Interview with Charles Rosenblatt: The Javelin Thrower's Guide to Building a Fintech Career

Interview with Charles Rosenblatt: The Javelin Thrower's Guide to Building a Fintech Career

Host - Rory Holland - cstmr.com - Linkedin: CSTMR

Interviewed - Charles Rosenblatt - butterpayments.com - LinkedIn: Butter Payments

In This Episode

Charles Rosenblatt, CEO of Butter Payments, joins Rory Holland to pull back the curtain on the operational realities of global payments and subscription models. With over two decades of experience spanning traditional powerhouse banks like JPMorgan Chase to hyper-growth fintech exits like Hyperwallet and Payoneer, Charles brings an authentic operator perspective to the mic.

The conversation explores the massive, often hidden threat of involuntary churnwhere mechanical payment failures quietly alienate good subscribers—and how Butter utilizes machine learning as a seamless predictive layer to capture lost revenue. Beyond the technology, Charles opens up about his journey from a competitive college athlete to building a fintech career, the deep personal influence of his father, and the invaluable leadership lesson of prioritizing long-term victory over short-term battles.

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Jaksot(47)

Interview with Colton Pond: The War Fintech Didn’t Win

Interview with Colton Pond: The War Fintech Didn’t Win

Host - Rory Holland - cstmr.com - Linkedin: CSTMRInterviewed - Colton Pond - socure.com / fintechnerdcon.com - LinkedIn: SocureIn This EpisodeColton Pond, Global CMO of Socure and co-founder of Fint...

13 Touko 48min

Interview with Bill Bloom: Lighting Money on Fire and the Quest to Pay off $1B in Consumer Debt

Interview with Bill Bloom: Lighting Money on Fire and the Quest to Pay off $1B in Consumer Debt

Host - Rory Holland - cstmr.com - Linkedin: CSTMRInterviewed - Bill Bloom - dianemoney.com - LinkedIn: Diane MoneyIn This EpisodeIn this episode, Rory Holland sits down with Bill Bloom, wealth archite...

23 Huhti 59min

Interview With David Benskin: A New Brand, a New Category, the 13-Year Evolution to Connected Intelligence

Interview With David Benskin: A New Brand, a New Category, the 13-Year Evolution to Connected Intelligence

Host - Rory Holland - cstmr.com - Linkedin: CSTMRInterviewed - David Benskin - wealthaccess.com - LinkedIn: Wealth AccessWant to be a part of the podcast? Contact Rory today!In This EpisodeIn this epi...

31 Maalis 46min

Interview with Chris Levy: Rising from Intern to CEO in Just Over a Decade

Interview with Chris Levy: Rising from Intern to CEO in Just Over a Decade

Host - Rory Holland - cstmr.com - Linkedin: CSTMRInterviewed - Chris Levy - pursuitlending.com - LinkedIn: PursuitWant to be a part of the podcast? Contact Rory today!In This EpisodeIn this episode, R...

17 Maalis 45min

Rory Holland and Jack Macy: A Conversation about Choosing the Right Agency and Partnering for the Long Haul

Rory Holland and Jack Macy: A Conversation about Choosing the Right Agency and Partnering for the Long Haul

Host - Rory Holland - cstmr.com - Linkedin: CSTMRInterviewed - Jack MacyDownload the Definitive Buyer’s Guide for Hiring a Financial Marketing AgencyWant to be a part of the podcast? Contact Rory toda...

3 Maalis 36min

Interview with Levi King: From Sign Shop to $100M Founder

Interview with Levi King: From Sign Shop to $100M Founder

Host - Rory Holland - cstmr.com - Linkedin: CSTMRInterviewed - Levi King, Nav.com, LinkedIn: Nav Want to be a part of the podcast? Contact Rory today!In This EpisodeIn this episode, host Rory Holland...

17 Helmi 57min

Interview with Joey Bouchard: The Insurance Industry Needed a ‘Human+’ Model

Interview with Joey Bouchard: The Insurance Industry Needed a ‘Human+’ Model

Host - Rory Holland - cstmr.com - Linkedin: CSTMRInterviewed - Joey Bouchard, QuoteWellWant to be a part of the podcast? Contact Rory today!In This EpisodeIn this episode of Mighty Finsights, host Ror...

4 Helmi 1h

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