For many small business owners, ambition often shows up as a single idea: grow as fast as possible. But Yali Saar, CEO and Founder of Tailor Brands, challenges that instinct. “Going big is not a strategy,” he wrote recently, arguing that clarity matters more than scale.
That idea sets the stage for an upcoming webinar hosted by Tailor Brands, “How Smart Business Formation Leads to Better Exits,” taking place on Monday, January 5th, 2026, at 3 p.m. EST. Saar will be joined by Blake Hutchison, CEO of Flippa, for a conversation focused on how early business decisions shape long-term outcomes, especially for founders who want options later on.
Defining What You’re Actually Building
According to Saar, the most important decision founders make often comes before product, marketing, or growth. It is deciding what the business is being built for. Is it meant to provide job security? Is it something to carry a family name forward? Or is it being built with a future sale in mind?
Saar argues that once this decision is made, it becomes the goal. From there, founders can begin working backward to determine the structure, priorities, and trade-offs that make sense for that destination. Without that clarity, progress becomes difficult to measure, and strategy becomes reactive rather than intentional.
The Difference Experience Makes
Saar draws a clear line between first-time entrepreneurs and those who have built multiple companies. The distinction, he notes, lies in awareness. Serial entrepreneurs understand the toll building a business can take, and they approach the process with that reality in mind.
Some arrive at this understanding through deliberate planning, while others reach it only after running enough tests over time. In either case, the outcome is similar: experienced founders develop a clearer sense of direction earlier and are better equipped to recognize when they’ve drifted off course.
Why Working Backwards Matters
Reverse engineering a business plan is not presented as a shortcut. Saar acknowledges that the process may not be easy and may not unfold exactly as planned. But with a defined goal in place, founders gain a critical capability: the ability to measure progress and adjust when things don’t go as expected.
Without a goal, Saar suggests, everything is left to luck. With one, founders have a reference point to recalibrate rather than restart.
This idea forms a core theme of the upcoming webinar, particularly as it relates to building businesses that hold value beyond day-to-day operations.
A View from Both Sides of the Journey
Tailor Brands currently helps more than 2% of new U.S. business owners launch their companies, giving Saar a front-row seat to how businesses begin. Flippa, meanwhile, has supported over 100,000 online acquisitions globally, offering insight into what happens when founders decide to exit.
Together, Saar and Hutchison plan to explore how starting a business “the right way” can create advantages across multiple fronts, including one many founders overlook: building something that is attractive to buyers down the line.
An Invitation to Build with Clarity
The webinar is aimed at SMB founders who want to be more deliberate about where their efforts are leading. Rather than promoting a single outcome, the session focuses on helping entrepreneurs define their own goals and understand how that choice shapes everything that follows.
“How Smart Business Formation Leads to Better Exits” takes place on January 5th, 2026, at 3 p.m. EST, and offers founders a chance to step back from day-to-day execution and consider the long-term implications of how they are building.
In a crowded entrepreneurial landscape, Saar’s message is a measured one: success is not about size alone, but about direction, and direction starts with knowing what you’re building toward.