Renovopalooza 2026 - Grit, Relationships, and Real Estate Investing with Teo Scorte and Tom Shallcross

In this live episode of the Hustle Harder Show from Renovopalooza in Chicago, James Gaskin sits down with real estate investors Teo Scorte and Tom Shallcross, alongside Eric Workman. Teo and Tom share how they built their businesses, lessons learned from difficult deals, and why grit, financial literacy, and strong relationships matter in real estate. They also discuss Chicago’s real estate market, what they value in a lending partner, managing unexpected challenges, and advice for young professionals looking to build long-term wealth. Key Discussions From This Episode: \[00:00:00] Intro \[00:01:19] Live introduction from Renovopalooza in Chicago \[00:02:37] Teo’s early exposure to construction and transition into real estate development \[00:03:33] How real estate gave Teo greater flexibility and time with his family \[00:05:55] Tom’s path from tech sales to full-time real estate investing \[00:06:47] Family, freedom, and controlling your own schedule \[00:10:16] Why Teo and Tom concentrate primarily on real estate investments \[00:11:38] Teo’s experience through the 2008 crash and rebuilding through construction \[00:14:57] Tom’s high-end flips and smaller multifamily investment strategy \[00:15:54] Building the Straight Up Chicago Investor podcast \[00:17:23] Teo’s demolition-court scare and the importance of a strong team \[00:19:38] Tom’s experience buying a property involved in title fraud \[00:20:39] Why experience and resilience matter when real estate deals go wrong \[00:22:31] Grit and purposeful action as foundations for real estate success \[00:24:05] Why Teo pairs grit with strong financial literacy \[00:24:52] Eric on the importance of relationships and building a strong network \[00:26:38] Tom’s perspective on the long-term opportunity in Chicago real estate \[00:29:04] Teo’s outlook on Chicago and why he continues investing locally \[00:30:14] Chicago’s ability to attract young talent from across the Midwest \[00:33:10] Speed, consistency, and culture in choosing a lending partner \[00:36:04] Why reducing friction and creating certainty matters to borrowers \[00:37:58] Maintaining client relationships in a competitive lending market \[00:39:47] Teo’s advice for Renovo employees as the company grows \[00:41:11] Tom on making every client interaction as simple as possible \[00:42:11] How company culture and consistency shape the borrower experience \[00:44:34] Teo’s stories about building relationships with Daniel Rosen and the Renovo team \[00:48:13] Tom and Eric’s early relationship and first lending experiences together \[00:50:35] Common mistakes investors make when evaluating deals \[00:52:54] Maintaining discipline instead of forcing the numbers on an acquisition \[00:54:35] Turning appraisal misses and unexpected problems into actionable information \[00:56:23] Using scenario analysis to account for uncertainty when underwriting \[00:57:47] Teo’s advice to young professionals: save money and build toward generational wealth \[00:59:39] Tom’s advice to learn from experienced developers, save, and take action when ready \[01:00:02] Closing remarks from Renovopalooza Links: Renovo Financial - https://renovofinancial.com/ James Gaskin on LinkedIn - https://www.linkedin.com/in/james-gaskin-b675593/ Teo Scorte on LinkedIn - https://www.linkedin.com/in/teo-scorte-ab51b815/ Tom Shallcross - https://www.linkedin.com/in/tomshallcross/ Eric Workman - https://www.linkedin.com/in/eric-workman-1681996/ Straight Up Chicago Investor Podcast - https://www.straightupchicagoinvestor.com/podcast