Carl Grimstad: iPayment Lawsuit, Waitr Turnaround, and ASAP Rebrand

Carl Grimstad is an American businessman best known as the co-founder of the payment processor iPayment, Inc. and later the CEO of Waitr Holdings, the Louisiana-based food delivery company that rebranded as ASAP before filing for Chapter 7 bankruptcy in 2024. His career has combined rapid company-building with two high-profile legal disputes: a boardroom fight with hedge fund creditors at iPayment, and a lurid countersuit from the same company alleging he had used it as a personal piggybank.

He holds an economics degree from Boston University.¹ In 1995 he founded GS Capital, LLC, a family private investment company where he serves as managing partner, and later formed a second family investment entity, C. Grimstad Associates, LLC, in 2006.²

Co-Founding iPayment

In 1999, Grimstad co-founded iPayment, a credit and debit card payment processor serving small and medium-sized merchants in the United States and Canada.³ He served as president from 1999 to 2011, during which iPayment completed an initial public offering in 2003 and was taken private again in 2006.¹ In 2011 he was elevated to chairman and CEO. He held that role until his ouster in August 2016.⁴

The Boardroom Fight With Chatham Asset Management

About a week after being fired, Grimstad sued in New York state court and in Delaware Chancery Court. His target was Chatham Asset Management, a New Jersey hedge fund that held a significant portion of iPayment’s debt and equity. Grimstad accused Chatham of orchestrating a “boardroom coup” to seize control of the company.⁵

According to the Delaware complaint, Chatham and allied hedge funds together owned more than 50% of iPayment’s second-lien debt and 41% of its outstanding stock. Grimstad alleged they used board appointment rights to install conflicted directors, derailed efforts to refinance the company’s maturing credit facility, and fired the company’s financial advisor (J.P. Morgan) and outside counsel (Latham & Watkins) after those advisors warned the plan breached fiduciary duties. The goal, he claimed, was to depress iPayment’s share value, convert debt to equity at an artificially low price, and wipe out existing shareholders. He said he was terminated because of his opposition to the plan.⁶

iPayment’s Counter-Lawsuit

iPayment fired back. On February 22, 2017, the company and its holding entity filed suit against Grimstad and his wife, Jessica “Gigi” Grimstad, in Manhattan Supreme Court. The complaint accused Grimstad of treating the company as his personal “piggybank” during his tenure as CEO, alleging more than $445,000 in improper personal charges.⁴

The itemized allegations were specific: $288,000 billed to iPayment for hotel stays at the Mark Hotel during a relocation from Nashville to New York, more than $70,000 in shopping charges at Bergdorf Goodman and other stores attributed to his wife, $60,000 in payments to his wife’s interior design firm, more than $10,000 for a bodyguard’s clothing, and thousands more for golf expenses and medical bills.⁴ The suit also alleged Grimstad played over 400 rounds of golf between April 2013 and November 2016 while serving as CEO.⁷

The most tabloid-ready claim: the complaint alleged Grimstad met a 26-year-old escort at the Spearmint Rhino strip club in Las Vegas, offered her $4,000 for sexual activities, and then hired her at iPayment “despite lacking any apparent qualifications.” Her mother was also hired into customer service. Both were eventually terminated, with the escort receiving a $37,000 severance package in 2012.⁷ iPayment asserted claims for breach of contract, breach of the implied covenant of good faith and fair dealing, and unjust enrichment against both Carl and Jessica Grimstad.⁴

Grimstad denied all of it. His attorney, Marc Kasowitz, said the allegations had previously been investigated internally after being raised by a terminated employee and “found to be false,” and that Grimstad had not been terminated for cause.⁷

The Settlement

By August 2017, the parties settled on terms that were, by any measure, favorable to Grimstad. He received $3 million in cash and $4 million in preferred stock, and was retained by iPayment as a special adviser at $220,000 per month for 18 months. The total package was valued at roughly $11 million, though one account placed it closer to $20 million.⁸⁹

iPayment issued a statement acknowledging that “the Grimstads believe that the allegations in the lawsuit were false” and said the company “regrets any distress that may have been caused to the Grimstads by the public filing of the litigation.”⁸ iPayment was subsequently acquired by Paysafe in June 2018.¹⁰

Leading Waitr Holdings

Grimstad returned to a public-company chief executive role in January 2020, appointed CEO and board member of Waitr Holdings effective January 3, 2020.¹¹ He replaced Adam Price, who had resigned after about four months amid corporate turmoil. Waitr had reported a net loss of $220 million in the most recent quarter and was facing restaurant-partner backlash over a shift to sliding-scale commissions of up to 25%.¹²

The Turnaround

Grimstad inherited a company that had posted a $291 million net loss in 2019 and was trading below $1 per share. His most consequential move was reclassifying Waitr’s delivery drivers from W-2 employees to independent contractors, which meant laying off roughly 2,300 workers but converting fixed labor costs into variable ones. The contractor network grew to over 19,000 by mid-2020.¹³

He also cut promotional spending, reducing the share of orders with coupons from about 50% to around 10%, expanded into grocery and alcohol delivery, and pushed delivery radii to as far as 12 miles. Waitr reported year-to-date EBITDA exceeding $20 million by June 30, 2020, with second-quarter net income surpassing $10 million, and cash on hand reached $87.3 million by the end of July 2020.¹³

Grimstad’s compensation reflected the reset. His amended employment agreement, dated April 2021, provided a base salary of $83,333 per month (roughly $1 million annually), a $3 million bonus payable before January 31, 2022, and 3.5 million restricted stock units vesting over three years.¹⁴

Rebrand to ASAP

In August 2022, Waitr rebranded as ASAP, reflecting a pivot toward a broader “deliver anything” model spanning alcohol, sporting goods, luxury apparel, and auto parts alongside restaurant food.¹⁵ The company developed proprietary in-stadium mobile ordering technology and secured a five-year exclusive partnership with MetLife Stadium, the New York Giants, and the New York Jets in July 2022, plus agreements with the New Orleans Saints, the University of Alabama, and Louisiana State University.¹⁶ It also signed national delivery agreements with Chipotle Mexican Grill and Unilever ice cream brands.¹¹

Bankruptcy

The turnaround did not hold. By January 2022 Waitr’s stock had fallen below $1 per share for 30 consecutive trading days, triggering a non-compliance notice from Nasdaq, and the company received a delisting notice on January 24, 2023. The stock moved to the OTCQB Venture Market under the ticker “ASAP.”¹⁷

Delivery operations were halted on February 13, 2024, and online ordering ended on March 29, 2024.¹⁸ On April 2, 2024, Waitr Holdings filed for Chapter 7 bankruptcy, a straight liquidation with no plan for reorganization. The filing covered all subsidiaries, including Waitr, ASAP, Bite Squad, Dude Delivery, Delivery Logistics, and Catering on Demand.¹⁹ The company reported more than $80 million in total liabilities, and all C-suite executives, including Grimstad and CFO Armen Yeghyazarians, were terminated effective immediately upon the filing.²⁰

1
The Advocate. Waitr CEO Adam Price Resigns and New Executive Named to Top Role
2
U.S. Securities and Exchange Commission. Waitr Holdings Announces Appointment of Carl Grimstad as Chief Executive Officer
3
Food On Demand. Carl Grimstad
4
Courthouse News Service. iPayment Holdings v. Grimstad, Complaint
5
New York Post. Ousted iPayment Founder Accuses Hedge Fund of Boardroom Coup
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PR Newswire. Lawsuit Alleges Hedge Funds and Their Hand-Picked Board Members Pursued Illegal Scheme to Steal iPayment
7
New York Post. Fired CEO Accused of Theft
8
New York Post. Ex-CEO Awarded $11M After Suing Over Theft Allegations
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Fortune. Chatham Asset Management, Michael Cohen, iPayment Holdings Lawsuit
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PE Hub. PE-Backed Paysafe Acquires iPayment
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BusinessWire. Waitr Holdings Announces Appointment of Carl Grimstad as Chief Executive Officer
12
Restaurant Dive. Waitr Names New CEO
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Restaurant Dive. How Waitr’s CEO Made the Company Profitable in 6 Months
14
U.S. Securities and Exchange Commission. Waitr Holdings Inc. Amended and Restated Employment Agreement
15
Biz New Orleans. Waitr Rebrands ASAP to Align With New Company Strategy
16
BusinessWire. Waitr Holdings Inc. Scores Exclusive Mobile Ordering Deal With MetLife Stadium, New York Giants, New York Jets
17
U.S. Securities and Exchange Commission. Waitr Holdings Inc. Form 8-K
18
Restaurant Dive. ASAP Files Chapter 7 Bankruptcy, Ceases Business
19
Nation’s Restaurant News. ASAP, Delivery Service Previously Known as Waitr, Files for Bankruptcy
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Restaurant Business. ASAP Delivery Service Files Chapter 7 Bankruptcy