‘I Want My Employees Building My Business, Not Theirs’ episode artwork

EPISODE · Jul 28, 2026 · 50 MIN

‘I Want My Employees Building My Business, Not Theirs’

from 21 Hats Podcast · host 21 Hats

Side hustles have gone mainstream. More employees than ever are starting businesses of their own—sometimes to earn extra income, sometimes as insurance against layoffs, and sometimes because they dream of becoming entrepreneurs themselves. But what does that mean for the businesses they already work for? If you invest months in training an employee, isn’t it fair to expect that person to devote their best energy to helping your company grow? That's not an immediate concern for Lena McGuire, who's still a solopreneur. But as she prepares to hire and train her first employees, she worries about investing in people who ultimately may see her business as a stepping stone. Sarah Segal isn’t as concerned, but she does want her employees to view their jobs as careers, not placeholders. And then there's Channon Kennedy. While working full time at Silicon Valley Bank, Channon invented a woodworking tool, got it manufactured, landed national distribution, and traveled the country to trade shows—all, she says, without letting her day job suffer. And that’s what she expects from her employees with side hustles.Meanwhile, both Lena and Sarah are wrestling with another challenge: finding the right home for their growing businesses. Lena needs a showroom but doesn't want to sink money into leased space—and she can't find a building to buy. "I'm missing out on growth," she says. "I feel like I'm stalled." Sarah has opened a second office in Silicon Valley, but she's wondering whether it's time to leave her quirky “starter” office in San Francisco for something that better reflects where her business is headed. Buying would be ideal, but that's easier said than done in San Francisco these days.Plus: Sarah recently did something she hadn't done in almost a decade as a business owner—she turned on an out-of-office message and actually unplugged for a vacation. Spoiler alert: there was only one real crisis.

Episode metadata supplied by the publisher feed · Published Jul 28, 2026

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