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The Landlording Show - Episode 18 - From House Hacking to Private Lending: With Bryce Matheson

In the world of real estate investing, everyone’s journey looks different. Some start by purchasing a small single-family home, while others might dive straight into multifamily properties or large commercial ventures. For Bryce, a seasoned real estate investor, the path was shaped by experimentation, learning, and adaptability. His journey led him from a modest start in house hacking to building a significant rental portfolio, transitioning to house flipping, and ultimately settling into hard money lending. His story offers valuable insights for anyone looking to find their own path in real estate.

1. The Humble Beginnings: House Hacking

Bryce’s real estate journey began in 2016 in a way many might find familiar: house hacking. Without even realizing it was a coined strategy, he purchased a single-family home and rented out the extra rooms to offset his mortgage. This strategy allowed him to get his feet wet in real estate without the need for extensive capital.

After getting married, Bryce and his wife sold his first house, walking away with a $40,000 check—a sum that matched his annual income at his W-2 job. This was a turning point. He saw firsthand the financial potential of real estate, igniting a passion that would eventually transform his career.

2. Scaling Up: Building a Rental Portfolio

With his initial capital in hand, Bryce and his wife made the decision to reinvest in real estate. They purchased a second property—a duplex—and soon after, another. This phase involved leveraging available capital creatively, including tapping into a line of credit on his wife’s property.

Within 12 months, they had accumulated 12 rental units, generating a net cash flow of $2,600 per month. While this was significant passive income, Bryce noted that managing multiple rental properties came with its own set of challenges. Even as they scaled to around 40 doors, he remained hesitant to use a property manager, preferring instead to rely on his own systems and processes for tenant management, maintenance, and rent collection.

3. The Emotional Toll of Property Management

Despite the financial rewards, managing a portfolio of rental properties took an emotional toll. For Bryce, the mental weight of managing dozens of units—handling repairs, tenant turnover, and the general upkeep of properties—began to feel burdensome. While he had automated many of the processes and hired a full-time maintenance person, the properties themselves occupied mental space that disrupted his peace of mind.

This inner conflict isn’t uncommon among landlords. Many investors find themselves emotionally attached to their properties, feeling responsible for their upkeep in ways that extend beyond financial logic. Bryce recognized that, for him, peace of mind was more valuable than expanding his rental portfolio further.

4. Flipping Houses: The Thrill of Transformation

Seeking a change, Bryce pivoted from buy-and-hold rentals to house flipping. He found joy in the transformation process, from planning the renovation to choosing design elements alongside his wife. House flipping also offered larger, quicker paychecks compared to rental cash flow.

At their peak, Bryce and his wife were flipping up to 25 houses per year, grossing nearly a million dollars in revenue. However, he soon learned that gross revenue does not always equate to profit. After expenses, their net earnings were closer to half of the gross amount. Still, the experience taught him valuable lessons in project management, budgeting, and the realities of the flipping business—lessons that would later inform his approach to lending.

5. A New Path: Hard Money Lending

During the COVID-19 pandemic, Bryce encountered significant delays and rising costs in his flips, with supply shortages affecting his project timelines and profits. One particularly challenging project stretched on for over a year, and the profit at the end barely justified the effort. Meanwhile, his hard money lender, who had provided financing for the flip, earned a reliable return without the stress Bryce experienced.

This realization was pivotal. Hard money lending offered the opportunity to stay engaged in real estate while avoiding the hands-on demands of property management or flipping. With his capital and experience, Bryce could lend to other real estate investors, secure in the knowledge that his investment was backed by collateral. Soon, he transitioned fully into lending, creating a real estate fund and focusing his energy on sourcing quality deals rather than managing properties or overseeing renovations.

6. The Appeal of Hard Money Lending

Hard money lending has allowed Bryce to enjoy the best of both worlds. He’s still involved in real estate, analyzing deals, assessing borrowers, and evaluating properties—but he’s removed from the daily stress of property management and renovations. His lending business typically yields annual returns of around 20% on his capital, providing a high, consistent income stream with significantly less work and fewer headaches than managing rentals or flips.

For Bryce, lending aligns perfectly with his current financial and lifestyle goals. It allows him to focus on growth without the operational complexities that come with other forms of real estate investment. His current goal is to scale his fund to $10 million within a year, and eventually reach $25 million over the next few years.

Key Takeaways from Bryce’s Journey

Bryce’s journey offers several insights for aspiring real estate investors:

  1. Start Small and Use What You Have – House hacking allowed Bryce to enter the real estate market with minimal initial investment. It’s an accessible strategy that can work well for beginners.

  2. Learn and Adapt – Real estate is a vast field, and there are many ways to succeed. Bryce’s willingness to shift strategies—from rentals to flipping to lending—allowed him to find the niche that best suited his skills, interests, and financial goals.

  3. Know Your Limits – Even profitable investments can have downsides. Managing 40 rental units may sound like the dream for passive income, but Bryce found the emotional weight was more than he was willing to bear. Recognizing when something no longer aligns with your life goals is crucial.

  4. Find Joy in What You Do – Bryce discovered that he and his wife enjoyed flipping houses because it allowed them to be creative. Finding joy in the process made the work feel worthwhile, even though flipping ultimately became a stepping stone rather than the end goal.

  5. Look for Stability – Hard money lending offered Bryce the financial stability and peace of mind he craved. By lending instead of managing or renovating, he could enjoy passive income without the hands-on demands of his previous ventures.

Final Thoughts

Bryce’s real estate journey illustrates that there’s no one-size-fits-all approach to building wealth in real estate. His progression from house hacking to rentals, flips, and finally lending reflects a thoughtful, adaptive approach. Real estate investors should feel empowered to explore various strategies, assess what aligns with their financial goals and personal preferences, and make changes as needed.

For those interested in real estate but daunted by the thought of long-term property management or high-stakes flipping, hard money lending could be an attractive option. Just as Bryce learned to adapt his strategy to suit his strengths and lifestyle, aspiring investors can explore different paths to find their unique formula for success.

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