June 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 didn’t publish any new essays (😢), but I did send out four issues of The Maine Outsider:

Maine Outsider: Invites 87, 88, 89, 90

People

I keep hearing the phrase “Maine is a small town” to describe how easy it is to meet and get connected with people in the state. I’m finding this to be true and very refreshing. So far, I’ve been able to meet with pretty much everyone I’ve reached out to. The startup scene here feels more inclusive, humble, and grounded than other communities I’ve been a part of in Austin, Boulder, and Denver.

The flipside of this small-town feel is that Maine businesses often lack connections to outside markets, investors, and media. I heard this repeatedly throughout Startup Week, especially in the context of scale-up businesses. Expanding beyond the borders of Maine can be challenging.

I’ve spent the first 10 years of my career working remotely with global peers. I’m interested in seeing how I can start pulling in some of these global connections to benefit the new friends and connections I’m making weekly.

Career

I’ve been talking with a local entrepreneur about teaming up on an automation consultancy/product studio. Basically, how do we solve bottlenecks, improve processes, and innovate to accelerate good ideas and create more work opportunities for Mainers?

It’s an exciting opportunity that meets many of my conditions for good work. It ain’t a done deal yet, so that’s all for now.

What I’m thinking about

Questions about AI

I’m very much in the “we’re not talking about AI enough camp.” I’m less interested in the conversation about AI becoming autonomous and destroying the world, and more interested in the conversation about what our jobs and lives will change in the next 5-10 years. At present, I have more questions than opinions. Here are a few:

• Is there a difference between the governance, motives, and vision for the frontier AI models (Anthropic, Meta, Grok, OpenAI)? Does it matter which ones we use and support?
• I might be able to automate and replace someone's job using AI, but should I? What if something I deem tedious and repetitive is meaningful for someone else?
• What are the ethics of AI usage and disclosure? Where is the line between work that’s augmented and work that’s AI-generated but presented as human?
• What will the world look like when we can get answers, support, and mentorship more easily from machines than people?
• Which roles/jobs are most likely to be replaced in the next 5 years, and how will those people transition into new opportunities?

Frankly, the topic is overwhelming, but I don’t think sticking my head in the sand and ignoring it is a valid option.

Update: Re-wilding the City Dump

In the last email, I talked about my pet project idea of re-wilding the city dump with wildflowers. A connection offered to introduce me to the former mayor of Portland (see… Maine is a small town), but I declined because I wanted to see how our current elected officials would respond to someone offering to help, even in a small way. I’ll try a follow-up and see where it goes.

What I’m working on

Podcast Intelligence Tool

Podcasts are rich with insights and ideas that can only happen in a conversational format. They’re far less filtered than SEO optimized blog posts or edited website content. As such, they have a wealth of potential information. This month, I finished a working prototype of a tool that allows you to search and select episodes to be filtered through AI Analysis. The process is relatively simple:

1. Define which podcast you want to analyze and select the episodes
2. Write the prompt or instructions for the LLM (ie. what do you want to look for?)
3. Run analysis and get a report

For my use case, I’m interested in mining business interviews for founders mentioning unmet needs, pain points, or market gaps that I might be able to solve through automation/product development.

It’s still in the early days, but I’m really excited by the idea. In the next few months, I’ll figure out a few use cases for monetization. For now, it’s an asset for my own research and biz dev.

If you had access to such a tool, what would you use it for? What podcasts would you analyze? And what would you want to extract?

Captures

Bookmarks

I bookmarked 75 things this month that sparked curiosity or made me pause. Here are a few that stood out:

How to Live on $432 a Month in AmericaThe accepted narrative among many people in my generation is that the American Dream is dead, and we have fewer opportunities than past generations. While extreme, this post highlights some counterpoints, mainly around lifestyle choices and creep. We have more agency in our financial situation than we would admit, when we re-think our lifestyle choices (rent, travel, consumer purchases, etc).

How to write your will in minutes but leave a forever legacy
‍I love this example of a Trojan horse business, which makes creating estate plans easy, and as a byproduct, increases the amount of donations to non-profits and charities.

Fork Food Lab Food Waste Upcycling ProgramIMO resource efficiency should be the top metric for how we measure the economy, rather than just prioritizing new goods produced. I love this local program, which takes “waste” byproducts from one food business and figures out how to remix them into a new and valuable product.

Federal RegisterDid you know the federal government is obligated by law to provide a daily update of new rules, proposed changes, and internal notices? I didn’t, and honestly, most of the internet doesn’t seem to either if you Google it. The Federal Register is essentially a daily newsletter from the government. It’s insanely long and dense, so most people don’t read it. Downloading the PDF and uploading it into a tool like Notebook LM is a useful way to learn what’s going on in the federal government on a daily basis.

How The Amazingly Burly ‘Buffalo Bicycle’ is Changing The WorldThe Buffalo Bike is designed for use in parts of Africa and other developing countries. This video from one of my favorite MTB YouTube channels breaks down the thoughtfulness behind every feature on the bike. It’s not sexy, but this is my favorite brand of design: human-centered, resourceful, and extremely pragmatic.

Florida Geoengineering TestimonyI’m not saying this will replace Love Island as your guilty pleasure, but it’s surprisingly weird, entertaining, and rich with storylines. The meeting involves a blend of politicians talking about conspiracy theories, intermingled with a young entrepreneur explaining his startup, which alters the weather and has major funding and backers. It’s probably not something you’ve thought much about, but we’re already in the age of playing god and directly manipulating the climate, in a completely non-conspiratorial way.

Federal Website IndexThe US government maintains thousands of websites across various agencies and departments. This GitHub repo outlines the process in place to ensure they are all functional, maintained, and accessible, which is a massive undertaking. I went down the rabbit hole and loaded all of the websites into an Airtable base you can view here. There are truly so many things you’d never think existed, like websites for pool safety, marine debris, and a database of dumping sites for dredged ocean material.

In Bath, students choose a hike over detentionWe’ll have to wait for the follow-up story to know the efficacy of this program, but something tells me giving students a social, active, and outdoor space to reflect on their challenges will outperform making them ruminate on their errors in a confined space.

Maine Monitor InvestigationsI’ve been on an investigative journalism kick recently. It satisfies a certain type of curiosity and storytelling for me. Investigative journalism has standalone value, but it’s also a great place for entrepreneurs to go to understand systemic issues and market gaps. This collection of reporting on key topics by the Maine Monitor is the sort of journalism I love to consume and support.

Calls to Action

Outside of showcasing my chronic distractibility, these roundups aim to clarify my thoughts and invite others into my world. If you’ve made it this far, consider one of these:

• Reply with an idea or question that emerged while reading
• Forward this to someone who might find it interesting
• Share a project or curiosity you're exploring right now