Balter's Writing Portfolio — StoryShelf
Balter

Balter

aka Balterer
78 pieces published 7 platforms

Writer of mostly acerbic witticisms

buttondown.comMediumBalterer - MediumStories by Dave Balter on MediumInc.comBalterer
AI-Ready Shelf
Body of Work Intelligence
An editorial reading of the complete catalog — Edition 2

Balter's body of work is governed by a central tension he never quite resolves, and which supplies most of the energy on the page: the compulsive builder who cannot stop moving forward set against the grieving son, the divorced father, the man who hasn't cried in fourteen years and writes about it with something approaching bewilderment. The early Inc. columns are competent startup-leadership fare — mentor well, stay humble, befriend your rivals — but even there the confessional impulse bleeds through, as when he admits his ego nearly destroyed BzzAgent before its sale. What happens over the subsequent decade is a slow, jagged migration from prescriptive business writing toward personal essay, culminating in the Balterer newsletter pieces of 2025 and 2026, where the voice finally coheres into something distinctly his: digressive, self-interrupting, profane, tonally restless, toggling between standup-comic timing and genuine anguish. The serialized "Storyer of Smarterer" is the fullest expression of this mode — startup memoir rendered as picaresque, where accidentally smoking PCP and negotiating an acquisition coexist in the same register, because for Balter the chaos is the register. His father's decline and death across "Let Go, Dad," "Hospice," and "So Long, Dad" constitute the emotional spine of the entire catalog, the place where the wisecracking deflections finally buckle under weight they cannot carry off.

What recurs across the work is not a subject but a posture: the narrator who tells you the rules of engagement before breaking every one, who insists on irreverence as a structural principle while circling themes — mortality, loyalty, the transactional nature of trust, the strangeness of money — that demand earnestness. The Grateful Dead and Eggy pieces, the weed writing, the Twelve Tribes cult digression, the tape-dub entrepreneurship origin story — these are not lifestyle content but attempts to locate a self that was formed in subcultural devotion and serial company-building and can't fully account for either. The self-authored fake book review of "Invisible" is the most revealing gesture in the catalog: a writer constructing his own critic, preemptively ventriloquizing the charge that recognition has been mistaken for revelation. Balter writes like a man running a machine he has named but cannot turn off, and the best pieces succeed precisely where control lapses — where the grief for his father outpaces the joke, where the marriage to his co-worker complicates the founder narrative, where the airplane bathroom rant curdles into something genuinely misanthropic. The contradictions are the work: sentimentality armored in swagger, vulnerability delivered as bit, a founder's confidence undercut by a recurring suspicion that building things may be compulsion rather than calling.

Editorial History · 7 previous editions
4
Edition 4 March 7, 2026 · 41 pieces

Balterer's catalog reads like a man arguing with himself in public and daring you to look away. Across forty-one pieces, the dominant register is confessional bravado — a voice that insists on its own candor while stage-managing every revelation. The writer circles obsessively around a handful of gravitational centers: fatherhood and filial duty, the mythology of entrepreneurship, the Grateful Dead and its cultural penumbra, and the body's stubborn refusal to cooperate with the mind's preferred self-image. What links these seemingly disparate concerns is a fixation on control and its failures — the father who cannot cry for fourteen years and then writes about it with forensic precision, the founder who narrates acquisition deals as if they were heist films, the concertgoer who inventories the sensory data of a stranger collapsing on the floor. The parenthetical asides, the direct addresses to the reader, the constant throat-clearing disclaimers ("house rules," "rule of play," "for avoidance of doubt") — these are not stylistic tics so much as load-bearing architecture. They allow Balterer to approach vulnerability at an angle, to arrive at genuine feeling by pretending to dodge it.

The intellectual timeline reveals a writer who began with entrepreneurial narrative and gradually loosened toward something rawer and more personal, though the two modes never fully separate. The seven-part Smarterer series is the catalog's spine: a serialized founder's memoir that doubles as a study in how deals, relationships, and self-delusion intertwine. But the pieces that genuinely distinguish the work are the ones where commerce falls away and mortality moves in — the father's Parkinson's decline across "Let Go, Dad," "Hospice," and "So Long, Dad" constitutes an involuntary triptych, each installment less defended than the last, the jokes growing thinner as the oxygen does. The father who shouts "I am a carrot! I am a cucumber!" from the edge of death, and the son who recognizes this as a man trying to articulate that he feels like a vegetable — that is writing operating at a level the startup narratives, however entertaining, do not reach. It is also where Balterer's signature move, the deflection into humor, becomes most legible as a survival mechanism rather than a rhetorical strategy.

What keeps the catalog from cohering into something greater is a certain reluctance to let the reader sit in discomfort without a wink. The voice is unmistakable — rapid, digressive, allergic to solemnity, fond of em dashes and sentence fragments that mimic the cadence of a man thinking aloud at a bar. But the relentless knowingness can sand down the edges of pieces that deserve their sharpness. "When You Cry" opens with a confession of startling emotional honesty and almost immediately retreats into ironic distance. The fabricated book review of the writer's own essay, "Invisible," is the most structurally adventurous piece in the catalog, a hall-of-mirrors exercise in self-criticism that reveals how acutely Balterer understands his own tendencies — and how unwilling he remains to fully abandon them. The range is real: from weed memoirs to blockchain analytics, from Miranda July to airplane etiquette to hallucinogenic cult encounters. But the deepest current running beneath all of it is the tension between a man who builds compulsively — businesses, essays, weekly publishing schedules, what he calls "The Machine" — and one who suspects that all this building is an elaborate scaffolding around something he cannot bring himself to simply stand inside and feel.

3
Edition 3 March 7, 2026 · 41 pieces

Balterer's body of work reads like the memoir of a man who cannot stop building things — companies, essays, justifications — and who has come to understand, perhaps only recently, that the compulsion itself is the subject worth examining. Across forty-one pieces, published in a concentrated burst between late 2025 and early 2026, the writer returns obsessively to the tension between control and surrender: the father who won't use a cane, the entrepreneur who micromanages font choices, the insomniac parsing mortality into phases, the man who hasn't cried in fourteen years and describes willing himself toward tears with the mechanical focus of someone debugging code. There is a restless, almost feral energy to the prose — parenthetical asides that undercut the writer's own authority, self-deprecating pivots that function as preemptive strikes against sentimentality, sentences that lunge forward then pull back into wisecracks. The voice is unmistakable: a raconteur who deploys irreverence as structural load-bearing, who uses humor not to avoid depth but to negotiate safe passage toward it. The piece on crying and the pieces on his father's death trace a single arc — the writer circling the problem of male emotional constipation with increasing directness, moving from abstraction in "When You Cry" to the devastating specificity of a dying man shouting "I am a carrot" in "So Long, Dad." That the father predicted his own death on Rosh Hashanah lands with genuine force precisely because Balterer has spent so many words elsewhere resisting exactly this kind of unearned gravity.

The Smarterer series, spanning seven installments, represents both the most sustained narrative effort in the catalog and its most revealing structural choice. Balterer is drawn to the startup founding myth but refuses to play it straight — the co-founder who decamps for Burning Man, the intern who works for free in probable violation of Massachusetts labor law, the acquisition negotiated alongside a romantic entanglement with an employee. The business writing and the personal writing are not, it turns out, separate registers; they are the same register applied to different materials. Whether the subject is a blockchain analytics company, a driver named Maruf who embezzled twenty thousand dollars, or the physiology of a concertgoer collapsing at a Phish show, the method is identical: arrive at the scene with comic bravado, circle the perimeter with anecdote and digression, then drop — sometimes gracefully, sometimes with a thud — into something raw. The Grateful Dead and Phish function as more than biographical color; they are the writer's native liturgy, the framework through which chaos and improvisation are made legible. Tape trading, cult encounters on LSD, the Dead's post-Mydland darkness — these are not nostalgia pieces but attempts to locate the origins of a particular disposition toward risk, community, and the unreliable nature of plans.

What makes this catalog genuinely interesting, rather than merely energetic, is the late emergence of self-scrutiny. The invented book review of "Invisible" — a piece in which Balterer fabricates a critic named V. A. Delbert to pan his own work — is the most formally adventurous thing here, and also the most telling. It suggests a writer who has begun to suspect that his greatest subject might be the gap between performance and interiority, between the guy who commandeers the airplane bathroom and the one who sits by the pool unable to cry while his partner weeps. The Miranda July piece performs a similar function under the guise of a book review: all those preemptive disclaimers about manhood and spoilers are the scaffolding around a writer trying to engage with feminine interiority without the tools to do so comfortably. There are weaknesses — the comic tics can become tics in the clinical sense, repetitive and involuntary; the parenthetical self-interruptions occasionally drain momentum from passages that would land harder if left alone; and the writer's instinct to charm can crowd out the stillness these pieces sometimes desperately need. But the trajectory is clear. Balterer is moving, piece by piece, from a writer who tells stories about things he has done toward a writer reckoning with the person who needed to do them.

2
Edition 2 March 7, 2026 · 41 pieces

Balterer's catalog reads like a man arguing with his own sentimentality — and losing, beautifully, almost every time. Across forty-one pieces, the writer returns obsessively to the gap between the self who feels and the self who refuses to admit it. "When You Cry" opens with a declaration of anger at a partner's tears, then quietly confesses to fourteen years without weeping and a failed, willed attempt to produce some. "So Long, Dad" buries grief inside comedy — a dying man shouting "I am a carrot!" — as though the absurd were the only vessel sturdy enough to carry loss. The posture is tough, wisecracking, deflective, but the architecture of nearly every piece betrays the opposite: Balterer builds elaborate comic scaffolding precisely so he can stand at a height where vulnerability becomes unavoidable. The voice — restless, digressive, conspiratorial, prone to parenthetical asides that function as emotional trap doors — is remarkably consistent whether the subject is hospice care, blockchain analytics, or smoking PCP with a startup employee. This consistency is both the writer's signature and, at times, a limitation: the same tonal register that makes "The Three Phases of Sleep" devastating can make "Who Learned to Read the Water" feel like it's performing intimacy in a boardroom.

The intellectual range here is wider than it first appears, though it clusters around a few gravitational centers: the Grateful Dead and its ecosystem of bootleg tape culture, hallucinogens, and spiritual vagrancy; the serial drama of building and selling companies (BzzAgent, Smarterer, Flipside); the slow erosion of a father's body and autonomy; and the nature of compulsion itself — what the writer names, in "The Machine," as an internal engine that demands construction without offering explanation. The seven-part Smarterer series is the catalog's most ambitious structural undertaking, and it reveals something important about how Balterer thinks about narrative: not as arc but as accretion, each installment layering character, digression, and business mechanics until the sale itself feels less like a climax than an inevitability arrived at sideways. The Dead shows, the startups, the dying father — these are not separate subjects. They are all expressions of the same preoccupation: what it means to be inside an experience that is ending, and how one behaves at the threshold. Tour lots, hospital rooms, acquisition negotiations — each is a liminal space where Balterer stations himself to observe the precise moment something irreversible occurs.

What evolves across the timeline is not so much the voice — which arrives fully formed — but the willingness to let the mask slip longer. The earlier pieces lean harder on comic deflection and meta-commentary ("oh great an article about drugs. try threading this needle, pal"), while the later work, particularly the hospice sequence and the invented book review of the writer's own essay "Invisible," suggests a growing interest in examining the apparatus of self-presentation itself. That "Sunday Edition Review" — a fabricated critical takedown of the writer's own work, written under a pseudonymous byline — is the catalog's most revealing gesture, a man preemptively savaging himself with more precision than any external critic could manage. It is also, not coincidentally, the piece that most nakedly exposes the central contradiction: Balterer writes to be seen, writes about invisibility, writes about the fear of being seen writing about invisibility, and somewhere in that recursive loop, something genuine and unguarded keeps escaping.

1
Edition 1 March 7, 2026 · 41 pieces

Balterer's catalog reads like the work of a man who cannot stop building and cannot stop confessing — and who suspects, perhaps correctly, that these are the same impulse. Across forty-one pieces, the dominant register is a kind of antic intimacy: the writer opens with a provocation, frequently a declarative sentence that lands like a slap or a joke, then peels back into something rawer and more precarious than the opener promised. "When You Cry" begins with the admission of anger at a spouse's tears and tunnels into a fourteen-year drought of the writer's own weeping. "The Machine" personifies the compulsion to create as a hissing, clanging apparatus beyond its host's control. Even the Smarterer series, ostensibly a startup memoir told in seven installments, is less interested in the mechanics of exits and term sheets than in the texture of human friction — the co-founder who needed Burning Man first, the intern who said yes to everything including working for free, the romantic entanglement with an operator whose font preferences became a proxy war for deeper incompatibilities. Balterer is drawn again and again to the moment where competence meets helplessness: the entrepreneur who can orchestrate a $60M acquisition but cannot cry; the son who can manage three hundred guests at an event but cannot let his Parkinson's-afflicted father attend. The prose runs hot, parenthetical, self-interrupting — a voice that trusts digression more than thesis, and that deploys humor as both shield and scalpel.

What emerges over the chronological arc is something like a grief trilogy nested inside a business memoir nested inside a countercultural autobiography. The father pieces — "Let Go, Dad," "Hopsice," "So Long, Dad" — form the emotional spine of the catalog, moving from the discomfort of enforcing boundaries on an aging parent through the institutional indignities of hospitals and hospice to the surreal comedy of a dying man calling his own death date on Rosh Hashanah. These are the essays where the writer's habitual deflections — the asides, the profanity, the winking stage directions — earn their keep, because they dramatize the very mechanism by which a person survives proximity to loss. Alongside these run the Grateful Dead pieces, the weed piece, the cult piece, the hallucinogen-laced wallet misadventure, which collectively sketch a life lived in the orbit of American subcultural excess, from Dead tour tape trading to Phish floors to blockchain analytics. The recurring figure is the hustler-romantic: someone who sold hand-illustrated cassette covers on lot and later sold companies to Pluralsight, who sees no contradiction between the two because both required reading a room and believing in something not yet proven.

The most revealing gesture in the catalog may be piece thirty — the invented "Sunday Edition Review" of the writer's own essay "Invisible," in which a fictional critic named V. A. Delbert takes Balterer to task for mistaking recognition for revelation and for writing safely about safety. It is a startlingly self-aware move, the writer staging his own critical demolition, and it suggests he knows exactly where his tendencies shade into shtick. The parenthetical asides, the conspiratorial second-person address, the reliance on personality as structural principle rather than earned architecture — these are features, not bugs, but they can calcify into mannerism if left unexamined. When Balterer writes about his wife's cleanliness and fruit aversions in the same paragraph as his father's mucous plug and failing lungs, the juxtaposition achieves something no amount of cleverness could engineer: the grotesque ordinary fact of loving people whose bodies betray them. It is in those moments — unguarded, unamused, stripped of the showman's patter — that the writing finds its real frequency.

1
Edition 1 March 8, 2026 · 42 pieces

Balter writes like a man who cannot stop building things and cannot stop narrating the building — companies, essays, marriages, grief, all subjected to the same restless, compulsive energy he names "The Machine." Across this catalog, what emerges is a writer whose central obsession is not entrepreneurship or fatherhood or music or death but the act of self-examination conducted at arm's length, always gesturing toward vulnerability while maintaining an almost pugilistic control over the terms of disclosure. He tells you he hasn't cried in fourteen years, then tells you about the divorce that almost broke him; he announces house rules before reviewing Miranda July; he writes about his dying father through the frame of his wife's feelings about fruit. The digressions are the architecture. Balter's voice — discursive, conspiratorial, syntactically restless, laced with parenthetical hedges and self-interrupting bravado — is unmistakably his own, closer to the spoken rhythms of a Deadhead raconteur than to any essay tradition, and it produces both his best effects and his most persistent limitation: the sense that every confession arrives pre-negotiated, every wound displayed under carefully chosen lighting.

The work evolves from the functional self-help register of the early Inc. piece toward something genuinely stranger and more personal on Balterer, where the Smarterer serial and the father pieces represent twin spines of the project — one tracking the alchemy and absurdity of startup life with novelistic detail (the accidental PCP, the co-founder at Burning Man, the earnout math), the other tracking mortality with increasing directness as the father declines from stubborn patriarch to hospice patient to eulogized absence. The Grateful Dead and Phish threads are not decoration; they are Balter's native cosmology, the place where chaos, communion, and tape-trading fastidiousness converge, and they inform his prose's tolerance for improvisation within structure. The invented book review of his own "Invisible" essay is the catalog's most revealing gesture — a writer so compelled to preempt criticism that he fabricates the critic, essentially arguing with himself in public. The contradictions that define the body of work are productive ones: sentimentality held in check by wisecracks, emotional exposure undermined by disclaimers, a compulsion to connect warring with a terror of being seen trying. What Balter is building, piece by weekly piece, is not a blog but something closer to a serial autobiography in which the narrator keeps insisting he's fine while the evidence accumulates otherwise.

1
Edition 1 March 8, 2026 · 46 pieces

Balter's catalog cleaves into two distinct lives. The early Inc. columns (2011–2013) are competent entrepreneurial counsel — humility, mentorship, competitor strategy — delivered with the authority of a founder who built and sold companies but hadn't yet figured out what he actually wanted to say. They read as transactional, even when confessional, as in the divorce piece where personal wreckage is tidied into lessons. Then something breaks open. The Balterer essays, arriving roughly a decade later, abandon the listicle entirely and reveal a writer who has discovered that voice — digressive, self-interrupting, tonally restless — is itself a form of argument. The seven-part Smarterer series is the fulcrum: ostensibly a startup origin story, it keeps dissolving into accidentally smoking PCP, workplace romance, the petty warfare of font preferences, a wedding where someone insults the company name within earshot. Balter treats entrepreneurship not as a hero's journey but as an accumulation of absurd, compromising, deeply human incidents that resist the clean arc venture capital prefers.

What defines the later work is a compulsive need to circle mortality, embodiment, and the machinery of compulsion while maintaining an almost aggressive comic deflection. The father's decline across "Let Go, Dad," "Hospice," and "So Long, Dad" — where the dying man calls himself a vegetable and then predicts his own death on Rosh Hashanah — is handled with tenderness that never settles into sentimentality because Balter keeps cutting the gravity with structural irreverence: his wife's fruit aversions, hospital bureaucracy, the sheer indignity of mucus plugs. "When You Cry" and "The Machine" expose the writer's two governing contradictions — an emotional constipation that coexists with relentless creative drive, a man who cannot weep but cannot stop building. The Grateful Dead threads (tape dubs, cosmic wallets, Phish floors) aren't nostalgia but epistemology: Balter learned narrative from setlists and bootleg lineage, from the way a show unfolds without a fixed script, and his prose replicates that loose architecture. The invented book review of his own "Invisible" essay is the most telling gesture in the catalog — a writer preemptively critiquing himself before anyone else can, performing self-awareness as both shield and confession, which is finally what all of Balter's work does: it builds the thing and disassembles it simultaneously, daring you to decide which act is the real one.

1
Edition 1 March 24, 2026 · 106 pieces

Balter is a founder who writes like a raconteur and a raconteur who can't stop founding things — and the tension between those two impulses is the engine of the entire catalog. The early work, scattered across Inc columns and Medium investor updates, reads as the expected output of a serial entrepreneur performing competence: leadership listicles, hiring posts with winking irreverence, blockchain industry landscapes. But something shifts, roughly around the sabbatical-era pieces of late 2024 and into 2025, when the voice loosens its tie and starts talking the way it actually thinks. The personal essays — on his father's decline through Parkinson's and death on Rosh Hashanah, on fourteen years without crying, on the fellow airplane passenger whose bathroom he refuses to share — reveal a writer whose natural register is comic deflection deployed against genuinely painful material. Balter parenthesizes his vulnerability, literally bracketing his confessions in asides and self-interruptions, as if sincerity requires a running commentary track to be tolerable. The serialized "Storyer of Smarterer" is the catalog's most ambitious structural gambit: a seven-part startup memoir that treats company-building as picaresque, complete with accidental PCP, romances with co-workers, and acquisition negotiations rendered with the pacing of heist fiction. It works because Balter refuses to sanitize the mess or extract tidy lessons from it.

What recurs, obsessively, is the problem of control — over companies, over grief, over one's own sentimentality. "The Machine" names the compulsion directly: the thing that won't stop building, that drove him into the death industry, into crypto analytics, into whatever came next. The Grateful Dead pieces and the Eggy concert writing function as the catalog's release valve, spaces where surrender to the moment is not weakness but the whole point — and it is no accident that the cult narrative in "The Cosmic Wallet of The Twelve Tribes" begins with losing a wallet, with relinquishing possession. The father pieces — "Let Go, Dad" and "So Long, Dad" — form a devastating pair, the first about refusing his father access to an event, the second about the irreversibility of that kind of gatekeeping once death arrives. Balter writes around his emotions with such practiced evasion that when he finally lands on something direct — "Dad died at 9:44 AM on Rosh Hashanah" — the plainness hits like a detonation. The self-authored negative review of "Invisible" is the most telling artifact in the catalog: a writer who has gotten good enough to anticipate exactly how he will be criticized, and who would rather perform that criticism himself than let anyone else hold the knife. The work is uneven, sometimes self-indulgent, occasionally too pleased with its own digressions — but at its best it captures something real about the particular loneliness of men who build things compulsively and narrate everything except what actually hurts.

Visual Portrait
If your body of work was a picture…
AI-generated visual portrait of Balter's body of work
The floating map and diverging routes capture Balter's restless navigation between Silicon Valley startup culture, blockchain ventures, music touring, and deeply personal essays about fatherhood and loss. The tree whose roots entangle chains and records while its branches become guitars speaks to how entrepreneurship, Grateful Dead-inflected counterculture, and creative writing all grow from the same autobiographical root system. The letters drifting from the backpack and the father-child silhouette on the ridge honor his recurring 'Notes to Flipside' and the tender, grief-steeped meditations on letting go of a dad — the private heart beating inside the hustler's catalog.
Edition 6
Edition 6 · Apr 2026
Edition 5
Edition 5 · Mar 2026
Edition 4
Edition 4 · Mar 2026
Edition 3
Edition 3 · Mar 2026
Edition 2
Edition 2 · Mar 2026
Edition 1
Edition 1 · Mar 2026
Editorial Intelligence
Story Reviews
Individual critical readings of each piece — what works, what resonates, where it sits in the body of work.
On the Proper Hosting of a Ganjarama

The title alone does real work here — "On the Proper Hosting of a Ganjarama" announces itself with the mock-formality of a Victorian etiquette manual applied to something decidedly unVictorian, and that tonal friction is the engine of the piece. The framing as "something between a field guide and a confession" suggests the writer is working in a hybrid mode that risks collapsing into neither — field guides demand authority and distance, confessions demand intimacy and vulnerability, and most attempts to split the difference end up with the breezy non-commitment of a lifestyle blog post. The question is whether the writer earns the confession buried inside the guide, or whether the instructional frame becomes a way to avoid the harder, more personal material.

What's promising is the implication that there's actual craft thinking behind the structure — that the "proper hosting" conceit isn't just a joke but a delivery mechanism for something the writer couldn't say straight. The best pieces in this mode (think John Jeremiah Sullivan, or the gonzo tradition more broadly) use the absurdity of the surface subject to smuggle in genuine reflection about community, ritual, self-presentation, the gap between how we stage experiences and how we actually live them. With only the excerpt and title to work from, there's enough signal here to suggest the writer understands that the comedy is the doorway, not the destination. Whether the piece walks through that doorway or just stands in the frame waving is the difference between something memorable and something that plays well on social media and evaporates.

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1+1+1 = 3

"1+1+1 = 3" — the equation that resolves correctly — paired with the framing that "sometimes your pets are like a math equation" lands somewhere between a cute observation and a missed opportunity. The title promises a kind of playful numerology, a meditation on how discrete beings in a household add up to something that is, in fact, exactly the sum of its parts, or perhaps something more or less than that sum. But the excerpt as presented suggests the piece may settle for the surface charm of pet writing without pushing into the stranger, more interesting territory that the mathematical framing opens up.

Pet essays are one of the most overpopulated and underperforming genres in personal writing, not because the subject is unworthy but because writers tend to stop at affection. The best animal writing — J.R. Ackerley's "My Dog Tulip," parts of Helen Macdonald's "H is for Hawk" — uses the animal as a lens for examining the writer's own blindspots, projections, and failures of understanding. The math conceit here could have been that lens: what does it mean to try to quantify a household's emotional ecology? What breaks when you treat living creatures as integers? The title hints at these questions without, based on what's visible, committing to them. The piece reads as pleasant and affectionate, but it would benefit from the writer asking what the equation can't account for — that's where the real essay lives.

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Jew to Jew

"Jew to Jew" opens with a provocation compressed into four words: "Is this a thing?" That single line, functioning as both excerpt and thesis, does a remarkable amount of work — it signals skepticism, intimacy, and a kind of communal self-interrogation all at once. The title frames the piece as an intra-community conversation, the kind of direct address that implies shared context and shared stakes. Published on Buttondown, a platform that leans toward newsletter-style personal essaying, the framing suggests something closer to a letter than a manifesto, which makes the bluntness of that opening question feel earned rather than glib.

What's frustrating is how little we're given to work with beyond that single line. The question "Is this a thing?" could open into rich territory — identity politics within Jewish communities, the performance of solidarity, denominational friction, diaspora anxiety — but without more text, the piece exists as pure gesture. If the full essay delivers on the tension that opening implies, it could be genuinely compelling. But a provocation is only as good as the argument that follows it, and from what's visible here, the reader is left holding a lit match with nothing to burn.

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2 18 22 Note to Flipside

"2 18 22 Note to Flipside" is one entry in what appears to be an ongoing epistolary series addressed to an entity or person called "Flipside." The date-stamped title structure — no punctuation, no capitalization, just raw chronological markers — suggests a logbook or dispatches from some ongoing project or relationship. Published on Medium, the piece sits within a platform that rewards neither the diaristic nor the experimental particularly well, which raises the question of whether this format is an aesthetic choice or simply a filing system.

The problem with serialized, minimally titled notes published without descriptive framing is that they demand an existing audience. For the uninitiated reader, there is no entry point here — no subtitle, no excerpt, no hook. The "Note to Flipside" conceit could be fascinating if it accumulates into something: a portrait of obsession, a running argument with an alter ego, a crypto trading journal, a spiritual practice. But each installment on its own offers the reader nothing to hold onto. The writer seems to be building something private in a public space, which is either an act of radical vulnerability or an act of indifference toward the reader. Without more text, it's impossible to tell which.

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Editorial Intelligence
Outlet Lens
The same pieces reviewed through the editorial lens of The New Yorker, The Atlantic, and Wired.
"On the Proper Hosting of a Ganjarama"
The Atlantic Take
C-

A piece pitched as something between a field guide and a confession about hosting a cannabis gathering has a narrow aperture for the kind of cultural argument The Atlantic prizes. The question one wants answered is not how to host such an event but what the normalization of cannabis culture tells us about shifting American social contracts, about the collapse of the war on drugs into lifestyle branding, about class and access and who gets to treat their consumption as whimsy rather than felony. Without that connective tissue linking personal anecdote to structural analysis, this reads as a lifestyle essay searching for an intellectual framework it never finds. Pleasant, perhaps, but not the piece that changes how you think about anything beyond your next weekend plans.

Wired Take
D

Unless 'Ganjarama' is the name of a platform, a protocol, or a supply-chain innovation, this piece offers almost nothing for the Wired reader. There is no systems thinking here, no examination of how legalization has spawned new logistics networks, no look at the apps and lab-testing regimes and regulatory tech reshaping the cannabis industry. A personal hosting guide, however witty, belongs to a different editorial universe entirely. We need the map, not the party invite.

The New Yorker Take
B

There is something appealing in the conceit here — the field guide crossed with the confession, a form that promises both taxonomic precision and the vulnerability of self-disclosure, the kind of hybrid that, when it works, produces the sensation of watching someone organize their vices into something resembling civilization. The title alone, with its faintly antiquarian ring, suggests an author aware that social ritual, even disreputable social ritual, deserves the same careful anthropological attention we lavish on dinner parties and funerals. One suspects the piece rewards a patient reader with the small, telling details of hosting etiquette that reveal character under mild intoxication. Yet without the fuller architecture — the scene that lingers, the sentence that turns back on itself with surprise — it is difficult to know whether this rises above the level of charming blog post into something one would press into a friend's hands on the subway.

"1+1+1 = 3"
The Atlantic Take
D+

A personal reflection on pets as a math equation is, to put it plainly, not what this publication does. The Atlantic publishes pieces about animals when those pieces illuminate something about cognition, ecology, the veterinary-industrial complex, or the strange political economy of American pet ownership. A warm meditation on the household chemistry of one's own animals, absent any argumentative ambition or reported depth, would not survive a pitch meeting here. It is not that the writing is necessarily poor — it is that the intellectual stakes are essentially nonexistent for our purposes.

Wired Take
F

This is a personal pet essay. There is no technology angle, no data, no emergent behavior modeled or mapped, no system examined. Unless the author is using machine learning to decode inter-species household dynamics — and nothing in the excerpt suggests they are — this piece has zero editorial relevance to Wired. We would not read past the subject line.

The New Yorker Take
C

The notion that pets constitute a kind of arithmetic — that three living creatures in a household do not simply add up but produce some irreducible sum — is a familiar domestic observation, the sort of thing one might say to a friend over coffee and feel rather pleased about. Whether it sustains a written piece depends entirely on the quality of the observation that follows: the specific cat who sleeps in one precise rectangle of afternoon light, the dog whose anxiety manifests as a compulsion to rearrange shoes. From the excerpt alone, one senses affection but not yet the granular, deeply seen detail that separates the memorable personal essay from the agreeable newsletter post. The math metaphor, cute as it is, risks being the whole trick rather than the door into something richer.

"Jew to Jew"
The Atlantic Take
D

A title like "Jew to Jew" suggests the possibility of an essay that interrogates Jewish identity in a moment of rising antisemitism, generational fracture over Israel, or the complexities of diasporic belonging—any of which would constitute the kind of intellectually ambitious cultural argument The Atlantic seeks. Instead, the excerpt offers a single interrogative sentence with no discernible thesis, framework, or analytical scaffolding. There is no argument here to engage with, no data to weigh, no cultural trend to trace. Whatever conversation the author intended to start, it never begins. The piece fails the most basic editorial test: it does not make the reader rethink anything, because it does not say anything.

Wired Take
F

There is no technology angle, no systems thinking, no network analysis, no forward-looking thesis—nothing that remotely intersects with what Wired publishes or what its readers seek. A three-word excerpt on a Buttondown newsletter about Jewish identity, however potentially meaningful in another context, offers zero signal for an audience interested in how emerging technologies reshape culture, power, and human behavior. This is not a mismatch of degree; it is a mismatch of kind. An editor would not read past the pitch line.

The New Yorker Take
D+

The title, "Jew to Jew," carries the faint promise of something intimate and searching—a reckoning with identity, perhaps, or the kind of intra-communal confession that, in the right hands, becomes universal. What arrives instead is a fragment so spare it barely constitutes a gesture: "Is this a thing?" One waits for the long, discursive unwinding, the details of a particular life colliding with a larger inheritance, and finds instead a question mark hovering in empty air. There is, one supposes, a minimalist audacity in publishing so little, but audacity without craft is merely brevity, and brevity without substance is silence with extra steps. The piece offers nothing for an editor to hold onto—no scene, no texture, no observed human moment—and so it drifts past like a thought someone had in a taxi but never wrote down.

The Catalog

Collected Works

78 total

Notes from the Flipside

13
2 18 22 Note to Flipside
5 13 22 Note to Flipside Re Terra
Note to Flipside Sat 6 25 22
Note to Flipside 10 14 22
Note to Flipside: 3/22/24
Who Learned to Read the Water?
Eight years ago Flipside started doing something that, in retrospect, was either visionary or clinically insane. We decided to normalize blockchain data. Not some blockchain data. All of it. Every chain. Every exchange. Every transaction. Oh, then we obsessively cataloged 700 million wallets to know who is human and which are bots. And who moves what to where and when. Here's what we learned: blockchain data is an ocean. Most people drown in it. Some people build boats that let them float on top to look at the surface. We built a boat, and we learned to read the water. We can tap you on the shoulder and tell you that when a weather front is coming. Or where you should be fishing. That your best users are swimming to another protocol. We give you answers, so you don't wash up shipwrecked on the shore. The Dashboard Problem Can we talk about dashboards? Dashboards are great. We love dashboards. Dashboards are the participation trophies of data analytics: everyone gets one, and everyone
Flipside Rfp Node Infrastructure Partner
Flipside X Prysm X Oan
Blockchain Analytics Industry Landscape May2020
The 93 Best Analytical Brains in Blockchain 2020
Your Investors Favorite Update Flipside March 2020
Introducing the Virtual Color War
Native Token Recycling

The Founder's Mirror

14
Went to Raise Venture Capital
Went to a Crypto Conference
Humility Before a Fall Your Crypto Startup Hasnt Done Anything Yet
Why Join a Board of Directors?
Start-up Strategy: Know Thy Enemy, Befriend Rivals
Originally published in Inc.com
Scrutinize your competitors, and become friends with them, too. You just might partner to pitch a client, buy one out (or vice versa), or grow the industry together.
The Humility Imperative: CEOs, Keep Your Arrogance in Check
Originally published in Inc.com
Dave Balter's ego almost ruined BzzAgent, his fourth start-up, before Tesco's Dunnhumby bought it for a reported $60 million last month. Here, he implores entrepreneurs to find humility.
Leadership & Managing | 10 Ways Any Leader Can Step It Up Today
Originally published in Inc.com
No matter who you are, or the type of company you oversee, there are some universal ways you can be better at it.
Mentor So That It Means Something
Originally published in Inc.com
Being a great mentor requires more than experience and time. Learn to weave the right web. Five steps.
You Can Be an Entrepreneur--and Not Get Divorced
Originally published in Inc.com
Tend to your marriage as carefully as you care for your company. (In other words: Don't do what I did.)
The Machine
You wanna know? It's a Machine that makes me build things. It sounds like the white noise of a TV going off air; it can get uneasy and clang, as if water hammer from the pump of a radiator in winter months. The Machine is a mystery to me, and I'm sure even more so to you. The Machine is a gift or a curse - or maybe a tightrope walk on the razor's edge of both. The Machine hissed relentlessly until I built a business in the death industry in 2014. It became obsessed with the vast acres of graveyards that spill below the flight path of NYC's Laguardia airport. It contemplated death through the lens of the living. Its droning buzz required the stomping of brakes when driving past a cemetery. The Machine didn't care if it was logical or not. The Machine isn't a computer, like Peter Lynch's brain for stock market analysis; if it were asked to code, it wouldn’t be able to decipher between a 0 and a 1. The Machine begs to build, incessantly. It thrives on curiosity, on creativity, on i
Selling BzzAgent
“I've been accused of sexually harassing a black, female co-worker," This the (very caucasian) very Senior Executive proclaimed to me sometime in 2009 - just before informing me that he was leaving the company. And this is how the first sale of BzzAgent fell through. I imagined this Senior Executive was telephoning from the bath, as he would; a space where he offered creative formulations to his countless creative agency underlings, and occasionally squared away large media buys or charmed a client, carefully, like a lion stalking unsuspecting elk. He was British, if memory serves. He was an actual Count, of that I'm sure. He carried an accent that made you susceptible to ideas - like, say, the one where he was going to buy BzzAgent. Looking back I'm not so sure. There wasn't heavy diligence burying us in work we didn't have time to do, nor redlines nor hard-nosed negotiating strategies on indemnification clauses. Nevertheless, on the day he was to get buy-in for his large and formi
Sixteen Lessons on Leadership, with Eskanley Dupitra
I've managed over 1,000 people in 30 years. Yes you read that right. And here's exactly what I've learned in sixteen lessons. Well... Not directly 1,000, more like a few hundred who managed all the others. But, yeah, I occasionally stretch the truth (which you should do, lesson #1) and I like to maybe sometimes go around or down or under or sideways or whatever one might call it, and manage the manager's managee directly.  Which doesn't discount my management capacity any, mind you. Rather that sometimes, as a leader, the chain of command is pointless and as indirect as insurrection (lesson #2). And sometimes it's your job to be present for anyone and everyone, no matter who they are in the company (lesson #2A). As for the people I manage directly, I've learned that micromanagement is both a sin and a blessing. And mostly micromanagement gets a bad rap (lesson #3). That's right, because it's my way or the highway (lesson #4), and many of your direct reports will begin their journey

The Storyer of Smarterer

9
Series The Storyer of Smarterer 7 parts
The Storyer of Smarterer (Part I)
The first potential technical co-founder of Smarterer couldn't start exactly just yet. Nope, he had to go to Burning Man first. To 'free his mind.' Naturally. This shortly after agreeing to be a co-founder, but first taking a 6-week trip to some unpronounceable jungle on some unchartered continent. So I told him he wasn't co-founder material. That he lacked commitment. This potential co-founder thought of me as an a∞hole. Not that he was incorrect - but two wrongs don't make a right. The second (potential) technical co-founder of Smarterer and I met once a week. He understood the vision: To validate anyone's skill in anything - be it excel or python or R or photoshop - in just 10 questions, 120 seconds. In cafes we snorted coffee and bonded. I the forty-ish elder statesman of entrepreneurship, he the shaggy-haired, wet-behind-the-ears technical wonderboy. But he found the technical challenge a jigsaw puzzle, with edges bent and cardboard frayed and pieces missing. After near
The Storyer of Smarterer (Part II)
“Smarterer? That's absolutely the stupidest name for a company possible." This overheard at Luke Miller's wedding in 2025, from the table next to ours - oblivious that one of Smarterer's founders was within earshot. Luke's brother was giving the Best Man speech, and was riffing on the fact that Luke seemed to make illogical career choices - until they turned out to be brilliant or prophetic. One such choice was joining skills-assessment startup Smarterer as an intern, where he eventually rose to a product manager during the successful sale to Pluralsight in 2014. Was Luke lucky or smart? Well his next gig was as an early employee at some non-profit which happened to be named, get this...OpenAI. (Current value of OpenAI, $500b, so, you decide.) But this is all later, because back in 2011 Smarterer wasn't even off the ground, and Luke Miller wasn't even employed yet, and the company was seeking a CEO to work alongside Mike PK. As Exec. Chair the plan was for me to maintain the visi
The Storyer of Smarterer (part III)
The Storyer of Smarterer (Part IV)
The Storyer of Smarterer (Part V)
We sat by the pool and cried for about twelve hours. Well, I didn't cry, that's not in my nature. But Hodges did plenty - after she reminded me just how unfair the choice was she had to make. Let's square the facts and circle the truths shall we? As the incoming CEO I managed Sarah Hodges and we both were, well, strong of opinion. In truth, Hodges is more talented than most operators you'll work with in three lifetimes. She both plans and executes. She creates signal from noise and accepts nothing less than exceptional. She can market. She navigates spreadsheets. She builds relationships. She knows when to clown and when to buckle down. I'm a visionary and she's an operator, which made our work together a magnetic sort of chemistry - marred mostly by our commitments to individual peccadillos. Hodges would build a deck and I would change the fonts and back and forth we'd go. Sure it sounds silly, but serifs matter to me and Arial Sans to her and a little paper-cut argument would b
The Storyer of Smarterer (part V)
The Storyer of Smarterer (Part VI)
The Storyer of Smarterer (part VII, final chapter)
A lady never kisses and tells. But then again (at least the last time I checked), I’m no lady. So how about I let you in on a little smoochy smoochy. To whet the proverbial whistle, let’s sashay over to the math of BzzAgent. In 2005 we raised $13.8M in venture capital and sold for $60M five years later. Valuations matter, which is why our venture partners only got their money back - while employees and earlier angel investors hit the proverbial financial homerun. (for avoidance of doubt: I didn’t personally make that $60M. I was a piece of the puzzle, not the whole jigsaw) BzzAgent's return came with a kink or two, namely in the form of an 'earnout': In order to receive the sale proceeds, I had to stay employed for four years and the company had to hit certain business targets. “Earnouts: rarely earned, always paid,” is a banker's adage, referencing the battles that often come with them. And true to fashion, after slight disagreements on direction, we honey badgered our way to a n
The Storyer of Smarterer

Grief Work

6
So Long Dad
Let Go Dad
Hopsice
My wife doesn't like fruit. For real, I mean it. Like any fruit. Actually, she'll tell you, she only likes fresh crisp apples and watermelon - in season. As for eggs, no, they're not for her. Nor gummy candy. Mayo is her yuck to my yum. Possibly related, or maybe not, she's also really clean. The house, and the order of things, namely. You might call her meticulous, with such an artful eye that you won't even notice the lack of a crumb or the chairs lined up straight as soldiers. My Wife is with me when I receive Sunday's call that they have taken Dad to Cambridge Hospital. Spaulding has given up on rehabilitation; they say they couldn't provide him the medical care he needed. He woke with aspiration in his lungs or a - cover your ears - mucous plug, and required additional oxygen. This after Spaulding's most unsanitary situation provided him a full month of catching pneumonia and then teeth-kicking Covid. And so with a nose tube feeding him medicine, they closed his door to leave him
Hospice
The Three Phases of Sleep
When You Cry
When you cry, I get angry. It's a kneejerk, a reflex, an impulse. I don't search to understand your sadness. I just want your goddamn crying to stop. What does crying even do for you anyway? I mean - if I'm being truthful - it appears to be a totally unpleasant experience. You see the irony here right? The actual act of crying is so absurdly awful it would, well, it would be enough to make one want to cry (if you were able to do that sort of thing, of course). It's true, by last count, I haven't cried in at least fourteen years. Back then, I was going through a divorce and, yes (contrary to popular belief), I do feel sadnes. Damn I missed my kids; I missed what I thought my life would look like; I feared change tremendously. I was advised crying might make feel better, and I suppose it was as good advice as any. So I willed myself to focus on the space between my eyes; I dwelled on my sadness, digging deep into loneliness that burned like poison ivy. I blinked hard, quickly. I fr

Dead Lots & Cosmic Trails

12
The Cosmic Wallet of The Twelve Tribes
Tape Dubs
My first real business was selling tape covers on Grateful Dead Tour. You know, tape covers. For cassettes, of course. I mean, it solved real pain. Like, what else would you put on your bootleg of 5/8/77? Tape trading was a fine art for the musically obsessed and supremely nerdy. You might procure a brick of blank Maxell XLIIs from Radio Shack and borrow a few bootlegs from another Deadhead. Then you'd load their tape in your source, maybe a Sony TC-K677 3-head, connected via line-in to an NAAC Nakamichi Dragon, tweaking levels and simultaneously pressing play on the first and record on the second. Labeling mattered to cassette-trading audiophiles. If the source bootleg was a gen1, the recorded copy would be a gen2. A ‘crispy’ pristine Betty Cantor-Jackson SDBD was coveted fare; rumors always swirled of undiscovered releases. What made my tape covers special? The art, of course. I'd produce a template, then enlist Mike, my often-stoned roommate to illustrate something - say Jerry's
Guyute, The Ugly Pig
This particular gent went down. Hard. Dropped straight, as if sucker punched on the chin. Crumpled, like a napkin on a dinner plate. Timing is everything and, well, in this case, we weren't even two minutes into the opening song: 46 Days. It was almost as if the band sensed the commotion and sought to lean further into the muck. This was, after all, Bill Graham Civic Auditorium, July of 2018, and a general admission indoor show in the height of summer. The next time they'd roll through (it would take nearly seven years) the floor would be packed like sardines, but back then it felt almost roomy - like a deep conversation scattered with comfortable pauses. Had there been rows of seats, with assigned numbers just so, you'd say this was six to eight rows back, and just slightly to the right, Mike side. This a spot one might covet. A spot one might spend the previous week thinking all about, because weeks and months and years are measured by tours and shows to attend. This particular gent
Eggy @ Toad's
Does Eggy headlining Toad's Place in New Haven as their last official show of 2025 signify anything? Anything at all? Why yes. Yes it does. If you're into technicalities, this was the 94th show of an extremely productive, profound, and practically revolutionary year for Eggy. And Toad's Place provided an opportunity to reflect on it all. Let's start at the beginning: Toad's was the first place Eggy played as a band - ever. It's hometown court, so to speak. A room they've inhabited many times over the years — but never as the lead act, let alone packed to the gills with New Haven faithful. Eggy is known for many things, and one of those things happens to be the long thread of patience that pervades their presence. Over years and years of practice, and of gigs and gigs in countless venues, Eggy has earned every right to be here at Toad's at this very time on this very night. {x}The mood is festive. Celebratory. The air drips with a well-cultivated magnetism - even before Residual Groov
Tour is Adventure
Tour is Adventure
I ️ Tour
Eggy Tour Socks
Hah Much Do Ah Oh Yah
The Weed
I like The Weed. And she’s a tempestuous bitch. (oh great an article about drugs. try threading this needle, pal) I mean that kindly and with all due respect. One pip’s drug, another tip’s medicine, and all that jazz. I’m not here to croon a drugged-out love song, and won’t be decrying the evils of moderate addictions. Rule of play: no preesh and no preach. We got that? Let’s start with Willie. Willie Berkowitz introduced me to The Weed, at my ripe age of thirteen, tucked in between two pole vaulter’s 20' gym mats during gym class. We nestled deep in the high density polyurethane foam, and Willie — an upper-classman with a speckled history — offered a hit from a ‘sneak-a-toke’ brass pipe (you know, the kind with the squeaky screw off top). I can say confidently today that what Willie provided was ‘dirt weed’. Mostly stems and seeds — but enough to make me droopy and giggly, which surely no one noticed because I wasn’t all that good at track and field anyway. The Weed love affair began,
I Like the Weed
On the Proper Hosting of a Ganjarama
Originally published in buttondown.com
Something between a field guide and a confession

Strangers in Transit

5

The Writing Life

10
A minor in memories
I like to write. It's true. No really, I do. Seriously. I do. Why won't you believe me? Writing isn't work. It's a habit. It's the crawl space of my mind; writing feels snug, like the stretch in a new pair of socks. Years ago, an executive on my team offered, 'I write better than I speak' - an idea which I've now absconded with and taken as my own. Ideas to write about resolve like cars on an eight-lane freeway. Sometimes there's a stream of them, boxing each other out, competing for the speed of the left lane. Sometimes the idea highway feels like three AM, lit up by overheads, but sparse of any traffic at all. I write to publish every week, a nasty case of the 10,000 hours. It's partially to exercise the muscle, but mostly because it's a calendar I can count on. It's rhythm, whether the writing is good or bad, whether I have time or not. Most weeks I work up a piece on Saturday, first thing in the morning, a dented and malformed cast of a thing. Editing is really the art, becaus
I Read Miranda Julys All Fours and I M a Man
Why My New Book is Destined to Fail
Sunday Edition Review: Invisible
Invisible
Sometimes a Money Shot is Just a Money Shot
And, so be it, We're Down to the Short Strokes. Please, if you have children in the room, ear muffs. This may get a tad filthy. Because this is a piece about the things we say: The colloquialisms, the off-hands, and the normative asides we offer that, well, we probably shouldn't. In plain corporate jargon, Down to the Short Strokes would suggest the end of a negotiation or maybe the completion of a months-long project. Which, maybe, because, I guess (if one were to infer), the long strokes would be, well, the beginning of a sexual and handsy tête-à-tête. The short strokes then would be, mainly, I think, a series of rapid movements to culminate the finish, as it were. <scratches 'Short Strokes' off everyday talk track> But how about Hot to Trot, the mid-20th century slang connecting your eagerness with the anxiety of a tied-up horse? You clearly remember Shalamar's 1982 disco hit, A Night to Remember, with the catchy chorus, Hot to Trot, leaving no doubt about the term's promiscuity -
How Does One Write for a Band Really
1+1+1 = 3
Originally published in buttondown.com
Sometimes your pets are like a math equation
Jew to Jew
Originally published in buttondown.com
Is this a thing?
Hot and Sour Soup

Seeking Brilliant Misfits

9
AI-Ready Portfolio

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