In a business world driven by surface-level metrics and buzzwords, Derik Fay operates differently. A serial entrepreneur, investor, and strategic advisor, Fay has built a reputation as the man who sees opportunity where others see dead ends. With over 30 companies scaled and exited, and more than 40 active investments through his holding company, 3F Management, Fay is proof that true success lies in perception — not just performance.
At first glance, Fay’s story reads like a checklist of entrepreneurial milestones: early exit in fitness, diversified holdings across tech, real estate, fintech, and entertainment, and a client list that includes celebrities and rising startups alike. But beneath those bullet points is a unique philosophy — one built not just on numbers, but on narrative.
“Every business is telling you a story,” Fay once said in a private roundtable. “Most people don’t listen long enough to understand it — they’re too busy looking at the last quarter’s numbers. But I’m listening for the value hiding between the lines.”
That mindset recently came to life in an under-the-radar transaction involving a struggling logistics software company in the Midwest. The company had great tech, a loyal customer base, and a brilliant but burned-out founder — what it lacked was funding and direction. Fay didn’t walk in with a checkbook. Instead, he walked in with a plan.
He restructured the company’s pricing model, introduced a joint venture with one of his existing firms in the same vertical, and helped the founder negotiate a clean split from a toxic investor who had been draining the business. Within six months, the company was profitable. In twelve, it was acquired by a larger platform player. Fay never took operational control — just a strategic position, some sweat equity, and a cut of the upside. And most importantly, the founder got a second wind, a fair exit, and a sense of purpose back.
It’s not just one-off wins. Fay’s model scales. Through 3F Management, he actively supports dozens of companies with more than capital. His involvement spans marketing, operational infrastructure, mergers, and sometimes, just mindset. CEOs have described him as part investor, part therapist, part secret weapon.
Fay’s own rise began humbly, which may explain his deep connection to underdogs. Raised in Rhode Island, he launched his first major venture — Around the Clock Fitness — in his early twenties, building it into Florida’s largest independently owned fitness chain before a major exit in 2019. That deal alone would have set most entrepreneurs for life, but for Fay, it was just the beginning. Since then, he’s operated across sectors, accumulating a portfolio that’s both diverse and high-performing.
And yet, despite the accolades, Fay remains grounded. His online content — which reaches millions — focuses less on flexing wealth and more on sharing lessons. In one Instagram reel that recently went viral, he said, “The shortcut is doing the hard things. That’s the hack no one wants to hear.”
But don’t mistake humility for complacency. Fay’s calendar remains packed with deal flow, mentorship calls, board meetings, and high-level events where he continues to share stages with icons like Tony Robbins, Tim Grover, and industry titans. His focus, however, is always forward. “I’m addicted to unlocking potential,” he said in a recent podcast. “In people, in businesses, in moments.”
It’s that obsession — with what could be rather than just what is — that defines the “Dealmaker’s Mindset.” Not just finding undervalued assets or untapped markets, but lifting the lid on situations others have written off. And more often than not, turning them into gold.
Derik Fay doesn’t chase the spotlight, but his results speak loudly. He’s not just doing great — he’s building greatness, deal by deal, quietly shaping the future of business while staying true to his mission: find value, create impact, and never stop pushing boundaries.
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