How Brett Helling Scaled to 1.5M Monthly Visitors with Website Acquisitions

Turning Failures into Foundational Experience

Brett Helling started by launching ten websites that flopped. He was in college and spent nights tinkering with themes, learning how search engines index pages and how small design tweaks can change bounce rates. Each failed project chipped away at his ego but sharpened his understanding of SEO basics. He also drove for rideshare companies and saw that limited information existed for drivers who wanted inside tips. That gap sparked a simple blog that became the foundation of his future.

Spotting the Opportunity on Flippa

After a $10,000 scam and several underperforming flips, Brett browsed Flippa’s classifieds and discovered Ridester—a rideshare platform domain with high-authority backlinks from Forbes and other outlets. He paid the founder, merged his personal rideshare blog into the Ridester domain, and refocused the site on advice, reviews, and earnings strategies. That pivot was the turning point.

Scaling to 1.5M Visitors

Within three years, Ridester climbed to 1.5 million unique visitors per month. Brett optimized underperforming posts, cleaned up the link profile, and produced deep-dive content on driver earnings, tax deductions, and app comparisons. Short tutorials, interviews with high-earning drivers, and data-driven posts helped the site rank for competitive terms. He relied on ad networks at first, then tested lead generation and service offers to boost revenue without degrading user experience.

Building a Team and Navigating HCU

By 2019, Brett assembled a manager for each site in his portfolio. Then COVID lockdowns arrived, traffic dipped, and hiring paused. Sites rebounded in late 2022 until Google’s September 2023 Helpful Content Update hit. Traffic and ad revenue plunged. He let the team go, retained core contractors, and spent nearly a year rebuilding content pillars and removing low-value pages to align with new search guidelines.

Revenue Diversification and Future Outlook

Having learned the hard way about algorithm risk, Brett now mixes ad networks with lead gen, services, and partnerships to diversify income. He still acquires stressed assets priced between $10K–$50K, looks for clean white-hat link profiles, and focuses on founders’ passion projects. His lean approach and willingness to do the work solo have allowed him to bounce back and keep a lifestyle business that stays somewhat passive once built.