Throughout his youth and into early adulthood, Kyle Ray never truly found a sense of ease or belonging within the traditional classroom environment. Academic settings, with their rigid structures and defined expectations, often left him feeling out of place and disengaged. Reflecting on those formative years, Ray has openly acknowledged that his performance in school was far from exceptional. He recalls being told by an authority figure that the most he could realistically aspire to was managing a restaurant—a comment meant perhaps as pragmatic advice, but one that instead ignited a powerful and enduring internal motivation. Determined to defy that limiting forecast, Ray converted the discouragement into fuel, a persistent drive to prove the skeptics wrong. Even years later, he admits that this early doubt continues to shape his ambition, pushing him to achieve beyond the narrow boundaries once set for him.
Today, Ray stands as a thriving entrepreneur who turned what once began as a modest side hustle—cleaning windows on evenings and weekends—into a highly profitable, six‑figure enterprise. His company, Geek Window Cleaning, now services hundreds of clients throughout Houston and Austin, offering professional window cleaning to both residential and commercial properties. Yet his journey from scraping by to running a flourishing business was neither swift nor simple. Without the foundation of a college education or the advantages of a formal business degree, Ray sought knowledge in a different form. He became a devoted self‑educator, leveraging the insights and frameworks found in books to close the gap left by his lack of formal training. For years, while bartending and waiting tables to sustain his livelihood, he devoted his spare time to learning everything he could about entrepreneurship, leadership, and personal development. Slowly, after nearly seven years of consistent effort, the returns from his part‑time venture finally outpaced the income from his service jobs, allowing him to leave them behind and dedicate himself fully to building his company.
Despite his success, Ray has never stopped learning. He made reading an integral part of his professional routine and personal discipline. Committed to steady self-improvement, he sets the goal of completing at least one book every month. To maintain accountability and make the process both motivating and rewarding, he devised a clever and unusual strategy. Instead of an ordinary bookmark, Ray places a crisp $100 bill between the pages of whatever book he is currently reading. He jokingly calls it his “reading hack,” but the method is a serious tool for commitment. Only when he finishes the book in its entirety does he allow himself the pleasure of spending that money. The tangible reward transforms reading from a passive task into an active challenge—one that literally equates new knowledge with financial value.
The rule, however, comes with a thoughtful limitation: the prize cannot be put toward anything related to work. By separating the reward from his business pursuits, Ray ensures that the act of learning remains intrinsically valuable rather than simply transactional. Occasionally, he takes the bill from one completed book and adds it to the next, saving up a few hundred dollars. When he and his wife accumulate enough, they treat themselves to something memorable—often an indulgent dinner or a special evening out—symbolizing not just financial success, but the deeper satisfaction of earned enrichment.
Now at the helm of a growing team, Ray credits the majority of his company’s achievements to the philosophies and best practices he has absorbed through his extensive reading. He frequently references books that have strongly influenced his outlook, including Daniel Pink’s *Drive*, which explores motivation and purpose; Brené Brown’s *Dare to Lead*, which examines courage and empathy in leadership; and Brian Gottlieb’s *Beyond the Hammer*, which speaks to building lasting organizational value. These works, among others, have helped him frame his leadership approach, refine decision-making processes, and strengthen company culture. Looking ahead, Ray is eager to delve into Phil Gilbert’s forthcoming *Irresistible Change*, slated for release in late 2025, anticipating that it will offer fresh insights into innovation and adaptability.
In guiding his employees, Ray makes continuous learning a cornerstone of professional advancement. Within Geek Window Cleaning, promotions are not granted solely on tenure or performance metrics; part of the advancement process requires completing a curated set of books. In his view, the company’s purpose extends far beyond washing windows. As he explains it, “We’re not a window cleaning company; we’re a training facility that develops people.” His central mission is to ensure that every individual who joins his team emerges more capable, confident, and prepared for long-term success—no matter where their careers eventually lead.
For Ray, the foundation of any enduring success is self-education. He firmly believes that every business owner—regardless of their background, industry, or academic history—should cultivate a consistent habit of reading and reflection. Knowledge, after all, becomes the entrepreneur’s most reliable form of capital. Through deliberate learning, self‑discipline, and the humble pursuit of wisdom, Kyle Ray has demonstrated that the boundaries others set need not define one’s potential. Instead, they can serve as the spark that fuels a lifetime of growth.
Sourse: https://www.businessinsider.com/successful-entrepreneur-shares-his-hack-for-finishing-business-leadership-books-2025-10
