EPISODE · May 9, 2026 · 23 MIN
How Kasheesh Is Changing The Way People Pay Online
from Legends N Leaders · host Ben Weiss
In this episode of LegendsNLeaders, we sit down with Sam Miller, CEO and co-founder of Kasheesh, the fintech platform allowing consumers to split purchases across multiple payment cards as an alternative to Buy Now Pay Later services.A four-time entrepreneur and investor, Sam shares his journey from college dropout to building companies focused on solving real consumer problems with transparency and purpose.We discuss:• The future of digital payments and fintech• How Kasheesh helps users avoid high lending fees• Consumer behavior and spending trends in today’s economy• Building and scaling startups in your 30s• Entrepreneurship, resilience, and product-market fit• What real-time transaction data says about the economyAt the time of recording, Kasheesh has organically grown to over 110,000 users and facilitated more than $72 million in transactions, helping consumers better manage payments, shared expenses, tuition, rent, and everyday purchases.Sam also shares insights on leadership, startup culture, building mission-driven companies, and why integrity matters more than ever in fintech.This episode is packed with insights on entrepreneurship, consumer finance, fintech, startups, economic trends, and the future of payments.#Fintech #Entrepreneurship #Startup #BusinessPodcast #ConsumerFinance #Payments #LegendsNLeaders
What this episode covers
In this episode of LegendsNLeaders, we sit down with Sam Miller, CEO and co-founder of Kasheesh, the fintech platform allowing consumers to split purchases across multiple payment cards as an alternative to Buy Now Pay Later services.A four-time entrepreneur and investor, Sam shares his journey from college dropout to building companies focused on solving real consumer problems with transparency and purpose.We discuss:• The future of digital payments and fintech• How Kasheesh helps users avoid high lending fees• Consumer behavior and spending trends in today’s economy• Building and scaling startups in your 30s• Entrepreneurship, resilience, and product-market fit• What real-time transaction data says about the economyAt the time of recording, Kasheesh has organically grown to over 110,000 users and facilitated more than $72 million in transactions, helping consumers better manage payments, shared expenses, tuition, rent, and everyday purchases.Sam also shares insights on leadership, startup culture, building mission-driven companies, and why integrity matters more than ever in fintech.This episode is packed with insights on entrepreneurship, consumer finance, fintech, startups, economic trends, and the future of payments.#Fintech #Entrepreneurship #Startup #BusinessPodcast #ConsumerFinance #Payments #LegendsNLeaders
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How Kasheesh Is Changing The Way People Pay Online
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