Randall Leaman, Paramount Management Group's chief executive officer, texted the company's owner, Daryl Heller, on Nov. 21, 2024, with bad news: a Lancaster County judge had ordered Paramount to relinquish the company's ATMs and pay investors $138 million to cover missed monthly payments since April.

But Heller apparently shrugged off the impact. A deal was still in the works, Heller texted Leaman, and a planned $455 million total buyout of all the investors would still proceed once another legal case was settled.

“They know they can’t take over ATMs (assignments of locations agreements, etc) and will take our payment as soon as Superior is settled,” Heller texted Leaman just before 2 p.m. on Nov. 21. “We have another strategy call with them at 4 p.m. and I am on with them now.”

READ: Under oath, Paramount execs could not say ATM company wasn’t a Ponzi scheme

Leaman, who had spent the previous nine months texting Heller about Paramount’s escalating financial problems and who, two months earlier, had said the company’s demise seemed a “foregone conclusion,” took comfort in his boss’s confidence.

“So this is just a formality and the original deal is not off?” Leaman texted Heller.

“100%” Heller replied.

But that prediction didn’t come true, and the Nov. 21 court judgment would prove to be a fatal blow to the staggering company which, at the time, was just weeks away from having its offices raided by the FBI, laying off all its employees and ceasing to exist as an operating entity.

Last year’s collapse of Paramount Management Group erased more than $500 million of investors’ money and prompted a federal investigation into allegations of fraud. It also marred the reputation of Heller, who has gone from the dealmaker with the golden touch to a business pariah under the cloud of possible criminal charges.

As questions remain unanswered publicly about what ultimately led to Paramount’s downfall and where all the money went, nine months’ worth of text messages between Heller and Leaman offer a glimpse into what two key executives were saying to each other during the company’s final months.

The thousands of texts were an exhibit attached to an April 25 filing by representatives of investors in Heller’s personal bankruptcy case in New Jersey. Attorneys for the Prestige Investment Group funds, which includes some 2,700 investors in ATMs managed by Paramount, used the texts to illustrate that Heller was actively involved in Paramount’s management.

The text exchange was turned over by Leaman in response to a subpoena from the Prestige attorneys who are trying to collect on the $138 million judgment. (The text exchanges in this story have not been edited for style, punctuation or grammar. They are included as they appear in the court filing.) In the texts, which run across 664 pages, Heller says repeatedly that he’s on the cusp of cutting a deal – in days, sometimes in hours – that would set everything right.

The exchanges also show that Leaman, the company's CEO, was largely in the dark about how Heller hoped to come up with $455 million for a buyout of investors whose lawsuit, filed in late August 2024 after months of missed payments, became the company’s undoing.

“Daryl, I’m on pins and needles about the funding for this,” Leaman texted Heller on Oct. 9, after investors had approved Heller’s proposal of what would ultimately be a $455 million agreement to pay out all 2,700 investors.

“I will not bug you at all on this. But will you please do me a favor and text me when you know you’ve got it all locked up?” Leaman texted about what he had previously told Heller was “the grandaddy of all worries for me.”

READ: Who is Daryl Heller? A look at ATM network owner's life, business career

Months of shortfalls

The text message exchange begins on March 13, 2024, with Heller’s belated response to Leaman’s birthday wishes to Heller, who had turned 54 years old on Feb. 26.

“Good morning Daryl and Happy Birthday. I hope you have a great day and know that you are loved,” Leaman texted.

Over the next several weeks, the pair only exchange a couple of messages, including one on April 7 in which Leaman extends an invitation for “wine and cigars” by the fire at his house. Heller responds: “Very kind of you. I left for New York to try to close this 80m deal.”

Early signs of trouble include Leaman’s April 5 text about “the incident this morning with the investor” and an April 12 mention of a new lawsuit against Paramount. By April 16, Leaman was raising alarm bells with Heller about cash flow problems at Paramount – the topic that would come to consume their exchanges.

“Partners and employees are aware and vendors are putting us on credit hold. Would like to understand what is happening and when we will be out of the woods here. Happy to meet anywhere that works for you,” Leaman texted April 16.

In response, Heller offers what would be the most detailed explanation he would ever give Leaman via text, saying he was working to restructure, or recapitalize, Paramount’s debt. Heller described a plan that he said would reduce the company’s overall debt, or what he calls “deleverage.”

“Randall, I failed you and I apologize. The recap was supposed to be in place already. We used way too much working capital for cryptocurrency and cannabis the past couple years. … I’m just finishing off this recap so we can get this challenge behind us and move into deleverage.”

READ: ‘Out of order’ Paramount ATMs retrieved; cash machines taken back 6 months after network collapse

Heller then mentions getting pressure from Dave Zook, a manager of some Prestige funds that collected money from investors to purchase ATMs. Those ATMs were then managed by Paramount, which distributed the monthly payments to the 2,700 investors. Over more than a decade, those payments had proved a reliable source of income.

“Dave Zook is putting a lot of pressure on me and I’m just giving him high level multiple contributing reasons as to why we can’t pay this last fund. … I should have the first tranche of money coming tomorrow to close out the funds. Please don’t take any calls from Dave until this is (behind) us as I will handle,” Heller texted.

Leaman responded: “When you have this resolved, will you please give me something I can release to the entire company about this. Everyone is aware of this as vendors are threatening to shut us off and I’m concerned about the lack of trust this will create if we don’t address.”

But the problem was never resolved. The money Heller promised to “close out the funds” never arrived, and Paramount’s cash flow problems worsened.

At the end of April, Paramount failed to make monthly payments to its investors, saying at the time that it was switching to a quarterly schedule, which was also not kept. Those missed monthly payments ultimately led to the Prestige lawsuit against Paramount in late August and a $138 million judgment.

A frantic CEO

Paramount’s cash crunch and the operational and legal problems they led to became an overriding – and at points apparently debilitating – issue for Leaman, who continually peppered Heller with questions about the status of promised funding. Heller did not respond to all Leaman’s queries.

“Any word on funding coming in We are getting feedback from employees that they are wondering if they should look for work elsewhere,” Leaman texted May 13. “I’m sorry Randall,” Heller responded. “I’m working hard on it. They definitely don’t need to be looking elsewhere.”

“Any update on funding? We have a number of vendors who are getting ready to shut us down and this will mean we can’t keep our machines operational,” Leaman said in a June 6 text that Heller didn’t respond to.

On July 10, Leaman texted: “To cover payroll tomorrow AND pay customers who we have already pushed off, we need $475K. If I push customers one more day, we can get by tomorrow without additional cash and still be ok for payroll. That said, we need $400K for Friday or we are toast.” Later that day, he added “Is this the end of the line for us? I’m fearing the worst.”

In response to the July 10 texts, Heller responded: “I need to finish this funding today/tomorrow and it takes care of everything. I can get money over for payroll if we need it."

As he asked about funding, Leaman updated Heller on the growing number of vendors threatening to cut them off, including the company that kept the Paramount ATMs filled with cash. Lawsuits also mounted against Paramount.

“Seems like we keep getting surprised by these,” Leaman texted Sept. 18 about a creditor lawsuit seeking $3.8 million.

READ: Into the ‘Heller-Verse’: former ATM network owner’s many businesses, explained

As pressure built on Paramount into November, Leaman told Heller about how the stress was causing him to not be able to eat or sleep. He also lamented his own shattered reputation, raised his desire to get paid for his small ownership stake in Paramount, fretted over garnishment of his own bank accounts to pay Paramount’s debts, and declared his intention to step down as CEO, which he eventually did in early December.

“I’m having panic attacks and shaking uncontrollably at times,” Leaman texted on Nov. 23.

Yet even as the bad news piled up, Leaman expressed some continued belief in Heller.

“Just a few words to let you know that in spite of the pain that we are experiencing today, I am looking forward to what is next together. After this is behind us and you've had a chance to recover and regroup, I look forward to a postmortem evaluation and creating a new future together,” Leaman texted Nov. 10.

Less than a week later, though, Leaman once again turned pessimistic. “Given your lack of response to investor related questions I am feeling relatively certain that this is all going to collapse very soon … I’m quite afraid right now,” Leaman texted Nov. 16.

Dealing until the end

Even after the $138 million judgment on Nov. 21 and the order to turn over ATMs, Heller continued to work on a deal to buy out investors, the texts show. Leaman and Heller also strategized how to keep Paramount ATMs from being turned off by vendors and merchants who hadn’t been paid in months.

“Both comms providers are going to shut us down. This means that ALL ATMs will stop operating. We owe the one $100k and the other $69k. This will occur as early as tomorrow,” Leaman texted Dec. 4. “We can make some progress payments that might be half that amount but they are tired of us paying late.”

In early December, they also worked to transfer some information about the ATMs to the investor group which legally owned them, the texts show. Leaman, who at 6:29 am. On Dec. 3 texted Heller an official resignation letter, asked later in the day about his possible future at Heller Capital, the holding company that included Heller’s various businesses.

“Any date when the investors take over?” Leaman texted at 10:16 p.m., adding: “And did you say that I have a job at heller cap?”

“Yes. Rebranded,” Heller replied to the job question, referencing their previously discussed plan mentioned in the texts to find a new name for Heller Capital.

Late on the night of Dec. 4, Leaman texted Heller to say he had seen a teaser for a WGAL-TV segment on the $138 million judgment against Paramount and how the Paramount ATMs at Pennsylvania Turnpike service plazas that had gone down just before Thanksgiving.

“Whatever,” Heller replied, before adding: “And my name?”

“I don’t know. It was just a teaser. I assume so,” Leaman wrote, before adding: “So how does this all end? What makes this go away?”

The next morning, after asking for $50,000 for a Florida vendor, Leaman texted Heller about the appearance of FBI agents at Paramount’s Lancaster city offices at 415 N. Prince St. which also housed Heller’s other companies, including Heller Capital Group.

“FBI Raided office at Paramount. Took computers. Passwords. Etc. 20 agents. Went to heller capital as well,” Leaman texted at 10:07 a.m. on Dec. 5, receiving no reply from Heller.

That afternoon, Leaman sent two more texts that went unanswered and are the final ones in what is now Exhibit F in a brief Prestige filed April 25 in United States Bankruptcy Court for the District New Jersey, where Heller filed for personal bankruptcy Feb. 10.

“good afternoon Daryl – This is Randall Leaman,” reads the text sent at 2:49 p.m.

“Please respond if you get this,” reads the one sent at 2:50 p.m.