Common Missteps of First-Time Investors with Stephen Predmore, Ep. 734

Stephen Predmore is the founder and managing partner of Talbott Investments. A former engineer with over 20 years of experience in the manufacturing industry, Stephen transitioned into real estate after a sudden layoff. Since then, he’s grown from single-family investor to general partner in multifamily, specializing in JV structures and educating engineers on passive investing strategies.

 

 

📢 Announcement

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Key Takeaways

• Getting laid off inspired Stephen to shift from engineering to real estate investing.

• Initial investments in high-cash-flow rentals revealed the operational challenges of managing tenants and maintenance.

• Transitioning to passive investing provided stronger returns with less stress and time commitment.

• JV deals allow Stephen to combine the benefits of active and passive investing with small groups and creative value-add strategies.

• Engineers often underestimate the time burden of active real estate and over-rely on spreadsheets instead of evaluating lifestyle impact.

 

 

Topics

From Layoff to Landlord

• How a sudden post–Super Bowl layoff catalyzed Stephen’s investing journey.

• Lessons learned from early Baltimore rental properties, including eviction challenges and Section 8 issues.

The Case for Passive Investing

• LP investing offers more stability and better returns than small-scale rentals.

• Passive deals free up time while enabling continued W-2 work or other ventures.

• Stephen highlights how his handyman side hustle now fuels his passive portfolio.

JV Deals and Strategic Value-Adds

• Recent acquisitions in West Virginia and Alaska with JV partners.

• Boosting NOI with storage unit additions, washer/dryer installations, and electrical upgrades.

• Investing in red states with favorable landlord laws.

Engineering the Passive Path

• Why professionals—especially engineers—should consider passive syndication investments.

• Real estate isn’t always passive: time cost, emotional stress, and operational friction are often overlooked.

Common Missteps of First-Time Investors

• Underestimating time and headspace costs.

• Taking court battles personally instead of hiring help.

• Forgetting that return on time is just as important as return on capital.

 

 

📢 Announcement

Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.

 

 

Round of Insights

Failure that set Stephen up for success: Early struggles managing rentals in Baltimore—evictions, repairs, and stress—led to a smarter pivot to multifamily investing.

Digital/Mobile Resource: Canva — essential for creating content quickly and easily, especially on the go.

Book Recommendation: Who Not How — reading it twice helped him delegate, hire VAs, and focus on high-value tasks.

Daily Habit: Works every weekday after his W-2 job, either going to the gym or working a handyman job to generate capital for investing.

#1 Insight for Scaling into Multifamily: Surround yourself with like-minded people—mentors, coaches, and communities normalize the journey and accelerate growth.

Favorite restaurant in Baltimore, MD: Pappas Restaurant.

 

 

Next Steps

• Learn more at talbottinvestments.com/engineer-12-reasons, where Stephen offers a free guide tailored for engineers exploring passive investing.

• Follow Stephen on LinkedIn to explore his writings and connect with his network.

 

 

Closing Call to Action

Thank you for joining us for another great episode! If you’re enjoying the show, please LEAVE A RATING OR REVIEW, and be sure to hit that subscribe button so you do not miss an episode.