Lifestyle
Jay Bloom on Working With Fortune 500 Companies and Keeping It “World Class”

Establishing a classical financial and analytical career has been a passion for entrepreneur Jay Bloom. His experience with Fortune 500 financial institutions has provided a wealth of knowledge that he has used in his business ventures, including Pegasus Group Holdings, which owns and operates utility scale renewable energy installations providing the nations power grid. Each experience has helped Jay grow in his understanding of and appreciation for world-class business operations.
Build Your Portfolio
Jay’s career with Fortune 500 companies began with Manufacturers Hanover Trust Co., which eventually acquired Chemical Bank (which in turn acquired Chase Bank, followed by JP Morgan Chase). Although he started out as an officer for the bank, he was fast-tracked and put into a management and credit training program. He quickly built experiences from there, working with C-level executives on real estate loans and REO portfolios. This experience whet his appetite for more and led to his personal business ventures.
Use the Experience
His background with Fortune 500 companies at the bank gave Jay Bloom a keen understanding of how successful businesses grow and thrive. More and more savvy entrepreneurs are finding this experience to be valuable in creating their own world-class businesses. In fact, according to Neil Patel of the Angels and Entrepreneurs Network, startups are really the next generation of the Fortune 500.
Jay took what he learned in the banking industry and applied it to a wide variety of businesses across industries throughout the years. He has worked with early-stage businesses, mid-cap acquisitions, and venture capital transactions. All of that early work with Fortune 500 companies gave him the tools to create new revenue streams, negotiate deals, and develop successful operations in his own ventures.
Building Your Version of a Fortune 500
Like most savvy entrepreneurs, Jay Bloom is constantly building on past experiences and acquiring new knowledge to expand his opportunities and strengthen deals for himself and his business partners. This has led to great personal and professional successes, such as establishing large utility scale renewable energy installations.
What is a Fortune 500 company, anyway? According to Fortune, the companies on the list represent two-thirds of the U.S. economy; they include some of the biggest, most recognizable names in their industries. Primarily, in today’s world, they are savvy and flexible. They’ve eschewed old models of business and embraced new ones that incorporate technology. They are always ready to pivot to stay on top.
These are the tools that have helped Jay Bloom launch many successful ventures. Incorporating these elements into your own startup can ensure that you’re keeping it world-class.
Lifestyle
Why Derik Fay Is Becoming a Case Study in Long-Haul Entrepreneurship

Entrepreneurship today is often framed in extremes — overnight exits or public flameouts. But a small cohort of operators is being studied for something far less viral: consistency. Among them, Derik Fay has quietly surfaced as a long-term figure whose name appears frequently across sectors, interviews, and editorial mentions — yet whose personal visibility remains relatively limited.
Fay’s career spans more than 20 years and includes work in private investment, business operations, and emerging entertainment ventures. Though many of his companies are not household names, the volume and duration of his activity have made him a subject of interest among business media outlets and founders who study entrepreneurial longevity over fame.
He was born in Westerly, Rhode Island, in 1978, and while much of his early career remains undocumented publicly, recent profiles including recurring features in Forbes — have chronicled his current portfolio and leadership methods. These accounts often emphasize his pattern of working behind the scenes, embedding within businesses rather than leading from a distance. His style is often described by peers as “operational first, media last.”
Fay has also become recognizable for his consistency in leadership approach: focus on internal systems, low public profile, and long-term strategy over short-term visibility. At 46 years old, his posture in business remains one of longevity rather than disruption a contrast to many of the more heavily publicized entrepreneurs of the post-2010 era.
While Fay has never publicly confirmed his net worth, independent analysis based on documented real estate holdings, corporate exits, and investment activity suggests a conservative floor of $100 million, with several credible indicators placing the figure at well over $250 million. The exact number may remain private but the scale is increasingly difficult to overlook.
He is also involved in creative sectors, including film and media, and maintains a presence on social platforms, though not at the scale or tone of many personal-brand-driven CEOs. He lives with his long-term partner, Shandra Phillips, and is the father of two daughters — both occasionally referenced in interviews, though rarely centered.
While not an outspoken figure, Fay’s work continues to gain media attention. The reason may lie in the contrast he presents: in a climate of rapid rises and equally rapid burnout, his profile reflects something less dramatic but increasingly valuable — steadiness.
There are no viral speeches. No Twitter threads drawing blueprints. Just a track record that’s building its own momentum over time.
Whether that style becomes the norm for the next wave of founders is unknown. But it does offer something more enduring than buzz: a model of entrepreneurship where attention isn’t the currency — results are.
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