CashDrop Employees Speak Out

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This story was published in collaboration with La Voz Chicago

Two years ago, in a Harvard Business School case study, the CEO and founder of CashDrop—an app designed to offer businesses a free mobile storefront that allows customers to eat the fees, rather than the businesses—outlined a vision for the kind of company he wanted to build. The once-undocumented immigrant from Mexico wanted to create an app that would give back to the Latino community.

“I’m not just interested in the money,” Ruben Flores-Martinez said.

The CashDrop platform can be adopted by small mom and pop shops and has been marketed to Latino communities in the U.S. via Spanish-language ads on social media. 

Locally, the app has been used in events like Chi Michelada Fest 2022. Even nonprofits like Healthy Hood Chicago have announced they will exclusively use CashDrop. 

Recently, the app hosted a bilingual workshop alongside the Little Village of Commerce at which 22nd Ward Alderperson Michael Rodriguez encouraged street vendors to go cashless with the app as a way to mitigate robberies. 

“America has this real obsession with growth,” Flores-Martinez said in the Harvard case study. “{A top tech investor} said to me, ‘[Venture capital] is a drug, you have to be careful with it.’ Companies can get put into this fasttrack to keep pushing and spending more money until you lose control of where the company is going and just crash. I don’t want to do that.”

CashDrop has been good to Flores-Martinez. It landed him on the Forbes 30 Under 30 2021 Social Impact class list and most recently, in the Crain’s Chicago Business 40 Under 40 class of 2022. By mid-2020, CashDrop had raised around $2.7 million from investors such as Harlem Capital, Long Journey Ventures, and Michelle Phan. According to PitchBook, the latest round of investment this past November netted CashDrop more than $11 million. 

But in recent months, three former CashDrop employees have collectively taken to social media to denounce workplace bullying, broken agreements, and a lack of transparency from Flores-Martinez, among other issues. At least one of these and another former employee said the stress of working at CashDrop led to hair loss, anxiety disorders, and other medical issues. South Side Weekly and La Voz Chicago interviewed these and other former employees of CashDrop, and drew on emails, screenshots, and other documents to tell this story.

Ruben Trejo, a forty-year-old from Chicago, joined CashDrop as an affiliate in July 2021 and eventually became event manager for the company. He joined because, “Me being Latino and all the employees being Latino was something that I wanted to be a part of,” he said in a testimonial he shared on Instagram. 

Trejo was sold on the dream of becoming a millionaire, which was something he said Flores-Martinez would constantly tell his employees that he wanted to see them become. In May, Trejo would bring in one of the company’s biggest promotional events, a car show held in Georgia featuring hundreds of cars and bikes with general admission tickets starting at $250.

“That’s where things took a turn,” Trejo stated in the video, which he posted on December 30, 2022.

Trejo said he had made a verbal agreement with Flores-Martinez in which Trejo would keep one hundred percent of commissions from the event. But the verbal agreement was apparently not honored—instead, Trejo said he received around fifty percent of commissions from the event.

Trejo said there was never any paper trail for these decisions, which according to former CashDrop employees, was not out of the norm at the company. 

Trejo said he also did not receive reimbursements for some work trips and activation expenses he had paid for out of pocket. Multiple employees said company credit cards were often declined, forcing them to cover costs on multiple occasions, especially during out-of-state trips. 

In November 2022, Trejo was laid off and told that the company could not afford to keep him. CashDrop’s proposed severance package included only a healthcare stipend for twelve weeks, far less than what Trejo felt was owed to him. To receive the severance package, Trejo had to sign the agreement that included a nondisparagement clause that would have prevented him from criticizing CashDrop publicly. He declined the offer by email:

It’s a really disrespectful offer considering the verbal agreement that Ruben had with me regarding 100% commissions….I won’t be signing anything and I will exercise my right to speak freely about my experiences at CashDrop on social media and to the public.

Trejo recalls feeling betrayed. In his Instagram video, he said, “To have one of your own brothers, tu hermano, disrespect you and punch down on you daily, it has to stop.”

Trejo wanted to bring attention to his experiences and reached out to other former employees, wondering if what he had gone through was shared. 

He soon found former colleagues who said that Flores-Martinez had verbally harassed them. “They all kept telling me the same thing,” said Trejo. “They kind of sparked something inside of me to put a stop to this.”

He encouraged them to come forward and build public outcry on social media platforms. Ashley De La Torre and Jaqueline Rodriguez, who had been at CashDrop under a year and had since left the start-up, agreed to record testimonials. 

They came forward recounting instances of verbal abuse, aggressive episodes, and a toxic work environment that they said led them to walk out indefinitely. Their videos were liked by hundreds of people and received dozens of supportive comments. 

“He would be very stressed out when it was close to paying the bills,” said Rodriguez, who remembered Flores-Martinez lashing out as regularly as once a week but especially in the final and first weeks of the month. 

Flores-Martinez’s behavior described in the testimonials and interviews took the form of ridiculing interns, public shaming, slamming his hands on tables, and in one instance patting an employee on the head. 

“It’s unfortunate how much violation became normal—how being violated by a CEO, how the emotional abuse just kind of became a part of the day,” said De La Torre in the Instagram video. 

In an interview with South Side Weekly and La Voz Chicago, Flores-Martinez denied the allegations.

At first, Flores-Martinez said the allegations were due to “a combination of misunderstanding, high pressure environment, there’s definitely a lot of emotions involved,” but later called them “completely baseless” and that he was considering legal action.  

“There is no fraud. There is no big story. There is no sexual misconduct, there is no MeToo thing, there’s nothing there,” said Flores-Martinez. “People are just waiting, thirsty for blood to cancel somebody.”

“Am I an explosive character? It depends on how you slice the apple,” he said, adding, “what company doesn’t have high stakes, high energy meetings, where there are disagreements.” But he denied ever threatening employees or making them feel oppressed or controlled.

Lisa Kowalczyk was part of the company’s customer success team and had joined CashDrop in January 2021. In an interview, Kowalczyk said that on December 28, 2022, she and other CashDrop employees received a company-wide Slack message alerting them that ex-employees were criticizing the company on social media and demanding that current employees sign an NDA within two hours—or be fired. 

Kowalczyk told Flores-Martinez that she had forwarded the document to her lawyer to review. 

Before she could get a response from her lawyer, Kowalczyk said she was terminated two days later, the same day that Trejo, De La Torre and Rodriguez shared their testimonials on Instagram.

Kowalczyk said she suffered a work-related injury while on a work trip and that she never got the medical insurance to cover it that she was promised. She said around $10,000 in reimbursements are still owed to her from instances when company cards didn’t work, and that paychecks didn’t come on time on three separate occasions, the most recent being just before this past Christmas. 

She also recalled not getting support when one of her coworkers was terminated. “At one point, over a couple months’ span, {I was} working eighty hours a week, all day and night, because there was nobody else even qualified that could help me,” Kowalczyk said. 

She said the stress from the job eventually led to hair loss and other medical problems. 

“There was a lot of blurred lines in the boundaries of work-life balance—where work ends and begins,” said De La Torre, adding that it was not out of character for the CEO and employees to drink on the job, go to dinner after work, and constantly be told that they were a family. 

Rodriguez echoed this sentiment, stating that she and her colleagues “trauma bonded” and felt as if Flores-Martinez had isolated them from their lives. “I felt like they were my friends.”

According to a 2021 survey from the Workplace Bullying Institute (WBI), thirty percent of adult Americans are bullied at work, a number that at the time of the survey amounted to almost 49 million workers across the country. 

The numbers for women working in tech are even more staggering. A 2020 study from Women Who Tech found that close to fifty percent of women working in tech experienced harassment, with forty-two percent reporting that harassment was perpetrated by a supervisor. 

“It is normalized, it’s routine, it’s frequent, and therefore we treat it as not worthy of attention. But it is America’s silent epidemic, and we need to start paying attention because it’s harming millions of workers,” said WBI director and social psychologist Dr. Gary Namie. 

WBI is currently lobbying to pass the Healthy Workplace Bill in Massachusetts and New York

“to prevent and correct abusive work environments.” The bill was introduced in Illinois in February of 2021 but has not passed the Illinois House of Representatives. 

When concerns were brought up to Benjamin Vear, the company’s president and the person who handled HR-like responsibilities according to employees, employees said Vear reduced Flores-Martinez’s outbursts to the CEO being stressed due to lack of investors. 

Vear declined to comment or be quoted on the record.

Team dinners at the expense of the CEO at notable Chicago restaurants like RPM Steakhouse, Beatnik on the River, and Fulton Market Kitchen would later be leveraged in public shamings during company meetings, according to De La Torre. 

Employees felt stuck because some uprooted their lives and moved to Chicago for the job, while others lacked confidence to find a better workplace. 

“Ruben was very intentional with who he picked to be around,” said Rodriguez, adding that his employees were mainly young Latinos belonging to marginalized communities, whose members are often first-generation, recent graduates, low-income, and with mixed-status backgrounds. 

In response to an email that listed the allegations included in this story, Flores-Martinez wrote about the company needing to let go some employees last year for economic reasons, but that, “We can’t and will not comment on specific statements made by current or former employees.” In the end, he claimed the questions contained “inaccurate” and “verifiable outright falsehoods” but declined to clarify what specifically he objected to. “We wish you the best of luck in sorting fact from fiction,” the email ended.

In an earlier interview, Flores-Martinez said he wanted to give “opportunities to people that look like [him], in a world where none of them would get opportunities,” adding that “perhaps they think I’m an asshole, and not everybody’s gonna like me, not everybody’s gonna agree [with] the way that I move, or the way that I run my business.” 

Multiple employees said their health declined because of working at CashDrop. 

“My mental health deteriorated quickly,” said Rodriguez. “I would be extremely anxious because I had not finished a deadline or was nervous about the next day, nervous that I was going to get yelled at.”

Former employees said deadlines and expectations were often changed last minute and with little notice by Flores-Martinez, putting them in compromising situations. Kowalczyk recounted a time in which she asked for clarification and Flores-Martinez said,  “that’s not my fucking job, you need to do your job.” 

Namie said stress and hair loss are real responses to abusive conduct. A laundry list of health concerns can stem from verbal abuse including stress-related physical diseases, harmful impacts to brain function, joint pain, debilitating anxiety, clinical depression, and PTSD, to name a few. 

“These people who’ve come forward, no wonder they’re fearful. They’re reporting war wounds,” said Namie upon learning of the allegations. “Why should you suffer emotional injuries in exchange for a paycheck?” 

After going public with their experience at CashDrop, the three employees who shared their stories received words of encouragement, and some vendors like Shop Ankata stopped using CashDrop altogether. But they also faced pushback from Flores-Martinez and others at CashDrop, in texts and social media posts that attacked the former employees’ characters. Flores-Martinez took to his personal Instagram to post a series of stories including one where he wrote, “People can say whatever they feel like for their 5 likes and 10 minutes of mini clout.”

Flores-Martinez’s sister, Betsabe Brewer Flores, who worked as a supervisor within the company and had a closer working relationship with Rodriguez, left voicemails and text messages invalidating Rodriguez’s testimonial. In one text she wrote, “you did your thing and rode that wave for a free laptop, some easy work.” In a message to Trejo, Flores wrote, “You’re a slime and don’t do no work,” and “Your child doesn’t deserve his dad to tarnish his image on Ig for likes. He doesn’t know he will probably be a slime like you too.”

Brewer Flores declined to comment for the story.

For Kowalczyk, Trejo, De La Torre, and Rodriguez, their intent in speaking out is to hold Flores-Martinez accountable. 

“I just hope that he hears our stories, that he sees the harm he’s caused, and has a shred of empathy, and realizes that he’s really taking advantage of those around him,” said De La Torre. 

Yet Flores-Martinez’s continued denial of any wrongdoing and apparent refusal to engage with the criticisms makes them feel like things won’t change—and if they don’t, they believe CashDrop should cease to exist.

“Abuse is at the fundamental core of it all and Ruben has made it a point to be intertwined with the company so it doesn’t change what I think should happen to CashDrop, which hopefully is to be dissolved,” said Rodriguez. 

“Even when evidence is tacked against him his ego won’t let him be the better person,” said Trejo. “He and CashDrop are synonymous. With him at the helm of the company, [it’s] destined to fail.”

CashDrop is used by vendors based in cities around the country, like Los Angeles, Tampa, Salt Lake City, Des Moines, and Milwaukee. Vendors using CashDrop are later reimbursed processing fees. 

Kowalczyk said some vendors were still owed those fees when she left CashDrop, including a business belonging to a friend she brought on. 

She said the apparent financial troubles at the company—delayed paychecks, declined company cards, and layoffs—didn’t add up to what she described as Flores-Martinez’s lavish lifestyle. 

“There are $15,000 spent on tequila for parties, maybe another $20,000 spent at a club in Miami,” said Kowalczyk. “There’s no reason for a CEO of a new startup, that’s not profitable, to be staying at the Beverly Hills Hilton.”

The former employees have concerns for the vendors still trusting CashDrop with a portion of their business. Customer fees were most recently advertised at five percent with a minimum charge of forty-five cents. However, as of press time, when making a $5 purchase using the app, the processing fee is $1, which is twenty percent. 

According to Kowalczyk, this is because the fees were changed—a move that has not been reflected in CashDrop’s public-facing platforms. 

“As of the beginning of 2023, CashDrop actually raised the rate that they charge the customers their convenience fee,” said Kowalczyk. 

When asked about the fee change, Flores-Martinez said the fee is “dynamic” and in some instances “the pricing can be as high at fifteen percent.” He assured the Weekly that CashDrop is completely transparent with its merchants and “if there was cracks in the systems, they would have already come to light.”

What’s more concerning to the group of former employees who have spoken out is the newly launched Latino Renaissance Fund, which went live at the end of last year. Flores-Martinez pledged $1 million of his own CashDrop equity to be distributed to 1,000 Latino-owned businesses who use the app. 

Something similar was promised to employees at CashDrop, who never received paperwork for the equity they were told they would receive in the company, said Trejo in his testimonial.

“If you’re going to be working under the pretense of being Latino Renaissance, you got to treat Latinos right,” said Trejo, adding, “We’re not gonna take it especially from somebody that’s not even from Chicago.”

Though Flores-Martinez moved to Chicago from Milwaukee, he views himself as “a prominent member of the Latino community in Chicago.” 

“I am known, people know me. And I’m talking to all walks of life, [from] the fucking intern all the way to the mayor,” he said.

When asked if he was still “not just interested in the money,” he replied, “It is all about the money. It is about creating wealth for Latinos, it is about creating millionaires and billionaires that look like you and I.”

It would be those same words that once drew in employees like De La Torre. 

“He might have the gift of gab and say all the right things, but he treats the people closest to him awfully,” she said.

Jocelyn Martinez-Rosales is a Mexican-American from Belmont Cragin, Chicago. As an independent journalist she’s passionate about covering communities of color with a social justice lens. She’s also a section editor at the Weekly.