Meet Chris LaFay of Classic City Consulting

Today we’d like to introduce you to Chris LaFay.

Hi Chris, it’s an honor to have you on the platform. Thanks for taking the time to share your story with us – to start maybe you can share some of your backstory with our readers?
I’ve been building websites since elementary school. Back then, when the Harry Potter books were flying off the shelves at the school book fair, I wasn’t that kid. I wandered to the back corner and picked up a book called How to Build a Website for Kids. I brought it home, opened my computer, and started writing HTML.

In middle school, I met a teacher who genuinely changed my life. His name was Roderick Hames, and he gave me space in his computer lab to keep learning how to code with a few friends. During those years, I picked up small clients—nothing fancy, a few hundred dollars here and there to build personal websites. This was the era of Flash sites, which, honestly, I sometimes miss. There was a lot more personality on the web back then. Today, usability standards matter more (…and for good reason), but I really do miss the “personality” websites had back then.

My brother is about ten years older than me and was in college at the University of Georgia studying marketing and finance while all this was happening. When he saw what I was doing, he had the thought: If Chris can do this side, and I understand business, maybe we can turn this into something. He’d come home most weekends, and we’d work on projects together. I taught him design tools and the basics of the web, and we slowly turned it into a small business. Over time, our paths naturally diverged: he leaned into print and branding, and I leaned deeper into web design and development.

Through high school and college, I worked full-time jobs in web design and development while taking on freelance work on the side. Those jobs were flexible enough to allow that balance, until one day, my employer told me they wanted to convert me from full-time to a contractor. I asked for a guaranteed number of hours. They couldn’t offer that.

So….. they quietly got rid of me:

Week one: 40 hours.
Week two: 30.
Week three: 20.
Week four: 10.
Week five: zero.

Suddenly, I was on my own.

Fortunately, I had a handful of agencies I’d been freelancing with, each giving me 5–15 hours a week. I was able to piece together a full-time income surprisingly quickly. That moment shaped one of my core beliefs about work: I would rather have my income split across several clients than rely on one. If one goes away, income drops from 100% to 80%—not to zero.

As work increased, I brought in friends and former colleagues to help. Designers when design-heavy work came in. Developers when projects needed deeper technical help. That period (right after losing my full-time job) is when the business really began. Over the next 10–15 years, it grew slowly but steadily, adding contractors as needed and staying relatively healthy along the way.

I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
It has absolutely not been a smooth road.

I think of the business in phases.

Phase One (2008–2016) was essentially freelancing. It was mostly me, with one or two contractors I leaned on occasionally.

Phase Two (2016–2019) is when revenue increased and I did what I thought you were supposed to do: hire full-time employees. At the time, I didn’t have mentors or advisors, simply examples of other agencies that had teams. So when time became scarce and money was in the bank, I hired. Designer. Developer. Project manager. They all did great work, and many of our current processes were born during that period.

What I didn’t understand then was cash flow.

On paper, everything looked fine. If you start the month with $100, pay out $20, and collect $19, you’re “only” down $1. That feels manageable—especially when accounts receivable are floating around. But when you lose 1–2% every month for three years, it quietly drains everything.

In 2019, I woke up with no money in the bank and a $20,000 payroll due.

I started calling team members and vendors to ask for time, calling clients to ask them to pay invoices I just sent 30 seconds ago. It was rough. I had to let people go. One team member stayed and took a pay cut for several months while we stabilized. I went back into full execution mode, and within a year, we recovered everything we had lost.

That was the wake-up call.

Phase Three (2019–2025) is when I finally brought advisors and mentors into the picture. I became an open book: sharing financials, contracts, pricing, sales processes. That transparency changed everything. Revenue grew consistently year over year, but new challenges emerged: rising operating expenses and increasing project minimums.

Agencies are people-heavy businesses. As teams grow, minimum viable project sizes grow too. Lead generation became the limiting factor. My personal network, which had sustained the business for years, wasn’t keeping pace with the revenue required to support a traditional agency structure.

So we changed again.

Over the last year, we shifted to a collective model: working directly with trusted experts and assembling teams based on specific client problems. It gives us flexibility to scale up or down without the weight of fixed overhead. More importantly, it lets me do the part of the business I enjoy most: hearing a real problem and putting the right people around it.

The best feedback we get is simple: “You delivered what you promised.” That’s what keeps me going.

Alright, so let’s switch gears a bit and talk business. What should we know?
Originally, we were purely a web design and development shop, because that’s what I knew how to do. Between 2016 and 2025, we experimented with expanding into adjacent services like branding, messaging, and paid ads. We did solid work, but we struggled to tell a cohesive story about the value we were delivering. Often, campaigns worked well enough that clients didn’t need ongoing iteration—and that’s fine—but it made those services less aligned with how we wanted to operate.

By 2024, we made a clear decision: we are a web design and development company. That’s what we do best. That’s what people know us for. So we doubled down.

Many of our agency partners don’t like doing web work. It’s complex, margin-sensitive, and hard to staff internally. While others are pulling away from web, we’re leaning into it. Historically, our work has been primarily WordPress-based marketing sites, but over the last few years, we’ve expanded into Shopify through agency partnerships. That’s been especially exciting as e-commerce allows you to test ideas quickly and see real results fast.

What truly sets us apart, though, is how our business grows. Most of our work comes through referrals, especially from agency partners. That’s led me to focus heavily on community building rather than traditional marketing. Instead of ads or SEO-heavy strategies, my goal is to stay consistently valuable to the people in our network.

I’m okay with slower growth if it means higher profitability, happier clients, satisfied collaborators, and a business that actually lasts.

Risk taking is a topic that people have widely differing views on – we’d love to hear your thoughts.
I’m not a risk-taker. Not at all.

A few years ago, our team took a personality assessment.. one of those quadrant-style charts with dozens of possible profiles. Out of 72 possible outcomes, the three longest-tenured leaders on our team (myself included) landed in the exact same box: introverted, operational, detail-oriented. Most of the team clustered nearby.

One teammate joked, “This is why Classic City grows slowly. No one’s running through brick walls.”

He wasn’t wrong.

Could we grow faster with someone willing to take massive swings on lead generation? Probably. But that hasn’t been our DNA. Instead, we’ve leaned into thoughtful growth: building trust, structure, and long-term relationships.

To me, the biggest risk isn’t growing slowly. The biggest risk is growing fast without understanding the cost. I’d rather build something durable than sprint toward something fragile.

And honestly? I’m good with that.

Contact Info:

• Website: https://classiccity.com
• LinkedIn: https://www.linkedin.com/in/chris-lafay/