Building Wealth Through Real Estate Investment with Luke Sanders

Sidebar with a CFP®: Pierce the Veil on BigLaw Life, Career, and Money with Matt Smith, Episode 6

In this episode of the Sidebar with a CFP®: Pierce the Veil on BigLaw Life, Career, and Money, Matt Smith, speaks with Luke Sanders, owner of River City Screen Printing and Embroidery in San Marcos, Texas, which was founded by his parents in 1978 and grown to 85+ employees across multiple buildings.

Tune in to the episode to hear about:

  • How Luke first built wealth through acquiring and expanding commercial real estate for his operating business, including buying adjacent buildings and leasing one to a pawn shop tenant

  • Entering short-term rentals in 2019, including a large river house in New Braunfels/Green and multiple Fredericksburg properties

  • How COVID initially created cancellation risk but later produced a major demand surge (e.g., $80,000 revenue in one month) followed by market oversaturation

  • Regulatory and licensing uncertainty (city council efforts to restrict or sunset short-term rental permits)

  • Commercial loan structures with five-year rate resets that can turn cash flow negative

  • Reliance on local market knowledge and specialized realtors

  • Frequent maintenance/replacement costs from guest wear-and-tear

  • Using property management companies (typically 20–30% of revenue) to avoid 24/7 operational issues

  • Rising insurance costs (e.g., from $3,000 to $15,000 annually)

  • FEMA floodway rezoning that can eliminate short-term rental use

  • Why short-term rentals are risky for anyone depending on slim monthly margins

  • Why Luke’s best, least stressful results have been in commercial buildings with stable tenants

Learn more about Luke Sanders:

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About “Sidebar with a CFP®: Pierce the Veil on BigLaw Life, Career, and Money”:

You bill in 6-minute increments. Let’s get you some of that time back. “Sidebar with a CFP®” is your space for candid conversations about life inside BigLaw—the real stuff they don’t teach in law school or show in recruiter brochures.

Hosted by Matt Smith, CFP® and founder of Concert Financial Planning, this show pulls back the curtain on what it actually feels like to climb the ranks, navigate transitions, and make big decisions in a high-stakes career.

You’ll hear from Partners, Associates, and experts across law and finance—each sharing stories, surprises, and strategies for building a life (and career) that works for you.

This isn’t a money podcast. It’s a life-in-BigLaw podcast—with a CFP® in the host chair.

Watch or listen to more episodes of Sidebar with a CFP®: Pierce the Veil on BigLaw Life, Career, and Money:

Connect and learn more from your host, Matt Smith and Concert Financial Planning: