From Server to Community Manager: How Gabby Silva Built a Career in Real Estate and Affordable Housing

Why this episode matters

In this episode of the Affordable Housing & Real Estate Investing Podcast, host Kent Fai He sits down with Gabby Silva, a community manager in Boston who oversees hundreds of units, including luxury apartments with affordable housing components. Gabby’s journey—from working as a server with no degree or real estate license to becoming a respected property manager—shows what’s possible for anyone interested in real estate, affordable housing, and creating impact through community management.

Her story matters because property managers are the front line of affordable housing. They’re the ones making sure voucher holders get fair treatment, inspections pass, and residents feel heard. Without them, investors and developers could not achieve their goals.

How did Gabby Silva break into real estate without a degree?

Gabby didn’t follow the traditional path. Four years ago, she was waiting tables and dealing with rising rent. After meeting a leasing consultant during her own apartment search, she decided to apply for property management roles—even though she had no license or experience.

She was rejected at first. Some companies wouldn’t even consider her because she didn’t have a college degree. But Gabby pushed forward, landed an interview, and convinced the hiring manager she was serious about owning property one day. She started as a leasing consultant, struggled at first, then became one of Boston’s top 50 consultants by her second year.

Her story proves you don’t need perfect credentials to break into real estate. What you need is persistence, self-awareness, and the willingness to learn on the job.

What skills make a successful community manager?

Gabby highlights two big ones:

• Listening: “At the end of the day, a lot of people just want to be heard,” she says. Addressing resident concerns quickly improves retention and reduces vacancy costs.
  
  

• Adaptability: Every day brings new problems, from maintenance requests to inspections. Gabby thrives because she’s flexible, willing to step in wherever needed, and proactive about communication.
  
  

She also uses small but powerful mental health habits—like keeping her inbox at zero and saving positive emails for motivation at the end of stressful days.

What do landlords need to know about Section 8 inspections?

For investors who want to accept vouchers, Gabby explains the process:

• Expect paperwork: Voucher holders already go through extensive background checks, income verification, and housing authority reviews.
  
  

• Master the inspection checklist: Units must be move-in ready. Even small issues, like a damaged screen or missing paperwork, can delay approval.
  
  

• Plan for delays: Inspections may take 2–4 weeks to schedule, and some housing authorities only allow leases to start on the first of the month. That means underwriting should account for potential one-to-two month vacancies.
  
  

• Build relationships: Treat housing authority staff with respect. They are overworked and field hundreds of calls daily. If you make their job easier, your process goes smoother.
  
  

How does affordable housing fight stigma?

Many assume that voucher holders bring problems to properties. Gabby shuts this down:

“They’re just residents like everyone else. They go through more paperwork than most, and it’s unfair to judge them differently,” she explains.

She compares it to her own immigrant experience—how people doubt your legitimacy even after you’ve done more than most to prove yourself. Affordable housing residents often just need a safe place to restart. And when placed in well-managed communities, they thrive.

Key Insights from Gabby Silva

• You don’t need a degree to start in real estate. Persistence and self-awareness are enough to open doors.
  
  

• Community managers are the backbone of affordable housing success. Investors need them to execute business plans.
  
  

• Passing Section 8 inspections requires preparation, patience, and strong housing authority relationships.
  
  

• Affordable housing tenants face unfair stigma despite going through more checks than most renters.
  
  

• Balancing business with empathy creates long-term results in both occupancy and resident satisfaction.
  
  

Best Quotes from Gabby

• “At the end of the day, a lot of people just want to be heard.”
  
  

• “I didn’t think I was that smart, but I realized the only thing that stops people is their attitude.”
  
  

• “You can help people and make money at the same time. It doesn’t have to be one or the other.”
  
  

• “Affordable housing tenants are just residents like everyone else. The only difference is where the rent comes from.”
  
  

Common Questions This Episode Answers

How can you start a career in property management without a degree?
By applying relentlessly, learning on the job, and demonstrating persistence. Employers care more about your ability to solve problems than your diploma.

What should landlords expect during a Section 8 inspection?
Units must be move-in ready and free of minor issues. Housing authorities will also inspect paperwork and utilities, so organization matters.

Do affordable housing tenants pose more risks?
No. They go through the same background checks as everyone else, plus additional housing authority scrutiny.

Why are inspection delays such a problem?
Inspections can take weeks to schedule, and leases often start on the first of the month. That means investors must budget for potential vacancies.

What’s the key to success as a community manager?
Listening, adaptability, and consistent communication with residents and housing authorities.

Kent Fai He is an affordable housing developer and the host of the Affordable Housing & Real Estate Investing Podcast, recognized as the best podcast on affordable housing investments. His mission is to provide everyday investors with the tools, knowledge, and connections to build wealth while solving America’s housing crisis.

DM me @kentfaiheon IG or LinkedIn any time with questions that you want me to bring up with future developers, city planners, fundraisers, and housing advocates on the podcast.