Shaya Habibi: Entrepreneurship and The American Dream

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While Jamie Dimon may have recently referred to the American Dream as ‘frayed’ in his annual shareholder letter, some believe there is little cause for concern. To understand the current state of the American Dream, one need look no further than the current state of entrepreneurship. According to the US Business Formation Statistics (BFS), the number of business applications filed in 2022 reached a little over 5 million, marking a slight decrease from 2021. Many experts believe that this dip is all but artificial as the 2021 figures were surely inflated by entrepreneurs flocking to open businesses as a part of the pandemic recovery effort. However, in 2023, aspiring entrepreneurs would do well to pursue de-risked opportunities remembering the crypto and NFT market crashes of 2022 and the ever-changing social media landscape.

Simply put, proven strategies and philosophies succeed in all market conditions. Entrepreneurs with old-school work ethics, patience, perseverance, and vision will always be able to realize their American Dream. Shaya Habibi’s personal story and entrepreneurial journey are a paradigmatic example of the American dream, providing a modern blueprint. Recognizing patterns and seeds planted over the course of his childhood, academic career, and early work experiences, Shaya Habibi’s entrepreneurial journey has culminated in a scientific and scalable approach to real estate investing.

Before the revolution, Shaya’s parents immigrated to Chicago from Iran, separately, in 1977. Unfortunately, once the revolution broke out in 1979, they were not allowed to go back and were forced to create a permanent life for themselves in the Los Angeles area, cut off from any remaining family members. Even to this day, Shaya’s parents have not been able to reconcile with many loved ones in Iran. This is precisely why Shaya, his family (his mother in particular), and the entire Iranian-American community are extremely vocal about the current revolution taking place in Iran. Tragically, Mahsa Amini, a 22-year-old Iranian woman, died after being arrested by Iran’s morality police for alleged violations of women’s strict dress codes, sparking what many are calling the first women-led revolution in history.

As a product of a tight-knit Iranian-American family, Shaya was not only taught about morality and to stick up for what is right even when it is difficult, but he was also taught to value education and hard work. These pillars weren’t just ingrained in him, it was expected of him. Shaya recalls, “Growing up in an Iranian household, being a doctor or lawyer were really the only two options presented to me.”

While Shaya was certainly instilled with the importance of getting post-bachelor degrees to set himself up for a prestigious career, he received many important lessons about entrepreneurship during his childhood. Shaya’s mother exposed him to the world of finance early in his life as she was a financial services entrepreneur. Shaya was privy to the ups and downs of this lifestyle in the early years as well as the immense sacrifices his parents made so he could grow up in a wealthy suburb like Calabasas. Calabasas is an esteemed suburb about 30 mins outside of LA known for its celebrity residents. Just by nature of where he was born, Shaya was also exposed to the world of luxury real estate and how it intersects with the rest of the economy from an early age. Specifically, Shaya got a first-row seat to how this former tertiary market evolved into a highly desirable market and then ultimately one of the most coveted zip codes in the country.

When Shaya came of age, it was not even a question of if he would go to college, just where. Shaya would go on to attend the University of California, San Diego where he majored in Management Sciences, a hybrid of economics & finance, and minored in Business and Accounting. Harkening to the pillars of his upbringing, Shaya essentially took on a double major and a double minor with this workload. Further cultivating his work ethic, Shaya graduated at the top of his class.

If that wasn’t impressive enough, Shaya’s flirtation with entrepreneurship couldn’t wait until he graduated. Following his Iranian-American industriousness and his mother’s example, Shaya tried his hand at entrepreneurship while still studying at UCSD. Without any official experience or license, Shaya did everything he could to find a job and a mentor. Developing the seeds of his quintessential hands-on approach, Shaya drove around the city looking for the numbers of residential brokers on ‘for sale’ signs outside of homes. After calling hundreds of residential brokers in a given outing, Shaya was able to work through and with many residential brokers in the region in an unofficial capacity. This taught Shaya the importance of being relentless in entrepreneurship early in his career. Eventually, Shaya secured a mentor, who he is still friends with to this day. Shaya helped out in any way he could as he knew the importance of gaining first-hand experience in the industry. As a natural go-getter and willing to check his ego, Shaya drove his mentor around, painted, and did whatever was asked of him as Shaya watched him fix, flip, and sell houses as well as network. Shaya even worked for free knowing his parents would want him to focus on his education and not work.

Shaya was encouraged to work during the summers, however. After interning at a CPA firm and impressing the founder of the practice, Shaya expressed his interest in working at one of the Big Four accounting firms: Deloitte, Ernst & Young (EY), KPMG, and PricewaterhouseCoopers (PwC). The Big Four got their name and positive reputation in the industry due to their consistency, scope of services, and frequency with which they work with Fortune 500 companies. Shaya understood that accounting is the language of business and if he wanted to be a successful entrepreneur getting a CPA license and experience working at one of the big four would help him along his journey. During the financial crisis, when the world was reeling from unemployment, Shaya defied the odds and beat out thousands of people from the job when it was at its most competitive (10x difficulty). In a feat unheard of at the time, Shaya landed the single spot in the division he applied to at PwC right out of college. During his time at the firm, Shaya became fluent in the ‘language of business’ and continued to grow his network.

Eventually, Shaya went to a Tony Robbins seminar to find some additional inspiration, guidance, and strategies to pick a lifelong career that doubles as a calling. In a moment where hard work met destiny, Shaya was talking to a conference representative who pointed to a somewhat unassuming man with long hair wearing a hoodie and a necklace and said, “That man is a real estate mogul.” During this time, Shaya was just out of college and starting to get into fixes and flips, so the timing felt divine. Paradigmatic of his upbringing and work ethic, Shaya had been walking around neighborhoods at all hours of the day going door to door offering to purchase houses trying to find the peak time to get an offer. Now, in a stroke of fate, just as he was in the process of getting his real estate license, Shaya found himself at the same inference as Ari Rastegar, the aforementioned real estate mogul. Realizing that Ari was his ideal partner for the conference’s famous fire walk, Shaya went over to Ari to abruptly and aggressively inform him — not ask him — that they were going to be partners. Ari said yes, responding to his confidence and immediately kicking it off with similar core values and culture, speaking fluent Farsi to each other as both Shaya and Ari are Iranian Americans.

After the conference, Shaya embarked on a 3-year, 24-hour a day, apprenticeship working directly for the Founder and CEO of Rastegar Property Company, a technology-enabled private real estate investment firm. As a part of this apprenticeship, Shaya traveled across the country with Ari to source & finance deals, raise capital, and be a part of all of the nuances of running and scaling a private real estate investment firm. This demanding and unique experience did not only teach Shaya specific lessons about the real estate industry, but also gave him a model for how to be a successful entrepreneur. Shaya learned the necessity of checking one’s ego, committing to always bettering oneself, developing patience, being willing to exert an inhumane level of grit, and striking when the time is right. Ultimately, before his apprenticeship with Ari, Shaya was not ready to succeed as an entrepreneur on his own. This is not to say he wouldn’t have ultimately found success, however, by systematically preparing for his future with Ari, Shaya set his career on the right path and cultivated a very fruitful relationship. To this point, this experience gave Shaya an intimate understanding of why it is arguably more important to cultivate and nurture relationships than it is to develop knowledge and skills. Also, by living with Ari, his wife, and two children, Shaya got a crash course in how Ari managed his professional obligations with his personal and familial life. These lessons inform Shaya’s professional and personal life to this day as he still has a close relationship with Ari.

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“Shaya was confident enough in himself to exhibit great humility to learn through perfecting seemingly menial tasks in order to build himself into the man he was destined to embody. I couldn’t be more proud of his evolution and commitment to constant improvement,” Ari fondly states about Shaya.

During his apprenticeship with Ari (dubbed the Oracle of Austin by Forbes), Shaya began recognizing patterns from his childhood and previous work experiences. Recalling the Calabasas real estate boom he partially witnessed at a young age as well as the thriving real estate markets in the suburbs surrounding San Diego like La Jolla, Shaya had a life-changing eureka moment. Habibi realized that what was happening in the suburbs outside of Austin reminded him how the suburbs outside of LA and outside of SD developed into tourist destinations with their own ecosystems and micro-economies over the last 2 decades.

Now, as Austin becomes a major destination for startups, investors, and even celebrities, Shaya’s bet on the surrounding suburbs is paying off. To this day, Shaya never lost his hands-on and grounded approach. In over 30 different houses he’s been involved with, Shaya works alongside the contractors or walks on the site on the property to ensure that the quality control is done at the level that he sees fit to create value. Even though Shaya has found the entrepreneurial goldmine, a scientific and scalable process, Habibi is making sure he grows the company sustainably and in the right way. To ensure alignment of interest and value with his investors, Shaya is deliberately moving slower than others who solely rely on investor capital so that he can personally invest in these properties as well.

As Austin’s real estate scene and economy continue to thrive since its post-pandemic renaissance, we are excited to see how Shaya Habibi progresses along his entrepreneurial journey. To learn more about Shaya, his thoughts on real estate investing, and to get a firsthand look at his work ethic & values, check out his instagram here.

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