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

54 min episode · 2 min read
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How Tim Worked

Episode

54 min

Read time

2 min

Topics

Productivity, Health & Wellness, Startups

AI-Generated Summary

Key Takeaways

  • 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.

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.

Notable Moment

Tim reveals he grew a Chrome extension to 450,000 users before building t.ly, using the free extension as his primary customer acquisition funnel. Most users create free shortened links, but the massive volume provides enough conversions to sustain full-time income.

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Episode Transcript

This podcast is hosted by transistor dot f m. Hey, everybody. Welcome to Build Your SaaS. This is the behind the scenes story of building a web app in 2023. I'm Justin, and today I've got a guest, Tim Leland. Tim, how's it going, man? It's going good. Great to finally be on here. I've been listening to you for feels like years. I don't even know how far back. Yeah. When did we start the show? We started in 2018, so it's been going going for a while. And, you reached out. Actually, I got I got a message from your wife and a message from you. So I I I got doubled up. You you doubled up on, feedback on the Aaron Francis episode, and you said, hey. I think it'd be fun to have me on and talk about your experience bootstrapping on the side, and you've just recently gone full time. Is that right? Yep. About a month ago. About a month ago. And the product is t dot l y, which is a URL shortener, which I think we can get into that too. That's that that seems like a competitive category. But maybe just for the folks at home, describe what you've been doing, you you know, for the past while, what you've been working on, and how you kind of built yourself up to going full time a month ago. Yeah. It's it's a long story. I'll try to tell you the, short version, but, you know, it really goes back to college, graduated college, and just got a job working, you know, software developer and started building websites on the side. And then eventually, that turned into small apps. And then I got and got into, like, the Chrome extension space and started building a few Chrome extensions. And then, it's kinda led me to where I'm at now to where, you know, I had a a weather extension that grew to, like, 250,000 users. Didn't make a ton of money, but it was nice side income. And then I built a link shortener extension, and that actually is kinda took off and has 450,000 users. And then that led me to TDI l y. Wow. Okay. And, and you've you've also got a family. You've got you've got kids as well? Yep. Yep. I have a eight year old, five year old, and three year old. All all boys. Eight year old, five year old, and three year old. All boys. Three boys. Okay. You're similar to to my setup, except our we have four, and our oldest is a girl. So we now she's at college, and we've got three boys at home. And and my wife is, like, sad because there's there's no girls around anymore. Just just us four boys. You said, okay. I wanna you said, I wanna pitch you on the idea of coming on the pod and sharing my journey of building side projects for …

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  • eventually reaching double his salary before going full-time on t.ly, a URL shortener competing against established players like Bitly
  • Tim reveals he grew a Chrome extension to 450,000 users before building t.ly, using the free extension as his primary customer acquisition funnel
  • going full-time on t.ly, a URL shortener competing against established players like Bitly

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