8307 days

Today is Mother’s day 2012, and I always take this time each year to more explicitly celebrate ways my mom has influenced my life. But that usually happens in the confines of a card. This day in this year is also special in that it begins the week that I graduated college last year, and thus also the week that I started this blog.

I was planning to write a one year retrospective on blogging for my official blogiversary in a few days. But I got a little excited and started reviewing my posts early. As I did, I realized how much my Mom has directly impacted the topics I chose to write about, and the thoughts I expressed.

Which is odd, because I haven’t gotten around to showing her this blog yet. But today I’ll change that. So sending her this post will mark the first time she’s actually seen my writing in a while. Henceforth I write to her.

Hi Mom!

It’s been 8,307 days since I was born, and the density of lessons in those days can’t possibly be summarized by one post or the 22 Mother’s Days I’ve celebrated with you so far. But I thought I’d write some of them down for posterity. Here I can also fit more text than I can fit in a card (and you can actually read it, as opposed to my handwriting).

In the past I’ve often written to you on two subjects: things you’ve done that I respect you for, and times you’ve helped me find the right direction. The hard facts of your life — raising me on your own while keeping up with a fast paced career — are eclipsed only by the subjective nuances. You start with being uncommonly at peace with yourself, and layer atop that peace a deep compassion and empathy that makes others feel at ease being around you. You’re at once both strong-willed and gentle, accepting and inquisitive. Simultaneously my ideal role model and my north star.

But none of those concepts are new. What’s more surprising is the subtle way you’ve influenced every decision, action, and thought I’ve had. I’m very much my own person, and you and I passionately disagree with each other on many topics… yet at the deepest level my guiding principles and ideals have all converged on lessons from you.

So here are ten of my favorites. Each underlined link is a blog post, and they can all be traced back to you. Something you’ve said or done in the last 8,307 days that I’ve held onto.

1) Beyrouteys never give up. You repeated this to me a thousand million times when I was a kid, and it stuck. Never giving up implicitly means allowing yourself to fail by trying lots of possible solutions. To “fall forward” as Denzel put it at my commencement last year. When I’m in danger of throwing in the towel, somewhere in the back of my mind you always remind me that Beyrouteys never give up.

This has led me to keep trying at things I previously failed to accomplish. Last year I learned to ride a bike because I had given up on it previously. In doing so, I came to understand the importance of having a safe environment where you wouldn’t be judged or berated for failing, but rather encouraged to push the limits of nature, tools, and yourself a little further. You gave me just that environment. And that’s why I learned to love technology — you can fail over and over and just hit the back button if something goes wrong. Tech culture celebrates failure, and so do I.

2) Disconnect. As much as I love tech, you also helped me realize that it’s a two-edged sword. While it can bring people together, it can also make us even more distant from each other. When you reminisce about your childhood, it reminds me to think twice about how I’m spending my time and what I’m prioritizing. (Amusingly, I once asked you if the whole world was actually in black and white when you grew up).

Even though it seems to you like I’m always on the computer, I take your questions about technology to heart. When a lot my peers let distractions from the internet and social media rule their lives and build up an addiction, I keep my phone on silent and prioritize being in the moment. When I’m thinking of someone, I give them a call and avoid empty online interactions. And even in the hustle and bustle of city life, I often disconnect completely and take a walk. Some of my best memories are when I’ve gone radio silent and unplugged for several days at a time, as when I refinished a table last summer.

3) Take risks. You spent a great deal of your life thinking about risk and protecting against it. At times I know you’d love to insure against everything, but your stories (e.g. missing out on Fender) had a huge impact on my own risk reward curve. You’ve always encouraged taking calculated risks, and adding some random variation to my daily life. For example, you pushed me to “get out there” and meet people when I used to be shy and reserved.

In the past year alone, several of the most life-changing moments happened because I opened myself up to the influence of randomness. When people invited me out to events, I strived to always say yes. I met some of my closest friends that way, found jobs that way, and learned about myself in the process. Sometimes it doesn’t work out, but I keep trying until it does. Today I trust my instincts more than ever before.

4) Defer no time, delays have dangerous ends. I may have learned that Shakespeare quote as a freshman in Mask & Wig, but the point that “anything worth doing is worth doing now” was fundamental to my upbringing. Sure, every parent tells their kids not to procrastinate. But your actions spoke volumes: you dealt with problems immediately instead of letting them pile up. Simple habits, like doing the dishes as soon as you’re done eating, or putting things back after you’re done using them, have stuck with me. Those habits are core to accomplishing long-term goals.

I’m admittedly imperfect at this one, and I’ve realized the perils of fake productivity — when you’re doing the easiest thing rather than the most important. Every time it snowed, you’d head straight down to the bottom of the driveway and chip away at the heaviest, iciest section first. I remind myself of your example when I’ve been wasting time, and attack the most difficult thing on my list first.

5) No makeup. I’ve always loved and respected you for your willingness to show your true skin. Literally, in the sense that you don’t use makeup to tweak your image. But also because you’re never afraid of showing who you are. You don’t cover yourself up to fit what everyone wants of you, and you’re comfortable with acting differently from the rest of the world.

I may only be in my twenties and have a lot to learn, but I am unabashedly myself. All of my friends and coworkers would surely agree that I value things differently than most people, and act on those values. I don’t watch TV because I don’t care about it, and I don’t pretend otherwise. I don’t believe in sending meaningless token gifts. Though many favor brevity over the art of communication, I send long emails when I’m passionate about a topic. And I don’t like coffee, so when people think they need an excuse to meet up, I take walks with my friends instead. ‘Be yourself’ is trite advice, but you’ve lived it in a way that I strive to emulate.

6) Don’t take yourself too seriously. I can go to any group you’ve ever been a part of and find people who love you. They’re not all your ‘peers’. Whether at work or at home, you make people of all walks feel comfortable around you — people more junior to you, younger than you, less intelligent or experienced than you. You’re humble, joke about yourself to light of your actions, and give others credit. You find points of commonality.

This makes you more approachable than anyone else I know, and is an example I follow. It’s easy for people to tell you their secrets and feel connected to you. And, perhaps most importantly, they aren’t afraid to give you feedback and be honest with you immediately after meeting. Since I strive to constantly improve myself, I care deeply about being easy to talk to and open in my conversations. I’ll protect those instincts religiously no matter how ‘high up’ I ever get.

7) Find greatness in everyone and everything. Any place you’ve ever taken me has been an exploration, from the first time I joined you for your commute to work. You asked me tons of questions and let me form my own opinions. (And I now know way too much about airplanes and trucks). You were optimistic, and showed me how to keep searching until I found something worth digging deeper for. You made me try new things constantly, even when I protested, even when they were tomatoes. A tomato was not just a tomato, though. Each of them had slight differences, and we talked at length about the varietals. I may not have agreed with you at the time, but I was listening, and developed an insatiable curiosity for everything.

That curiosity has taken me to the corners of knowledge. Early on, I discovered Wikipedia and was absolutely fascinated by even seemingly dull topics. I learned about the minutiae of everything from law and politics to science and psychology. Behind every piece of knowledge, there’s a story of how it got there. And people have similar stories. Just as curious as I was for information, you taught me to be curious about people. Everyone has something beautiful about their history, decisions, and preferences. So I grew to take conversational risks in hopes of finding every delicious nuance, and have friends from all walks of life and backgrounds because of it.

8) Fun can be meaningful. When I look at the artifacts of your life, I find elegant simplicity. You didn’t buy everything under the sun, and never valued possessions or ostentatiousness. You treated yourself to great experiences, on occasion, and acknowledged that the people you’re with are far more important to your memory of the experience than the things you did. I couldn’t agree more. As people spend time on the things that don’t matter, and create artificial dramatics in their lives, I know that the simplest things are usually the best.

9) Be other-oriented. Perhaps the most amazing thing about you is that, in spite of all you do, you put other people above you at every turn. Small lessons from your actions have made waves in the rest of my life. When we went out to somewhere new, you took the time to learn and call people by name to help them see how important they are to you. You were great to everyone around you, even people you don’t know, and step up to help them when you see something wrong.

You’re great to everyone, and though I’m not sure how you do it, I strive to emulate your example. WWMD is the first thought in my mind when an opportunity to help someone presents itself. And as I experience life, I keep other people at the top of my mind so I can show, tell, and send them things that will make them happy. I know that in comparison to you, I’ll always come up short on this dimension, but you make me want to be a better person every time I think of you.

10) Focus. It’s common knowledge that I have a pretty terrible memory. I blame that on genetics to some extent — we’re both pretty forgetful. Yet you always remember the things that count, and forget the rest. I’ve taken the same approach to my life. Last year, I started this blog with a post called “The backpack, the binder, and the basket.” I wrote it as I organized my papers from school and took stock of what memories I’d actually take away from my classes. The ones I’d choose to carry with me every day, in my metaphorical backpack, were very few.

So as I take stock of the last 8,307 days, and the memories and lessons that I’ve learned, one thing sticks out. The ones worth carrying in my backpack all came from you. I love you mom.

Love,
Jesse

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 accepted for a startup to be like a hookup. You aren’t 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 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 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 constant discourse around startups misses the mark for me. I believe that Roger and Dave are in two completely different businesses. Though their purposes sometimes converge — a tempup, like a hookup, can occasionally become a meaningful long term relationship — their forms, functions, and scaling characteristics are necessarily different to reflect their underlying purposes.

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. Successful companies 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 has a decent chance of getting bought quickly. A small hypothesis test about a market leads to great evidence that a new product has potential and a 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 interactions being shorter-term. Dave related it to making Model T’s, and I couldn’t agree more. They might be less romantic than the highly custom businesses 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.

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 demonstrate almost the exact opposite objectives.

I believe it’s high time to air out those objectives, 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.