Common Missteps of First-Time Investors with Stephen Predmore, Ep. 734
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Written by John Casmon

July 29, 2025

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

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.