You curious caracal, you...

You did it, you found me!

You scanned the QR code. Whether you found it on a business card, at an event, or somewhere unexpected — welcome. 

Connect with Skipper:

Next section

More than a soundtrack

Our winter mixtape starts with a novelty song so full of confidence it shouldn't open anything — and ends with Daughter sitting with the hangover of oversharing for nearly seven min. That's the range.

It's true, Sofia Coppola's on-set playlists for "Priscilla" were the unlikely starting point (here and here). No Elvis, which makes sense given it's Priscilla's story. We borrowed a few songs directly from her list — Shuggie Otis and Porches — and built around the question, what does it sound like to hold something?

First, '60s girl groups articulating heartbreak. Then, Otis Redding being Otis Redding. Marlena Shaw asking if it's 1969 or 2026. A lazy California soul afternoon that suddenly has politics. Oh, and the shoegaze — totally different time and space shoehorned in, not far from where Coppola went with Cocteau Twins.

It ends like a dinner with dear friends where the plates have been cleared, then Daughter comes back twice to close it out.

That's what late winter feels like for us. A lot of holding, a lot of tension. 33 tracks, a bit over two hours.

While the playlist is embedded from Apple Music, you can also find it on Spotify with a few licensing differences.

-

Previous installments:

Services

How we help B2B teams move from intuition to evidence

Icon representing iterative product strategy loops

Product strategy & design

Create products customers want using tested methods that turn insights into business results

Icon of a strategy clipboard

Workshop facilitation

Turn ideas into action through focused sessions — from our signature Bullseye Customer Sprint to a Listening Cycle to a Design Sprint 2.0

Icon of three hearts

Team development & coaching

Build stronger teams that solve problems together through structured coaching and proven frameworks

Perspective from other humans I've worked with

"His calm, collected demeanor and thoughtful approach have profoundly shaped my problem-solving and client interactions. Skipper's mentorship is transformative."

Brian Heltsmith, senior product designer

"Skipper listens to his customers, leveraging their insights to initiate ideation and innovation. His ability to distill complexity into simple, elegant solutions is remarkable."

Marley Sirman, account executive

"Skipper brings a human-centric approach to transformational change for clients, with a rare ability to empathize with diverse perspectives, leading to solutions that genuinely work for all."

Gerard Welikala, vice president of digital transformation

"Working with Skipper at Replay.io, I saw firsthand how he cuts through the noise when a team is stuck between a product they believe in and a customer they haven't quite found yet. He has a rare talent for helping teams identify their bullseye customer — and making that clarity stick across the whole team, not just leadership."

Filip Hric, developer relations manager

"Skipper excels as a workshop facilitator, guiding teams through structured and highly productive sessions. His ability to unite remote teams and foster collaboration makes him a remarkable leader."

Snizhana Bezhnar, design director

This is a no pitch zone

Tell us where you're at

We'll talk through your situation and be straight about whether our approach makes sense for you and your team

Book a 25-min call
How This Works co — Evidence-based strategy for B2B teams

Based in San Francisco, CA, working globally

Subscribe to our newsletter, How Might We...

Weekly-ish dispatches on customer discovery and product strategy — sensemaking from inside the work and from home, with AI in the mix

© 2026 How This Works, Inc. All rights reserved.

A hidden cassette tape angled easter egg linking to the How This Works co contact page