Lifestyle

Meet Pilot Barry Billcliff and His Pursuit of Multifaceted Growth and Adventure

Published

2 months ago

May 20, 2025

Michelle Langton

Photo courtesy of Barry Billcliff

By: Georgette Virgo

Imagine looking from the top of the Great Pyramid of Giza, appreciating the picturesque landscape, and pondering the secrets that lie within each pyramid. This is just one scenario that reflects the life of the licensed pilot and modern-day adventurer Barry Billcliff.

From navigating the skies as a pilot to starting epic expeditions and immersing himself in live music events, Billcliff’s journey is anything but ordinary. With all his daring feats and ventures, what drives him to scale ancient wonders and create in industries as vibrant as construction and music?

Billcliff’s Adventures on a Global Scale

Billcliff’s interest in adventure is reflected in his ambitious escapades. From climbing the top of the Great Pyramid of Giza and the majestic Eiffel Tower, encountering the Los Angeles Police Department (LAPD) after a Hollywood sign stunt, exploring India with his son using his motorcycle, visiting the Galapagos Islands, breaking into the Sydney Opera House, and as random as dressing as a gladiator, Billcliff is unstoppable in the level of thrilling experiences he wants.

When asked why he does this, Billcliff’s answer was straightforward: “I want to be different in ways people can’t imagine or can comprehend as possible. To achieve this, I know I must be fearless, and these adventures push me to be just like that and more.”

Still An Ordinary Man

Besides being adventurous, Billcliff maintains a daily routine emphasizing growth and continuous learning. On a typical day, he works in the construction industry, enhancing efficiency and sustainability in building practices and even utilizing artificial intelligence (AI) to streamline processes.

From construction, his afternoons are spent at the gym he co-owns, where he works out and engages with a community that shares his passion for health and wellness. At night, he becomes a music promoter, channeling his creativity to assist bands with production.

Billcliff also shares that he applies the lessons from his global stunts to his writing, creating stories that offer readers a glimpse into his memorable experiences. He mentions, “I want to show the world that one can live an extraordinary life while remaining relatable and dedicated to lifelong learning. Adventurers have a place in the everyday world.”

Now a licensed pilot after passing the recent Federal Aviation Administration (FAA) pilot exam, Billcliff is exploring his career in flying and is excited about how this can elevate his future trips.

Billcliff and the Realities of Life

Like any story, struggles and challenges lie on the flip side of Billcliff’s exhilarating adventures. Billcliff shares that not all his ventures unfold smoothly; they occasionally place him in precarious situations and even on the verge of death.

Beyond global escapades, Billcliff’s life has also been marked by legal controversies. In 2005, he made headlines after claiming to have discovered antique banknotes valued at $125,000 during a roofing job in Newbury, Massachusetts.

The discovery sparked media attention, leading to charges against Billcliff and three others: Timothy Crebase, Kevin Kozak, and Matt Ingham. However, the case collapsed twice due to a lack of probable cause, with prosecutors ultimately dismissing all charges. The currency was returned to Billcliff, but has never been sold or seen in the marketplace; its fate remains a mystery.

A separate legal storm brewed around Merrimack Valley Roofing, a company linked to Billcliff, which faced a $150,000 OSHA fine. Investigations later revealed the penalty stemmed from a retaliatory dispute between Billcliff and OSHA agent Brett Buzzle. Crucially, appeals proved Billcliff had no ownership stake in the company at the time, leading to the fine’s overturning. Notably, Billcliff has never been convicted of any felonies.

Instead of being swayed by these setbacks, Billcliff embraces them as opportunities for growth and uses them to gain fresh perspectives. His resilience shines through in how he transforms failures into comebacks, with lessons learned from each challenge informing his subsequent ventures. This pursuit of growth and success, combined with his fighting spirit, makes him an asset in every field.

Lifestyle

Why Derik Fay Is Becoming a Case Study in Long-Haul Entrepreneurship

Published

3 days ago

July 2, 2025

Michelle Langton

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.