An entrepreneur has taken AI personalization to the next level by building a custom GPT trained to think and advise like Steve Jobs, using the legendary Apple co-founder’s decision-making style as a model. Rather than relying on generic AI responses, this bespoke system channels Jobs-like intuition, focus on simplicity and product-first thinking — qualities the founder believes are crucial for high-stakes business decisions. By feeding the model curated texts, interviews and frameworks attributed to Jobs, the AI synthesises guidance in ways that echo the late innovator’s strategic mindset.

The idea isn’t to recreate Steve Jobs, but to capture patterns in his approach — prioritising clarity, customer experience and ruthless prioritisation. When faced with choices around product features, marketing strategy or growth trade-offs, the AI helps the founder explore both creative and analytical angles, making recommendations rooted in values rather than just data points alone. This experiment sits at the intersection of AI customization, leadership coaching and entrepreneurial intuition, showing how bespoke AI can augment human judgment without replacing it.

For many small and mid-sized founders who juggle multiple roles, such tools offer a second opinion that feels aligned with a defined philosophy or leader archetype, helping reduce cognitive load and accelerate decision loops. It also highlights a broader trend: as AI becomes more integrated into business workflows, leaders are seeking tailored assistants that reflect their values, frameworks and long-term visions, rather than one-size-fits-all models. This approach may redefine how founders think about strategy support, mentorship and AI’s role in fostering more intuitive, philosophy-driven decision-making.