Dr. Tony Jacob on Why Timing Makes or Breaks Business Sales

Picture yourself waiting years to sell your company, then suddenly closing a multimillion-dollar deal in mere weeks. That whirlwind scenario played out for Dr. Tony Jacob when he sold his optometry practice empire in 2021.

“We got the deal done in about 30 days. My head is probably still spinning from it, it happened so quickly,” Tony revealed during “The Lifestyle Investor” podcast.

Yet behind that rapid transaction stretched years of methodical preparation. Tony had quietly built operational systems, expanded to multiple locations, and monitored market trends—all while developing financial independence that allowed him to negotiate from strength rather than necessity.

Watch The Market Like A Hawk

Smart founders understand something crucial about selling: your business valuation depends less on internal metrics and more on external market conditions you cannot control.

Dr. Tony Jacob paid careful attention to acquisition temperatures during and after COVID-19 disruptions. While many owners panicked through shutdowns, he recognized these challenges would eventually make his resilient practice more attractive to buyers.

“During 2020, our business encountered multiple significant challenges. We endured literal and metaphorical storms, including a severe weather event in Texas that temporarily shut down our operations. A ransomware attack further complicated our landscape, presenting a complex series of obstacles that tested our organization’s resilience. Despite these formidable challenges, our team demonstrated remarkable adaptability and perseverance.” Dr. Tony Jacob explained. 

Medical practice acquisitions slowed dramatically during pandemic uncertainty, then accelerated as buyers hunted for proven operations that survived the chaos. Tony watched these patterns develop, noting which strategic acquirers had capital ready for deployment and which segments commanded premium multiples.

Paying attention to broader market conditions—including interest rates, private equity activity, and industry consolidation trends—enabled him to time his exit during an ideal seller’s market.

Systems That Run Without You

Many founders create accidental prison cells rather than sellable assets. They build businesses entirely dependent on their personal magic—their relationships, expertise, and daily firefighting.

Dr. Tony Jacob deliberately chose another path. Long before entertaining sale offers, he methodically replaced himself with scalable systems and capable leaders.

“I had successfully unlocked each business development stage, performing well in opening one office, then two. Yet the next critical challenge was understanding how to transition into a true CEO role and comprehending the fundamental responsibilities of executive leadership,” he shared.

Tony implemented Culture Index for talent optimization and the Entrepreneurial Operating System (EOS) for consistent operations across locations. These frameworks transformed his practice from a founder-dependent business into a systematic enterprise.

“We implemented this approach across our leadership team and throughout all office locations, which dramatically accelerated our organizational momentum. Once integrated, the strategy produced remarkable results. Our strategic planning—particularly our three-year and one-year roadmaps—began to crystallize rapidly, and organizational alignment became significantly more cohesive.” Dr. Tony Jacob said.

Sophisticated buyers pay premium prices for companies that demonstrate transferable value through documented processes, capable management teams, and predictable operations independent of the founder.

Mental Preparation Trumps Financial Readiness

Money occupies most conversations about business exits, yet psychological readiness determines satisfaction with the outcome far more reliably.

Dr. Tony Jacob prepared himself mentally and financially years before entertaining acquisition discussions. He strategically built passive income streams through real estate investments until reaching what he called “hundred percenter” status—generating enough passive cash flow to cover all personal expenses.

“Early in my entrepreneurial journey, I established a financial goal of generating sufficient passive income to fully cover my living expenses, ensuring economic independence regardless of my future professional trajectory,” he explained.

Financial independence granted him extraordinary negotiating leverage. Without pressure to sell, Tony could confidently walk away from suboptimal offers and wait for ideal terms.

“Although I was not actively seeking to sell initially, receiving an offer with substantial financial compensation was both flattering and validating. The transaction represented a meaningful acknowledgment of the value and effort invested in building the business,” he reflected. 

Founders lacking this preparation often experience post-sale regret regardless of the financial outcome, finding themselves wealthy yet purposeless after exiting businesses central to their identity.

Growth Acceleration Attracts Premium Buyers

Ordinary companies receive ordinary valuations. Exceptional growth trajectories, however, command extraordinary premiums and attract motivated strategic acquirers.

Dr. Tony Jacob dramatically accelerated his expansion pace during the years immediately preceding his sale—perfect timing to maximize valuation.

“Looking from 2017 to the year that we sold in 2021, we had actually 7x star revenue. So it didn’t take us that long. And I look back, we did it in about four years,” he noted.

Healthcare consolidation trends surged during this exact period as private equity platforms and strategic acquirers competed aggressively for scalable practices with proven expansion models. Tony’s growth surge perfectly matched what these buyers sought.

Attempting the same exit several years earlier, before demonstrating this remarkable growth trajectory across multiple locations, likely would have yielded significantly lower offers or struggled to attract premium buyers altogether.

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Josie
Joyce Patra is a veteran writer with 21 years of experience. She comes with multiple degrees in literature, computer applications, multimedia design, and management. She delves into a plethora of niches and offers expert guidance on finances, stock market, budgeting, marketing strategies, and such other domains. Josie has also authored books on management, productivity, and digital marketing strategies.

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