How Tim worked on side-projects for 10+ years, and finally went full-time (with kids)

What It Covers

Tim Leland shares his decade-long journey building side projects while raising three boys, eventually reaching double his salary before going full-time on t.ly, a URL shortener competing against established players like Bitly.

Key Questions Answered

• •Financial guardrails for going full-time: Wait until side project revenue reaches double your current salary before quitting, not just matching it. This buffer accounts for business expenses, self-employment taxes, health insurance costs, and potential revenue fluctuations while providing psychological safety with young children dependent on your income.
• •Time management with young children: Use constrained time blocks when kids nap or after bedtime to force focused execution rather than endless planning. Limited availability creates natural Pomodoro sessions that prioritize shipping over perfection, helping solo founders build and iterate faster than those with unlimited time who overthink decisions.
• •SEO strategy for competitive markets: Listen to customer feature requests, build what they ask for, then write blog posts targeting those exact search terms. Tim ranks on page one for URL shortener searches by creating tools like QR code builders and bulk shortening features that people actively search for daily.
• •Affordable pricing as differentiation: Positioning as the more affordable option works when you have sufficient volume and manageable support costs. Tim charges significantly less than Bitly's thousand-dollar custom domain pricing, capturing solo users and small companies who need basic features without enterprise complexity or budget requirements.