Charlestown Beginnings: The Man Who Solved Problems (1966–1990s)

In 1966, in the working-class neighborhood of Charlestown, Massachusetts, Bob Gillis built a reputation not through marketing, but through action. A natural problem solver, Bob had an uncanny ability to help small business owners, families, and individuals navigate complex decisions—whether it was negotiating a deal, restructuring finances, or mediating personal disputes.

He never saw himself as a consultant. He was simply “helping people out,” often scribbling notes and ideas in the margins of well-worn books. A voracious reader, Bob loved old detective novels and business strategy books alike. His makeshift office was a kitchen table, and his payment was often a handshake, a favor returned, or a round at the local pub.

It wasn’t until the late 1970s that his informal advisory services took on a more structured form, and by the 1990s, Gillis & Associates had become a respected but under-the-radar consulting firm, built on trust, instinct, and results.

The Next Generation: Expansion and Evolution (1990s–2023)

Bob’s son, Bryan Gillis, grew up watching his father operate, but he saw potential for something more. Unlike his father, Bryan pursued formal business education and honed a sharper, more structured approach to consulting. By the 2000s, he had expanded the business beyond Massachusetts, setting up offices in Florida and California, bringing in new clients and modernizing the company’s approach.

But even as the company grew, one thing never changed—Bob’s love for books and his self-deprecating humor about their financial success. For years, he had joked that if his business ever failed, he’d start a publishing house and call it “Fly By Night Publishing”—because, as he’d put it, “That’s what most people think of consultants anyway.”

A New Era: Rebranding as Fly By Night Publishing (2023–Present)

In 2023, following Bob’s passing, Bryan decided to rebrand the company in honor of his father’s wit and legacy. He moved the headquarters to San Francisco, a city known for reinvention, and officially changed Gillis & Associates to Fly By Night Publishing—a name that embodied both Bob’s humor and the firm’s reputation for unconventional, fast-moving solutions.

Of course, Fly By Night Publishing isn’t a traditional publishing house. Instead, it’s a boutique, high-impact consulting firm specializing in:

• Business Strategy & Leadership Development

• Crisis Management & Conflict Resolution

• Corporate Restructuring & Succession Planning

• Creative and Brand Consulting

While the firm’s look and approach have evolved, its core values—practical wisdom, straight-shooting advice, and problem-solving for real people—remain intact. The name may sound like a joke, but for clients, the results are anything but.

Bryan continues to honor Bob’s legacy, ensuring that every Fly By Night client gets the same level of commitment that his father once gave at a Charlestown kitchen table. In an industry filled with buzzwords and overcomplicated strategies, Fly By Night Publishing stands out by keeping things simple: know the people, understand the problem, and find the best path forward—fast.