From building his first single-family portfolio in 2006 to acquiring over $700M in multifamily and single-family assets, Mathew Simmons shares how relentless focus, adaptability, and disciplined strategy shaped his journey to the top of real estate private equity.

In this episode, Mathew—founder and CEO of Sim Capital—dives into the evolution of his firm’s growth from small personal rentals to multi-asset funds exceeding $100M each. He unpacks the pros and cons of multi-asset versus single-asset syndications, how disciplined underwriting and conservative leverage protected his firm during volatile markets, and why he launched a thriving affordable housing fund during the downturn. Whether you’re an aspiring syndicator or seasoned investor, this conversation reveals a masterclass in scaling strategically, raising capital efficiently, and leading with vision through every cycle
5 Key Takeaways

1. From Single Family to Multifamily Mastery — Mathew explains how his journey evolved from small rentals to large-scale multifamily deals, fueled by lessons learned in affordable housing
   
2. The Power of Multi-Asset Funds — He breaks down why Sim Capital prefers diversified multi-asset structures for scalability and stability across markets
   
3. Raising Capital Through Trust — Mathew shares how building relationships and transparency helped him grow from $5M raises to $50M+ funds
   
4. Pivoting During Market Shifts — Instead of chasing overpriced assets during 2020–2022, his team focused on operational efficiency and launched a high-performing affordable housing fund
   
5. Mindset of Relentless Growth — Mathew reveals his internal drive for continuous progress and problem-solving, emphasizing that success in real estate comes from discipline, resilience, and never settling for “good enough”

About Tim Mai
Tim Mai is a real estate investor, fund manager, mentor, and founder of HERO Mastermind for REI coaches.
He has helped many real estate investors and coaches become millionaires. Tim continues to help busy professionals earn income and build wealth through passive investing.
He is also a creative marketer and promoter with incredible knowledge and experience, which he freely shares.
He has lifted himself from the aftermath of war, achieving technical expertise in computers, followed by investment success in real estate, management skills, and a lofty position among real estate educators and internet marketers.
Tim is an industry leader who has acquired and exited well over $50 million worth of real estate and is currently an investor in over 2700 units of multifamily apartments.
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