The Good, Bad, & the Ugly of Self Storage
The Good, Bad, & the Ugly of Self Storage
Podcast Description
Thinking about building, owning, or managing a self-storage facility?
Join Michael Cunningham, a seasoned self-storage developer, and his son Dylan Cunningham as they reveal the good, bad, and ugly of the industry. Whether you’re a first-time investor or a veteran operator, this podcast gives you real-world insights, expert strategies, and hard-learned lessons to help you succeed.
Each episode dives into site selection, development, marketing, operations, and the biggest mistakes to avoid—so you can maximize profits and sidestep costly errors. Plus, hear from industry pros shaping the future of self-storage.
🚀 Subscribe now and build a thriving storage business—without the trial and error!
Podcast Insights
Content Themes
Covers a wide range of topics related to self-storage, including site selection, development processes, marketing strategies, and operational challenges, with episodes like 'Before You Break Ground' that emphasizes entitlement and permitting complexities, and discussions on market risks and eco-conscious upgrades.

The Good, Bad, & the Ugly of Self Storage is a real-world podcast about self storage investing, development, and management, hosted by father-son duo Michael and Dylan Cunningham. Whether you’re a real estate investor exploring the self-storage industry for the first time or a seasoned professional looking to scale your portfolio, this show is packed with value.
Each episode covers the practical side of the business—from buying your first self storage property, to building facilities, managing operations, marketing, using the latest technology, and everything in between. If you’re interested in real estate investing, passive income, or building wealth through self storage ownership, you’ll find expert insights, honest stories, and actionable advice to help you avoid costly mistakes and thrive in this rapidly growing industry – without the trial and error. Plus, hear from industry pros shaping the future of self-storage.
🚀 Subscribe now on Spotify and Apple Podcasts, and join us as we explore the good, the bad, and the sometimes ugly side of self storage.
In this episode Michael and Dylan Cunningham discuss tax strategies for self-storage investors with Heidi Henderson, Chief Marketing Officer at Engineered Tax Services. Heidi explains various tax incentives, including cost segregation, which can accelerate depreciation and reduce tax liabilities. She also covers the benefits of being a real estate professional, which allows for more deductions. The discussion includes the impact of the “Big Beautiful Bill” on bonus depreciation and opportunity zones, which offer tax-free gains for investments in designated low-income areas. Additionally, they touch on advanced tax strategies like captive insurance and charitable lead trusts for high-net-worth individuals. The discussion also touches on the importance of tax strategies for self-storage owners, suggesting that those not advised on these matters may need to seek new tax advisors.
Heidi Henderson

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