Evaluating Sponsors Through Distress and Transparency

Jeremy details how investors should assess operators by their transparency and response during distressed market conditions.

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Episode notes

Most people raising capital are doing it completely wrong. They focus on flashy decks, mass emails, and trying to “look big”—but investors can smell the inauthenticity from a mile away.

Jeremy Dyer took a different approach. He raised $50M in under 2 years by leading with trust, transparency, and one-on-one conversations—all while holding down a full-time tech sales job and raising four kids.

In this episode, Michael Blank uncovers the real strategies behind Jeremy’s rise from passive investor to powerhouse capital raiser. You’ll learn how he built a loyal investor base, scaled legally with fund-to-fund models, and is now buying deals at massive discounts while others sit on the sidelines. If you think capital raising is about money—it’s not. It’s about people.

Head over to https://thefreedompodcast.com/500 to submit for a chance to win free merch and be highlighted in episode 500!!!

Key Takeaways

Why LP Experience Makes You a Better Syndicator

Jeremy invested in over 40 syndications before ever raising a dollar.
Seeing wins and losses helped him understand what real investors care about.
He built empathy—and that changed everything.

Capital Raising is Human, Not Corporate

His $50M didn’t come from ads—it came from deep personal conversations.
Jeremy rebranded himself organically, one investor at a time.
Sales background helped, but being authentic mattered more.

How to Stand Out in a Sea of Noise

He personally checks in with 20 investors every week.
Following up on personal details (like a kid’s birthday) beats “just checking in” emails.
Raising capital is about trust—not timing.

The Right Way to Raise Capital for Others