@ian good post. I managed to build DNSimple without shady tactics and can sleep well at night thanks to that.
One little thing in your post:
Must you sacrifice your own morals and common decency to run a successful online business? As someone who’s done it for 12 years I can assure you the answer is NO.
I read that as “I’ve sacrificed my morals for 12 years”. 
I know it’s not that case, just thought I’d bring it up because I chuckled to myself when I read it.
Ha! Will tweak that.
How does everyone feel about seeing a competitor is having customer service issues on social media and reaching out to the customer to offer an alternative? If it’s all out in the public it seems like fair game, especially if you address a pain point.
Reaches out via a direct message or in the competitor’s conversation? The first one I feel is OK, the second one is rude. 
You can’t DM people how don’t follow you on Twitter so it would be a tweet back but only to the customer not the competitor
I did not mean necessary via twitter DM; the channel is not that important as long as it is a point-to-point conversation.
I’m not so sure however about an automated message to everyone who commented in the competitor’s tweets. That sounds like a spam.
I do not have reservations tho against collecting those handles and then have a marketing campaign targeting them (not sure if it is possible).
Then again, if one believes that their software is infinitely better, and not telling the competitor’s users about it is a disservice to the human kind, then anything is OK.
I’m with you, not automated spam, but direct 1 to 1 contact. Sales 101.
I hate it. Totally sleazy. Doesn’t mean it won’t work, but never once have I had it happen to me where I didn’t hate it.
Also, doubtful you’re going to make any wide ranging business impact in that manner. I don’t think time cost vs payoff is there.
Not sure how offering an alternative solution when someone is voicing their displeasure with their current solution is sleazy. It’s 1 - 1 marketing.
Have you ever been in Walmart discussing something with an associate and had someone from Target come up to you and tell you you should come to their store instead? Of course not, because it would be sleazy for Target to hire people to walk around Walmart convincing shoppers to go to Target. Also because it likely wouldn’t bring enough shoppers to move the needle much like harassing people on Twitter won’t.
What you can do is build up a good reputation so that customers speak on your behalf to others who are having trouble with their current providers. That’s better in every way.
100% agree with that, someone championing your product is much more convincing and authentic
That’s not a matching situation. A better example would be a Target rep staying just outside of Walmart and talk to everyone who’s rushing out cursing and promising to burn the place to the ground.
Or an ad banner placed just across the street from the competitor customer service entrance.
Would it pay off (not for Target, for someone monitoring Twitter for negative comments)? It may, if LTV is high.
It is certainly better.
But for a bootstrapper who has only a few customers, pulling unhappy users from under a competitor seems not a bad idea. Them are very warm leads.
How many Walmarts have you walked into with a Target employee out front? How many McDonalds with a Wendy’s employee out front?
Note: I said “if LTV if high”. LTV for Walmart/Target buyers is not high.
I don’t think you’ve thought that through at all. The LTV of a married couple with 2 kids who do their grocery shopping, clothes shopping, and home shopping at Walmart for 10+ years is far higher than the vast majority of SaaS apps people are building.
I thought about that, but decided that Target won’t have a reliable way to keep this newly-won customer, and so the “life” in LTV would be likely short.
At any rate, I do not believe we do not see Target reps because of moral considerations, but only because it doesn’t bring enough money.
On the other hand, I see a large Audi poster right across from the local Chrysler dealership. LTV, eh?
Target can’t keep customers but a one person saas can? I think they have billions of dollars that say otherwise.
It can’t bring them money the same way it can’t bring you enough money. Stalking people on twitter takes a lot of time unless you just straight spam people based on keywords.
An advertisement is nothing like interjecting yourself in the middle of a conversation. Advertise on Twitter all you want.
There’s been some pretty famous campaigns between food chains doing pretty much that exact thing
Fwiw a quick twitter search can show possible unhappy customers if you know what you are looking for, 2 minutes instead of looking at cat gifs