Kyle Frost

I'm a product design leader working at the intersection of design and AI.

I'm currently leading product design at PermitFlow, where we're improving the annoyingly complex system of construction permitting in North America.

My newsletter Here & There  has 60k subscribers and covers deeply researched topics in travel, adventure, and outdoor culture.

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Posts

Just a few thoughts on design, tech, startups, and AI. If you're looking for more of my outdoor/travel deep dives, check out Here & There.

Sometimes It's the Small Stuff

The collapse of roles

I used AI to fix my Chrome bookmarks

How I use ChatGPT to save time and effort writing changelogs

These landscapes aren't real.

Twitter's blue checkmark and the power of mental models

The problems with Outside's "Outerverse"

Web3 + the outdoors – it's not all bad but sometimes it feels gross.

The collapse of roles

AI is not just accelerating work but fundamentally reshaping who does it, how they do it, and what it means to belong on a team.

I used AI to fix my Chrome bookmarks

I built a smarter bookmark tool that auto-sorts links using GPT-4 — no tags, no folders, just one click.

Sometimes It's the Small Stuff

A reminder that design isn’t always about big launches. It’s about small, smart steps that actually work.

These landscapes aren't real.

An exploration in generative AI photography and what it means for the the industry

Twitter's blue checkmark and the power of mental models

Let's break down the designer-y explanation for why the changing how the blue check works feels so weird and confusing.

The problems with Outside's "Outerverse"

Outside Interactive dips into the world of web3 with a new initiative called Outside.io.

Web3 + the outdoors – it's not all bad but sometimes it feels gross.

I stumbled across an outdoors-focused NFT collection. I'm feeling conflicted.

How I use ChatGPT to save time and effort writing changelogs

An AI-powered changelog workflow helps our small team stay in sync without adding tools, meetings, or overhead.