Why My previous Startups Failed & What I Learned | Anubhav Jain (Rupifi)

"The good thing about starting for the fourth time is that you know what things you should not be doing."

This powerful insight from Anubhav Jain captures the essence of his journey. Unlike first-time founders focused on what to do, this serial entrepreneur has built a formidable "negative knowledge" playbook, using lessons from past failures to de-risk his current venture and scale faster.

Anubhav Jain is the Co-Founder & CEO of Rupifi, a B2B fintech platform radically changing how small businesses access credit. A serial entrepreneur and a credit risk expert from IIM Indore, Anubhav honed his skills for a decade at American Express. His previous lending startup, Qbera, was acquired after building a loan book of over ₹250 Crores. At Rupifi, he is on a mission to empower India's underserved SMEs, having already disbursed over ₹5,000 Crores in credit to more than 150,000 businesses across 500+ cities, backed by global investors like Tiger Global and Bessemer Venture Partners.

Key Insights from the Conversation

• The "Anchor-Led" Growth Model: Rupifi's genius lies in its B2B2C strategy, partnering with large marketplaces ("anchors") like Flipkart Wholesale and Zomato's Hyperpure to acquire SMEs at near-zero cost.
• Underwriting the "Un-bankable": Rupifi uses real-time transaction data from its marketplace partners to underwrite businesses, allowing it to provide credit to the 45% of its customers who had no prior formal credit history.
• The Outsourced-Tech Trap: Anubhav shares a critical lesson from his previous startup, Qbera, which faced a forced acquisition because its core technology was outsourced to a partner on an equity basis, crippling its ability to scale and raise funds.
• Collections as a Core Competency: To solve for the long-tail SME, building a powerful, multi-channel collections capability from day one is non-negotiable. At Rupifi, nearly half the team is dedicated to collections.
• The Power of Subvention: Rupifi's "Buy Now, Pay Later" product is typically free for the small retailer. The cost is borne by the marketplace (a "subvention"), which in turn sees significant growth in sales and customer stickiness.

Chapters

(00:00) The Biggest Lesson from a 4-Time Founder

(01:36) Building Risk Fundamentals During the 2008 Financial Crisis

(02:37) My First Startup Failure: What I Learned from Building an EdTech (05:25) The Second Venture: Building Consumer Lending Platform Qbera

(11:15) The Operational Hack for 24-Hour High-Ticket Loan Disbursal

(17:41) Why We Were Acquired: The Critical Mistake of Outsourcing Tech

(24:02) How 500 LinkedIn Messages Helped Me Find My Co-Founders

(28:14) The Rupifi Thesis: Solving the Real Credit Gap for Indian SMEs

(33:41) The Anchor-Led Model: How We Partner with Flipkart, Zomato & Others

(37:32) The Science of Underwriting SMEs with Zero Credit History

(49:43) Our Secret Weapon: Why Half Our Team Works in Collections

(55:31) How Rupifi Makes Money with a 0% Cost Product for Retailers

(01:04:46) The Key Challenges to Scaling B2B Embedded Finance in India

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