As a bootstrapped solo founder, I’ve built my three-year-old consumer products brand with a small, steady team of contractors. So far, the model has worked for me at Hugimals World, which makes weighted plush gifts designed to ease stress and anxiety in adults and kids. We’re flexible, lean, and scrappy. But as the brand grows, I know full-time hires are on the horizon.
That comes with questions every new founder eventually faces: When is the right time? Whom do you hire first? How do you know if the new person will make your life easier—not harder?
I spoke with founders who’ve been there, to learn what they wish they’d known before making their first big hires, and how a right (or wrong) hire can shape your business for years to come.
Resist the urge to move too quickly
In 2022, Tiffany Coyle, co-founder of Twinning Pros, a Destin, Florida-based marketing agency, was managing PR and operations for her biggest client while trying to grow her now mid-six-figure business. “I knew I couldn’t scale without help,” she says.
She posted a listing for a support role and got more than 25 applicants within a week. “The first candidate I saw had everything on paper,” Coyle recalls, including experience on a campaign for a big brand. “She lit up when talking about long-term growth,” she says. “I got so excited. Excited enough to cancel all the other interviews. That was mistake number one.”
Initially, it seemed like the right help had arrived. But within the first 90 days, deliverables began slipping. “I paid her well, hoping the compensation would inspire her to rise to the occasion. Instead, I spent six months doing her job, my job, and managing her,” Coyle says. According to Coyle, it caused Twinning Pros to lose its largest client, and to take a revenue hit.
“When you’re desperate for relief, that’s when you need to slow down,” Coyle says. If she could do it over, she would have interviewed at least 10 candidates. “I would’ve run a paid trial project to see the actual work product,” she says. “I would have checked references. And most critically, I would have hired for the level of leadership I actually needed, not the support role I thought I could afford. If you need someone to lead, hire a leader. It costs more up front, but significantly less than the alternative.”
