In 2008, Garry Conn and John Cow went head-to-head in a competition to see who could build and sell a blog for the most money in 30 days. The winner would be determined by the final sale price on SitePoint's marketplace. It was a fun, public challenge that taught the community a lot about building websites with the intent to sell them.
The contest generated serious buzz. Joel Comm contributed a copy of his Secret Classroom course as a prize for participants who helped promote Garry's entry — a site called Debt Consolidation Book that offered free ebook downloads and email list building. The promotional playbook was pure 2008: Digg it, StumbleUpon it, bookmark it on Del.icio.us, add it to Yahoo Bookmarks and Propeller and Mixx. Every one of those platforms is either gone or unrecognizable today.
What Blog Flipping Actually Was
Blog flipping was the practice of building a website, growing its traffic and revenue, and selling it for a profit — essentially real estate investing applied to the internet. The concept made sense then and still makes sense now, even though the tactics have evolved completely.
In the Conn vs. Cow contest, the strategy was to build a content site in a profitable niche (debt consolidation), stuff it with content, build an email list, drive traffic through social bookmarking, and flip it on SitePoint's marketplace within 30 days. The fact that both competitors could realistically expect to build and sell a monetized blog in a month tells you how different the internet was back then.
Website Flipping in 2026
The concept of building and selling websites is alive and well, but the timeline and complexity have changed dramatically.
Where Websites Are Bought and Sold
SitePoint's marketplace evolved into Flippa, which remains one of the largest marketplaces for buying and selling online businesses. For higher-value sites, Empire Flippers and Quiet Light handle brokered transactions with more vetting and support. Motion Invest specializes in smaller content sites under $100,000. Acquire.com handles SaaS and tech businesses.
What Buyers Actually Want
Modern website buyers are sophisticated. They want to see:
- At least 12 months of consistent revenue — the 30-day flip is essentially dead
- Diversified traffic sources — sites dependent on a single Google ranking are risky
- Clean analytics — Google Analytics, Search Console data, and verified revenue
- Documented processes — SOPs for content creation, link building, and maintenance
- Defensible content — original, expert-driven content that AI cannot easily replicate
Typical valuations run 30 to 40 times monthly net profit for content sites, and higher for established brands with email lists and multiple revenue streams.
Building a Site to Sell
If you wanted to build a website with the intent to sell it today, here is a realistic approach:
- Choose a niche with proven buyer demand — finance, health, B2B software, and outdoor recreation all command premium multiples
- Build on WordPress with a clean, fast theme and solid hosting
- Create high-quality content targeting keywords with commercial intent
- Diversify monetization — combine affiliate income, display ads (Mediavine or Raptive), and digital products
- Build an email list — sites with engaged email subscribers sell for significantly more
- Document everything — a well-documented site is easier to transfer and commands a higher price
- Plan for a 12 to 24 month build before listing for sale
What the 2008 Contest Got Right
Looking back, the Conn vs. Cow competition had the right instinct: treat website building as a business, not a hobby. Build with intention, focus on monetizable niches, and think about your exit from day one. The specific tactics — social bookmarking blitzes, contest-driven link building, 30-day timelines — were products of their era. But the entrepreneurial thinking behind them was solid.
The internet marketing community in 2008 was smaller, scrappier, and more willing to experiment publicly. I miss that energy sometimes. If you are interested in building websites to sell, the opportunity is bigger than ever. Just plan for a marathon, not a sprint.
