"How Do You Know When to Pivot?" Here's What 13 Businesses Actually Did

0:00Nobody warns you about this part of building a business, that the right decision and the hardest one are sometimes the same thing. Roles that I took that were the most exciting, that had the greatest payoff for me, I was terrified of them. That fear you feel, it's a signal that you're onto something worth chasing. My gut has never steered me wrong in my whole life. And the best move can be doing what actually scares you, because the cost of standing still is rarely felt until it's too late. Even though sometimes something is shiny, it doesn't mean it's the right thing for the business. Change is never easy, but for every founder who built something that lasted, it was necessary.

0:37Kevin Chon:Every part that I thought was the worst part, actually in hindsight, was like the best thing that could ever happen. 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, Catherine Getzee, opens the conversation, starting with the one thing most founders forget to listen to. 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're born into this world with this cosmic compass inside of us that can just always tell us what to do?

1:16The 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 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.

1:53And 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. It just keeps kind of coming back to you, especially if it's been 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.

2:29Two 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 going to start posting some content that is going to 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. 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. I think you have to be able to hear your own thoughts.

3:07And 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 and get so quiet that you actually know what that even looks like for you.

3:40Some 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 And 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. Fear and excitement can feel almost identical. Laura founder and CEO Melanie Bender has a test for telling them apart.

4:20Transitions 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 that. and was incredibly fortunate to work with a wonderful coach who said, well, Melanie, are you afraid or are you excited?

5:04And the difference is what it comes from because they can feel really similar. Your hires 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.

5:45Sometimes the pivot is away from something that's working. Jing Gao, founder and CEO of Fly by Jing, on why she cut a successful product line on purpose. 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 go back to first principles a lot and stay curious and open and ask questions and ask questions of myself and also of my team. And the way that our company culture works is that we just don't make assumptions. We stay curious.

6:26And 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 FlyBuyJing, 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.

7:07So 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. He doesn't coast. He's ahead of the changes. Supreme Ecom founder and CEO A.C. Hampton explains why getting to the front line matters more than anything.

7:24AC Hampton: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 Triplewell to help out with 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.

7:58AC Hampton: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 making it more digital. And they're like, no, this is our business, this is our model. And then within three to five years, they went completely bankrupt. And Netflix is now 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 space around, and just being able to adapt. And adapting takes a lot of effort. It takes a lot of time.

8:30AC Hampton:And sometimes it's like, oh my God, I have to now learn this on top of everything else. But it's a challenge. I like challenges. So even this whole AI surge, 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 see what's really happening on the front line, then you can never keep the velocity moving at the right type of speed.

9:03Fail fast is everywhere. Osea 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.

9:14Kevin Chon:The 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.

10:02Kevin Chon: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. 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.

10:44People forget things so fast. It's like, great. You failed, whatever. People will forget in five seconds. Go do the next thing.

10:51Kevin Chon:Yeah. 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 yeah and instead of getting so stuck in like the story of what happened there's something else coming next 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 we're just hanging out for dear life it's 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.

11:26Like 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 and I was like, how did I become this person? And one day you do that, things change and you become someone new. And as the team grows, then 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 this 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.

12:02It's been a blessing of a journey. Jen, do you resonate with that as well, that bumpy ride through this change rollercoaster?

12:08Kevin Chon:Yes, 100%. Going from something that we call stable, right? 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 the line by the main and holding on and going through that journey. I think that's been very eye-opening 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.

12:43Kevin Chon: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 going to be okay. Is change happening to you or for you? Brightland founder and CEO Ashwarya Iyer on the mindset shift that changes everything. Change is inevitable. Like we can say that it's happening to us or happening for us.

13:17Kevin Chon: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 very molecular level are changing every single second. I resented it slash grieved it at a higher level. I just lost two dogs recently. 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? It makes me think of my friend Ellen Bennett, who is the founder of Hedley and Bennett.

13:57And 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?

14:17Kevin Chon: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. Two pivots changed Matt Hassett's entire career and his process for building his company Lofty. The biggest pivot for me career-wise was becoming a product designer and an inventor. I think I'd always been an inventor. In high school, I started a student newspaper that we had to pay for ourselves.

14:56The 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.

15:29And 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 approached 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 IDEO designer wants to keep studying the squirrels and learn about how they store the nuts around the yard.

16:00He inherited a family business and scaled it into a global brand. Avocado Green CEO V. Nguyen on how he made that transition. 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. and... Gotta wear all the hats. Yeah, you wear all the hats. Partly sometimes it's stuck because you don't have the resources and everything. But, yeah, there's certainly somebody better at marketing than I am.

16:38There'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. There's always the hats that you're wearing that you're very happy to take off, right? And then sometimes you got to give up hats that are actually near and dear to you. 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 person is much better at me than this.

17:11So 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 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.

17:46He 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.

17:54Drew 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 going to 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 stopping that fashion channel because I really wanted to go full on with the interior channel.

18:25Drew Scott: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. 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. 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.

18:55Drew Scott:I didn't want it to be Drew Scott or like my own name. Yeah, I knew right away. I wanted it to be more of a brand that I can like build something around an image and then people can like envision themselves investing in as well. You had the cooking blog for a little while. I had a cooking blog. I don't even cook. Like, I don't know why I had that. Your sales doubled between more than doubled, actually, between 2024 and 2025. 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? Honestly, it really was like the switch in my product collection.

19:34Drew Scott:Like it was before, like a lot of contemporary products or things that you can buy wholesale and then you resell. 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.

20:09He was selling video 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. I started playing video games very young, started selling video game characters when I was 12 years old. I 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 let's 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 to follow your passion I think there is a lot to that, especially nowadays when you can provide value in so many forms to so many different audiences.

21:09Even a humanities major that studies European history, you can go on to TikTok, do book reviews, visualize the book reviews, and still make money. That was not possible 10 years ago. And so all the mantra about don't follow your passion because it's not going to lead to economic opportunity, 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. The pandemic closed every door behind them. Carmen Dianne 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?

21:58I don't think anyone was surprised at the pivot. Maybe a mobile farmer's market. Like that's new. That's unexpected. But no one was surprised by the fact that I had some idea that I was following.