Your Startup Sounds Like Everyone Else Now, Thanks to AI

The Lion Lookout: Volume 16

2026 is going to be a new playing field. AI is everywhere, investors are scanning decks in seconds, and the window to make an impression has never been smaller.

The shift isn’t that founders can use AI, it’s that investors assume you already are. And they’re expecting more because of it: clarity in storytelling and a voice that doesn’t sound like it came from the same model they’re using.

For this month’s Lion Lookout, Mia and Nina sat down to unpack what they’re seeing across dozens of raises with the founders we are working with: where AI helps, where it hurts, and how founders can stay sharp in a world where both sides are using the same tools.

1. How AI Is Changing VC Expectations

More and more, the first layer of due diligence is no longer human.

Decks are scanned, summarized, scored for structure, and flagged for gaps long before a founder has a chance to step in the room.

And ironically, the rise of these automated filters has made human reviewers more skeptical, not less.

In the sea of thousands of AI-assisted materials, the bar for originality is significantly higher.

Language models can deepen a story, or flatten it into the same effort, patterns, and clinical language investors see every day.

2. How AI Affects Due Diligence

Language models tell you what they want you to hear.

When ideas aren’t fully formed, the model tries to “complete” them in ways that smooth over the same edges that make your company's story unique.

If the nuance is missing, the model amplifies the lack of nuance.

This is how founders end up in input-output echo chambers and slowly drift toward language that no longer reflects the substance of their business.

And even worse, it can nudge founders toward misinformation or unproductive parts of the build. 

3. Please Use ChatGPT


ChatGPT didn’t change what makes a great founder.

Clarity still wins.
Original thinking still wins.
Human judgment still wins.

Use the tools. Let them sharpen your logic and expand your thinking. But don’t let them erase your voice or flatten the individuality investors are trying to evaluate.

AI can accelerate everything around you, but it can’t replace the part investors ultimately bet on: you.

If you want help building materials that hold up against both the algorithms and the humans behind them, we’d love to work with you.

Interested in working with LionRun?

P.S. Email replies are on! If there are any topics you'd like to explore or questions you have, feel free to reply to this email.

Until next time, we’ll be on the lookout!