He Quit His Job And Makes $10M/Year Writing Online

Dickie Bush was making $180,000 a year as a Wall Street hedge fund trader when he watched a 37-year-old colleague ask his boss for permission to attend his son's Little League game — and get denied. "If I do everything right for 14 more years, I might be sitting here having to ask for permission to go to my kids' Little League game," Bush recalls thinking. "Uh-oh, I gotta get out of here." He didn't quit. Instead, he started writing online while keeping his full-time job, eventually building four writing-based businesses on pace to do $10 million in 2024 — Ship 30 for 30 ($3M/year), the Premium Ghostwriting Academy ($5M/year), Write with AI ($500K), and TypeShare (a SaaS platform).

The Incentive Problem That Triggered the Pivot

Bush's Wall Street job had a structural flaw that broke his motivation: if he showed up at 5 AM and worked until 8 PM, he might make 10% more money. If he worked as little as possible, he'd make the same amount. "I couldn't apply the level of effort that I wanted to because my incentives weren't there," he says. That realization — that effort and reward were decoupled — became his first operating principle: if doubling your effort in your current vehicle doesn't lead to more income or more skill, find something else.