I recently had the chance to contribute to a thoughtful and timely piece by my good friend and podcast co-host, Halle Tecco. After 15 years and 53 angel investments, Halle hit pause and pulled back the curtain on what her portfolio actually looks like. What followed was a candid conversation about the evolving realities of startup investing.

My partner, Aaron Ginsburg, and I shared what we’re seeing on the legal side.

The short version? The angel investing game has absolutely changed. But it’s far from over. We’re just in a new chapter - one that requires more discipline, more intentionality, and deeper relationships.

Here’s a section I keep coming back to:

“There’s still a ton of opportunity out there—especially for angels who focus on good operators, trusted referral networks, and experienced co-investors. The bar is just higher now, and the path to success looks different than it did in the 2010s.”

Aaron and I have seen this firsthand: founders are raising with sharper terms, and later-stage investors are pushing harder for downside protection. That has real consequences, especially for early believers who backed companies before they had traction, product, or revenue.

But angels aren’t powerless. In the piece, we walk through:

• Why SAFE structures—while efficient—can leave early investors without a seat at the table later on
• What recaps actually mean in practice (and how they can squeeze out early investors)
• The practical protections angels can ask for—like pro rata, info rights, or soft veto power—especially when paired with strong founder relationships
• Why founders who care about their early supporters need to think beyond the current round

We’re not sounding the alarm. We’re saying: the playbook is evolving. The best angels today are leaning in, staying close to founders, asking smart questions, and co-investing with folks who’ve been through a few cycles.

Grateful to Halle for starting the conversation—and for being willing to share her own journey so candidly.

👉 Read the full post here: “😩 It's not just me, startup investing HAS changed”