Writing
These are posts I’ve written over the years. The older ones (2011–2022) were originally published on Medium and have been brought home. New writing starts here.
- Grand Theory of AI Skepticism (In UX Research)Jul 2026
Most cynicism about AI in UX research is two years stale. Five questions I run on every confident AI take, including my own.
- Why I'm in the CodebaseJun 2026
I'm a non-engineer CEO and I've started shipping features myself. Not to relive my twenties or step on the team, but to feel every brake between 'the code works' and 'customers have it,' then write each one down with a fix.
- You Have to Touch AI PsychosisJun 2026
The consensus take is that AI psychosis is a trap to avoid. I think the consensus is wrong. AI psychosis is a stage you have to go through.
- Inject the AI straight into my veins.Jun 2026
You can learn a lot about AI from white papers and blogs. You can't learn it all that way. So we started bringing people deep in the AI weeds in to teach our team, then sending our own people out to do the same. The speaker swap, and how to run your own.
- I Vibe Coded Qualtrics in a WeekendMay 2026
What the SaaS-pocalypse gets right, what it gets wrong, and a rubric for deciding what to build, buy, or partner on.
- Seed Stage Investor Update TemplateAug 2022
Every month I write an update to our investors and advisors. I've been doing this since before Great Question was a company, before we wrote any lines of code.
- Emerging infrastructure and the entrepreneurial opportunityApr 2019
Less than 10 years ago one of the first steps in launching your web or mobile app was buying and setting up your own dedicated hardware in a back room or remote server farm.
- Your expense policy is hurting your teamMar 2019
For most companies their expense policy is an afterthought. It starts off informally.
- What the Quickbooks Accounting community can learn from GoDaddy ProFeb 2019
With QuickBooks recent testing of an integrated bookkeeping service many accountants & bookkeepers have raised valid concerns about whether the platform they promote is about to compete with them.
- Welcome Spritz — the world’s most refreshing corporate cardNov 2018
Today I'm excited to launch Spritz: the world's most refreshing corporate card. Every company in the world has expenses but no one likes doing them.
- My love affair with large, competitive, fragmented marketsAug 2018
It's easy to think all the good startup problems in B2B SAAS have already been solved.
- The Grand Theory Of Customer ValidationAug 2018
Talking to customers is a critical factor in building a successful company. It’s never more important than when you’re just getting started and still pre-product/market fit.
- There is no Show Business CommissionAug 2018
In the latest season of Comedians in Cars Getting Coffee, Alec Baldwin talks about the Show Business Commission.
- The Kanye West Work Ethic @ Rap CampOct 2017
In late 2009 Kanye West set himself up in a mansion in Hawaii to record one of the greatest albums of all times: My Beautiful Dark Twisted Fantasy.
- 19 Things I’ve DoneSep 2017
Since I was a little kid I've always looked for ways to make a buck.
- Managing your psychological runwayJun 2015
Psychological runway is the amount of time and energy you can put into a project in the face of serious challenges before you burn out and fade away.
- Seek rejectionAug 2011
I'm a massive fan of rejection. It's what keeps me moving.