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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 InsightsFailure 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
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.
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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 InsightsFailure 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
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.
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