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Leap Before You Look: Embracing Risk and Innovation with CEO AJ Osborne

Leap Before You Look: Embracing Risk and Innovation with CEO AJ Osborne
Photo Courtesy: AJ Osborne

By: Victoria Kennedy

Conventional wisdom often champions meticulous planning and deep expertise as the prerequisites for success in many pursuits. However, AJ Osborne, CEO and Founder of self-storage investment firm Cedar Creek Capital, embodies a strikingly different mantra: the art of venturing into the unknown or, in his recent words on Austin Zelan’s Better Business Podcast episode, “doing before you know.”

Osborne’s journey through the labyrinth of the self-storage industry — culminating in a vertically integrated powerhouse that includes multiple verticals across the self-storage industry, not limited to investing and management tech — illustrates a potent blend of risk-taking and strategic acumen rarely seen in traditional business narratives.

This article explores the entrepreneurial philosophy of Osborne, focusing on the importance of taking risks, embracing uncertainty, and the transformative power of “doing before you know” in building a successful and innovative business empire.

The Genesis of a Self-Storage Empire

Osborne’s trajectory wasn’t charted in advance. Instead, it unfolded through a series of calculated risks and an eagerness to leap into unfamiliar territories. Starting with an endeavor to mitigate tax liabilities through passive income avenues, Osborne stumbled upon the self-storage sector. What initially began as a means to offset earned sales income from an insurance brokerage evolved into a full-fledged enterprise. This pivot wasn’t the result of exhaustive research or a well-trodden path but, rather, an instinctive move to capitalize on an underrecognized opportunity.

Osborne’s approach to business deviates markedly from the norm. Where conventional wisdom advises against spreading oneself too thin, he has championed the value of diversification. Cedar Creek Capital is a self-storage investment company; however, AJ Osborne is a conglomerate that touches upon every facet of the industry, from development to management, tech solutions, and education. This empire was not built overnight, nor was it built on the foundation of certainty. Instead, it grew from a willingness to embrace the unknown and a relentless pursuit of innovation.

“In entrepreneurship, it’s the opposite [of school, where you ‘know’ before you ‘do’]; you ‘do before you know,’ and you figure it out and you build right,” Osborne shared. “That is so counterintuitive to what we’re taught and told that we’re supposed to do.”

Mindset Over Matter

In entrepreneurship, Osborne argues that the big hurdle is often one’s mindset. The educational system ingrains a fear of the unknown, teaching individuals that knowledge precedes action. Yet, in the entrepreneurial realm, this sequence is reversed. Success comes from action: stepping into the arena without the safety net of complete knowledge, learning on the fly, and iterating toward perfection. This philosophy underpins not only Osborne’s success but also his contribution to the self-storage industry, transforming it through a mix of daring ventures and strategic foresight.

Furthermore, Osborne’s narrative underscores the significance of mindset, resilience, and the constant search for improvement. His journey from leveraging self-storage facilities to making an impact in the industry through a vertically integrated model encapsulates the essence of “doing before you know.” He knows and recommends the power of venturing beyond comfort zones, leveraging every setback as a stepping stone, and relentlessly pursuing growth and innovation.

In this era of entrepreneurship, where uncertainty is the only certainty, Osborne’s journey offers a compelling blueprint. It’s a narrative that champions the unconventional, encouraging entrepreneurs to embrace the unknown, to leap before looking, and to learn the art of flying mid-air. It’s a reminder that in the quest for innovation and growth, sometimes the best strategy is simply to start: to do before you know.

About AJ Osborne

AJ Osborne is the distinguished CEO of Cedar Creek Capital. With two decades of unparalleled experience in the self-storage industry as an owner, operator, and developer, AJ’s impact is evident through his founding and board membership of Storelocal, a large self-storage co-op, and Tenant Inc., an innovative SaaS company transforming self-storage facility management. Renowned for his bestselling book on self-storage investing and the highly acclaimed Self Storage Income podcast, AJ Osborne stands as a beacon of knowledge and innovation in the field. More information can be found at cedar.cc.


Published By: Aize Perez

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