100 days of AI

I've been finding myself thinking a lot about young Ryan lately. That kid who would spend hours hunched over the family Mac, figuring out how to program his first game in HyperCard. I can still feel the rush of successfully animating that crude stick figure to move across the screen - I was convinced I'd just created the next Duke Nukem. Every new discovery on that Power Mac 9500 felt like unlocking a superpower. I thought the possibilities were endless.

That same childlike excitement has returned, but this time it feels different. The endless possibilities I thought I had on that Mac were not so limitless, as it turns out. But today, with the breakthroughs in deep learning and neural networks powering this recent wave of AI tooling, it actually feels like the possibilities are truly endless. We’re not just getting new tools — we’re witnessing a fundamental shift in how humans interact with computers. That’s why I’m embarking on a 100-day journey to deeply understand AI from the ground up.

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Free-range AI agents

I can’t stop thinking about AI agents.

We’re witnessing the dawn of truly autonomous digital beings — software that not only follows instructions, but actually thinks, decides, and acts on its own. The implications are mind-blowing, and we’re just starting to get a real-world glimpse of what this future might look like.

When AI agents join forces

AI agents, or task-oriented autonomous agents, are already being deployed across industries — from customer support to healthcare — but their true potential lies not in individual tasks, but in collaboration. These digital workers can transform productivity when working alone, but the real revolution begins when they can negotiate and work together.

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The growing AI innovation gap

During a recent conference, I noticed a difference in the levels of AI tool adoption between folks at startups vs. enterprises. Startups are free to explore, and are experimenting rapidly. PMs and engineers elsewhere are struggling with stringent data restrictions, lengthy approval processes, and limited tool access. Any free exploration is left to personal time. It seems like most teams are hampered out there: according to IBM, 75% of companies face barriers to adoption. [1]

This gap isn’t just about access, it’s about the pace of innovation. 

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How to avoid overthinking your API

If you are in the business of software integrations, your API is your brand’s digital handshake with the world. How you present your API and documents directly reflects your values as a business. If you keep details clear and familiar, you'll have developers singing your praises. Overcomplicate it, and you’re basically paving the way for your competitors.

I’ve been on both sides of the equation, as a builder and customer. I’ve built and launched APIs for multi-sided marketplaces and designed large-scale operations systems automated entirely by API. I've felt the thrill of a seamless integration and the frustration of a poorly organized one. Trust me when I say this: a little added care in your API design goes a long way. It can be the factor that differentiates you from competition.

Who is this essay for? The PM or Engineering Lead who is managing / launching APIs and dealing with technical constraints, scalability, and user experience.

I get how complicated integrations can be. Your API might need multi-level schemas or intricate procedures. That complexity doesn’t have to bleed into your design and documentation. Remember why you built an API in the first place? To make your app easier to use. So let's keep things simple for your most important customer, the developer.

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Where is the AirBnb for boats?

For July 4th this year, I went out with some friends to Lake Washington. We rented a boat for a few hours, directly from this couple living right on the water. The rental experience was a delight: quick, convenient, and a price we felt great about. Having rented a boat online in a similar peer-to-peer way in 2022, I asked to see if was the same business (my friend had rented the boat) - it wasn't.

It felt similarly convenient to what I love about AirBnb: you drive up and get settled right away. For what seems like a great business, there haven't been any runaway successes yet. I thought, "What's up with that?"

Seems there are a few peer-to-peer boat rental companies, but nobody dominates. See: Boatsetter (2012), GetMyBoat (2013), Click&Boat (2013), Borrow A Boat (2014).

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YouTube's long-form legacy

My daughter is just starting to get into screens.

On a flight yesterday I put a kids video on my iPhone for her to watch - a few minutes of distraction. The screen filled with 3D dancing fruits and veggies — and she loved it.

After we landed, we put it on for a few more minutes. Those veggies started dancing and we heard the soundtrack for the first time. Where I expected obnoxious kids music, I was surprised to hear catchy dance music with guitar. The music was, dare I say… good?

YouTube creators have once again found a way to get my attention. It’s a 15 year run of getting me to stream regularly for hours. From mixes in college to branded channels in my 20s. And now in my 30s, with tasteful videos for my kids, mixed to music my wife and I can enjoy.

'Hey Bear Sensory' has found itself a niche product: bright videos, fun animations, and music that adults will tolerate. It’s brilliant.

Kids products (like this) that are built to flow with parents lives, rather than clash are going to be big winners with my generation - I’m sure of it. 

Product management at Startups vs. Enterprises


The job of a product manager is a hard one. When you are hired onto a new team, there is an expectation that you will make a positive impact in a short amount of time. Regardless of the state of a business, its size, software stack, or customer relationships - PMs are expected to come into that environment and make exceptional things happen.

Making great things happen in the face of ambiguous challenges is the job. It’s a reason why being a PM is high stress and high reward. It’s also the main reason why choosing where to work is so critical: great things don’t happen magically.

Success as a PM takes a lot of learning, collaboration, and trial & error. The company you choose to work at better have values in line with yours, otherwise you are in for a world of hurt.

Reflections on disrupting the music industry

The year is 1906. You are a sea captain, steering a ship through crashing waves and catching as much fish as possible for tomorrow’s Christmas markets. The usual beeps emanating from your shipboard radio stop, and you hear a different yet familiar sound. Excited, you run down and yell across the deck to your crew, “You gotta hear this, it’s a Christmas miracle. They’re playing ‘O Holy Night’ on the radio!”

A lot has changed about audio consumption since that Christmas eve in Boston. That was the first time music had been delivered publicly, and with it an industry was birthed. Radio gave way to vinyl, which gave way to the tape cassette, CD, and now MP3. By the early 2000s, the success of digital music pioneers Napster and iTunes proved music streaming had great potential, but monetization and copyright licensing still lagged far behind. By 2011, streaming services like Spotify, Pandora, and others were becoming some of the most recognized brands in the world — music streaming was a force to be reckoned with.

In August 2012, I joined a tech company ripe with possibility. I saw music at a crossroads between the conventions of a century’s old industry and the potential of new technology. I felt joining Dubset Media would give me an opportunity to play a part. I hoped we would get acquired, but I never imagined my work would change the music industry. That success didn’t come without its fair share of growing pains and setbacks. It’s my hope that by sharing my story, it will help you make better decisions about your team, your company strategy, and your career. This is my journey, from start to sold.

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