The Dark Side of Buy Now Pay Later
- Jun 2
- 2 min read
Episode 112: Sam Miller
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.
Show Notes:
00:00 Rock Bottom Beginnings
00:48 Podcast Intro
01:52 Born Entrepreneur
03:10 College Dropout Choice
04:12 What Kasheesh Does
06:28 Idea Spark Moment
07:59 Building MVP and Fundraising
08:47 Customer Use Cases Shift
10:13 Naming Kasheesh Story
10:38 Three Startups Lessons
13:11 Investors Blessing and Pressure
14:59 Hiring and Founder Responsibility
17:13 Timing the Market
18:12 Startup Grind and AI
23:10 Dropping Out Pressure
25:19 Dad and Entrepreneurship Gap
28:42 Fatherhood Perspective
31:16 Proving Dad Wrong
33:29 Forgiveness And Motivation
36:48 Lessons For Fathers
38:25 Operator Versus Investor
41:37 Reading Founders
43:06 Raising Money For Kasheesh
46:09 Founder Struggles And BNPL
49:57 Misinformation And AI
52:07 Economic Red Flags
58:13 Debt Delinquencies Spiral
01:00:12 AI Shopping And Replay
01:04:46 Who Uses Kasheesh
01:06:13 Points Splitting Use Cases
01:06:59 How Kasheesh Maximizes Rewards
01:09:10 Amex Perks Activation Problem
01:10:25 Gift Cards And Balances
01:12:29 Gray Hair Investor Story
01:16:27 Grandma And Founder Belief
01:19:15 Call Her Daddy Origins
01:23:42 Kasheesh Five Year Vision
01:25:49 Acquisition And Data Moat
01:27:55 Rapid Fire And Wrap Up
