[tptacek]

A lot of this is probably true, but it's really to your benefit to understand, as a businessperson, that this is generally how large clients expect to conduct business. You can fight it and even establish better payment terms, but it isn't always worth it. It's usually cheaper just to build a business that is resilient to late payments.

Over the last 15 years or so, a lot of my best customers have been super-late payers. You take the good with the bad.

[caro_douglos]

To double down on this it's worth finding out how the customer within the large company pays for things. Sometimes it was easier to get an annual or quarterly contract because that's how a company's accountants dealt with that employee/department's business expenses.

[subhobroto]

I used to think that offering a 10% discount on invoice to clients for payments within NET30 would motivate them to pay early, but very few clients, specially those complaining about expenses ever made good use of that.

Has this been your experience as well?

... and do you "outsource" your AR for a % of your invoices?

[tptacek]

I really don't think we even think about it that much. We have terms in our contract, and we send emails when payment is due, but it's not like we'd ever flip out if someone was late.

You can try setting late payment penalties, but my experience has been that client procurement and legal people get those stripped off routinely.

At Matasano, I remember one of our anchor customers taking something close to a year to pay an invoice.

[subhobroto]

> You can try setting late payment penalties, but my experience has been that client procurement and legal people get those stripped off routinely.

That at best. others just "forget" about the late payment penalties in my experience.

The sibling comment from @mrhappyunhappy is interesting but when I tried it, clients would rarely pay the premium.

[mrhappyunhappy]

As a consultant I state that I will charge a 10% late fee for every week a payment is late. I’ve never had a late payment. I’d say offering a discount does the exact opposite.

[subhobroto]

Clients past a certain size just "forget" about the late payment penalties in my experience, which is why I offer a "on time" payment discount.

I tried both methods and clients would rarely pay the premium compared to those who would avail of the "on time" payment discount.

I have less happier clients when I make them pay a fee than when I take away a discount although mathematically they are the same number.

[jjeaff]

That just gave me a flashback to my college accounting courses. So many examples where a discount was offered for on time payment. Must be a reason that technique has been around long enough to be a fixture in accounting textbooks.

[tixocloud]

From big co perspective, absolutely true. Tons of other priorities to get out of the door than paying on time. Our invoice process was dreadful. Thinking back, if a vendor made it easy for us, we might always pay on-time!

[tptacek]

How big is your average client and how heavily utilized are you? Your experience is very different from mine, but I may be working with larger companies (or you might be working with an idiosyncratic subset --- I don't think I am, though).

[mrhappyunhappy]

I work with companies 1-50mil in revenue typically. I don’t know what the law is when it comes to late fees, the language is mostly there as deterrent. That being said I am VERY picky about who I work with so I’ve never had a late payment or nonpayment, I suspect that’s more due to the screening process than the language in contract. If I ever had to actually charge a 10, 20 or 30% late fee, I would not pursue it and choke it up to a business loss and forget about it, move on. Cost of doing business.

[koolba]

I’m pretty sure that violates most State usury laws.

Note that I’m not referring to charging interest for late payment as being illegal. I’m specifically referring to charging 10% compounded weekly, which comes out about 14200% annualized.

[tptacek]

Probably not. Even in states that don't exclude fees unrelated to an actual loan of money, it looks like contracted late fees between businesses are excluded from usury definitions (that's the case in NY, for instance).

[newman8r]

I'm curious if there's any examples of this ever happening. Some company keeps ignoring a contractor's requests for a couple of years and ends up owing ~$20 million on a thousand dollar debt.

But like you, I'm pretty skeptical. Probably wouldn't hold up in court.

[TheOtherHobbes]

The outcome would be entirely random - dependent on the inclination of the judges.

A sensible business would settle out of court with a very low offer. A sensible contractor would accept the offer.

But generally this is another example of corporate privilege.

In reality, late payments kill many small businesses. In a political system that was genuinely friendly to the small guy, fines for late payment would be mandatory.

[koolba]

All my contracts that include such an interest clause also include language to the effect of “the lesser of X or the maximum allowed by law”.

[bitexploder]

We service Fortune 50 customers in a similar business to what Matasano did. This side of the business is definitely harder than the hacking / technical work. It can be tough to deal with and structuring bigger deals is important. Fast payment is not only important to not being at risk, but a short cash conversion cycle is basically more capital available at lower revenue. Kind of like velocity in the Agile dev world, only for money. There are diminishing returns (edit: in attempting to lower CCC) and large customers will throw you into the meet grinder that is their AP.

[MisterOctober]

No doubt about it. An effect of the behavior set I describe above [and I was only describing them -- I've been on both ends of that phone call over the years] is that in these relationships, the established payment terms are kind of irrelevant to the way things actually play out.

[subhobroto]

You are getting me really curious now.

I have tackled this issue (late payers) in two ways:

1. My cashflow from other investments ensure I did not run out of money. This is a bad design where I am effectively extending a 0% APR loan to the client with a term of their choosing

2. When I have ARs large enough to entice "parties that handle payments", I choose to let them handle the invoices on my behalf for a cut. A pretty large cut but 80% is better than 0%.

I am effectively looking for a way to optimize the later but happy to hear alternative solutions, specially when the ARs are not large enough to outsource.

For a bootstrapped business, this cashflow can be critical.

[tptacek]

I mean, if you're careful about who you work with, 0% isn't really a meaningful risk. Bank of America (or, for that matter, Airbnb) isn't going to default on you; the pain the ass you could generate if they did would cost more than the invoice.

[subhobroto]

Agreed with a caveat. Having actually worked with BofA, the amount of overhead for a contract could have put me out of business if I was not a BIG5 employee.

The big boys are not even going to consider me unless I am a safe choice (they really don't care if I am a kickass programmer who can solve their problems - they want to do business only if I am a known quantity so that they don't get fired if a deal with me go sideways).

I am really lucky to have positive cashflow because I can be picky about clients but a lot of friends ask me how to get started and my experience with cashflow is that a fantastic business with client set A can absolutely fail compared to the exact same business with client set B just because of cashflow issues.

Maybe I am too old and jaded but now I always ask people to include and test for cashflow in addition to the efficacy of their business ideas vis. market fit.

Honestly though, this becomes too demanding of entrepreneurs who are already overworked with lead gen, product design and development as is.

You should definitely write a few articles about cashflow. People don't write about it enough.

[tixocloud]

Entrepreneurs should absolutely be thinking about cash flow because it’s essential for survival. Demanding yes but necessary to become a successful startup.

Too many startups riding high on how much revenue they bring in without controlling the costs. If you spend to get revenue, it really isn’t a business (or at least a solid one anyway)

[kenneth]

You can always ask for a retainer, too.

[subhobroto]

Bingo. One of my favorite gotos. Any more ideas?

I size the prices with the retainers. Bigger the retainer, higher their priority and less the per project prices.

[kenneth]

You can get credit specifically to solve for that issue, usually at reasonable rates. Short-term small business loan facilities exist. Another decent option if you're reasonably sure you'll receive payment NET30 are credit cards + an online bill-pay service like Plastiq.

[subhobroto]

> receive payment NET30 are credit cards + an online bill-pay service like Plastiq

I personally have helped out a few businesses with a 2% CB CC (which helps offset the Plastiq fees) that offers a 6-mo 0% APR term but the CL is the limit of the loan which limits the extent of the loan.

Most CCs don't have such gracious terms in which case you could be paying a hefty fee to gain that cashflow.

Having done this a few times, my conclusion is that this is a very bad practise and exposes a business with cashflow issues if this is a regular occurence.

A healthy AR is better than no AR but you know what's even better?

A healthy cashflow.