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"How Do You Know When to Pivot?" Here's What 13 Businesses Actually Did
00:24:15
Founders of thirteen businesses building on Shopify share how they navigate the pivot—when to leap, when to walk away, and how to tell fear from excitement. Insights from the founders of LORE, Fly By Jing, OSEA, Loftie, Avocado Green, and more.
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- [00:00]
Host
Nobody warns you about this part of building a business, that the right decision and the hardest one are sometimes the same thing.
- [00:07]
Melanie Bender
Roles that I took that were the most exciting, that had the greatest payoff for me, I was terrified of them.
- [00:13]
Host
That fear you feel is a signal that you're onto something worth chasing.
- [00:17]
Kathryn Goetze
My gut has never steered me wrong in my whole life.
- [00:22]
Host
And the best move can be doing what actually scares you, because the cost of standing still is rarely felt until it's too.
- [00:29]
Jing Gao
Even though sometimes something is shiny, it doesn't mean it's the right thing for the business.
- [00:33]
Host
Change is never easy. But for every founder who built something that lasted, it was necessary.
- [00:38]
A.C. Hampton
Every part that I thought was the worst part, actually, in hindsight, was like the best thing that could ever happen.
- [00:43]
Host
13 founders on the hard calls that turned out to be the right ones. Let's go. An AI educator who built a phone designed to disconnect you. That's not a contradiction. Founder of Physical Phones Kathryn Goetze opens the conversation, starting with the one thing most founders forget to listen to.
- [01:01]
Kathryn Goetze
My gut has never steered me wrong in my whole life. I was thinking about it the other day, I'm like, how wonderful is it that we are born into this world with this, like, cosmic compass inside of us that can just, like, always tell us what to do? The challenge is actually following it first, being able to hear it, and then second of all, actually trusting it enough to go in that direction. I mean, there have been a lot of kind of, kind of pivots in my career when I decided to quit my full time job and go all in on content when I decided to leave tech and start making videos again. But the funny thing about gut is, like, it is painfully poking you when you're not listening to it. But when you are listening to it, it's not like it celebrates you or congratulates you. It just goes dead quiet. It only ever rears its ugly head with that poking feeling when you're misaligned. And so as I've gotten older, I've realized that the sooner I can just do what my gut is telling me to do, the better things turn out. And that could be, you know, entering or leaving certain relationships, you know, personal or business wise. It could be about deciding what to work on next or what to pursue. I think another guiding light is if you have one idea that you just for some reason cannot seem to put down, like, it just, like, keeps kind of coming back to you, especially if it's been like weeks or months or years, you should probably go give that idea a shot. And that was another thing again for physical phones. For me, it was like, tried it. Two years later, I was like, I'm still thinking about this damn Bluetooth phone. Okay, maybe I should make a video about it. And I remember telling my team at the time, I was like, I'm gonna start posting some content that is gonna not make sense before it makes sense, but trust me, it will make sense. Sure enough, it worked out. But there's a lot of trust that goes into that process.
- [02:50]
Host
Listening to that inner voice is an incredibly important and, like, true life hack of a compass. Many of us are really good at ignoring it or not even fully knowing how to tune into it.
- [03:04]
Kathryn Goetze
I think you have to be able to hear your own thoughts, and I think that it's really hard to hear your own thoughts if the second you wake up, you start blaring blue light directly into your retinas with an onslaught of notifications from 5,000 things you don't actually even care about. You want to be a great business owner. You want to build your dream life. You have to actually know what your gut is telling you and what you want to do. So you have to actually be able to step away from the noise of the notifications and the scroll and yes, use AI to build your dream life. But first step completely away from it and get so quiet that you actually know what that even looks like for you. Some of the most productive hours of my week, at least at least three to five hours a week for me, are spent laptop closed, phone away. I have a pad of paper and a pen, and I'm literally looking out of a window just thinking about, like, did the actions I did this past week actually align with where I want to be in a year from now? Okay, if the answer is no, like, why didn't it align then? When you do come back to the chaos and the noise and working with other people, you actually know what you're supposed to be spending your time on.
- [04:12]
Host
Fear and excitement can feel almost identical. LOR Founder and CEO Melanie Bender has a test for telling them apart.
- [04:20]
Melanie Bender
Transitions are hard, right? There's a lot of unknowns. Maybe it's coming in the form of what feels like failure of something that didn't work out how you thought it would. But I think each of those transitions can bring huge opportunity. For me, one of the biggest things was learning to understand the difference between excitement and fear. I think, without exception, the roles that I took that were the most exciting, that had the greatest payoff for me. I was terrified of them. I was terrified to take that leap and take that risk. And I considered not taking them and was incredibly fortunate to work with a wonderful coach who said, well, Melanie, are you afraid or are you excited? And the difference is what it comes from, because they can feel really similar. Your hire's racing with both, you're unsure with both. But fear is the risk of pain, whereas excitement is the risk of potential. And when I kind of stepped back and thought about that, it helped me see that, okay, I am incredibly excited about the potential of these. And, yeah, I'm afraid I'm going to fail. I'm afraid I don't have what it takes, but I can deal with that. I can manage that by being clear about my strengths, being clear about my opportunities and where I need to beef up to do well, but also just kind of accepting that fear as part of doing something that is incredibly exciting and wonderful.
- [05:46]
Host
Sometimes the pivot is away from something that's working. Jing Gao, founder and CEO of Fly By Jiang, on why she cut a successful product line on purpose.
- [05:55]
Jing Gao
I've always been the type of person that learns through doing and learns through experimenting. I don't really dig my heels into choices that I make. I feel like every choice or every scenario is a chance for learning. And I try to, you know, go back to first principles a lot and, like, stay curious and open and ask questions and ask questions of my own, myself and also of my team. And the way that our company culture works is that we just, we don't make assumptions, we stay curious. And I think through that line of questioning, you start to see, okay, well, if this is not working well, what do we do? What do we change within flybiging, We've pivoted towards and away from product lines many times, and we try things out, and if it works, it's great. Sometimes it works, but you still need to pivot. For example, we had a line of frozen dumplings at one point, and it worked really well. We're selling so many frozen dumplings, but we realized that it was diverting attention away from our core, which was our sauces. And our sauces are shelf stable. They have much better margin structure than something that's frozen. So even though sometimes something is shiny and bright, it doesn't mean it's the right thing for the business. And we decided to cut that line completely in order to stay focused.
- [07:16]
Host
He doesn't coast. He's ahead of the changes. Supreme E. Com founder and CEO A.C. hampton explains why getting to the frontline matters.
- [07:24]
A.C. Hampton
More than anything, you have to be open for change and you cannot get stuck behind. I mean, I can name off multiple, like the iOS 14 update that happened with Meta and how that stopped allowing people to track, and then now your ads are not showing the right type of metrics. And I then had to start using things called UTMs to track it. On the Shopify side, I had to get other softwares like triple well, to help out with being. Being able to still see like the real data. I've always been a forefront of change because, I don't know, I just get stuck in that mindset of like that Blockbuster Netflix thing and how, you know, Blockbuster had the chance of being like the biggest company in the world. And, you know, Netflix, this little small company came in and was like, hey, you know, we are thinking about really trying to make this an online thing or getting these boxes or, you know, making it more digital. And they're like, no, you know, where this is our business, this is our model. And then within three to five years, they went completely bankrupt. And, you know, Netflix is now like one of the biggest companies in the world. And all Blockbuster had to do was listen. And so to me, it's being able to listen, see what's happening in the, in the space around and just being able to adapt. And, you know, adapting takes a lot of effort, it takes a lot of time, and sometimes it's like, oh, my God, I have to now learn this on top of everything else again. But it's a challenge, and I like challenges. So even this whole AI surgeon, I mean, this has been something that I've taken as a big responsibility for myself as a CEO of being like, how do I learn this to help our students? And how do I learn this to help the employee productivity inside supreme as well? So just being willing to get your hands dirty, I think if you take too far away and you don't, like, see what's really happening on the front line, then you can never keep the velocity moving at the right type of speed.
- [09:04]
Host
Fail fast is everywhere. OCS CEO Melissa Palmer has a better version. She came to it through a hula hoop company she walked away from, and what that experience actually gave her the
- [09:15]
Melissa Palmer
gift of failing and moving forward is one of the most untalked about things in entrepreneurship. I left the hula Hoop company kind of with like my head down, and I remember someone pulled me aside and said, it's actually like the best thing for you to fail. I realized that it actually was the biggest gift because I learned everything I needed to for the next chapter. And it sparked something inside of me to want to succeed in a way that I never had. Some really wise entrepreneurs that I've seen have built this muscle of actually, like, choosing to walk away before you fail. Sometimes not every idea works. Like, you can start building something and change your mind. I think that there's such an opportunity to just, like, give yourself freedom to move on to the next thing and, like, follow that next gut or to just, like, let a failure take you to what's next.
- [10:20]
Host
Hanging on the mane of a lion Coop sleepgoods co founders Kevin and Jin Chan on what it's like when change is just the baseline. There can sometimes be this anxiety that crops up of, like, well, I'm pot committed, and, like, I better stay in it, because, like, what will they think if I leave it behind? But we also live in this world where, like, everything is moving so quickly. People forget things so fast.
- [10:46]
Aishwarya Iyer
It's, like, great, you failed.
- [10:48]
Host
Whatever. People will forget in five seconds. Go do the next thing. Yeah.
- [10:51]
Melissa Palmer
And you can also fail in an honorable way, too. Like, you can just, like, fail fast and say, like, hey, it didn't work, but I'm trying this now.
- [10:58]
Host
Yeah.
- [10:59]
Melissa Palmer
And instead of getting so stuck in, like, the story of what happened, there's something else coming next.
- [11:06]
Kevin Chan
I don't know about one pivot, but it's just been a tornado. Like, you're hanging on the back of a mane of a lion, and it's, like, running through the jungle, and we're just hanging out for dear life is kind of what it felt like. And so I think the common thread or theme through all of it was, like, change is normal. Get used to it. And, like, there's no boundaries. Like, every day we're learning something new, and there's no rules, nothing sacred. And so I think that became our norm. And in some weird way, it's like, one day I felt like I woke up. I was like, how did I become this person? You know? And one day you do that. Just things change and you become someone new. And, you know, as a team grows, then, like, you also got to pull back. You get new leadership. You got to give up things and let people lead. And so that was another season of just, like, really transformation and growing in a different way for me. And so, yeah, I've been really stretched in so many ways, but I've grown tremendously as a human. It's been a blessing of a journey.
- [12:04]
Matt Hassett
Jen, do you resonate with that as well?
- [12:06]
Sean Reyes
That bumpy ride through this change roller coaster, yes.
- [12:09]
A.C. Hampton
100%. Going from something that we call stable.
- [12:13]
Melissa Palmer
Right.
- [12:13]
A.C. Hampton
As an attorney, you think, I'll always have a job, I'll have security. But I think through our entrepreneurial journey, I realized that's actually not stability. We've created our own stability by starting our own business. By taking, you know, the lion by the mane and holding on and going through that journey, I think that's been very eye openening for me. And going through this process has also given me the confidence to know that no matter what, I can always start something new and we'll figure it out and it'll be successful. That's the biggest thing is, like, the confidence that comes from it. There, to Kevin's point, has been so much change. I've also had three kids while we were building this business, gotten married and all of those things. And through every time, every part that I thought was the worst part actually in hindsight, was like the best thing that could ever happen. And I think when we get into challenging moments, you have to remember that to know that, like, moving forward, it's gonna be okay.
- [13:04]
Host
Is change happening to you or for you? Brightland Founder and CEO Aishwarya Iyer on the mindset shift that changes everything.
- [13:12]
Aishwarya Iyer
Change is inevitable. Like, we can say that it's happening to us or happening for us, and that's just up to us to decide which way we want to look at it. It's coming, it's happening constantly. Our cells at a, like a very, you know, molecular level are changing every single second. I resented it, slash grieved it at a higher level. Like, I just lost two dogs recently. You know, like, with life's changes, sometimes you're like, oh, my God, I want to go back to what was. But there's always more that's coming. And so you just have to look at it that way. And I think it's a mindset, honestly, like, do you want change happening to you or do you want it happening for you?
- [13:53]
Host
It makes me think of my friend Ellen Bennett, who is the founder of Headley and Bennett, and she said something along the lines of, like, not making a decision is a decision. Yes. You know, I couldn't agree more. Are there times in life where your fear came up and you decided not to make the shift, not to make the pivot, not to jump off the cliff that you regret?
- [14:17]
Aishwarya Iyer
I would say it's usually around people, like making a call on somebody that it's not working. A lot of those I knew, but I waited, thought maybe it could change. Maybe the circumstance would change, that person would change. And that's just. It hasn't been my case once, you know, just make the call on it.
- [14:38]
Host
Two pivots changed Matt Hassett's entire career and his process for building his company Lofty.
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Matt Hassett
The biggest pivot for me career wise was becoming a product designer and an inventor. I think I had always been an inventor. In high school, I started a student newspaper that we had to pay for ourselves. The school didn't pay for it. In college, I started a student run restaurant. So there was this passion in me to start new things. And in my early part of my career, I worked for the city of New York, for the state of New York, a lot of nonprofits, and I was trying to help people recover from the mortgage crisis. I was graduating right into the Great Recession. And so I spent a lot of time making new products and programs to help people, loans to help people backed by the city. So there's a lot of no's at the city of New York. No, we can't do that. I do. It's like, oh, that's interesting. Let's try that. And so it was just, it was exactly the type of people that I needed in my life and I didn't know I'd been missing. And so that really changed how I approach the world. One of the first things I learned sort of in the crash course to ideo, that there's always this urge to kind of bring it back to earth and like, okay, well, this is very interesting. You know, it's been nice to learn about how squirrels bury nuts, but how does that relate to frequent flyer points? And actually it's very similar how they relate. But, you know, the idea designer wants to keep studying the squirrels and learn about how they store the nuts around the yard.
- [16:01]
Host
He inherited a family business and scaled it into a global brand. Avocado Greens CEO V Nguyen on how he made that transition.
- [16:10]
V Nguyen
One of the things I probably learned a little too late is, you know, bringing in real solid talent that has unique domain expertise. I think a lot of times small businesses, you get stuck in that sort of mentality where, you know, the owner, the founder sort of ends up doing a little bit of everything.
- [16:30]
Host
Gotta wear all the hats.
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V Nguyen
Yeah, you wear all the hats. Partly. Sometimes it's stuck because you don't have the resources and everything. But there's certainly somebody better at marketing than I am. There's somebody better at the storytelling than I am, and then there's other people that are better at operations. And then I think trying to sort of come to a realization and acceptance of doing that sooner than later, I think is a huge thing that can help propel the business.
- [16:54]
Host
There's always the hats that you're wearing that you're very happy to take off.
- [16:58]
Aishwarya Iyer
Right.
- [16:59]
Host
And then sometimes you got to give up hats that are actually near and dear to you.
- [17:03]
V Nguyen
Yeah. And if you find somebody who's better than you at it, I think you have to be, you know, sort of strong enough in your own skin to be like, hey, this. This person is much better at me and this. So I should, you know, relinquish some responsibility here. My biggest weakness, I think early on was that I hadn't developed a network big enough. You know, you end up hiring friends or people, you know, and then if your network is only so small, you sort of, you know, you're fishing in a small pond. One of the things I really did over time was really worked at making sure I expanded my network both within the industry, but outside the industry. You know, I sit on all these like CEO type dinners and meet meetups now, and that's helped me meet a lot of different people. That was something probably the first five, six, seven years I didn't do as much of.
- [17:46]
Host
He had a 200,000 subscriber fashion channel and walked away from it. Drew Scott shares why he pivoted to interior design content with Lone Fox.
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Drew Scott
Honestly, like, I'm very much the kind of person that kind of just dives all in. That's just my mentality and kind of who I am. If I feel good about it, then I just will do it. So I remember I was with a manager and I was like, oh, I think I'm gonna stop my men's fashion channel. And she's like, well, that's like where you're making all your money. Because I was only had about 100,000 subscribers on the Lone Fox channel at this time, and it was just starting to get some interest from brands. But I definitely did take a big risk. So stopping that fashion channel because I really wanted to go full on with the interior channel. I just felt so much more passionate about it. And the videos were doing better, but they also took me so much more time. Like, that's what I really invested a lot of time into, the Lone Fox channel.
- [18:35]
Host
It feels to me like you had this sort of looseness around it where you were like, it's not my identity, it's just kind of like the thing that I'm doing and I'm interested in right now.
- [18:42]
Drew Scott
Honestly, throughout doing those Few different kind of brands or different versions of myself. I guess when I was younger, it made me realize that when I created Lone Fox, I wanted it to be an actual brand. Like, I wanted it to be Lone Fox. I didn't want it to be Drew Scott or like.
- [18:58]
Host
You knew that.
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Drew Scott
Yeah, I knew right away. I wanted it to be more of a brand that I can like, build something around and an image and then people can like, envision themselves investing in as well.
- [19:09]
Host
You had the cooking blog for a little while.
- [19:11]
Drew Scott
I had a cooking blog. I don't even cook. Like, I don't know why I had that.
- [19:14]
Host
Your sales doubled between. More than doubled, actually, between 2024 and 2025.
- [19:21]
Kevin Chan
Yeah.
- [19:22]
Host
Looking in hindsight, was there like any strategy or something specific that you put in place that you think contributed to that kind of growth?
- [19:31]
Drew Scott
Honestly, it really was like the switch in my product collection. Like it was before, like a lot of contemporary products or things that you can buy wholesale and then you resell. But. But the thing I noticed about that is, like, anyone can buy those and anyone can resell them. And I would like look at my $30 vase and find it for 21 on Amazon. So I started to realize, like, I need to change my product assortment. And people were loving the vintage I was using in my projects, but I didn't know how to get that to them. So I was like, why don't I just start selling it on my website? Everything's just so one of a kind and unique. Like, we don't sell the same product twice. We'll like upload a hundred products and by the next day half of them are gone. Every single time he was selling video
- [20:10]
Host
game characters at 12, made it to Blizzard, then walked away from it all. Shock Surplus founder and CEO Sean Reyes on why the straight line was never the point.
- [20:20]
Sean Reyes
I started playing video games very young. Started selling video game characters when I was 12 years old. That kind of blossomed into a short career at Blizzard Entertainment. And you know, just through all of that, I really. Freedom of time was always the most important thing. Like I'd rather be sent home early rather than sit around and do nothing, you know, so money was never really the. The thing for me. It was always time, freedom, and being able to do, you know, whatever I wanted. You know, I'd say if you're. You have that same itch and you want the freedom, then there are so many ways to go about doing that nowadays. The follow your passion. I think there is a lot to that, especially nowadays when, like, you can Provide value in so many forms to so many different audiences, even, even a humanities major that studies European history, you can go on to TikTok, do book reviews, visualize the book reviews and still make money. You know, that was not possible 10 years ago. Right. And so all this, all the mantra about, like, don't follow your passion because it's not going to lead to economic opportunity like that. That kind of game is changing dramatically nowadays. And so don't follow the playbook from five years ago on seeking economic opportunities. Try to understand all the ways that you can provide value in your specialized interest to the greater audience.
- [21:48]
Host
The pandemic closed every door behind them. Carmen, Diane and Kara, still co founders of Prosperity Market, on the moment they realized there was no path back and why that was the clarity they needed.
- [21:59]
Carmen, Diane, and Kara
I don't think anyone was surprised at the pivot. Maybe a mobile farmer's market, like, that's, that's new, that's unexpected. But no one was surprised by the fact that I had some idea that I was following. For me, people were just more curious,
- [22:15]
Host
like, what is it that you're doing?
- [22:18]
Carmen, Diane, and Kara
There was no surprise that the thing that I was doing was something that involved making a difference for people. That wasn't a surprise for people.
- [22:27]
Host
On a personal level, was there any trepidation to make such a big life change?
- [22:34]
Carmen, Diane, and Kara
I felt really good about switching. I don't know that I knew I was switching at the moment, but everything happened so seamlessly that I never looked back. It was one day I already wasn't working because we were in the middle of the pandemic. There was no tv, there was no film being made, and I was putting all of my time and energy into this idea that we had. And when the world opened back up, we were so far deep into what we were doing that it was never a thought of going back. Yeah, there was no space to go back. By then, we had done so much so fast. There was no time to go back to anything else. It just felt like the thing that I was going to do next. And I think we had such peace about it because it really was meant for us to do this.
- [23:21]
Host
Thirteen years running, one of the most beloved home brands in the business, Lulu and Georgia founder and CEO Sarah Sugarman closes the episode with one reframe. What if the change wasn't the obstacle, but the signal? Our team has really learned how to be resilient and approach change not as an obstacle, but as an opportunity. And once you start to see changes as opportunities, I think that they're no longer as scary and really confident be drivers for the business. It's really staying deeply rooted in our mission and our commitment toward that mission, which is to bring, you know, beauty home. If this one hit close to home, drop a comment and tell us what resonated or share it with a founder who needs to hear it right now. Subscribe to Shopify Masters so you never miss the real stories behind the businesses you love and click the link in the description to start your business today. Thanks for tuning in.