Every founder knows mistakes are part of building a business. Fewer talk about what those mistakes actually look like in the moment: the product defect that turns into a public mess, the order you have to eat the cost of, the marketing spend that does nothing, the hire you keep too long because you want it to work.
Those moments are rarely tidy. They can be expensive, public, and deeply uncomfortable. But they can also become some of the clearest data a founder gets.
We asked founders and brand leaders building on Shopify to share the mistakes they still think about—and the lessons they carried forward.
Here’s what they said.
1. Own the problem before it owns the story
Hannah Beals, former CEO of Ouai, remembers one of the brand’s first major product launches: a dry shampoo foam. At launch, it seemed like a win. The format felt new, influencers loved it, and the product sold quickly.
Then customers started reporting a quality issue: The cans were exploding.
“It was turning people’s bathrooms and cars and gym bags into a foam party,” Hannah says.
For a young beauty brand, the defect could have become a PR nightmare. Instead, Ouai decided to meet the moment directly. The team replaced affected products, handled customer service quickly, and then did something riskier: They made the mistake part of the conversation.
They reposted customers’ “foam parties,” joked about the chaos, and even created their own version of mean tweets by reading critical reviews out loud.
“I think people just appreciated that we addressed it head on. We were honest about how we were solving it, and we had a sense of humor about what had happened,” Hannah says.
The lesson wasn’t that every mistake should become content. It was that customers can tell the difference between a brand hiding from a problem and one taking responsibility for it.
2. Let your community see the messy middle
Good Girl Snacks cofounders Leah Marcus and Yasaman Bakhtiar have had their share of operational panic moments. One of the most memorable happened when about 200 PR boxes broke in transit—and the carrier delivered them anyway. Influencers opened their doors to broken glass and leaking pickle juice.
Another PR run had the wrong tape, wrong inserts, and no clear explanation of what was inside. On the logistics side, a full pallet of product was sent to the wrong warehouse, leading to an expensive process of rerouting it.
Instead of pretending those moments never happened, the Good Girl Snacks team talked about them publicly. Videos about the broken PR boxes took off because they showed the reality behind the brand.
“We always make a moment out of these panic or disaster situations because those are the videos that go viral,” Leah says. “People were like, ‘Oh my God. Thank you for being honest. I’ve never seen a brand talk about that before.’”
That openness has shaped how customers respond when things go wrong. Leah says even customer emails tend to sound more like messages to friends than complaints to a faceless company.
The mistake became proof of something bigger: When a brand builds real community, customers are more willing to extend grace.
3. Speed is powerful—but it creates cleanup work
Pia Mance, founder of Heaven Mayhem, credits speed as one of the reasons her accessories brand grew quickly. Her philosophy has often been “Done is better than perfect.”
That bias toward action helped the brand take opportunities quickly. But Pia says she’s also learning when to slow down, especially around decisions that affect operations, hiring, or major product moments.
One costly lesson arrived before a crucial Black Friday weekend, when 2,500 units of the brand’s bestselling eyewear arrived at its Atlanta warehouse packaged incorrectly.
“All the units arrived … all wrong, packaged wrong,” Pia says. “So someone from our team had to fly there. She took her sister on a vacation and they sat there for three days unpacking and packing 2,500 units.”
Pia owns the mistake directly: “That was my mistake.”
The fix required time, travel, and manual labor. It also forced a founder-level realization. Moving fast can be a competitive advantage, but the faster a company moves, the more important it becomes to build systems that catch errors before they escalate.
4. Take responsibility, even when it hurts
In the earliest days of Hedley & Bennett, founder Ellen Bennett landed what felt like a huge order: 150 aprons for a restaurant opening. It was the biggest order the company had received by far, and the deadline mattered.
Then the embroidery came back wrong. The team missed the shipping cutoff. The restaurant was about to open without the aprons it had ordered.
“We failed them,” Ellen says. “And we ended up giving them the aprons. We gave them 150 aprons.”
At the time, Hedley & Bennett didn’t have the money to comfortably absorb that cost. But Ellen decided they had to own the mistake.
“I did it because I wanted him to know that we were taking responsibility for the mistake that we made,” she says. “I wasn’t doing it for anyone other than our own integrity.”
The lesson was bigger than one order. Early customers aren’t just transactions; they’re trust tests. When something goes wrong, how a founder responds can say more about the business than a flawless delivery ever could.
5. Don’t throw money at a story problem
Rosie Jane Johnston, founder of By Rosie Jane, has learned that not every growth problem can be solved by spending more.
When something wasn’t working—a fragrance wasn’t connecting, growth felt slow, or the brand needed more attention—her instinct was to reach for a bigger external solution: more influencers, a stronger PR agency, more money behind the problem.
“That is never what moves the needle,” Rosie says. “It has to come back to storytelling. It has to come back to quality of product.”
She remembers spending thousands of dollars early on printing letterhead, envelopes, and business cards before she had fully proven what the business needed.
“I probably spent $5,000 just printing letterhead,” she says. “I don’t even know what I was thinking.”
Her takeaway: Money can amplify what is already working, but it rarely fixes a weak foundation. If the story is unclear, the product isn’t connecting, or the customer need is fuzzy, paid help will only get a business so far.
6. Focus where customer attention is strongest
Lauren Gropper, founder of Repurpose, says one early mistake was trying to educate too many customers in too many places at once.
The sustainable tableware brand had a limited marketing budget and a product category that still required explanation. But instead of going deep in the markets where consumer buy-in was strongest, the company tried to spread the message broadly.
“We probably only had consumer buy-in on the West Coast, maybe some of the Northeast Coast,” Lauren says. “I would have focused more heavily on those markets and just gone very deep there versus trying to peanut-butter spread across the country.”
The lesson still applies even when ecommerce makes products available everywhere. Availability is not the same as focus. A brand can sell nationally while concentrating marketing dollars in the places where the message is most likely to land.
For founders with limited resources, depth can beat breadth.
7. The wrong hire can be one of the most expensive mistakes
Beautyblender founder Rea Ann Silva has built her company over more than two decades. Looking back, some of the most costly lessons weren’t about product, but people.
“The only way you learn is through your mistakes,” Rea Ann says. “For me, what I have learned in the most dramatic way is the people that you surround yourself with are the most important lessons.”
Hiring the wrong executive or team member can slow a business down in ways that are difficult to measure at first. But if they’re not the person who can help the company get where it needs to go, the cost grows over time.
“I have hired slow and fired slow, and it has hurt me,” Rea Ann says.
Her lesson is one many founders learn painfully: Building the right team is not just about bringing people in. It is also about knowing when to let someone go.
8. Turn hindsight into data, not regret
Michael Petry, cofounder of Golden West Boots, doesn’t like to describe hard moments as mistakes. He prefers to treat them as learning opportunities.
“I don’t look backward on that,” he says. “I look backward for learnings. My brain is always on the front foot.”
For Michael, the danger isn’t reflection—it’s getting stuck in regret. If a marketing event doesn’t drive the expected traffic, the team can use that result as a benchmark for next year. If a decision doesn’t go as planned, it becomes information for the next decision.
“If I’m looking at my rearview mirror, how am I going to tell you what’s happening in spring 2027?” he says.
The distinction matters. Founders need to review what happened, but not live there. The goal is to extract the lesson and keep moving.
The mistake is part of the job
Every founder or brand leader in this group has dealt with a moment that didn’t match the plan: broken PR boxes, defective products, wrong packaging, missed deadlines, unfocused marketing, expensive hires, and ideas that needed to be reworked.
What they have in common is not perfection—it’s response.
They owned the problem. They protected the customer relationship. They turned public messes into trust-building moments. They learned when to move faster and when to slow down. They let the mistake become data for the next decision.
Building a business is iteration. You test, miss, learn, and make the next decision better.
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