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If you guess the location correctly I’ll give you a free month of this newsletter’s paid tier!

Lately, I’ve been thinking about how connection compounds — especially when it happens in person.

After years of virtual meetings and digital everything, the feedback has been clear: people miss being together. The energy, the ideas, the serendipity — it just hits different when you are in the same room.

But first, an important piece of advice for founders deep in the throes of pitching. Read on to avoid these common fundraising pitfalls.

🚩 3 Common Red Flags I See From Founders

I’ve reviewed thousands of decks and worked with some of the biggest brands in the world. And yet, I could shout “storytelling” from the rooftops, and most teams still would not get it.

Founders often spend weeks perfecting their pitch deck design, tweaking product screenshots, or memorizing TAM/SAM/SOM numbers—but miss the single thing that truly moves investors: clarity.

Clarity of story. Clarity of purpose. Clarity of vision.

The irony is that early-stage investors are not just betting on what you are building—they are betting on you. Your ability to communicate why this company should exist, why now, and why you are the person to build it is what gets people to lean in.

To help early-stage founders avoid the same pitfalls, here are three of the biggest red flags I see over and over again—and how to fix them.

1️⃣ Rushed timelines.

Somewhere along the way, “create urgency” became startup gospel. But when a founder says, “we’re closing the round in a week,” I almost always pass.

Not because I do not believe in the business, but because conviction takes time. Real diligence—customer references, market validation, founder references—cannot happen in days. Venture capital is a long-term relationship business, and compressed timelines often signal misalignment or desperation rather than momentum.

If you want serious investors at the table, give them space to build conviction.

2️⃣ Lack of coachability.

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