The Customer Domain Expert

Founders with many backgrounds can be successful, but there’s one archetype I most enjoy working with: the customer domain expert.

These founders have already worked in the industry the startup will target. They have informed opinions on the industry’s players and future. Moreover, they would have been the buyer or user of the product, if only it had existed.

Customer domain experts enjoy several advantages:

  1. Knowledge of the dead ends. They’ve seen other startups fail and know the root causes. They avoid wasting time on misguided features, target customers, partnerships, and vendors.
  2. Informed opinions on competitors. Anyone can read a Gartner report, but customer domain experts have tried competitors’ products, met the sales teams, seen successful and failed product roll-outs, and can separate real differentiation from marketing fluff.
  3. Access to customers. They can just ask questions of peers rather than guessing. Initial sales come from former colleagues or clients with trust.

These founders can move confidently through the uncertain seed stage. They can act in the face of ambiguous and conflicting feedback. They know what objections to take seriously. And they hire and work with the right set of people from the industry.

If you’re a customer domain expert, you’ll know it. A few things set you apart in the earliest days.

You conceived of your company by writing a detailed comparison between the product you’ll build and your competitors. Your sales funnel started with a rank-ordered list of the top twenty potential customers; you knew the inclusion criteria by heart.You personally know your first five customers – they’re peers or clients who heard you were getting started and are already eager to try your product.

As an investor, it’s a joy to work with a customer domain expert. They’re unfazed by early stumbling blocks because they know what to build, who to sell it to, and why they’ll buy. They test the hypothesis behind the business fully. And that is all an investor can ask for.

Writing is a horse; I’m back on it again

I wish I could start with some great reason for my disappearance.

I first wrote about practicing in public in 2015, after I came back from a silent meditation retreat. I sat for ten days with only my thoughts, and I realized every limitation to writing was in my head. I love writing and I was determined to make it a part of my daily life, fears be damned.

What happened next?

I haven’t written publicly again for four years. I fell off the horse.

To celebrate, I want to describe the four constraining beliefs that held me back.

1) I have to keep up my writing

Here’s the first imaginary rule. As soon as I start something it has to be a thing. I have to decide on a blogging frequency, commit to it, and stick to it. As soon as I publish anything, I have to think about what I’m going to publish next and when I’m going to fit that writing time in.

2) My thoughts must be new and acceptable

I have to scour the whole internet to make sure no one has already said what I’m about to say. If someone else has said it, they must be quoted. I have to make sure my thought is expressed inoffensively, inclusively, and exhaustively. I must prove my point with statistics, and avoid overgeneralization or bias or missing some corner case. Or I will be called out, brutally, and never allowed on the internet again.

3) I have to participate

I have to share my writing on every channel for it to be found. Twitter, Facebook, Medium, LinkedIn, a Substack newsletter. All of these channels will generate responses, and I have to monitor and respond to all of them actively. Every response requires thought and stealing my attention away from the rest of my work.

4) I have to get everything else done first

If there are emails unanswered, to-dos unfinished, then I have no right to be writing a blog post. Every other commitment must be prioritized over writing. Inbox zero never came. So neither did opening a blog editor.

Here’s the thing. These constraints did not come from reality. They’re just writer’s block in a sneaky disguise.

No one has once told me that I’m a failure if I don’t write at a regular frequency, on insightful topics, with extensive research, and unique, correct, exhaustive opinions, and respond to everyone who reads it, only after I’ve finished all my other work. 

Laying it all out into a single sentence made me laugh. Thanks, inner critic, for a run-on of reasons why not to write. 

Thank you, real person in the ether — for reading this, accepting me, and proving the fears are just fears.

I owe a huge thanks to every friend who’s ever reminded me to get back to writing, and especially Dan Shipper and Teresa Man for the final push to just publish this.

Vipassana background and FAQ

I went on a ten-day silent meditation retreat to kick off 2015, and my last post explained a few ways it changed my outlook when I returned. Though meditation is mostly a personal thing, I’ve loved talking about it publicly. My intent isn’t to promote it. Being proactive has helped me to (re)connect with more experienced meditators I can learn from, and reinforces my motivation to practice by taking inspiration from others.

Thinking about my own experience, and matching it up with what I’ve heard from others, three things have surprised me about meditation:
1) Even the busiest-seeming lives fit a daily practice. Parents of infants, business executives, prime time TV watchers. People with real obligations make time for it.
2) It’s not just for new age-y “spiritual” types. Regular people just like you and me meditate. Try asking everyone you talk to for a week, I bet you’ll find lots of people you’d have never expected meditate – just as I have.
3) Little changes matter most. It’s not about finding the meaning of life. Mindfulness creeps into your day-to-day in subtle ways, like eating a little slower, fidgeting a little less, focusing a little better, taking criticism a little less personally.

So if you think you might want to try it out, I hope my answers to a few questions might help.

What’s vipassana meditation and how does it relate to other styles?
Vipassana as I learned it is a meditation style derived from one branch of Buddhism called Theravada, and in particular a lineage of Theravada that evolved in Burma (Myanmar). The technique focuses on awareness of your natural breathing and sensations all over your body, and doesn’t involve chanting Om and such. You can read all about Vipassana on or on Wikipedia.

In the US, vipassana is taught in several ways. There’s the “Goenka school” form with 10-day retreats, which is what I tried. There are also several other schools of the same general technique, including a popular version called Insight Meditation (e.g. IMS in MA and Spirit Rock near SF which are very well-known). I haven’t tried any those or any other schools in earnest yet, so I can’t speak well to the differences, but there’s plenty of info online.

Who taught you vipassana?
The technique was taught to me “remotely” during the retreat, by videos and audio of a man named SN Goenka. He’s deceased, so I use the term remotely in a loose way, since he was was filmed in 1991.

If you’re interested, the material for the course is open source. The videos of Goenka’s nightly discourses (talking about the philosophy of vipassana and some practical advice) are here under “Vipassana Discourse.” He takes his time talking so you might find them frustrating – faster text summaries are here. Goenka has also answered a lot of questions about applying vipassana in life, which are listed in an extensive FAQ here. He also chants in a dead language called Pali often during the course which is translated here

What are some issues with vipassana and the Goenka school? 
Just like anything else groups of people do, vipassana is flawed. As an eternal skeptic, I think it’s important to examine the issues in depth and with an open mind. The best critical piece I’ve read is here. You’ll find a ton more if you google vipassana + criticism. Please read them if you’re considering trying this.

In short, Goenka’s vipassana is problematic in several ways. It claims to be “true” Buddhism when there is no such thing. It has a lot of unnecessary rituals and orthodoxy, and some aspects that help ensure it spreads itself, just like any other religion, cult, or viral idea. Also, practicing the technique to could exacerbate depersonalization / ego dissociation, a sense of detachment from the self. In some cultures dissociation is natural and even desirable, and in others it’s viewed as a mental disorder. I suspect there are a lot of shades in between. Finally, any action to clear the mind and calm down all random associations can potentially stifle creativity. Balance is required.

Where did you go on this retreat?
I went to one of many of the Goenka-led vipassana retreat centers around the world for a ten-day course. The full list of them in the US is here. Mine was called Dhamma Siri (Dhamma = truth in Buddhism, i.e. the state of things as they are; Siri = prosperity). It was in Texas, specifically a small town near Dallas called Kaufman. The property was juxtaposed by farms with cattle and coyotes and all.

Why Dallas when I live in NYC? I’d love to say it was because I wanted to get in touch with pastoral times or something. But really, a friend had gone to Dhamma Siri. And I mistakenly thought Texas was warm in the winter so it’d be a break from NY. I was terribly wrong on that one. Thankfully, cold is just a sensation 🙂

How much does it cost?
The vipassana retreats are completely free (the program, housing and food for 10 days – but travel is on you), and all the people who work there are volunteers. You’re not even allowed to donate until after you attend, and they don’t pressure you much or even give you a “suggested donation.”

The free nature of the program helps in a bunch of subtle ways:
1) you feel less entitled to special accommodations when you’re not paying for it
2) dealing with things that aren’t exactly the way you want is part of the point
3) depending on others’ kindness is deeply humbling and helps dissolve your ego

What are the rules?
The ten-day Goenka retreat is an extremely strict environment, monastic even. His stated reason for this is to provide a strong foundation for quieting your mind — minimizing external stimuli and any ‘immoral’ actions like stealing, lying, killing, or sex (?) that can cloud your mind.

I felt the “strong foundation” was generally helpful to achieving meditation, and the reasons for it were mostly true to my personal experience. But a critical view of the stricture might say this facilitates a cult-like atmosphere and makes your mind more malleable for brainwashing.  I’ll leave that to you to decide. The full code of discipline is here if you’re interested.

What’s the day-to-day like during the retreat?
Every day you wake up at 4am and sleep around 9pm. There are three hour-long meditation sittings in a meditation hall, and four sittings of an hour or more that you can choose to do in your room (i.e. fall into a nap often…) or in the hall (if you actually want to practice, which you’ll get more serious about toward the end). There’s a nightly discourse for an hour. The full schedule is at the bottom here.

Logistically, you’re separated into male and female dorms and have no contact with the opposite sex the whole ten days. You can’t read or write, can’t talk, can’t use your phone or computer or the Internet or anything really. It’s meditation all day erryday. Surprisingly, I didn’t miss these much after day 1.

Food-wise, you eat breakfast every day at 6:30 and lunch at 11. There isn’t a real dinner, but a quick tea and fruit break at 5pm. In the beginning everyone is stir crazy about this and takes as much food as they can for breakfast and lunch. Toward the end you realize hunger is a state of mind and has to do mostly with eating speed. What would’ve felt like a tiny portion on day 1 would feel impossible to eat in an hour by day 9. And it’s nothing fancy, but pretty good food when you savor it.

What’s the hardest thing about the retreat?
This is honestly different for everyone. A lot of people say it’s sitting for 10 hrs a day with no back support. While I have a lot of back pain, my legs were never a problem and I pushed through the back pain. I also had no problem with the silence and isolation — I personally found a vibrant internal monologue in between (and sometimes during…) meditations and really enjoyed the time with my mind.

For me, the hardest part of the whole thing was actually not being able to write. I found myself constantly wanting to jot down thoughts and had some of my most creative moments during meals. It was painful not to be able to capture them.

The reason you’re not allowed to write is, ostensibly, so you don’t waste your time thinking about what you want to write and focus on meditating. It also helps you to stop always engaging with every thought that comes up. I understood that intent, and found it useful in some ways, but still wished that I could write a little bit. If I go again, I’d probably cheat on this rule, honestly.

How did you hear about it?
My inspiration to try a retreat came primarily from trusting in the experience of two close friends (thanks Sameer and Eugenia!) who’d gone on vipassana before me. After I heard about it twice from them, I started mentioning vipassana frequently in conversation, and met many others who’d gone as well.

Had you meditated before?
Not at all. The day before my retreat, I could barely sit still for ten minutes or so without opening my eyes and checking the time. I was freaking out a little that I wouldn’t make it.

What made you jump into an intense silent retreat? Why not ease in?
My reason was very personal. I felt like I hadn’t ever done anything that was truly difficult for me and seen it through to completion. I would always give up and rationalize it. Ten days was a challenge to myself, to stay determined.

After the fact, I think jumping in really helped me. It was a boot camp environment, where I did nothing but learn this technique for ten days, 100 hours of meditation. Normally putting 100 hours into anything just wouldn’t happen for me. I’d try something for maybe 5-10 hours in a year and then “life got in the way.”

Think about the last time you bought equipment for a new hobby you were sure you’d prioritize, and it’s now gathering dust somewhere. You can counter that effect by isolating yourself to focus on just. one. thing.

How can I get started in meditation?
You could certainly go my route and jump into the deep end. I’d recommend it, but I’m biased. Meditation centers of all different styles are everywhere, just google your city. As a starting point, there are Shambhala centers (teaching the Tibetan meditation style) in tons of cities listed here that offer intro classes. Another great lightweight way is to try out an app called Headspace – which starts off with just a ten minute practice each day.

Would you go again?
In a heartbeat. In spite of all the flaws and challenges, I thought the retreat was immensely valuable and I want to make it a yearly thing. I’m not sure if I’ll go on another Goenka retreat first, I might try a different style retreat next year. Or maybe I’ll go in another country.

On a related note, I also realized from the retreat how much I genuinely enjoy time alone. I’m an introvert, so this makes sense logically, but I was always a bit apprehensive about traveling alone or taking a weekend off the grid to myself in the countryside somewhere. Now I plan to do just that on a regular basis.

Of course, I’m only a week into my practice post-retreat, so I’m still in the honeymoon phase. The real test of this will be if I’m still practicing and still want to go again after more time has passed. Talk to me in a year.

Everything changes, but I hope meditation will become a constant in my life.

This post is part 2 of a series about my learnings from vipassana. Part 1 on my top three learnings is here.

Practicing in public: what I learned from ten days of silent meditation

At 4am on January 1st, I woke up in the new year to the sound of a gong. As I showered in the first bathroom I’ve shared with twenty guys since freshman year of college, I was immediately confused by the absence of want. I was without so many things that — only a day prior — were critical ingredients in my daily life. How could it be possible that I didn’t miss them? I didn’t have my phone or internet access; and thus couldn’t read my email, check my friends on facebook, or exchange happy new year texts. I couldn’t Google or Wikipedia my questions, or jot down my thoughts (massive handicaps if you know me well). I didn’t have my apartment in NYC, or books to read, or music, or a camera. I couldn’t exercise my body, or eat meat. I didn’t have money, or at least my money was temporarily meaningless. I had no family, friends, or coworkers. And most of all, no voice. I’d maintain complete silence for almost ten days.

I’ve been back for a week now. And while those life gaps didn’t bother me at all during the retreat, you might also be surprised by my lacks upon returning home. I didn’t feel the need to shave my head and renounce my worldly possessions or join a monastery. I haven’t become a Buddhist. I wasn’t liberated from my humanly urges. I’m not changing jobs or moving out of the city or becoming celibate. I have no desire to convert you or to convince you to meditate.

And in some small way, I’m both lacking me, and have more me than ever.

In short, this isn’t “that” story, the one you might have expected reading the title. I’m writing this post to answer a few curiosities that both you and I likely share in common. Why on earth would I remove myself from reality for ten days of the hardest mental work of my life, instead of taking a real vacation? What did I discover while I was there? And how has it changed me now that I’m back?

Lesson 1: You won’t (really) learn anything from reading this post

First off, I’m probably just like you. I hadn’t ever meditated before this retreat. In fact, I could barely sit for 10 minutes of silence right before I left. I’ve never formally studied Buddhism, and I knew very little about Buddhist teachings or even this specific technique prior to getting on a plane. I’m still an extremely imperfect meditator. Sometimes I sleep in rather than practicing. My mind still wanders. I scratch my head when it itches from time to time. So don’t look to me to explain how to become enlightened or anything like that. Instead I’m just going to describe how I experienced meditation and how it’s helped me thus far.

The specific style of meditation I learned is called vipassana, which means “insight into the true nature of reality.” It was derived from the Theravada strand of Buddhism that originated in Burma, if you’re curious. It’s historically interesting in a bunch of ways and flawed in a bunch of ways. That’s about all the context that matters. So I’ll put the rest in a separate post.

Why doesn’t anything else matter? The first important (yet obvious) lesson I learned was about knowledge itself. The only real knowledge is experience. While there are three sources of knowledge: other people telling you something, reasoning through something logically, and directly experiencing something, they aren’t created equal. Even here in this post, I’m recounting my direct experience, but for you it’s just “other people telling you.” So, sad news: no matter how many times you subject yourself to reading my long-ass essay, you won’t truly “get” what I learned from vipassana. Even if you understand everything I say.

It was hard for me to write that last paragraph. The greatest delusion I’ve held in my life is that I could borrow others’ knowledge. I wanted to believe that reading others’ writing and reasoning through it constituted wisdom. And that’s a convenient interpretation for me, since I’ve practiced reading a lot. But in truth, reading-wisdom is deeply limited. The best way to know something is to do it.

And thus my answer to why I went on a vipassana retreat. It meant actually doing something hard, rather than just reading about it. For the first time ever.

Lesson 2: I hate(d) practicing

I haven’t read Ben Horowitz’ book, but to me, the hard thing about hard things has always been that I can fail at them.

When I was younger, my mom was kind enough to buy lessons for me to try out all kinds of cool hobbies. I had a couple years of baseball and soccer and dance and piano and probably ten other things I’ve since forgotten. Maybe I was good at some of them and made fast progress for a little while. But eventually, inevitably, I would fail. Everything would be going well but then I’d get the wrong note in a chord, or miss the ball, or fall flat on my face. In fact, practicing was defined by these little failure moments. So eventually I’d get fed up, and I’d tell my mom (or rather yell, in a tantrum): I hate practicing.

Why did I hate practicing? Because I hated failing. And why did I hate failing? Because it was shameful. It wasn’t mere embarrassment, like “that move was wrong,” but something deeper. It said something about me. I was wrong. I failed.

And boy did I ever hate failing. To fail was to cut against the image of myself that I’d so carefully curated in my mind and the minds of others: that things always came easily to me. That I was always in control. So after a shameful failure to pick it up in elementary school, for instance, it took me fifteen years to try learning to ride a bike again.

Practicing meditation during the retreat was a painfully obvious example of just how irrational my fear of failure could be. Imagine this: I’m sitting in a dark meditation hall, filled with fifty others who can’t make fun of me to my face or behind my back, since they can’t talk. And moreover, they must keep their eyes closed. And they’re all struggling too. Yet still, every time I had a weak moment during a meditation and had to adjust my back, my instinct was to feel ashamed. So ashamed that I wanted to get up and leave. For what?

The second big lesson is that struggle isn’t shameful. On the contrary, I learned that struggle is the definition of practice — it’s completely impersonal and doesn’t say anything about me. That’s helped me change my language around practice. Before, I might have thought “I suck at that” or “I failed at that.” But now I think, “I haven’t practiced that yet.” And that’s not euphemism. What separates greatness from fear is merely a strong determination to keep practicing (adhitthana). When I see greatness in others, similarly, I now know “they’ve practiced that a lot.”

Coming home, this helped me feel deeply energized and free to retry all the things I’ve been avoiding for all this time. This past week has been the most experimental in recent memory. And when I’m not so worried about holding up an image of “Jesse can do everything” it makes asking for help a lot easier. Whatever it is I can’t do today, I just haven’t practiced it yet.

Lesson 3: This will also change

A ten day meditation retreat was the epitome of something I could fail at. And I almost did, particularly on day four. I had a little breakdown after the full vipassana technique was revealed, and thought about leaving. But I was saved by that night’s discourse. The teacher lectured on the fundamental truth of all things: impermanence. Nothing lasts forever. That’s what convinced me to stay.

You see, the retreat itself was an example of that fundamental truth. The course was defined by its predictability. It lasted exactly ten days, and I knew that I’d be returning home from the same airport, on the same airline, on the eleventh day. And zooming in further, every subcomponent of the retreat was predictable too. Each day started with a gong at 4 and ended with me getting into bed at 9. Each meditation hour began with sitting down and ended with a chant. The whole thing was just like the first time I heard The Aristocrats — I knew exactly how it’d end… and that it’d end. All that changed is how the spaces in between got filled.

That’s precisely what vipassana teaches. Life is the same way as the retreat, the same as The Aristocrats. We know that we’re born and that we’ll die. That’s neither an optimistic nor pessimistic thought, just a real thought. And it’s a very powerful thought. Every moment begins only to end.

The vipassana technique proves this grand point of impermanence through the microcosm of your own meditation. You can literally experience moments and feelings rising and passing away by meditating.

There are two concepts to help you directly experience this impermanence. First, you learn complete awareness of your natural breath and the subtle sensations everywhere in your body that are happening at every moment. Yup, everywhere.

I’ll try to show you. Stop reading this post for a whole minute, close your eyes, breathe, and think about what you can feel in your left knee. The whole time, without moving it. Keep your attention on your knee and nothing else. Seriously. Like really really. I’ll wait.

What happened? Maybe you could feel the touch of your pants or something. Or a stinging pain. Or an itch. Or maybe you couldn’t focus on your knee. Or maybe you felt nothing. Vipassana meditation is like that, but everywhere on your body. Part by part, moving your focus around for an hour at a time. There’s no chanting “Om,” no physical yoga contortions, just you and your breath and your body. Awareness shows you that there’s always something happening right now, and if you pay attention you’ll notice it.

The second concept is maintaining equanimity in spite of whatever sensations you feel — i.e. keeping your mind completely balanced and free of any blind, automatic reactions. Our reaction patterns are so deeply ingrained that it’s hard to notice them, but they’re always present. For example, try to think back to what made you open your eyes when you were focusing on your knee just now. Maybe your head itched and you scratched it. Maybe your back hurt. Maybe you thought about whether you’d gotten a text message. Whatever it was, that thought or feeling or sound was a sensation, and you had an automatic reaction to it… by scratching the itch or looking at the phone or whatever.

By playing this ‘game’ of feeling a sensation, noticing my automatic reaction pattern, and training myself not to react that way, I learned that my reactions aren’t actually automatic. I’m responsible for how I feel, and I always have a choice. Like my back pain while sitting up straight for hours on end, no matter how extreme a sensation, it’s still impermanent. The few meditations where I chose not to react, never adjusted my back, I left feeling totally calm. A crisis might last for a few minutes, but eventually it’d go away.

That was the third big lesson – everything changes. Really, everything. No sensation or thought or feeling is permanent, and no habit of reacting to those sensations is automatic. You always have a choice of feeling the sensation but not reacting instead. You train yourself not to react by constantly repeating: anicca, anicca (“everything is impermanent”, pronounced like “anit-chah”).

Whatever is, is only right now.

Soberingly, this applies to both pleasant and unpleasant stimuli. The source of all our unhappiness occurs in the instantaneous little moment after we experience any external sensation. In that moment, our default is to form an automatic reaction, regardless of whether the stimulus was pleasant or unpleasant. We crave the good stuff when we don’t have it, and want the bad stuff to go away when it’s there.

Any difference between our desired state and our current reality makes us unhappy with the present moment as it is. For instance, during a meditation, I might be experiencing pain because my back muscles have been flexed for an hour. But I don’t have to make myself unhappy by wishing they were relaxed. The source of unhappiness isn’t that external thing or that pain. It’s our automatic reaction to it. We can change by taking responsibility for our reactions.

That’s tough to put into practice outside of meditation, but I’ve seen it enter my life in subtle ways in the last week. Waiting in line when I’m in a rush doesn’t make my blood boil. I don’t curse if I miss my train. Forgetting my umbrella and walking in cold rain doesn’t make me shiver or worry that I’ll catch pneumonia. And similarly, eating that chocolate or getting some small win doesn’t make me yearn for the next one. I remind myself, painful as it can be sometimes. Anicca. Anicca.

It’s bad right now. It’s great right now. Every statement should end with right now. Things that happen aren’t happening to me, as if I’m the center of the universe. They’re just happening right now. Bad or good, this too shall pass.

The gong, for awakening
The gong, for awakening

Practicing in public

I’ve learned these lessons directly by meditating. I need to experience things for real rather than hiding behind books. It’s not shameful to struggle. And everything changes, so my reactions are my responsibility. Yet I’m also not perfect at applying them by any means. There’s still a ton of work to be done.

Case in point: it took me a few hours to write this post, but a week to start it. That’s a small symptom of a larger problem — this is my first time writing in five hundred days. It’s not for a lack of ideas, since I spent every day at the retreat imagining all the things I’d want to write about when I returned. In fact, I even cheated at one point and tried to write on day 8, only to find my pen didn’t work (hilarity ensued, ask me about my ballpoint ink extraction experiment and the flashlight). And I’ve started hundreds of posts in the last year but never brought myself to finish them.

There are plenty of excuses I could make for myself not writing this week just like all those other days. Sure, I wanted to experiment with integrating vipassana into my daily life before telling you about its benefits. Sure, I had a lot of email to catch up on. Sure, I’ve been getting up at 5am (or so) most days. Sure, it was cloudy on a few of them.

Really, my delay is my own doing, not some external thing. It was the same old fear of failure creeping up again. The truth is, I’m not a perfect vipassana meditator, or an enlightened and liberated one. Ego still gets the best of me all the time. I try to stay equanimous, but sometimes I attach myself to the outcome of becoming a great meditator. When I’m not always making what feels like progress, I feel ashamed and that leads me to avoid practicing. Same old me.

And the truth is, similarly, I’m not a perfect writer. This post is incomplete in so many ways. I didn’t get to half the points I wanted to make. Yet it’s also way too long. Fuck, most people won’t even read up to this point. They’ll give up and think I suck at writing. And the structure isn’t symmetrical. And shit, I’m still just using a WordPress default theme. How could this be my comeback after all that time away from writing?

But the truth is also that I’ve spent maybe a max of 100 hours cumulatively meditating during and after my retreat. And I’ve only published 40 posts, so maybe I’ve spent a similar amount of time blogging. I just haven’t practiced enough yet.

I’m not perfect and I want you all to hear that from me, even though imperfection is obvious and is true of everyone. That’s what I’ve learned. It’s okay that I don’t have all the answers. It’s okay that I don’t get everything on the first try (…or the twentieth — I still can’t ride a bike). I over-intellectualize. I procrastinate. I struggle.

Right now, at least. None of those things define me, and they aren’t forever. Everything changes. So consider this my 41st try at writing. It’s okay – no, exciting even – that you’re going to have questions unanswered by this post. Or that you might not have read it.

It’s about time I start practicing in public.

(But it’s also okay if I don’t sometimes, just like it’s okay if this post doesn’t end on some epic thought-provoking sentence.)

This post is part 1 of a series about my learnings from vipassana. Part 2 on more background and FAQ is here.

Labor-positive innovation

It’s Labor Day 2013, and the people-work we celebrate today is under siege. In Marc Andreessen’s famous words, software is “eating the world,” and every redundant, repetitive job that previously required the skills of a person is a target.

Take for example the driverless car that’s been making news lately. In ten years, this technology alone promises to rescue billions of dollars in lost productivity from people sitting in traffic, replace every 1,000 cabbies with 250 new GUbers, and increase utilization of each car (converting ownership to temporary use) so we need fewer on the road.

Sounds great, until you realize that in one fell swoop, we’ve eliminated thousands of jobs in transportation, auto manufacturing, and even $121 bn in services jobs due to productivity gains from sitting in the car but not driving. That’s a lot of work displaced by just one technology, and the rate of these disruptions is only accelerating.

Responsible tech investing

I’m embarrassed to admit that, as an investor in startups and a member of the tech community, I’ve added fuel to this fire. I’ve rationalized the rapid job destruction by our industry as only temporary, wanting to believe that today’s disruptive technology will just create new kinds of jobs that we couldn’t have imagined before.

But the truth is, all this progress doesn’t benefit everyone equally. When investors back efficiency innovations that replace jobs, we make money at the expense of job holders. We then use that money to invest in even more technology, a vicious cycle akin to “standing on a beach holding our fire hoses full open, pouring more capital into an ocean of capital“.

In that way, tech investors have been acting no differently from the corporations that polluted the air and leveled the forests before us. I’m no Luddite but I know it’s not inevitable that software eats the world tomorrow. We’re just getting greedy and overfishing the lake.

So it’s time to prioritize labor sustainability.Tech entrepreneurs and investors are stewards of the capital that used to belong to workers, and we owe it to them to invest in technologies that create more jobs than taken away. I call these labor-positive innovations.

Here are the top three ways I’ve seen for us to invest responsibly.

1) Transition education

Millions of people who are getting displaced don’t have the luxury of learning their way into the services economy. The high cost of college or even online degrees, and the slow rate of skill acquisition in MOOCs makes those solutions intractable for people who need a job ASAP to support their families.

But thankfully, there are a few segments of the “middle-skilled” economy that are still growing. So new tech companies will be created that help people, through vocational education, to transition into the repetitive yet non-redundant skill work (eg in construction, hospitals, and new manufacturing) that humans are great at.

Often these middle-skilled jobs involve interacting with other people and complex coordination tasks, so we’ll need to modify traditional adaptive learning techniques to deal with this unique cross between online and real-world training. We’ll need new credentials such as tests and reputation systems to get these trainees into the workforce, and new cultural norms around vocational education. Germany provides a great example as Smil notes here.

2) Freelance and Entrepreneurship

Aside from educating people into today’s remaining growth sectors, we can also create new sectors that allow middle-class workers to make money on their own. In the physical goods and services worlds, this comes in the form of micro-entrepreneurship and freelance marketplaces such as Etsy, Kickstarter, Odesk, Elance, and 99designs.

These marketplaces are all labor-positive in and of themselves, helping people find work by aggregating supply and demand, providing access to capital, and reducing transaction, distribution, and coordination costs. There are hundreds of niche marketplaces still yet to be created, particularly those that are natively mobile (eg WorkMarket for hourly workers and Lyft for drivers).

But marketplaces that support micro-businesses and freelance are also enabled by a kind of labor-positive software. Tools for everything from payments processing to shipping to fraud detection to storefront building and optimization all serve to take the specialized knowledge out of building a small business. These often start as APIs for developers, and then evolve into full-service tools that make novice users look good without even trying (eg Shopify or Squarespace).

It’s critical that labor-positive marketplaces and software help individuals show off their uniqueness and creativity. This fosters clear differentiation of their goods and services on quality and perceptual value rather than destructive price competition. And facilitating one-to-one interactions engenders the kind of hyper-personalization that software can never replicate.

3) Entertainment and Leisure

Though education and micro-businesses can do a lot in the near term to stave off unemployment, in the long run the very notion of a job and the benefits it provides may have to change. What will it mean to live in a post-work world?

With technology and middle-skilled services taking over both full time jobs and mundane tasks at home, that frees up a whole lot of time for people to be bored out of their minds. So the entertainment, travel, and leisure industries will likely explode. Again, platforms and tools that make it easier for people to produce creative works will grow rapidly. We’re already seeing this happen with “long tail content” in TV / video, music, games and apps. Publishing tools and distribution platforms for the sale of digital goods will grow rapidly.

But digital goods have one extra benefit — the ability to create perceptual value out of thin air. Gaming worlds such as MMORPGs and casual games can have entire economies built around them, and “gold farming” in those worlds can be a full time job. I expect to see tons of innovation at the intersection of virtual goods markets, gaming, and entertainment of all forms — once again unleashing creativity and imagination to help people make money from what makes them human.

What else?

On Labor Day 2023, I hope we can say that we avoided massive unemployment, wealth inequality, and social unrest because our industry banded together for what’s right. When we cut down a tree, we need to plant five more.

Here are a few great thinkers on this issue for further reading. I don’t agree with all of them but think they provide a valuable diversity of perspective:
Albert Wenger’s series on Labor and Innovation
Vaclav Smil on The Manufacturing of Decline
Andrew McAfee on The Great Decoupling of the US Economy
David Autor on How Technology Wrecks the Middle Class
Clay Christensen on A Capitalist’s Dilemma
Tyler Cowan on Who will prosper in the new world and 10% Unemployment Forever
Sam Altman on Growth and Government
Paul Krugman’s various posts on Technology and Wages
Ashwin Parameswaran on Technological Unemployment Amidst Stagnation

If you’re a labor-positive builder, have read anything else I should check out, or think of any opportunities I’ve missed, I look forward to learning from you.

Do, not be

What do you want to be when you grow up? As you got older, your ideal answer might have changed from ‘fireman’ or ‘teacher’ to ‘partner’ or ‘CEO’. That change itself isn’t so troublesome – you’re growing up after all.

But what happens when you actually make it? Maybe you decided to be president in first grade, and forty years later you did it. Or replace president with your dream du jour. And change forty years to the shorter life cycle of your 21st century job. Where do you go from there?

I think we’ve always asked the wrong question. What you want to “be” phrases your goal in terms of achievements and titles. Maybe that’s a natural outgrowth of our networked life, where those factors are so visible. But in truth, “Imma be” is associating your identity with a destination. You’ll either feel disappointed if you don’t make it, or be unmotivated if you arrive.

Moreover, focusing on what you want to be promotes squandering the present. You’ll rationalize doing work that you feel indifferent about (or even despise) in the name of “putting in your time” and taking a step upward.

About a year ago, I found myself doing just that. Wasting the here-and-now on work I felt little passion for. In fact, my last post on “motivating yourself” was actually a more personal reflection on motivating myself — detailing the exact thought process that prompted me to change jobs. Through that exercise I chose new goals in terms of what could make me happy and motivated today.

This Thanksgiving I’m thankful to celebrate my first year at IA Ventures. Here, with this small family, I feel so lucky to have at once defined and done exactly what I love every day. I know now that I’m at my best when I’m around makers. I thrill at the chance to enable, in whatever small way I can, visionary leaders at the earliest stages of bringing their “favorite futures” to life.

Making what you love a part of your work starts with a simple step: refocus on what you want to do rather than what you want to be. The difference in framing will help clarify if you’re over-optimizing today for some title or wealth or fame destination you hope to reach.

Instead, follow people who inspire you. Work for a purpose you believe in. Build skills that you value because you like practicing them, not because others value them on your resume.

Chances are, what you want to do is actually the best way to become what you want to be. You just can’t see the path until after you’ve traveled it.

Motivating yourself

It’s Monday again. How are you feeling? Whether it’s your first job or your fifth, you may find you’ve lost the spark that once made your work feel great. Recently, I’ve been helping several friends think through their next moves.

I’ve been there before, having left my first job early-on. At the time I built a framework that helped me sort through exactly what I was feeling, and clarified the changes I needed to make. Hopefully you might find it equally useful.

(Much of this model is derived from Dan Pink’s book Drive, which explores the psychology of motivation. When I was changing jobs, I drew his three factors as the axes of a graph, and realized they mapped perfectly to three dimensions you can control for in selecting a new role. If you don’t have time to read the book, his ten-minute talk is a great summary.)

Are you working or being worked?

Let’s start by defining what it means to have a great job. It’s easiest to describe by its effects: a great job motivates you to keep pushing yourself. When you do your work, you anticipate a reward, and your body gives you the gift of increased dopamine transmission. The experience is frequently euphoric. A great job means you begrudgingly leave on Friday and can’t wait to get back on Monday (out of raw excitement and not being a ‘workaholic’).

But what kind of reward are you anticipating? It turns out, many bosses get this deeply wrong. In the employee-as-horse theory, one needs only a carrot and a stick. And the more substantial the carrrot, the harder the employee will work to get it.

Of course, treating employees like horses only works when their function is the intellectual equivalent of tilling a field. So pure compensation isn’t enough to motivate people who need to do creative, unstructured jobs. In fact, offering more money for intellectual work demonstrably has the opposite effect. Extrinsic motivation, like LDL cholesterol, is a necessary element in a harmful form.

Take a look at how you’re being compensated and you may get a clue about why your job satisfaction has dried up. Above a minimum level to pay your bills, mo’ money is not mo’ happy. Is there a carrot being dangled in your face? Does it come up in conversation? Do your managers encourage competition to get the biggest, juiciest carrot?

Then you might just be tilling their fields.

A 3-D approach to your job search

To find a great job for yourself, you need to focus on what maximizes your intrinsic motivation. With it, you’ll find yourself capable of all sorts of magic: working harder and longer, yet being happier even after taking a big pay cut.

In Dan Pink’s conception, if you want to be motivated, you just need to be AMPed. A great job is the right combination of autonomy, mastery, and purpose.

1. Autonomy is a measure of how much you craft your own role. When you’re self-directed, you choose what you work on, who you work with, and when and how you make it happen. You pursue tasks at the intersection of interesting and important. You take ownership over your work, are responsible for outcomes, and can see your impact directly.

It turns out, autonomy directly ties to the size and life stage of a company. As the organization grows larger and gets older, it defines roles, responsibilities, and reporting lines more strongly. People carve out territories for themselves. Equity and ownership over outcomes goes down, less excellent employees come along to ‘fill the role’ and politics form when people are more interested in job preservation than doing great work.

There are always trade-offs: a younger, earlier company has fewer experienced people to learn from, and less direction and feedback on whether you’re doing a good job. But on the whole, the more autonomy motivates you, the smaller a company you should seek out.

2. Mastery means to get better at something, which in a work context defines what you’re getting better at, and how much better you can become. Achieving mastery is motivating because it’s challenging, and as ‘gamification’ suggests, we like pushing ourselves to accomplish difficult feats for fun. But raw difficulty isn’t enough to keep pushing yourself. Like playing any game, you have to believe that the outcome is important, and be surrounded by others who you respect, learn from, and like being around.

This correlates strongly with job function, for example: engineering, product, design, operations, marketing, sales, business development, management, or anything in-between. What you do in the organization will define the tasks that you can draw from, how mentally stimulating and challenging they are, and the outcomes you’ll see. This one requires you to reflect deeply about your career direction, the type of person you want to be, and what you really love to do when money isn’t your motivator.

And perhaps more importantly, your function also determines what kind of people you spend your time with every day. How much do you share common values with your superiors? Since you inevitably become the average of the five people you’re around the most, choose wisely.

3. Purpose is the often-neglected reason for why you’re doing your work. It’s not enough to simply make money, or to enable other people to make more money. Just as the carrot wasn’t enough to motivate you, your company shouldn’t act like a horse either. It needs to have some greater, transcendent meaning in the world, producing good products and providing good service that makes people’s lives happier and better. You have to believe.

Your belief in a purpose is an extremely personal thing. You can’t get that belief from other people’s envy, or others’ definitions of what makes a company great. It has to come from within. So your deep, gut emotional reaction to a company is derived from how much you care about it’s vertical and love its products. Ask yourself if you’d be proud to tell everyone you meet that you work for this company, particularly people who don’t understand what it does.

Think about your past

Now that you know the three dimensions, try placing all your past jobs on the axes. How much did you choose your own work? What did you get better at, and how important was that to you? Why did your company, and by extension, your work matter to the world?

This exercise will be immensely clarifying, and you should repeat it often. Put it on your calendar twice a year.

Try lots of them on

You’ll likely think of the three dimensions and already have a strong opinion about one or two of them from your past experiences. Think of that as helping you take a slice out of the cube of possibilities. Every slice still has infinite variations possible along the third dimension.

Give yourself ample time to explore, and try lots of possible jobs on for size. Read a thousand job descriptions (I’m totally serious), disregarding how qualified you are for the positions. Keep reading until you have ten that you identify with and think you’d love. You’ll know them when you see them.

Then, look at the stage, function, and vertical of each job. I bet you’ll find they share more interesting things in common than the prospect of a carrot.

Note: below is an ad, inserted by, that is not part of this post.

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.


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.