Oct 19, 2021


"Is a dream a lie if it don't come true?"

Back in college, a few friends were studying in the UK. One night they walked into a pub, saw a bar-band playing and fell in love. They made excited calls back to us in the States; they mailed cassettes of the band playing, the handwritten setlists filled with exclamation marks.

A plan was hatched.

We knew nothing about anything but were avid readers of music books and biographies, of Rolling Stone articles.

We decided we would fly the band over for a week, put them up in dorms throughout the school, introduce them to everyone, and end the week with a big house party on a Saturday night where the band would perform. Fame and fortune would result. The band readily accepted, we offered to pay them in free room and board and contraband.

A few months later the plan became reality and the band was in the US. The week was spectacular, they cruised around campus as wannabe celebrities. As newly-minted managers and promoters, we realized we needed a PA system. We took up a collection and bought one along with high-quality speakers. We hired a crew with a stage and lights to set up and break down. Saturday night - the night of the concert - expectations and nerves were high. The house was packed. We DJ'ed the first few hours before the band took the stage around 9 pm.

They launched into their first song, the sound was great, the crowd was surging.

Halfway through that song someone pulled the fire alarm in the building. Lights went on, alarms blared loud. Firefighters and police showed up. The party was over, the show was over, the evening ended.

And just like that, our illusions  - delusions - were finished (and when the hangovers ended sometime the next day, we discovered someone had stolen the PA system and speakers).

*  *  *

In high school, we knew this kid - D - who dreamed of competing in the Golden Gloves boxing tournament. He trained all year for his opening match. We bought him a robe with his name stitched on the back. We traveled to Queens for D's first match in his march for the title. For that march, he drew an opponent - I still recall his name: Julio "El Gato" Cruz. We sat in the front row screaming our heads off. The bell rang, D and El Gato met in center ring, tapped gloves and the fight began. El Gato swung once, hitting D on the chin with an uppercut. It was as if D's body floated upwards in slow motion, feet first head second, to where his body was perpendicular with the ring for a split second. His body then came slamming down. He was out. Match over. El Gato maybe went on to win the tournament.

*  *  *

When the fire alarm went off and the party ended, the band was playing the REM song Driver 8. When that Golden Gloves fight ended, we drove back in this kids parents’ car - a decommissioned yellow checker cab repainted grey, fold up back seats intact

*  *  *

I wrote a business plan back in 1998 for a direct-to-consumer digital book service. Pre-Kindle, pre-iPad. I recently found the plan - “digital delivery of previously unavailable titles, author compensated directly.”


Those words read today like anachronisms.

*  *  *

Is there a way to evaluate the almost-dreams that became forgotten-memories? Or is there value in them simply having occurred? Maybe they aren't lies. Instead, the "adjacent possible" reminds us that there is a "shadow future, hovering on the edges of the present, a map or guide to all the ways in which the present can reinvent itself."

In other words, maybe the expense of emotional courage in and of itself is enough.

Mar 7, 2021

On art and business and context and mirrors


Jean-Michel Basquiat - Untitled, 1981

Estimated value $300,000-400,000

1/ It used to be that value could be determined by scarcity. The less of something, the harder it was to get, the more it was worth for you to get it. Maybe even the value of a piece of something (art? content?)  was more related to the scarcity of its distribution than it was to any measure of value. In equation form, we could think of this traditionally as: Value (V) = Scarcity (S) * Quality (Q). Q of course, being largely subjective, is impossible to measure. But S is not. Maybe S then acted as a multiplier of value.

Yet, one of the superpowers of connected technologies - networks - is that they will remove scarcity if at all possible. Connected networks by definition make things abundant that were once scarce. They broaden access. Without judgment. Removing scarcity is a way to create new types of value.

2/ What is art? One can think of art as anything - images, music, video, gifs, text, memes. Anything really.

Art also is a mirror. That is, it reflects the world back to us so we can see it more clearly. In that way, art is not simply important, it is indispensable. The Velvet Underground’s first record - The Velvet Underground and Nico - lists the artist Andy Warhol as a producer. That record’s cover art is a Warhol print of a banana. The album contains the song I’ll Be Your Mirror:

I'll be your mirror

Reflect what you are, in case you don't know

This suggests a potential first principle: that more art available to more people more often can only be a good thing.

3/ Maybe digital art and non-fungible tokens (NFTs) are relevant here. A digital file, when intersected with the ubiquity and scale of the internet, can be “seen” by anyone. NFTs push the notion even further. By adding to the ideas of abundance and scale those of passionate distribution, patronage, the day-one fan and, yes, ownership. Concepts associated with scarcity, now distributed out to the abundant world at large.

Yes, there is no limit on the supply. Yet, connected networks make things that were scarce now abundant. 

4/ NFTs and cryptoeconomics (tokens) in general force the ownership issue by allowing for everything to be, and governed by, a market. This is neither good nor bad - it is, though, very different. Worth considering more.

At the same time, I wish Warhol was around to see this. In many ways, he conceived of and predicted it more than 50 years ago. He was explicit that art meant business and business meant art. In an inversion (or provocation) about the notion of artistic creation, he called his studio The Factory. He also said: “You know it’s art when the check clears.” And:

Being good in business is the most fascinating kind of art.

Making money is art and working is art and good business is the best art

Another artist (Jay-Z) reflected this concept back to us in his 2005 lyric:

I’m not a businessman; I’m a business, man

Artists taking agency over their own economics is not new. Maybe what is new is - again - the scale and abundance, that more people can experiment with this notion of artistic agency. 

5/ I love Warhol’s Campbell’s soup cans. I could look at them all day. Not for the brush strokes - these are silkscreen printed - but for the representation of the world they reflect. A Warhol soup can looks exactly like the actual cans. Thus, they mean something different about art by trying to tell us about commerce and ourselves. Warhol himself decried almost any notion of creativity and agency in his works, via technique:

I find it easier to use a screen. This way, I don’t have to work on my objects at all. One of my assistants or anyone else, for that matter, can reproduce the design as well as I could.

Here is a piece of art and associated NFT -  “a PNG file containing 0 bytes of information - the world's smallest NFT” - by the artist shl0ms:

This reminds me of John Cage’s piece 4′33″ - a score that “instructs performers not to play their instruments during the entire duration of the piece.”

Mamet once wrote “a great meal fades in reflection. Everything else gains.” What he meant, I think, was that it’s not the thing that matters, but the thing about the thing. The context of the thing. How you experience the thing. NFTs enhance this by providing for a supercharged way to understand the text and the context (and the money context) all at the same time.  

John Palmer wrote an essay minted as an NFT. He called it the “first community-owned essay, crowdfunded on Ethereum.” The writing - Scissor Labels - is wonderful: thoughtful, quirky, idiosyncratic and long; it covers design and music and cultural theory and software and hyperpop. It is a mirror.

6/ I wrote about this 5 years ago in discussing a company called Mediachain, which asked us some questions. How do you show what is behind a digital thing, understand it, pay for it? This still feels new today: 

We might be able to find out the identity of the photographer, send her a micropayment, see what social network it originated on, see the press the image received, find more images by her and any number of other things.

Back then, there really weren’t tokens or NFTs. So now, when you have a digital thing, powered by an NFT, more new questions arise: shall I own it, display it, port it, trade it or sell it?

Questions that perhaps force us, again, to look into the mirror.

Jan 18, 2021

You'll Figure It Out

 I'm sure we're taller in another dimension
You say we're smaller and not worth the mention
- Frank Ocean

When I worked at AOL, we typically worked from 8am until 9 or 10pm. At the end of every day, we'd congregate in the office of our boss, to sit around and bullshit and catch up on email and talk about deals we were working on and issues in those we were facing.

One evening we were doing this, and the conversation turned to the renewal of a content distribution deal with The New York Times, one of AOL's largest and most important partners. The difficult issue here, as with most of these, was whether AOL could demand exclusivity in exchange for distribution. For example, we knew AOL members loved the Times' crossword puzzles. We wanted them for ourselves, or at least before they went up on the Times' website. The Times wanted to limit exclusivity, or at least get paid. We believed our distribution was so massive that it alone was a fair exchange for some exclusivity. Thus, the deadlock.

I remember this conversation, sitting around the conference-like table in that corner office, 4th floor of a 5-floor building. Winter was outside and the view from the windows of the Dulles, Virginia office reflected the black and cold early evening.

Bob Pittman, the President of AOL, walked around the corner and stood in the doorway. This was relatively early in his tenure at AOL, yet he was known to us already as a media and business legend. 

"What's going on?" he asked, smiling. Our boss replied by explaining in detail the exclusivity issue, the various choices and options we had, questions about where we might push and where we might give.

Bob listened. He paused for a moment and replied:

"You'll figure it out. Have a good evening."

He lightly tapped the office door with his open hand twice, as if he was slapping it five. And then walked off.

There was a moment of silence before we got right back into it. We figured it out - or at least we tried. Ultimately, we didn't appreciate the move to the more "open" web would have on the proprietary AOL platform; nor would the Times appreciate the traffic AOL brought and our ability to allow them to experiment on a new generation of Internet users. We met somewhere in the middle, maybe even paid them, and it turned into a relatively good relationship over the years.

The thing is, maybe we got it right. Or maybe we didn't. I assume Bob knew that. I'd also like to believe he didn't really care. Or rather, he cared about the outcome but equally cared about making sure his team - us junior members - thought for ourselves. To empower us. To demonstrate his trust in us by specifically letting us make the decision. And figure it out.

A formative idea for a younger me: give the people who work for you a chance to resolve complex issues on their own.

Mark Randolph, the co-founder and initial CEO of Netflix, writes about this in his book, That Will Never Work. He describes what he came to understand about managing people: 


What they really want is freedom and responsibility. They want to be loosely coupled but tightly aligned.

There is no way Bob, or anyone else in that room, remembers that evening. Yet I do, in detail, years later.

And still find myself saying to people "you'll figure it out." 

Dec 6, 2020

Get No (perceptions of user experience)

I attended a "progressive" (read: hippie) school on the Upper West Side called Walden. In 2nd or 3rd grade, our teacher Gloria pulled out a record player every morning and let us dance around, I'm sure as a way to help burn off the energy of a large group of seven-year-olds. 

She played the same song for us, every day, at the same time. The song's chorus was "Get No" and we would shout and dance around, screaming "Get No!" I remember the dance, the singing, the names of the kids, and the way it set up the rest of the day. 

This class picture might have been from that year:

When Google launched, I noticed two things. One was that PageRank (the algorithm used to rank web pages in search results) seemed to work *really* well. The other, more vivid, was the interface:
The simplicity of this for sure, but something maybe more profound. The way this interface was neither a directory (like Yahoo! at the time) nor channels (like AOL) - it was just free form search. Pure search. Insert whatever words you like, we'll help you find it. The idea seemed to be that control would come totally from the user. 

The implicit suggestion was: "You don't need to remember where something is, you only need to know how to find it."

The technology mattered here; yet, the interface shift may have been what changed behavior forever.

This reminded me of a meeting I had last year with someone who was interviewing for a product role at The New York Times. His recommendation for the Times was to mimic The Daily (the podcast with episodes based on the reporting of that day) and turn the whole "paper" into audio products. This got me thinking about the interface, or user experience, of The Daily: consistent length, format, and host. From the Times itself:

"Twenty minutes a day, five days a week, hosted by Michael Barbaro and powered by New York Times journalism"

Prior to The Daily, news podcasts existed. Yet, The Daily has consistently been one of the most listened to podcasts, maybe one of the most listened to of all time. Here's a chart of the New York Time stock price from January 2017 (when The Daily launched) to the present:

Again, the content in The Daily matters (of course); perhaps though the results from the interface shift are more profound.

A related topic is email newsletters. Regular information sharing via email is not new. What is happening now that is driving more attention and usage? A shift relating to user experience. Looking at Substack, here are three inbox examples from this morning:

Notice the consistency among font, spacing, layout, heading. This consistency appears new applied to the existing medium (email). Moreso, perhaps the user experience from Substack  - the common look and feel - results in implicit cognition among users, something akin to "this is information that will help you learn something new." The innovation then, if you will, comes from the altered user experience. 

All this is to suggest only one thing: that new ways to experience something, especially something that already exists, can be the most transformational. The interface can be the message when something old is presented in a new way.

It took me a few years to realize there was no song called "Get No" we were dancing to in Gloria's classroom. Instead, it was a song about angst and shallow obsession with consumerism repurposed for seven-year-olds' movement play. 

It was (I Can't Get No) Satisfaction:

Oct 27, 2019

Everything about venture capital . . . you can learn from music lyrics

Here I go, it's my shot, feet fail me not
This might be the only opportunity I got

As I get older, I find that I need to give myself mental tricks to remember ideas or concepts.  

A few weeks ago I gave a brief presentation at a USV offsite that uses music lyrics to cover some of the concepts about venture capital that I think about often. My first draft was much longer - 70 or 80 slides. The final one is 36 slides. I have attached it below.

The playlist is:

Drake & Future - Change Locations
Bob Dylan - Don’t Fall Apart on Me Tonight
Jay-Z - U Don't Know
Bruce Springsteen - Rosalita
Lou Reed - Some Kinda Love
Courtney Barnett - Avant Gardener
Post Malone - Leave
Ween - Roses Are Free
Lil' Wayne - 6 Foot 7 Foot
Jay-Z - D'Evils
Rihanna - Pour It Up
Kanye West - Touch The Sky
Billie Eilish - Bad Guy
Willie Nelson - Blue Eyes Cryin’ In The Rain
Lizzo - Juice
Taylor Swift - You Belong with Me
The Beatles - The End

May 5, 2019

What Do You Think?

The whole freaking world was full of people who were bound to tell you they weren't qualified to do this or that but they were determined to go ahead and do just that thing anyway 
-Tom Wolfe, The Electric Kool-Aid Acid Test

In the mid-90s I worked for a man whose management style we used to call Mentor/Tormentor. He would give us - junior, barely experienced businesspeople - complicated yet wildly interesting transactions to complete (from start to finish) with almost no guidance other than “you’ll figure it out” or “you know my issues.”

Definitely the most stressful professional moments I’ve ever had. Also definitely, the most I ever learned in a work setting. His philosophy appeared to be that he hired smart people and relied on them to figure things out.

Managing a group of people is hard, especially as that group of people gets larger. At betaworks, I remember the feeling when the company got large enough that when the office door opened and I looked up, I could no longer tell if the person walking in worked with us or not. That feeling was one of intense uncertainty.

At the same time, the “contract” between a company and an employee can be thought of very simply. Patty McCord uses this succinct construct in her book Powerful: Building a Culture of Freedom and Responsibility: “Help make our company more valuable, and we’ll make you more valuable.” 

The most effective way I’ve seen to make employees more valuable at the same time as creating a space for them to do their best work was the one I experienced: by giving people agency over their ideas, decisions, and suggestions. That agency came with fear and repercussions - the fear of screwing up, of making the same mistake repeatedly, of not getting the next great assignment - but it was personal agency nonetheless. 

And the most effective technique I’ve used or seen to deliver agency is also a simple one. Ask someone: “What do you think?” “What do you suggest?” “What is your opinion?” Ask it over and over again and listen to what people have to say. Then let them try it out.

We still tell stories about the Mentor/Tormentor, about deals that we screwed up and victories that we won. There were a ton more of the latter than the former. He made us more valuable professionals, and in turn we made the company much more valuable, by letting us experience the feeling of acting independently and making choices. By giving us agency. By asking us “What do you think?”

Jan 20, 2019

Ghosts and Ancestors

People will tell you where they've gone
They'll tell you where to go
But till you get there yourself 
You never really know
-Joni Mitchell

Towards the end of his Broadway show, Bruce Springsteen describes how he’s realized that as parents, we have a choice to make: will we be ghosts or ancestors to our children. As ghosts, we haunt them with our mistakes and burdens; as ancestors, we free them from our flaws and walk alongside (or behind them) and help them find their own way.

In the past few months and without really thinking about it, I’ve started to get my morning coffee set up in place before I go to bed. On the kitchen counter I place the coffee dripper, filter, and scale, and then I weigh the beans. Last night at dinner I realized this was what my mother used to do every evening when we were kids. 

Was she now being a ghost to me, or an ancestor with me? Maybe it’s not so easy to tell.

She never said to do it this way, I just watched her. Mornings were busy - she alone had to get two boys off to school. This made it a little easier. 

In Martin Gurri’s The Revolt of the Public, he makes the provocative point that we are in a period of crisis resulting from the switchover from an “industrial” world to an “information” world. In that industrial world, trusted institutions mediated the flow of information to people and thus created coherent visions of society. In the information era, people have direct access to information themselves and thus have seen that these institutions are fallible (maybe even corrupt). The result - a crisis of authority. 

I’ve spent a large portion of my career investing in early-stage companies. Part of that job is to advise and counsel, to assist a company in reaching its potential. I try to ask for feedback on how I am doing in that job. A constant thing I hear is to provide more direct answers to problems posed to me. Typically, I am told, I answer their questions with further questions.  

Yet, I think it’s important to tolerate ambiguity. Maybe there isn’t a direct answer. Maybe I don’t know the answer. Maybe I want to assist others in coming up with their own answers. A partner of mine used to say its ok to make a mistake, but not ok to make the same mistake more than once. Where is the balance? Here, of course, the relationship is not remotely the same as parent/child, but I still don’t want to be a ghost, rather an ancestor.

In the end, Springsteen describes what happens when you walk alongside and assist someone in finding their own way: transcendence.

May 20, 2018


What is the future that will unfold?
Some like it hot, others like it cold
But we all want to hold the remote control
-Beastie Boys

Sometimes a service provides a value to its customers that may not be readily apparent at first glance. And sometimes that value can be more fundamentally important to those customers that the actual “widget” that is being sold.

Netflix is a good example. Their stated service is simple: “Watch Netflix movies & TV shows online.” But if you listen to the words of the people that run that company, something different emerges.

CEO Reed Hastings has in the past described how viewing works on Netflix:

“Binge-watching is great because it puts you in control. You have complete flexibility.”   

These words don’t appear to be an accident. Chief Content Officer Ted Sarandos was very specific in February 2018 when he stated that "the core to the consumer proposition of Netflix is consumer control."

Clearly, Netflix provides a service to view content. But it also delivers something much more powerful to people - the ability to determine how and when to spend their time, attention and focus (a form of self-actualization). To compete effectively with Netflix would require that another service competes on the axis of control. Not as easy as delivering content.

Having and giving control is very empowering.

This gets interesting if we view control as a way to evaluate markets or companies. What other services deliver control to their users in this way?

Let’s take healthcare. How transformative would it be to see services that deliver a radical shift in control from the system to the patient? What would this mean? More than online appointment booking or pleasant offices. Instead, directly shifting control over time and space from the provider to the patient.

The value of control, or agency over a person’s own time and space, is hard to measure or quantify in a business model. The Netflix analogy here is instructive. Some have imagined what the Apple or Amazon of healthcare would look like. The Netflix of healthcare would be vastly more interesting. It could catalyze a movement in a market where changes are tightly-restrained by large organizations and professionals. It would provide a value to consumers beyond just their health: control.

Feb 11, 2018

Addition by Subtraction

“Dangerfield eliminated everything from his act
but the setups and punchlines”

Alex Halberstadt’s essay on Rodney Dangerfield is a masterclass on how to improve by reduction. Dangerfield worked for decades as a comedian until he figured out the thing, his insight: “by eliminating every extraneous element, you could isolate what makes it work and just do that.”

Dangerfield reduced his act to just two lines: setup and punchline.

There are other examples. Blumhouse Productions (Paranormal Activity, Insidious, The Purge, Get Out) uses only micro-budgets of $3-5 million per film. This limit doesn’t come solely from frugality. Rather, from the idea that

“Anytime you limit somebody, it always - in terms of resources - kind of creates opportunities. Our movies have few visual effects”

Blumhouse films have grossed over $2 billion worldwide.

Steve Martin writes about this in his memoir Born Standing Up. He describes more than a decade of performing with only marginal success before it occurred to him to reduce his act:

“What if there were no punch lines? What if there were no indicators? What if I created tension and never released it? What if I headed for a climax, but all I delivered was an anticlimax? What would the audience do with all that tension? Theoretically, it would have to come out sometime. But if I kept denying them the formality of a punch line, the audience would eventually pick their own place to laugh, essentially out of desperation”

In this case, Martin’s constraint was to deny the audience the very thing they expected to be at the core of a comedy routine.

Constraints can apply to fields beyond entertainment. I’ve written before about how USV applies a series of constraints to guide our investing framework. Those include a specific investment thesis, small fund size, single office and collaborative decision-making.

Willie Nelson once remarked that “three chords and the truth — that’s what a country song is.” This legendary graphic from the Sideburns zine gets even more specific:

In working with entrepreneurs I often first ask them to consider what to remove from their service or application. Maybe this also applies more generally. We could then regularly embrace what happens simply by applying constraints to what we do.

Nov 12, 2017


If dreams came true, oh wouldn’t that be nice

Most of my sleep dreams are mundane if I can even remember them. The other night I dreamt that I missed a flight to Toronto because I didn’t have my passport.

There are other dreams that are more profound. Those are the dreams of one's life - how it turned out, how you wanted it to turn out. We often evaluate our life based on its relation to those earlier dreams we created. Sometimes that hurts.

But maybe instead of being ends, those dreams are means. Guideposts, data points, simple memories.

Bruce Springsteen’s new show Springsteen On Broadway makes this point. It comes on the heels of his 2016 autobiography, Born to Run. That book - as I read it - was not specifically about dreams. Instead, it begins:

“I come from a boardwalk town where almost everything is tinged with a bit of fraud. So am I.”

Here we have the artist messing with our mentals - trying to flip every preconceived notion of who we thought he was. Springsteen, though, is too clever for something as simple as that. His autobiography too is a work of art.

Thus, On Broadway backs off from - indeed, alters - his earlier self-classification as a fraud. Instead, in the show, he calls himself a “magician.” What is that magic? A songwriter whose famous songs are about busting out of your hometown, yet now lives 5 miles from where he grew up. A body of work about the hardships of the working life, yet who has never had a real job. No longer is this person a fraud, for his art is magic. An art form in and of itself. One can still be authentic and be a magician.

This matters because he can now be comfortable with those earlier dreams, those represented in the songs. For he is now free of having to actually live them. They don’t represent the ends of his life, just the means. They are just ideas. We don’t need their literal success to find true meaning in life.

One good minute could last me a whole year

On Broadway reminded me of one of my other favorite works of art, Bob Dylan’s book Chronicles: Volume One. The main feeling I took away from that book was the mundanity of Dylan's life. Chronicles can then be read as his personal confession: at one point in time, I wrote some really, really good songs. I am not sure why. Other times I wrote merely good songs. But I am also a father, and I took my kid to little league games, and those were profound moments for me, maybe as much so as any “protest” songs (but I can’t explain how those happened anyway). It is as if Dylan is saying: my little details matter to me as much as my songs might mean to you. You don’t know me because what you'd find is far less interesting than what you'd expect. But, it's interesting to me.

In a new podcast with Malcolm Gladwell and Rick Rubin, Eminem relates his insecurity as a songwriter. He speaks about being younger when his art was a blank canvas. Everything he did was a new component filling up that canvas. But, as he matured, it became harder and harder to find blank spaces. The canvas is full. Insecurity, even ego death, occurs. What does one do? Springsteen refers to something similar in his Broadway show. He tells a story about how he can remember when he felt the most joy in his life: he was 19 and broke, his family had moved to California, his sister had moved out. His only friends were his bandmates. And yet, he was intensely happy. Everything was fresh and ready to be painted.

The trick was to surrender to the flow

My favorite time in NYC is 5am. That semi-quiet moment, motion is occurring but at three-quarters speed, the streets and cars providing most but not all of the light. Volume is there - it always is - but it is hushed. Stores opening. People just getting home. At 5am, all that exists are the details. There is something about this middle ground.

I backpacked around Asia a long time ago with a friend. Over the years the memories became more specific. We remembered less and less about the temples outside Jakarta or the canals of Bangkok. Instead, it was the guy from Canada who was obsessed with Arthurian legend. The bar in Koh Samui that showed VHS episodes of The Young Ones 24 hours a day. Mamet reminds us in Glengarry Glen Ross that ”a great meal fades in reflection; everything else gains.”

So many things I would have done but clouds got in my way

Maybe then it is important to dream and live our life with those dreams. Perhaps, though, we’ve used them the wrong way. They aren’t supposed to come true but are only meant to guide us to a place, a place of different truths. After all, as Robert Louis Stevenson wrote, to travel hopefully is a better thing than to arrive.