Thinking about pivoting your business? Hold up.

In this episode of Unsexy Entrepreneur, Charles Harris (CPA & founder) and Dr. Seth Jenson (PhD in strategy) unpack the messy middle of entrepreneurship—when your idea isn’t quite working and you’re not sure whether to double down or ditch it.

From Noah Kagan’s taco-to-t-shirt pivot to accountants rebranding themselves as CFOs, this episode is packed with honest, nuanced takes on how to listen to the market without losing your soul.

💡 You’ll Learn:

• What a “pivot” actually means (hint: it’s not just changing your mind)
• The 3 pillars that determine if your business is viable: demand, channels, and margin
• Why chasing easy money often leads to shallow expertise
• The sunk-cost trap: why people stay too long in a dying business model
• How to spot real market signals vs. ego-driven decisions
• Why “following your passion” sometimes isn’t enough—and when it is
• How to test hypotheses like a strategist, not a floundering founder
• The ethics of positioning: should you call yourself a CFO if you’re not one?
• When a micro-pivot (like rebranding your role) makes sense—and when it doesn’t
• The niche goldmine example of a friend who pivoted into audits for lawyers (and crushed it)

This episode will help you clarify if your business needs a bold new direction, a subtle tweak, or just a little more time. Perfect for solo founders, consultants, creatives, and operators navigating the tension between vision and validation.

Got questions for Charles and Seth? Submit them HERE.

Welcome to the Unsexy Entrepreneurship podcast. I am your co-host, Charles Harris, and as always, I'm joined by Seth Jensen. And Seth, we're gonna have a fun topic today. We're gonna talk about pivots. Pivots in your business. And I wanna start off with a story from Noah Kagan. I kept calling him Noah Khan, who is a artist, which is very different than Noah Kagan.

⁓ A great artist. Yeah, we should have Noah Khan

in the background of all of our podcasts.

Hey, if he wants to join,

we'll totally be happy to have him on for a podcast. There's a lot of similarities between successful musicians and entrepreneurship. A lot of similarities there. But no, this is a story from Noah Kagan from his book, Million Dollar Weekend, that I'm assuming most people have heard or read or aware of at least. So in the story, he's talking about

It's true.

He's trying to sell tacos, street tacos to people and to his friends. And if I get some of the small points of the story wrong, you guys can correct me in the comments or, but I just, this stuck out to me quite a bit when, I was reading the book, but he messaged quite a few of his friends. He's like, this is how you start a business, right? You create a product and then you reach out to a bunch of people and try and sell that product.

Right. And so he reached out to, I don't know. I don't remember if it's 10 or 50 friends to try and sell his street tacos too. and lo and behold, not very many people were interested. but one person said, look, I'm not, don't want your street tacos. can just make tacos myself or, or buy them at another location. Like there are plenty of tacos around. but what I would like is your shirt. That's about tacos.

And so he kind of used that as the evidence, hey, like let's try and pivot. And so then he tried to sell his taco shirts to his friends and had a much better result. And that's kind of what I think of when I think of pivots. So I'm curious, Seth, is that a good example or am I totally off base?

⁓

You know, it's interesting. It can be, right? mean, that's the hard part is, you know, there's so many different paths to a successful business. And so it's hard to say, that was the good path or the bad path. But I think there is danger in talking about pivots. And I think they're overhyped in some cases and stigmatized in others. And so I'm glad that we're finally, you know, settling definitively, you know.

reclaiming the honor of pivots and putting them in their rightful place. Because here's the deal.

You can glorify pivots to the point where they're really misused. And this example could be example of that, right? Where if some entrepreneur's dream is to make a great taco business and they're like, well, I have to sell t-shirts instead. That could be the wrong move for them, right? And it could be like, well, I have to pivot because the market told me that, right? And I remember growing up, I had a finance degree, so I was surrounded by students all trying to start businesses.

in the business school and a lot of them were just chasing whatever they thought would sell. so they were just pivoting from crazy idea to crazy idea. have one friend who was doing supplements the other day and lumbar pillows the next day and just like lots of different things because they were just trying to find something that would sell. And the danger in that is you're never becoming an expert at anything.

So you're never actually discovering where value resides in your, for your customers. and that's a little bit facetious in the sense of, the example I just gave him, my friend, learned a lot. He learned about how to build an Amazon store and learn how to do manufacturing, but he wasn't developing expertise about a specific customer base or a specific product that would pay dividends forever for him. Right. Maybe he would randomly land on something that would sell. but once he was sick of that business, he wouldn't have really internalized.

deeply a particular opportunity such that he could continue to develop that opportunity. So if you're just pivoting and chasing an easy buck, in my version of entrepreneurship, that's a pretty ineffective way to do it. Now on the other end of the spectrum, there's people that feel like pivoting is giving up on their business. And so they're just dying on this taco train. like, my tacos will taste like this and they will look like this and it's the right way. And they're just slowly

Like they're building a business that only works for them and a pivot would save them and give them a lifeline they're not willing to take. So there's two ends of the spectrum. It's been lionized to the point where it's misused. It's been stigmatized to the point where people think it's failure. The sweet spots are there in the middle where remember you are the product in a sense. Like your expertise is as important as any individual step along the journey. And so use pivots.

to learn the right lessons, to approach an ever strengthening value proposition such that you land on something that you're excited about, you're expert in, and that your customers are just absolutely desperate to get their hands on. So that was a long answer to your question, but the answer is it depends. It depends very, very strongly.

You

Yeah. How do you know when it's the right time to pivot then? Is there right time?

Yeah. So think about pivots as in relationship to these hypotheses we keep bringing up, right? So in your early process, you're testing hypotheses about your value proposition. So in his case, his proposition was people want street tacos. They want them a certain way. Now, if he had broken that down into sub assumptions, like, all right, people want, deliver street tacos and they want fresh flavors that are vegetable heavy. Let's say that was kind of his

his value proposition and those were kind of the sub-hypotheses to it. If he's trying in these early days and he's trying to sell these products and these people and he's realizing actually delivery means they're always like gross and soggy by the time they get to them. So that's actually not what I want. And everyone says they hate it. Well, that's an opportunity to pivot. He either needs to change the delivery process or, you know, change away from delivery as a key assumption in his value proposition altogether, right? And so,

Pivoting is just looking at the data, looking at the hypotheses, finding out which ones are right and which ones are wrong, and adjusting accordingly. And sometimes you find an earth-shattering truth about your business and you're like, turns out people hate tacos. I'm the only person on earth that loved tacos. I don't think this is true. But he might realize that, that like, you know, I thought that, you know, vegetable heavy tacos were gonna be the next big thing. And literally even the hippiest people in Portland don't want my vegetable tacos.

You

People only want steak tacos. And you might eventually get that point where you're like, fundamental hypothesis was just wrong. Like most of my assumptions were wrong. And you have to make a major pivot and that's okay. Other times it's just making minor pivots where it's like, okay, hypothesis A, B and C were right. People like the delivery. People like the vegetable heavy. It turns out they just, my packaging sucks and people want them, you know, just.

They don't want fancy packaging. want them wrapped in tin foil because it feels more authentic. Maybe. And so it's just a minor pivot and you're now wrapping them in tin foil instead of spending money on fancy packaging. So pivots mean so many different things. They're a tool, not an ideology. And they can be big if your whole value proposition needs reworking, or they can be small where just a little tiny assumption in there needs to be adjusted.

Okay, so this brings up a really interesting question. If you're on LinkedIn or aware of the accounting industry at all, you know every single person is advertising themselves as a CFO. And this grinds my gears to no end. yeah, and not saying that they're bad people. I have many friends that are claiming they're CFOs.

Yeah. I know so many of these people.

they are. They're bad people. Just kidding.

But I can't stand it because at least for the majority of my clients, they don't need a CFO. And they maybe don't realize it, right? They might see CFO and think that this is really important and they need it. But I've worked around enough CFOs to know that CFOs are working on

long-term financial situations, right? So they're working on huge funding rounds or changing the fundamental financial situation of a business. That is not what the majority of these accountants are doing. And they're advertising themselves as a CFO, right? And I have been told many times that I should pivot to be a CFO. I just can't stand it though. I just, can't.

Yeah.

Ha ha.

I just ethically don't feel right calling myself a CFO, right? So if people ask me about it, usually I say I'm a fractional controller. That's kind of the level I'm at. I'll do a year forecast or I'll look backwards, right? And that's kind of more of where I consider myself. Not saying that, again, not saying that being a CFO is bad or inherently that these people are bad or anything like that. But I'm curious on your perspective, because I think...

If I was to pivot myself as a CFO, I would maybe make more money. ⁓ am I doing this incorrectly by not pivoting?

Mm-hmm.

It's interesting this example, because I remember in those early days, one of your main hypotheses were having these recorded kind of videos, like almost like a CFO debrief, at least what's going to they're going to perceive as a CFO debrief. And, and I think you realize that that wasn't as valuable to your clients as you thought it was going to be. Right. And so you kind of the printed PDFs, I think is where you ⁓ kind of.

Yeah, no, it's exactly what that is. Yeah.

adjusted more. I love that story because it's a perfect example of a pivot. And now it's funny because now the market is trying to like be like, hey, you know, do this thing that that in your opinion doesn't provide value, but looks good from a marketing angle in some senses, right? ⁓ Yeah, so it's it's tricky, right? And the thing is, it really comes, my guess is there's a certain level of client

Yeah.

Yeah.

at the premium level. And again, I don't know your industry, it's so you would know this much better. But where they want to pay a premium so that they can attach the CFO label to their firm in some situation. I think most of your clients aren't looking for premiums like that. Your current clients are more like, hey, I want a

Probably middle.

great accounting work done for me. And they're not the discount clients where they're like, I'm going to Turbo Tech. They're paying for skilled, careful accounting being taken care of, but they're not running with the cohort that's like, you don't have a CFO, how can you pay for your lake house? And so I think it's more of a question of who...

Right.

And maybe that's part of it, right?

who do you want your customer base to be and do they value that or not, right? ⁓ Because you might be sending a negative signal to your current base by attaching that CFO moniker, because they're like, ⁓ he must, he's too big for his britches, he's asking for more money, these different things. Whereas if you're like, you know what, I only want high net worth individuals or $100 million businesses,

Interesting.

in that case, then maybe you would. So in my head, you've got specific hypotheses testing to do, right, where it's like, okay, from my client base, does this moniker help or hurt? And from your lived experience, my guess is it doesn't help with your current clientele because you basically tested that in the early days yourself and you pivoted away from more of that.

Right. That's probably what's going on. Yeah.

Yeah, I mean there was a

client I had this discussion with maybe two or three weeks ago. They were a potential client. were looking at a few different accountants. And they asked me, they were like, well this one says they're a CFO. And you know, I went through exactly what I told you. I'm like, are they giving you CFO services, right? Or are they just attaching a higher monetary value? And maybe I'm losing out on money from not doing it. ⁓ I probably am.

but it's always interesting to, to me it's a pivot I'm not willing to make personally. And it's kind of an interesting, it would be a small pivot in the accounting.

Yeah. I mean, this sounds like a

classic example to me of

technical expertise, bumping up against client expectations that they don't know what they're asking for when they ask for CFO, right? Like if you ask your clients, well, what does a CFO mean to you? Probably they're gonna list things you do for them, right? ⁓ And so that's the cautionary tale I'd give you of if CFO means to them all the things you're doing already, then say yes. You know, yes, I do.

Right, no, that's exactly what it is.

Yeah, and that's exactly right.

This is what I do for you, whatever. And then, you know, it doesn't hurt to, and then you can say, because, but I don't charge more than the competitors because, you know, for these different reasons. And you can use that as a differentiator. So that's the only caution. In your specific circumstance, I would just be sensitive to the disparity between what your customers think.

Yeah, Noah, and that's great advice. And I fully realize, like, I'm probably

losing money by not saying, yeah, I'm a CFO everywhere I go. It's more of a personal thing for sure.

Mm-hmm. Yeah.

But you're

absolutely right. mean, CFOs, a firm has to be a certain size for it to make sense for them to have a full-time CFO or even a fractional CFO, right? And it usually has to do with long-term financing. Can you decrease the financing, the interest burden by this much? Can you go work deals with other companies such that we can, it's big long-term modeling.

Yeah.

And if you're just a nice cash flowing business doing a million dollars a year, there's almost no reason that you would need even a fractional CFO. But a good accountant, you will need.

You don't need it. Yeah.

Yes,

yes. So that would be, I would consider a very, very small pivot, right? Just adding that title to my name. A large pivot I saw recently, which is super cool. This is a friend of mine, she's running an awesome business. She basically does the exact same, or she did the exact same thing I do. But she pivoted to only work with

accounting audits which is super super niche specifically for lawyers right so their lawyers have to keep special trust accounts and then they get audited by the state bar more regularly than than average person and so that was you know going to a CFO title I think would be a pretty small pivot for myself but what she did was a huge pivot

Yeah.

Yeah.

from your perspective, is that generally a good move? Like in her case, I think it's worked out fantastic because she's so niched, no one else really does it. And so if I have a client that has an issue, I call her, right? I mean, that's exactly what I do.

Yeah, yeah.

So I love that example. And the reality is these types of opportunities are often lurking nearby all the time, right? And so it sounds like in her situation, she was going down a particular path that was working for her, but then she just noticed, hey, if I just get in this lane instead of this lane.

My clients will come easier. I'm able to charge more and it's less work for me. That sounds like an amazing pivot to me, right? And so especially if it's still in her wheelhouse, then I think that's a no brainer. There's this. You know.

And again, it's still in her sweet spot, right? Like she is an accountant. She might've been doing a few of those clients. My guess is how this happened is she started doing these clients and realized, I like these clients better. This is more fun for me and making more money, right? And so she's just going where the demand is, where the margins are. And so absolutely follow good margins, follow demand and don't be afraid to...

And I always give the most horrific metaphors, but kill the ugly child and feed the pretty one more. It's so bad. It's so bad. But businesses, we talk about businesses being our children, but they're not. They're not actually our children. But but. But because they feel like our children. Letting them starve to death feels so wrong.

That is awful.

It's like I've spent five years building this certain clientele base and now I'm realizing the honeymoon period's over, they're nickel and diming me, I don't like this type of work. But because I sunk five years into it, I don't want to pivot. And you don't want to do that. You want to follow, your...

what the expertise, what the data is actually telling you. And for her, it seems like it was kind of a beautiful transition and she was willing to make that leap. And it doesn't sound like it was a huge leap for her either. listen, right? Learn. Don't shut your eyes to the data just because you have a bunch of sunk costs in a particular area. But, you know, leap, look before you leap, right? She could have...

Another scenario could have played out like this, where she's talking to a bunch of clients or her ⁓ competitors and they're like, yeah, like we only do trust people and it's so much easier. And if she just leaped into that without looking and without trying some of that clients and finding her own data, she might realize, okay, this isn't as pretty as they make it sound. I don't enjoy the work as much and the margins aren't near as good as I thought they were going to be right. And so don't just follow the herd or make a blind pivot. Follow the data. Follow.

follow what your expertise is telling you. And when it tells you that it's time, that there's a better opportunity, yeah, be willing to leave away, know, drop the sunk costs essentially of what you've been working on.

Yeah, are there any reasons that you say that you should pivot? Like red flags saying I have to move now, I need to find something different.

Yeah, there's definitely, we've kind of touched on some of already, but sometimes the demand is not there for what you're doing, right? Sometimes you're like, man, I love this, but nobody else seems to, I'm like, I am the weird person here and I can't find my community niche that wants it. But even there, there's a cautionary tale to be had here because the question is, you becoming an expert on a con-

Right.

on a customer base or on a product. And it varies for some people. For some people, the passion is a specific product category where they're like, okay, this product didn't work, but there's something like it that I'm gonna make work.

For other people, they just love a particular customer base and are like, I love building things in the world of D and D and it turns out my first product didn't stick, but there's this other totally different product that my D and D community loves. So, so think about yourself kind of along those lines and there's kind of a gray area because the community and the customer are sorry, the customer and the product are obviously linked. but

You're becoming an expert in something and you don't want that expertise to go to waste. so, so anyway, that's the say, but sometimes there's not demand for the product that you're looking for. And that's, that's, you've got to find things that have easy and obsessed customers. Sometimes you're realizing your channels aren't working. And so you've got to pivot to channels that are going to be better or choose different products that suit the panels you have, the channels you have access to.

Sometimes the margins aren't as good as you think and you have to pursue products that are going to have healthy margins because it's always going to be more expensive. As you scale, costs are going to go up just as quickly as they go down with economies of scale. So you've got to be prepared to have healthy margins. Those are just the fundamentals of a good business. You need demand, you need channels and you need margins. Those three things, if any of them aren't working,

some pivoting is going to be necessary because those are the pillars of your healthy business. legs of the stool, if you will. There can be other reasons to pivot. You can just hate your life. Maybe those three things are looking really good. You've got to man whatever. You're like, I'm miserable. I hate this. That's a good reason to pivot. ⁓

Yeah, there

are a lot of accountants like that. They always end up as like ghost writers on LinkedIn for accountants or marketing for accountants. Buy an accountant is what they always say. But yeah, it's really common.

Yeah.

Yeah.

And then, you know, there's maybe the example of your friend where she had a good business, but there was just a better one just next door. And that's a good reason to pivot as well. Well, maybe she had margins, maybe she had demand, maybe she had great channels, but hey, there's one with even better margins and better demand and better channels. So that's a perfectly good reason to pivot. But at its simplest...

at its fundamentals, and this is where we all started on this conversation, a pivot is when your hypothesis is proving wrong. If you're wrong, pivot, try a different hypothesis. Try a different tack. And usually that has to do with the demand equation early in the process. listen, learn, hone your expertise. You are the product.

Yeah, I feel like business always comes back to that, right? Just improving the product and then make sure to deliver it and then keep moving and changing. I mean, it goes back to Lean Startup Method and everything else we've already talked about, so.

Yeah, absolutely.

Awesome. Thanks, y'all, listening to the Unsexy Entrepreneurship podcast. We'll talk to you next week.