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

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.

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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.

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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

• Learn more about Brian and his firm at HeadwayInvestment.com

• Connect with Brian on LinkedIn

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