TME 49 | The Billion Dollar Capital Raising Playbook with Craig Cecilio
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Raising $1 billion in capital doesn't come from having a better deal.
It comes from building a better system.
In this episode of Raise the Bar Radio, I sit down with Craig Cecilio, founder and CEO of DiversyFund, to break down what it actually takes to raise capital at scale, and how technology, trust, investor relationships, and AI are changing the game.
Craig is a three-decade operator who has raised more than $1 billion in capital.
Through DiversyFund, he's built a real estate technology platform that has served 30,000+ investors across more than 70,000 investor transactions, with that technology now being developed into software for other real estate sponsors and operators.
You'll learn:
• What raising $1 billion taught Craig about capital raising • Why successful capital raisers are always raising capital • How AI is changing investor communications and operations • Why technology means nothing if it doesn't produce real ROI • What Craig learned building and operating Reg A+ funds • Why he's focused on Reg D in today's market • How investor behavior has changed after the last real estate cycle • Why trust matters more than the deal itself • How to identify the right investors in a difficult capital-raising environment • Why experienced operators using AI could dramatically increase their output • Where private markets, AI, tokenization, and investment technology could be heading next
One of the biggest lessons from this conversation is simple:
Investors aren't just investing in the project.
They're investing in you.
The market has changed. Many investors have been burned, trust is harder to earn, and the same capital-raising strategies that worked a few years ago may not work today.
That means knowing your investor, building real relationships, communicating consistently, and creating the infrastructure to raise capital at scale matters more than ever.
AI can make that infrastructure faster.
Technology can make it more efficient.
But trust is still what moves capital.
Links to watch and subscribe:
Seth Bradley’s Links:
X: x.com/sethbradleyesq YouTube: youtube.com/@sethbradleyesq Facebook: facebook.com/sethbradleyesq Threads: threads.com/@sethbradleyesq Instagram: instagram.com/sethbradleyesq LinkedIn: linkedin.com/in/sethbradleyesq TikTok: tiktok.com/@sethbradleyesq
Craig Cecilio's Links: Instagram: @cxcecilio Website: www.craigxcecilio.com Youtube: https://www.youtube.com/@CXCExperience/videos