In this episode, Dan Deppen breaks down the biggest takeaways from the 2026 Squad Up Summit—one of the largest real estate investing conferences in the country. With over 2,700 attendees and insights from top entrepreneurs, this recap covers what's actually working right now in creative finance and real estate investing.

You'll learn how investors are adapting to changing market conditions, where new opportunities are emerging, and how tools like AI are beginning to transform underwriting, operations, and deal flow.

Dan also shares real-world insights from his own business, including scaling Call The Underwriter, buying notes, and evaluating new opportunities like tax overages.

What You'll Learn:

How to adapt your investing strategy to shifting market conditions
The rise of AI agents in real estate and underwriting
Why non-QM lending and seller finance are growing
What tax overages are and how investors are monetizing them
Key business principles: lead generation, underwriting, funding, management, and scaling
Hiring lessons and how to avoid costly team mistakes
Why some strategies (like Airbnb) are struggling—and what's replacing them

Timestamps:

00:00 – Intro & overview of Squad Up Summit 02:00 – Key speakers and major themes 04:00 – AI in real estate (agents, automation, bookkeeping) 07:00 – Building scalable systems (including CTU chatbot) 08:30 – Tax overages explained (real example) 14:00 – Emerging strategies: RV parks, co-living, affordability 15:00 – The 5-step framework for building a real estate business 17:00 – Adapting to market conditions (non-QM, seller finance) 18:30 – Investor mindset mistakes (self-imposed limits) 20:00 – Hiring and scaling lessons 22:00 – Final takeaways & current deals

Call The Underwriter