YC Root Access

This Startup Is Automating America's Biggest Hospitals

In this episode of Founder Firesides, YC General Partner Aaron Epstein sat down with Kesava Kirupa Dinakaran, the Founder of Luminai (S20), which just raised a $38M Series B. Luminai is the AI transformation partner for health systems, automating the manual operational workflows for hospitals like Cleveland Clinic that still run on faxes and paper. Apply to Y Combinator: https://www.ycombinator.com/apply Work at a startup: https://www.ycombinator.com/jobs

AEAaron EpsteinhostKDKesava Kirupa Dinakaranguest

Apr 9, 2026·32m·Watch on YouTube ↗

📖 CHAPTERS

1. 1

   Luminai’s mission: AI transformation for hospital operations

   Keshav explains Luminai’s role as an “AI transformation partner” for large US health systems, shifting operational workflows from people and paper to software. The goal is to reduce administrative waste and help patients receive care faster.

2. 2

   Case study: Cleveland Clinic fax triage → structured data + routing

   A concrete example shows how critical referrals still arrive by fax, forcing staff to manually sort and route them. Luminai sits in front of the fax inbox, classifies urgency, extracts data, matches it in the EHR, and routes to the correct department to kick off scheduling.

3. 3

   Platform approach: unstructured-to-structured data + a workflow/agent layer

   Beyond a single workflow, Luminai positions itself as a data transformation layer plus a workflow engine to deploy specialized agents. Keshav frames the prize as tackling the ~30% of healthcare spend tied to administrative waste—over a trillion dollars.

4. 4

   Growing up in India: not academically strong, finding identity through Rubik’s Cubes

   Keshav describes feeling separated in a highly academic environment and discovering Rubik’s Cubes as an alternative meritocratic arena. He becomes intensely dedicated, practicing for years and rising to elite competitive levels.

5. 5

   Why Rubik’s Cubes were addictive: meritocracy, feedback loops, and measurable progress

   Two drivers kept him going: the community rewarded skill regardless of age/status, and the competition provided extremely measurable goals. The constant feedback cycle made improvement tangible and motivating.

6. 6

   A bold plan to reach America: UWC, mission-driven travel, and first Silicon Valley exposure

   Wanting US college attention, he pursued an unusual feat: biking from Turkey to China with institutional support, aligned with his school’s peace mission (United World College). A foundation later brought him to Silicon Valley, where the environment matched his long-held aspirations.

7. 7

   Surviving at 19: using hackathons as a cashflow strategy

   Staying in the US meant solving basic survival needs, and hackathons offered prize money. Keshav details a systematic approach to winning by optimizing for what sponsors and organizers wanted, using frequent feedback loops during the event.

8. 8

   Getting into YC with the “wrong” idea: engineering documentation automation

   Keshav describes YC as a merit-based opportunity similar to competitive Rubik’s Cubes—less reliant on traditional credentials. They applied with an early documentation automation product idea, got in, then realized quickly it wasn’t strong and pivoted.

9. 9

   Methodical pivoting: choosing a mission + finding repeated operational pain

   Keshav argues B2B pivoting can be more science than art: start from a mission that sustains long-term motivation, then systematically interview customers to identify generalized pain. A serious family health event made healthcare feel personally meaningful, and manual hospital operations emerged as the recurring opportunity.

10. 10

    Enterprise sales at 20: selling a champion, not the institution

    Keshav explains that enterprise deals hinge on one forward-leaning internal champion rather than the abstract brand name of the organization. He focused on finding unusually ambitious leaders inside bureaucratic institutions and used personal narrative to build trust early, before product proof fully existed.

11. 11

    Warm-intro pipeline building: LinkedIn scraping, investor networks, and iterative escalation

    Rather than cold outbound, Luminai relied heavily on warm introductions, especially because major institutions require trust. Keshav describes building a repeatable system: scrape networks, match against target accounts, ask for specific intros, and start anywhere in the org then ladder up to the champion.

12. 12

    Repositioning and focus: from horizontal automation to healthcare-first wedges

    After reaching many customers and millions in revenue, Luminai shifted from a generalized automation platform to a sharper healthcare focus. Keshav notes that credibility drops when you claim to do everything; hospitals need clear, high-value starting use cases that prove impact quickly.

13. 13

    Founder advice: be far more ambitious and aggressive than you think is allowed

    Keshav’s advice to his 19-year-old self is to scale ambition dramatically—100–1,000x—because many perceived constraints aren’t real. He emphasizes integrity, but argues the playing field is increasingly level and the mission should be pursued with multi-decade intensity.

14. 14

    Closing moment: Rubik’s Cube demonstration and send-off

    The conversation ends with a playful Rubik’s Cube challenge and a brief wrap-up on Keshav’s journey. Aaron underscores the outlier behaviors that signaled founder potential, then they close with thanks.