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: CSTMR

Interviewed - Bill Bloom - dianemoney.com - LinkedIn: Diane Money

In This Episode

In this episode, Rory Holland sits down with Bill Bloom, wealth architect and founder and CEO of Diane Money, to explore what it really takes to break free from the debt cycle — and why so few people ever do. Bill reflects on his path from Prudential financial advisor to building an app named after his mother, a woman who carried 45 credit cards and inspired a mission to eliminate a billion dollars of bad debt.

They discuss why the financial system is engineered to keep people in debt, how most of us inherit our money beliefs before we ever earn our first paycheck, and what it actually looks like to build a roadmap out of the cycle. Bill also gets candid about pouring over $200,000 into failed development attempts — and why he never quit. Beyond the app, Bill and Rory get honest about their own financial struggles, the shame that keeps people silent, and why the most powerful financial tool available to anyone might just be a real conversation.

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Avsnitt(46)

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...

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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 Mars 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 Mars 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 Mars 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 Feb 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 Feb 1h

Interview with Jack Macy, Brendan Bresnahan and Romina Gomez: Gaining Maximal Visibility in the AI Age

Interview with Jack Macy, Brendan Bresnahan and Romina Gomez: Gaining Maximal Visibility in the AI Age

Host - Rory Holland - cstmr.com - Linkedin: CSTMRInterviewed - Jack Macy, Brendan Bresnahan, Romina Gomez Want to be a part of the podcast? Contact Rory today!In This EpisodeJoin Rory Holland and a pa...

20 Jan 35min

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