AI, Compliance & Why You Can't Ghost the Government

In this episode of Ops or Die, hosts Katie Whitcraft and Maria Pienaar sit down with Sean Flynn, Chief Legal Officer & Co-Founder, and Stacy DeLong, Director of Marketing at SingleFile, to talk about the least sexy topic in startups -and why ignoring it can literally kill your company.

Compliance isn’t optional. It’s mandatory, recurring, and unforgiving. And no, AI can’t magically clean up the mess after you’ve missed filings, lost good standing, or accidentally dissolved your company on paper.

In this episode, we unpack:

• Why “small-c compliance” is quietly one of the biggest existential risks to scaling companies
• How missed filings can block financings, void contracts, or get your company name taken
• The real cost of fines, reinstatement, and lost momentum (spoiler: it’s not just money)
• Where AI actually helps—and where humans still have to step in
• Why compliance chaos usually starts as “just one more thing” on someone’s job description
• How centralized systems, tech-enabled services, and expert oversight prevent avoidable disasters

This is a candid, real-world conversation about operations, risk, and why founders can’t afford to treat compliance as an afterthought—especially in a remote, multi-state, AI-powered world.

Because operations isn’t sexy…until it saves your ass.

Visit SingleFile at www.singlefile.ai, or call 1-800-391-9869.
Stacy DeLong LinkedIn
SingleFile LinkedIn

ScaleSpark Website: www.scalespark.ai
Katie Whitcraft LinkedIn
Maria Pienaar LinkedIn