Do bigger customers push back less on price than small ones?

It feels harder to go upmarket. It can actually be easier.

Why does upmarket work better than it looks?

Someone I work with raised the revenue bar in an event ad from $250,000 to $1 million. That higher number got him three legit business owners.

I see the same thing in my own sales. You talk to realtors and they say, "Oh man, I don't know about this." You talk to bigger businesses and they say, "You're only charging two grand? That's it?" One well-known entrepreneur told me I needed to charge at least a $10,000 setup fee.

What did insurance teach me about this?

The people who complain the most pay the least. When prices went up about 10%, here's what happened:

Customer	Price change	Reaction
One 20-year-old car, liability only	$400 to $440 (up $40)	Called in and complained like crazy
Husband and wife with three cars, a boat and a home	About $5,000, up $500	Didn't call

The bigger customer took more than twelve times the increase and never picked up the phone.

Does it apply to software too?

"these entrepreneurs, oh no, 100 bucks a month, are you crazy? And then you go to the big dogs and they're like, 500 bucks a month? Like, yeah, just make sure it works, you know?"

When you go upmarket and solve a big enough problem, you can succeed so much more. The bigger buyer mostly wants it to work.

Should I take small clients at all?

Early on, yes. I told a young Meta ads agency owner that the $500-a-month people are the worst. You have to be discerning about who you take, and you're not signing every mom and pop. But that's less true when you're small. Taking a bunch of small clients might be good for you, just so you learn.

How do I protect myself at low prices?

Make them commit. For anybody paying around $100 to $150 a month, I think you require quarterly payment. You've got to pay every quarter. Once the price is higher, that rule isn't necessary.

Who's easiest of all?

A surprising answer from consulting: well-funded non-profits. A lot of my consulting clients are non-profits or pseudo businesses, and they have the opposite problem from a small business owner. Their job is to find places to put money, not to squeeze a return out of every dollar. It's not their money.

That's frustrating sometimes, because they move slowly. It's also the opening. Most of the world runs on "someday I'll get around to it." If you just go fast and go after it, you stand out.

For how I weigh a few big customers against many small ones when choosing what to build, see how I decide which business idea to pursue. For who to target in the first place, see whether to sell to entrepreneurs or established businesses.