The Mistakes That Changed Everything (From 8 Real Businesses)

Host: These are the parts of building a business that does not show up in the launch photos or highlight reels.

Leah Marcus: We had all of our PR boxes break.

Ellen Bennett: We didn't deliver on the day it needed to ship.

PM Ants: Two and a half thousand units arrived all wrong, packaged wrong.

Host: But the best founders don't pretend mistakes aren't happening. They own them, fix what they can, and use them as data for the next decision.

Rosie Jane Johnston: You can't just throw money at a problem and expect it to go away or be a silver bullet.

Hannah Beals: People just appreciated that we addressed it head on.

Host: Sometimes the mistake is expensive, sometimes it is public.

Ellen Bennett: Every day I felt like we were on the verge of collapse.

Guest: I've learned very costly lessons.

Host: In this episode, we are hearing from founders who have stumbled, recalibrated, and have come out with hard won lessons for what comes next. So let's get into it. First up, a product issue can turn into a PR nightmare fast. Hannah Beals, the former CEO at Ouai, explains how the team turned that PR nightmare into a viral sensation.

Hannah Beals: We launched very early. One of our first innovation launches was a dry shampoo foam, which was really cool. At the time. No one had seen that format of dry shampoo. It was like you poofed it into your hand and rubbed it in. It felt wet, but eventually dried out and made your hair feel super clean. And so it was a new format that people hadn't experienced. And we were really proud of the innovation and it sold like gangbusters. Cause there was a lot of great influencer pickup when it launched. And like we had an incredible launch for it. And then once it was in market, it turned out there was a little bit of a quality issue and it was exploding in people's bathrooms. It was like in, in a way that like, you couldn't believe how much foam this can contained. Like it was turning people's bathrooms and cars and gym bags into a foam party. And so it was a, uh, pretty major quality issue. And it could have been a huge, like PR nightmare for the brand, but we just owned it with a sense of humor and we started reposting everyone's foam parties. We called them in the bathroom and we did like a hashtag that was like, no FOMO or Go big or go foam with your foam parties. We obviously handled it with like incredible customer service experience so that anyone who had that, like, we would replace, send them, um, other products, like no questions asked. But we also did pop. Is it like Jimmy Kimmel? That does mean tweets or whatever. We did our own version of that. That was mean. Reviews of the foam. And just, like, read all of the tweets and the product page reviews of people roasting us for the experience. And 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. And at the end of the day, brands are just run by people who do their best and ultimately make mistakes, so sometimes and have to figure them out. And so that ended up being a win for us as a brand. And to this day, we have people who know us for our iconic exploding dry shampoo foam.

Host: Um, sometimes the disaster is the content. Good Girl Snacks. Co founders Leah Marcus and Yasmin Bhaktiar share why being honest about the chaos actually brought their community closer.

Leah Marcus: On the marketing side, we had all of our PR boxes break this summer, like, 200 of them, and FedEx decided it was a good idea to still deliver them. So you had, like, you know, huge influence influencers. And their first interaction with us is broken glass all over their front door

Guest: and, like, pickle juice dripping out.

Guest: Right.

Leah Marcus: Smells so good. And then our second PR run a few months ago, wrong tape, wrong inserts. No one knew what was going on. It was just like, here's pickles. So that was a mess for me. The, like, logistics piece is really the one that got me and, like, dealing with freight and, like, things like that, uh, like shipments not arriving on time, or I accidentally sent a full pallet of product to the wrong warehouse. And then the company, like, reached out to me, and they were like, hey, what is this? What is this shipment we just received? And then you have to work to reroute the shipment. And then obviously, all these mistakes are expensive as well, so that adds another layer of stress. It's like, not only are you delaying everything, but you're also having to pay to clean up the mess you made. And so, yeah, there's been definitely a lot of my panic moments. We, like, always make a moment out of these panic slash, like, disaster situations, because those are the videos that go viral. Like, we made a video about these 200 PR boxes that broke and it exploded, and we saw a positive out of it because people were like, oh, my God, like, thank you for being honest. I've never seen a brand talk about that before. Yeah. And then, you know, they have respect for us or they follow us or whatever else. And then again, back to the community and, like, authenticity conversation.

Guest: And if people are invested in you, then there's probably more leniency Right, Totally. It's a more forgiving attitude, like, they know you.

Leah Marcus: Yeah.

Host: Moving fast can help you grow, but it can also create expensive cleanup work. Heaven Mayhem founder PM Ants shares how she solved a massive packaging mistake. When you look back, is there anything that you would do differently?

PM Ants: I mean, I make mistakes every day. I think I always say, like, done is better than perfect. Get it done. Just do it. That has helped us so much, and moving quickly and taking loads of opportunities has helped us so much. But I think in the. At the moment, I'm looking to slow down my decision making. I want to, like, be very, very considered, especially when it comes to signing on new things or hiring. Um, and, like, sometimes I make mistakes. For example, it was my fault. I messed up. Something to do with our sunglasses packaging. All the units arrived for our Black Friday sale and for holiday to Atlanta and our bestselling eyewear. I think two and a half thousand units arrived all wrong, packaged wrong. So someone from our team had to fly there. She took her sister on, like, a vacation, and they sat there for three days unpacking and packing two and a half thousand units. So, like, that was my mistake. But it is what it is. You learn from it.

Host: Next, Headley and Bennett. Founder Ellen Bennett shares the order and mistakes she still remembers from the earliest days of the company.

Ellen Bennett: Every day, I felt like we were on the verge of collapse. Some different fashion. I mean, I'll never forget there was an order for Brian Voltaggio, who's Michael Voltaggio's brother. I had met him through Michael. So I felt this, like, need to do everything perfect. And they gave us an order for 150 aprons, which is the biggest order Headley and Bennett had ever done by miles. And they had a deadline. They were opening the restaurant, and we did not get the embroidery right. Like, there was something wrong with it. And we didn't deliver on the day it needed to ship. So we missed the cutoff to ship. And we were freaking out. We were like, the restaurant is going to open without our aprons. And while it's like the last thing you're thinking of in a restaurant opening, it's also the thing that they went out of their way to think about, and we failed them. And we ended up giving them the aprons. We gave them 150 aprons.

Guest: You didn't have the money for that?

Ellen Bennett: Hell, no, we didn't have the money for that. But I did it because I wanted him to know that we were taking responsibility for the mistake that we made.

PM Ants: Wow.

Ellen Bennett: And I think that had a really big impact on them. And I don't even really know if he understood that we were that tiny and that we had absorbed that cost. But it didn't matter. I wasn't doing it for anyone other than, like, our own integrity and letting our customer, who is really our friend know, hey, we're owning our mistake here.

Host: Not every problem can be fixed with a bigger budget by Rosie Jane Founder Rosie Jane Johnston breaks down the lessons she learned about money, marketing and why storytelling matters.

Rosie Jane Johnston: You can't just throw money at a problem and expect it to go away or be a silver bullet. And I learned that by, oh, uh, well, this isn't working. Or we're not growing, Someone's not loving this fragrance. Let's just, you know, pay influencers to do it, right? Or let's just get a bigger and better PR agency. That is never what moves the needle, right?

Guest: It.

Rosie Jane Johnston: It has to come back to storytelling. It has to come back to quality of product. But that and I think also how much money it takes to start a business. When I very first started, I printed all this letterhead. I mean, this is why it's so old school, right? When I did the first, like, cheek and lip gloss, I asked my dad, hey, can you help me? I want to print. I letterhead. I had envelopes, I had business cards. I probably spent $5,000, right, just printing letterhead. And I was like, what? I don't even know what I was thinking. It's just taking it slow. Trying to rush something, trying to, you know, push through. It's sometimes too much money is not the answer.

Host: Growth is not just about reaching more people. It is about reaching the right people. Repurpose founder Lauren Groper shares why trying to spread the brand too broadly too early made marketing harder than it needed to be.

Guest: We made so many mistakes. I mean, on the education side, we didn't have the budgets. I mean, we had really minimal marketing budgets. We were like living on a shoestring to be able to do anything. And so it was sort of early days of social. We relied on that and influencers and whatnot. But really you're hitting like a tiny fraction with the budgets that we had. So I think what we did was probably try to penetrate too much of the market early on, when really we probably only had a, you know, a consumer buy in on the west coast, probably maybe some of the, you know, northeast coast, really, it was like a coastal thing and maybe some pockets of, you know, various metropolitan areas throughout the country. But it was not widespread across the country in terms of just awareness or desire for these kind of products. So I would have focused more heavily on those markets and just gone very deep there versus trying to kind of like peanut butter spread across the country and, you know, support that. It was really hard.

Guest: Is that a piece of advice that you would still give to founders in this space today? Narrow the focus or do you feel like the landscape has changed stuff?

Guest: I think the landscapes have changed so much, especially with E commerce. You can really, I mean, you can be available for everyone everywhere. But I would focus my marketing budget. Yes. On those areas that I feel have the strongest consumer market for my product.

Host: Some of the most expensive mistakes are mistakes you make when building a team. Beautyblender founder Rianne Silva talks about leadership and the cost of keeping the wrong hire for too long.

Guest: The only way you learn is through your mistakes. Right. I mean, for me, what I have learned in the most dramatic way is the people that you surround yourself with are the most important lessons. Right. Learning how to identify the right executive, the right team member, the right person that is going to help you get where you're going to. Now they're all going to tell you they are, but how to identify that they are the right person. And really, I know maybe the next question is, oh, Rhiann, how do you do that? Well, you. Only for me, it's been through hiring the wrong people that I've learned very costly lessons through.

Host: Um, what do they say? Hire slow fire fast.

Guest: They do. They do.

Host: There's a reason for that.

Guest: Yeah, yeah. And I have hired slow and fired slow, and it has hurt me.

Host: So I've learned not every founder likes the word mistake. Golden West Boots founder Michael Petrie sees those moments as learning opportunities instead of,

Guest: my brain is always on the front foot. I'm always moving forward. Uh, you know, we haven't made any mistakes, but maybe somebody else from the outside would say, well, they could have done this, but if I live in that space and generally I wake up m, my natural resting position is very positive. And I just talked about. Actually I had a meeting this morning and I said, I don't view things as mistakes. I view things as learning opportunities. Could we have done something better or, you know, we had a couple marketing events that people wanted to have more down funnel traffic. But the argument back on that would be, we learned and now we can benchmark next year on how we're going to get more down funnel traffic. But in our first year, we're able to now have these learnings. So I don't look at those things as, you know, mistakes or it didn't go as well as we thought. Those are just clear opportunities to do better. And that's how, uh, I sort of look at those things. So to me, it winds back almost being data driven. I never want to look backwards. If I'm looking at my rearview mirror, how am I going to tell you what's happening in spring 2027?

Host: Building a business is iteration. You test, you miss, learn, and make the next decision better. That is why Shopify Masters exists to be your companion as you start, scale, and learn from founders doing the same. Thanks for tuning in. Subscribe for more and click that link in the description to start your free Shopify trial today. We'll see you next time.