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: CSTMR

Interviewed - Chris Levy - pursuitlending.com - LinkedIn: Pursuit

Want to be a part of the podcast? Contact Rory today!

In This Episode

In this episode, Rory Holland sits down with Chris Levy, President and CEO of Pursuit, a mission-driven community development financial institution (CDFI). Chris shares his remarkable homegrown journey, rising from a summer intern to the head of the organization in just over a decade.

They dive into the discipline required to complete a law degree while working full-time, the strategic decision to rebrand a 70-year-old institution to unify its identity, and Pursuit’s pivotal role in deploying $780 million in PPP loans to small businesses. Chris also reflects on the human side of leadership—balancing a high-stakes career with the transition to first-time fatherhood and the value of embracing tough feedback to grow as an executive.

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Episoder(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 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 Apr 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 Mar 46min

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 Mar 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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