Posts Categorized: Stories

The Wasp, the Caterpillar, and Cannibalizing Your Own Product from the Inside

This December, Freckle Time Tracking turns 6 years old. OMG! And 30×500 turns 5 years old… after a fashion. You see, the original 30×500 is dead. And the one before that. And the one before that. And the one before that, too. We killed them. Slowly. And we’re still killing them, even as I write… 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 »

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 »

Why you have to develop an Investment Mindset

Nobody wants to fail. Not really. Sure, failure is better than not trying at all… but success is better than failure. After 4 years of teaching designers & developers to make their first product dollar, Alex and I have seen every kind of failure, from failure to start at all, to failure to pull the… Read more »

“Done” should be spelled F-A-I-L

“It’s almost done, I just need to add this one more thing…” Whooooooa there. When you teach designers & developers to bootstrap their own product businesses, as I do, that’s a phrase you’ll hear a lot — and you’ll come to hear it (as I do) as the sound of a shotgun being removed from… Read more »

Fuck features you “have to have”

Photo Credit: eric Hews When we ran BaconBizConf, here’s just a smattering of the “crucial features” we left out: badges goodie (aka junk) bags a conference hotel multiple tracks a green room a hallway track (or even a hallway) a stage projectors (we used a big TV) wifi (yes, really, we offered no wifi) more… Read more »

The Psychological Self-Torture and Bootstrapping Podcast!

OK, so that title is a little bit of linkbait. Just a little bit. But, contrary to popular opinion, building software is easy… building a business is hard. The hardest parts are the least obvious. That’s what Justin Jackson and I talked about yesterday: the psychology, the mechanics, and my war stories from bootstrapping. Specific… Read more »

Curing the Lie of the Big Win (and the Big Fail)

We’re surrounded by the stories — the mytharc, if you will — of The Big Win. (Also the Big Fail.) “Twitter succeeded because…” “I failed because…” I’m here to tell you: That’s largely a load of crap. If you want to know why — and if you want to know how I succeed at so… Read more »