Dr. Connor Robertson on Why Some Entrepreneurs Are Using AI Wrong, and What to Do Instead

The most common way business owners use artificial intelligence is also, according to Dr. Connor Robertson, the least powerful one. A person opens a chat window, asks a question, reads the answer, and closes the tab. In Robertson’s view, that is not leverage. It is a slightly faster version of a web search. Real leverage, he argues, means AI is doing productive work inside a business while its owner is doing something else entirely.

Robertson, an entrepreneur and strategic advisor based in Pittsburgh, has built much of his recent thinking around this distinction. The problem with the search-engine approach to AI, as he describes it, is that the business owner remains the bottleneck at every step. They have to initiate the conversation, write the prompt, read the output, and then act on it manually. Nothing is running without them. The tool may be doing more than it once could, but the process still runs through the owner every single time, which means it has not actually reduced their workload. It has only made each individual step faster.

True leverage, in Robertson’s framing, looks different. It means AI is running without someone having to start it each time. He points to examples such as a system that monitors an inbox and flags high-priority messages on its own, one that drafts follow-up emails and queues them for a quick review rather than a full rewrite, or one that produces a weekly report and posts it to a team channel before the owner is even awake. The defining feature, in his view, is that the system is built once and then keeps producing, rather than requiring a fresh request every time.

To explain how far most businesses are from that point, Robertson describes what he calls three stages ofAI adoption. Stage one is manual query and response, the back-and forth chat window most entrepreneurs still rely on. Stage two involves templated prompts and saved workflows that cut down on repetition, letting someone reuse a strong prompt rather than write a new one from scratch each time. Stage three is fully embedded automation, where AI operates as a background process rather than a tool someone consciously opens. According to Robertson, almost all of the compounding value in AI sits in that third stage, yet most business owners never reach it, because stage two already feels like meaningful progress and the effort required to go further can seem hard to justify.

Making that shift, in his account, follows a fairly specific sequence. He suggests starting by identifying the three tasks that consume the most predictable, recurring time in a given week. From there, the next step is documenting exactly how each task is currently done, step by step, since a process cannot be automated if no one has actually written down what it involves. Once that is mapped out, Robertson recommends building a prompt template or an automation trigger that starts the task on its own, without the owner initiating it manually each time. After deploying it, he stresses measuring the quality of what it produces and refining the system until it matches, or exceeds, what was being done by hand. Only then, in his framing, should someone move on to automating the next task.

Underlying all of this, Robertson argues, is a shift in mindset rather than simply a shift in tools. He describes the difference as architectural. Thinking ofAI as something to pick up whenever a need arises keeps a person locked into stage one, no matter how sophisticated their individual prompts become. Thinking of it instead as infrastructure, something designed once and relied on continuously, is what actually opens the door to stage three. One approach demands attention every time it is used. The other, once built, keeps running while its owner sleeps.

Robertson frames this as more than a productivity tip. In his view, the entrepreneurs who treat AI as infrastructure now, rather than as an occasional tool, are the ones positioning themselves for the biggest operational advantage over the next few years. The gap between the two approaches, he suggests, is not really about who has access to betterAI models. Most people are working with similar tools. The gap is about who has taken the

time to build systems that run without them, and who is still, every day, sitting down to start the conversation from scratch.

About the Author

Dr. Connor Robertson is an entrepreneur, author, and strategic advisor based in Pittsburgh. He is the founder of Elixir Consulting Group and host of The Prospecting Show. More about his work is available at drconnorrobertson.com.

William Brown and the Founder’s Shift From Teacher to Designer of the Experience

In the beginning, the founder of an independent education program usually does everything. They teach the lessons, answer every question, handle the logistics, and hold the entire experience together through personal effort. William Brown’s work examines what happens next, when a program grows beyond what one person can sustain through presence alone, and the founder’s role has to change.

That change is significant. Early on, the founder is the experience. Their energy and involvement are what make the program work, and learners often join precisely because of who they are. But personal effort does not scale indefinitely. As more learners arrive, the founder cannot personally guide each one, and a program that still depends entirely on them begins to show strain in consistency and quality.

Brown’s perspective is that the founder must evolve from being the sole deliverer of value into being the designer of the environment in which value is delivered. This is a meaningful shift in identity as much as in function. Instead of personally carrying every learner through the material, the founder becomes responsible for building the structure, the curriculum, the support systems, the standards, that allows the experience to work well even when they are not directly involved in every moment.

This does not mean the founder disappears. William Brown’s work is clear that founder expertise remains central, often the very reason the program has credibility. The shift is about where that expertise is applied. Rather than spending all of it on direct delivery, the founder channels it into designing how the program teaches, defining the standards that protect quality, and clarifying the philosophy that gives the experience coherence. The founder’s knowledge becomes embedded in the structure rather than dependent on their constant presence.

The shift can be uncomfortable. Many founders take pride in their personal involvement, and stepping back from being the answer to every question can feel like a loss. There may be worry that the experience will become less personal or that quality will slip without their direct touch. Brown’s framing addresses this by reframing the goal. The point is not to remove the founder’s standards but to make those standards repeatable by others, so the experience reflects the founder’s care even when they are not in the room.

For learners, this evolution is largely invisible but deeply felt. They may never see the internal structure the founder has built. What they experience is a program that runs smoothly, responds reliably, and maintains a consistent quality regardless of how busy the founder happens to be on a given day. That reliability is the product of the founder having made the shift from teacher to designer.

Brown’s work also observes that this transition often reveals which founders were truly committed to their learners and which were attached mainly to the spotlight. Designing the environment is less visible and less personally flattering than being the star of every session. It means accepting that the program’s success will increasingly be credited to systems rather than to the founder’s individual brilliance. Founders who make that shift gracefully tend to be the ones whose primary motivation was always the learner’s progress rather than their own prominence. William Brown’s framing suggests that the willingness to step back, to let structure carry what charisma once carried, is itself a sign of a founder’s priorities. The ones who cling to being indispensable often do so for reasons that have more to do with ego than with what actually serves the people they teach, and learners ultimately feel the difference.

William Brown’s work positions this transition as one of the defining moments in the maturation of an independent education program. The programs that make it tend to grow more sustainable and more trustworthy, because they no longer rest on the fragile foundation of one person’s constant availability. The founder’s role becomes that of an architect, building an environment where learning happens reliably, which is ultimately a more durable contribution than being the person who must personally hold everything together.