This as-told-to narrative emerges from an in-depth conversation with Robert E. Williams, a forty-year-old venture capital board director and seasoned startup advisor based in Maryland. The account below has been refined and edited for both clarity and concision, ensuring that its essence remains focused on the insight and experience he shared.
Williams began his professional journey at AT&T, where he dedicated the first thirteen years of his career steadily climbing the ranks until he earned the position of assistant vice president. During that period, he followed a clearly structured corporate path and benefited from the stability and predictability that come with a large, established organization. Yet, even within that comfortable environment, a single introspective question disrupted his trajectory and changed the direction of his ambitions: If the financial comforts and the perceived safety of Big Tech were to disappear entirely, what kind of work would he truly want to pursue? That question became the catalyst for an extraordinary transformation in how he viewed his professional life and personal aspirations.
By 2021, emboldened by this internal dialogue and desiring greater autonomy over his career, Williams decided to leave AT&T and step away from the security of his title to invest in his own potential. He began taking deliberate, carefully conceived career risks—measured steps that balanced ambition with prudence. These choices eventually led him into the rapidly evolving domain of startups, culminating in his engagement with an artificial intelligence company and, later, his current role in venture capital, where he advises early-stage founders whose visions he deeply believes in.
Williams describes the startup environment as invigorating, a complete departure from the steadiness and bureaucracy that characterize life in Big Tech. To illustrate, he likens the two worlds through an apt metaphor: while Big Tech resembles a luxurious yacht—steady, slow to change, and equipped with every safety measure—startups operate more like speedboats, nimble and unpredictable, darting through waves of uncertainty in pursuit of opportunity.
Reflecting on his origins, Williams recalls 2007, when he entered AT&T immediately after completing his undergraduate studies. He began as an account executive, surrounded by a corporate ecosystem that fostered employee development and responsibility from the outset. The professional culture supported his growth through mentorship, camaraderie, and a supportive network that helped him quickly develop leadership capabilities. For a young professional in his twenties, the financial security and well-defined progression paths were substantial motivators.
Over the following decade, Williams advanced from sales manager to director, ultimately achieving the esteemed role of assistant vice president by 2018. This role came with great responsibility and the satisfaction of measurable progress, but it was also governed by structure—composed of weekly meetings, methodical quarterly reviews, and a uniform rhythm that rarely deviated from the established corporate playbook. Each day was predictable, each month carefully mapped out by organizational objectives.
However, the global pandemic brought about an unanticipated pause, a space for self-reflection that made him reconsider what truly mattered. During this quieter period, he assessed his priorities beyond mere stability and financial security. He still valued the meaningful relationships forged at AT&T and the experience of leading large, capable teams. Yet, his curiosity turned toward the technological areas driving the next wave of growth—cloud computing, artificial intelligence, and the nascent stages of machine learning.
Although he wasn’t immediately prepared to abandon the relative safety of the corporate environment for a startup, Williams recognized the need to transition into a company that embodied innovation and disruption. Determined to bridge his experience with emerging technology, he left AT&T to join Amazon Web Services as a sales leader. This move, though risky, represented a carefully calculated experiment—an opportunity to test his adaptability in a faster-paced, innovation-driven organization.
After gaining a deeper understanding of how a major leader in innovation operated, Williams took yet another step into more entrepreneurial territory, joining a startup-oriented division within Palo Alto Networks. The experience refined his appetite for risk and further solidified his readiness to fully immerse himself in the volatile but exhilarating startup world.
In 2023, he made that leap, joining an artificial intelligence and quantum technology startup as head of global channels—a role that later expanded to head of revenue and partnerships. The position was dynamic and global in scope, requiring him to travel frequently to forge relationships and build international partnerships. His daily schedule, often lasting from early morning to evening, was consumed by team-building efforts, client engagements, and negotiations. The scope of responsibility was far broader than anything he had encountered in Big Tech, yet it energized him. Unlike the incremental progress of a large corporation, here he could see results almost immediately—new customers acquired, partnerships formed, media attention earned—all serving as tangible affirmations of his efforts.
That said, startup life was inherently unpredictable. Williams often found himself juggling diverse, high-stakes responsibilities—drafting responses to urgent RFPs one moment and presenting to a major venture capital fund the next. The financial structure, too, differed drastically. Startups typically offer a high-risk, high-reward tradeoff: employees often exchange guaranteed corporate income for the potential of equity-based upside. Williams learned that such a commitment requires conviction—not only faith in the company’s vision but also a realistic alignment with one’s personal lifestyle and time horizon, often spanning three to five years until a possible exit or acquisition.
Eventually, as his career evolved, Williams transitioned towards venture capital to broaden his impact. In May, he stepped aside from his executive role at the AI startup and accepted an advisory position, which enabled him to become a board director for a VC fund and an advisor for multiple startups, including a fintech enterprise and a medical device company operating across Africa. This shift allowed him to maintain involvement in innovation while reclaiming valuable personal time—time once lost to the constant travel of startup leadership.
Freed from the relentless travel schedule, Williams now enjoys a greater balance between professional engagement and personal fulfillment. He spends more quality time with his family and has reconnected with friends he had not seen in years. With this regained balance, he has also intensified his mentorship and advisory work, guiding startup founders and students from historically underrepresented backgrounds. This commitment to mentorship has become an essential part of his legacy—a way to extend the opportunities he once received.
Williams concludes that perhaps the most important endeavor in any professional journey is discovering what one is truly, functionally good at. Startups may offer unparalleled opportunities for individual impact, allowing ambitious professionals to shape outcomes directly and, potentially, share in equity-based rewards. However, he is realistic about the risks: the majority of startups fail, and even Big Tech is no longer the bastion of long-term job security it once was, especially amid the transformative and disruptive rise of artificial intelligence.
For Williams, self-knowledge has been the linchpin of his success. His recognized strength lies in go-to-market business development and strategic partnerships—skills that have anchored him through transitions across vastly different environments. His advice is simple yet profound: when you identify and cultivate the specific functions where you excel, you become an invaluable asset, whether operating within the vast machinery of Big Tech or the fast-paced ecosystem of startups.
For those contemplating a major career transformation, his story serves as both an answer and an invitation—to ask yourself the hard questions, calculate the risks worth taking, and rediscover what it means to bet on yourself.
Sourse: https://www.businessinsider.com/quit-big-tech-for-startups-risk-was-worth-it-2025-11
