Every founder gets the same advice at some point in their journey: Be willing to pivot. Far fewer people talk about what that actually feels like—when to leap, when to walk away, when to trust the quiet voice telling you something is off.
We asked founders of 13 businesses that are building on Shopify how they know when it’s time to change direction. Not in theory. In the moments that actually counted.
Here’s what they said.
Catherine Goetze, founder and CEO of Physical Phones, calls her gut a “cosmic compass.” It only speaks up, she says, when she’s misaligned. When she’s on the right path, it goes silent.
“My gut has never steered me wrong. The challenge is actually following it. First, being able to hear it. Then trusting it enough to go in that direction.”
The idea for Physical Phones kept coming back to her for two years before she finally made her first video about a bluetooth landline phone.
Before founding fragrance brand LORE, Melanie Bender had a successful career building skin care brands. But she seriously considered turning down offers at both Versed and Rhode. A coach helped her see the difference between fear and excitement—and that the two often feel identical from the inside.
“Fear is the risk of pain. Excitement is the risk of potential.”
The roles that scared her most turned out to be the ones with the biggest payoff.
Jing Gao, founder of Fly By Jing, launched a line of frozen dumplings that took off. Then she killed it—because shelf-stable sauces had a better margin structure and frozen was pulling focus from the core business.
“Sometimes something works and you still need to pivot. Just because it’s shiny and bright doesn’t mean it’s the right thing for the business.”
AC Hampton of Supreme Ecom thinks about Blockbuster every time the market shifts. When iOS 14 broke Meta tracking, he rebuilt with UTM codes on Shopify and added third-party software platform Triple Whale. When AI hit, he treated it as a CEO-level responsibility, not a side project.
“Blockbuster had the chance to be the biggest company in the world. All they had to do was listen. Within three to five years they were bankrupt.”
He doesn’t allow himself or his team to coast.
Melissa Palmer left a hula-hoop company with her head down, convinced she’d failed. Someone pulled her aside and told her it was the best thing that could have happened to her. She believes it now.
“‘Fail fast’ is an expression. I like ‘fail with grace’ better. Graceful failing—that’s mine.”
She returned to Osea sharper and hungrier, and eventually became its CEO.
Kevin and Jin Chon, founders of Coop Sleep Goods, built the company while raising three kids—eventually hiring a leadership team and learning to let go of work they used to do themselves.
“It’s like we’re hanging on the back of the mane of a lion running through the jungle. Change is normal. Get used to it,” says Kevin.
Jin left a career in law to build Coop, but the stability she used to chase, she says, turned out to be something they had to build themselves.
Aishwarya Iyer built her olive oil company, Brightland, through every phase a founder hits. The hardest pivots, she says, are usually about people—and the ones she regrets are the ones she waited too long to make.
“Change is happening to us, or it’s happening for us. That’s up to us to decide.”
Slow to hire, she’s learned. Slow to fire she now knows can be costly.
Matt Hassett, founder of Loftie, spent his early career at the City of New York trying to help people recover from the 2008 mortgage crisis. Then he hired the design firm IDEO on a state-funded project—and met the kind of people who said “let’s try” instead of “we can’t.”
“That curiosity is what changes everything. It was exactly the type of people I needed in my life and I didn’t know I’d been missing.”
He’s been an inventor ever since.
Vy Nguyen took over his father’s small, locally focused manufacturing business and scaled it globally into mattress brand Avocado Green. The lesson he learned a little too late: Stop wearing every hat. Especially the ones you like.
“You have to be strong enough in your own skin to say, ‘This person is much better than me at this, so I should relinquish responsibility here.’”
He also wishes he’d built a bigger network sooner. You can’t keep fishing in a small pond.
Drew Scott of Lone Fox shut down the men’s fashion YouTube channel paying his bills to go all-in on a 100,000-subscriber interior design channel he felt more passionate about. His manager pushed back. He did it anyway.
“I just felt so much more passionate about it, and the videos were doing better—but they also took me so much more time. That’s where I really invested everything into Lone Fox.”
Eventually, he pivoted again: from selling contemporary products to one-of-one vintage. Sales more than doubled.
Sean Reyes, founder of automotive supply brand Shock Surplus, started selling video game characters as a kid, did a short stint at Blizzard Entertainment, and built his career around one thing: time freedom over money. He thinks the old advice about not following your passion is out of date.
“Don’t follow the playbook from five years ago on seeking economic opportunities. There are so many ways to provide value now that didn’t exist 10 years ago.”
Carmen Dianne and Kara Still founded Prosperity Market during the pandemic, when TV and film—their previous industries—had shut down. By the time the world opened back up, they were too deep in to consider going back.
“There was no space to go back by then. We had done so much so fast. It just felt like the thing I was going to do next,” says Kara.
Sara Sugarman of Lulu and Georgia started out working within the publishing industry, then founded Lulu and Georgia to build a digital first furniture brand. Her team has learned to see change differently than most.
“Approach change not as an obstacle, but as an opportunity. Once you do, it’s not as scary—it can really be a driver for the business.”
Every founder in this group has walked away from something shiny, leapt at something terrifying, or sat quietly with a question they couldn’t answer yet. None of them romanticize it.
The common thread: Listen to the quiet voice. Tell fear and excitement apart. Move when you know—even if you’re scared, even if it’s working.
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