Founder Raises Series A to Solve Problem Created Entirely by His Seed Round

By Crash Windward

AUSTIN, TX — Local startup founder Greg Tannen announced Tuesday that he had successfully closed a $14 million Series A round to solve a critical industry problem that sources confirmed was created in its entirety by the way he spent his $3 million seed round.

“The opportunity here is massive,” said Tannen, whose original company built an AI tool to automate hiring, which led to a wave of bad hires, which Tannen is now raising money to fix with a second AI tool that automates firing. “Honestly, the total addressable market has never looked better. We made sure of that.”

According to the pitch deck, Tannen’s new venture, Offboard.ai, directly addresses “unprecedented organizational dysfunction,” a phenomenon investors described as “surging” and which can be traced, line by line, to Tannen’s previous product.

“It’s a flywheel,” explained Tannen, drawing a circle on a whiteboard that started at ‘we caused this’ and ended at ‘we charge for this.’ “Problem, solution, new problem, new round. The unit economics basically write themselves, mostly because we keep writing the problems.”

One Series A investor praised the founder’s “deep domain expertise,” noting that no one understood the problem better than the man who manufactured it. “Greg has genuine, first-hand knowledge of exactly what went wrong,” the investor said. “Because he did it. On purpose-ish.”

Tannen confirmed that the long-term vision involves a third product to address the issues created by the second, a roadmap he described as “durable” and “recession-proof.”

“People always ask me, ‘what’s your moat?’” Tannen said. “My moat is that I am personally the source of the problem. You can’t out-compete that. Believe me, they’ve tried.”

At press time, Tannen had begun quietly noticing some issues with Offboard.ai that he believes could represent “a really compelling Series B.”