Small talk — yea or nay?
Some entrepreneurs may wave off casual chitchat as not worthy of their time — but not so doctor, entrepreneur, CEO, investor, and adviser Dr. Tony Jacob.
He is a champion of deliberate choices, unexpected encounters, and the quiet power of open dialogue. But behind his impressive journey lies a simple, often overlooked truth: Some of the most impactful decisions in life and business emerge from conversations that at first glance seem minor or inconsequential.
Interactions with mentors, colleagues, friends, and strangers have steered him toward critical realizations, partnerships, and decisions that reshaped the trajectory of his professional and personal life.
“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.
“It’s not about networking for the sake of it — it’s about genuinely getting to know people. I wish I had been better at this when I was younger.”
What’s interesting is that these conversations for entrepreneurs weren’t always sought out. Some were chance encounters, others were direct invitations, and yet all seemed to follow a common thread: curiosity, openness, and a willingness to listen.
Finding Purpose in a Chance Conversation
His first pivotal conversation came before his career had even begun. While working in a men’s clothing store as a teenager in Canada, he struck up a seemingly casual conversation with a customer who had just purchased seven identical pairs of pants. The unusual nature of the purchase prompted Tony Jacob to ask, “What do you do for a living?” The answer? Doctor.
Tony recalled the encounter for “The Lifestyle Investor” podcast. “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.’
“One thing led to another, and I got to visit his clinic and started shadowing on Saturdays, and I just fell in love. I watched how much fun he had with his patients and really seeing the tangible result, which combined not only the happiness that he’d bring to patients once they got their prescriptions fixed, but it made him really happy. And I think his patients saw that on his face. And so that was really the inspiration that drove me.”
That single conversation and the experience it led to set Tony on the path to becoming a doctor, and years later, when he opened his first clinic in Lockhart, Texas, he would rely on that same willingness to ask questions, engage with others, and remain open to the possibilities embedded in each conversation.
“I really try not to turn down conversations or meetings,” he explained. “You never know where it leads, and you never know who you can help.”
The Evolution of a Conversation
Initially a clinician, Dr. Tony Jacob quickly realized that running a practice involved more than providing medical care, a realization shaped by his early experience at a private clinic where he observed the entrepreneurial acumen of its owners — a husband-and-wife team who transformed their business through relocation and ingenuity. Watching the owners balance their roles as both doctors and business builders sparked a pivotal realization for Tony, inspiring his transition from practicing medicine to embracing entrepreneurship.
He was inspired to open his practice in 2010, but this came with fraught hardships, as transitioning from doctor to entrepreneur required Tony Jacob to take on roles that initially felt unfamiliar.
Cash flow management, hiring the right team, negotiating with vendors — these tasks aren’t part of medical training, but Tony negotiated these hurdles by asking questions and engaging in conversations with other business owners, advisers, and colleagues who had been there before.
These interactions shaped his understanding of scaling and systematizing his practice. And it was through these conversations for entrepreneurs that he adopted frameworks and tools that allowed his business to thrive.
Eventually, his single clinic grew into a group of 11 practices across Texas, dominating multiple markets. But the growth wasn’t linear — it was a result of iterating on mistakes, learning, and listening.
“The first few years were really about trial and error,” he recalled. “But I found that every problem I encountered, someone had already solved it. All I had to do was seek them out and have the right conversations.”
Conversations That Build Teams
In scaling his business, Dr. Tony Jacob learned that its true value lies in the talent and dedication of its people. Managing doctors, support staff, and leadership teams across multiple locations requires a deep understanding of both human behavior and organizational needs.
Such demands led him to unearth the Culture Index, a personality-assessment tool that helped him align the right people with the right roles. Implementing this allowed him to identify strengths, communication styles, and behavioral patterns that allowed his employees to thrive.
“You can’t manage people effectively if you don’t understand them,” he noted. “Once I had data to support important conversations, we could have much more productive, honest discussions about performance, goals, and challenges.”
A Conversation About What’s Next
The decision to sell a business is among the most difficult for many entrepreneurs — and it often begins with a conversation. In the case of Dr. Tony Jacob, this dialogue was both internal and external: What did he want next? What opportunities would selling create for him and his family? And, critically, who would be the right partner to continue the legacy he had built?
When a strategic buyer approached him with an offer, the discussion unfolded quickly. He described the process as intense but rewarding. The values and vision of the acquiring company aligned closely with Tony’s, and their team brought the kind of professionalism and understanding that made the deal possible. After years of conversations that had shaped his business — with mentors, peers, employees, and customers — this final conversation for entrepreneurs marked the culmination of Tony’s journey as an entrepreneur.
It was also the beginning of a new chapter. Selling the business gave Dr. Tony Jacob not only financial freedom, but also the flexibility to explore new ideas, projects, and investments. Having achieved what he refers to as “100% passive income,” he now spends his time reflecting, investing, and mentoring others who are on their own entrepreneurial paths.
