When to Quit Something That No Longer Works

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1:33There's no safe like SimpliSafe. Everyone knows Facebook and Instagram, right? Of course. But before Facebook and Instagram, or rather before their massive dominance, there were a lot of other companies out there. These companies that we may have totally forgotten about, but that were real substantial businesses at the time that were pioneers in this space. One of them was called My Yearbook. Do you remember My Yearbook? I don't, but there should be millions and millions of people who do. We reached millions of users and it led to two successful exits, a$100 million sale in 2011 and$500 million one in 2020.

2:17This is Catherine. Catherine Connolly. I'm the author of Designing Success, lessons from 20 years as a female tech entrepreneur. And the story of how she got here is really great because it starts so early, early for her and early for the industries that we would eventually come to think of as social media and dating apps. I started my yearbook with both brothers. My brother Dave and I were new in our high school. We were 15 and 16 at the time. And we actually created my yearbook as a way to make new friends, as probably the nerdiest way of creating a way of making friends. But a great one because also it turned out to be quite profitable.

2:51Yes, yes. And so my oldest brother, Jeff, he's about 12 years older than me. And so he started his first company when he was a student at Harvard. And so when we had our idea for the company, we pitched it to Jeff at the dinner table. He joined us. And this is in 2005. So they try to create this social network for high schoolers at roughly the same time as Facebook is trying to create a social network for college students. Facebook had a distinct advantage here, which is that college students have college email addresses. And that made it much easier to figure out who actually belonged. So we didn't have that same gating aspect that Facebook had.

3:30So we were like, OK, well, let's look at our data. We saw that people were just as likely to log in if they knew someone in their school versus if they didn't. So we're like, OK, so people are meeting people. It doesn't actually have anything to do with the school network. And so then we became about meeting new people. And we eventually just started kind of, you know, we had games, we had Hulu, we had so many things. I was just kind of throwing ways of meeting new people. And what ended up kind of focusing us was in 2010, we launched our mobile apps. So there was my yearbook mobile app, and that was a much smaller screen.

4:04So now we had to take, you know, the 20 navigation items that we had in our internet. Okay, what do these actually matter? What should we actually be investing in for the future of this company? And so a bunch of things were cut. So skip ahead. What this ends up evolving into is a collection of apps that are mostly dating apps. They're thought of as dating apps, although Catherine says they weren't exclusively dating, but they were basically dating apps with names like Meet Me and Scout. And it's under an umbrella called The Meat Group. And I wanted you to hear this story for two reasons. Number one, because it's just kind of fun.

4:40And it's fun to hear about the earlier days of this industry that now feels pretty locked into just a couple major players. But number two, because to do what Catherine and her brothers did, which is to say to evolve this company, required, as she just said a moment ago, killing off a lot of things, you know, building features into products and then saying, you know what, maybe not. Maybe this thing that we worked on that we thought was a good idea or maybe was a good idea for a while is not actually the thing that's going to bring us to the next phase of this business and then killing them. And that is something that every entrepreneur needs to think about and to get really good at.

5:24And it's why Catherine talks about it quite a lot in that new book that she wrote, Designing Success. My book is all about how to achieve genuine fulfillment and balance in a world where burnout has really become the norm. I'm really sharing strategies to help others design a life where they can thrive through different tools for setting boundaries, automating decisions, and fostering authentic connections. And that includes getting rid of the things that just don't work down to the feature level. Today on Problem Solvers, what we're going to do is dig into this moment in time for Catherine. When Catherine and her team were evolving their business and saying, you know, these things that we've built that took us here, these are not the things that we need to grow now.

6:11How do you know what those things are? And how do you make the hard decision to pull the plug, to make the big change, to stop doing something so that you can start doing something else? That is what's coming up today on Problem Solvers, right after the break. all right we're back today i'm talking with katherine connelly author of the new book designing success lessons from 20 years as a female tech entrepreneur and we're talking specifically about when to say goodbye to a feature something that you built that you loved that maybe consumers love maybe that they still love but that doesn't suit your needs now it's really hard.

6:52And I had asked Catherine to start by telling me about how she first started to confront this question as an entrepreneur. And she said, well, you know, it really goes back to that time when the company was going from being a desktop social media platform to going on mobile, because that was when the whole interface changed, there was less space, and therefore there was less room for all these features. And so she started to talk about some of the features that they had built back for the desktop version. And that's where we're going to pick up with her talking about the features that they had built before this shift to mobile.

7:33So like one of the features is battles, like a one-on-one image contest. And what was really cool about battles was like, it was one of the first major features we launched. And so there's like this kind of nostalgic value tied to it. And that's, I think, part of what was really hard about eventually killing a lot of the features that we killed in battles was one of them when we moved into mobile was, you know, it's not just like, oh, well, this isn't working. It's that it used to be working. And so recognizing, I think, that when something is no longer working, it is hard because there's a lot more like kindness tied into it.

8:06It's the same reason like you don't want to throw away like a t-shirt that might have holes in it, but you're like, oh, but I wore this on my first date, you know, something like that. And it's, you kind of get this connection to, to it, but to move on to the next stage, you have to realize, no, I need to get rid of it. I need to kill it so that we can fully focusing on something else. And so when it came to kind of that switch to mobile, we were like, we had a real focus on like, okay, what is, what is it that we're doing well? What is it that we can keep doing well? And that was, it was really meeting new people.

8:36It was like, and battles was a good feature for that, but it was kind of complicated and it just wasn't going to work well on the new device. Can I put this back to you because it's interesting. What you did there is that you shifted from asking a question about the feature to asking a question about the ultimate goal, which then allows you to think about how that feature fits into the ultimate goal, right? Like if you were to ask, is battles working? You could probably make a case that, yeah, it still works. People still enjoy it and so on. And it's hard to know when is something not working?

9:07What is the definition of not working? But if you say, you know, this isn't a conversation about battles. This isn't a conversation about this individual feature at all. What we really need to be asking is what are we trying to do here? And if we can have clarity of purpose there, then it makes all the decisions about everything else feel less complicated because you're not weighing your investment on an individual product. You're weighing your investment in the ultimate vision of your company. Am I right? Totally right. Yeah. So you basically need to figure out already what is your North Star and the items that are in your wheelhouse that are kind of leading there.

9:50And when it comes to, in the case of battles, it's just not there. To create it for mobile is something that isn't worth building when we could be building something else. And I think, I know you've talked about this before with others, but a lot of knowing what to quit is not just saying no to something, but it's being able to say yes to the thing that will matter for right now and to build. And so that's what we really needed to focus on. And we have this with a whole app as well. We used to also have this slide we used to present, like the app graveyard. And it's like basically all the apps that we have sunset that used to be in the portfolio.

10:29you um one of them was called unsaid we launched it in 2013 and what was interesting about that was it was when um when anonymous was super popular so like secret had just launched uh yik yak was um uh yeah anonymous you mean like like anonymous communication not uh the guy sitting in front of the screen with the v for vendetta mask communications where you can post things anonymously and they're all like networks up around that um so it was like very popular at the time we you know so we launched the same time as like all of those and it was doing reasonably well i think we had about 10 000 dau daily active users and yeah that's that's pretty good for like something that just just launched um doing a school by school strategy um but we decided to kill that because and it was it was doing well but we decided to kill because at the end like we were all of a sudden started seeing we opened it up kind of to everything because we had just been in schools.

11:26Then we opened it up. And what we saw was like, you know, some content that wasn't like awful, but it was something that, you know, we're glad we had a trust and safety team for. But then at the same time, you're seeing like awful news stories coming in from some of the other anonymous networks. There were, you know, more startups that like, you know, they had to make it work because that was the thing that they had. That was the central premise of their company. But we had another app, MeetMe, that was 100 times larger. And we didn't want to risk what we had built with MeetMe. And our goal there of building a network for meeting new people and having people find connections and find friends and find relationships and kind of ruin everything by having this other app that though could be promising and had promising growth, it could risk the whole other app by, you know, kind of diving into those waters.

12:23And so that's why we were like, okay, well, we're just going to kill inside here and focus back to our core app and our core message, which was, you know, meeting new people and doing that. You know, it's interesting because in some ways that example can be considered like a fringe case because how many people are launching something that also happens to align with a bunch of big attention getting very bad examples of how a product could go wrong. Like that's not often happening, but I wonder if you see a broader application for this insight and what that looks like, because what you have here is, it depends on how you look at it.

13:09Number one is maybe it's a product or feature that is having engagement, but not fully positive experiences for everybody. And so it's worth looking at, well, okay, people are using it, but are they getting what we want to get out of it, which is a separate question. And it's worth exploring that. The other is, is it creating market confusion or could it create market confusion for the other things that you do? So maybe even if it's not like a reputational risk, it's just like, okay, well, this is out in the marketplace. Is this going to shift people's understanding of what we are? And will that shift hurt our ability to market and sell the main thing that we do?

13:49Which is an interesting consideration. I wonder if that's something that you faced either with that product or with other products. Right. It's something that you're thinking about. It kind of takes us back to the same North Star element. What are you trying to build? Where do you want the whole company to go? And the amount of it, and I think what made it clear in the case of Unsaid, like the amount of work that would take to get Unsaid to a product that could make sense for our North Star, for meeting new people, for that connections, was going to be way more work that would really detract from what we should be spending time on.

14:24And so I think that's where, you know, where you realize that we had to quit it in order to focus on the things that actually mattered for our growth. And I think, you know, even from like the personal standpoint, like, I'm sure you've felt, I know you felt this too, where you're like, you just have so much things on your plate. And you have to start eventually looking at them. It's like, okay, well, you know, when you are, you know, many successful people, they don't like quitting. Like, it just doesn't feel good to quit. And a lot of the times, you know, there's sometimes like you can put like this like noble aspect to it.

15:00It's like, oh, I said I'm going to do something, so I'm going to do it. But just because you said you're going to do something doesn't mean you should do it. It means you need to, you know, re-ask yourself, is this still working for me? Is this still serving the purpose? Because like I said, with a lot of the features that we launched, you know, and it's over 18 years I was at that company. We're putting out new things. We're killing things all the time. And a lot of times, it's things that did well originally and things that just stop because maybe markets trends have changed and things like that.

15:30It's not just because something was out there doesn't mean you need to still keep working on it. It means that you might just need to have a new conversation. It's like, this isn't working anymore. Let's bring it back. And it's also about redefining what success is for any of your efforts, right? So if you define success for a feature as it's around forever, well, that's a pretty high bar. But if you define success as this feature helps us get to the next phase of this growth for the company, then it starts to look pretty different, right? I mean, maybe I even think about Battles, that feature that you were talking about a little bit ago.

16:08So Battles was a feature that worked in an earlier version of your company, and you could argue that what it did was it helped fuel growth at the desktop stage of this service. But now you're entering a mobile era, and Battles doesn't necessarily serve that or doesn't serve the next vision for the company. But that's not to say it didn't succeed. It succeeded quite well. It allowed you to grow. It allowed you to acquire users. Those users are now interested in the next generation of offerings that you had. And, you know, you can sort of Marie Kondo it and look at it and say, you know, thank you for your service, basically.

16:46And you can sunset it knowing that it did the job that it was created to do, which was not to be here forever. You weren't like Battles Incorporated to be battling into the 23rd century. Like, it was really just about making sure that you were providing people with the best experience based on the resources and the current needs of the users. What do you think? Yeah, definitely. Yeah. So we, you know, I would never have called Battles a failure because Battles was very successful for a while. And over the course of our company's growth, like we had, I would say, you know, basically like step function growth, like you would launch a feature and you'd see like this new level of growth and then you'd get basically a plateau and you'd get to the next level.

17:30You need to launch a new feature and you need that next or new aspect of a feature that would propel you to the next level. And so Battles did that. It's just, like you said, it had on the Marie Kondo side, it, you know, thank you for your service. We're just setting it now. Yeah, it's funny. It's almost like I just this metaphor just popped to mind, which is like, every product or feature that you produce is in some ways a rung on a ladder. And your job is not to stay standing on a rung of a ladder, your job is to continue to climb the ladder. And it would be pretty unreasonable and also quite dangerous if every time that you took your foot off of a rung to go further, that you also removed that rung and like stuck it in your pocket to try to keep it.

18:14Right? Like that doesn't work. That's, uh, that you're going to fall. So you have to, you have to, you stood on battles for a while and it was great, but it was a rung on a ladder and eventually it's time to take the foot off of it. Right. Exactly. Um, and so that's, you know obviously within the future standpoint like how quitting has just like made sense from you know for features to grow but also you know it does apply to like your personal life too and like how how you can approach different things so coming from dating of course um you know we would see how members would sometimes chat with people for like a really long time before meeting up in person and um you know that's that that that wastes time and so you know if you ask like for instance matchmaker maria like she was advised like you know meet up within three to five days and that should be your criteria for when to stop talking with someone.

19:03And so basically creating, and so that's coming, that's taking from Dr. Annie Dukes, you know, in Quit, she talks about having a kill criteria and knowing when to stop something. Because I think, you know, it's one thing to recognize, okay, this wasn't working, but it's another to like kind of at the get-go kind of start and say, okay, this is when I'm going to decide it's not working and kind of have that kind of tool so that when you're approaching, whether it's a new feature, whether it's something in your personal life going on a date. When should you say, okay, this is how much I'm willing to invest into my time and resources to this to see if it works.

19:36And then if it doesn't work, I move on. And I think that that's kind of the skill that we had to develop as we were creating features, as we were moving through building the company, because it's not enough to say in the retrospective, oh, we're moving to mobile. Let's see what we can get rid of. instead, you know, it became much more about anytime we're launching a feature. There's a lot of talking before. And I was like, OK, well, what was what are our goals for this feature? And, you know, what does it basically need to do for us? And at what point is it is it worthwhile? That kind of enters.

20:11And so then you're kind of going into being more proactive about how you're going to call things. That's really interesting. And you started to build that conversation, which I'm sure you didn't think about when you were 15. But eventually you started to build that conversation into the creation and launch of everything that you did. Basically, you're entering something by also assessing when it might come to an end. Exactly. It helps with the kind of the nostalgia value of like, oh, when is it not working anymore? If you already kind of have those decision rules in place for how you define it to yourself or how you define it for your company.

20:50And so that might be, okay, well, if, you know, the case of the business might be like, okay, if DAU and revenue aren't doing what you want them to do. But it could also just be like, okay, well, like I had a friend who he left his job. He wanted to try, you know, a startup idea. And him and his wife, they sat down, they set up a budget. They set up the amount of time that he would have to kind of play around. He did that. and, you know, kind of at the end of his, he was, you know, reaching the end of his, like, experimentation with him and he realized, you know what, I'm going to have to put a lot more resources than my family is comfortable putting into this, and basically putting into this test that it's just not right for us and realizing, you know, that that's, and then he, you know, joined something else.

21:35Because I think, you know, and so kind of going into that, he knew where to basically say, this is where I'm willing to, this is what I'm willing to risk. If you think about it, this is what I'm willing to bet. And you need to then know when to walk away. Yeah. Catherine, this was really great. I hate to, apropos of the subject, quit the conversation. But we're out of time. So tell us how to get this great book. So you can find Designing Success on Amazon and wherever you get your books. And you can also get it from my website, cconnelly.me. C Connelly, that is C with a C, not S-E-E or S-E-A. I got to think about that.

22:19C Connelly dot me. Yeah. Awesome. Catherine, thanks so much. Thank you.