May 2025 Recap

I write these monthly recaps to slow down, digest my thoughts, and make ideas more permanent. It’s a way to invite collaboration by sharing where I’ve been and where I might be going. I’ll also continue to publish ad-hoc essays when I feel I have something to share.

Writing

This month, I published two essays and four Maine Outsider issues:

Where Ideas Live
Thinking Like a Shrimp
Maine Outsider: Invites 83, 84, 85, 86

Relationships

May was basically a meet-and-greet tour with 16 scheduled meetings and plenty of spontaneous chats during Maine Startup Week. I connected with a National Geographic Explorer, a brewery owner, a VC, and several entrepreneurs.

About half the meetings I directly set up, and the other half found me. I’m an introvert, but I find one-on-one conversations energizing, especially in-person ones, which I didn’t have for a long time while working remotely.

Career

I’ve applied to two full-time jobs and haven’t heard back from either, despite being qualified and, in one case, personally knowing the hiring contact 🤷‍♂️. I’m not too bothered. Most companies have horrific hiring practices. The economic uncertainty probably isn’t helping either.

I’ll keep looking for entrepreneurial support or innovation roles, but it’s not my primary focus. Life seems to be pulling me back toward consulting, entrepreneurship, and project-based work. I’ve had co-founder meetings, consulting requests, and positive feedback on an AI-enabled research product I’m building.

This blended model of work probably suits me better. It lets me be curious, hacky, and resourceful—my best traits. If needed, I can pitch myself as a Webflow Developer, AI Ops Consultant, Airtable Developer, rapid app builder, or fractional product/project manager to extend my runway as I continue exploring.

What I’m thinking about

My Brand of Curiosity

In 2018, I pitched myself as a “curiosity consultant” for data science boot camps. The idea was that organizations don’t teach people how to ask better questions or nurture curiosity. It was fringe back then.

This week, I talked to someone who does exactly that. Her name is Hannah, and she’s Head of Creative Questions at Now What. Through hundreds of conversations, they built a curiosity style assessment and a method for cultivating curiosity in organizations. You can watch their SXSW presentation for context.

Here are my results from the assessment:
Inner Child: 8
Rebel: 32
Tinkerer: 58
Voyager: 62

I take assessments with a grain of salt, but these results feel spot on. The Voyager approaches curiosity like a map, methodically exploring to gather extensive information, seeking to understand the full picture, and connecting diverse dots to find solutions. The tinkerer approaches curiosity like a puzzle, experimenting to solve problems and improve things.

These results align with my own personal assessment from 3+ months ago — range widely, connect dots, and use technology to do it.

I’m still trying to answer the question: what the hell do I do with this insatiable curiosity? But I think I’m getting closer.

Maine’s Entrepreneurship Ecosystem

I attended Maine Startup Week as an unemployed guy with a sense of curiosity. As such, I didn’t show up needing to pitch anything or represent an organization. Here are a few notes I took down on my phone:

• Good panels need good questions. Good inputs = good outputs.
• Entrepreneurship isn’t a neat pipeline (idea → MVP → pitch → raise). Most founders stumble into unexpected needs. You have to stay in the game and be open and observant to catch them.
• Maine has a high ratio of resources to entrepreneurs. It’s a great place to go from 0 to 1.
• Specificity wins. CEI stood out on the climate change panel because they identified home weatherization as a specific opportunity and built an accelerator around it. It’s specific and rooted in place. In the innovation/entrepreneurship world, we often fail to be specific enough when focusing on what we’re solving.

Digital Inefficiency

It’s easy to forget that everything on the internet runs on real-world resources, like energy and minerals. Every file we store, every message we send, has an earthly cost.

I’ve been thinking about this more lately, especially as AI agents get better at browsing and automating tasks. A huge chunk of web traffic is already bots, crawlers, and scripts. AI will only add to the noise.

Check out this ChatGPT exchange I had if you want to see where my head is at. In short, I’m worried AI could accelerate an already inefficient web.

Re-Wilding the Old City Landfill

I often pass the old city landfill on my afternoon mountain bike rides. It’s a massive open space covered with solar panels on the south side and what looks like a single species of grass. From my observations, it’s mowed maybe once or twice a year.

It’s always struck me as a wasted chance to increase biodiversity. I even emailed a contact from the city last year but never heard back.

I saw an article this week about Staten Island converting the world’s largest retired landfill into a habitat with 50,000 flowers. I’m re-inspired to give it another run. Working on a project like this with such tangible and visible benefits sounds fun.

What I’m working on

Discovery as a Service

I hinted at it earlier, but I’m drawn to building “Tools for Discovery.” That feeling of discovery drives almost everything I do. I love learning, experimenting, and seeing how technology can make it all more accessible.

The landscape for tech-enabled discovery is wide open, especially with the advances in LLMs. I have many ideas, but the one I keep coming back to is using AI to surface entrepreneurship opportunities. The idea is to feed problem-rich content into an AI trained to think like an entrepreneur and then evaluate the outputs.

Innovation has many flavors, but one simple model is to find businesses or groups of people with a clear need and work to solve it. My thesis is that doing this in a more structured, repeatable way could spark more entrepreneurship. I wrote about this in my Thinking Like A Shrimp post:

1. Get close to a problem
2. Get close to the customer
3. Get Started

I want to use my skills to build better entry points for entrepreneurs in Maine (and beyond) by mining existing conversations for B2B business opportunities. Maybe my LinkedIn title will eventually just say “Opportunity Broker.” I have a proof of concept, but a few details still need work.

Slack Matchmaking Program

I expanded on some volunteer work with a local startup community by creating an automated matchmaking program for the ~1,000 members in their Slack. Off-the-shelf solutions start at $200 a month, so I built a free version using Slackbots and Airtable. It’s simple enough that any community volunteer can run it.

The system tracks who’s enrolled each month, pairs them randomly (no duplicate matches), and generates a message ready to paste into Slack to announce the matches.

This is how I’m wired: drop me into a space, let me ask questions, and I’ll tinker my way to a solution.

Maine Outsider Improvements

I’m intentionally DIY about my outdoor newsletter because I want it always to be fun and an escape from my strategic mind. But sometimes, I can’t resist a few upgrades. I keep a list of small friction points and reader experience tweaks, and when I have time or feel inspired, I tackle them.

This week, I built an automation that pulls stats for each email—open rates, click-throughs, and more. So far, 20,824 of 27,230 emails have been opened (77.5%), with 5,764 clicks to external events and organizations. That confirms I’m hitting the goal: create something worth opening that connects readers to local outdoor orgs.

Captures

Bookmarks

I bookmarked 46 things this month that sparked curiosity or made me pause. Here are a few that stood out:

Baratunde Thurston - From Me to We, A Story of Interdependence
I’ve been a big fan of Baratunde since watching America Outdoors on PBS (cue grandpa jokes). This keynote got me, especially when he describes a community re-burying their ancestors because of sea-level rise. I love his framing of citizenship as a verb. His storytelling, wordplay, and timing are also top-notch.

Path to Philosophy
There’s an internet theory that clicking links on Wikipedia eventually leads you to philosophy. In other words, human thought keeps circling back to big questions. This little tool calculates how many clicks it takes to get there.

Night Science Podcast
The Night Science podcast asks, “Where do ideas come from?” They describe day science as the structured process of hypotheses, lab work, and peer review. Night science is the messy, unplanned thinking that happens outside that framework. It explores where questions come from, what is interesting, and what is worth exploring.

I usually stick to tech and business, but I’ve enjoyed stepping into the worlds of scientists and researchers.

Fish Wife - Tinned Fish
I don’t know why, but I have a running bit with Renee where I proclaim that tinned fish is the next big thing. Maybe it is, maybe it isn’t. The emergence of a beautifully designed brand founded by a team of young female entrepreneurs feels like a signal in my favor. I love the design of this brand and the idea of young people breathing new life into old industries.

Manu Prakash - Finding Sublime in the Mundane
I’m always looking for role models who embody curiosity and have built careers in open-ended spaces. Manu's philosophy of frugal science resonates with me, including his belief that the mundane is full of ideas.

I often feel, in science, we are attracted to the exotic. But sometimes curiosity drives you to the mundane… I like the mundane, because I think when you uncover a layer in the mundane and you find something quite puzzling, that tells you that we actually don't understand the mundane.

The Sound of Love
There’s art everywhere on the internet if you know where to look. This project extracts heartfelt or insightful YouTube comments and overlays them on the tracks where they were posted. The internet can feel noisy and aggressive, but places with depth and emotion still exist.