The My Pillow CEO is a former crack addict and bankrupted gambler who made – and might soon lose – millions thanks to a religious devotion to Trump. — Kate Taylor, Business Insider Retail Correspondent
The My Pillow CEO is a former crack addict and bankrupted gambler who made – and might soon lose – millions thanks to a religious devotion to Trump. — Kate Taylor, Business Insider Retail Correspondent
MyPillow guy Mike Lindell: The inside story, in Trump's final days
  • My Pillow CEO Mike Lindell is one of Trump's final defenders, pushing baseless voter fraud conspiracies.
  • Insiders say Lindell has striking similarities to Trump, as a brash CEO obsessed with his own brand.
  • Lindell says supporting Trump drove "off the charts" sales. Now, the tide might be turning.
Perhaps more than any other CEO, Lindell has driven his company straight into the minefield of modern politics, embracing the kinds of controversies and culture war topics that most businesses consider radioactive, and doubling-down in situations in which today's corporate playbooks would recommend damage control. A staple of late-night TV infomercials, Lindell — whose backstory includes a stint as a professional gambler and a struggle with drug addiction — and his pillow company have become one of the most curious business phenomenons of the Trump era.

... Lindell shares striking similarities to Trump, who he first met in what he calls a "divine appointment." He is obsessed with his personal brand, which is synonymous with his business. His brashness and perceived authenticity resonate deeply with fans. He has no interest in corporate norms.

Lindell said My Pillow has thrived in the Trump era, claiming his support of the former president fueled "off the charts" sales growth. Revenues from the company's website roughly tripled from 2015 to 2019, according to an estimate by GlobalData. And site traffic skyrocketed in 2020, as Lindell campaigned for Trump's reelection.

Now, the tide may be turning. This week, retailers including Kohl's and Bed Bath & Beyond announced they would stop selling My Pillow, citing poor sales. Affirm, a financial technology company, also cut ties. Even an online porn site, seeking to capitalize on the trend, said its actors would no longer use My Pillows for "sexy pillow fight" scenes. And Lindell personally faces legal threats from voting technology company Dominion over his repeated claims of voter fraud.

... Lindell founded My Pillow in 2004, while bankrupt and battling a destructive crack cocaine addiction, after a dream in which he was searching for "my pillow."

The CEO says in his 2019 book "What Are the Odds? From Crack to CEO" that he funded the early days of the business by counting cards as a professional gambler. According to the book, his life was such a mess that his drug dealers staged an intervention.

The Minnesota-born Lindell, 59, is twice divorced. He split from Karen, his wife of 20 years and mother of his four children, in 2007 as they both battled crack cocaine addictions. His second marriage, to a woman named Dallas, ended just 20 days after they were married in a lavish $100,000 wedding according to Lindell's book. As of the book's publication, Lindell was seriously dating a woman named Kendra, who Lindell's sister said God told her he would marry.

... Lindell eschews corporate norms in favor of his instincts and a reliance on a loyal team of insiders.

He does not have a desk or a computer, opting to do all of his work from his phone. He operates out of two conference rooms when he is in My Pillow's Chaska, Minnesota headquarters. If someone wants to talk to him, they simply show up at the conference room, even if it means interrupting another meeting. According to Lindell, 500 of his employees have his direct number, so they can call him immediately any time there is a problem with the business.

The person who worked with My Pillow until 2019 called the set up "dysfunctional." Lindell prefers "relaxed." Lindell told Insider that he runs My Pillow "like a family," providing unlimited bereavement leave, paid leave for addiction treatment, and flexible hours.

The company is also like a family in more literal ways. Many members of the executive team are long-time friends or family members, including Lindell's 30-year-old son Darren, who was promoted to chief operating officer in 2019.

Reardon said she saw "obvious nepotism" during her time working at My Pillow. According to the former retail worker, Lindell employed many relatives, who were "held to a different standard than the rest of the employees."
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