Ep137: Discipline Through Cycles, Contrarian Investing, and Building Enduring Value with Andy Weiner

A failed family retail business, a changing industry, and a willingness to think differently became the foundation for a career built on discipline, adaptability, and long-term value creation for Andy Weiner. Andy is the Founder and CEO of RockStep Capital, and on this episode, we talked about what it takes to invest successfully through multiple market cycles while staying committed to a clear strategy. Listen wherever you find podcasts! While headlines often focus on the impact of e-commerce and shifting consumer habits, he explains why strong retailers continue to expand and why limited new construction of shopping centers has created favorable supply-and-demand dynamics for owners. He shares how RockStep identifies opportunities in what it calls "Hometown America," focusing on growing communities outside major metro areas where quality of life, population growth, and local engagement drive long-term success. The conversation also examines the importance of underwriting discipline, conservative use of debt, and the patience required to walk away from deals that do not meet strict investment criteria. Andy discusses why complexity often creates opportunity, particularly in retail and enclosed malls, where fewer investors are willing to do the deep work required to uncover value. Listeners will gain insights into contrarian investing, navigating uncertainty, building resilient teams, and creating enduring value through disciplined decision-making, community engagement, and a long-term perspective. In this episode, you will hear: -Investing through cycles, not chasing them -Why retail is misunderstood and still full of opportunity -The discipline required to operate over decades -Revitalizing communities through real estate -Building a values-driven company culture that lasts Chapter 00:00 - Meet Andy Weiner 03:21 - No leaders, no deal 05:52 - We lost six deals 07:20 - Small town advantage Resources from this Episode www.rockstep.com Andy Weiner on LinkedIn:   / andy-weiner   YouTube: TBD Insert link to the episode of why Andy's family business was killed by Walmart amycalandrino.com creorlando.com thecalandrinofoundation.org Follow and Review: We’d love for you to follow us if you haven’t yet. Click that purple '+' in the top right corner of your Apple Podcasts app. We’d love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select “Ratings and Reviews” and “Write a Review,” then a quick line with your favorite part of the episode. It only takes a second, and it helps spread the word about the podcast. Episode Credits If you like this podcast and are thinking of creating your own, consider talking to my producer, Emerald City Productions. They helped me grow and produce the podcast you are listening to right now. Find out more at https://emeraldcitypro.com. Let them know we sent you. #CommercialRealEstate #RetailInvesting #ContrarianInvesting