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Tune in to this episode of BOSSY, the other podcast I host with entrepreneur Tara Reed, of Apps Without Code. This is a show we started at the end of 2023 to expand our surface area beyond just personal finance to entrepreneurship and career-focused conversations—you can hear new episodes every Thursday.

This episode is our conversation about pivoting out of business slumps—aka, you've been trying something for awhile and it's just...not working. What do you do? What are your options? How do you get unstuck?

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Our show is a production of Morning Brew and is produced by Henah Velez and Katie Gatti Tassin, with our audio engineering and sound design from Nick Torres. Devin Emery is our Chief Content Officer and additional fact checking comes from Kate Brandt.

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Katie:

Welcome back to The Money with Katie Show, Rich Humans, or should I say welcome perhaps for the first time to another show that I make called BOSSY.

This is a show that we started at the end of 2023 to expand our service area of content beyond just personal finance to entrepreneurship and more career focused conversations. I co-host it with Tara Reed, the founder of a multimillion dollar head tech company called Apps Without Code. The episodes you're about to hear is our conversation about pivoting out of business slumps, aka you've been trying something for a while and it's just not working. What do you do? What are your options? How do you get yourself unstuck?

You are getting BOSSY this week instead of a new episode of The Money with Katie Show because this year we're going to be doing something a little bit different. Now, if you're a longtime listener of the show, you know that we have produced a new episode every single week since October, 2021, and in the beginning of 2023, we added a second weekly episode in the form of Rich Girl Roundup.

This production schedule, while incredible started to buckle a little bit under the weight of our other projects, namely me writing a book, co-producing BOSSY, which is also a weekly show, and well, just wanting to have a little bit of free time to be a 29-year-old too, as the full-Time Money with Katie team is including me, only two people. And as I record this, it's a Saturday night, which is a habit I would like to get away from. I started to feel as though being spread thin meant the quality of the work was suffering, and that was inexcusable to me. I did not want to put anything out that felt like we were taking shortcuts to do it. So my goal this year in 2024 is to do just a little bit less but do all of it better. So starting this week, The Money with Katie Show will be three weeks on one week off.

So you'll get two episodes a week for three weeks in a row, and then we'll take one week off and sometimes on and off week we might drop an episode of BOSSY in if we think you'd find it interesting. But other times we might just go silent in your feed and you'll have a chance to integrate some of what we've been talking about or get caught up on episodes that you might've missed because as listeners have reminded me, it feels like a lot to me, but it can also feel like a lot to you too. I really appreciate your support of The Money with Katie Show, and I'm excited about the episodes we're going to be bringing you this year. Producing 80 episodes instead of a hundred, and will be tremendously helpful in keeping the quality of each one high. So without further ado, here's BOSSY.

They say women shouldn't be bossy.

Tara:

We're out here reclaiming that word. What's so wrong with being the boss? I'm Tara Reed, the CEO of a multimillion dollar ed tech business.

Katie:

And I'm Katie Gatti Tassin, better known as Money with Katie on the internet.

Tara:

At our core, we're driven by a shared ambition to build our own mini empires.

Katie:

Welcome to BOSSY.

The idea that if you're not growing, you are dying is like 90% bullshit and like 10% true.

Tara:

If you're not growing, you're dying. Okay, say more about that.

Katie:

Well, I think it can be hard to recognize when you're in a slump. I think it's something you just feel or you don't, but I do think that there is this constant pressure for the line to be going up into the right.

Tara:

Yeah, people think that if the business is not continuously growing than something something's got to be

Katie:

Wrong. I think it's more nuanced.

Tara:

Yeah, it's more nuanced, but I think it brings up a good conversation about just handling the slump overall because your business is not going to be up into the right. Life is not up into the right all the time, let alone business. And so how do you handle the slump? That's a good conversation topic.

Katie:

My favorite example of this comes from a guy named Nathan Berry, and actually, yeah, there's a lot of entrepreneurs in the audience who probably might not know him by name, but actually uses product. He built a newsletter platform called ConvertKit, and I was talking to him a couple months ago. He told me that his business originally stalled out at $2,000 per month in monthly reoccurring revenue while he was going for his goal. His goal at the time was $5K per month. He was like, oh my gosh, I really want to hit $5K per month, but I can't get past two. So he, he's in a bit of a slump for about a year, and then another founder is talking to him and he's like, bro, shit, or get off the pot, take this thing seriously or move on. Kind of insinuating $5k/month is not taken this seriously. You're thinking too small.

Tara:

Go for a bigger goal.

Katie:

So it inspired him to make a big bet. So this is where it's the decision in the slump. That's a little bit of a pivot. I'm going to take a big bet, I'm going to change my approach. He invests $50K of his own money into hiring more help, and he invested in a direct sales team. So we've talked about this before. You're hiring people that directly drive revenue within. This is so crazy. Within two years, remember he was stuck at $2k/month. Within two years they're doing $6 million a year.

Tara:

Dang, from $2k a month.

Katie:

And being like, God, I can't get to $5K. And then someone was like, dude. So he made that pivot, that really big ballsy decision.

Tara:

From whatever marketing strategy he was doing before to investing in sales team marketing team to really grow in a different way, not pivoting the product, but the approach and also the goals.

Katie:

Yes, exactly. That's a good distinction. He didn't pivot his product, he pivoted his business strategy around the product and said, I need to make a big bet on this. So he said the network effects kicked in around $15k per month where customers were then telling other customers about the product, and word of mouth started to be a piece of it too, but he needed the sales team to get him to the point that network effects could take hold.

Tara:

Interesting, because I imagine what he was doing before was a little bit more organic and then pivoted to direct sales. Direct sales is we are going to pick up the phone, maybe do something that's not scalable, but have a phone call with you to sell in whatever the product is and do something intentionally not scalable for a period of time, and then the sort of organic piece of it. This network marketing effects kick back in after that. But there's almost like this arc of organic maybe can get you a little bit, and then really pushing forward on more of a direct approach so that more of the organic can continue to spin.

Katie:

And I think that's the hard part is knowing sometimes the answer is just enduring longer. You just have to stay the course and good things are going to happen. There are other times where you are on a slow march to nowhere. So do you have any examples of that that come to mind for you?

Tara:

Yeah. So my first business was an art startup. We had this art matchmaking algorithm that pulled artwork from the internet and helped you find artwork and matched your artwork based on your taste. And I had been building that with a totally different vision than the company that I have now. And there was a transition period where I pivoted from running Collecto for full time to running Apps Without Code full time. It wasn't like an overnight switch, but really what happened was collective was stagnating a little bit. I think more than anything, my goals felt out of alignment because I had heard all of this stuff about what you're supposed to do with raising money and taking the VC track and going to these accelerators. And so I just kind of fell into that. I went to a tech accelerator, went through 500 Startups, and we had investors.

We had not a lot, but angel investors and also 500 Startups as investors. And during my experience at 500 Startups, I realized in that accelerator like, oh, this is not really the path that I want to be on in terms of growth at all costs kind of business structure. But the challenge is when you take on investors, they have sort of that expectation, and I was lucky to have friendly, nice investors, but at the same time, apps without code started taking off because I was blogging about my experience building Collecto on an app without coding, and people kept messaging me saying, Hey, can you show me how to make my own app? Yeah, Collecto's cool, but show me how to make my own thing. And I moonlighted for a long time. So I was working on one business during the day and in the evening and on the weekends working on Apps Without Code, and then I mustered up the courage to go into pivot time.

It was clearly time to switch. I remember for Apps Without Code, we had one month where I made $70K in that month and I was like, okay, there's something with way more momentum here. I need to follow that. And I had to call the angel investors that we had and say, Hey, I'm shutting this down. I'm pivoting. I'm moving to a new thing. I offered them all the ability to invest in what I was going to do next, and it just wasn't like if you invest in art or creativity or something like that just wasn't in their thesis and they passed and I moved on.

Katie:

Was there any pride or self-worth tied up in that change?

Tara:

Hell yeah. I said it didn't happen fast. I was struggling with it. It was a slow burn transition because first of all, I was like, everybody's going to know I failed. Yep. Everybody's going to know I failed. In reality, no one saws and one cared that way. No one care, no one cares, no one's even looking at you that close.

Katie:

People are way too worried about themselves.

Tara:

They're worried about themselves, not see if you failed or not. They're trying to see if they failed or not. So no one really cared or stressed about it. In fact, if anything they were like, oh, this new business idea is cool.

Katie:

Yeah. Oh, she's on her second business. How interesting. Oh

Tara:

Yeah, exactly, exactly.

Katie:

Serial entrepreneur. Yeah, two time founder. Yeah, yeah, yeah.

Tara:

See, there's

Katie:

Always that spin you can put on it. It's like, oh, no, I didn't fail.

Tara:

And I think I learned too that in a pivot after that, I learned that it's useful to just think about both sides of the narrative, right? There is a doom and gloom narrative of like, oh, I failed. There's also another one. And it kind of gave me some courage to think about the other one, the more positive one, some of the things that you just mentioned. I like that. So yeah, so I made a whole business pivot, not even an inside of one business from one strategy to another, but pivoted from one business to a whole another. I like that. Have you had any sort of big pivot changes or small pivot changes?

Katie:

Yeah, yeah, yeah. I think especially when I look back on this broader concept of enduring through something versus deciding that something's not working and you need to take more decisive action. I think in the beginning of building money with Katie, I had this promise that I made to myself that I was going to blog twice a week for a year. That was like, I need to just, it's the beginning of the year, you have to get the momentum going. So I was like, I need a defined period of time that I'm going to give myself to see if this works. And so it was 12 months of twice a week and by the time the 12 months was up, things were going great and it was monetized and everything was fine, but it gave me that framework. And so in that sense it's like enduring is all there is to do. You're not going to pivot because what are you pivoting from? You don't even know if the first thing you did is working yet. So I think that was the enduring moment.

Tara:

Got it. So in my example, I'm sort of talking about moving because part of enduring is pivoting when you need to, and part of enduring is just staying on exactly what you were doing before and your example, you're sort of saying you stayed with what you were doing before. You stuck with the consistency.

Katie:

But then there have been other times recently where things were not working. We had our foray into courses I think has been a little bit lackluster. Our YouTube presence was not really working in the way we wanted it to. So in both of those cases we said, you know what? Shelve it. We're going to come back to that later. It's not the most important thing right now. We don't have the momentum there. We need to make a pivot there. So in the meantime, we're going to stop devoting disproportionate resources to these things, put the resources where things are working and then reassess, basically come back.

Tara:

When you experience business slumps, do you get kind of sad and email? Is it a hard thing for you to go through or does it feel calm for you?

Katie:

It feels like failure to me. Yeah, it's a mental game to me, I think is keeping it fun, right? And having things that you can go back to that get you back in the game and give you the ego and the confidence again that you need. I think you need one of two things. You either need delusion, you are delulu that you have a good idea and you're too naive to know that it's a long shot or you need to be so confident and have so much ego around what you're doing that you're like, obviously this is going to work.

Tara:

I definitely use music to boost confidence for myself when I'm not feeling it. When I have a hard meeting coming up or I'm in a slump of dang, things are just consistently not working. I definitely have some Go-to songs that just pump me up. There is a song on Beyonce's Homecoming live record. It's like a remix. It's an in-between of the songs. It's called, I've Been On, have you heard this? Yeah. It's like a Chopped in Screwed. I been on it.

Katie:

It's autotune. It's her voice, but it's like it's…

Tara:

But it's like chopped down and screwed. It's almost like a dude's voice and she's essentially just saying over and over again, I've been on, I've been on, tell me who's going to take me off, and in the mirror, I kind of just bulk myself up. I am looking at myself and I just gas myself up and I'm ready for the meeting after that.

Katie:

Okay. Can I tell you mine? Yeah. Yeah.

Tara:

Is it Taylor Swift?

Katie:

No. You're not going to listen to Taylor's. We have to get pumped up.

Tara:

I don’t know.

Katie:

You got to go for something a little more aggressive. What? I like New Level by ASAP Ferg.

Tara:

I’m on a new level.

Katie:

Yeah, I'm on a new level. He goes that little in the beginning and then he barks and I'm like fist pumping. Yeah, you got exactly. You cannot do that. That's what you have to do when the song comes on. So it's a good way to, I also like to do pushups for that song, but that's neither here nor there. I feel like also the fashion for you is big.

Tara:

Definitely fashion, the clothing.

Katie:

You're like, how do I feel today?

Tara:

There's this video I love on YouTube of Rihanna accepting an award. It's like a fashion award, and she gets up to do her speech and she's talking about how life hasn't always been easy for her and how fashion is a defense mechanism for her in a lot of ways. And she has this line where she says, as a child, I remember thinking, you can beat me, but you can't beat my outfit. And the way she says it with just her swag and her accent, you can beat me, but you can't beat my outfit. That gives me that confidence too that I got an extra armor on, armor confidence and cool. That's about it. If something goes wrong during the day, I got this. I love that. Got something else.

Katie:

Okay, let's talk about pivots. Pivoting out of the slump, right? Making that bold, decisive action. Yeah, I can think of a couple good examples of this. One is, I think one's kind a funny, but I'm going to tell you the not very funny one first. So Sprint, you familiar with Sprint? Yes. Cell phone, right

Tara:

Yeah.

Katie:

So in 2005, they had 29 billion in losses, and they get this new CEO in the door. Now, I don't know if you remember how annoying cell phone plans used to be. They were so expensive and you had to buy each incremental thing. It would be like you're buying a text plan and a data plans too. Were ungodly expensive, and then you had a number of minutes. Remember the AT&T rollover minutes?

Tara:

I definitely had my dad kick me off the family phone plan. He's like, you just can't have it anymore. I was just going over.

Katie:

You just kept going over

Tara:

I kept going over my minutes and he was like, well, you just can't.

Katie:

I mean, I feel like someone listening to that today who was like 22 would be like, huh,

Tara:

You have limited texts.

Katie:

You have limited texts and calls.

Tara:

It sounds ridiculous.

Katie:

Actually, it does sound ridiculous because that space has evolved so quickly, but at the time, that was very normal. It was so complex. You always felt like you were getting gouged by these companies.

Tara:

Business perspective, limiting usage of a piece of technology is not wild. So that's normal, but it feels weird now.

Katie:

Yeah, I think it's stupid. I'm like, anyway, so Dan Hess enters a CEO, maybe, I don't know, and he comes in 2007. He introduces the Radical Simply Everything campaign. So he's a marketing guy. That's his background. Now, normally CEOs come from the finance background. Most CEOs were a controller or in accounting or finance. They understand the numbers because being a CEO in a public company is so much about not saying the wrong thing about your stock and having Wall Street or the SEC come down on you.

Tara:

So you need an accurate conservative thinker for that.

Katie:

It’s incredibly, incredibly hard, and someone very well versed in finance, this guy was a marketing guy who really cared about customer service. So I think he saw this space as being like, wait a second, why is this so complicated? And he introduces this plan that is basically you're paying a price and you get everything. It automatically just simplifies everything, cuts through all the noise, and they've turned it around. They reversed the shrinking of the company, which is so, so hard to do.

Tara:

Yeah, that is hard. It really is. It really is.

Katie:

Then they acquired Virgin, Virgin Mobile. They entered the prepaid market, I believe, with that Metro PCS, and that's a totally different demo that they're going after there, and then most recently have merged with T-Mobile. But I think that that's a great example of just being, it's almost that midwit meme where it's just fix the problem that everyone hates and then all the complicated shit's in the middle, and then it's just fix the problem that everyone hates. But you have to do the obvious solution and the Jedi solution are the same,

Tara:

But you have to do something really different to get out of the slump, is what you’re saying?

Katie:

Yes, radically change radical. Okay. This is the one that I just think is freaking hilarious. So you know how in recent years, health, food and wellness has become a very trendy topic. So it's like all these salad chains, all these businesses that are trying to promote how, yeah, it's like health conscious customers. Okay, well, Applebee's was trying to accommodate that trend. Yeah, that's exactly the face I thought you were going to make. That is literally the worst thing you can do if your customers know you and love you for the opposite. So Applebee's tries to get into this calorie conscious health food train. They're like, Hey, what if we got away from our core offering of degenerate comfort pasta and instead try this.

Tara:

Wait, stop, degenerate comfort pasta.

Katie:

You know that Alfredo is making you sick.

Tara:

That is exactly what Applebee's is.

Katie:

You get sick for days. You cannot think straight after you eat that Alfredo. I know it's true.

Tara:

You’re not wrong.

Katie:

So they try to please this tiny contingent of people who by the way, are not even eating at Applebee's. The people that are calorie conscious are not going to Applebee's every Friday and is trying to appeal to them, and then they're getting totally squeezed by fast casual. Because if you want something that's tasty and kind of healthy, you're going to go to Chipotle or Kava or a place like that. You're not going to go to Applebee's. So they go, you know what? Fuck it. We're going to lean back into the basics. They introduce something called Ribblets. Okay, so I'm like, little rib

Tara:

Sounds good.

Katie:

Exactly. They introduced, this was the big one, the Dollar-rita. Okay. This is like a drunk suburban mom sensation. It's a $1 margarita. The Dollar-rita.

Tara:

Delicious.

Katie:

Ever since 2020, they made this pivot back to like, no, we're going to stay true to who we are. Sales has been banging. Things have been great.

Tara:

Interesting. It's an interesting nuance.

Katie:

It’s like a reverse pivot.

Tara:

It’s a reverse pivot. And it's also an interesting nuance too, because it's like you can be doing one thing, pivot, and if the pivot doesn't go well, you just pivot back. Sometimes we think the pivot is permanent. That's a good point. It's not permanent. Applebee's is a really great example of take yourself back to the degenerate. Was it degenerate pasta?

Katie:

Degenerate comfort, pasta, de

Tara:

Pasta. Just go back. Go to de degenerate comfort pasta.

Katie:

Why get people like you? Yeah. Retreat, retreat,

Tara:

Retreat. Back to the

Katie:

Pasta, climb back into the garlic bread. Get cozy. Get cozy in there. Yeah. So I think that's a good point. It's that you got yourself into a slump maybe by trying to be something that you weren't, and if it's not going well because you're just like a knockoff version of the original, then go back, go back, go back. Nothing wrong with that.

Tara:

Yeah, this is good.

So I want to workshop this with you and for everyone who's listening to this and watching this. So I want to kind of do a little activity around when it's time to pivot versus stay the course. So I'm going to give you some potential slump scenarios and you guys can play along with us. If you go to YouTube in the comments, you can write your answer, you can play along with us so we can see what it is that you think should be done in each of these scenarios if you should pivot or you should say the course. Okay. Okay. Scenario one, by the way, if you're playing with us on YouTube, tell us what number scenario you're putting your answer for so it doesn't get all jumbled up. So scenario one, after a year in business, your revenue is stable but hasn't increased. You pivot, you stay the course.

Katie:

I'm going to say since you're just one year in, you stay the course. One year is still very, very early.

Tara:

Yeah. I would say the other side of that is one year or so early that it's, it's really easy to pivot when you're in. Once you get five years, in 10 years, it becomes harder and harder to make these big pivots. So I'm excited to see what everybody says on this if they would pivot or stay the course on this. Okay. Number two, scenario two, your marketing strategies are resulting in good engagement but not conversions. So let's say maybe it's like social media marketing you're posting, but not getting actual sales

Katie:

Pivot. I think you got to pivot because ostensibly, the point of marketing is to be moving the needle for the business. So I think you pivot.

Tara:

Ooh, that's a good one. A lot of people get caught up in like, oh, I'm doing marketing, but really maybe. Yeah,

Katie:

The awareness play.

Tara:

We don't have time for that.

Katie:

It's a startup. Unless you're really well, unless you got endless marketing budget, then. Okay.

Tara:

Yeah. Which most of us do not. Okay, got it. Scenario three, let's talk about ones that maybe you might see earlier on in your journey too. So you notice a gap in the market that your current business plan does not address, but could capitalize on. You pivot, you stay the course.

Katie:

I think pivot. If you are still early on, you're still trying to figure out what you should be doing and you see the opportunity, I think then it totally makes sense to pivot. I think if it's a shiny new toy distraction and you're like, oh, that could be something, but you already have something completely different and it's working, then I would say ignore it. Yeah.

Tara:

I also think a lot of times people can't get started in the first place. They keep pivoting their doggone business plan, and so I think that's a scenario where you have to look at yourself in the mirror and be like, I need to stay the course, because every day if you were finding a new thing you need to add to it, you just need to keep doing it and keep doing it and keep perfecting the business plan and oh, I found a new opportunity. Think also.

Katie:

Do you have a business plan?

Tara:

No, I don't have a business plan. Yeah. I think the business plan is like go on the internet, LinkedIn, social media, whatever, find people who are good potential customers. Send them a message and ask them to have a conversation with you if they would be interested in whatever it is that you got. That's the business plan, talking to customers in my opinion, but great. You're like, if you have a business plan, pivot, we're done. That's the scenario pivot. Okay. Got it. I'm curious to see what people say about this too. I do think there's a value in thinking through your plan to some extent. Okay. So we're kind of talking about making these different moves in order to grow the business, to pivot, to grow, to stay the course to grow. But is there anything wrong with just maintaining the business you get to a certain place? Can you just maintain it? Does it have to be the objective to grow?

Katie:

I don't think so. I think maintaining is fine. I think there are red flags though that you should look out for. So there's a couple that I think can signal that something is wrong. Now, just flat revenue is not necessarily a bad sign. That could be okay actually. But I think there are certain things that could signal you're entering a slump. We're already in one. So if any of these things resonate, I would say that is a sign. The first is lack of clear purpose, lack of clear goals beyond financial targets. A good way to test this is if you have teammates, if you were to ask everyone on the team what the purpose of the business is, are you going to get wildly different answers from everybody?

Tara:

Ooh, okay, got it.

Katie:

That's a sign. Another is waning enthusiasm. Are you excited about the future? I don't think this can be underscored enough. If you are not feeling enthusiastic about what's happening,

Tara:

Nobody is,

Katie:

Is no one's going to care more about it than you do. The third is disengagement from others. So in your organization, on your team, if you have teammates is the phrase, that's not my job. Running rampant people that have a very narrow view of what they're there to do, and if you ask them to step in to fill a gap, it's like, well, that's not my job.

Tara:

Or if you're a solo founder or a founder yourself, are you doing that? That's not my job is creeping in because in reality, so much of entrepreneurs rolling up your sleeves and doing stuff, that's not your job. And so if you're finding yourself resistant to do stuff, that's an indicator something needs to shift.

Katie:

And I think those are all kind of around mood, vibe, culture. Then there are some that are more about products. So lack of innovation. Is there any forward movement happening? Have you created something new recently? Or is the last time that you tried something new way in the rear view mirror that could be a sign that stagnation is happening, infrequent wins it hard to think of something that you would be celebrating. Is it hard to be like, oh gosh, I don't know. We really haven't had a win in a while. I don't know. That could be a bad sign. This one. I think you see it more in larger organizations, and it can be very frustrating, but I think when it starts to happen too early on a team, it's maybe a sign that something is going amiss it process kind of trumping curiosity. So if you've ever been in an org, that's really big. It's like, oh, well, we've always done it this way. Oh, well, this is just how we do this.

Tara:

Yes. When I worked at Microsoft, people said that all the time. Yes.

Katie:

It's like, oh, well, we've always done it that way. That is kind of a sign of complacency over being interested in finding novel solutions. And I think that that's hard to cultivate over time, but if you're seeing that, then I think it is a bit of a red flag. And then finally, just brand neglect. When is the last time that you clearly articulated the positioning, the messaging, the strategy? Are things feeling stale to you?

Tara:

Got it. And these are good signals to know if you are kind of getting stagnant and stale, and maybe it points out to you the places where your business and plan is getting stagnant and stale. So maybe you don't have to grow at all. Costs be growing like crazy. You do need some sort of forward movement to keep you excited, is what I'm hearing you say.

Katie:

Fresh energy. Fresh energy. So I think there's a good example of this with the Financial Diet. Chelsea Fagan, their founder, was on How I Built This last year with Guy Raz, and she told him, growth is not our goal. We are perfectly content with between $2-3 million a year. We have 10 or 12 employees. We're happy with that. But in the absence of a revenue growth goal, this is me speaking now, something has to keep people motivated to hit the targets. There has to be something that you're trying to achieve,

Tara:

Maybe an impact goal or something. Yes.

Katie:

And usually money is what people are trying to achieve. People are motivated by financial targets, but if you don't have financial targets, something else has to fill that gap. And she recently announced, I saw that they are revamping a lot of choices that they previously felt because they were playing it safe, and she's like, we need to inject some new life into the business. She, in so many words, was like, I'm kind of bored. We've been doing it the same way for so long. I'm bored. I've been doing this for 10 years. So

Tara:

She said, gross, not the goal, but we're kind of looking back at how that's impacted her. You're saying, and she's feeling bored.

Katie:

Yeah. I think it's sometimes the wanting to always be these things. It's correlations. It's that if you're always trying to make more money, it might be like, okay, well what other products can we launch? You're constantly trying to think of new ways to move the needle. And I think if you're like, oh, I'm happy with the money we're making, so we're just going to stay on the course we're on now, I think it's not about the money in either case, it's about the energy and the momentum that's behind and underneath those situations.

Tara:

This is also a really good example too. Sometimes we look at where a business is now, where a founder is now, and the founder is on a podcast saying like, oh, we don't want to grow. We're not really trying to do that. But you don't always get the full scope of how that decision turns out for them later. And so you take on that advice of like, oh, okay, I'm going to be like that. But you don't sort of see how then later on they've got to correct for that. That's a really interesting nuance. Okay. So I'm hearing you say there's nothing wrong with maintaining, but you need something moving forward. What about with quitting? We're talking about pivoting, but what about just pure quit?

Katie:

I feel like quit needs a rebrand a little bit.

Tara:

Okay.

Katie:

I think if you call, I'm like, when we call debt leverage, it's like, what if we just keep calling quitting, pivoting?

Tara:

Yeah. Interesting. This is good. My dad is retired now, but you can't say that he's retired. He will get very upset with you. He did not retire in his mind. He pivoted. He pivoted. He pivoted. That's

Katie:

Right.

Tara:

Yeah. Yeah. I think making the decision to quit slash pivot, pivot, quit, pivot. Pivot to qui is hard because you get these conflicting accounts from other companies. You hear about companies like Airbnb that struggled for a long time, maxed

Katie:

Out all the credit cards. In fact,

Tara:

Max took all the risk and then finally hit it. So you're just maybe holding on until you're finally hit it moment. And then on the other side, you hear about founders that are struggling for years. They let go of it, and the next thing is the thing that hits. And so it's kind of hard to make a decision about what to do when you hear all of these different accounts. And then on top of that, there is this concept of the fallacy of sunk costs because you feel like with sunk, you put all of this time into time, work, money, whatever it is, into a project. And you don't want to tell everybody that you're just starting everything new. Tell your friends and family or admit that you're failing. You feel like you put so much into it that you can't have that cost is that concept of sunk costs that you can't have the costs sunk.

Katie:

Yes. It's like if I give up now, then all those losses were for nothing.

Tara:

Yeah. The cost was sunk into the ocean and no. Yeah. So that's another thing that makes it hard to make the consideration. And then on top of that, you have this deep understanding. I know for me at least when I come up with new ideas, I know that my new ideas always seem way sexier than they are just because they're new.

Katie:

You've got some novelty.

Tara:

Yeah, I know myself enough to know it's like, oh, it'll be perfect everything. It's going to go perfectly. And I realize after doing this multiple times and adding on new things or trying new pivots, even if it goes well, it's not as perfect as it was in my head when I made the original plan. So when you're thinking about pivoting or stopping something, you're thinking about all of this in your head. There is a program that I did called Orbital Bootcamp. It was my first entry point into learning about entrepreneurship. And this was right when I was leaving Microsoft. I was doing this program. Is this the New York thing in New York? Exactly. It was in New York. And the syllabus for that program had a section because it was like a side project accelerator. The program was a side project accelerator. So they'll help you launch your side project.

And there was a section in the syllabus about end of life care, end of life care for startups. And there was this article in there by the CEO of Yipit called Wind to Throw in the Towel as a founder. And essentially what he's saying in the article is that you got to create a framework for yourself for when to know when to throw in the towel. One, you need a metric of success, pick one metric that you're trying to hit, and then you need to say, I'm going to give myself X number of iterations to hit that metric. So put a confined amount of time and a number of iterations on it. One, you have to iterate, you have to try some work at that. And those are mini pivots before you decide to pivot the whole thing to a whole new idea. And then once you've done that mini pivots, it's time to move. And it could be like NPS net promoter score is one of the best things for this seems like

Katie:

Brand affinity. How much do people,

Tara:

Yeah, it's that question you see on a survey, and it's like, on a scale of one to 10, how likely are you to recommend this service, this business to someone else? And likelihood to recommend is a good indicator of are you making something valuable? Yes. Right. So it doesn't have to be NPS though. It could be number of site visitors or revenue, but you have to create a metric and then give yourself a certain number of tries at it.

Katie:

I know that I made the joke about how we need to rebrand quitting as pivoting, but I actually think I want to loop that to connect it back to what you said in the beginning about both sides of the narrative, right? When you were switching from collector to apps without code, it was like, oh, one side of that coins like, oh, I failed. A collective failed. The other side of the coin is like, now I'm a two-time founder. Now I'm trying something different. This is so cool and new and exciting. Yeah. I think the narrative that you are telling yourself about the path that you're on is extremely, extremely important because it's all in the framing of how you're thinking about these things. And you can actively choose to skirt around the doom and gloom and focus on the idea that the benefits of what you're doing and how this is actually, no, no, no. This isn't me failing and quitting. This is me actually being a next level strategic thinker about the best path forward.

Tara:

A hundred percent. I think there's a lot of benefits to quitting. I just found this comic that was also in this syllabus. I just want to read it to you really quickly because I think it says what you're saying right now about the benefit of quitting. So it says, here's something true. One day you'll be dead. Here's something false. You'll only live once. So it explains what it means. So it takes about seven years to master something, and there's a chart with years on it. So if you live to be 88 after age 11, you have 11 opportunities to be great at something, right? 11 opportunities, timestamps. These are your lifetimes. You can think of them as many lifetimes. So most people never let themselves die to start the next lifetime. Those 11 pivots. And there's a little guy in the comic and he says, I've always just known I was good at organizing spreadsheets.

He's not letting himself move on to the next life. And it says, some are afraid of death. I only trained in one thing. What if I'm not doing it? Who am I? Instead of training into the next thing. Some think that they're already ghosts. I was good at basketball, but when I hurt my ankle, now I spend most of my time mentally thinking about what didn't happen, what I didn't get to have. They're sort of living in the past life, but you have many lives. And there's a little guy, he's like, in two years I'll die and I wonder what I'll get to do next. And so that's what this comic is about, about maybe we can link it for folks if they want to see it. I like that. But this idea that you've got these 11 opportunities to be great at something and to really pivot intentionally to try different things over the years,

Katie:

I love that. And it also makes me think about how I look at my career up until this point and all the different little mini lifetimes I've already had. I had a moment yesterday when I was sitting in the office here at Morning Brew in New York and kind of having fun with all the people here and being like, wow, it feels like a totally different me, a totally different life from Southwest and Meta and these other jobs I've had. It's funny how these become these little insular chapters almost.

Tara:

Yeah. I'm thinking about this a lot right now for myself because I'm thinking about this. I can feel myself in a transition period of being a lot of my brand and things I'm working on, being about tech entrepreneur to now I'm getting really interested in media and reality TV and these things and sort of this next iteration of myself that I'm on. And to your point about finding the narrative, I could say like, oh, I'm worried people are going to think I failed at something and just quit something. Or I could sort of look at the other side of the narrative and all the things that I'm excited about that new life stepping into.

Katie:

So if you are in a position as a listener right now where you feel like you're kind of on that precipice or you're afraid to make the transition, you're afraid to pivot. I feel like this is Tara and I saying, you have our blessing. You have that permission to make the pivot. That's what you need to do. And it's not. We're rebranding, quitting,

Tara:

Go do it.

Katie:

Go pivot. Go pivot. And if you enjoyed this conversation, we have tons of other fun entrepreneurial conversations on our channels. So if you like this one, go ahead and check out some past episodes and we drop a new one every single week.

So what'd you think? Did you like BOSSY? You can tell it's a different vibe from this show, which was the point, right? Trying something a little bit different. If you'd like to check out our other episodes of BOSSY, you can do so by searching BOSSY with Tara and Katie anywhere you find your podcasts. New episodes drop every Thursday, so you can catch tomorrow's Playbooks for Scaling Personal Brands to Millions, Celebrity Empires, and Emma Chamberlain's Evolution right here where you are listening to The Money With Katie Show and also on YouTube. And that's all for this week's non-episode of The Money With Katie Show, but have no fear. We will be back next week to talk about a multimillion dollar fraternity drug bust scandal with the investigative journalist who blew the story wide open.