Remote Real Estate Investors Lose Most When They Self-Manage, Warns Rent to Retirement Founder

Written by:

Steve Marcinuk

Date:

12 Aug 2025

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Zach Lemaster, Founder and CEO of Rent to Retirement, says his early mistakes in real estate investing taught him hard lessons about the perils of trying to manage everything alone, especially from a distance.

The High Cost of DIY Property Management

“Early on, some of the biggest mistakes I made is I tried to do everything myself,” says Lemaster, who started as an Air Force optometrist before building a real estate portfolio that allowed him to retire in his mid-30s. According to Lemaster, many new investors fall into the trap of self-management, thinking it will save money or help them learn the business.

But this hands-on approach often backfires, he argues. “When you’re investing in real estate, you’re building a business, if you [try to do everything yourself], you can be your own limiting factor in your business,” Lemaster explains. He points to critical mistakes in his early days: poor tenant screening, inadequate contractor vetting, and attempting to remotely manage properties in unfamiliar markets.

The Contractor Challenge

One of the most painful lessons, according to Lemaster, came from working with contractors. “You have to go through 10 bad ones to find one good one,” he notes, describing a pattern that plagues many real estate investors trying to build their teams from scratch.

This challenge becomes even more acute when investing out of state, where investors lack local networks and market knowledge. “We had a terrible experience and lost a bunch of money,” Lemaster says about his first out-of-state investment ventures.

The Hidden Costs of Learning Through Experience

Lemaster argues that many new investors underestimate the true cost of the DIY approach:

• Time spent screening and managing tenants
• Money lost to unreliable contractors
• Opportunity costs from focusing on operations instead of strategy
• Increased vacancy periods due to inefficient management
• Higher maintenance costs from poor vendor relationships

The Professional Management Solution

After these early setbacks, Lemaster shifted his approach entirely. His company now handles about 900-1000 properties annually across 18 different markets, with a focus on professional management and systematized operations.

“Management is, I don’t think anyone should self-manage properties,” he states firmly. “Your time is best spent working on your business, not in your business.”

This perspective aligns with what Lemaster learned from studying “The E-Myth” by Michael Gerber, which emphasizes the importance of building systems rather than doing everything yourself.

The Path Forward

For investors looking to avoid these common pitfalls, Lemaster suggests several key strategies:

• Invest in professional property management from the start
• Build relationships with vetted contractor networks
• Focus on market selection and strategy rather than day-to-day operations
• Create scalable systems that don’t rely on personal involvement

“Growing our portfolio that produces cash flow, whether we’re working or not, that’s fun. That creates a lifestyle,” Lemaster says, highlighting the ultimate goal of true passive income through real estate.

His company now helps other investors avoid the mistakes he made, providing turnkey solutions that include property management and established contractor networks. While this approach may cost more upfront, Lemaster argues it’s far less expensive than learning these lessons the hard way, as he did in his early investing days.