Topics in ‘Bootstrapping’

Confessions of a (reformed) whiner

Hey guys! This is a guest post by 30×500 alum Ryan Castillo, author of 7 Recurring Revenue Recipes for Freelancers and reformed procrastinator. Hi. My name is Ryan and I am a whiner. Or at least I used to be, but we’ll get to that in a minute. For the past three years I’ve failed… Read more »

The 3-part 30×500 Taste Test

OK, dudes and dudettes… t-minus 6.5 hours and counting til we close registration on the 30×500 Academy. Time to break out that neglected browser tab you set aside for later and choose, no… or yes. To help you decide, if you’re the type who likes to try before you buy… we got you covered. With… Read more »

The Ebomb Recipe That Works (free lesson)

The internet is full of hand-wavy advice. Not even bad advice, necessarily, but vague. The kind of advice that makes perfect sense in the moment, that makes you FEEL good, but then when you sit down to actually try it yourself… Pffft! Nothing comes out. How do you actually do it? You don’t know. They… Read more »

Making huge projects work: Implementation

In my last essay, I totally pulled back the curtain on the planning + design stage of the (huge) brand new 30×500. The next step? Action, baby. And the key takeaway? Work has an interface and experience all its own… and YOU get to design YOURS. Do it right, and it’ll pay you back. Typically,… Read more »

Making huge projects work

You know I always tell you: you should do a tiny project first. You know I always advise that you must accept that good things take time, work incrementally, and keep stacking the bricks. Buuuut… sometimes you need to go big. You can build a lot of things nibble by nibble, but sometimes you need… Read more »

The Ship by September Challenge

Let’s talk about That Thing. You know, That Thing you want to work on. That Thing you dream of finishing. That Thing that’s sitting, unfinished (or unstarted) on your desk or your hard drive. Or, uh, a vague dream only in your head. You keep saying you “need to find the time” to work on… Read more »

The sounds of self-sabotage

I skipped the steps and it didn’t work! It will never work! It’s a lie! I’m a failure! I suck! This sucks! Screw everything! … I can’t set a price on my book… I’ll make my potential customers do it! I’ll set up Pay What You Want! … I’m gonna re-start my newsletter! There will… Read more

The 24-Hour Book Challenge — A Six Month Update

On December 2nd, I sat down and started writing. 24 hours later, I launched the first (beta) version of my first biz book, Just Fucking Ship. After a couple more weeks of work, I shipped the final(ish) version. Then I put JFS on a shelf for a while in favor of more urgent/demanding things. Now,… Read more »

Be Your Own Angel – a revenue model for slow startups

Yes, recurring revenue grows sloooooowly. How do you, founder of a baby bootstrapping biz, survive the lean year or two before it can pay all your bills? Well, I have a strategy. I call it Be Your Own Angel. Last week, I gave a talk about it — in greater detail than ever before! —… Read more »

What does ’30×500′ even mean?

April, 2010. The party bus was rolling down the highway from Dublin to Kilkenny; it was upholstered in sparkly red and orange vinyl and full of my favorite kind of nerd, and I was perched on the stool in front with a mic clutched in my hand. I had just finished an impromptu little story… Read more »

Hey, why not get a shiny
Freckle Time Tracking