This CEO was out to dinner when he caught his AI agent wasting $1,000 in tokens. He says ‘insecurity’ is a bigger problem

Branden Jenkins was out to dinner when he pulled out his phone, glanced at his AI usage dashboard, and realized his weekend coding session had just cost him $1,000 — charged automatically, in $1,000 increments, to a card set on auto-renew.

Jenkins is the CEO of Maxio, a private-equity-backed software company headquartered in Atlanta that’s on a path toward $100 million in annual revenue over the next couple of years.

He’s also, by his own admission, near the top of his company’s internal AI spending leaderboard — an odd place for the chief executive to land.

“A thousand is not that much, I would say, but for one weekend, it’s pretty annoying,” he said in an interview with Fortune .

Describing his agent as “cooking away,” he described his response as “Wow, I just got here quickly.” The episode has become something of a parable inside his company — and inside corporate America more broadly — for how quickly “agentic” AI tools can consume money without anyone quite noticing until the bill lands.

But Jenkins said the surprise invoice isn’t what’s keeping him up at night.

The deeper problem is something messier and more human: his own employees’ “insecurity” about being outpaced by the technology — and by him.

How a weekend turned into a $1,000 lesson Jenkins, a self-described technical CEO who builds his own agents and automations, said he can write code from his phone using Claude even while away from his desk — which is how he ended up debugging and iterating on a project at dinner.

The token wallet he’d set up to fund those sessions was configured to auto-refill by $1,000 every time it ran dry, silently recharging his card without requiring a second thought — until he saw the total.

“I don’t have governors where a lot of my staff hits limits, and they have to ask for approval,” Jenkins said, describing his own unlimited internal budget as both a perk and a liability.

“So I started leaning in and going, ‘What does this look like?'” What he found, he said, is that a lot of the waste comes down to model selection and runaway conversational drift — an AI system wandering a user down paths they never intended to go.

“A lot of times it’s the agent’s own mistakes that’s burning your money,” Jenkins said.

“You kind of find yourself just chatting, and [things] getting away from you.” Casting his mind back to his dialogues with his bots, he said, “You’re like, ‘Yeah, yeah, I like it, more of that, more of that.’ All of a sudden you end up in who-knows-where, and you’re like, ‘No, I don’t want that at all.’ So some of that money is just wasted because it took you there.” His experience mirrors a pattern now well documented across the industry.