A Last-Mile Problem for AI
Why AI Can't Replace Creative Entrepreneurial Intuition
The Last-Mile Problem: Why AI Can't Replace Entrepreneurial Intuition
AI is an extraordinarily powerful tool, but whether it is ultimately a good thing will depend on how humans use and deploy its amazing predictive capabilities. But there's a fundamental misunderstanding about what it can do for entrepreneurs that's becoming increasingly problematic as the hype cycle spins faster and faster.
This is another variation of the Last-Mile problem–the gap between algorithmic recommendations and human decision-making, along with their resulting real-world actions. This is a place where all the data analysis in the world meets messy human reality with the latter prevailing every time. But this, for entrepreneurs, is the modern equivalent of sailing out upon the oceans in search of the new El Dorado. Navigating these uncharted waters is their ideal operating environment, and where AI, despite its impressive capabilities, can contribute very little beyond a supporting role.
The Human Element Isn't Optional
Technologists and engineers, mathematicians in particular, revel in the claim that everything can be reduced to data and patterns. If that were true (which it self-evidently isn’t), then entrepreneurship would be easy. Just feed enough market research into an algorithm and wait for the perfect business plan to emerge. But clearly, that doesn’t work because it misses the human element in that most people are not rational.
Steve Jobs is never a good example, as he was such a one-off. But leaving that aside, he didn’t create Apple by running market simulations. He combined calligraphy, Eastern philosophy, and an obsessive attention to product design that no algorithm could have connected. The pattern recognition that happens in the entrepreneurial mind isn't just about correlations in datasets–it's about seeing connections the way that artists and creators are able to do.
The world is complex, dynamic, multidimensional. This a dilemma for the entrepreneur – how to transform multidimensional human insight into a saleable product–how to translate code, weights, and vectors into business reality.
Cultural Timing Isn't Algorithmic
AI can't feel, therefore it is unable to detect the subtle shifts in cultural dynamics that determine whether a business lives or dies. This isn't just about data – it's about sensing when society is ready for something new. Airbnb's co-founders sensed something changing in the cultural atmosphere–a shift in how people thought about trust, community, and authentic experiences that no dataset captured.
Peter Thiel got this right in his book Zero to One when he wrote: "The most valuable businesses of coming decades will be built by entrepreneurs who seek to empower people rather than try to make them obsolete.”
The irony here is that entrepreneurs often succeed precisely because they ignore what the data tells them and what everyone else believes. In the end, there is no substitute for trusting one’s own judgment.
Conviction Isn't Computational
This is perhaps the clearest divide between AI and the entrepreneurial mindset: the ability to maintain conviction in the face of contrary evidence. AI is fundamentally designed to optimise based on available information. But success requires persisting when all the data suggests you should quit.
Jeff Bezos focused on Amazon's expansion despite years of losses and Wall Street skepticism. This wasn't irrational–it was based on a deeper understanding of potential that transcends immediate metrics. True entrepreneurs, creators, and artists do not ignore reality; they simply perceive a deeper reality that others miss.
Customers Aren't Data Points
Artists and entrepreneurs are able to connect with human desires and needs that often go unarticulated. Real innovation doesn't just solve technical problems; it addresses emotional and social needs that people may not even realise they have.
The Partner, Not the Replacement
None of this means AI isn't valuable. It absolutely is. But there's a profound difference between a tool for thinking and a hyped up replacement for thinking. AI excels at scaling analysis, optimising processes, and enhancing decision-making – all crucial functions.
The future isn't AI replacement but AI partnership–combining algorithmic intelligence with the irreplaceable human qualities that define entrepreneurial genius. Most importantly, knowing when to trust the machine and when to trust your gut.
This is the heart of the last-mile problem–that final stretch where algorithms end and humanity begins. And despite all the advances in technology, crossing that last mile will remain a uniquely human journey and an absolute gift for entrepreneurs.