Why $300 a Month Can Change Your Entire Portfolio?

Ray Glimp went from living in a New York City homeless shelter to owning over 100 rental units. His success is built on a foundation of purpose, persistence, and a desire to give back. Today he is a full-time real estate investor, award-winning coach, and affordable housing advocate featured on Yahoo and Google. He is a 40 Under 40 candidate and NAACP Champion of Change.

Here is a preview of what we discussed in this interview:

• How to get started in real estate even when you have nothing

• Why you must master all investing strategies even if you use only one

• Why small wins (even just $300 a month) can change the trajectory of your life

• How to invest in affordable and low-income housing markets

• The biggest mistakes investors make in emerging markets like West Virginia

• Getting Started in Real Estate without Money or Knowledge

Ray Glymph bought his first house and his roommate covered half of the mortgage. He rented out more rooms, utilized a short-term rental platform and realized that investing in real estate is actually a good idea.

Today Ray is passionate about building wealth and giving back to others. When he was young, his father lost his job following the economic fallout of September 11, 2001. Living in New York City with no income and no safety net, they ended up in a homeless shelter.

"I remember telling myself: I never want to put my kids in that position. Whatever it takes to succeed, I'm going to do it," Ray says. "And I also told myself that if I ever made it, I'd give back."

Today, he does exactly that. His portfolio is built heavily around low-income housing, Section 8, and HUD properties. He recently won a $1.5 million federal grant to redevelop affordable housing specifically for veterans, people with disabilities, and the unhoused.

Why Investors Should Consider the West Virginia Market

West Virginia is ideal for investors focused on affordable and low-income housing. You can buy affordable houses here but you should never enter a market without understanding the broader picture. Many investors make the mistake of overpaying for their properties.

"We don't have California prices here. Investors see comps and assume the ARV is going to be $300,000 or $400,000, but every street and every neighborhood is different. There are invisible lines within every community," Ray cautions. "One side of the bridge or the river can be a completely different market from the other. You have to know those lines before you invest."

You should take a hyper-local approach before investing capital.

How to Build a Portfolio Across Multiple Strategies

Ray Glymph has invested in multiple asset types, including Airbnbs, long-term rentals, Section 8 housing, and commercial and mixed-use properties spanning multiple neighborhood classes.

"I think every real estate investor should try a little bit of everything, figure out what they love, and find their balance," he says.

His favorite sector is commercial real estate, which is easier to manage at scale. Personally, he’s drawn towards low-income and Section 8 housing, as that allows him to give back to a community.

How to Eliminate Doubt and Start Investing

Almost every investor has to conquer self-doubt before they can complete their first deal. You will always get the feeling that you’re not prepared enough. But you can always find a coach and build your circle that supports you. Your mentor can link you with the right realtor, lender, and contractor. Investing becomes easy once you have built a team and can make informed decisions. Always invest in building trusted relationships with realtors, private money lenders, contractors, and other investors.

"Your network is your team," Ray says. "Building a strong network is what leads most people to success at this level."

Why Small Wins Beat Home Runs Every Time

Many investors enter real estate dreaming of the deal that will change everything overnight. Ray Glymph has over ten years of experience in the industry. This “big-win” focused mindset causes people to miss excellent opportunities right in front of them.

"The people who retire successfully in real estate had a lot of small wins — a property cash-flowing $300 a month that grew to $500, then $1,000. That growth takes time," he says.

On a personal level, Ray is focused on improving his health through consistent daily effort.

"You don't have to hit the gym. Just go for a walk. Do something," he says. "For some people, an extra $100 a week genuinely changes their lives. Just try to earn an additional $300 per month over the next 20-30 years. Small wins lead to everything."

What’s Your Philosophy for Success?

Success has three interconnected pillars: health, wealth, and freedom. You need all three to be truly successful.

"I know millionaires who take pills every day and have terrible health—that's not the life I want," he says. "And I know people with great health and wealth who work 80 or 90 hours a week and have no freedom. I want to go on vacation when I want. To do that, you need all three."

Ray Glymph uses a unique framework based on four pillars: family, faith, freedom, and finances. These pillars guide his everyday journey.

Ray recommends the book “Sell or be Sold” by Grant Cardone. It’s a book every investor should read because it offers a perspective on where you sit in every transaction and relationship in your life.

"Are you using social media, or is it using you? Are you the seller or the one being sold to?" he asks. "That book gives you a completely different lens for making decisions."

What's Next for Ray Glymph?

Ray Glymph wants to continue growing his portfolio and impact. He’s currently working on the $1.5 million affordable housing project. His goal is to continue expanding quality, affordable options for the communities that need them most.

Health remains his top priority alongside consistent, compounding wealth growth. His advice is to stop waiting for perfect conditions, as they never appear. Use fear as fuel, take small steps, and build a team around you that makes up for your blind spots.

"I didn't come from money. I didn't have overnight success," Ray says. "Fear of failure was my biggest setback—but I took it and made it my greatest strength."

Connect with Ray Glymph on Instagram and Facebook: @RayGlimph