AJ Osborne, the visionary behind Cedar Creek Capital, recently launched the podcast “Saving Capitalism.” In the episode “Pro Skater to Entrepreneur,“ Osborne discusses how to become an entrepreneur and succeed in today’s economic climate with former pro-skater turned entrepreneur, Mikey Taylor.
In this podcast conversation, Osborne began by addressing the biggest barriers to becoming an entrepreneur and concluded by focusing on how to find real-estate opportunities in today’s inflationary market.
Find Your Mentor
For both Osborne and Taylor, one of the key milestones in their respective journeys was to find mentors that could break down complicated concepts into simple takeaways. As they elaborated, find the person that can explain novel ideas “as if talking to a child,” because that person will demystify their approach, and make you realize that success in a given field is not as complicated as others would have you believe. In other words, learn in real-time from your mentor, then you can branch out on your own.
Simplify Your Message
Finding a way to articulate your message in a clear, concise way is also a skill that will serve you once you become an entrepreneur. This episode delved into a real world example from the 2016 presidential election: On the messaging side, there was a wide gap in the level in which the two candidates spoke. Donald Trump spoke at a first-grade level. Hillary Clinton spoke at a sixth-grade level. According to experts, speaking at a sixth-grade level was too advanced to reach the widest audience, which tends to be more persuaded by second-grade level messaging.
“Most people are hungry for that kind of simplicity,” said Osborne. “That’s the reason people listen to this podcast. They’re trying to understand how the world works, how it affects them, and how they can perform better in it.”
Learn From Challenging Market Conditions
One of the trickiest parts of becoming an entrepreneur is having to learn “in real time” from your mistakes. But diving into the deep end of the pool, especially during challenging market conditions, gave Osborne and Taylor the best training ground for success. From 2008 to 2013, both of them learned from the Recession and its aftermath. As Osborne explains, “I love being asked, ‘How did you learn about macroeconomics?’ My response is always, ‘I was consulting with 300 companies that were failing during the financial crisis, and I spent years trying to figure out why.’”
As he went on to elaborate, “Wisdom comes from stepping out of the day-to-day micro adjustments you have to make as an entrepreneur and seeing the larger play at work. What really moves the needle on investments is a combination of micro-actions and larger time frames.”
In sum, Osborne advises to not be so focused on your own asset class or product category, but to also take into account the larger macroeconomic conditions.
Thinking Differently is an Advantage
Osborne and Taylor had to overcome feeling like outsiders to succeed in their respective fields. Eventually, they both discovered that their uniqueness actually afforded them a huge advantage. Osborne related the story of how he had to overcome ADHD and dyslexia.
After graduating from high school, he wanted to become a professional skier. “I had this narrative in my head of, ‘Oh, I’m dumb, so this is all I can do,’” Osborne said.
But he was able to overcome that narrative when he enrolled in college and eventually discovered that he could not only survive but thrive in intellectual circles. That’s why Osborne encourages everyone to become financially literate. He explained, “From an early age you’re taught, ‘Don’t talk about money. Don’t ask how much people make.’ And all of a sudden, you’re thrown into a world of money. It’s a shock to the system. But frankly, the tail is wagging the dog, meaning the economy is actually driving everything, from social issues to politics. It’s this massive all-encompassing thing that everyone doesn’t know how to talk about, and I think that’s very dangerous.”
That’s one of the reasons Osborne launched his podcast “Saving Capitalism,” to educate the public on economic issues.
How To Take Advantage of Current Market Conditions
Osborne addressed the current state of the economy, which he predicts will likely continue going through an inflationary period. He and Taylor also agree that heavy regulation has disproportionately hindered small businesses, allowing larger films to swallow them, and that, in turn, has created more monopolies.
But there are still opportunities to thrive in this challenging market. For one, the barrier to privileged information has begun to break down thanks to outlets like YouTube and TikTok, allowing leaders in their respective fields to educate swaths of people that previously didn’t have access to expert advice.
Specific to real estate, Osborne recommends entering markets where there is high demand but low supply, and a high barrier of entry for contractors or landlords. It means not chasing the “hot market,” but going after those that are not becoming saturated with new builds.
“The future holds challenges and opportunities alike,” Osborne reflected. “Embracing change and staying informed are integral elements for ensuring success and resilience in the ever-evolving real estate market.”
About AJ Osborne
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
