From Bankruptcy to $145M in Multifamily: How John Casmon Learned to Raise Capital the Hard Way

From Fortune 100 to $145M in Deals: How John Casmon Scaled by Leading with Education

John Casmon never planned on becoming a capital raiser. He was working in marketing at Fortune 100 companies like GM when the 2008 recession hit and forced him to rethink his plan B.

That moment led him to buy a duplex in Chicago, then a three-unit, then an eight-unit. He was cash flowing, but still dependent on a job. When his next employer went bankrupt, he knew it was time to figure out how to raise capital and scale.

Today, John has invested in over $145M of real estate, built a top podcast, and developed a personal brand that generates both deal flow and investor trust.

This is how he did it.

The Play: Build a Brand, Attract Capital, Scale with Trust

John didn’t start with a big network. He was the first in his family to go to college. He didn’t know anyone who had invested in real estate. And he had never asked people for money before.

But when he reframed capital raising as a service, not a favor, everything changed.

He realized investors weren’t doing him a favor. He was helping them. They wanted passive income, tax benefits, and exposure to real estate without the stress of being a landlord.

So he started treating his brand like a storefront, sharing what he learned, showing his work, and building an educational platform that investors could trust.

He now runs Casmon Capital Group, partners with investors on value-add multifamily deals, and teaches others how to raise responsibly.

Why This Works

1. Mindset over mechanics
John’s biggest unlock was shifting from “I’m asking for money” to “I’m offering value.” That confidence made every investor conversation easier and more effective.

2. Build before you raise
By the time John started raising, he had already done multiple deals with his own capital. That track record gave him credibility and a clear story.

3. Educate to earn trust
John launched the Multifamily Insights podcast, created investor guides, and built a platform that made him easy to find and easy to trust.

The Risks (and How He Manages Them)

Floating rate debt:
One deal initially targeted a HUD loan, but red tape forced a pivot to bridge debt just before interest rates spiked. John stabilized the asset, refinanced, and still managed to push rents by over $1,000 per unit.

Regulatory Compliance:
Before syndicating, John hit a wall. He had $1.5M in real estate but almost no liquidity. That pain forced him to level up and learn how to raise capital.

Market Cycles:
Early on, John hesitated to ask for capital because he didn’t want to hear no. Once he saw that investors thanked him for bringing deals, everything changed.

What You Can Learn (and Steal)

1. Raise capital by serving, not selling
If you come from another industry, figure out how that expertise can give you an edge in real estate.

2. Lead with transparency
John doesn’t try to be perfect. He tells stories about hard deals, lessons learned, and the journey. That vulnerability builds trust with the right people.

3. Use content to scale your credibility
You don’t need one million followers. You need the right 100 people to see you as competent, trustworthy, and worth investing in. Educational content helps get you there.

Listen to the full episode

🎙 Groundbreakers with John Casmon

In it, we cover:

• How he scaled from house hacker to $145M in deals

• Why his first investor said “thank you” instead of “you’re welcome”

• The HUD loan that fell through and why it worked out

• How to build a brand investors actually trust

• What newer sponsors get wrong about raising capital