Michael Shah just wrapped a career-defining acquisition binge, closing nearly $400M in deals over six months — a stunning reversal for an investor who found himself putting a piece of his business into bankruptcy less than three years earlier.

As others hit by the very same distress find themselves bickering with lenders and clinging to bleeding assets, the CEO of Delshah Capital is in comeback mode, backed by some of the largest names in the business. 

“It was like I've trained my whole life for this sprint,” Shah told Bisnow in a Zoom interview Friday.

Back in 2023, Shah was eyeing down $59M in Israeli bonds coming due in September and was on track to sell 55 Gansevoort St., a boutique hotel in the Meatpacking District, to repay the debt. The firm reached a contract months earlier, but the buyer got cold feet, leaving Delshah’s financial future in question.

Shah had spent his career building a roughly $1B portfolio, spanning federally subsidized affordable housing complexes, luxury retail, ground-up condo development and debt. One looming deadline put it all at risk. 

The situation took a toll on more than Delshah’s balance sheet. Chad Roberson, Delshah's then-head of capital markets, took his own life in 2024, Shah said. 

“I wish he was still around for the comeback, but I guess he felt pretty hopeless,” he said. “I happened to be lucky enough to have figured out that money and success aren't everything, but the people that you really care about are.”

Lessons

Early in the crisis, Shah called two people: LIHC Investment Group principal Charlie Gendron and Ziel Feldman, founder of the now-defunct HFZ Capital Group. 

Feldman faced his own set of troubles after his partner, Nir Meir, allegedly used the firm to conduct an $86M fraud scheme. Meir has pleaded not guilty and is scheduled to face trial in October. Meanwhile, Feldman, who wasn’t implicated in any wrongdoing, was left to pick up the pieces and move on with his career.

Shah crossed paths with Feldman years earlier while working on a deal for 40 Broad St. 

“I asked Ziel what he did to keep himself sane when HFZ was imploding,” Shah said. “He gave me really good advice: Spend half your day figuring out the problems. Spend the other half of your day thinking about new business and other things.”

Then, while building his business back up, Shah encountered Gendron.

“His whole approach to business is that he tries to help his transaction partner achieve whatever is most important to them, and then he finds that things usually work out for him,” Shah said.

Acts of compassion can be rare in the cutthroat culture of New York City real estate. As Shah put it, the mentality in the industry is oftentimes “$1 for you is $1 less for me.”

With so much money at stake, it's why lenders are quick to battle defaulted borrowers, why buyers squabble among each other, and why some investors hang on for dear life. It’s why the average real estate attorney’s rate nears $1K an hour, with New York's elite litigators commanding much more. 

“I’ve brought enough foreclosures to know that inevitably you lose, but it costs the lender a lot of money. The asset value drops in the interim. Tenants leave,” Shah said. “Everyone's just shrinking the pie instead of helping each other out.”

“I’m almost 50,” he added. “Life is way too short for that.”

Recovery

Shah filed two prepackaged bankruptcies in late 2023. Doing so bought time, holding off the bondholders’ trustee from seizing control of his company, while speeding up a prior deal to sell 100 Christopher St. 

Unlike a traditional bankruptcy filing, a prepackaged deal is largely negotiated in advance. The process is faster, more predictable and comes at a lower cost. 

“We were able to get our creditors meaningfully more money, millions of dollars more, than if we had just handed them the assets back,” Shah said. “Anybody that we got a chance to explain what we did there was really appreciative.”

Shah launched himself into negotiations. Signature Bank, his biggest lender, had collapsed months earlier. Pieces of the loan book were sold off, with Blackstone, Rialto and Related becoming Shah’s new debt servicers. 

With Related, he worked out a restructuring deal. Blackstone and Rialto agreed to sell Shah’s debt back to him. 

“Irrespective of whether it was me or someone else, they weren't going to get 100 cents on the dollar,” Shah said. “They were cognizant that the owner is usually the highest-value buyer.”

Then Shah turned to Park Hill. The 1,100-unit Staten Island apartment complex had been in his family for decades. Shah had owned the eight-building campus for more than 20 years, originally acquiring it from his father. 

In February, Shah sold the property to Arker Cos., L+M Development Partners and LIHC Investment Group for $364.7M. 

The affordable housing developers spent months in negotiations, bidding against one another. Then, Shah did something “really crazy.”

“Rather than continue to have them bid against each other, I put them all together and said, ‘Look, buy it all together. I don't want to see any of you get screwed. You guys are all really great people. You put a lot of work into it. I don't need any more money,’” Shah said. 

The city and state requested that the developers buy out Shah completely, even though he originally wanted to keep a stake in the property. The building had generated more than 2,000 tenant complaints in recent years, Crain's New York Business reported.

The move resulted in the new ownership paying Delshah “a very fair price, even though, at that point, they didn’t really have to,” Shah said. 

On The Clock

Park Hill established Shah as a significant property owner and allowed him to start buying notes in the 2010s. Now, its sale is providing his firm with the liquidity needed to fuel his next era. 

Shah brought on Michael Bacon, a longtime friend, as executive managing director and head of capital markets and acquisitions. Bacon spent 15 years as the chief operating officer of a family office in Dubai and will now be overseeing family offices’ investments in Delshah.

After the Park Hill sale closed, the 1031 exchange timer began ticking. Delshah had 180 days to reinvest the proceeds to defer capital gains taxes.

Shah, with Bacon at his side, went shopping. 

“We did crazy stuff to get deals done from sellers that were on the fence,” Shah said.

That includes flying out to Salt Lake City after an investor said it wouldn’t transact with Delshah within the deadline unless Delshah agreed to co-sponsor a different deal with it. In another case, Shah consulted a seller who was going through a difficult time with creditors. 

Among Delshah’s largest transactions was the 24-floor office portion of CitySpire, a 70-story tower at 156 W. 56th St. Delshah and AM Properties bought a combined 50% stake in the $130M deal, while Realm owns the other half. 

Delshah rebuilt its multifamily portfolio, starting with the $76M acquisition of 34 Berry St. in April. It scooped up three more Williamsburg buildings for $128M in July.

That same month, the firm purchased a retail condo on the Upper West Side for $12.9M.

Delshah then acquired a five-building apartment portfolio, also on the Upper West Side. The firm bought $37M in notes, secured by the properties, from Signature Bank in 2022. The previous ownership “ultimately decided to just throw in the towel,” making the portfolio the final asset of the 1031 exchange, according to Shah.

The spree was backed by loans from Prospect Ridge, Ares and Peapack Private Bank, but Shah said the firm will also be leaning on its experience of assembling creative capital stacks moving forward.

Shah plans to offer two tokenized offerings on RedSwan, a platform that allows cryptocurrency to be invested in real estate. The offerings are expected to launch this fall. 

Returning to the Israeli bond market isn’t out of the question either.

“We were one of the few companies that paid all of our bonds back despite friction in the market,” Shah said. “Various people there have reached out and said we're welcome back in that market.”

The 1031 exchange clock may be up, but Shah isn’t done yet — though he doesn’t expect to sustain the same pace of closing seven deals in four months. 

He is exploring the L train corridor through Williamsburg and Bushwick and into Ridgewood. On the other side of Queens, he is interested in Long Island City, Astoria and Woodside.

“We should be good for four to six quality, high-eight-figure, nine-figure deals a year,” Shah said before briefly pausing. 

“I really enjoy what I do, and so I might say that, but if three good deals come in one quarter, we'll figure out how to do it,” he added. 

EDITOR’S NOTE — In the U.S., the national suicide and crisis lifeline is available by calling or texting 988. There is also an online chat at 988lifeline.org.