I'm Skipper, facilitating better product strategy & design work at How This Works co
sales
+9
Sep 23, 2026
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3 min read
Over 30 founders asked me two different questions over the last month, underneath both was the same one, How do I find paying customers?
startups
+8
Jun 19, 2026
The most consequential decision in the whole process of building a startup — and the one most founders treat like an ops problem
+6
Jun 1, 2026
Filling in the blanks is the easy part
facilitation
+10
May 21, 2026
The difference between a customer you describe generally and one you can actually find, breaking down the one-liner itself
tense
May 12, 2026
The answer to the future lives in what your customer has already tried
+7
May 4, 2026
Sales down 23% over 18 months — not for lack of customer contact, but for lack of the right kind of contact
Apr 27, 2026
4 min read
The moment you pitch, most conversations are over
Apr 18, 2026
2 min read
On echo chambers and the 1-pager I should have updated a year ago
product-market fit
+5
Mar 29, 2026
7 min read
On coming back, a domain detour, and the detective agency I never opened, but kinda did
bullseye customers
+4
Dec 22, 2025
8 min read
Two (2) months for 15 minutes of fame
AI
Dec 1, 2025
9 min read
When your data tells you one story and humans tell you another
Nov 24, 2025
AI is inevitably part of the conversation, here's what I've learned about when it actually helps — and when to trust your gut instead
Nov 10, 2025
Why the timeline isn't about speed — it's about limiting how much you can invest in being wrong
Oct 27, 2025
11 min read
Using Redact and Claude to systematically extract insights without drowning in hours of transcripts
How might we
Oct 21, 2025
Why the way you frame questions to AI determines whether you're thinking or just following instructions
fishing
Oct 14, 2025
Sometimes you have to hold something to feel it, to understand it
Oct 6, 2025
The gap between what you're building and who actually needs and wants it
Sep 28, 2025
People often ask me what's different between a bullseye customer interview and a user interview
brain science
Sep 24, 2025
6 min read
The cognitive research that changed how I think about collaboration
Sep 23, 2025
5 min read
Starting How This Works co taught me meetings are really just design problems
Sesame
+1
Sep 22, 2025
What we learned bribing strangers to look at our half-built product
Innovation
Sep 21, 2025
What his story can teach us about focus when markets barely exist
customer interviews
Sep 11, 2025
Why subject matter expertise and market research isn't the same as customer insights
Sep 8, 2025
But the reality is that they haven't talked to one in weeks or months — if ever
TIL
+3
Sep 7, 2025
What it teaches us about truth, positioning, and the history of innovation
