Is Michael Gerber still, right? Absolutely!
In The E-Myth Revisited, Gerber challenged entrepreneurs to stop working in their business and start working on it. Decades later, that distinction still separates companies that scale from those that stall.
But today we have an advantage Gerber did not. Artificial Intelligence
AI, used properly, is not a shortcut. It is leverage. It helps leaders think better, make clearer, and design stronger systems.
Working ON your business means stepping back from daily firefighting to clarify vision, debate strategy, and engineering processes. It is the difference between reacting and designing. I often think about the workflow scene that I absolutely LOVE in The Founder, where the McDonald’s brothers mapped their kitchen on a tennis court to perfect speed and efficiency.
They obsessed over systems before scale.
Today, AI allows us to do that level of thinking faster and deeper.
You can use AI to map workflows and identify bottlenecks. You can analyze customer feedback at scale. You can model pricing strategies, forecast cash flow, simulate capital raise scenarios, and test operational improvements before committing resources. Instead of guessing, you can model. Instead of defending opinions, you can interrogate data.
But let’s be clear. AI does not replace leadership thinking. It enhances it.
Delivering a WOW! customer and teammate experience never happens by accident. It is engineered. That means investing time in your people strategy, your pricing architecture, your execution rhythm, and your financial visibility. It means inspecting rather than expecting. AI can surface leading indicators you are missing. It can help you identify your “Moneyball” metric. It can show where the margin is quietly eroding. It can even flag retention risks before they become exits.
One of the greatest risks to any entrepreneur is confirmation bias. “Our plan is great”, “This strategy will work”, “The market will respond”. How much time do we spend challenging our own assumptions? Foreshadowing failure? Questioning our answers.
AI can serve as your intellectual sparring partner. Ask it why your plan might fail. Ask what a skeptical investor would question. Ask what competitor’s move could hurt you most. If too many yes people surround you, AI becomes the respectful contrarian in the room. Productive conflict sharpens thinking. Ego free debate strengthens strategy.
This is where Gerber’s thinking intersects with Jim Collins. Collins taught us to get the right people on the bus. AI gives those right people better dashboards, clearer insights, and stronger decision support. It does not remove accountability. It increases it.
Working ON your business still requires intentional space. Block time for strategy. Revisit shelved initiatives. Reevaluate pricing. Digitally mystery shop your competition. Review your meeting rhythm. Examine your leading indicators. Question whether your business model needs a pivot. Assess how many teammates you would enthusiastically rehire. Ask where mediocrity is hiding in your systems.
As you block time to work ON your business, consider:
- Are we using AI to optimize our time planning?
- Is our meeting rhythm strategic or reactive?
- What initiatives should we re-model with better data? What was working that we stopped doing?
- Where are our largest unrealized opportunities?
- Is our pricing aligned with value delivered?
- Have we digitally mystery shopped competitors?
- Are we tracking enough leading indicators?
- Do we know our true “Moneyball” metric?
- How strong are our financial dashboards? Real time or need some dusting off?
- Are we modeling capital raise / cash flow scenarios before we need them?
- How many teammates would we enthusiastically rehire?
- Where are we tolerating mediocrity in systems?
- Are we building a learning organization or a busy one?
AI is not the strategy. It is the multiplier of disciplined strategy.
The entrepreneurs who win over the next decade will not be those who simply adopt AI tools. They will be those who use AI to think better, question harder, and design stronger systems.
Gerber was right. Work ON your business, a LOT! And now, you can use AI to elevate how you do it.