AJ Osborne

CEO of Cedar Creek Capital

AJ Osborne is the CEO of Cedar Creek Capital and has an impressive 20 years of experience as a self-storage owner, operator, and developer. He is a founder and board member of the largest self-storage co-op, Storelocal, as well as Tenant Inc — a saas company supporting self-storage facility management. AJ has also written the No. 1 bestselling book on self-storage investing and hosts the top-rated and listened to self-storage podcast, Self Storage Income. Accredited investors can find more information here: cedar.cc

What is your typical day, and how do you make it productive?

My day kicks off with a jolt due to chronic pain, but there’s no time to linger. My wife takes charge of the morning family hustle while I dive into emails and work tasks. By 8:30 to 9:30 AM, I’m in the office, usually burning the midnight oil till 7 or 8 PM.

To keep things buzzing, I brought in an executive assistant as my gatekeeper. We streamlined tasks after a deep dive with a third-party, freeing me up for what really matters. I wear multiple hats – overseeing boards, shaping visions, and hustling with my COO in weekly goal meetings.

Evenings are my canvas for educational marketing and setting the future’s tone. The daily grind involves meeting partners, bankers, and investors, but I’m the storyteller, not the executor. My role is about steering the ship, not rowing it.

In a nutshell, my day is a symphony of delegation and strategic focus, ensuring I’m always in my “impact corner.”

I’m not a 9-to-5-at-the-office kind of person. I prefer working from home, though I do pop into the office every other weekend. Even when away, I’m always available, managing calls and emails. Family time is sacred and structured. For instance, when my son turned 13, we embarked on a two-week tech-free adventure in the wilderness, bonding through challenging activities.

I integrate work and family, like taking my younger kids to conferences where they get a vacation while I get things done. We plan several structured family vacations each year. I prioritize these moments. I even take notes in my day-to-day life on things I want to teach them during our one-on-one time, ensuring these conversations are intentional and meaningful.

My approach is highly structured, ensuring these moments are prioritized. My assistant helps schedule and organize, preventing these important family moments from slipping through the cracks.

How do you bring ideas to life?

Bringing my ideas to life is an interesting journey, especially with my dyslexia and ADHD. Communicating my vision can be challenging, but I’ve developed a systematic approach. Instead of planning from A to Z, I prioritize ideas based on their fit within my core competencies and their potential impact. It’s crucial to avoid scattering efforts and ensure that new concepts leverage our existing strengths.

I embrace a rapid testing model—getting ideas to the market quickly, observing results, and refining accordingly. For recent ventures, such as our consulting, debt, architecture, and construction management companies, we launched, tested, learned, and are now coordinating efforts for maximum efficiency. Delegating coordination to someone else when needed ensures a streamlined process.

For more complex ideas, especially those involving technology and long-term execution, I break them down into manageable chunks. It’s a step-by-step approach, allowing for integration and refinement over time. The key is to keep moving forward, building upon each success to reach the ultimate goal. Today, for example, I was reviewing our companies’ feasibility, capital markets, and overall progress, a testament to this strategic, multi-step process.

What’s one trend that excites you?

Exploring AI trends is fascinating, beyond the typical buzz. While the consumer market buzz may have slowed, AI’s impact has been profound and ongoing. Take, for instance, the largest private equity company globally, built entirely on the Aladdin AI platform since 2015.

I see AI less as a consumer product like ChatGPT and more as an integration and processing powerhouse. It disrupts backend operations, closing loopholes, and optimizing efficiency. It’s intriguing how applications evolve by putting a product out, learning from its use, and adapting. Just like ChatGPT, the exploration of language models has triggered innovation across various AI domains.

The real shift in AI impact, especially on the consumer front, may manifest in the next five years. However, the technology has silently transformed everyday lives for years. As with the internet, AI required infrastructure and time to find practical applications. The true marvel lies in the ways AI has influenced people’s lives without them realizing it—playing in the backend, subtly changing how we consume, buy, and more. This, to me, is the captivating essence of AI’s journey.

What is one habit that helps you be productive?

Navigating productivity challenges due to ADHD and dopamine regulation has led me to an effective strategy. Rather than relying on motivation, which can be inconsistent, I focus on creating necessity. Recognizing my difficulty in regulating interest, I establish accountability through meetings and commitments that I must attend.

This intentional creation of necessity removes the need for constant motivation. I find that when I have no choice but to fulfill obligations and meet commitments, my productivity skyrockets. Whether it’s integrating a new business segment or hiring someone to push me forward, the necessity for action becomes non-negotiable. In essence, productivity transforms from an option to a vital necessity in my daily routine.

What advice would you give your younger self?

If I were to advise my younger self, I’d emphasize the importance of thinking beyond the short term. Five years might seem substantial, but in reality, it’s a blink of an eye. I’d recommend adopting a weighted average approach, strategically planning for a 5 to 10-year span, focusing on endeavors with the most leverage even if they bring short-term challenges.

Execution should be the primary focus within the under-5-year timeframe. However, I’d stress that successful execution is a collaborative effort. Trying to go it alone leaves it dependent on fleeting motivation, something I’ve learned is unreliable. So, my counsel to my younger self would be to extend the time horizon, plan thoughtfully, and recognize the power of teamwork for sustained success.

Tell us something you believe almost nobody agrees with you.

I firmly hold the belief that capitalism is the greatest force for good and freedom globally, and all major social advancements stem from it.

It’s challenging for some to grasp, as there’s a prevalent notion that capitalism impedes social progress. Contrarily, I see capitalism as the driving force behind significant advancements. For instance, the Industrial Revolution, catalyzed by capitalism, played a pivotal role in freeing slaves, as economic shifts made their labor unnecessary.

Capitalism, by enabling personal ownership of capital, fostered freedom of thought and choice. This shift in mindset, valuing inherent worth, is a relatively recent development. In the past, even the poor didn’t perceive themselves as having equal value to those above them. Capitalism paved the way for mass social advances, challenging the ingrained notions of inequality.

Contrary to common belief, capitalism isn’t a hindrance to social progress. It’s the very force that dismantled hierarchies and spurred unprecedented advancements in human rights. This perspective might not align with popular opinion, but it’s my firm belief that capitalism, rather than impeding, has been the catalyst for positive societal changes.

What is the one thing you repeatedly do and recommend everyone else do?

One practice I highly recommend, which I find immensely valuable, is reading. I’m a voracious reader, but specifically, I dive into nonfiction—constantly seeking how-to guides and knowledge to enhance various aspects of life. Reading provides a constant stream of learning and growth.

In addition to reading, I believe people should spend more time pondering. Simply allowing your mind to wander and engage in contemplation is a habit often overlooked. It’s in these moments of thoughtful reflection that new ideas and perspectives can emerge. So, my suggestion is a twofold approach: read for continuous learning, and carve out time for intentional pondering to foster deeper understanding and insight.

When you feel overwhelmed or unfocused, what do you do?

When I feel unfocused or overwhelmed, I turn to the outdoors. Taking a walk is my go-to remedy. Stepping outside, immersing myself in nature, and enjoying the quiet surroundings help me regain focus and clarity. Being in an open, serene environment provides the mental space I need to reset and find my balance.

What is one strategy that has helped you grow your business or advance in your career?

When it comes to strategies, we employ different approaches for capital and management. On the capital side, our key strategy is steering clear of speculation. We prioritize cash flow and revenue, focusing on organic growth, revenue compounding, and non-equity functionalities.

For management, the strategy revolves around a learning mindset. We believe in asking what we’re doing wrong and learning from others. We invest time in understanding current perspectives, even if they’re contrary to our own. While we don’t blindly accept external opinions, it’s crucial to consider all viewpoints beyond our own to make informed decisions. This balanced approach ensures a solid foundation for both financial and operational success.

What is one failure in your career, how did you overcome it, and what lessons did you take away from it?

Reflecting on a past deal in Florida, I made a significant misstep. Driven by pride and greed, I pursued the acquisition of a benefits brokerage firm, overlooking fundamental details. I signed a problematic contract, believing we could overcome any issues.

This decision led to a lawsuit and the company’s demise as the owner’s wife took a substantial share of revenue due to a lacking non-compete clause. The aftermath was a public embarrassment and a hard lesson learned.

From this failure, I gained valuable insights. I realized the importance of owning revenue sources to mitigate risks, prompting the launch of companies I now own. This shift in strategy, born from the consequences of that failure in 2010, has proven to be a pivotal moment, contributing significantly to our current success.

What is one business idea you’re willing to give away to our readers?

I think this idea is particularly relevant in the current business landscape. Given the challenges of capital availability, here’s a simple yet effective concept: become a problem solver for business owners.

Sit down with business owners, understand their needs, and propose solutions. For instance, in real estate deals, if a business owner needs $300,000, your role is to find that funding for them. In return, negotiate for equity. This approach allows you to enter the business arena without substantial resources or expertise. It’s a quick way to get started, especially for those who are just beginning.

Additionally, I have another business idea focused on managing and operating AI tools. As the market is flooded with numerous AI tools, many businesses feel overwhelmed and stop exploring them. A valuable business would involve auditing other businesses, implementing existing AI tools, and managing their operations. By becoming an integral part of their business for operations and management, you build a strong and lasting relationship. This business model leverages existing tools, making it a practical and lucrative venture in the AI integration space.

What is one piece of software that helps you be productive? How do you use it?

In managing our businesses, Tenant Inc. serves as our property management company, particularly for storage. We also utilize various software, including management tools like Slack, which are instrumental for coordination and execution. Additionally, Kajabi has proven to be an awesome tool that has greatly benefited our operations.

What is the best $100 you recently spent?

Oh, good question! The best $100 I recently spent was on Storyteller Tactics. These flashcards are a game-changer for both personal and professional growth. They cover everything from structure to style, offering practical exercises to enhance storytelling abilities. You start out with audience profiles and charts, making it incredibly easy and fun to use. The Story Bank feature is fantastic, with various cool components that contribute to becoming a better presenter, seller, and much more. It’s truly a versatile and enjoyable tool.

Do you have a favorite book or podcast from which you’ve received much value?

One of my all-time favorite books is “The Warren Buffett Way.” This compilation offers a wealth of business tactics, advice, and insights, covering everything from fundamentals to advanced strategies, value, hiring, and execution. I first read the original version a long time ago, and it completely blew me away by simplifying complex ideas and introducing unique perspectives on valuation that I had never considered. It’s a must-read for any investor or business enthusiast.

As for podcasts, I highly recommend the All In podcast. It provides an excellent blend of current affairs, investment discussions, and insights into technology trends. It’s a go-to for staying informed and gaining valuable perspectives on various topics.

What’s a movie or series you recently enjoyed and why?

I haven’t caught up on a ton of recent flicks, but one that really stuck with me is “The Revenant.” I revisited it not too long ago, and man, it still hits hard. The cinematography, the storytelling—it’s all top-notch. The way it portrays survival is intense and unforgettable. So, yeah, that’s one I’d highlight, especially for its ability to create such a powerful and immersive experience.

Key learnings:

  • Structured Productive Day: AJ’s highly structured daily routine, even in the face of chronic pain, emphasizes delegation and focusing on what matters most.
  • Work-Life Integration: Prioritizing family time and integrating work with family, AJ shows how structured routines and adventures can create meaningful bonds.
  • Innovative Idea Execution: The systematic approach to idea execution, involving core competencies, rapid testing, and breaking down complex concepts, highlights efficient innovation.
  • Necessity Over Motivation: Creating necessity through commitments and accountability is emphasized as a reliable driver of productivity, particularly when motivation may be inconsistent.
  • Capitalism as a Force for Good: AJ’s belief in capitalism as a positive force challenging the common perception that it impedes social progress is a unique perspective worth exploring further.