When Columbia Business School alumni Jared Toothman ’12 and Syed Ali ’21 first crossed paths, it wasn’t in a boardroom or over a deal. Their connection was forged at alumni events hosted by the School’s Paul Milstein Center for Real Estate. From career forums and conferences to summer socials and monthly market observation calls, the Center provided a steady rhythm of opportunities for alumni to meet, exchange ideas, and build trust.
That foundation proved invaluable when a major investment opportunity came into view. Ali, Founder and Managing Principal of Land Labor Capital, had been tracking a distressed multifamily property on the Williamsburg waterfront initially asking $87.5 million. Recognizing the value and the path to a deal, he sought out a partner with institutional scale that could move decisively. So, he reached out to Toothman, an Executive Vice President at Lincoln Property Company.
The resulting acquisition stands as a testament to the power of alumni relationships cultivated through the Milstein Center, which delivers an innovative, robust, industry-led curriculum through its renowned MBA Real Estate program, and also hosts an industry-specific alumni community with curated opportunities for connection both online and in-person.
“Business is about people, and Columbia’s Real Estate Circle and alumni network makes it easier to build those relationships, said David Sherman ‘82, who serves as Co-Director of the Milstein Center. “That little edge in getting a response or a chance to collaborate is huge over the course of a career.”
From Networking to Closing Deals
Although Toothman and Ali had met several times at alumni gatherings, their first business interaction came in the form of an email early in 2024. Ali, in the early stages of shaping Land Labor Capital into a nimble, entrepreneurial platform, sourced a complex development site that was too large to take on independently. He reached out to Toothman and asked if he might be interested in looking at the deal together.
That proposal ultimately didn’t move forward, but Ali explained that it was “the start of the relationship,” and the two continued to stay in touch, discussing other potential projects.
Ali noted that he had been tracking the property at 56 North 9th Street and recognized that the distressed financing created a time-sensitive opening for the right buyer. After capturing the deal through a brokerage relationship, he reached out to Toothman. The response was immediate. Lincoln evaluated the opportunity and committed within 36 hours—a critical move given the deal’s short timeline.
Building on CBS Roots
By pairing Ali’s sourcing and entrepreneurial initiative with Toothman’s institutional resources, the two were able to unlock a transaction that might otherwise have slipped away. Ali, as the founder of a boutique sponsor, said that one of the biggest challenges is maintaining the flow of information that larger firms take for granted. For him, Real Estate Circle events through the Milststein Center, offered the closest thing to the market calls he once relied on, providing not just knowledge but conviction.
“In a fragmented space like real estate, it's incredibly important to have that flow of information,” Ali said.
Toothman explained that the repeat nature of Columbia’s Real Estate Circle programming—events like the annual Real Estate Symposium in December, the summer networking social, and later the monthly market update observation calls—helped build familiarity over time. That familiarity, he said, created the kind of comfort that makes alumni outreach more meaningful. By the time Ali approached him with an actionable opportunity, he already knew the person behind the email.
“The takeaways here are persistence, networking, and to simply hang around the hoop. If you’re in the right place at the right time when a seller is finally ready to make a decision, that’s when opportunities come together,” Toothman said. Jared has been a member of the Real Estate Circle since he graduated from CBS and is a founding member of the Circle Board.
Lessons for the Next Generation
Their collaboration offers a blueprint for current students and recent graduates looking to build their real estate careers. Both alumni emphasize that outreach to the Columbia community is almost always welcome, even if it requires persistence. “Ninety-nine percent of the time, outreach is well-received,” Toothman said.
Ali agreed, adding that intentionality matters. His advice to those looking to tap into their CBS connections is to approach the network with thoughtfulness, be clear in your outreach, genuine in your interest, and mindful of building relationships that create lasting value for both sides. “The CBS network provides a key that can unlock otherwise inaccessible doors, and it's up to you to walk through them with professionalism and purpose,” Ali said.
Both Toothman and Ali also stressed the importance of developing strong deal instincts. Toothman points out that in real estate, most of the value is created at the point of acquisition, not execution. Having the acumen to source, evaluate, and pursue deals—and having a trusted network to call on—can make the difference between a missed chance and a successful partnership.
The successful acquisition of 56 North 9th Street is proof of concept: CBS connections, nurtured over time, can drive significant outcomes. For the broader community, it’s a reminder that while capital and strategy matter, building relationships remains at the heart of real estate.
FAQs:
Q: Where is 56 North 9th Street located?
A: The property sits in Williamsburg, Brooklyn, one of New York City’s fastest-growing neighborhoods. It includes multifamily residential units with ground-floor retail along the waterfront.
Q: Why is networking important in real estate?
A: Real estate is a fragmented industry where timely information and trusted relationships are crucial. Persistence and thoughtful outreach often determines success more than technical skills alone.
Q: What is the broad takeaway from this deal?
A: In real estate, much of the value is created at acquisition, making both relationships and timing critical.