Original Question
(Submitted by John P.) "I live in LA and have run across hundreds if not thousands of guys aged in their late 50s and older who have these successful, but very small businesses.They make a few million a year - usually have a small office or warehouse, and a few employees. Continual side deals in the mix. Seems like they peaked at least a decade ago and then never really left that bracket. Maybe they get into a few bigger things, something like a real estate opportunity with other same-level guys, making them another few million but basically all similar stuff. They are gradually gaining wealth through increasing access to opportunity, but their businesses never evolve into anything substantial. When I see their 1990’s looking business card, yahoo emails, website, products, etc. I’m completely shocked - how can they be making that kind of money? Rarely have I met someone who’s built a legit corporation. Obviously this is an over generalization…but also kind of not. What is this or is it me missing something?"
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The most common pattern I observe in US-based entrepreneurs, even those generating millions in annual revenue, is a disconnect primarily manifesting in two domains: inexperience managing growth and a failure to grasp the pivotal role of emergent technology.
Everything evolves, but the pace of change today has broken from all precedent. McKinsey estimated in 2015 that disruption was occurring ten times faster than the decade prior. Now, forecasts for 2025 through 2035suggest acceleration at thirtyfold speed and up to 1,000 times the scale of the Industrial Revolution. What once unfolded over a century may now condense into a single decade (Dobbs et al., 2015; McKinsey & Co, 2024). While these entrepreneurs move within movement, their businesses are certainly not involved with leading it.
Momentum Without Maturity
Most entrepreneurs have never operated for any significant length inside high-level enterprises where scale is orchestrated through systems. Without this intelligence, their belief is that business building is an extension of personality rather than an act of engineering. They continue to latch onto raw instincts such as deal-making, charisma, and sheer will, that subsidized inaugural success. Yet, growth exposes the fragility of these habits. They avoid engaging specialized advisors who could refine their approach and instead lean on accustomed playbooks, mistaking former momentum for modern mastery (Hamm, 2002). Whether from misplaced confidence or cultivated isolation, past victories cast a deceptive veil of universal competence (Dunning & Kruger,1999; Healy, 2016). Compounding this, cognitive prejudices such as confirmation bias lead to seeking counsel that echoes their own limited views, while the sunk cost fallacy binds them to antiquated procedures (Tversky & Kahneman,1974).
Embedded within this incoherence is another distortion: strategy mistaken for effort. Elevation is misread not as a function of structure, but as a demand for unrelenting effort, and in doing so, they quietly justify inertia. What appears as contentment with modest outcomes conceals a shortage of ambition, not always willful complacency, but a collapse of imagination shaped by narrow models of what’s possible. This insulation breeds a cycle of missed opportunities for fervent expansion. Alternatively, they commonly rotate through a series of smaller viable ventures that again fall short of systemic potential, lacking the acumen to pursue endeavors of increasing size (Hamm,2002). They move laterally, not vertically - circulating within comfort zones, but never breaching the thresholds that define commercial altitude.
This behavioral tendency is most visible among those whose ascent began before the digital paradigm matured. Meanwhile, the often younger cohort, unburdened by legacy systems and lacking the polish of formal corporate discipline, maneuvers through frontline intricacy with remarkable articulacy. Despite inexperience, they instinctively grasp patterns by leveraging tools that sharpen understanding, form possibilities, and reveal liabilities. This intellectual agility stems not from years of practice but from an innate alignment with technologies that compress the arc of aptitude.
Miscalculating What Matters
A subtler impediment lies in the intricate bond with wealth itself. Entrepreneurs who forged fortunes through personal endeavors habitually view each dollar as a fragment of one’s own essence, a reflex that interferes with their approach to investing in talent and infrastructure. Unlike corporate stewards who allocate funds with measured detachment, these visionaries balk at paying premium rates for expertise, even when the returns promise to out strip the expense. This reluctance arises not out of resource scarcity but from a lingering ethos of early-stage frugality or formative economic scarcity, steered by cultural or generational currents still misaligned with prevailing market realities. For those hailing from constrained backgrounds, including immigrant entrepreneurs, a perceptual lag persists: what once felt extravagant now constitutes the basis of strategic investment. Although accepting indulgent lifestyle opulence, their company suffers from chronic neglect of the visionary mind capable of transforming competent to iconic.
Raised status does more than influence spending, it distorts discernment. Proximity to elite circles through geography, social networks, or fleeting collaborations, creates a mirage of relevance. Individuals brush shoulders with sophistication but fail to speak its language, confounding adjacency for fluency (Festinger, 1954). More dangerously, this vicinage becomes a feedback loop of false validation. Casual recognition from high-status figures is interpreted as endorsement and passing praise substitutes for rigorous critique. Exposure to accomplished settings leads to fixation on cosmetic refinement, while underlying capability remains undeveloped. The result is leadership calibrated for appearance rather than substance. Surrounded by excellence, they conflate visibility with viability. Their status shields them against candid feedback, as employees, partners, and those within private circles hesitate to challenge entrenched customs (Brown & Eisenhardt,1997). To those attuned with current standards, this gap is glaring, yet the entrepreneurs remain largely unaware - grand visions betrayed by execution that, to any informed observer, appear strikingly amateur.
Outside the Curve
The business landscape has been reshaped by a relentless tide of technological and societal evolution, a shift countless owners misconstrued at their peril. What was once a manageable divide has become a chasm, widened by the accelerating pace of change. In the early 2000s, analog instincts could still suffice, but today, every enterprise is entwined with technology and media, spotlighting those who lag (Kinni, 2016). Each day amplifies the hallow between inadequate methods and the fluid actualities of contemporary commerce. They disregard the degree to which software redefines operational flow, how interfaces mold user conduct, or how digital ecosystems reshape significance, positioning, and perception. Equally critical and overlooked is how client choices hinge on experience over sensibleness and how aesthetics serve as conduits of trust (PwC, 2025).
Beyond technology, cultural currents further display the mounting severance. Savvy consumers demand interaction imbued with authenticity and seamless digital integration, while investors favor endeavors wielding data with precision and harmonized with societal values like sustainability (Edelman, 2024). Digitally-native entrepreneurs, proficient in platforms that deliver real-time feedback, are outpacing their competitors with intuitive command of these dynamics (Gartner, 2023). Whereas over 80% of Fortune 500 companies weave AI into their operations, many owners, particularly from earlier generations, waver to embrace this shift, treating technology as an appendage rather than the core of strategy (McKinsey & Company, 2024; Loo et al.,2024). This is a conceptual failing, not merely a tactical one, leaving their pursuits less resonant in a world that rewards nuance over noise.
Yesterday Isn’t Enough
These founders navigate a transformed commercial, contextual,and operational terrain with impulse honed in a bygone era. Nevertheless, armed with capital and the legitimacy of prior outcomes, some continue to believe they are equipped to pursue bolder initiatives - sprawling real estate developments, premium consumer brands, or, ironically, tech innovation. Their propositions resonate with today’s markets, but internal function remains anchored in outdated logic. This dissonance deepens as they surround themselves with others who echo the same distortions, misinterpreting familiarity as qualification (Brown & Eisenhardt, 1997).
At this echelon, meaningful progression demands asymmetry; access to expertise, instruments, and perspective that far exceed existing awareness. The most effective entrepreneurs have discerned the limits of their utility and deliberately constructed environments where sharper intelligence drives the agenda (Senge, 1990). For those who have yet to confront this, potential remains, but only if detachment from legacy thinking overtakes the comfort of repetition. What is exceptional never emerges from what is merely established.
