Business Owners Are Worst Clients

5/3/2026 at 4:18:51 PM

I was assigned to support sales people in a job long ago. I learned a lot about sales but it was enlightening to see their strategies for maximizing their reward to effort ratio.

A key strategy was to find someone in the company with decision making power or influence but who also was not really spending their own money/budget directly. You were wasting your time talking to anyone without power to make or influence decisions, but you didn’t want to go too high up the chain because the closer you got to the people who owned the business or the P/L of a division, the more questions they asked to make sure they were getting the best value.

So the optimal sales target was a middle manager who wanted an easy solution that felt like it would help their KPIs but who also didn’t really care if it was a good value as long as the number wasn’t so high that people started asking questions.

If you got pushed up to the business owner level you were going to get grilled on value and efficiency, so they would actually try to push down the chain to someone who didn’t feel like they were spending their own money. Middle managers will spend as much money as the business will let them to build their empires and hit those KPIs for the next raise. There is also a mentality that you need to spend a lot of money every quarter to avoid having your budget cut next quarter, which consultants are happy to help them do.

So it makes sense that any provider looking for the easiest clients wouldn’t want to go up to the business owner level.

by Aurornis

5/3/2026 at 5:37:10 PM

"show me the incentive and I'll tell you the outcome" or however that saying goes

by chermi

5/3/2026 at 7:50:17 PM

this is a pretty brilliant analysis that I've never heard before, and it definitely rings true to my experience as a freelancer

by mday27

5/4/2026 at 4:07:59 AM

I worked for a company that focused on top-down software sales, albeit to Fortune 500 companies. Align with the highest person you can in the organization, sell them and then support the engineers with high-touch support after the product was forced on them. It kind of worked.

by aworks

5/4/2026 at 1:32:01 PM

This is why capitalism created the most value and biggest pie for everyone- it is the only system with accountability.

by silexia

5/3/2026 at 3:27:48 PM

I wonder if there's an element of self-selection. The type of people to own a business could be more likely to put up a fight when things don't go their way (e.g. to protect the business and their investments), whereas the typical consumer is more likely to accept things as they are and not fight the business ("whatever, I'll just use another service").

by accrual

5/3/2026 at 3:33:46 PM

I think the selection may run the other way (or both ways). The population of small business owner-operators is disproportionately stocked with people who don't get along well with other people, who selected themselves out of having to deal with an organization of peers.

by jeffbee

5/3/2026 at 3:44:44 PM

How many small business owners do you know?

All the ones I have dealt with have survived precisely because of their ability to get along with people.

If you have no people skills your small business will fail.

by lelanthran

5/3/2026 at 3:58:27 PM

Maybe a better framing is “business owners are comfortable and accustomed to having conflicts in professional environments”

An employee doesn’t show up for work a few days in a row, you have to fire them the next day. Every day they’re pushing against the grain.

A vendor isn’t behaving? A business owner isn’t scared of using conflict to resolve the situation.

by cj

5/3/2026 at 4:05:18 PM

Yeah, the phrase “the buck stops here” is literally true with a business owner. Employees have the privilege to fantasize—the owner uniquely does not.

by justonceokay

5/3/2026 at 4:03:25 PM

I don’t know it’s a toss up for me. I would say anecdotally about 1/4 of business owners I know are community pillars and truly get along with most everyone. The other 3/4 are forced into business ownership because they struggle to take direction from anyone else.

In my experience contractors are the most likely to be friendly, and small retail the most likely to be unfriendly.

by justonceokay

5/3/2026 at 3:57:03 PM

I think they get along with people but don't like being told what to do, or be told "how things are".

by aaarrm

5/3/2026 at 8:39:19 PM

> If you have no people skills your small business will fail.

In fact a lot of them do fail, maybe not coincidence. Also, "people skills" in some cases means being a manipulative sociopath.

by throwaway81523

5/3/2026 at 3:38:43 PM

Damn this hits. My dream is a solo firm where I deal with nobody. I’ll never get there of course because the world runs on relationships.

by bix6

5/3/2026 at 3:46:58 PM

Businesses actually require even more relationships than standard wage slaves. Consultants need to be even more of a "people person." The main difference is that, for an owner, they "have no boss." (In quotes, because customers tend to be even more demanding "bosses," than managers).

My experience, from knowing quite a few business owners, is that they are always "angling for the edge." They want to squeeze every bit of advantage, out of every relationship/deal they have. Almost every relationship is adversarial and competitive. Lawyers can be the same way. The best ones, consider every interaction to be combat.

I'm not wired that way, so I'm not a particularly effective business owner.

by ChrisMarshallNY

5/3/2026 at 3:50:07 PM

A business owner has lots of bosses: basically every customer.

by trollbridge

5/3/2026 at 3:55:23 PM

That's true, but as business owner you can also fire your boss.

by vrganj

5/3/2026 at 4:29:41 PM

Employees can quit too.

In both scenarios, it really depends on how many alternative options for income you have available.

by awb

5/3/2026 at 6:33:18 PM

Sure, but as a business you're ideally already somewhat diversified in clients.

As employee, it's all or nothing.

by vrganj

5/3/2026 at 4:20:49 PM

Someone who doesn’t get along well with other people is going to have a difficult time operating a business beyond a simple 1-person shop.

Relationship management is everything in running a small business. You have to get along with clients, employees, suppliers, customers, and do a good job so all of them continue wanting to work with you.

by Aurornis

5/3/2026 at 4:26:51 PM

When you’re paying someone’s bill/salary, it changes the dynamic.

Just like someone in customer service might act differently with coworkers vs customers.

by awb

5/3/2026 at 3:58:30 PM

I think it's simpler than that. The business owner is spending their own money. When they feel (rightly or wrongly) that they are not getting what they paid for, they will feel ripped-off and angry.

The employee is spending someone else's money - they are more likely to be rational or even blasé about losses when it is not their money.

by santoshalper

5/3/2026 at 4:11:32 PM

I haven't seen much of business owners being ornery like the article describes, but there's other challenges:

Business owners (thinking SMBs) tend to have a holistic view of their entire business, to know what everything costs, how the numbers work out, etc., and to personally feel the risk. They also generally don't have a lot of time to invest in changes, and may not want to delegate too much. And they know that a lot of vendors are full of poo.

(Source: Our anti-counterfeiting slash supply chain integrity startup ended up working with major brands, but we also tried small businesses (e.g., designer who had their own production line of huge CNC machines in their studio). We tried tailoring solutions to some of these upscale small businesses, but in the end we only ended up getting money from large enterprise prestige brands. Enterprise sales, OTOH, is a painful and risky slog of numerous stakeholders, foot-dragging dependencies, opaque politics, changing priorities, etc.)

by neilv

5/3/2026 at 3:47:00 PM

One possible explanation: business owners have more skin in the game and care the most, so they are the most demanding and can’t tolerate waste. So they are the hardest to satisfy.

Additionally, they are not used to mincing their words because they don’t have bosses and are the most direct (and also egoistic).

by mikpanko

5/3/2026 at 4:54:23 PM

I’ve owned some trivially small businesses, and something I think is missing in the discussion is how quickly people’s presumptuous bullshit has me on the phone burning time-money. They think I’m rude, it’s them though, and their sloppy sales ‘lies’.

In those roles it’s not that I’m king whatever of wherever, but I know intimately how much my hours capitalize for, and given that lots of sales/customer communication is happening on the phone, you get a big impedance. Smug low tier sellers trying to talk past me, and flatly disrespecting me when trying to rationalize their pre-packaged pitch.

Architecture is customer facing. I am nice, and soft spoken the first time. But when kindness is misunderstood as ineptitude and people start talking to me like I’m a girl who could just never, like, understand a transmission…? My only regrets are not hanging up hard enough and refraining from swearing at them in the early years.

Other people’s C-tier employees and D-tier operations are not my problem unless and until they pay me.

by bonesss

5/3/2026 at 3:23:33 PM

I own a business and I go out of my way to respect other businesses, because I know how hard it is to own one.

by havaloc

5/3/2026 at 3:37:14 PM

Second that, Not only respect other businesses but when I am working for one I am aware that every penny they pay me is a negative for their company. So I make sure my work is done as quickly as possible and I don't "milk the clock".

In my experience the worst clients you can spot right away. They are the ones who are trying to get a discount. The work is always too much and it is never good enough. I filter clients by letting them know costs in advance. If they complain or suggest that it is cheaper down the road I politely suggest they find someone else. Otherwise...you end up doing 2x the work for half the price.

Also, if someone advises you should "Do the work at a discount and then it will be good advertising for your company". I suggest either walking away immediately or asking exactly what type of "advertising" they are actually going to be doing. From my experience these people give the worst reviews.

by Ccecil

5/3/2026 at 3:46:23 PM

Familiarity breeds contempt. If business owners are your target, you'll quickly see the negative patterns. But same can be said about any target audience/persona.

I'd be interested if the author ever focused their efforts on a broad consumer archetype. Or worked in retail like a grocery store.

Every segment has a type that will spoil the bunch of you let them.

by obsidianbases1

5/3/2026 at 5:02:35 PM

Lots of spot on comments here.

They have 35% relationship terminations over 15 years and are just now wondering why?

No way.

This is just a new spin on something they have already believed.

An interesting post would include exploratory data analysis and a discussion of how they came up with the categories they used for their final analysis.

by fn-mote

5/3/2026 at 4:57:16 PM

Business owners carry a lot more stress than salaried employees (generalization but directionally true). They also don't have a "boss" that can fire them. Those two things are likely the reason for a higher likelihood of bad behavior.

by karl11

5/3/2026 at 4:52:48 PM

This is kind of similar to what we are experiencing, but there is one important caveat: only business owners with no employees tend to be mean and borderline fraudulent. Not all but there is a tendency.

But that kind of makes sense to me. If a business has no employees, then either 1) it is not a real business, or 2) the owner is a jerk (unpleasant) and nobody wants to work with

In other words some people start the business because they are forced to start “business”. Because nobody will hire them or they lack “social intelligence” so they are never prompted.

But if a business has at least one employee, the owners are usually very nice to work with: professional and to the point.

by tlogan

5/3/2026 at 4:05:48 PM

I worked for a technology consultancy which had an unwritten policy that they would decline engagements where the primary point of contact (or champion) would end up being the owner of the client company.

by tanseydavid

5/3/2026 at 4:10:47 PM

Wise choice

Businesses are usually better than individuals.

But businesses owners themselves are a hit or miss

by raverbashing

5/3/2026 at 7:06:24 PM

A friend of mine worked for the airlines when he was young.

He said that airlines disservice customers all the time - delayed or cancelled flights, problems with luggage, everything.

He worked with most people just fine to get through things.

Except for one group of customers. First Class. If you disservice a first class customers, they get MAD.

My take is that the people paying the bills, their expectations might reach the size of the bills, and if the bills are large, so are the expectations.

by m463

5/3/2026 at 3:51:46 PM

My wife is a freelance digital marketing specialist, this post basically describes what she's been seeing since the start of her career 10 years ago.

As a tech guy, I've found that business owners tend to be way more pushy. Normally they fall in the boomer category, or they simply are not in the field.

Both categories seem to assume that "ahhh IT, things are instant and tomorrow I'll have 10'000 daily visitors", while that's very far from the case. They think that spending money today means results tomorrow as in "next sunrise", while digital marketing is basically subject to the whims of Google/Instagram/... and their algorithms, and investing today means seeing results at the very earliest after three months.

You tell them beforehand many times, they sign a contract, they agree with everything... and then after 2 weeks they start asking you daily why things are not improving, with zero respect for work hours or personal boundaries. That's how they choose someone else via "high-friction", and they normally land on bigger agencies because they think bigger agency = faster results.

by plqbfbv

5/3/2026 at 4:38:16 PM

When consulting, I've found the opposite to be true, but I've tended to work with smaller businesses, often as a solo developer on whatever project I'm on (my current employer, who I've been with for a long time, started as such). Then again, on every project, I've tried to understand the business and the role I play, understanding that the technology itself serves the business, not the other way around.

by bdcravens

5/3/2026 at 4:10:51 PM

I've had completely the opposite experience at Ritza, my dev rel agency, for the last 5 years.

My favourite is to work directly with owners, cofounders, etc. They know what they want, and they have the authority to approve stuff - it's really nice just focusing on the 'real' work instead of the admin and to know that the goals they set are likely valuable and not just someone trying to check a box somewhere.

by sixhobbits

5/4/2026 at 1:30:49 PM

I own a much larger agency than this guy and I don't understand his post at all. ALL of our customers in a marketing agency are business owners, though sometimes they may assign a point of contact.

Business owners hold us accountable and that is right and good.

by silexia

5/3/2026 at 4:42:36 PM

I see another explanation. A generous take would be that digital marketing agencies generate mixed results. But many would have far worse things to say about the ROI these agencies produce.

I don’t know anything about the author’s agency, but I can imagine that if I were a small business owner and I allocated budget to them, I’d absolutely let them know how I felt if they failed to produce results. This would not be the case if I were a salaried employee at a larger business responsible for outsourcing digital marketing. It just doesn’t matter to an employee in nearly the same way.

I’ve been a founder and I’ve been in sales most of my career, I’ve sold to enterprises as well as to small business owners. This isn’t to say the author isn’t right. I just disagree with a lot of the comments on here about the inherently misanthropic nature of small business owners.

by ashalhashim

5/3/2026 at 4:47:27 PM

> I’ve always been struck by a recurring trend: whenever a customer throws a tantrum, threatens legal recourse, or takes things to an extreme, they are almost invariably another business owner.

If a business owner threatens legal recourse, then, probably it's them. If multiple business owners threaten legal recourse, it's definitely something you're doing wrong. And that usually is along the lines of over-promising and under-delivering in an agency context.

by neya

5/3/2026 at 4:53:23 PM

Well yeah, in a B2B context, it's far easier to satisfy some random employee who's not actually paying the cost versus a business owner who is.

Also, if multiple business owners are threatening legal recourse against you instead of simply dropping you, you're probably the problem...

by dismalaf

5/3/2026 at 6:39:48 PM

> I did some manual verification on most of the data because this peaked my curiousity.

It's "piqued my curiosity".

by maest

5/3/2026 at 3:47:59 PM

Why is this a surprise? A business owner speaks his own money. A "non-business owner" means "an employee of another business" who doesn't care about anything but clocking out at 5pm and not getting fired - they are totally not interested in stirring trouble. It's just a metric of them not caring, not of them being "better clients". And representing bigger and richer entities than those where a business owner is a point of contact, meaning whatever money is/was at stake is usually not worthy of bothering.

Naturally, it is a lot better to work for richer entities with less control and attention over money spent, milk the fat cows.

by anovikov

5/3/2026 at 3:31:23 PM

Devil’s advocate: they’re more demanding because, unlike employees, they are not pushovers. They have skin in the game.

You seem to have equated “more likely to terminate with critical comments” to “worst.” Seems pretty reductive.

by eduction

5/3/2026 at 3:39:46 PM

For that matter—not seeing the source interactions or the prompts—I wonder the extent to which business owners see business relationships as negotiated rather than “picked from the shelf.”

When I’m dealing with small businesses, I tend to explain my frustrations long before I cancel, and offer them a chance to fix them. Whereas with an off-the-shelf product, there’s no point: I say “just cancel my subscription please and thank you.”

I could see that being coded as “confrontational,” but more often than not, I and the vendor fix what’s bothering us and continue with our mutually beneficial relationship.

Oftentimes, I’m not the only customer with that pain, and fixing it with me has the happy side effect of making their product or service more attractive to others too.

By the time I do leave for good, that process has failed, so it doesn’t surprise me that there will be residual reasons for leaving…

by alwa

5/3/2026 at 3:46:08 PM

Yeah, you’re the best kind of customer. And I’ve found that fixing those issues tends to make those customers into evangelists.

by ericd

5/3/2026 at 3:35:49 PM

They might be entitled people or sociopaths.

by theandrewbailey

5/3/2026 at 3:42:40 PM

Unlikely. The majority of businesses are bootstrapped with a loan.

Those that survive are often the result of an owner who had their hand on the wheel through some very desperate times, times which would have killed the business had they stopped micromanaging.

by lelanthran

5/3/2026 at 3:43:40 PM

Are those the only people who terminate business deals “with friction,” sociopaths?

Disagreements are normal and leaping to words like “worst” or “sociopath” because one occurs is not going to produce a sustainable business IMO.

by eduction

5/3/2026 at 3:20:14 PM

I'd like to see the prompts used here because Claude will simply reinforce whatever conclusion you already reached if your approach to prompting isn't neutral.

by jeffbee

5/3/2026 at 3:52:21 PM

Seconded, with nearly 200 out of 800 relations being terminated negatively, I am sure that this business owner must have some serious doubts and is trying to find patterns.

by tramov

5/3/2026 at 3:43:26 PM

"small business owner" imo lol

by ookblah

5/3/2026 at 4:22:40 PM

Fucking marketeers. STFU.

by nickburns

5/3/2026 at 3:43:39 PM

[flagged]

by throw848tjfj