Why Your Starting Point Doesn't Matter in Real Estate Investing

How Did You Get Started in Real Estate?

Jiries Dawaher graduated from high school in 2002 with a 1.53 GPA. He ranked 311 out of 320 students in his class and soon realized that traditional college wasn’t a realistic option for him. Jiries Dawaher joined the Army in 2001 as a helicopter mechanic. What happened next was a surprise even to Jiries.

"I went into one of the most difficult schools in the military and graduated as the distinguished honor graduate. The military taught me one thing: You don’t need to know all the answers, but you just need to know where to find them.”

That mindset became the foundation of everything Jiries built after leaving the military. He had no savings and a destroyed credit score, but he was still able to find his path to financial freedom.

Finding Success through Wholesaling

Jiries Dawaher built a wholesale operation in Cincinnati back in 2010. Over six years, he completed more than 1,000 wholesale transactions. His company ran short sales, sheriff sales, probate deals, MLS deals, and direct-to-seller campaigns across the market.

He repaired his credit score, learned how to talk to sellers and buyers, house-hacked his way into ownership, and learned how to raise private money. Wholesaling gave him the education that no school ever did.

How Did You Find Your First Wholesale Deal?

Jiries got his first deal from the MLS. He believes you can secure deals from the MLS, but you still have to put in the work.

“I found a listing, ran the numbers, and immediately sent an offer. I got the house under contract for $75,000 and sold the contract to two brothers for $83,000. The buyers were local investors who had just flipped a house a few streets over and were specifically hunting for brick Cape Cods in that pocket of Deer Park. The stars had aligned and it turned out to be a perfect deal.”

Wholesaling Real Estate Doesn’t Bring Passive Income

In just six years, Jiries was making six figures through a wholesale business, but he chose to walk away. If you look closely, wholesaling is a time-consuming job. You are trading time for money. You are always looking for the next deal.

However, there are people who are generating long-term wealth by building massive rental portfolios. That's why Jiries decided to buy his first rental property in 2016. By 2020, he had scaled from zero to over 60 doors in under five years.

Favorite Investment Strategy

Jiries has succeeded with various investment strategies: wholesaling, SFH rentals, small multifamily, and full-scale hotels. His favorite strategy is to use the BRRRR method with two-to-four unit properties. Small multifamily units can be financed with conventional residential mortgages, and you can generate multiple income streams from a single purchase.

"You don't need to scale up to large apartment complexes or hotels. If you play in that arena, the right way, in the right appreciating markets, you can build a very nice life. It's game over."

How Do You Find Deals in Today's Market?

Jiries invests primarily in Cincinnati, Ohio, and surrounding markets like Covington, Kentucky. He uses multiple channels to source deals, but he's clear about which one produces the best results.

"I love direct-to-seller. The best deals come from going directly to the seller, building that relationship, solving their problem, and putting the property under contract."

Jiries Dawaher believes in forcing appreciation. His strategy is to look for functionally obsolete properties.

"These properties were once in great condition, but now there's something off about them. The layout doesn't work. There's an extra dining room that doesn't need to be there. The bedrooms are configured oddly."

These quirks scare off most buyers. They see a problem with no obvious fix. Jiries sees an opportunity.

His most common moves:

• Converting a three-bedroom, one-bath into a three-bedroom, two-and-a-half-bath. Modern renters expect more than 1 bathroom when you have three bedrooms.
• Turning a one-bedroom apartment into a true two-bedroom. By adding a wall and creating defined space, he can command higher rent.
• Transforming studio-style units into proper one-bedroom units with defined living rooms, kitchens, and bedrooms

Each of these improvements forces appreciation. The property becomes valuable because of its high income potential. Once the renovation is complete, he refinances using the BRRRR method to get back his capital, which can be deployed into the next deal.

Real Investment Numbers on a Deal in Kentucky

At the time of the interview, Jiries Dawaher was renovating a deal in Covington, Kentucky, which is across the Ohio River from Cincinnati.

• Acquisition method: He bought it from a tired landlord. It was a 4-unit, but he also had to buy the adjacent SFH as part of the deal.

He negotiated both properties for a combined $290,000. Then he immediately wholesaled the single-family for $90,000, which reduced his basis in the four-unit to around $200,000.

• The renovation plan: The units were technically listed as one-bedrooms, but they functioned like studios because of the cramped layout and lack of a clearly defined bedroom. Jiries reconfigured each unit into a proper one-bedroom property.

Scaling a Real Estate Business from 60 to 150 Doors

Jiries Dawaher has a unique philosophy about scaling his investment business. He only hires teammates who are specialists.

"My window guy is just my window guy. My tile guy is just my tile guy. My glass block guy is just my glass block guy. My carpenter is just a carpenter."

His goal isn't a big staff. It's a wide bench of specialists that he can call on when needed. As he scales toward 150 units, the answer isn't to hire more project managers. It's to have more of the same trade-specific people he already trusts.

What’s the #1 Thing Holding New Investors Back?

Many investors are not consistent, but you must stay persistent until desired results are achieved.

His student Greg Burks is the proof of what staying consistent looks like. Greg is in his 50s, works full-time as a carpenter, and spent two years completing his first BRRRR deal. It took him two years. But at the end of it, he walked away with roughly $40,000 tax-free.

"If he'd quit after six months, he would have nothing. Because he stayed consistent, he has $40,000 — and a blueprint he can repeat for the rest of his life."

What Does It Mean to Stay Persistent in Real Life?

You can always get something if you want it badly enough. Jiries mentioned his student (Damon) who was taking coaching calls from prison. The Wi-Fi was terrible, and the audio was barely audible, but his student was persistent in his efforts. Within three months of being released, Damon bought his first rental property. He now has three rental properties.

"He didn't let his circumstances dictate where he could go or what he was allowed to do. His story is insane. And I'm so grateful to be even a small part of it."

Rental Property Investing: How to Go from Broke to Seven Figures in Five Simple Steps

Jiries Dawaher authored his book on rental property investing, but he told us that some investors miss key steps. The answer loops back to the same theme.

Consistency — and specifically, the failure to pursue it within a community.

“It’s a deal killer if you are trying to do it alone. You need people by your side. You will fall apart if you don’t have accountability and a community that holds you to your commitments. The knowledge is there. The deals are there. But without consistency inside a support system, it doesn't matter.”

Jiries Dawaher asks investors to commit to just 30 minutes a day. Read the book they've been avoiding. Listen to the audiobook on the commute. Go for a walk that clears one's head. Small daily investments in your own knowledge and mindset compound the same way equity does.

Rapid-Round Answers: Jiries Dawaher

• Best market for investors right now? Midwest.

• Biggest mistake new investors make on their first deal? Rushing into the wrong deal.

• Credit score doesn't matter in real estate—true or false? True.

• One tool or resource you can't live without? Redfin. It's free and it's powerful.

• Army or real estate—which taught you more about discipline? Real estate.

• What does financial freedom look like for you day-to-day? "Slow mornings. Waking up when I'm done sleeping. Meeting contractors at 9 a.m. instead of 7. Missing traffic. Getting to do what I want, when I want. That's it."

If You Woke Up Tomorrow with Nothing—No Money, No Network, No Credit—What's Your Move on Day One?

"I would get my real estate license and go drive for dollars."

Getting licensed opens certain doors for you, like accessing MLS, writing your offers, earning commission on transactions, and gaining credibility with sellers. Driving for dollars costs nothing but time and builds a direct-to-seller pipeline from day one.

What's Next for Jiries Dawaher?

Jiries is focused on scaling his portfolio from 60 to 150 units, and he has already acquired 9+ units in 2026. He is refining his systems and continues to work in Cincinnati and the Northern Kentucky markets. He is also growing his mentorship community, where he has coached 3,000 investors to get their first deal, and 150 have already left their W-2 jobs. At the time of the interview, he was expecting a baby in a few weeks. So congratulations to Jiries for this new chapter of his life. You can connect with Jiries Dawaher via Instagram @Jiriesd or his website.

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