Little things matter enormously in business. A remembered name, a thoughtful question, a moment taken to listen—these seemingly minor actions often yield outsized returns. Nobody exemplifies this better than Dr. Tony Jacob, whose remarkable career trajectory from optometrist to successful entrepreneur and investor offers valuable lessons on the cumulative power of small gestures.
“One thing I repeatedly do and recommend everyone else do is to always remember people’s names and something about them,” he shared. “I make a point to never say no to a conversation, no matter who it’s with. So many doors have opened for me just by being open to meeting new people and having those conversations, even if I didn’t know where they would lead.”
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Random Conversations Change Lives
Someone asks what you do for a living. A casual question at work leads to an unexpected opportunity. We encounter these moments constantly, yet rarely recognize their potential significance until much later.
Dr. Tony Jacob’s career path began with exactly such a random workplace interaction. While working at a men’s clothing store during his teenage years in Canada, he engaged a customer who had purchased multiple pairs of nearly identical pants.
“He came in one day and bought seven pants, and I was like, ‘Why do you need seven dress pants? And they’re all kind of the same colour,” he recalled on “The Lifestyle Investor” podcast. “He told me he was an optometrist and he worked really close by. He said, ‘You did such a great job with the sales and the process here. Why don’t you come on in one Saturday and check out what I do? I know you’re thinking about what you want to do in school.”
That simple conversation led to a shadowing opportunity, which sparked Tony’s interest in optometry and ultimately shaped his entire professional career. Had he remained silent about the unusual purchase or neglected to show genuine curiosity, his life might have taken an entirely different path.
Tony actively applies this lesson today, making time for conversations and connections others might dismiss. He recognizes that truly meaningful business relationships often emerge from unplanned interactions rather than formal networking events.
Names Remembered Build Bridges
Memory creates connection. When someone remembers specific details about you—particularly your name—it signals genuine interest and lays groundwork for deeper relationships.
Dr. Tony Jacob made this practice a cornerstone of his approach to business relationships. Rather than viewing name recognition as a party trick, he sees it as demonstrating authentic interest in others—a small but meaningful gesture that opens doors throughout his career. “I try to remember names and something about every person I talk to,” he noted.
Memory signals respect, acknowledging someone’s inherent value and individuality. When Tony remembers both names and personal details, he creates immediate rapport that differentiates him from others who remain fixated on their own agendas.
Though simple in concept, this practice becomes extraordinarily powerful when consistently applied across thousands of interactions over decades. The cumulative effect creates a network built on authentic connection rather than transactional relationships.
Flowers Deliver Unexpected Returns
Small expressions of appreciation often yield disproportionate returns. When asked about his best recent purchase under $100, Dr. Tony Jacob didn’t mention a productivity tool or business book. His answer revealed volumes about his approach to relationships.”Random flowers for my wife!” he replied.
This seemingly personal example actually contains profound business wisdom. Tony recognizes that expressing appreciation strengthens crucial relationships, whether personal or professional.
Small, unexpected gestures of gratitude create emotional connections that formal business arrangements cannot replicate. When someone feels genuinely appreciated, they become invested in your success on a deeper level.
While Tony’s example involves his personal relationship, the principle extends throughout his business philosophy. Leaders who recognize contributions, remember important details, and express authentic gratitude build teams willing to go the extra mile during challenging times.
Listening Creates Opportunities
Active listening might be the most underrated business skill. In a world where everyone wants to speak, those who truly listen hold tremendous advantage.
Dr. Tony Jacob attributes significant portions of his success to genuine curiosity and attentive listening, even with people outside his immediate professional circle.
“Despite my natural inclination towards introversion, I consistently engaged in professional and personal interactions. Over time, these intentional connections yielded remarkably positive outcomes. Many of my most significant relationships and professional networks originated from seemingly spontaneous conversations,” he shared.
His investment philosophy similarly prioritizes listening skills when evaluating founders. Rather than focusing exclusively on business models or market opportunities, Tony pays careful attention to how potential partners communicate.
“If I like the person, their idea, and I can explain it in a sentence, I would probably invest,” he explained.
Tony’s experience suggests that founders who listen well typically demonstrate better emotional intelligence, adaptability, and leadership capacity—crucial attributes for long-term business success that financial projections alone cannot predict.
Good listeners collect perspectives others miss. While extroverted personalities might dominate conversations, introverted listeners like Tony often gather critical insights that help them make better decisions and identify opportunities others overlook.
The rewards of active listening extend beyond specific information gathered. People naturally gravitate toward those who make them feel heard and understood, creating a gravitational pull that attracts opportunities throughout a career.
Dr. Tony Jacob’s success demonstrates how seemingly minor behaviors—remembering names, asking thoughtful questions, expressing appreciation, and actively listening—compound over time into significant business advantages. These gestures cost nothing yet potentially yield enormous returns through stronger relationships, better information gathering, and unexpected opportunities.
Rather than dismissing these practices as “soft skills” secondary to technical expertise, Tony’s experience suggests they might actually be the foundational elements upon which lasting business success is built.
