Impossible & Paleo Meal Plans

Joel Runyon graduated in 2009 into the worst job market in decades. After striking out at Starbucks and Target despite his degree, he landed seasonal work at UPS delivering packages in Chicago winters. When he was laid off after two months, rather than despair, he did something unexpected: he started a blog called the Impossible List. Inspired by bloggers traveling the world and friends moving to Thailand, Joel couldn't pursue those adventures yet—but he could train for a triathlon. That one small win, completing an indoor triathlon, fundamentally shifted his thinking. "You spent so much time telling yourself that this was impossible. What other things are out there that you think are impossible, but you could do if you just trained for it?" He realized his limitations were mostly mental.

While working at a marketing agency (initially for nearly free, learning on the job), Joel began documenting his impossible list on a blog in 2010. For two years, he maintained a consistent publishing schedule, writing about his fitness challenges, travels, and personal experiments. He did guest posts, commented on other blogs, and built genuine relationships with other creators. He wasn't trying to sell anything—he was just sharing interesting things he was doing. Simultaneously, he was acquiring hard skills: SEO, PPC advertising, social media, email marketing. He started freelancing nights and weekends, initially making $200-500/month on the side, eventually scaling to $1,500-2,000/month. When a larger marketing firm recruited him to manage national accounts like Camping World, the rigid structure (specific times, specific dress code, required location in Milwaukee) felt suffocating. Within six months, despite good pay, he left to go full-time on his own, first moving to the Dominican Republic to minimize living costs ($100/month rent) while he figured out how to scale his freelance work.

Joel's first monetization attempts on the Impossible blog didn't work. A "How to Run Your First Triathlon" product "bombed"—the intersection of fitness, running, and triathlon interest was too small. But he kept experimenting. In 2012, he was doing a six-pack challenge and blogging about a "modified form of the Paleo diet." Readers started asking questions. He created a simple one-page FAQ answering paleo questions and directed traffic there. The response was overwhelming. Rather than build a fancy product, he created a 21-day email challenge using ConvertKit or MailChimp—basically an automated email sequence where subscribers received daily tips and guidance for going paleo. People started paying for it. He also created meal plans manually, making PDFs by hand each week and sending them out Saturdays to paying subscribers. No coding required. No complex features. Just simple value in response to real customer demand.

What worked: consistent blogging over years built an audience and credibility. One viral post—a story about meeting Russell Kersh, inventor of the pixel—crashed his site when it hit Hacker News. That brought new audiences. The key was volume and persistence: 1,000 "at bats" over years meant some things would resonate even if most didn't. What worked: listening to an engaged audience. He didn't guess what paleo customers wanted; they told him. When he got overwhelming email asking about paleo, he met the demand.

What didn't work: relying purely on affiliate income. He'd seen companies lose 50%+ revenue overnight when affiliate relationships changed (DISH Network cut a company's PPC position). What didn't work: overbuilding. He deliberately started simple—manual PDFs, email sequences, no complex software—because he believed constraints forced focus. Many entrepreneurs substitute "what features should I build" for "what will customers actually pay for" and end up with overengineered solutions nobody buys.

By the time of this interview (roughly 2015-2016), Joel had multiple revenue streams: the Impossible mindset/fitness business, the Ultimate Paleo Guide affiliate site, a 21-day paleo challenge, recurring meal plan subscriptions, and eventually paleo-related apps. He still did occasional consulting for funded startups. The formula was to document interesting personal experiments, listen for what resonates with his audience, and double down on those signals. He remained disciplined about not overbuilding—the meal plans stayed simple text-based services until paying customers themselves requested dynamic software features. Only then did he hire developers to build a more technical product. By staying bootstrapped and keeping costs low, he maintained control and profitability. His "intersection of business and adventure" philosophy meant he only built businesses around things he genuinely did—which gave him authentic authority and kept the work interesting.