Entrepreneurship as a living process
By Naman Gandhi ’25 MBA
Our Levy Inspiration Trek offered more than a window into cutting-edge AI ventures. It provided a human perspective on what it takes to build amid uncertainty, to balance conviction with adaptability and to design technology that creates real impact. From Chicago’s entrepreneurial ecosystem — at Built In Chicago, 2389.ai and Lightspeed — to the innovation hubs of San Francisco and Silicon Valley — including NVIDIA, OpenAI and IDEO — we encountered founder journeys spanning early experimentation to scale, investment and acquisition.
Through deep conversations with operators and investors across venture creation, go-to-market innovation, venture capital and mergers and acquisitions, we explored entrepreneurship as a living, evolving process rather than a fixed playbook. Here, I share four of the powerful themes that emerged across industries and stages throughout the immersive learning experience in Chicago and San Francisco.
1. Navigating uncertainty as the norm
Founders consistently described entrepreneurship not as a linear climb, but as a continuous process of learning, adjusting and making decisions without complete information. What stood out most was how openly they spoke about setbacks and uncertainty as essential parts of growth.
The trek reframed uncertainty not as something to eliminate, but as the environment in which real innovation happens.
2. Action as the engine for learning
Across sessions, founders and operators emphasized the need to move quickly from idea to execution, using real-world feedback to shape direction. Momentum, we learned, often comes from experimentation rather than a perfect strategy.
This mindset came alive in Mert Iseri’s energetic walkthrough of how 248.AI, a startup he helped create and now serves as CEO, is building go-to-market agents to reshape sales workflows, showing how rapid experimentation and close customer feedback fuel real progress.
3. Human-centered design as the differentiator in AI
While we explored some of the world’s most advanced AI infrastructure and platforms, conversations repeatedly returned to the role of people in shaping great products. As AI becomes more accessible, differentiation is increasingly rooted in creativity, empathy and a deep understanding of user experience.
IDEO, a global design and innovation company, highlighted how originality is emerging as a true competitive advantage. Take these generative AI tools/agents, where with a few prompts, you get a good average answer based on the large language model’s (LLM) basic training knowledge. To go from “good” to “great,” you add your own “taste” and design thinking — this is the true moat, and that concept of “return to deviance” will be the long-term differentiator of any AI company as well.
4. Rethinking how ventures are built
Several discussions challenged traditional assumptions about early-stage companies. We saw how AI-first ventures are enabling lean, highly capable teams supported by automation/agentic workflows and adaptability over scale, turning AI into a force multiplier. It turns out that the ability to create a billion-dollar company with AI and a lean team — often termed "nano-unicorns” — is transitioning from theory to reality, with several companies achieving immense valuations with fewer than 50 employees. For example, Cursor (Anysphere) has scaled to a $100M annual recurring revenue with a team of less than 50.
What we carry forward
Beyond inspiration, the trek sparked real momentum. My classmates and I are more comfortable navigating ambiguity, more open to embracing an experimental mindset, and have a deeper focus on human-centered design. We also have a renewed commitment to trust in AI and have clear next steps on how to engage customers and refine ideas — we’re committed to continuous learning.
The trek didn’t just inspire ideas. It accelerated execution with many of us already putting into practice what we learned during the immersive trip.
A fellow classmate Gary Spagnoli ’27 Executive MBA, shared how he is channeling his learnings from the treks into his own start-up, Analytics Mate. Gary and team recently launched an AI agent as part of their Analytics Mate product, The Helm, layered on top of Google Analytics to accelerate SEO performance through automated insights in a span of a few days. Gary shared one of his biggest takeaways from the immersive learning trip: “Speed over perfection, and validating ideas through real user feedback rather than abstract planning really stayed with me from the trek.”
Many of us began building and testing in ways we hadn’t before. Our Adjunct Lecturer Troy Henikoff couldn’t resist either. He built a fully functioning investment-tracking application using modern AI development tools in a fraction of the time that traditional development would require, demonstrating the power of AI in accelerating impact in every field and career stage.
This immersive learning experience wasn’t just shaped by the remarkable founders who shared their journeys but also by the thoughtful guidance of Mark Achler, an adjunct lecturer of marketing, and Heinikoff, who continually challenged us to think deeper. Armed with new perspectives, a commitment to continuous learning, and the courage to act before everything feels certain, I’m excited about building bold ventures that challenge convention and shape what comes next.
Read next: The discipline of listening and designing AI products with a global perspective
The views and opinions expressed in this post are those of the author, and do not necessarily reflect the position of the Kellogg School of Management or Northwestern University.