
Ryan Irelan
164 posts

Ryan Irelan
@ryanirelan
I teach at @craftquest_io and consult at @pineworksco. Mastodon: @[email protected]







When I started WP Engine, I thought I was pretty good at pitching. I had sold millions of dollars of software at Smart Bear, and I’d helped other companies with their pitches and fundraising. But of course it’s different when someone is trying to tear down 𝘺𝘰𝘶𝘳 idea. But then I got my first “Rude Q&A.” A VC pointed out our GPM was far too low. Another said our CAC:LTV math sounded fake. Someone else didn’t believe we could ever be differentiated. I left those meetings angry at first, but then embarrassed that I didn’t have better answers, and then motivated to get the right answers. So I started writing my own rude Q&A: • Why do I even exist when the market already has X, Y, Z? • Why should anyone 𝘣𝘦𝘭𝘪𝘦𝘷𝘦 the numbers I’m showing? • Why will that GPM improve in future; explain in detail. I forced myself to write even unfair, annoying, misinformed questions. But then then answer them--crisply, specifically, defensibly. If the answer sucked, the strategy probably did too. I either needed to get a better strategy, or be confident up-front that “Yes, that’s one of our challenges, one of the risks. Every company has risks; that’s one of ours.” This wasn’t just pitch prep. It sharpened 𝘦𝘷𝘦𝘳𝘺𝘵𝘩𝘪𝘯𝘨: • Messaging got tighter. • Positioning got clearer. • Roadmap got focused. • Confidence was earned. This isn't “embrace the suck” hustle-bro garbage. It's just the reality: You’ll get punched in the mouth. Better to swing a heavy bat before stepping to the plate. So if you’re prepping a pitch, refining messaging, or going to market--Write the questions you 𝘥𝘰𝘯’𝘵 want to hear. Don’t stop until you have great answers. More motivation and ideas in the article: longform.asmartbear.com/devils-advocat…

For software businesses that suffer from free trial abuse: We have a new @stripe API that auto predicts if your users are fraud-y or otherwise low likelihood to convert to a paid plan. (It seems ~accurate!) We'd love to test it with a few more AI and SaaS companies. Reach out.


So how reasonable is this “20–50x productivity boost” @aarondfrancis is talking about? @mattstauffer suspects the biggest gains come when AI helps prolific context-switchers move many tasks forward at once. It’s not about speed. It’s about total output.



They say AI is the end for developers. They say the job market is gone. They say learning to code is pointless. I don’t buy it. I think we're just getting started.




They say AI is the end for developers. They say the job market is gone. They say learning to code is pointless. I don’t buy it. I think we're just getting started.








