Posts Categorized: Bootstrapping

Startup Winter is Coming

Do you remember the mortgage crisis? In case you didn’t hear about it — or don’t remember the details — it worked something like this: Banks figured out a new way to profit from mortgage loans, even if the loans never got paid back… …which led them to loan money to people who’d never be… Read more »

From Zero to $3k MRR in 10 days — the story of launching RubySteps

Less than 2 weeks ago, Ruby developer Pat Maddox‘s rent was due. He had quit his job some time before. He had no audience or mailing list, no products… But he did have one thing: He had a pile of hard-earned Sales Safari research, thanks to his time in our 30×500 Product Launch Class. So… Read more »

Is bad copy killing your product?

This is a horror story. This is a story about the lurking, creeping horror of killer copy. Not the good kind of “killer” — no, not dope or sick or totally bad — but the kind that murders your ambitions in their cradle. Spoilers: This horror story has a happy ending. And if you watch… Read more »

Help! My SaaS isn’t growing! +60% revenue, 1 year later…

Just about a year ago, I wrote that Freckle had hit the Plateau of Doom. We were dead in the water at $28,000 a month. We’d grow a little… then shrink a little, grow a little, shrink a little… for months at a time. Why? y=mx+b. Growth (new accounts) is pretty much linear, a reliable… Read more »

Startup Escape Plan: How to free up time, energy & money to build your future

When you stop working for the day, have you really gotten anywhere? Will the hours that you spent today still be paying off for you next week, next month, next year? If your answer is “No,” then you’re probably here because you’re somewhere on the left side of this spectrum: But you want to be… Read more »

Oxygen Mask Entrepreneurship

Back when I was 24-25, I told myself that our brand new baby business would be doing $1-2 million a year by the time I turned 30. My 30th birthday is Sunday. Did we make it? Nope. Am I sad? Nope! So, should I then be giving thanks to the overweening power of subconscious self-protection… Read more »

Mojito Island & Entreporn, Revisited

This article is about Entreporn and Mojito Island, and the emotionally manipulative fantasy narratives of “success.” Entreporn is a word I coined, on this podcast. Mojito Island is another term of art that you might want to know, coined by DHH himself. Without further ado… If you ever wanted to understand the startup media through… Read more »

Fuck “Innovation” 2: Time is a Line, You Guys!

I’m writing this on Friday at 8pm. Slightly soused, if you must know. Just a scant 2 hours ago, Alex and I wrapped up our infamous 30×500 Bootcamp, 7 (really 8) hours a day, two days in a row. Yes, the lessons are pre-recorded, but the homework critique, the guidance, the Q&A? Totally live. Then… Read more »