thinker (maybe not the best “writer”) and I really thank all the people who recommended it to me (Dan Khan, Trace Cohen, Charley Ma, and many others). That said, knowing what I know about the author, I can’t really recommend this series to anyone. Cixin is an apologist for the Uyghur genocide happening in China:

When I brought up the mass internment of Muslim Uighurs—around a million are now in reëducation camps in the northwestern province of Xinjiang—he trotted out the familiar arguments of government-controlled media: “Would you rather that they be hacking away at bodies at train stations and schools in terrorist attacks? If anything, the government is helping their economy and trying to lift them out of poverty.” The answer duplicated government propaganda so exactly that I couldn’t help asking Liu if he ever thought he might have been brainwashed. “I know what you are thinking,” he told me with weary clarity. “What about individual liberty and freedom of governance?” He sighed, as if exhausted by a debate going on in his head. “But that’s not what Chinese people care about. For ordinary folks, it’s the cost of health care, real-estate prices, their children’s education. Not democracy.”

Remembrance always at least flirts with being collectivist propaganda and I understand that being an artistic in China might put Cixin in a precarious position with the CCP but this is a bridge too far. This whole series was/is a bit of a phenomenon this year and made quite a mark on me and my wider social circle. Knowing what I know now really casts the series in a much darker light and I am not comfortable with how influential it is/will continue to be.

Dark Forest - Liu Cixin

The Dark Forest theory itself is really compelling and I’d definitely encourage you to read about it. Here’s an article that lays it out.

The Pioneers - David McCullough

I took a quick break from space (and time) exploration to read about the settling of the Ohio territories. This is just a chapter of American history I really didn’t know much about: the birth of the country as told from outside the halls of power in the capital(s). While it’s not the primary focus of the book, you can really see the battle lines of the eventual Civil War being drawn in the western territories as early as the 1790s and the choices around slavery in these territories. Is McCullough a bit rosy in his view of the country? I mean the subtitle is literally “The Heroic Story of the Settlers Who Brought the American Ideal West”… But I took a few days to read this one and felt like I learned something.

Thanks to my grandmother for this book as a birthday gift.

Deaths End - Liu Cixin

Even if I didn’t have my other issues with Cixin, this one is where the series really falls apart anyway. So if you’ve read the first two, you seriously can just skip the finale. Seemingly as the books got more popular, the editing got lighter. Let me tell, it was missed.

Power of The Dog - Don Winslow

For my Sicario fans out there, this one is for you. It’s a super intense crime thriller set across decades at the US-Mexico border and the escalation of the drug war (and the cartels as global powers). Winslow does his homework and paints a picture. Pick this one up in the morning and you’ll be done by dinner. Trust me.

Thanks to Nat and Henry for pushing this one on me.

Destiny of The Republic - Candice Millard

In middle and high school I had a history teacher, Chris Mellon, who absolutely loved President James Garfield. After reading this book, I finally get why. Garfield was a pretty incredible guy and probably could have been an incredible president had he not been shot by a crazy person shortly after taking office. His death was a catalyst for what we now think of as the modern White House, a renewed respect for medical science, and even the invention of the metal detector!

If The Pioneers seemed a bit cutesy at first reading, it definitely helped me enjoy Destiny a few weeks later. Garfield was born in Ohio shortly after the events of The Pioneers and there’s a direct through-line from that story to his own. Moreover, Destiny serves as a snapshot in time medical history of the US that leads directly into The Great Influenza and the 1918 flu. The germ theory of disease and antiseptic theory were just *ahem* germinating at the time of the assassination and Garfield famously could have lived if his doctors had been more willing to trust the latest research on antisepsis.

Dune - Frank Herbert

In a bit of a theme, I picked up Dune so I could get ahead of the movie adaptation. Turns out I had more time to get through it than I initially thought but whatever. I’m definitely very excited for the movie. A new Denis Villeneuve? Yes please. That cast? Incredible. The fucking trailer? No words.

…Anyway, Dune is great and lives up to the hype. It’s a weird fucking book but if you like science fiction and fantasy (and especially if you like Star Wars, Star Gate, and/or Mad Max) this is pretty much required reading. It’s not nearly the slog to get through that I was anticipating. Despite its age, it’s such an influential book that it feels timeless. It feels familiar because Dune basically created the tropes and language for everything that came after.

Golden Gates - Conor Dougherty

Dougherty tells the contemporary of California housing policy through a series of vignettes and mini-profiles of some of it's principal players. The co-option of environmental protectionism by anti-housing homeowners is the most cutting piece of the story here and deserves more than the one chapter it got. In short, new construction is blocked over environmental concerns even though the resulting sprawl and low-density development does far more harm than mixing concrete ever could. But these are big complicated fights and if you care about the future of cities and the planet, you should spend the time on this compact book.

Picked this one up after Dougherty made an appearance on the Slate Money podcast.

The Name of The Wind

This is just an old school fantasy epic. Very D&D. If it’s your thing, you’ll probably like it. If not, you just won’t.

Nat got me to read this one.

Interpreters as Diplomats - Ruth Ailene Roland

I don’t normally read straight up academic books but after reading a section of this during my sophomore year of college, it’s stuck with me and I wanted to revisit it. This is basically a survey history of how interpreters have functioned in cross-cultural diplomacy. The idea of interpreters not just translating diplomatic cables but basically brokering diplomacy was fascinating. They played (and still do to a lesser extent play) a very active rather than passive role in negotiations, trade, etc. The interpreters were basically responsible for filtering information selectively to bring the two sides together in practice, even if they each had totally different understandings of the context and meta-narrative of negotiations. Who was being differential to whom, which side was making concessions, etc. There’s even instances where the same treaty says conflicting things in two different languages - both sides get to believe they got the best of the deal. Even if the particulars of language have literally changed (and the legal review is a bit more robust), that should sound pretty familiar to anyone who makes deals for a living…

Thanks to my professor Jun Hee Cho for adding it to the syllabus.

The Sympathizer - Viet Thanh Nguyen

I can’t recommend this one enough. The titular sympathizer is French-Vietnamese double (or triple or quadruple) agent during and immediately after the Vietnam War who is both good at and compromised in his role because of his ability to see both sides at once. Darkly (seriously, really darkly) funny and touching. The style is really interpretive or impressionistic rather than literally descriptive, which works to just draw you in. It’s just fantastic.

Thanks to Henry, Ganesh, and Hannah for suggesting it.

The Cartel - Don Winslow

This is the follow-up to Power of The Dog but it kind of lost me. The first book managed to just toe the line between literary thriller and pulpy trash. The Cartel did not. It’s fine as a beach read but don’t expect much more than that.

Upcoming/What I’m reading now

I often like to read works of fiction and non-fiction simultaneously, switching off between the two periodically. Right now I’m reading Dark Matter, a collection of short sci-fi stories by black authors, and Epidemics and Society, which is exactly what it sounds like.

Next up, I’m looking forward to getting into (in no particular order):

• Address Book: a history of addresses and city planning

• Kochland: profiling the Koch brothers and their influence in America

• The Fish that Ate the Whale: a biography of the banana king

• Artemis: the latest book from Andy Weir, who wrote The Martian

But I am very, very open to recommendations for what to read next, especially fiction. Please send em over!

We're hiring

Revisiting my earlier stance that you shouldn't work in VC

Tl;dr - we’re hiring an investor to join our team and you should apply.

Last summer I wrote a post called Don’t work in venture capital. It’s probably the most widely read/popular thing I’ve written on substack and among the most widely read/popular things I’ve put on the internet at all (it’s a low bar but still). 18 months later I still get people hitting me up about it and it still drives the bulk of new subscribers to 99% Derisible.

I suspect that that’s less to do with me specifically and more to do with the fact that venture has a certain arcane mystique. For better or for worse (usually for worse), everyone wants a piece but few people understand what it really means. Pulling back the curtain to talk some shit seems to have struck a nerve.

Now we (my firm, Tusk Ventures) are hiring an investor to join our team. You can check out the full job description here and the application here. But before anyone calls me a hypocrite or tries to score an easy dunk, I want to pull the curtain back again and explain why this opportunity is genuinely different. Even if you shouldn’t work in venture, you should work with me.

Go back and read it in full but, as a refresher, I laid out three basic points for why you shouldn’t (try to) work in venture in the original post:

1. It’s very hard to get a job in venture

2. Most of the jobs are not good

3. You won’t make as much money as you think you will

1) This is a straightforward process

We are hiring openly. There is a straightforward application. The target profile is clearly defined. There shouldn’t be any guesswork.

There is no requirement for schmoozing and networking to get ahead of a process. There is a link to an application that shouldn’t take more than 30 minutes to fill out. I have no interest in wasting your time because the time it takes to read applications and screen applicants is my time.

That doesn’t mean you are likely to get hired (hopefully we’ll have tons and tons of great people apply) but it does mean you’re on an even playing field with everyone else.

2) This is a good job

We’re looking to hire someone to fill urgent needs for real work. We’re a small team, which means that while there’s more scut work to go around (for everyone) there’s also far fewer barriers to making a real impact and rising with the firm. We’re just not an old or big enough fund to have super well-defined roles and process. You get to have a hand in driving that by showing up and doing the work. There’s no swim lanes but the ones you define for yourself. And if you can do that, why would we want to let you move on?

My own career here is the best proof that I can offer. I started as an intern and stuck around because I contributed and had great mentorship. Now I’m a Principal and I have no interest in pulling up the ladder behind myself.

This is exactly the type of job I said you should go for if you’re going to go into venture:

IF you are going to work in venture, try to optimize for partner/fund rather than generic “venture capital.” As I’ve said, most jobs and funds are bad. The biggest brand name funds are functionally impossible to get hired at and working there is unlikely to be any better than what I’ve described above. I’d suggest going to a new fund where you stand a better shot at having upward mobility, economic upside (carry), and the ability to drive outcomes.

3) We’re doing well

VCs don’t generally get the cash comp you think they might. The real money is in the upside but most funds just don’t produce all that much. Venture capital is famous for following power laws whereby a very small fraction of investments (and by extension a small fraction of funds) produce most of the profits for the whole asset class. The average investor lags the public markets.

That’s one of the reasons funds almost never open up their books and talk about their numbers publicly. We did.

So what now

Not everyone is going to be a good fit for this job. Not everyone is going to get an interview. But everyone is going to get honest consideration and a fair shake. And whoever we do hire will have our commitment to create a positive, encouraging environment where you can really grow into yourself as an investor.

If you think you’re interested in the role, apply. If you know someone who might be, send this to them.

I wrote that I got so lucky in so many ways and that my experience is non-replicable that it doesn’t bear explanation. I am offering a chance to replicate it. I may be wrong about everything I’ve laid out but I’ve got skin in the game (in fact I’ve got my entire body in the game) backing it up.