Ben Settle didn’t start his online business with a clear roadmap; he started confused, chasing shiny objects, and making the same mistakes most beginners make. In this episode, he pulls back the curtain on his journey: the false starts, the shortcuts that backfired, and the hard lessons that actually moved the needle.
GUEST:
Ben Settle is a direct-response copywriter and email marketer known for championing the “daily email” approach to selling. He built his brand by sending short, personality-driven emails that pitch almost every day, emphasizing strong voice, polarization, and consistency over fancy funnels. He publishes a paid print newsletter called Email Players and has created books and trainings on copywriting, persuasion, and list monetization, making him a recognizable figure in modern email marketing.
[1:39] Forget Everything You Know About AI:
- Technologies framed as revolutionary often follow patterns anticipated by earlier cultural narratives and anxieties, revealing more about human psychology than about the technologies themselves.
- What is labeled “intelligence” in machines may more accurately reflect advanced pattern recognition and statistical interpolation, valuable yet categorically distinct from human cognition.
- The perception of urgency around adopting new tools frequently stems from social signaling rather than demonstrable shifts in core business outcomes.
- Market enthusiasm for emerging sectors can create financial opportunity not through participation in the trend, but through strategic detachment, profiting from volatility generated by collective overvaluation.
- Real-world utility of a tool is not disproven by skepticism, nor guaranteed by hype; its value is revealed only when anchored to concrete, measurable results in specific operational contexts.
- A mature relationship with technology involves discernment, not wholesale rejection or adoption, but calibrated use based on whether it solves an actual problem better than existing alternatives.
- The loudest advocates for a paradigm shift are often those least exposed to its long-term performance under real constraints.
- Profitability and technological novelty operate on independent axes; an industry can expand rapidly while remaining fundamentally unprofitable at the enterprise level.
- Tools gain power not from their inherent sophistication, but from their integration into workflows where human judgment remains the decisive variable.
- The endurance of foundational business principles (clarity, trust, relevance, consistency) outlasts successive waves of technological disruption, precisely because they address unchanging aspects of human behavior.
[8:52] Stop Losing Money to AI Trends:
- The true test of a tool’s value is not whether it can generate output, but whether it meaningfully accelerates insight, judgment, or original synthesis.
- Productivity theater thrives during hype cycles, where activity masquerades as progress and novelty substitutes for results.
- Dependence on infrastructure you don’t control (domains, IPs, algorithms, platforms) introduces fragility that no amount of content velocity can compensate for.
- Human cognition remains irreplaceable not because it’s flawless, but because it integrates ambiguity, contradiction, and lived context in ways statistical models inherently cannot.
- Markets self-correct not by rejecting new tools, but by punishing those who confuse tool proficiency with business acumen, especially when the former masks the absence of the latter.
- Filtering noise requires ever more sophisticated signal detection, making attention, taste, and editorial judgment increasingly scarce and valuable assets.
- A tool’s highest utility often lies not in execution, but in “provocation”: triggering human ideation by presenting flawed, partial, or absurd options that spark better thinking through contrast.
- Enduring media forms persist not due to nostalgia, but because they align with stable human behaviors that no interface redesign can overwrite.
[12:20] Why AI Is the Fake Louboutin of Marketing:
- Persuasion rooted in authenticity carries a signature that resists replication because it emerges from lived contradiction, not optimized output.
- Imitation without understanding produces surface resemblance but fails to transmit the internal logic that makes communication resonate and convert.
- Value is not in the artifact, but in the provenance: audiences increasingly detect and discount content that lacks the imprint of human stakes, struggle, or specificity.
- Scarcity shifts from attention to trust, and trust is eroded not by volume but by indistinguishability, where everything begins to sound like everything else.
- A market saturated with “good enough” rewards not efficiency, but distinction, especially distinction earned through deliberate imperfection, personal risk, or unscalable craft.
- Cultural shortcuts work only until the audience develops immunity, which it always does.
- The most potent brands endure not because they’re flawless, but because they’re unmistakable, anchored in a coherent worldview that no algorithm can reverse-engineer.
- Technological mimicry excels at recombination, but falters at invention, particularly the kind of invention that arises from frustration, obsession, or moral conviction.
- When tools lower the cost of production below the cost of discernment, the market corrects by elevating curation, provenance, and human signature as premium filters.
[18:57] The Real Job That Makes You a Great Marketer:
- Skill without service is performance; true persuasion arises not from technique alone, but from the habit of anticipating and honoring another’s unspoken need.
- Human communication is calibrated in real time through friction and those micro-adjustments cannot be simulated, only lived.
- The fastest path to voice is not optimization, but exposure: repeated, unfiltered interaction with people who have no obligation to listen sharpens clarity more than any prompt ever could.
- ]Ownership of audience and ownership of message reinforce each other; outsourcing one erodes the other, until both become hollow rituals of extraction rather than exchange.
- Mastery is forged in constraint: limited time, small lists, modest offers, these force precision, eliminate fluff, and reveal what actually moves people, stripped of scale or spectacle.
- The difference between “content” and “communication” is intent: one seeks attention, the other seeks understanding, and only the latter builds durable influence.
- Apprenticeship to craft begins not with tools, but with humility: serving others without agenda rewires instinct toward generosity, which is the bedrock of persuasion.
- Daily creation anchored in real-world feedback is the only reliable antidote to abstraction, theory, and the illusion of progress.
- Talent may be innate, but trustworthiness is earned, and in markets flooded with mimicry, it is the scarcest, most defensible asset any communicator can possess.
[24:52] The Service Secret AI Will Never Have:
- Exceptional service isn’t defined by compliance with procedure, but by voluntary deviation, the moment someone chooses to go beyond obligation without expectation of reward.
- Trust is not built through flawless transactions, but through the perception that the other party cares more about your outcome than their convenience.
- ]Price sensitivity collapses in the presence of genuine regard; people willingly pay more, not for features, but for the relief of being seen, believed, and prioritized.
- Friction in resolution acts as a silent tax on goodwill, eroding lifetime value faster than any product flaw ever could.
- A brand’s true margin isn’t financial, it’s relational: the surplus of goodwill that allows it to survive mistakes, raise prices, or delay delivery without defection.
- The highest form of professionalism is “unscripted decency” acting with integrity not because it’s policy, but because it would feel wrong not to.
[33:01] How to Spot AI Copy Before Your Customers Do:
- Human expression carries subconscious cadence (imperfect rhythm, asymmetric emphasis, unresolved tension) that AI, trained on consensus patterns, systematically over-smooths into neutrality.
- Persuasive language thrives on “controlled vulnerability”: the willingness to risk being wrong, to reveal bias, to admit limitation, none of which an optimization engine can ethically or structurally replicate.
- Markets self-regulate not by banning imitation, but by evolving taste: as synthetic output floods the zone, audiences develop immunity and begin craving the subtle imperfections that only embodied experience produces.
- Legitimacy is not declared, it is incurred, through exposure to consequence, contradiction, and correction over time; no prompt can simulate the weight of having been wrong in public and lived to revise.
- The more tools promise frictionless creation, the more audiences equate ease with evasion, and the more they reward communication that bears the marks of struggle, revision, and personal risk.
- Regulatory labeling of AI content won’t stem its us, it will accelerate the premium on “unlabeled” human work, much as “organic” certification elevated, but also dilutedthe value of the term.
- Ultimately, the distinction between human and machine isn’t semantic; it’s moral: one speaks from accountability, the other from simulation, and over time, even the distracted can feel the difference in their bones.
[36:14] Why the Future Belongs to Craftsmen Not AI:
- The most potent raw material for persuasion isn’t data or structure, it’s unscripted human residue: digressions, repetitions, emotional spikes, and verbal tics that reveal what the speaker truly cares about, often in spite of themselves.
- Mastery reveals itself not in flawless delivery, but in selective imperfection: the hesitation held for effect, the repetition that signals emphasis, the colloquialism that builds kinship, all calibrated by ear, not algorithm.
- AI-assisted editing only amplifies value when the human has already done the “unquantifiable work”: lived the problem, felt the stakes, and wrestled meaning from ambiguity.
- When communication becomes too smooth, it becomes suspect; audiences increasingly interpret polish as evasion, and prefer the rough edge of someone who hasn’t sanitized their conviction.
- The future premium belongs not to those who produce fastest, but to those who can “recognize signal in noise” especially when the noise is their own client’s confusion, passion, or contradiction.
- To be a craftsman is to accept that your medium is not words, but trust, and trust is built syllable by syllable, in the gaps between what is said and what is meant.
[39:06] The Steve Jobs Secret AI Can’t Copy:
- The marketplace rewards not output, but *evidence of care*—and care reveals itself in asymmetry: disproportionate effort applied to hidden details, precisely because they’re hidden.
- Production, not consumption, is the primal engine of confidence: each shipped offer, however imperfect, recalibrates self-perception from “aspiring” to “practicing,” and that shift is irreversible.
- Flaws, when acknowledged and integrated, become vectors of trust: perfection repels; humanity (struggle, contradiction, repair) invites collaboration.
- The pursuit of success decays when detached from identity: when money becomes the goal rather than the byproduct of solving real problems for real people, effort becomes transactional and brittle.
- True differentiation emerges not from novelty, but from depth of commitment, the refusal to let the market’s impatience dictate the pace of one’s own rigor.
- The craftsman’s edge lies in a paradox: they serve the audience so completely that their own standards,become the only viable benchmark.
[45:44] Why Your Flaws Make You Uncopyable:
- Flaw is the engine of relatability, audiences connect not to perfection, but to recognizable struggle; the moment a communicator reveals where they faltered, they grant permission for the reader to do the same.
- Drama arises from deviation, not discipline: the story of someone who finally acted after years of delay holds more narrative power than the chronicle of consistent excellence, because tension requires rupture.
- The “prodigal” archetype resonates because redemption is participatory, people don’t just admire the turnaround; they project themselves into it, seeing their own unfinished chapters reflected.
- Authentic voice emerges not from polish, but from frictio: the rough edges of personality, when retained rather than smoothed, signal that the speaker has not outsourced their humanity to optimization.
- Great storytelling doesn’t hide the wound, it makes the wound the doorway, tthe deeper and more specific the disclosed flaw, the stronger the implied promise: This insight was paid for in real currency.
- Audiences forgive abrasion, excess, or contradiction far more readily than they forgive inauthenticity disguised as virtue.
- AI cannot replicate the tonal residue of lived repair: the subtle shift in language after failure, the calibrated humility after overreach, the quiet authority of someone who revised themselves in public.
- The most persuasive communicators don’t transcend their flaws, they deploy them, turning vulnerability into velocity, stigma into solidarity, and misstep into mission.
[51:30] What Business Are You Really In:
- The surface activity is rarely the core business: what you “do” is often just the vehicle; what you “solve” (or enable, or embody) is the true market you occupy.
- Shifting from “I sell X” to “I enable Y” unlocks new pricing power, audience alignment, and strategic flexibility that operational focus alone cannot provide.
- The most durable businesses solve emotional or existential needs masquerading as functional ones; Subway didn’t sell sandwiches; it sold permission to indulge while believing you were being virtuous.
- True scalability emerges when income decouples from time-bound output: a trading account compounds; a newsletter scales linearly. Recognizing which asset class you’re really building determines long-term trajectory.
- Self-inquiry ”What business am I truly in?” is not a one-time exercise, but a recursive filter that should be applied whenever growth stalls, competition intensifies, or motivation wanes.
- Positioning is not messaging, it’s ontologY: how you internally categorize your work shapes what you notice, what you measure, and what opportunities you’re even capable of seeing.
- The highest-margin insight is often meta: not how to do your work better, but why it matters, and whether you’ve mistaken the ritual for the result.
- Mastery of craft is necessary but insufficient without periodic redefinition of “what the craft is in service of”, even excellence becomes a trap of diminishing returns.
[54:39] Ben Settles’ Expertise:
- Head to bensettle.com. Join the list to get the first issue of the Email Players newsletter free in PDF format, and learn about Ben’s physical newsletter. You’ll also find the Email Player Schema Book and related materials that have inspired seminars and trainings. These resources show step-by-step ways to make more sales with email, including what works right now in the AI era.
[1:02:13] Igor’s Book On Email Marketing:
- Visit www.igorsbook.com to learn more.
