Dennis Cisterna


If you have been to a real estate investment conference in the past 15 years, chances are you have heard Dennis Cisterna on stage speaking about everything from the history of the housing market to the future of the economy and everything in between.

How Numerous Shifts Finally Led to Career Fulfillment

If you have been to a real estate investment conference in the past 15 years, chances are you have heard Dennis Cisterna on stage speaking about everything from the history of the housing market to the future of the economy and everything in between.

He has been a leading voice in this industry since the Great Recession and his insights have made a lot of firms a lot of money over the past 20+ years.

Since the beginning of his career in 2000, Cisterna has completed more than $3.7 billion in real estate transactions in the US and Europe, but he only ended up in real estate due to a chance meeting in college.

On His Way

As an undergraduate at San Diego State University, Cisterna had his eyes set for another field entirely — politics. While interning for a mayoral candidate in San Diego, he met the campaign’s fundraising chief and was given a quick tutorial on what drives elections (money) and what many of the candidate’s largest donors had in common — real estate.

San Diego State University

Cisterna noted, “When I was in college, the most popular path to elected office was to begin your career as an attorney, but I saw the writing on the wall — your network could matter just as much as your net worth and since I wasn’t truly excited about practicing law and I had always found real estate intriguing, I made a career shift before actually starting my career.”

Cisterna was able to land an internship at real estate market research firm The Meyers Group (now Zonda), where he was mentored by some of the industry’s sharpest minds such as John Burns and Tim Sullivan. Like most in their first real job, Cisterna said he was “absolutely clueless but worked extremely hard and asked a million questions” and was offered a full-time role as an analyst a couple months before graduating college.”

After four years of writing research reports and traveling all over the country performing feasibility studies for new development projects, Cisterna wanted to make a switch to learn other aspects of the investment and development industry. He took management positions with iconic homebuilders Lennar and Toll Brothers to help expand each company’s footprint in Southern California.

Lemonade Out of Lemons

He achieved immediate success with both firms, but the housing crisis took his career on a detour he never expected. “I went from an emerging leader with a Fortune 500 company to collecting unemployment checks,” he recalled, adding that his division at Toll Brothers went from 160 employees to 16 during the Great Recession. As the world worked itself through the housing crash, Cisterna scrambled to survive in an industry he had grown to love.

Shortly after being laid off, he started an advisory firm that had him take on every type of assignment under the sun and broadened his skill set immensely. He consulted dozens of the biggest financial industry players, including several of the largest banks in the country, about how to manage their swelling book of foreclosed homes, commercial properties, and large tracts of land.

On the other side of the coin, Cisterna also advised large private equity firms and hedge funds how to capitalize on the distress in the market.

A Passion for Evolution

After making a name for himself among some of Wall Street’s biggest names, Cisterna transitioned to real estate investment banking and lending with executive positions at several firms including Johnson Capital and FirstKey, where he was recognized as a leader in bringing new equity and debt to the then burgeoning asset class.

“I found I had a great knack for raising capital and understood the momentum for SFR investing was trending in the right direction. It was pretty exciting being on the ground floor of the SFR investment space and being a major part of how the capital markets evolved.”

In 2016, he moved to Investability as the company’s Chief Revenue Officer and was selected to serve as the CEO of the company barely a year later. But he still felt unfulfilled. “I always had this vision in my mind that once I became a CEO, I would be satisfied, but achieving that left me more frustrated than I had been before. It dawned on me that even as CEO, I did not own the company. I still had a board of directors to report to, there was a corporate culture that preceded me, and it was not nearly as appealing as it seemed on the road up the corporate ladder, so I got off the ladder. It was surreal to spend nearly 20 years working towards a goal, achieving that goal, and realizing that isn’t what you really want.”

From Zero to $600 Million

With a little nudging from some industry colleagues, Cisterna did take that chance on himself. He launched his own investment firm, Guardian Residential, in 2018. The firm focuses on niche off-balance sheet financing opportunities with homebuilders.

Guardian has deployed nearly $50MM with several builders across the country. Six months later, he co-founded build-for-rent operator, Lafayette Communities, with industry veteran, Thibault Adrien. The firm is backed by private equity giant, Carlyle Group, and has more than 2,000 units either built or under development in the southeastern United States.

In late 2019, he co-founded Sentinel Net Lease with another longtime industry colleague, Fred Lewis. Sentinel acquired stable cash-flowing commercial real estate across the country. Their roster of blue-chip tenants includes Amazon, AT&T, JP Morgan, and Tesla. The firm currently owns 15 assets totaling over $225 million with an eye on crossing $500 million by the middle of 2023.

When pressed to explain the meteoric rise of his entrepreneurial efforts – Cisterna isn’t shy in his explanation.

“I’d love to tell you I am the smartest guy in the room, but it is really a combination of luck and timing. My collective experience over the past 22 years has helped me identify investment opportunities in the early stages and we’ve capitalized on that across all three platforms, but I could not have succeeded in this manner if technology and information hadn’t become accessible to an emerging investor like me.”

“So many of the innovative tools and services that were built for the largest investment firms are now available to investors of any size. As you can imagine, if I own a real estate-services company and I’m trying to grow my revenue, once I’ve captured the institutional sales I then must go downstream to the next level of investor. That trickle-down effect in products and services for real estate investors benefits every investor at every level.”

“From capital raising to data analytics to asset management, it might be the easiest time to start an investing firm in the history of the US. Of course, that doesn’t mean making the right investment decisions are easy, but the barriers to entry are now so much lower than in the past.”

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