Ep 49: Raising $11M in 90 Minutes: How Reilly Brennan & Team grew from $3M to $330M

All Episodes

April 30, 2025 • 46 mins

In this conversation, Reilly Brennan shares his remarkable journey of scaling a real estate portfolio from $3 million to $330 million in just three years. He discusses the strategies employed, the importance of building strong relationships with investors, and the dynamics of assembling a diverse and effective team. The conversation also highlights the significance of continuous improvement and the application of innovative practices in real estate management. In this conversation, Gideon and Reilly Brennan explore the significance of incremental improvements in business, particularly in the context of real estate and hospitality. They discuss the application of lessons learned from previous ventures to new projects, emphasizing the importance of understanding customer needs and creating value.

*Reilly mentioned raising $30M in 90 min in the episode but later mentioned it was $11M in 90 min - still absolutely insane, but he wanted to be sure we corrected it.*

Takeaways

Reilly scaled a real estate portfolio from $3M to $330M in three years.
Building strong relationships with investors is crucial for capital raising.
The importance of understanding investors' personal goals and needs.
A diverse team with varied skill sets enhances operational efficiency.
Continuous improvement through small, incremental changes can lead to significant results.
Location is a critical factor in real estate investment success.
Effective property management can significantly increase profit margins.
Utilizing systems for repetitive tasks streamlines operations.
Engaging investors through transparency builds trust and enthusiasm.
The right team dynamics can accelerate growth and innovation. They started doing special physical therapy for muscle recovery.
They painted the inside of all their vans and office spaces white.
They were obsessive about the 1% rather than the big gains.
If you can't find something that gives you a 10% improvement, look for 10 things that will give you a 1% improvement.
We bought a small nine unit boutique hotel on Lake Superior.
We're doing just under a million dollar renovation on a 22 unit hotel.
Identifying a niche is crucial for attracting guests.
We want to lead with revenue and see what sticks.
The power of asking for opportunities is immense.
It's important to align incentives with team members.

Sound Bites

"$11 million in 90 minutes!"

"We want to be the best in everything we do."
"How do we make a 10% improvement?"
"Obsessive about the 1% rather than the 10%"
"We bought a small nine unit boutique hotel"
"Building for outdoor enthusiasts is key"
"We want to lead with revenue"
"What are the things that I'm not good at?"
"I'd rather own a big pie with rock stars"

Chapters