One of the main goals of managing a business is scaling your operations and securing a bigger revenue. Once you hit your desired numbers, you may think that things will become more comfortable and easier. However, many entrepreneurs find themselves facing bigger challenges as they acquire bigger financial wins. Gwen Bortner and Tonya Kubo break down why you are facing more pressures and problems as your revenue grows, and what you can do to keep up with the constant changes in your business. This is the time to answer that million-dollar question: “Why do I feel worse making more money?”

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Why More Revenue Is Making Your Business Feel Worse

More revenue is supposed to solve problems. Like, is that not the whole point of a business? The difference between a business and a hobby is whether you solve the problem or like whether you are making money or not making money. That is what we are working toward. We want more clients, we want more sales. Some of us want more growth, some of us are perfectly happy to maintain.

Why does it so often feel like the opposite happens? Why does the business start to feel tighter and more constricted, heavier, more complicated, when things are technically going really well? If you have ever looked at your numbers like I have been doing recently and thought, “Making more money here, why do we feel worse?” This episode is not just for you. It is going to give you a completely different way to understand what is actually happening because what we found and what I definitely know, working with Gwen, is that more revenue often does not fix what is off in your business.

Why Growth Often Feels Worse Instead Of Better

Instead, what it does is it reveals it. Gwen, I want to start with the obvious assumption. We talk about it a lot here, but again, it is like it is an off example or whatever. It is not something that we have actually really anchored an episode in, which is that the assumption is that something is not working. More revenue will always fix it, or at least give you the resources you need to fix it. It will give you flexibility, give you more margin, give you the capacity to hire more people, even. Why is it that so often the growth makes things feel worse instead of better?

The reason, of course, is a thousandfold. There can be all sorts of reasons why that is true. At some point, one of the reasons is that you need to bring other people on to support you because we all only have so many hours in a day. No matter how efficient, no matter how effective we are, there is the whole, “I do not trade time for money.” We are always trading time for money. We may be making really good use of that time.

People are not just magically sending money to you. It is for something and delivering that something, whether it is a physical product or a service or whatever, there is still some time that is associated with that. It may not be ongoing time. It may be only a tiny bit of ongoing time, but to prepare it took time. There are always issues around that. Of course, nothing ever works perfectly. Let us just be honest that we would love that if that was the case, but things break there, know things happen.

There is a point where we have to bring on people. That is one of the reasons. People cost money. People usually will not work for free, and they probably should not in your business for lots of other reasons. That is a whole different episode. That is one reason. The other is when we start getting more money, we also get freer in spending it. It is one of those things that when you are only making, let us say, $50,000 a year in your business, you get really conscientious about how much you are spending on various things.

When you have got $500,000 in your business, all of a sudden, instead, you are like, “This only costs $1,000. It is not that big of a deal.” Where $1,000 when you had $50,000 in your business was a much bigger deal. We start spending money more freely. Not that it’s necessarily wrong. We may be spending it on the right things. What was once a small amount becomes almost a non-existent amount, and what becomes a big amount becomes a small amount.

The things that were problematic when we were smaller actually still become problematic when we are bigger. It is just bigger numbers. If we are not being super aware and conscious of what we are doing, that becomes an issue. Of course, the third thing that we have talked about, but I do not think we have really focused on ever, is the difference between growing and scaling.

We have an episode on that.

I was going to say, I think it was quite some time ago, though. It will be one you will need to dig up and link to. Growing means that we’re making more, we’re getting bigger. Often, that means the costs and expenses and things that go along with it are also getting bigger. It does not necessarily mean that we’re making more money at the end, at the bottom line profit base, as opposed to scaling.

The other is that the problems we have at a $50,000 business are different from the problems we have at a $500,000 business. There are more people than I would love to mention who have gone from a $50,000 business to a $500,000 business to a $5 million business that says, “I would give anything to have the problems that I had when I was X size smaller.” That is for two reasons. One is a smaller business, smaller problems. The other is that they have now solved those problems.

Those feel like easy problems to solve. People often want to say, “It’s bigger business, bigger problems.” No. Part of it is that those are not problems you are having to solve anymore. You know how to solve those problems. You would love to have those problems because you know the answer. You know what to do. These are new problems. I do not know how to address them.

Got it. What I am hearing is that growth is more of an amplifier than a solution, especially growth when it comes to money, but I would say growth in people, too, but we’re talking about money in this episode.

Growth is more of an amplifier than a solution. Share on X

Generally is an amplifier. I think that’s a great statement.

You are inefficient. The inefficiencies that exist when you’re making $50,000 a year, like the fact that you like to be a little loosey goosey with whatever your available income is, are just going to scale when the revenue comes in. You’re still going to be loosey-goosey. If you’re doing mental bookkeeping at $50,000, you’re probably going to still be doing your mental bookkeeping at $100,000, but it is no longer going to work because it is a lot harder to keep $100,000 in your head than it is to keep $50,000.

To your point just now, in some cases, what you could tolerate at, say, 300k a year is like painful to the point of being a deal breaker at one million, just like some of the problems you have at one million that, the ones that you had at 300k that were deal breakers are like not even a blip on your radar at one million. The growth in and of itself does not create problems. It just makes those existing ones really hard to ignore.

Sometimes it will create new problems.

Especially hitting those additional thresholds like you were saying.

Certain thresholds will create new problems as well. If you do not really solve the problems, what you’re saying about amplifying, they just get amplified at the next level.

New Problems To Encounter When Going Up Revenue Thresholds

Let us actually briefly go down both roads. I have heard people say for years that $5 million a year businesses do not have the same problem as $1 million businesses, which do not have the same problems as $250,000 businesses. Maybe just briefly explain to us what the new problems are that you encounter as you go up in those revenue thresholds?

If we start at what I am going to call a lowest threshold, like just barely six figures or just under six figures, one of the statements that we have talked about before is that people say, “I do not really have systems. You always have systems.” What you do not have is consistent, documented, out-of-your-head systems.

Every business has systems. If you are falling short, what you do not have is consistent, documented, out-of-your-head systems. Share on X

Everything is still in your head.

You may or may not be consistent about it, depending on your personality type. It is probably not written down because it does not really need to be written down. You may be making a lot of on-the-fly judgments and choices about things because there is practically no issue with that. As you start moving into a 250 to 500k kind of range, that does not work anymore because it is actually adding so much complexity to your business that it’s slowing you down instead of making you faster. Even if you are still only you, even if you have not brought anybody else on, but you’re now paying a penalty, a mental and energy penalty for having to make those decisions and processes and think through them time and time again.

It is the tax switching, the context switching.

Yes. It is all of those things. Also, likely at that level, you have started bringing other people into your business as well, which means they are not in your head. Those things need to get out of your head. Sometimes they are out somewhat, but not completely. You still are a resource for a lot of the things that are going on. You are still the answer person for a lot of the things that are going on. As you start moving past the 500K toward the 1 million, 2 million, it depends on business models and all sorts of things. Generally, we’re looking at that real upper six-figure, early seven-figure stage.

Almost never, not never, but almost never, you are going to have to have people come in. They are going to need to start being able to make choices and decisions without you. This is often where the issue really starts showing up if you do not know how much you actually know and have not communicated it. You do not think that you are the bottleneck. You’re still the bottleneck because lots of things are still coming by you, through you, and around you.

At that point, you’re usually dealing with enough varied customers or clients that you cannot keep it all in your head anymore, and/or other people need to know the things that have been in your head historically, so that the customers are actually feeling the level of support that you sold them at that stage. What typically happens in that late six or early seven figures is there are fundamental changes that need to happen to your business model to be able to maintain that over time, and/or to grow it.

Usually, what is around there will be where you will absolutely get stuck if you are not making some fairly significant changes. As we move out of that two million and we start moving to the $5 to $10 million range, that’s when you have to have really serious structures in place. You have got to start thinking about being able to put layers in, which means you also need to potentially hire a few people who do not directly generate any revenue, which is a very painful thing.

That’s it, but I do not see how they’re directly affecting revenue. What they’re doing is making sure that you have time to do the things that you need to do. It is not this direct piece. All of a sudden, your overhead costs go up fairly drastically. Back to that usually means we’ve added quite a few people into the equation because our customers are bigger.

Depending on what our business model is, and it almost does not matter what it is, depending on what it is, we probably had to do some major overhauls of our infrastructure, whether it’s physical location, whether it’s our tech stack, there are quite a few changes that have probably had to go on in there. At that point, that’s the place where you’ll start seeing that you have a people problem because there’s too much individual knowledge that’s not shared enough in a way that’s accessible enough.

Even if you have got quite a few people and they’re all good people, I am not saying that you have got a bad people problem, but typically, if you have not been addressing it, there is not a good accountability structure, there is not a good communication structure, there are a lot of things that are missing at that level. Is that what you’re looking for?

Yeah. I think that’s really helpful because somebody who is tuning into an episode who clicks play on an episode called Why More Revenue is Making Your Business Feel Worse could be at any of those thresholds. It’s just really helpful to know something like, “This is normal.” If they see themselves in any of those problems, this is normal. I always feel like it’s nice to know, “This next level I hit, I’m going to get some problems there too, and this is what they’re likely going to be, so that I can either control them now or at least be prepared when they start to arise.”

The reality of it is, if it were easy, everyone would have $100 million businesses. If somehow it got easier along the way, then it would be like, “All you do is you get past this, and all of a sudden it’s magic, and everyone becomes this other thing. I’ve never seen it for anybody in any industry ever.

More Success Means More Pressure

What I hear most often, though, like going down the other path, is that the revenue is increasing. We had our best year ever. This was actually like a year ago, the best year ever. I paid myself the least I’ve ever done. I had to let people go, like this was not my story, but I had to let people go because profits feel so much thinner. The cash flow feels less predictable. That was definitely my 2025. Somehow, there’s more pressure on me as a business owner than I think there should be, given what my bookkeeping says I did last year. It’s so counterintuitive.

Part of it is that as the business gets bigger, you always have more mouths to feed. When I say mouths to feed, I am not necessarily saying employees or subcontractors. Part of the mouths to feed are the vendors that you are using to support your business. Part of the mouths to feed are the clients and customers that you have, who are creating the revenue. If you do not have more mouths to feed, that becomes a risk as well.

Let us just go down that because I think that is one that people lose track of. I have got three amazing clients, and I make $100,000 a year. Basically, we are getting $33,000 out of each client a year. That’s great. I doubled my business, but I still only have four clients. Now I am making $200,000 a year, but each client is now worth $50,000. Which feels good because it’s like, “My client value is so much better.” When one decides to no longer work with you, that is a much bigger hole to fill.

Even if it is like, “No, I am just increasing what my customer value is.” People will say, “That is the answer.” It is like,” Yeah, but no.” If we get too many eggs in one basket, if one egg breaks, it has a much bigger impact on everything else really fast. At the same point, if it is like, “I doubled my business, and I got five times as many clients,” that is a different problem. Not that it is back to, not that either one of these is good or bad or right or wrong, but there are different pressures depending on where that money is coming from. More mouths to feed.

 

 

Revenue Versus Profitability Versus Efficiency

Something else that you have talked about, because I do think that there are more mouths to feed, which I think speaks to revenue versus profitability versus efficiency. I am trying to think of, if you could maybe explain how you can actually be growing but becoming less efficient at the same time. You did a great job of explaining some of the risk factors that come with how we double our revenue and things like that. What I am talking about is going back to the idea of revealing the issues that are already there. I know for a fact that the clients I have often are not paying attention to the true profit of whatever they are selling.

The place where you start seeing, like you said, where it gets amplified, is if the revenue is increasing, is the profitable percentage staying the same? Is it going up or going down? We will just do simple math that I can do in my head. You have a $100,000 business, and you have a $10,000 in profit. That’s 10%. That’s a nice, easy number. That would mean if our profit percentage is staying the same, when we have a $200,000 business, we would have $20,000 in profit. Ten percent easy math. One of those things is we’re like, “We made $15,000 in profit this year when it was a $200,000 business.”

That feels like a big increase because it is. It’s a 50 % increase. We have actually reduced our percentage of profit, which means our expenses went up, not in a direct line percentage-wise. If we keep doing that, next year we may make $20,000, but we have a $400,000 business. We have gone from a 10% profit to a 5% profit in two years. By multiplying our business by two. We have 4x’d our business. We’ve only dropped our profit percentage. Often, we look at the hard number, and the number gets bigger. We are like, “We’ve won.”

This is a win. It is not enough of a win. That is actually telling us something about how the money is going out based on bringing in new clients. Sometimes what we discover, we were talking about this in an episode, if it was the last episode the one before that, but the cash flow becomes like a really big issue because when it’s a small number, it’s like, “I can suck it up personally to not get paid for five days because the cash flow is not quite there yet, but it is going to be there and I know it is going to land and I can handle it.

Until such a point, it’s like, “Wait, I am not able to pay myself, and I have got bills due, and it is going from 5 days to 15 days to 30 days to 60 days to 90 days. That is one of those things that will start amplifying because all of a sudden, “I am selling more, and I am fulfilling, but I am not getting paid until way too late in the process.” This can be traced back to part of the growth. When I was the one doing the fulfillment, I was also taking part in my pay from the profit temporarily. That was fine. I could do that for myself.

When I am actually hiring a subcontractor to do the work, because I no longer have enough hours to be able to serve as many clients as I am able to sell to, all of a sudden, it is like, “Wait, no, that subcontractor expects to be paid whether I have been paid or not.” That bill comes due whether or not I have been paid. All of a sudden, it is like, “Wait, the money is gone.” I am paying out money that I have not actually earned yet. That is one where all of a sudden it will amplify. At the smaller size, it does not show up.

As it starts getting bigger, all of a sudden, it is like, “Wait, that is going to be a problem.” Cash flow can be one. The first one I was talking about really is small expenses, but all of a sudden, when we get a little bit bigger, our email list gets bigger. We add one or two users to various accounts. Most of the time, that is not a linear thing. What ends up happening is it’s like, “You go from this price to this price.” You make this big jump. I cannot just add a user. Sometimes you can, but a lot of times it’s like you either have access to one user, you have access to five users, or you have access to fifteen users.

I actually only need one more user, but I have to pay for five. Now that may stabilize, but I have to grow to the point where that becomes okay. Are we using the best service that we need to be using based on who we are, what our size is? All of those things. There are lots of things that can get amplified in the process, but we have to be looking at whether we are comparing good numbers that actually compare. Say, “That’s why percentages often work really well, that we can see.” Good financial growth will show that growth goes up, and my expenses, percentage-wise, go down.

Good financial growth will show that growth goes up and expenses percentage-wise go down. Share on X

The Danger Of Getting More Comfortable With Bigger Revenue

Being aware that there may be a point where it does this big jump, because usually it is not this nice, little smooth line. Usually, all of a sudden, it’s like a boink, and it pops up. Being aware of these things and saying, “Is that actually a problem? Am I amplifying something that has been existing?” Or “Is this just a blip as part of the growth process?” Either of these things could be true. One of the things that I also see happen a lot as the revenue goes up is that we get comfortable that our revenue is up. Therefore, I should be able to fill in whatever blank you want.

Back to amplifying whatever.

If I am a business at this level, I should be doing this kind of thing as opposed to that kind of thing. This is one of those that was a long enough conversation. I cannot tell you if it came up in a podcast or it was just one of our conversations way back when, but where people are like, “I have got someone who is working really well for me, but they do not charge me enough. I need to go to somebody else who charges more. I am now a bigger business. There is no way that they could still be helping me.”

I need to be in a hundred-thousand-dollar program, not a $50,000 program.

It’s because there is no way that this could possibly be true. That might be true, but it may not be true. It could be like, “I just think I should be doing these things.” That amplifies the problem of what I am doing is I am trying to meet some expectation that is not necessarily based on any fact or reasoning behind it. It’s what I call a societal expectation.

That example aside, what I am hearing is that the pressure that they’re feeling financially is not so much because they need more revenue, which is why more revenue does not solve it. It’s because their business is not structured to support the level they are at or the level that they are on the cusp of. That realization is really important because it comes with waking up for me, it’s in the middle of the night.

 

 

When I cannot sleep, where you’re like, “At this level, this should feel better.” I like it, I should not have this angst. Should not be chewing on Tums or whatever else. Why do you think that feeling like, like even when it’s fleeting, maybe sometimes it just comes on the walk or on the drive or whatever, like this should feel better than it does. What do you feel like is actually happening at that moment?

It is often because we have assumed that when we hit that, it solves these kinds of problems. What’s happened is that you have grown, and the business has grown as you’ve gotten to that level, whatever that level is. What we do not realize is that it did solve those problems that you had back then, when you thought this level would solve those problems. Now the problems have taken on a slightly different flavor. We keep associating them with the problem that we had back then. It’s like, so it’s not actually the same problem.

It smells like the same problem, tastes like the same problem, feels like the same problem. It is not actually the same problem. It’s really a different problem. It’s a bigger problem. It’s a sideways problem. There are lots of other things that will go along with it. We get worried. Like, “It’s not solving that problem.” No, this actually is a different problem. I heard one of my mentors say this. Was on a completely different focus and topic. It was someone that I know. It was someone I knew when they were much earlier starting out, and where they were much later starting out. Her old thing was like, “I feel like I just cannot sell anything.”

I am not able to sell. Now, I happen to know that this person knows how to sell. The thing was, and I love what she said, it’s like, “You feel like this is the same problem it was when you were not able to put food on the table for the kids because you had just gotten divorced. It was a whole thing. This person is now selling million-dollar offers, I am not even exaggerating, and feeding the kids, so not in the issue anymore. This is not the problem, but she was associating it in her mind with the same problem back then because it feels like the same problem. Selling a million-dollar offer and selling a $5,000 offer are not the same problem.

What I am hearing is that this is where that misalignment becomes intolerable. What you were saying is, they’ve outgrown their current structure, it feels like the same problem in a different dress, but really it is, it is a different issue because the business is different.

When a business outgrows its current structure, they face the same problems in a different dress. Share on X

The business is different. The business model that she has now is so completely different from the business model that she had then. The sales process is a completely different process. She’s selling it to different, completely different people. I mean, like the list goes on and on and on, but it feels like I am not able to make this sale. That part is still true. I am struggling to make the sale. That part is actually the same, but all of the reasons why and whatnot are completely different.

Maybe it’s because it takes a little more time to sell a hundred-thousand-dollar offer than it does to sell a one-thousand-dollar offer.

There are all sorts of things. That is the thing is, we forget that where we are now, we actually are not dealing with those problems that we had before. We’re dealing with different problems. Even if they look like it’s just a different dress. It’s like, “No, it is actually a different problem.” The opposite side of that is solving problems that we do not yet have. I see that happen also. To me, it’s kind of the same version on the opposite side. I’ve had a couple of clients that we’ve talked to, it’s like, “You want to hire someone new, but you are not actually at capacity yet.

I know you do not want to feel like you have to hire under pressure, but we do not actually know when you’re going to be at or exceed capacity. If we’re really sure it was going to be in a week or two, yeah, you probably need to hire, but we do not know that. It could be three months, it could be six months, but it could be a year because there are some other things that we could be looking at that could be addressing this.” You know very well that I’ve been guilty of the same thing, and I am going to hire for where I think I am going to be, which we get a little too far ahead of ourselves. That is another reason that we can feel this pressure is that we’re actually trying to run the business of the future as opposed to the business that we have today.

Discussion Wrap-up And Closing Words

For the audience who is going, “Some of this actually does make sense. I am trying to solve the same problem over and over again. I am bringing in more money, and it’s just that it is never enough. It is not soothing the pain that I think it should be soothing.” You have our permission right now. Mine and Gwen’s both. I can get to speak for Gwen right now to stop trying to push through because it is not going to get any better. It is time to look at the problem differently. You have got to look somewhere else.

There has got to be a different place to look. If you are a normal human, thinking, breathing, walking about the world, and successful in your business, it is entirely possible that the answer does not lie inside your brain. If you knew the answer, you would have done it already. Quite honestly, you just would not. If you’re sitting there and you’re thinking, “We’re making more money, but something about this is not working the way that I think it should.”

Maybe your thought process is wrong, or maybe it’s an action item, but the only way to figure that out is to get some outside perspective. I highly recommend that you get that outside perspective from Gwen, because you just heard her tell you about 10 different, 15 different scenarios that might apply to you. There are like fifteen we did not have time to talk about. Go to www.tonyakubo.com/Clarity. You can book a 30-minute call with Gwen.

Do not have to go through me. Do not have to go through a support, assistant, or anything. It’s directly with Gwen, not a sales call, just a conversation. In that conversation, you’re going to be able to figure out if there is anything you’re overlooking. If there is not, we will validate that too. That’s my favorite part about talking to Gwen about anything in my business. She lets me know when I’m not on the wrong track, too. Go to www.tonyakubo.com/Clarity and book that call with Gwen.

 

Mentioned in This Episode

• Everyday Effectiveness Clarity Call
• Everyday Effectiveness on YouTube
• Thoughts on this episode? Email Tonya at Tonya@EverydayEffectiveness.com

 

About Your Hosts

Gwen Bortner has spent four decades advising executives and entrepreneurs in 45+ industries. She helps women succeed in business without sacrificing happiness by identifying their true desires and aligning their business functions. She spots overlooked bottlenecks and crafts efficient plans toward sustainable success that center your values and priorities. Known for her unique approach to problem-solving and accountability through the G.E.A.R.S. framework, Gwen empowers clients to achieve their definition of success without sacrificing what matters most.

Tonya Kubo is a marketing strategist and community builder who helps entrepreneurs build thriving online communities. As co-host of The Business You Really Want and Chief Marketing and Operations Officer (CMOO) at Everyday Effectiveness, she keeps conversations on track and ensures complex business concepts are accessible to everyone. A master facilitator with 18+ years of experience in online community building, Tonya takes a people-first approach to marketing and centers the human experience in all she does.