John Leggett: From Investment Banker to Visionary Entrepreneur

John Leggett’s journey from investment banking to entrepreneurial success shows the power of resilience, calculated risk-taking, and adaptability. He started his career in 2001 after graduating from the University of North Carolina, and started by immersing himself in the world of mergers and acquisitions. These years in investment banking gave him the financial acumen to analyze deals and assess risks effectively, but his aspirations took him to finding his own path. “I always kinda knew I was gonna do my own thing,” he recalls.

After three to four years in finance, Leggett decided to take the leap into entrepreneurship. Putting his savings and bonuses on the line, he left his job in the corporate world and began looking at opportunities in real estate and travel. The transition was not without its challenges. He highlighted that every entrepreneur faces hurdles, with capital often being the most significant. “For every entrepreneur, the challenge is gonna be capital,” he explains. “And risk tolerance is a big one.” Sacrifices were inevitable, especially in balancing work and personal life. “You get to make your own schedule, but it comes at the sacrifice of a lot of things,” he adds.

Throughout his journey, Leggett had support from his family and mentors. His father, a pilot who ventured into real estate, and his father-in-law, a urologist who took significant risks to establish his practice, served as models of entrepreneurial grit. Leggett’s wife was also always on his side from the beginning. “Without their influence and support, I don’t know if I’d have had the confidence to take the leap,” he admits.

As an investor, Leggett has developed a disciplined approach to identifying opportunities. His philosophy centers on seeking asymmetrical returns, where downside risks are minimized, and upside potential is significant. “We don’t want 0 to be an option,” he explains. Over time, his focus has shifted from high-risk ventures to calculated investments in sectors like real estate, oil and gas, and infrastructure—industries he describes as “boring but reliable.” His preference is for investments that can generate cash flow and provide clear monetization opportunities within three to four years. “If we can’t explain it in 60 seconds or less, we probably shouldn’t do it,” he says.

Risk evaluation is an important part of Legget Venture’s strategy. Leggett says that its not only the financial risk of the deal but the amount of time spent is also factored. “Time is a resource, and if it’s tied up in one deal, it can prevent us from pursuing other opportunities,” he explains. Leggett Ventures has built a reputation for catering for the interests of its investors by investing heavily in every deal. “If it doesn’t work, it’s painful for us, which shows our investors how committed we are.”

Leggett offers candid advice for aspiring investors. He tells young aspiring entrepreneurs to understand their risk tolerance and based on that see whether they can handle being an entrepreneur. “Are you willing to risk it all? Are you ready to work seven days a week?” he asks. Additionally, he emphasizes the significance of scalability, recommending business owners to think about how their company will develop and who might potentially purchase it. “Thinking about the exit early on is super important,” he says.

Leggett emphasizes the significance of knowing one's risk tolerance and matching assets to individual objectives for investors. He suggests avoiding the lure of get-rich-quick scams and distributing money over a variety of options. “Patience is key, and things almost always take longer than expected,” he cautions.

Leggett also believes that technology has the ability to change things. Citing applications like financial analysis, architectural drawings, and simplifying corporate processes, he views tools like AI as revolutionary for efficiency and creativity. “AI is reshaping the world, and anyone who doesn’t embrace it is missing out,” he states.

Looking ahead, Leggett sees a future of continued growth and meaningful investments for Leggett Ventures. He emphasizes the importance of maintaining flexibility and focusing on quality over quantity. “If we don’t do a deal for six to twelve months, we’ve got no problem with that,” he explains. While he hopes to slow down eventually, his energy and passion for his work remain as strong as ever. “Right now, I’m super excited to get to work every day,” he says.

The success of accepting change, taking measured chances, and remaining loyal to one's goal is demonstrated by John Leggett's narrative. When it comes to mentoring new business owners, looking into fresh investment prospects, or using technology to remain ahead of the curve, Leggett is the definition of a visionary leader who is constantly willing to change and grow.

The Six Degrees team extends our gratitude to John Legget for taking the time to share his inspiring story and perspectives. We are excited to watch Legget Ventures grow and continue shaping the future of entrepreneurship and innovation!