4 Year Vesting Is Not Enough

And why you should build your product around "triggers"

Hey y’all — here’s today at a glance:

Opportunity → Social Media AI Content Detector

Framework → Triggers, Constraints, and Rituals

Tool → Helper

Trend → Health & Wellness

Quote → 4 Years Is Not Enough

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🔗 Houck’s Picks

My favorite finds of the week.


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💡 Opportunity: Social Media AI Content Detector

Your inbox has a spam filter on it, but what about your social media diet?

Probably not, unless you’re trigger-happy on the block feature.

But maybe you should.

In fact, maybe it should be a lot smarter than a spam filter.

There’s a ton of noise on social media, and algorithms aren’t perfect — good content often doesn’t get enough attention (which is why I built Megaphone) and a lot of bad content makes it onto your For You feed.

An agent that learned my preferences across all apps, as well as one that had context about what I was currently working on, could ensure only high-signal content gets shown to me.

Imagine a superintelligent Twitter/X or TikTok skin.

Would you pay for that? I would.

🧠 Framework: Triggers, Constraints, and Rituals

Start thinking about your product in terms of where triggers, constraints, and user rituals exist within it.

The rise of AI means that more user experiences within the best products will be trigger-based, rather than static. And wide open experiences will be less desirable than opinionated, constrained ones.

I love this quick framework from Greg Isenberg. It’s the new strategy for thinking about how to keep users engaged with your product.

I’d recommend exploring it now, because soon it’ll be expected — get out in front of it.

🛠 Tool: Helper

I love simple tools. Things that have their one job, and do it well.

Helper is one of those.

It lets you teach an AI agent how to answer your customers’ questions. That’s it!

But the UX is super intuitive and it’s built by Gumroad’s founder, Sahil Lavingia, so there’s a solid amount of trust in the product.

In fact, I’m in the process of setting it up for Megaphone to see how it works.

📈 Trend: Health and Wellness

The health industry doesn’t just mean medicine and exercise anymore.

There’s an increasing share of attention and capital being poured into the space, particular in areas that used to be considered “new age” that have been rebranded and repacked as “wellness.”

💬 Quote: 4 Years Is Not Enough

When you give equity grants, a 4 year vesting term with equal monthly grants and a 1 year cliff is standard.

Some companies, like Amazon, go rogue from this:

…but the vast majority of startups use the standard.

This is true even for founders.

At my last company, I had vested for ~2.5 years (~60%+ of my equity grant) before I left.

But is this actually the right structure for founders, specifically?

There’s a strong case to be made that a more founder-friendly option is actually a longer vesting period.

That sounds counterintuitive but Jack Altman makes good and pragmatic argument:

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