With Big Plans in Mind, Josh Joseph and His Family Are Changing the Industries You Interact With Daily

With real estate deals, cannabis companies, cannabis operators, and hospitality as pillars in the group’s holdings, Joseph’s career experience is one to learn from

At 35 years old, Josh Joseph hit a pivotal point in his career: He could either take a chance on himself as an entrepreneur or find an opportunity that would offer stability and security. Unsure what to do, he called his dad, who owned his own accounting firm, for advice.

“If I could do one thing differently, I’d believe in myself earlier,” his dad said. “Invest in your talents, trust yourself and your family, and take the risk.”

Up until that point, Joseph had been working in the real estate industry, building a career that he had been dedicating his life to for nearly 15 years. Starting out at his cousin’s small law firm, Joseph did legal clerking work to get a look into the life of a lawyer and decide whether he wanted to pursue law school. In less than a year, it became clear that law school wasn’t the right move but, fortunately, that same cousin had a commercial real estate business and gave Joseph the chance to try his hand at something other than legal work.


During his first five years working in real estate, Joseph was exposed to a wide range of transactions: He supported the marketing and sale of properties, worked with distressed assets, and supported retail real estate transactions from start to finish. As he began to specialize in bankruptcy and distressed deals, Joseph worked with clients in many different geographical locations and industries, essentially becoming an industry- and location-agnostic retail real estate expert.

Equipped with vast experience and a specialized skill set, Joseph took a new opportunity at Hilco Real Estate, where he stayed for nine years. He flew to clients around the nation liquidating companies, buying distressed assets, and helping execute complex, strategic real estate deals. In that time, Joseph was involved in everything from multifamily properties to industrial sites, office spaces, and even land. Overcoming challenges like repositioning a failing dairy farm’s assets exposed him to numerous business dynamics, professional relationships, and different asset types. To Joseph, this was the most instrumental opportunity of his career because it prepared him to learn new industries quickly, solve evolving business problems, and work with many types of people. 

2008 and 2009 were notoriously challenging years for businesses and individuals alike; the market tanked, financial transactions were volatile at best, and people were panicked. Because of the positioning of his role, Joseph weathered the storm well. There were many businesses that needed bankruptcy and restructuring support, and he was one of the best in the country at doing just that. But still, the pressure was intense.

Josh and Tara Joseph


It was 2010 when Joseph called his father and asked for advice, and because of that advice, he opened a new real estate firm with the help of two business partners. Although his wife, Tara, was hesitant to take on the risk associated with entrepreneurial ventures, she stood by him.

Joseph had a lot to learn as an entrepreneur, but in the world of real estate, he was a force to be reckoned with. The legacy he left behind was that of $1 billion in total brokerage transactions, deals completed in over 40 states, and the acquisition, development, and sale of properties in nearly every asset class. In 2014, his ability to navigate new markets and industries shifted his focus to a controversial business opportunity: cannabis.


Illinois’ governor at the time had just passed a medical pilot program for cannabis, opening up medical retail licenses in a lottery system. Joseph’s business partner was eager to get on the cannabis train early, but like many other entrepreneurs and business professionals, Joseph was hesitant. The market was unpredictable, cannabis was and still is illegal at the federal level, and a business undertaking of this type was sure to come with unforeseen risks and challenges beyond Josh’s experience level.

Eventually, his natural curiosity and confidence in his own business prowess won, and Joseph and his business partners applied and won seven of the first 50 medical retail licenses in Illinois, giving themselves the largest market share in the state. Only the 11th state to offer a program of this kind, Illinois opened up new opportunities for those bold enough to jump in. Almost an act of fate, at the same time the trio won licenses in Illinois, a distressed growing and manufacturing facility in Las Vegas reached out for support.

The facility was hemorrhaging cash and its ability to survive was in question. Acting fast, Joseph and his team swooped in, raised $1.25 million, and bought into a minority position, expanding their reach to multiple states. Within three weeks, the three partners won licenses in Maryland and Pennsylvania as well, opening nine of the first 81 stores in Pennsylvania, along with a dispensary and grow facility in Maryland.

In less than six years in business, Grassroots Cannabis, held by GR Companies Inc., went from being a four-person operation to an employer of 1,200 people with a presence in 12 states. However, the industry was considered the “wild west” by many, and professionals were nervous about getting too close. Lawyers didn’t know the implications of working with a federally illegal product, salespeople weren’t ready to attach their names and reputations to cannabis, and states were often writing the rules as they went, making business channels even harder to navigate.

Despite all the forces working against him, with the support of his partners and his family, Joseph prevailed. In 2019, Grassroots Cannabis entered into acquisition discussions with Curaleaf, the largest cannabis company in the world. By March 2020, when the pandemic hit, the deal still had not closed. Joseph was burned out and ready for a vacation, but like everyone in 2020, vacations were off the table. Eventually, in July, the deal closed for $850 million.

Josh with his wife Tara and their daughters, Sophie and Sydni


There was no time to celebrate Grassroots Cannabis’ astounding exit and, like any good entrepreneur, Joseph got right back to work. His eldest daughter, Sydni, who had just graduated from college with a high-end event production job lined up, found herself jobless because no events were taking place. Taking a chance on more than just himself this time, Joseph asked Sydni, Tara, and their youngest daughter Sophie to pursue a joint venture. But, to cover his bases, he promised a “no strings attached” arrangement: If anyone ever wanted out, they could leave, at least at first.

Now, three years into operating Big Plan Holdings, Joseph jokingly admits that his daughters and wife are too valuable to ever leave. Together, the family has broken into entertainment, sports, music, high-end fashion, and even a philanthropic endeavor called the Joseph Family Foundation.

What started out as the deployment of capital into businesses turned into an empire because of Tara’s commitment to building a brand, connecting with the community, and creating a presence in Nashville.

With real estate deals, cannabis companies, cannabis operators, and hospitality as pillars in the group’s holdings, Joseph’s prior career experience comes into play on a daily basis. Recently, the family successfully finalized branded partnerships with Hank Williams Jr. and Jon Bon Jovi for bars and restaurants in Nashville. Now, they are looking forward to collaborating with Major League Baseball players and NBA stars. Going even further into uncharted territories, Big Plan Holdings supported an entertainment docuseries that will be on Paramount Plus in the next year.

Big Plan Holdings’ headquarters in Nashville, TN


When Joseph and Tara started dating in the eighth grade, they had no idea where their lives would take them. Joseph didn’t know he would have a knack for real estate, cannabis, or business development overall; Tara couldn’t have predicted ever going into business with her husband and daughters. But it all came together in a way that exceeded everyone’s expectations. Joseph has become an innovative business leader, but he’s also opened the door for the people he loves, just like his cousin did all those years ago.

Josh Joseph

Founder & CEO | Big Plan Holdings


Chicago, Illinois

University of Illinois

Early Career
Real Estate

Big Plan Holdings


Nashville, Tennessee