25. The Anti-Slop Builder: What 25,000 Hours of AI Looks Like with Piyanka Jain

Piyanka Jain has been building AI models since 2002 - before "AI" was a buzzword. Today she's the CEO of AskEnola, an agentic AI platform that automates the entire CFO workflow: closing books, P&L reporting, MRR schedules, and investor reporting - all with high-fidelity output that doesn't hallucinate. In this episode, Piyanka talks about what 25,000 hours of building actually looks like, why she walked away from enterprise deals to chase mid-cap CFOs, and what "sophisticated in all the right ways" means when your go-to-market is still 100% scrappy hustle. Chapters: 00:00 - Sophisticated Where It Counts, Scrappy Everywhere Else 01:38 - Real AI at Scale: 7-Eleven ATMs and Kiva Donations 04:38 - Warrior Class to Business Class: Piyanka's Origin Story 07:45 - Transformation as the True Motivation 11:52 - What AskEnola Actually Does for CFOs 15:21 - 25,000 Hours, Multiple Pivots, One Winning Bet 20:15 - The SaaStr Slop Problem and the Trust Deficit 25:46 - When Do You Know It's Ready to Ship? 33:53 - Scrappy vs Sophisticated: The Rapid Fire Round 38:19 - Hustling Into the Right Rooms and Manifesting the Right Clients 44:24 - Productivity vs Presence: Slowing Down to Feel Worthy Connect with Piyanka Jain: https://www.linkedin.com/in/piyanka/ https://www.askenola.ai Connect with Jack Tompkins: https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineappleanalyst.ai/ https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng