PHOENIX — Kirby Vanderzant, 42, brown belt and founder of premium grappling subscription service Rollworthy, has been unable to cancel his own account since March 6, an internal review confirmed Tuesday, raising pointed questions both inside and outside the 11,400-subscriber company about whether anyone at the Phoenix HQ has ever actually tried to leave.
Vanderzant, who launched Rollworthy in 2022 after a 14-month pre-seed spent consulting with “three funnel architects and one guy from his gym named Dennis,” initially attempted only to downgrade his personal “Lineage” tier ($89/month) to the entry-level “Drilling” tier ($29/month). He had hoped, according to a Slack message seen by multiple employees, to “model frugality for the team” ahead of a planned press release titled “Why I Turned Down Private Equity Twice.”
That press release has since been quietly moved to Q3.
The cancellation flow Vanderzant is now trapped inside was designed two years ago by Rollworthy’s three-person retention squad with the explicit directive, per an internal brief, to “meet the subscriber where they are emotionally.” The flow routes all downgrade attempts through a chatbot named RollBot, which Vanderzant personally trained on 2,400 hours of his own instructional content, meaning every time he tries to cancel, a digital version of him very patiently walks him through why he should not.
“On his first attempt, RollBot suggested he rewatch the ‘Welcome To Rollworthy’ orientation video,” said Head of Product Maritza Colino, 38, who has stopped making eye contact with Vanderzant in the kitchen. “On his second attempt, RollBot suggested he rewatch the ‘Welcome To Rollworthy’ orientation video. I believe we are now on the sixth such recommendation. He has watched the video three times. I know this because he can be overheard watching it.”
On attempt seven, RollBot offered Vanderzant a 72-hour free trial of the exact tier he was trying to leave. Vanderzant clicked “No thank you,” which a forensic review has since determined is a button that does not actually do anything. On attempt eleven, RollBot asked him if he had tried the “Guard Retention System” instructional yet and offered a 15% discount, which Vanderzant described in a private message to his wife as “honestly, a really good deal — but that’s not the point.”
To date, Rollworthy has charged Kirby Vanderzant’s personal credit card $1,380 in an effort to stop charging his personal credit card. This figure represents six consecutive auto-renewals at the Lineage tier, plus two “loyalty discount” upsells he says he accepted accidentally after what he described as “a very persistent modal.” On March 28, his credit card was replaced by his bank due to suspected fraud. Rollworthy’s billing system, which Vanderzant has publicly described in investor decks as “smarter than the subscriber,” automatically pulled the new number directly from his authenticated account profile and resumed billing within 48 hours.
“We actually built that feature specifically to stop churn due to card expiration,” said CTO Brandt Yuen, 35, staring into the middle distance. “We called it CardRecall. I pitched it at our 2023 offsite. Kirby clapped. I remember because I was watching him clap.”
On April 12, in what coworkers describe as his lowest moment, Vanderzant paid a third-party service called QuitMySubs $49 to cancel the subscription on his behalf. QuitMySubs emailed him a triumphant success confirmation 36 hours later stating that his account had been “successfully downgraded” to Rollworthy’s premium “Black Belt Vanguard” tier, which costs $129 per month — a net increase of $40 over the plan he started on. The email closed with a five-star review request and a referral link.
Vanderzant has not yet logged a response.
Employees say the situation has become tense. Customer Success lead Paolo Ricci, 31, has been avoiding Vanderzant’s desk after receiving what he called “a very raw” 1 a.m. voice memo in which the CEO asked, unprompted, whether the cancellation flow had always been “like this, or is it getting worse.” Ricci, who answered “like this,” was subsequently assigned to a working group.
At home, sources close to the family report that Vanderzant’s wife, Jules Vanderzant, 39, a licensed midwife with no recurring subscriptions of any kind, has been “supportive but confused.” She reportedly canceled his Hulu, his ClassPass, and his Spotify Family plan in under eight minutes last Saturday while he watched, then asked him, gently, what was different about his own company.
Vanderzant is said to have answered only, “Emotion.”
The Rollworthy board of directors is scheduled to meet next Tuesday in a session titled “Reducing Subscriber Friction.” Vanderzant is the only presenter. According to the draft agenda, he will open with a slide reading, “The subscriber journey should feel effortless.” Beneath it, in smaller text, is the line, “We believe subscribers stay because they want to.”
The final slide, per the deck’s internal review, is a pull quote from Vanderzant’s own “Welcome To Rollworthy” orientation video. It reads: “You will know you’re ready to level up when you stop trying to leave.”
As of press time, RollBot had just offered Vanderzant a 20% discount on a new instructional called “Sweeping From Bottom Position.”
He had not yet responded.