Support Systems Make Long Odds Targets to Hit, Not Walls to Avoid

In another post this week, Hunter Walk wrote that the prospect (and indeed reality) of starting a company is hard. He referenced previous posts by Jason Calacanis and Paul Smith, both of whom wrote good posts on the kind of spine and drive you need to have in order to tough it out in this business. Both pieces were on point; Calacanis’ in particular struck a chord with me as it reminded me of how DIY punk you need to be in to work in the startup world.

Walk, however, brings something different to the table in his new post; he postulates how people from different backgrounds might have read the previous set of posts differently, and how they might have understood the points which Smith and Calacanis were making. Indeed, Walk strikes on this towards the end of his own piece, when he declares that something has been “gnawing” at him:

Starting a company—deciding to absorb that risk—should attract a self-selecting group of founders[,] but I also suspect stressing nothing but the long odds, the sacrifices, creates a barrier to entry for entrepreneurs who don’t have role models or a support system around them.

 

And in an instant, Walk seizes on something that is as palpable as it is subtle: those startup entrepreneurs who have a positive role model and/or support system from which to draw confidence are inherently better prepared for the slog than those who do not. However, it’s worth noting that many successful entrepreneurs didn’t come from families of entrepreneurs. Rather, they had to make the jump themselves—into instability, increasing pressure, constant rejection—in order to see their drive and vision fulfilled.   

I got lucky; the support system I needed was already in place. I wasn’t aware that my road towards the startup world started long before I ever thought to explore such a path. As such, the long odds are almost normal for me, and the DIY punk attitude is something which has always been underscored in my life.

For others, though, Walk makes an astute point: those who come from different backgrounds—the people who might be the first entrepreneurs in their families, or who have had to surmount obstacles that some of us might not have had to contend with (race, gender, economics, etc.)—need to be aware that they may be able to draw upon support systems outside their personal experiences and upbringing. Such an awareness can change their perception of the long odds although the odds themselves do not change. Walk:

How do we help potential entrepreneurs understand the long road ahead of them while letting them know there’s a support system to help them? Frankly…it’s better that 1% too many people start companies than 1% too few because you never know…And maybe that first time doesn’t work but the second time does…

Walk’s point is palpable; the view that success might be only one failure away is something that becomes ingrained in an entrepreneur who has a support system to fall back on. That support system makes one resolute in the face of the long odd; something to be confronted and overcome, circumstances permitting.

Successful entrepreneurs understand that the long odds are just numbers on a screen that tell you all the reasons something isn’t possible. With the right kind of role model(s) and support system, the long odds become less a wall to avoid than a target to aim at. Perception is a powerful thing, and is a key factor in the spine and drive which one needs to embody to forge ahead.    

Cold Emails Are an Opportunity, Not a Chore

Last week, Hunter Walk posted a short piece detailing a few calendar experiments he’d be trying this autumn. Amongst the challenges was a point which stuck out to me: his commitment to replying to any cold email at least once. This started a reflective thought process in my head on the heavy benefits of cold emailing.

I’ve Sent More Cold Emails Than I Could Ever Count

In my time and experiences within the music business, I’ve sent more cold emails than I could ever count; they’re virtually required if you want to start any sort of dialogue. In many industries (tech included), introductions through peers and contacts account for a large percentage of successful business relationships. Cold emails, however, work less often (excluding famous stories which have since become startup lore, like Box’s Aaron Levie cold emailing Mark Cuban and getting an investment). Many times, startup founders are lucky if they gain a response anywhere near Walk’s commitment to answer them at least once.

But in the music world, cold emailing is the norm; you better become very comfortable with it (and very good at it) if you want to get anywhere. You end up cold emailing artists, managers, promoters, bloggers/journalists, DJ’s, venues…the list goes on and on. You learn how to craft just the right sort of message that is equal parts fan and prospective business contact (and if you forget the fan part, you’ve majorly screwed up). Cold emailing becomes such a normal part of the overall flow that if you’re not sending at least a couple per day, you’re losing out.

The Benefits Far Outweigh the Drawbacks

Yet Walk’s piece reminded me of something different. We’re so used to reading posts about cold emailing written by the senders that many times the recipient’s perspective might go unnoticed. I’ve been on that end too.

I’ve had artists email me out of the blue asking for any number of things: a review of their new album, play on my radio show, feedback on their new single, advice about local venues, etc. And this is where Walk’s point hit home for me: it’s so easy to ignore cold emails (especially when there are mountains of them) that sometimes we can forget the opportunities which they can contain. Some of my best and longest lasting business relationships germinated from cold emails. It’s those solid, long-lasting relationships that have led to further opportunities in both the music and entrepreneurial spaces.

(It is of course relevant to note that cold emailing isn’t the only way to broach an initially unsolicited conversation. In my experience, there are any number of indirect methods that work just as well, if not better, than the cold emailing avenue. These, however, I think will provide fodder for a subsequent piece.)

Perhaps cold emailing in the music world is less overwhelming than it can be for tech angels or investors (which is both highly probable and understandable), but experience has taught me that Walk’s approach has benefits which far outweigh the drawbacks, so far as I can see. In opening his mind and palate up to what could be out there, Walk greatly increases his chances of striking upon a beneficial new contact and/or relationship. He does this because cold emails tend to go unnoticed or unanswered by some, and thus provide fertile ground for Walk to mine out new opportunities in an area all his own.

Where Some of the Greatest Opportunities Lie

Time-consuming though it may be, I think Walk’s proposed solution of setting aside 60-minute windows in which to go through these emails is precisely the right course forward. He is upfront about his limits (simply as a human with a life and a job) and does not set out to promise responses within a 24-hour period; everyone has a limited amount of time in the day and that’s just life.

Yet, when the opportunities are literally on your (digital) doorstep, I think the worst thing one can do is simply ignore them. In the music industry at least, one of the first things you learn is to look where no one else is looking. Taking the time to do so usually ends up being the best decision you can make; that’s where some of the greatest opportunities lie. I would be surprised if the same couldn’t be said for at least some level of the tech/investing space as well.  

An Artistic Analysis of Four Tech Investors

Seeing the World Through Artistic Eyes

Part of being an art student is that you inevitably see art everywhere, whether it’s meant to be noticed as art or not. This goes for anything—drawings, graffiti, cars, apps—and most recently for me, Twitter profile avatars.

Twitter avatar profile pictures of Fred Wilson (top left), Brad Feld (top right), Hunter Walk (bottom left), and Marc Andreessen (bottom right)

Twitter avatar profile pictures of Fred Wilson (top left), Brad Feld (top right), Hunter Walk (bottom left), and Marc Andreessen (bottom right)

As I was scrolling through my feed the other day, I saw a number of avatars go by, and my resulting thought process surprised even me—I thought wouldn’t it be cool to analyze those the way I used to analyze art pieces for my art history classes (well, cool is relative I suppose, but I’m an art nerd, so there). So that’s what today’s post is about: no talk of music, apps, or any major tech trends. Just an artistic analysis of the profile avatars of four tech investors. I wasn’t sure exactly how to order these, but I decided it would interesting to go according to an art history timeline, rather than simply by alphabetical order. Let the analyzing begin.

Fred Wilson

Fred Wilson‘s Twitter avatar is one of my favorites from an artistic perspective because of its striking power. I look at Wilson’s picture, which sets a large facial portrait against a lime-green background, and think immediately of the work of modern Austrian painter Egon Schiele (something which I’ve tweeted about numerous times). For those unfamiliar with Schiele’s work, he redefined the concept of portraiture in the early 20th century by daring to accentuate bodily features way outside their normal proportions. Some common aspects of Schiele’s work are overly-large eyes, and a strong, set jawline, usually defined by a sharp contour, which can clearly be seen in his pieces “Self Portrait” (1910) and “Self Portrait with Physalis” (1912).

Egon Schiele; left:

Egon Schiele; left: “Self Portrait” (1910); right: Self Portrait with Physalis” (1912)

Looking at Wilson’s picture, the enlarged eyes and clearly defined jawline fit the mold of Expressionism which Schiele helped to pioneer. The eyes are deep-set—almost sunken—but with a gleam that seems to burst from the canvas, made even brighter by the bold green that encapsulates the pupils. The cut jawline is mirrored at the top of the piece by raw, almost rugged strokes of brown making up Wilson’s hair. Yet while the zig-zag strokes chisel the top of the portrait in an almost sculpted way, the slight waviness of the hair on either side of Wilson’s heads help to capture a curved smoothness which bleeds out into the dynamism of the green background.

Fred Wilson Twitter avatar

Fred Wilson Twitter avatar

The life of the piece, though, is centered in the eyes, and the cheeks. The eyes swirl knowingly—disjointed only by the large space between them. The cheeks meanwhile, glow warmly with the only hot colors on the canvas: a roughly hewn pink which darkens towards the face’s edges. Even the the portions of the piece where the paint seems too thin are almost indicative of Schiele’s practice of leaving paintings unfinished. Collectively, Wilson’s avatar contains deep traces of Expressionism roots, though nodding to a lighter palette than was typically used in Europe at the time.

It’s also worth noting, however, that Schiele is not the only art master represented. Henri Matisse seems to make an appearance as well, mostly in the nose-area. While the nose seems almost too large for the face surrounding it, it nonetheless conjures up images of Matisse’s “Portrait of Madame Matisse (The green line)” (1905), or even his “Self-Portrait in a Striped T-shirt” (1906). Intentional or not, I nonetheless look at Wilson’s picture and see Schiele’s Expressionism and Matisse’s Fauvism and Modernism.

Henri Matisse; left:

Henri Matisse; left: “Portrait of Madame Matisse (The green line)” (1905); right: “Self-Portrait in a Striped T-shirt” (1906)

Brad Feld

Brad Feld‘s picture is similar to Wilson’s in that it’s a painted portrait. That, however, is where the artistic similarities end. Whereas Wilson’s piece drips of early 20th century Expressionism and Fauvism, Feld’s portrait exhibits a more mid-century style. The thinner mouth and quirky glasses add a Pop Art flavor to the portrait, a fact that’s exacerbated by the bright greens and purples that play through both the back and foreground.

Brad Feld Twitter avatar

Brad Feld Twitter avatar

While still set amid deeply defined contours, Feld’s jawline is nonetheless more curved and flowing than Wilson’s, and with the light stream of pink that follows the chin-line, Feld’s smile is captured perfectly. The curvature of the lower half of the portrait plays on the wavy strands of hair which sit at the top, floating in a controlled messiness which adds a sense of jubilance to the work.

The most striking feature, though, is Feld’s eyeline. Encased in straight-edged square glasses, the eyeline cleanly divides the portrait into two halves, thereby introducing a sense of order into an otherwise happy-go-lucky piece. The Andy Warhol-esque psychedelic color-scheme in the background is indicative of mid-’60s Pop, as is Feld’s mauve shirt collar. Seemingly taking direction from color-schemes like that in Warhol’s “Marilyn Monroe” (1962), Feld’s avatar bleeds with a real ’60s flavor.

Andy Warhol;

Andy Warhol; “Marilyn Monroe” (1962)

Of particular note, though, is Feld’s smile, which reminds me of pieces by a famous Pop artist, though not one the mainstream is too familiar with. James Rosenquist emerged separately from Warhol and Roy Lichtenstein, but is notable for his use of “the grin,” which can be clearly seen in the baby portion of “F-111” (1964-65) and in President Kennedy’s smile in “President Elect” (1960-61). The grin which plays through Rosenquist’s pieces finds a home in Feld’s piece as well, framing the portrait in visions of Pop from all styles of the decade.

James Rosenquist; top:

James Rosenquist; top: “President Elect” (1960-61); bottom: “F-111” (1964-65)

Hunter Walk

Hunter Walk‘s Twitter avatar isn’t hard to place; one look at it and the first thing any art student or aficionado would think is Roy Lichtenstein. The cartoonish quality of Walk’s picture is not only evident, but is the main focus of the piece itself. Whereas the previous pictures exhibited more subtle elements of the art movements which seem to be at play in them, here there is no question. The animated nature of the piece has a disarming effect on the viewer, making Walk’s smile seem all the more friendly.

Hunter Walk Twitter avatar

Hunter Walk Twitter avatar

Much like Lichtenstein’s “Drowning Girl” (1963), Hunter Walk is portrayed in a series of curves and flowing lines. Though obviously different subject matter than the aforementioned painting, there is nonetheless a similar ebb and flow that connects the two. Walk’s hairline is jagged only in certain spots, leaving the rest to create a circular movement around his head. The dynamism that this movement contributes to the piece cannot be understated because it is precisely mirrored by his shoulders and neck tilt.

Roy Lichtenstein;

Roy Lichtenstein; “Drowning Girl” (1963)

Rather than appearing stilted and set, Walk seems to lean into the movement, adding to its run through the picture. Even the shadowing of his beard and smile accentuate the flow of the centripetal movement. The darker shade of gray used for the beard moves along the face smoothly in some areas, and yet is cut sharply in others, much like the movement of waves splashing up against a cliff. The smile, meanwhile, is simple, but creates an eddie around which the flowing contours of the beard and facial lines must move.

Perhaps most interesting of all, though, is the way in which Walk’s beard in the piece seems to harken back to Lichtenstein’s common use of pointillism. While clearly one solid color throughout, Walk’s beard is nonetheless styled and colored in such as way as to appear to be more individualized than it really is. When compared to Lichtenstein’s oil piece “I Can see the Whole Room…and There’s Nobody in It!” (1963), Walk’s avatar seems to take on a different sense of shadow. As the man in Lichtenstein’s painting is lightly shadowed along his face to create a deeper perspective, so too does Walk’s beard in his avatar create for him.

Roy Lichtenstein;

Roy Lichtenstein; “I Can See the Whole Room…and There’s Nobody in It!” (1963)

Marc Andreessen

Perhaps the most post-modern piece of the four is Marc Andreessen‘s avatar, done in a way which most would describe as “South Park-ish” owing to its cut-and-paste style. While this is actually a good description based on South Park popularizing the cut-and-paste style in the last couple decades, it begs the question of what does that mean artistically? Is it just a cartoon? If so, why doesn’t it look like Hunter Walk’s Twitter avatar, which also exhibits a clear, cartoonish quality?

Andreessen’s avatar is a mix of post-modern, cut-and-paste qualities, but it also employs a sense of Pop which is prevalent in the other avatars. The sharp, clean lines cast the picture in brisk light, asserting that it’s so simple, there must not be anything under the surface. But there is.

Marc Andreessen Twitter avatar

Marc Andreessen Twitter avatar

The cartoonish Pop quality hides the other influences which dance through the piece. The basic oval-shaped hands, straight-line eyebrows and simple circular head harken back to the bare-bones approach towards geometry of Cubism, while the flat, cut-and-paste quality is indicative of the Superflat movement. As Cubists like Pablo Picasso and Juan Gris attempted to unravel the notions of geometry in art, so too did post-modern artists like Takashi Murakami desire to understand depth in a different way.

Right: Pablo Picasso;

Right: Pablo Picasso; “Girl Before a Mirror” (1932); left: Juan Gris; “Harlequin with Guitar” (1919)

The simple, circular curvature of Andreessen’s head in the avatar seem to mirror the circular head of the girl in Picasso’s “Girl Before a Mirror” (1932), while his egg-shaped eyes mirror those of the man in the Juan Gris painting, “Harlequin with Guitar” (1919). The flat quality of the avatar, however, jumps almost a hundred years forward, to the Superflat movement of the 2000s, pioneered by Murakami. As Murakami explored the flatness that depth could have in pieces like 2001’s “Tan Tan Bo,” so too does Andreessen’s avatar explore concepts of flatness and depth (perhaps without even knowing it). In its exploration of depth and geometry, Andreessen’s avatar is thus more artistic than it initially appears.

Takashi Murakami;

Takashi Murakami; “Tan Tan Bo” (2001)

Art and Tech Intertwined

Though these are just four analyses of four Twitter avatar’s it’s become clear that art and tech are more closely intertwined than perhaps initially thought. This might explain why I see pieces by Basquiat and other artists come up so often in the tech industry. But it may be even simpler than that—it may simply be that art resonates with people in the tech industry precisely because they are also in the business of creating as much as painters and sculptors are. Or maybe they just like how it looks, that’s a valid point too. In the end what matters is what you see when you look at pieces and avatars like this. For me, I see art that is deeper than what’s on the surface. What do you see?

Start Writing—Anything

In a short piece posted earlier this morning, Hunter Walk talked about writing, and how the need to be right is many times what stops people from putting their thoughts out there. Whereas some may seek to “write the definitive post” on a topic as Walk puts it, his advice, rather, is to pick something you’re fairly confident you know about and “riff a bit.” This is directly in line with my thinking when it comes to putting out something with my name on it; do the best I can writing the piece, make sure all basic spelling and grammar is correct, and then see what comes back my way in terms of commentary or questions.

I would, though, dare to take Walk’s advice one step further: if you want to start writing, don’t just write blog posts—write anything. Write news articles to learn how to instigate an investigative process, write essays to learn how to really flesh out an argument, write poetry to better understand the concepts of metaphors and literary devices, do interviews to learn how to speak to people and translate it into compelling writing. Not all of these things will pan out (and you may not enjoy all of them, or even any of them), but in sharpening your teeth on different writing styles, you lear how to mix and match to make your own pieces (blog posts, for example) more powerful.

As you descend into learning each new style in a hands-on way, the need to be right will fade some, and what you come away with is a more comprehensive understanding of presenting and/or winning an argument. The ironic side-effect of this (in my experience as a music journalist) is that people suddenly begin to think of you as a voice to take seriously. Go figure: stop trying to be the definitive voice, and somehow you get closer than you ever were when you were trying!

Of course, there’s an even more basic reason to write (and very much a reason I do): it helps the mind to work through new concepts and move the creative process along. Don’t worry too much about being right—just write.