Long emails

I have a confession to make: I write long emails. I don’t write them frequently, but when the topic is right, I’ve been known to expound in paragraphs at a time. I compose in stream of consciousness, and go back to edit, restructure, and make cuts. But no matter how much I rewrite and excise the junk, I still end up with hundreds of words.

This is seen as a nuisance by many, and discourse on email best practices often makes me feel guilty for pressing send. Yet in our new tl;dr normal — mobile connectivity, short-form communication, and constant distractions — there’s something deeply refreshing about a long email dialogue. So I will no longer be apologetic about my habit.

How could long email ever be refreshing? Let me count the ways:

The Ladder of Inference

  1. Completeness. You present the whole picture of relevant detail all at once. This encourages consideration of a topic holistically, and systemic thinking before analysis.
  2. Data. You travel down the “ladder of inference” and present not only your conclusions, but the underlying data and assumptions that guided you. Opening up your data allows for reinterpretation, and we can identify differences in perspective on the same observations.
  3. Logic. Writing long-form thoughts activates your reasoning, which helps you to organize complex information, eliminate senseless connections, and achieve greater understanding in the process.
  4. Quality. Taking your time forces you to think deeply, and encourages solitude. Receiving a long email changes expectations around synchronicity, and allows the recipient to sleep on it.
  5. Revision. Stepping away and rereading your email yields edits, reconsideration, and simplification. It also encourages perspective-taking, which in turn helps you better understand your recipient’s point of view.

Even beyond these useful properties, long email reveals something beautiful: your passion. When you have the instinct to write an essay-length message, it’s a direct indication of how deeply you care about the topic. For example, I’ve recently uncovered my intense excitement about disruptive fintech startups by sending long-form thoughts to several founders. I wouldn’t have realized how much I love this area if I had cut my ideas short.

In the process of speeding up our communication, we’ve somehow managed to discourage our passionate thoughtfulness. Brevity and rapid, informal tone is now interpreted as a signal of confidence, rather than of superficiality. Attention span is limited to thirty seconds or less.

Of course, for the majority of email, these heuristics make sense. We focus on getting things done, and use the email inbox as a task list. But this task-orientation makes email glib. For example, the Times recently suggested: “Make one point per e-mail. If you have more than one point, send separate e-mails.” And there’s a whole email charter that asks us to avoid open-ended questions and send only short, actionable messages.

So I propose a more nuanced view: that there is a place for long email in our communication toolbox. Sure, it’s not the hammer or the screwdriver, and shouldn’t be used as frequently. It’s more like that hex key you’ve been saving from your last Ikea trip. Not useful in most situations, but when the right opportunity arises, you’ll be happy you kept it around.

Tempup artists

Tech is seeing its equivalent of the 1960s sexual revolution. Though once taboo, it’s gradually becoming acceptable for a startup to be like a hookup.

You aren’t always interested in forming a long-term relationship, and you don’t want all the commitment, strings, compromises and messiness. Sometimes you’re just in it for a quick sale, and building what I’d call a tempup. The tempup is all about testing a hypothesis quickly, and generating a small but meaningful return for the founders.

But the investor ecosystem hasn’t fully accepted this new normal yet. Tempups still need to conceal their intentions. Even if they truly just want a hookup, they need to use the language of long-term relationships to attract capital. In tempup rhetoric, every market opportunity is still in the billions, every financial forecast is for 3+ years, and every funding discussion is about bringing on the ‘right partner’.

As with sexual liberation, I’ll reserve judgment on whether tempups represent the moral decline of civilization, or the right step forward to a more flexible, accepting society.

To me, there’s a more pressing question: when will we start comfortably talking about reality?

Yesterday, in announcing his new $50m fund for 500 Startups (congrats btw!), Dave McClure asked “why hasn’t VC scaled?” and my colleague and mentor Roger quickly asked “why should it?” in response.

Something about that conversation, and the discourse around lighter, cheaper-to-build startups misses the mark for me. I believe that Roger and Dave are in two completely different businesses. True, their purposes sometimes converge — a tempup, like a hookup, can occasionally become a meaningful long term relationship. But the forms, functions, and scaling characteristics of venture capital firms are designed around the institution of startup marriage, which has a singular purpose. Programs like 500 and many of the startups that join them have different goals in mind.

That trend alone is not alarming to me. Neither business is better or worse, but they are just different and should be acknowledged as such. What’s more worrisome is rise of a “seduction community” in startup-land, whose objective is to ‘hack’ the signals in VC courtship to conceal tempup ambitions.

Before I explain what I mean, let’s review what’s brought about the revolution. Like sexual liberation, it’s sparked by social change:

  • Tech is exiting the growth stage and entering the early phases of maturity. Big, successful companies like Google are cash-rich, but suck at creating and testing new ideas and entering new businesses.
  • Talent in the information economy is difficult to find and assess through interviews, and competitively hard to attract.
  • Starting a company is largely democratized through open-source tech stacks, variable cost pricing for infrastructure, approachable programming languages, and easy distribution on ubiquitous platforms (browser, app stores, social).

These changes make today’s market a perfect storm for building tempups. It’s cheap and easy to start, and your FNAC tempup has a decent chance of getting bought quickly. Your small hypothesis test about a market leads to great evidence that a new product has potential and your team has the right stuff. It can be a win-win for companies and entrepreneurs, and there’s no shame in that at all.

A new breed of investor is evolving to meet this need. They’re structurally set up to fund lots of similar companies and okay with the ‘relationship’ being shorter-term. Dave related it to making Model T’s, and I couldn’t agree more. Today’s more, shall we say promiscuous founders may be less romantic than the companies of times past, but as an investor, there’s money to be made in these tempups too. Just like satisfaction can be found in both hookups and long term relationships. Different strokes for different folks.

Unfortunately, the language of entrepreneurship is set up around romance, and investors still mostly look for the signals that a company is going for a grand slam rather than a base hit. And that’s where it gets dirty. Enter the tempup artist.

Remember back in 2005 when an entire generation of guys obsessed over Neil Strauss’ book The Game? It was about his forays into the seduction community, a shadow world of “pickup artists” who hacked the signals of social value and attraction to convince women to accept their advances. Men attended a bootcamp, where they were trained on all the right body language, social proofing, and psychological tricks to get women to chase and fight for their attention.

Sound familiar? I don’t think it’s intentional, but accelerators have taken on some striking parallels to seduction bootcamps. You work in an intense environment, refining your pitch into a ‘routine’ with all the right signals – exponential curves (peacocking), paying customers, angels and advisors for social proof, and war stories about how you got out of the building and pivoted to prove your resilience. You demo, work the room, and show that you’re the real deal and going for a grand slam. You make yourself artificially scarce, and go for the holy grail: a big-name VC putting their money in unprotected at a high price.

Sure, all courtship involves putting the best foot forward. Everyone has their game, for sales and deals and jobs, just as much as for sex and love. Dancing the dance is fine when there’s a shared long-term objective. But tempup artists are insidious, in a kind of sociopathic way, when they know their companies aren’t remotely in it for the grand slam. TUAs wrap their true objective (a quick, life changing exit) in the signals and qualities that indicate almost the exact opposite objectives.

I believe it’s high time to talk openly about those true intentions, and make sure all parties involved are playing for the same reasons. Of course, I know perfect clarity is tough to ensure because motivations change — you may think you want long-term right now and later decide it was actually just a hookup. So the best we can ask for is honesty at all times. Things get messy when expectations aren’t voiced actively and often.

So when Dave asks why VC hasn’t scaled, what I hear is “why hasn’t everyone adjusted to tempups”. And I think the answer is that, like hookups, they’re not right for everyone. The values and likely outcomes are different.

Certainly more investors will enter the market over time, with funds structured to have the same goals as tempup founders. They’ll fund thousands of startups like Dave envisions, and be okay with most of them going after small markets and smaller but faster returns.

But in order for that to happen, we need to change our discourse and acknowledge the quantum differences between these strategies. Just like there’s room for both hookups and serial monogamy, tempups and long-term ventures can coexist in the world. So long as we can discuss them openly and make sure the objectives are consensual.

Via xkcd.

Trust in randomness

Pause for a moment and think about how you got here. Not here in the sense of “your chair”, but rather this particular juncture in your life. Call to mind the stories of how you met all the important people in your life: your roommates, significant other, boss, best employees, best friends, greatest mentors, and anyone else who’s meaningful.

When I do this exercise from time to time, I’m overwhelmed by the impact of happenstance. Every important relationship seems to be hanging by a thread of universal ether. I can almost feel fate’s strong pull in every memory that took two or three completely chance events to land me next to someone who hugely influenced my life. It makes me cherish those people even more to think that a tiny delta could have prevented us from ever meeting.

But it’s easy to forget that chance acts quantitatively. For every one instance where random events led me to a relationship of consequence, there were a thousand other random events that led to nothing. All of those get washed from memory, leading to the availability bias that we call fate.

Have more fate

Outcomes we ascribe to fate have two key qualities: chance and significance. Since we can only know significance (a measure of quality) in hindsight, the best we can do to experience more fate is to experience more chance.

Fortunately, the fateful event that changes your life has a beautiful contrapositive: a meaningless event that you completely forget, having no impact at all.

Think about that for a second. For the math-inclined, you’re sampling from a distribution that looks like this:

Yet, you have almost no sampling cost. If you experience more events, the vast majority will be mediocre and you’ll never remember them. A tiny few will change your life, and you’ll call them fate later on.

What about time? Shouldn’t you value not wasting your time on meaningless interactions so you can spend more time on the things you care about?

That concern is important, but you’re probably nowhere near the edge of that marginal trade-off yet. Consider the quality of your most fateful interaction, as a function of how many interactions and events you’ve experienced. I’m willing to bet that your curve looks like this:

The more times you drink from the fountain of random life events, the greater your best, most important outcomes will be. Being in the right place at the right time is mostly a function of being in lots of places.

(If you happen to have taken product design, you’ll note this is all adapted from Karl Ulrich’s book on Innovation Tournaments. Life events, I’ve realized, are extremely similar to ideas — the more you have, the better your best gets.)

Follow the white rabbit

Let’s make that more concrete. I’ve heard so many people complain about falling into patterns of normalcy. The complaints are embedded in different forms. “There aren’t any jobs out there for me” or “there are no quality women/men in this damn city” are common ones.

If left to its own devices, aging slowly takes its toll on our openness to new experiences. If you’re currently a slave to normalcy, take a look at how you’ve been spending your time: is it mostly with the same people, in the same places?

There’s an easy way around this: just increase the quantity and variance of things you try.

But how? Your first step is to adopt an openness mindset. It means always erring on the side of saying yes and being uncomfortable.

I’m no stranger to the ease of being lazy. When you’re done with work every day, you’re tired and just want to veg out. You’re busy during the day and there’s no way you have time to take lunch away from your desk. There’s every reason in the world to say no to opportunities that present themselves. But when your friends invite you out to drinks at that new bar, or a coworker says you should meet someone new, or you can go to that conference or house party or whatever, an openness mindset means that you say yes.

When you say yes more often, you’re sampling more from that distribution.

Trying more new things alone can dramatically improve your life events. But if you want to spend less time and maximize the effect of fewer samples, you have to push out of your comfort zone. When you’re at that dinner with five acquaintances and one person you’ve never met, sit across from the new one. Skip the boring opening dialogue and take a conversational risk. Go to a concert for a genre you’ve never listened to before. Apply for that job you’re completely unqualified for. Ditch your coworkers at that networking event and sit at a table of new faces.

When you stay uncomfortable, you’re stretching the distribution, and increasing the likelihood that your sample will be from the amazing side of the curve.

Which is why “trust in randomness” is all you need to remember.

So next time you feel yourself about to say no to an invitation, or clinging to experiences and people you’re already comfortable with, think of the openness mindset. Take the red pill this time, and see how deep the rabbit hole goes.

Eye in the sky

The Internet runs on recommendations. “You might also like” may as well be the web’s universal slogan. Whether it’s similar items on Amazon, a related article, or a friend-liked-this ad on Facebook, recommendations have become almost invisible to us while we surf and click away.

Yet I’ve recently found myself recommending jobs, products, and connections to friends manually, in real life, on my own, every day. What gives?

Unfortunately, as good as computers are at choosing things we might like, their suggestions are no substitute for actively thinking of people you know.  If web companies had their way, we’d be completely selfish and isolated from the world, passively observing each other and deciding what content to take in, products to buy, and places to go, only because they told us so.

We need to fight back, and constantly looking out for each other is the only defense we have.

The I

It’s a powerful idea for brands and retailers: just ingest as much data as you can about your users, do a little machine learning magic, and voila. Instant increases in engagement, conversion rates, and sales.

But the ingestion part is predicated on us generating a lot of data about ourselves in the first place. And boy do we ever. Entire companies and technologies have been built to collect, analyze, and apply insights about us from the data trails we leave around the Internet. It’s frequently referred to as our “data exhaust”.

Of course, the operative word is ourselves. All our activities online are about expressing the I. Inwardly, it’s I want to see (a click), I want to buy (a wishlist or cart), and I want to remember (a bookmark). Outwardly, it’s I want to share (a post), or I enjoyed (a like) or I read (a tweet) or I visited (a check-in).

All the best companies have perfected the art of beckoning you to express your I. They’re trained to elicit our self-interested actions and enable us to express ourselves better, which indirectly accrues value to the community writ large — what Vin Vacanti calls “The Invisible Hand of the Internet“. The more frequently you pick up an app to show the world what you like, the more data exhaust they have to harvest.

Modern Joneses

If the invisible hand is going to take care of us, why should we be worried?

Let’s look at what’s really going on. Social media is espoused as being all about engaging with each other: we comment, we @ reply, we give feedback. But that’s only the tip of the iceberg. Fred Wilson calls it the 100/10/1 rule. Most people online will lurk on the sidelines, watching what others do and read and like and buy but not engaging at all.

Presumably, recommendations are meant to be that invisible hand on the Internet. Web companies will use your friends’ and strangers’ self-interested data to extract all the best stuff for you. So all you need to do is keep lurking, watching what’s recommended, and your life will be taken care of.

That kind of passive observation is our new form of keeping up with the Joneses.

Other-absorbed

No matter how accurate online recommendations get, there’s always an element of serendipity about someone else just so happening to like something because you do. Relying on detached observation alone leads to missed opportunities when something is perfect for you but not for me.

If you need proof, just think of everything you’ve loved, everything that’s changed your life. I bet you’ll be hard-pressed to name one of them that was recommended to you by a web service.

Our resistance, then, is being intentional. It’s every time we reach out to a friend and say “hey there, I saw this and think it’d be great for you”.

As humans, we’re capable of empathy and perspective-taking. Meeting and learning about someone affords us a tacit understanding of their needs, desires, hopes, and aspirations. While computers can be good at mining what we say, they’ll always miss the parts that go unexpressed or even unrealized. And they’re susceptible to a filter bubble.

So don’t let your friends become dependent on arms-length recommendations. View your world — every interaction, every observation walking down the street, and every thing you try out — as an opportunity to connect with a friend. Who would benefit from this? Who would it inspire? Who’d die for this job? Who would love to meet this person?

You can start with small steps and triggers. Next time you’re about to hit the ‘like’ button, stop yourself and send it to someone who’ll love it instead.

Truly watching out for each other is the essence of our humanity. The invisible hand may get stronger by the day, but it’ll never have eyes.