Top Questions Investors Should Ask with Brian Alfaro, Ep. 702
0 Comments

Written by John Casmon

April 8, 2025

Brian Alfaro is the Director of Investor Relations at Headway Capital, a Houston-based private equity firm managing over $500 million in assets. With a background in the restaurant industry, Brian transitioned into real estate in 2017, starting in single-family investing before moving into multifamily. Today, he specializes in building investor relationships and raising capital for large-scale multifamily projects.

Get ready for REWBCON 2025, happening from April 10th to 12th! Use my code JOHN at checkout for 10% off your ticket.

Key Takeaways:

  • Transitioned from single-family to multifamily investing after realizing the scale and sophistication better aligned with his goals.
  • Investor relations is a long-term game focused on education, trust-building, and communication.
  • Effective capital raising is more about listening to investor needs than pushing returns.
  • Investors should ask more questions about risk, not just returns.
  • Strong communication and transparency are crucial when working with passive investors.

Topics:

From Restaurants to Real Estate

  • 17-year background in restaurant operations before entering real estate in 2017.
  • Started with the BRRRR strategy, but found single-family investing misaligned with his personality and long-term vision.

Making the Jump to Multifamily

  • Joined a multifamily mentorship in 2020 to scale smarter.
  • Chose capital raising as his focus area, learning to nurture and educate investors.

Why Multifamily Made More Sense

  • Single-family was labor-intensive with low cash flow margins.
  • Multifamily offered more scalability, better team collaboration, and higher ROI potential.
  • Appreciated the abundance mindset and collaboration in multifamily circles compared to the scarcity mindset in single-family spaces.

Investor Relations Demystified

  • Focused on helping investors feel confident and informed through steady communication and trust-building.
  • Building “know, like, trust” takes time—rarely an overnight process.
  • Education-first mindset; avoids industry jargon to reduce confusion.

Top Questions LPs Should Be Asking

  • Investors often ask about returns but rarely probe into risks or past challenges.
  • Brian encourages asking about capital calls, past losses, and how operators handled them.
  • Transparency and accountability are key indicators of a trustworthy sponsor.

Mistakes New Capital Raisers Make

  • Being too transactional or too numbers-focused instead of building genuine relationships.
  • Failing to understand investor goals—listening is more powerful than selling.
  • Good investor relations = solving problems, not pitching products.

📢 Announcement: Learn about our Apartment Investing Mastermind here.

Round of Insights

Failure that led to success: Losing $5,000 on a non-refundable earnest money deposit in his first wholesale deal taught Brian to take calculated risks and commit when the fundamentals check out.

Digital or mobile resource: LinkedIn is a powerful platform for networking and staying up to date in the multifamily space. It’s where Brian builds and nurtures investor relationships daily.

Book recommendation: The 7 Habits of Highly Effective People by Stephen Covey – a foundational book Brian rereads to stay focused, grounded, and growth-minded.

Daily habit: Working out is Brian’s way to reset and stay mentally sharp—especially helpful as a new dad balancing entrepreneurship and family life.

#1 insight for being effective in investor relations: Be an active listener. Don’t listen just to respond—listen to understand and guide the investor accordingly.

Favorite restaurant in Houston, TX: Mala Sichuan Bistro.

Next Steps

Thank you for joining us for another great episode! If you’re enjoying the show, please LEAVE A RATING OR REVIEW, and be sure to hit that subscribe button so you do not miss an episode.