For Dennis Cisterna, the transition from the corporate world to entrepreneurship wasn’t just a leap of faith—it was a calculated move born out of a desire for independence and a drive to provide unique opportunities to everyday investors. As the co-founder and Chief Investment Officer of Sentinel Net Lease, Dennis has spent the last several years reshaping the way individual investors access commercial real estate, all while navigating the volatile markets and challenges of entrepreneurship.
In a candid conversation, Dennis shared his story of taking control of his career, lessons learned from corporate life, and the passion that drives his work today.
A Unique Mission: Bringing Wall Street to Main Street
Dennis co-founded Sentinel Net Lease with a clear mission: to give individual investors the chance to participate in large institutional real estate deals that were traditionally out of their reach. “I wanted to offer people like doctors, dentists, and CEOs access to opportunities they wouldn’t typically have,” he explains. “Historically, if they invested in real estate, it would be at a granular level—maybe buying a rental property or investing in a real estate investment trust.”
But Dennis’s vision was different. He wanted to bridge the gap between Main Street and Wall Street, offering investments in large-scale commercial properties. “We’re talking about $20, $30, $50 million deals,” he says. “For most people, these kinds of opportunities are out of reach, but I wanted to change that.”
Since its inception, Sentinel Net Lease has acquired over $300 million worth of commercial real estate across 13 states. Dennis and his team have also launched their first investment fund, aiming to raise $100 million and offer diversification to investors during a time of rising interest rates.
The Path to Entrepreneurship: A Leap from Corporate Comfort
Despite the impressive success of his firm, Dennis admits that the decision to leave the corporate world was not an easy one. “I spent 20 years climbing the corporate ladder,” he recalls. “I became a CEO, and while I had a great paycheque, it wasn’t as fulfilling as I thought it would be. I still had a board of directors to report to and a whole host of other problems.”
The disillusionment with corporate life grew stronger until he realized he wanted something different—control. “Reaching the top of the corporate ladder actually convinced me to get off it,” he laughs. “I wanted to bet on myself.”
Betting on himself wasn’t just a spontaneous decision. Dennis was methodical. “I gave myself 18 months,” he says. “I had enough savings to invest in my idea, and if it didn’t work, I could always go back to being an executive. But the regret of not betting on myself would have been too much.”
Lessons from the Early Days: Learning to Lean on Experts
Starting a business comes with challenges, even for someone with Dennis’s experience. Looking back on the early days of Sentinel Net Lease, he acknowledges a few missteps. “You don’t know what you don’t know,” he reflects. “I thought I was wide open to the challenges, but there were some things I wasn’t prepared for.”
One of the most critical lessons he learned was the importance of bringing in the right experts. “I’m a big-picture guy, and I’m great at acquisitions, but I’m not a ‘dot the i’s and cross the t’s’ person,” he admits. “I waited too long to bring in someone to help me with the organization and infrastructure. I probably lost six months of progress because of that.”
Dennis emphasizes that knowing your weaknesses is essential for any entrepreneur. “When you’re starting out, you’re not always thinking about your blind spots, but they’ll catch up with you if you don’t address them.”
The Core Attributes of a Successful Entrepreneur
Reflecting on his journey, Dennis identifies three key traits that every successful entrepreneur must master: risk management, passion, and work ethic.
- Risk Management: “Every entrepreneur has to have a tolerance for risk, but it has to be measured risk,” he says. “It’s not about being reckless, but about understanding the risks you’re taking and being willing to manage them.”
- Passion: For Dennis, passion doesn’t necessarily have to be about the industry you’re in, but about the work itself. “You see entrepreneurs who are passionate about disrupting their industries,” he explains. “That passion drives them, whether they love the industry or just the idea of changing it.”
- Work Ethic: “When you’re an entrepreneur, your success or failure is entirely on you,” Dennis says. “That level of accountability pushes you to work harder than you ever have before.”
Overcoming Challenges: Lessons from the Great Recession
For Dennis, one of the most significant challenges in his career came long before his entrepreneurial journey began. In 2008, during the Great Recession, he found himself laid off from a promising role in the homebuilding sector. “I was newly married, with a kid on the way, and I had just bought my first house,” he recalls. “Suddenly, everything I had planned was gone.”
That experience shaped Dennis’s career in profound ways. “It taught me that I needed to be so invaluable and so knowledgeable that if something like that ever happened again, I could immediately pivot to something else,” he says. “I realized that I needed to learn everything I could, so I spent the next several years flipping houses, consulting for banks, and learning about mortgage-backed securities.”
This adaptability and thirst for knowledge have been instrumental in Dennis’s entrepreneurial success. “That experience taught me never to take my foot off the gas when it comes to learning and identifying risks,” he says.
Scaling the Business: The Road Ahead
Today, Dennis is focused on scaling Sentinel Net Lease, but it’s not without its challenges. Having raised nearly half of his $100 million investment fund, he now faces the task of raising the remaining $55 million from investors who may not be familiar with him or his company. “I’ve tapped out the people I know,” he admits. “Now I have to build trust with a cold audience.”
To overcome this challenge, Dennis is turning to thought leadership and data-driven strategies. “It’s about people understanding our strategy and our past successes,” he explains. “We’re focusing on building trust and being transparent.”
In addition to growing his fund, Dennis is also keeping an eye on the future of his industry. “The real estate market is always evolving,” he says. “You have to keep adapting your playbook. What worked in 2020 doesn’t necessarily work today.”
Final Thoughts: Betting on Yourself
For Dennis Cisterna, entrepreneurship is about more than just building a business—it’s about taking control of your life and betting on yourself. “I wish I had done it sooner,” he admits. “But I’m glad I finally took the plunge.”
His journey is a testament to the power of risk-taking, passion, and resilience. For aspiring entrepreneurs, Dennis offers a simple piece of advice: “Know your strengths, acknowledge your weaknesses, and always be willing to learn. And most importantly, don’t be afraid to bet on yourself.”
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