Startups in Legal Grey Areas

And a way to bring back second-brains with AI

On Saturday I shared a deep dive on how to build a cult with your startup. Join the community to get access to my library of 50+ deep dives, and a new one in your inbox each Saturday.

Today at a glance:

  • Opportunity → Ego Media

  • Framework → A-B-Z

  • Tool → Deel

  • Trend → Kindle Direct Publishing

  • Quote → The Fine Line of Legality

💡 Opportunity: AI Personal Interface

A few years ago when Roam Research was rising in popularity and the idea of manually recording connections between all of your thoughts, notes, and more seemed appealing to people Nat Eliason helped popularize the idea of building a second brain.

Since then, as people have realized what a daunting and lifetime-long task maintaining a zettlekasten network of their thoughts really is, the idea has fallen out of favor a bit.

But intelligent categorization is something LLMs are quite good at. And having the finished-product of a zettlekasten-style database that’s easily accessible is actually a pretty good idea.

Maybe Roam, Athens, and Obsidian were just too early:

Hundreds per month is probably more than most people would pay, but I do think there’s a fun venture-scale startup idea here.

Here’s how it would work:

  1. Decide which data sources you want to integrate. This could include email, calendar, your note-taking app of choice, your social media accounts, and more.

  2. The app ingests all of your data from each source.

  3. You can query the app through natural-language about any topic you’ve previously written down a thought about.

Sort of like but without the fact that they record your screen constantly. Or like but focused on being an assistant to yourself rather than a publicly available version of you.

You could add a premium tier that:

  • Also ingests publicly-available sources (all articles from a publication, all papers on a specific topic on arXiv, etc.)

  • Writes email and social media posts for you. Other options on the market train based on a limited set of your information (and the output tends to be generic). This would be trained specifically all of your previous thoughts.

  • Recommends insights, articles, even thoughts from other people who use the service

If done right, churn would be incredibly low due to the compounding value of the service.

🧠 Framework: A-B-Z

How can you avoid the trap of doing too much analysis before making progress on something new?

The secret may be realizing just how far whatever you do now is from your end vision. The A-B-Z framework can help.

By acknowledging how far you are from your end goal you can:

  • Recognize you have room and time to change anything you do right now

  • Reduce the pressure of getting things right immediately

  • Realize that the only way to get there is to take one step in that direction

What I like about this is that you can use it at any step in your journey, since “A” is just wherever you’re at right now:

🛠 Tool: Deel

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📈 Trend: Kindle Direct Publishing

Everyone’s trying to cut out middlemen. Authors are no exception.

Search interest for “KDP” or Kindle Direct Publishing has been steadily growing for years. KDP allows authors to self-publish in digital and print directly on Amazon rather than rely on a traditional publisher and Amazon pays over $520M million in royalties to more than a million self-publishing authors every year.

Upgrade to see new ways to capitalize on the trend of the week, like this one:

💬 Quote: Grey Area Startups

I’ll probably take some flack for this, but operating in legal grey areas with your startup is a competitive advantage.

Jared from YC explains why:

When you aren’t a known brand yet, the risk of action being taken against you is much lower. How much you lean into this risk, and where the line is for you, is a personal decision.

But many successful companies flirt with the line often — I saw this first hand working at Uber, Airbnb, and my own startup. When we were running coliving houses, we were conscious of local occupancy laws and prepared strong arguments upfront for why our setups were legal in case we ever needed them.

A big learning is that, in many cases, the law is less black and white than you’re led to believe.

🔗 Houck’s Picks

  • This 5-day leadership email course will transform you into the leader everyone wants to follow (Link)*

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Upgrade for the full batch of picks this week:

  • How to find and win your first 10 B2B customers

  • The best traits in a founder

  • How to take advice as a leader

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