A startup I know was basically killed by this (COVID was the main cause, but this was a large straw that absorbed a ton of time just before the pandemic).
Over a month was spent caving to every inane request of this one customer and the only reason they did it was because the customer was willing to pay $250 and they were the first non-institutional paying customer so they were obsessed with getting it right.
5 figure a month contracts that were soon to start but paused due to the pandemic went unserviced so that large parts of the product could be rewritten to serve this one person as though they were the expert on what non institutional customers wanted. And in the end they wanted nothing more than a custom Craigslist type of ad, just with their own custom style and everything.
Could have spent that month protecting the large contracts.
Ouch! That must have hurt. I totally get that when someone has 0 or only a handful of customers, trying to service one that's showing interest (but being demanding) feels like the natural thing to do.
But more often than not, the end outcome isn't favourable.
A friend of mine serviced an early user of his app during the early days with free customisations. That same user came back asking for more custom features, while being on the FREE plan, and threatened to write a 1 star review if they didn't. Toxic.
Over a month was spent caving to every inane request of this one customer and the only reason they did it was because the customer was willing to pay $250 and they were the first non-institutional paying customer so they were obsessed with getting it right.
5 figure a month contracts that were soon to start but paused due to the pandemic went unserviced so that large parts of the product could be rewritten to serve this one person as though they were the expert on what non institutional customers wanted. And in the end they wanted nothing more than a custom Craigslist type of ad, just with their own custom style and everything.
Could have spent that month protecting the large contracts.