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RyanCwynar
RyanCwynar

Posted on • Originally published at ryancwynar.com

The Ugly Site Prospecting Strategy: Building Free Redesigns to Win Clients

Most cold outreach fails because you're asking before you've given anything. The typical pitch — "Hey, your website sucks, want to pay me to fix it?" — gets ignored or deleted.

I've been experimenting with a different approach: find businesses with genuinely outdated websites, build them a complete redesign for free, then reach out with a live demo.

The Strategy

The concept is simple:

  1. Find ugly sites — Local businesses with websites that look like they were built in 2008. Clip art, dead social links (looking at you, Google+), clashing colors, broken layouts.

  2. Score them — I use a 1-10 scale. Anything below 5 is a candidate. The sweet spot is businesses with terrible websites but clear signs of legitimacy: established for 20+ years, multiple locations, decent Google reviews.

  3. Build a redesign — Not a mockup. A fully functional static site hosted on GitHub Pages. Takes 30-60 minutes with modern tooling. Mobile-responsive, clean CTAs, proper typography.

  4. Reach out with the demo — The pitch becomes: "I built this for you. Take a look. If you want to use it, let's talk."

Why Static Sites?

You might wonder why GitHub Pages instead of a proper CMS. A few reasons:

  • Zero hosting costs — I can build 50 demos without spending a dime
  • Fast iteration — Push a commit, site updates in seconds
  • Clean handoff — If they say yes, I can port it anywhere
  • Proof of work — The live site IS the portfolio piece

Most of these businesses don't need a complex CMS. They need a site that loads fast, looks professional, and has their phone number in big letters.

What I've Learned

Family-owned businesses are the sweet spot. A plumber who's been in business since 1982 with a site that has a woman floating underwater surrounded by sea turtles? That's a real example. They know their site is bad. They've just never had someone offer to fix it in a way that felt low-risk.

The outreach matters. I send a simple SMS: "Hey [Name], I'm a developer in the area. I noticed your website and built you a free redesign: [link]. No strings attached — just wanted to share." Then I add them to a call queue for follow-up.

Multi-channel works. SMS for the initial touch (high open rate), followed by a phone call if they've clicked the link. Email as a backup for businesses that list one.

Speed is a feature. I can go from finding a prospect to sending them a live demo in under an hour. That velocity means I'm not agonizing over each one. Some convert, most don't. Move on.

The Tech Stack

Nothing fancy:

  • HTML/CSS/JS for the sites (sometimes Tailwind for speed)
  • GitHub Pages for hosting
  • A simple prospect tracking system in Convex
  • Twilio for SMS outreach
  • Call queue automation for follow-ups

The whole workflow is designed for volume. Find, build, ship, reach out, repeat.

Does It Work?

It's still early, but the response rate is dramatically higher than cold emails pitching services. When someone can click a link and see their business name on a beautiful website, the conversation changes.

You're not selling anymore. You're showing.

Try It Yourself

Pick a niche. Find 10 businesses with terrible websites. Build them redesigns. Reach out. See what happens.

The worst case? You've built 10 portfolio pieces that prove you can ship fast. The best case? You've got clients who came to you with trust already established.

That's the thing about giving first — it reframes the entire relationship.

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