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Entrepreneur's Enigma

How Childhood Curiosity Led Chris LaFay to Two Decades in Digital Business

Nov 11, 2025 By MPN

Chris LaFay is the founder of Classic City Consulting, an agency that specializes in transforming cluttered, confusing websites into clear, conversion-driven experiences. For over two decades, Chris has been helping growing businesses cut through the digital noise—streamlining their messaging, simplifying their navigation, and turning their websites into actual business tools instead of digital brochures. Key Moments [05:41] High School Web Design Journey [08:49] "Freelance Path to Stability" [10:52] Diversify Income Streams [16:48] Identity Beyond Business [18:00] Work-Life Balance & Connections Find Chris Online https://classiccity.com https://www.linkedin.com/in/chris-lafay/ If you’re enjoying Entrepreneur’s Enigma, please give me a review on the podcast directory of your choice. The show is on all of them and these reviews really help others find the show. iTunes: https://gmwd.us/itunes Podchaser: https://gmwd.us/podchaser TrueFans: https://gmwd.us/truefans Also, if you’re getting value from the show and want to buy me a coffee, go to the show notes to get the link to get me a coffee to keep me awake, while I work on bringing you more great episodes to your ears. →  https://gmwd.us/buy-me-a-coffee Support me on TrueFans.fm → https://gmwd.us/truefans. Support The Show & Get Merch: https://shop.entrepreneursenigma.com Want to learn from a 15 year veteran? Check out the Podcast Mastery Community: https://www.skool.com/podcast-mastery/about Follow Seth Online: Instagram: https://instagram.com/s3th.me LinkedIn: https://www.linkedin.com/in/sethmgoldstein/ Seth On Mastodon: https://indieweb.social/@phillycodehound The Marketing Junto Newsletter: https://MarketingJunto.com Leave The Show A Voicemail: https://voiceline.app/ee

How Childhood Curiosity Led Chris LaFay to Two Decades in Digital Business
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Chris LaFay is the founder of Classic City Consulting, an agency that specializes in transforming cluttered, confusing websites into clear, conversion-driven experiences. For over two decades, Chris has been helping growing businesses cut through the digital noise—streamlining their messaging, simplifying their navigation, and turning their websites into actual business tools instead of digital brochures.

Key Moments

[05:41] High School Web Design Journey

[08:49] “Freelance Path to Stability”

[10:52] Diversify Income Streams

[16:48] Identity Beyond Business

[18:00] Work-Life Balance & Connections

Find Chris Online

https://classiccity.com

https://www.linkedin.com/in/chris-lafay/

If you’re enjoying Entrepreneur’s Enigma, please give me a review on the podcast directory of your choice. The show is on all of them and these reviews really help others find the show.

iTunes: https://gmwd.us/itunes

Podchaser: https://gmwd.us/podchaser

TrueFans: https://gmwd.us/truefans

Also, if you’re getting value from the show and want to buy me a coffee, go to the show notes to get the link to get me a coffee to keep me awake, while I work on bringing you more great episodes to your ears. →  https://gmwd.us/buy-me-a-coffee

Support me on TrueFans.fm → https://gmwd.us/truefans.

Support The Show & Get Merch: https://shop.entrepreneursenigma.com

Want to learn from a 15 year veteran? Check out the Podcast Mastery Community: https://www.skool.com/podcast-mastery/about

Follow Seth Online:

Instagram: https://instagram.com/s3th.me

LinkedIn: https://www.linkedin.com/in/sethmgoldstein/

Seth On Mastodon: https://indieweb.social/@phillycodehound

The Marketing Junto Newsletter: https://MarketingJunto.com

Leave The Show A Voicemail: https://voiceline.app/ee

Host/Producer/Booker: Seth Goldstein of Goldstein Media LLC
Podcast Network: Marketing Podcast Network

AI Disclosure: The only thing that is AI generated is the intro voice guy and any long transcripts.

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