The Hidden Complexity of "Simple" Self Storage with Jackson Stevens from Sparebox Technologies

Welcome back to Self Storage Lab, the podcast where we deconstruct how operators are adapting to today’s technology-driven landscape—and what it means for the future of the industry.


This episode’s guest is Jackson Stevens, co-founder and CEO of SpareBox Technologies. From classical musician to building one of the most operator-informed tech stacks in self-storage, Jackson’s path is as unconventional as it is compelling. Before SpareBox, Jackson played a pivotal role in building Red Dot’s internal FMS platform, scaling SpareBox Storage to over 7 million square feet, and launching tech that bridges the gap between traditional management and remote-first ops.


In this episode, we explore:

• Why self-storage tech looks simple, but isn’t.
• Jackson’s first principles approach to problem-solving in operations.
• The critical role of field experience in designing better tools.
• Lessons from music, CrossFit, Toyota, and call centers that shaped SpareBox’s roadmap.

If you’ve ever tried to build tech that actually works in the real world—or wondered what the future of remote operations looks like—this episode’s for you.


Also in our queue: Episode 25: The Modern FMS with Cubby CEO Matt Engfer (https://www.tryswivl.com/blog/the-mod...)


In this episode we discussed:


(00:00:20) From Baroque music to bold tech—Jackson’s winding path to storage.


(00:02:31) Pattern recognition, CrossFit, and life as a percussionist.


(00:06:50) Why most music school grads now work in tech.


(00:09:00) Creativity, culture, and leadership rituals inside a lean startup.


(00:14:30) Swivl x SpareBox: behind-the-scenes GTM playbook swaps.


(00:19:00) Building Redline—Red Dot’s internal FMS—and the hard lessons learned.


(00:24:45) Spending time with users: the lost art of field empathy.


(00:26:50) The surprising edge cases that complicate "simple" storage software.


(00:33:45) Auctions, automation, and designing for scale from day one.


(00:36:30) When solving your own pain points becomes a product strategy.


(00:39:15) Crossing the chasm: how SpareBox navigates adoption in a slow-moving industry.


(00:43:00) Consumer expectations vs. operator workflows—where we’re still catching up.


(00:46:11) TikTok tours and 5x5s: The REITs get social.


(00:49:45) Why most storage customers are first-timers—and what that changes.


(00:52:15) Elon Musk, agile retrospectives, and the pursuit of elegant ops.


(00:54:57) The case for remote-first ops—and what’s holding the market back.


(01:00:12) Why self-storage might lead the charge in virtual CRE playbooks.


(01:08:00) What Jackson would reinvent next—and the tech trend he thinks is overhyped.






Mentioned in This Episode:


Frameworks & Philosophies

• Agile & Scrum (Certified Product Owner)
• Toyota Production System
• First Principles Thinking
• Elon Musk’s operating rules
• Six Sigma & Gemba Walks

Internal Tools & Innovations

• Auction automation workflows
• Internal customer service manuals
• Remote onboarding through site visits
• Cross-departmental culture rituals

Favorite Nuggets

• “Show your work” as a collaboration philosophy
• Why your ops stack needs a melodica mindset—flexible, multi-purpose, and creative
• TikTok, Da Vinci locks, and the underrated power of a clean spreadsheet





🔗 More from Jackson & Team:
https://spareboxtech.com
  / jacksonstevensco  






If you haven’t already, go download our guide to Abandoned Cart workflows “Win-Back Opportunities. (https://www.tryswivl.com/resources/ab...) ” We cover how to capture revenue from potential customers who start checking out on your website, but don't quite finish the process.