This Boss Has 3 Rules for Encouraging Employees’ Side Hustles

  • A total of 34% of American adults have a side hustle, according to a survey published in January.
  • Staff at WorkReduce, a staffing platform, have grown side hustles with the company’s blessing.
  • The founder Brian Dolan said this encouragement helped the company find productive “doers.”

A survey of 2,000 American adults by Zapier in January found that 34% had a side hustle, and nearly a third of those side hustles had been started in 2020. A further 24% were planning on starting one in 2021.

FlexJobs’ 10th Annual Survey, conducted in July and August, found 10% of American workers were trying to take their side hustles full-time.

Brian Dolan, CEO and founder of Boston-based WorkReduce, a platform that provides flexible staff for media and

marketing companies
, has found an unintentional side-hustle culture has flourished at his company throughout the pandemic.

This has been fueled by the remote and flexible working the company has practiced since its launch in 2015.

His employees’ profitable side hustles include a whiskey-focused YouTube channel, a bike shop, a doggy daycare and lifestyle blog, a boat charter company, and a gaming podcast. Only the YouTube channel was started before the pandemic.

Some employees work up to an additional 20 hours a week on their own ventures alongside their jobs at WorkReduce, he said. Team members are encouraged to share their projects via the company’s

channels and during internal spotlight and happy-hour sessions.

Dolan told Insider he understood encouraging side hustles could mean losing staff if their side hustles took off. He said the reward of staff satisfaction is worth it.

Only one person has resigned to go full-time on the side hustle, and not many ask for fewer hours to pursue them. Dolan said he believed his staff performed better because they can pursue their passions. 

Dolan said he had three principles he follows to make it work.

Always consider a staff member’s flexibility needs when assigning them tasks

Dolan said he wouldn’t necessarily ask candidates in interviews whether they are running or wanting to run a side business.

But he said the differing time commitments allowed the kind of flexible working that makes it possible for them to do so, and he tends to match those with side hustles to clients with smaller workloads.

​​Dolan said it was “a matching process in terms of people’s general appetites and availability.”

“As we’re bringing people on, we try to understand how we match them to the type of work that’s available,” Dolan told Insider.

“If you’ve got somebody who’s up-and-coming and wants to prove themselves by working on the biggest brands in the world, we say, ‘Here you go — this one’s going to be a lot of work, and you’ll need to be at the computer all the time.'”

Recruit productive ‘doers’

People who start side hustles are the type of “doers” that WorkReduce is biased toward hiring, Dolan said.

“We’re hiring for smarts. We’re assessing people’s ability to do quantitative work — high achievers who have a good track record demonstrating aptitude and marketing that really stands out,” Dolan said.

“If you’re smart enough to do this kind of work, you’re also smart enough to balance a side hustle. It comes from that, rather than our people being overly creative. Successful remote work is about getting it done.” 

Draw the line if staff don’t deliver

Favoring results-oriented people has resulted in few issues of staff being too distracted to perform in their WorkReduce roles, Dolan said.

He recalled one woman who “wanted to be able to travel while she worked. She stopped showing up for client meetings. And it turned out she was trying to be an Instagram influencer. She was terminated.

“It was straightforward. Either you show up for work, or you don’t. If you don’t, you’re gone. But we’ve got such a robust screening process that we tend not to run into these cases.”

Alicia Amador joined WorkReduce as associate director of advertising operations in February. In April, she launched her doggy-daycare business, which she spends 20 hours a week running along with a holistic aromatherapy business.

This is on top of her 40-hour flexible week for WorkReduce. Working from home means she can run the daycare. She told Insider she brought in the equivalent of half of her full-time salary through her side hustles. 

“Flexible working means planning out how I manage my time isn’t a challenge. It’s simple to dedicate time each day to your passions,” she said.

She added that the company’s setup “creates a strong entrepreneurial mindset because we’re provided the space to do so.”

Amador would like to grow her side hustles but is happy with her position at WorkReduce too. 

Dolan said he recognized that “you can’t keep people forever.”

But he said companies can “provide the best possible working experience” with the mindset that “you don’t own your people, you attract them.”