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.

Trust in randomness

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

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

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

Have more fate

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

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

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

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

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

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

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

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

Follow the white rabbit

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

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

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

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

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

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

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

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

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

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

Eye in the sky

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

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

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

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

The I

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

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

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

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

Modern Joneses

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

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

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

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


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

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

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

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

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

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

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

Time to honesty

You get back, energized from the conversation over a great meal, only to find a glob of food stuck between your teeth. When you’re finished being mortified, the questions set in: did they notice? why didn’t anyone say something?

It might be tempting to question the character of the people involved, or the quality of those relationships. After all, a good person would discreetly call your attention to your teeth, so you could take action and avoid embarrassment. Instead, were they laughing inside the whole time? Or thinking of telling you but finding it too awkward?

Take a step back and invert those questions. Did you give people the impression that you’d be embarrassed? Or that you’d overreact to someone calling it out? Perhaps they didn’t feel it was their place to tell you.

Whether a morsel in your teeth, a crippling character flaw, or a terrible business decision, in every facet of your life peoples’ willingness to point out your mistakes is crucial to your success.

At what point does someone cross the arms-length boundary of formality and feel comfortable revealing the hard truth?

I call this your time to honesty, or TTH. How long this takes is partly a function of social norms, but mostly a function of how approachable, laid back, and open to feedback you seem.

It turns out, having a dangerously long TTH is common among executives and middle managers. As you rise in formal rank, be it in your business or your social circle, you begin to seem “other” and distant. People become wary of offending you or overstepping the bounds of their ranks, particularly to comment on your limitations or mistakes.

This has an isolating “death spiral” effect — the more important you become, the more you become reliant on your longstanding friends to be real with you. And as you rely on these confidants more, you perceive new acquaintances to have their guards up, and they perceive the same from you.

It’s hard to imagine that you’re complicit in your own blindness to faults; after all, it’s being imposed by others restraining their feedback. You might indulge in rationalizing your own behavior and shifting blame.

But ultimately, the fault is your own. As you get older, more important, and more set in your ways, you need to proactively counter this effect every day by leaning in and making yourself easier to approach with bad news.

The lean-in is a subtle habit worth practicing in every conversation. Sometimes it’s making a joke about yourself to demonstrate that you don’t take yourself too seriously. Or showing a chink in your armor, allowing others to see you as sometimes weaker than you’d like them to know; for example by acknowledging a difficulty, lack of skill, or missing knowledge. Anything to show that as your own world’s emperor, you don’t mind being told the new clothes are missing altogether.

Counterintuitive, perhaps. It’s the exact opposite of the impression management we’ve learned to maintain for every public action. But others will only admit your imperfections when they can see that you already know yourself to be imperfect.

Pride may cometh before the fall, but that’s a spurious relationship. It’s really perceived pride that leads to fault-blindness. The only way to limit that perception is to systematically test it and break it down through actions.

So the next time you feel a seed stuck in your teeth, don’t be so quick to pick it out. Count your TTH, and check your posture. You might need to lean in a bit.

Conversational risk

It was freezing out today. Which was pretty unusual, because it’s been really hot out lately in the middle of December. We thought it might be global warming before but now it’s so cold. But at least it’s not raining.

Sound mundane? I hope so. But it’s very real. So many conversations walk a well-trodden path: the exchange of biographic details, the search for points of commonality, exhaustion of those points, the discussion of mutual acquaintances, further exhaustion, and the soft fizzle-out on an inane topic like the weather.

Now, think fast – pick a first meeting that left a lasting impression.  What was different?

You dug deeper. You jumped around and landed on a topic that you both actually care about. You weren’t too politically correct, and didn’t act like everything you said was being recorded. By the time you walked away, you felt like you learned something new, ended up closer to each other, and laid the foundation for a continuing friendship.

Backtrack. What led you into that memorable conversation?

One of you let your guard down, made yourself vulnerable. Asked a question that might have been offensive or gotten you laughed at. Offered up a personal detail that was a little ‘unsafe’. Someone took a conversational risk.

I bet every one of your closest friendships has started with just that kind of uncertain moment. One of you volunteered to take the dive. And then magic happened.

You found the joke funny, or connected with a shared childhood experience. Or maybe you had the same opinions on those highly personal no-no topics. Politics, sex, drugs, religion, the military, your boss, relationships, education, race. It was polarizing and you ended up on the same pole, or you had a heated debate but liked each others’ style.

I’ve found some of the best conversations evolve around important decision points in our lives. Pick a tough one: leaving a job, ending a relationship, choosing a school, starting a company. Always ask ‘why.’  When you dig into how someone makes decisions, and the lessons they carry from past mistakes, you learn what really makes them tick.

But don’t get me wrong, it’s always a jump. Like hopping on the top of a seesaw and hoping this person you don’t know will get on too before you hit the ground. I’ve hit the ground a lot, but I keep jumping.

Why? I think real new friends are worth the risks. You put your social capital on the line, and nine times out of ten, you’ll fail miserably. You have to get comfortable knowing that most aren’t going to like you or agree with you. You remind yourself that the nine don’t last, but the one does. I’d take that bet any day.

So next time you find yourself with someone new, remember that you’re starting at a point on a terrain like this, but you can’t see the peaks and valleys.  All you can do is jump. The possibility of an abyss is worth it, because the upside is a summit that you’ll both carry with you forever.

If we just met, don’t be off-put by my pointed questions and deviations from comfortable topics. I’m betting we’ll find a mountain worth climbing.