Five Weeks, 41 Mentors, 323 Sessions: Inside Tsai CITY’s Most Scalable and Data-Driven Thematic Mentorship Series Yet

This fall, Tsai CITY wrapped its most expansive thematic mentoring cycle to date. A five-week stretch that connected 41 mentors with 46 student teams across the Launch Pad and Accelerator programs. What began as a two-week pilot focused on getting students quick, tactical support, has now evolved into a foundational part of the venture development ecosystem, offering deeper access, richer conversations, and a truly scalable model for expert guidance. 

And this year’s numbers weren’t just strong, they represented a major leap forward powered by a well-designed technological architecture that can unlock mentorship support at scale. 

Over the five-week period, mentors offered 323 available sessions, averaging 21 per day across the 15 afternoons. Sessions were held three days per week, and students booked 116 meetings, demonstrating strong engagement, thoughtful preparation, and genuine excitement from both the mentors and teams. 

More Themes, More Expertise, More Possibility    

A major driver of this year’s success was an expanded slate of themes. Students could book time with mentors across 13 areas, reflecting the varied challenges and opportunities young innovators face, including: legal, operations, marketing & sales, digital strategy, fundraising, climate, education, healthcare, consumer products, intellectual property, nonprofits & social entrepreneurship, design thinking, and research-to-market. 

This breadth allowed teams to seek guidance on hyper-specific, real-time questions—from navigating regulatory hurdles to refining a go-to-market strategy to exploring ways to commercialize research. 

One mentor reflected on the energy students brought to their sessions:  

“[Our] meeting went well over time because the team was so enthusiastic and curious,” they shared. “I sent her follow-up information after, and she responded the same day.”

Students echoed similar enthusiasm. One team shared: 

“My mentor provided great insights into my business’ rebrand. I am grateful to have had the opportunity to connect with him.”

Another student noted how seamless the experience felt: 

“Easy process to sign up and book time. Highly recommend. I like that there is a list of mentors with their LinkedIn profiles—very helpful as I prepared.”

And this year’s roster included no shortage of deeply creditable experts. Students received guidance from leaders such as Diya Sagar, Chief Financial Officer at AWA Studios and a seasoned strategist in media and finance; John Choi, Managing Partner at Arbor Street Partners and a veteran of analytics, acquisitions, and global technology strategy; and Joshua Slavitt, a nationally recognized patent attorney and founder of Slavitt IP Law.Their combined experience shaped conversations across, fundraising, technology, intellectual property, and venture development. 

That level of expertise, paired with student curiosity, powered this year’s momentum. 

Designing Mentorship Around Real Student Needs

This year’s thematic mentorship worked because it was built around how students actually grow. The five-week format gave teams more flexibility, more access, and more opportunities for meaningful conversations at the right moments in their venture journey. 

“This model works because students lead their own learning journey,” says Victor Padilla-Taylor, Director, Mentor, Advisor, and Partner Network at Tsai CITY. “Our systems ensure that mentors have everything they need to offer high-value support, and students come in prepared, confident, and ready to act.”

Building on that, Victor highlighted how technology amplified the experience: 

“As part of the effort, we used an artificial intelligence tool to summarize the work of student founders, giving mentors a fast, accurate picture of each venture before meetings. The same tool helped students prepare by generating relevant mentor bios, context, and suggested ‘power questions’ that elevated the quality of their conversations.”

AI tools, thoughtful logistics, and a streamlined backend created an environment where students and mentors could dive deeper, faster, with both sides entering the conversations informed and aligned. 

In her role as Network Curator, Sabrina Layton (YC ’26) strengthened the system even further by coordinating logistics and capturing data in real time. She emphasized the importance of fast, lightweight feedback: 

“One of the most important things we did this fall was collect quick, 90-second feedback from both mentors and mentees after every session. It gave us real-time insight into what was working. Airtable enabled almost all of it — the automations, the routing, the reminders. Technology made the whole feedback system effortless, and that’s what allowed our network to keep improving week after week.”

This rapid feedback loop ensured every week of the cycle was stronger than the last. 

The fall cycle was further powered by Tsai CITY’s expanding mentor ecosystem, which surpassed 700 mentors; a major milestone that reflects the depth of alumni and industry engagement. Today, thematic mentorship stands as one of the clearest expressions of that network—a system that delivers focused, high-value expertise when students need it most.  

Where We Go From Here

This fall confirmed that thematic mentorship is more than a resource, it’s a growth engine. It accelerates learning, deepens mentor relationships, and strengthens Tsai CITY’s entrepreneurship and innovation community. 

Looking ahead, Tsai CITY will continue refining the mentorship experience, expanding thematic areas, and scaling access while keeping sessions focused, personal, and high-impact. 

Because the right guidance at the right moment can change everything, and this fall students had more than 323 chances to spark that shift.