About this episode

Kyle Matthews interviews Sam Miller about the evolution of Kasheesh and the challenges of buy now pay later lending.

On the Matthews Mentality podcast, host Kyle Matthews interviews four-time founder and Kasheesh CEO Sam Miller, who dropped out of college, bootstrapped early companies, achieved three exits, and now leads a fintech platform that lets consumers split purchases across multiple cards with no loans, interest, or credit checks. Miller explains Kasheesh’s origin as a response to predatory buy-now-pay-later lending, its evolution from a browser extension to Apple Pay/Google Pay, and growth to 110,000+ users and $72M+ in transactions. They discuss fundraising challenges, differences between bootstrapping and venture-backed startups, lessons from working in VC, and how consumer usage shifted from discretionary spending to essentials like rent and utilities. The conversation also covers AI’s impact on work, economic warning signs, and Kasheesh roadmap features like Replay, group payments, and rent reporting to credit bureaus.

People in this episode

Host: Kyle Matthews

Guest: Sam Miller

Topics covered

• buy now pay later
• fintech
• entrepreneurship
• bootstrapping
• consumer spending
• AI impact
• fundraising

Keywords

• buy now pay later
• Kasheesh
• fintech
• entrepreneurship
• bootstrapping
• consumer spending
• AI
• fundraising

Mentioned in this episode

Organizations: Kasheesh, Apple Pay, Google Pay

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