Wil Reynolds on how running a growing business makes you vulnerable

Wil Reynolds didn’t hire anyone to handle his company’s finances until it was making $5.2 million in revenue.

Before that, the CEO of Northern Liberties digital marketing shop SEER Interactive was dealing with mishaps — like forgetting it was a holiday, having to stay late in the office handwriting paychecks for his employees and forgetting to take out their taxes.

It wasn’t pretty, he said.

Once he finally hired a CFO, SEER Interactive grew its cash flow seven times, he said.

It was just one of the growing pains Reynolds talked about late last month in his talk at the Junto, a civic-minded business conference organized by P’unk Ave’s Geoff DiMasi. There comes a point in running a growing business, Reynolds said, when you realize you can’t do everything on your own — and that’s scary because it means you need other people to succeed. It makes you vulnerable, he said.

“I can’t strap everything on my back anymore,” Reynolds said. “I can’t just stay up all night and drink coffee and get it done.”

He didn’t hire an HR person until the company was at 52 employees. At 63 employees, he was still “wiring laptops” and installing Office 365.

All this from a guy who disavowed job titles for over a decade. A guy who vowed to keep his staff under 10 employees (he said he turned down business to keep the employee count that low) because he wanted to stay small and be able to get to know his colleagues really well.

Eventually, Reynolds scrapped that plan. He now runs a business of nearly 100 employees, with offices in Northern Liberties and San Diego.