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Agency founder Chris LaFay joins me to talk about growing a web business from small-town freelancing to seven figures, the power of sharing experience instead of advice, and what it really takes to scale sustainably without losing yourself.
🔗 Connect with Chris LaFay:
Website: https://www.classiccity.net
LinkedIn: https://www.linkedin.com/in/chrislafay
X: https://x.com/chrisjlafay
🔗 Connect with Mark Szymanski:
Website: https://markszymanski.co
Facebook: https://mjs.link/FB
Instagram: https://mjs.link/IG
LinkedIn: https://mjs.link/LI
X: https://mjs.link/X
YouTube: https://mjs.link/YT
About the show:
Fueled By Progress is a podcast about candid conversations with builders, creators, and curious people—focused on decisions, disciplines, and stories that move us forward.
If you’re new here, welcome. If you’ve been here since episodes recorded in my car—thank you. We’re still just getting warmed up 💪
Host --- Mark Szymanski: https://markszymanski.co/links
Video/Audio Production --- Nathaniel DeHaven: https://elevatedmultimedia.com
Chapters:
0:00 Intro and why I film first conversations
1:12 Meet the guest Chris LaFay and Classic City Consulting
3:11 How we got connected through Andy Milligan
4:30 Accountability partner dynamic and daily check-ins
6:40 Experience vs advice and why stories land better
8:46 Lessons from Entrepreneurs’ Organization on sharing experiences
10:46 My learn try share motto and staying authentic
12:10 What I’m excited about now daily shorts streak hits 100
13:20 Documenting life systems and personal website roots
15:03 Chris’s background slow and steady agency growth
16:25 Content ramp up and finally starting a podcast
18:58 Framing the studio and committing to a setup
20:06 Content to drive Classic City sales the game plan
21:17 Collaborations and mini series with agency partners
22:52 The dual CTA idea and jabs before the right hook
24:05 My path agency vs creator split and tradeoffs
25:27 Chris’s origin suburbs of Atlanta and early freelancing
27:12 Pricing mindset shift charging more with confidence
29:21 Scaling to 1.3M and hard lessons on expenses
30:53 Selling to CMOs vs founders and changing rooms
33:04 College path MIS degree and real world skills
35:39 First WordPress class and stepping up to teach
37:49 From Dreamweaver to WordPress becoming the core stack
41:26 Shopify side work and where it fits
42:53 What Chris does today founder CEO head of sales
44:38 Relationship driven sales and creating a repeatable engine
48:04 Why ads waited the need for a foot in the door offer
50:14 ICP clarity B2B SaaS with complex content models
52:18 Component libraries CPTs and empowering marketing teams
54:50 How they entered B2B SaaS referrals and Slack groups
56:40 Personal sites as scratch pads and short posts
59:28 Substack vs WordPress and owning the home base
1:02:44 Personal brand ideas fractional consulting with founders
1:05:20 Building new lines of business inside existing engines
1:06:56 Community and mentorship possibilities
1:07:24 Wrap up and where to find Chris LinkedIn and Classic City
Agency founder Chris LaFay joins me to talk about growing a web business from small-town freelancing to seven figures, the power of sharing experience instead of advice, and what it really takes to scale sustainably without losing yourself.
🔗 Connect with Chris LaFay:
Website: https://www.classiccity.net
LinkedIn: https://www.linkedin.com/in/chrislafay
X: https://x.com/chrisjlafay
🔗 Connect with Mark Szymanski:
Website: https://markszymanski.co
Facebook: https://mjs.link/FB
Instagram: https://mjs.link/IG
LinkedIn: https://mjs.link/LI
X: https://mjs.link/X
YouTube: https://mjs.link/YT
About the show:
Fueled By Progress is a podcast about candid conversations with builders, creators, and curious people—focused on decisions, disciplines, and stories that move us forward.
If you’re new here, welcome. If you’ve been here since episodes recorded in my car—thank you. We’re still just getting warmed up 💪
Host --- Mark Szymanski: https://markszymanski.co/links
Video/Audio Production --- Nathaniel DeHaven: https://elevatedmultimedia.com
Chapters:
0:00 Intro and why I film first conversations
1:12 Meet the guest Chris LaFay and Classic City Consulting
3:11 How we got connected through Andy Milligan
4:30 Accountability partner dynamic and daily check-ins
6:40 Experience vs advice and why stories land better
8:46 Lessons from Entrepreneurs’ Organization on sharing experiences
10:46 My learn try share motto and staying authentic
12:10 What I’m excited about now daily shorts streak hits 100
13:20 Documenting life systems and personal website roots
15:03 Chris’s background slow and steady agency growth
16:25 Content ramp up and finally starting a podcast
18:58 Framing the studio and committing to a setup
20:06 Content to drive Classic City sales the game plan
21:17 Collaborations and mini series with agency partners
22:52 The dual CTA idea and jabs before the right hook
24:05 My path agency vs creator split and tradeoffs
25:27 Chris’s origin suburbs of Atlanta and early freelancing
27:12 Pricing mindset shift charging more with confidence
29:21 Scaling to 1.3M and hard lessons on expenses
30:53 Selling to CMOs vs founders and changing rooms
33:04 College path MIS degree and real world skills
35:39 First WordPress class and stepping up to teach
37:49 From Dreamweaver to WordPress becoming the core stack
41:26 Shopify side work and where it fits
42:53 What Chris does today founder CEO head of sales
44:38 Relationship driven sales and creating a repeatable engine
48:04 Why ads waited the need for a foot in the door offer
50:14 ICP clarity B2B SaaS with complex content models
52:18 Component libraries CPTs and empowering marketing teams
54:50 How they entered B2B SaaS referrals and Slack groups
56:40 Personal sites as scratch pads and short posts
59:28 Substack vs WordPress and owning the home base
1:02:44 Personal brand ideas fractional consulting with founders
1:05:20 Building new lines of business inside existing engines
1:06:56 Community and mentorship possibilities
1:07:24 Wrap up and where to find Chris LinkedIn and Classic City