iSideWith

Taylor Peck and his engineer co-founder were roommates after college with a fundamental difference: Taylor was a political news junkie while his friend was a disenfranchised voter who didn't care about politics. They lacked a tool to bridge this gap and have a real conversation about their differing views. One weekend, they decided to solve this problem by building something simple but powerful: a 10-question political quiz with an algorithm to match people to candidates and parties.

The initial quiz took just a weekend to build. They posted it on Facebook and added more questions based on user feedback. The response was staggering—within six months, over 6 million people had organically taken the quiz and shared it with friends. This wasn't paid marketing or a product hunt launch. It was pure virality driven by the engaging quiz format and genuine user interest in understanding their political alignment.

The platform's early growth came entirely through word-of-mouth and organic Facebook sharing. As the user base grew to 25 million quiz takers over nearly four years, Taylor and his co-founder optimized the experience through constant A/B testing. Each of the 25 million users who took the quiz provided an average of 35.8 questions worth of data, resulting in nearly 1 billion total answers collected. By the time of this interview, they were averaging 3-5 million unique visitors per month during political seasons, with about 1.5 million new quizzes completed monthly—a ~30% conversion rate from visitor to quiz taker.

What worked was the simplicity of the quiz format combined with genuine utility. The 30% conversion rate far exceeded typical SaaS landing page performance (4-5%). The quiz asked meaningful questions and provided real value to users trying to understand their political alignment. Taylor's co-founder, who had lived through the dot-com bust of 1999, instilled a lean operating philosophy. Their hosting costs ran just $5-6k per month on Amazon Web Services, and Taylor personally spent under $2,500/month on living expenses. This lean approach allowed them to stay independent and focused on user value rather than forcing monetization.

What didn't work (yet) was aggressive monetization. They experimented with sponsored candidate ads and email list monetization but found these less effective than building out better tools. Google AdSense generated about $10k monthly, of which $5-6k went to hosting, leaving minimal profit. Taylor's personal salary was very low—roughly $20-30k annually—but he was sustained by his wife's support and faith in the project's potential.

By 2016 (the interview timeframe), iSideWith had become a political machine with 25 million quiz takers and 3 million email subscribers (a 10-12% signup rate from quiz takers). They were expanding internationally to Brazil, France, and Spain with translation teams. Revenue was still modest at roughly $10k/month, but Taylor was building toward a new monetization model: tools for candidates like Hillary, Bernie, and others to log in and run sponsored placements directly, paying on a cost-per-email (CPA) basis. This represented a shift from one-off ad sales to a self-service platform where campaigns could manage their own targeting and budgets. At 33 years old, Taylor credited his early morning wake-up routine (5-5:30 AM) and his co-founder's dot-com-era wisdom about staying lean as keys to keeping the business independent and user-focused.