77. Buying Site Unseen, Creating Content, and Arguing Zillow Vs Compass With Grady Schmidt

Send us Fan MailYou can do a lot with a steady W-2 paycheck if you’re willing to get a little uncomfortable. We sit down in The Nook with Grady Schmidt, a Chicago-based investor who starts with a garden-unit condo and turns it into a no-frills house hack, then scales into buying site unseen Indiana rentals while working in finance at Google. He shares the exact choices that helped him move fast, including why he used 25% down, how he picked Midwest markets like East Chicago, Michigan City, and South Bend, and what he wishes he’d understood before trusting the “clean” spreadsheet numbers.We also get into the messy parts that make you a real operator: tenant risk, property management, maintenance you can’t ignore, and how capex items like roofs can wreck your expectations if you treat them like ordinary monthly expenses. Grady walks through his first eviction, why Indiana timelines shocked us compared to Chicago, and how he kept going even when early cash flow didn’t show up the way BiggerPockets-style projections promised.Then we zoom out to bigger forces shaping real estate investing in 2025. We debate cash flow versus appreciation and why higher rates push investors to think differently about Chicago fundamentals. We also unpack the Zillow vs Compass private listings fight, why it matters to consumers, and how “gatekeeping” inventory raises real questions about fairness and access. Along the way, Grady explains how AI is changing work, why context and judgment protect your career, and how posting content (even when it’s embarrassing) can open doors.Subscribe for more real-life investing stories, share this with a friend who’s trying to buy their first property, and leave a review with your biggest takeaway.Grady Schmidt Bio:Grady is a real estate investor and full-time finance professional at Google in Chicago. After starting with a condo-hack in downtown Chicago, he’s since moved on to purchasing multifamily buildings in northern Indiana. He enjoys combining his professional experience with AI and his real estate background to build new tools for investors. Grady recently started dabbling as a (very) amateur content creator, sharing his thoughts on real estate, career development, AI, and Cincinnati Reds baseball at @gradybuysproperty on Instagram.