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I was once under the impression that selling web-enabled software was a stupid decision as a solo founder, because it would tether one to a server and uptime problems. I have since found that this is not the actual nature of the world, and that there are many, many reasons why web apps or similar server-dependent software are probably the sweet spot for solo software-product-writing entrepreneurs.

If you're thinking "That sounds like an ideal gig but the technical support burden / server maintenance / etc will crush me", as me for specific elaboration, but in general this is much easier than you think it is.



I couldn't agree more. It was initially my biggest fear, and some of my experiences had begun to make me feel that way. However, as time has gone, I've realized that it's really not that bad. The only catch is that the option of going on a vacation to a remote location without internet and cell phone access is out of the question if you don't have a backup person.

I used to think that adding a second full-time person was the solution for alleviating pain, but now I see it as the way for all of the work to simply be more fun because there's somebody else to help accomplish more.


How can you say that when you also talking about taking calls from customers in the middle of the night? That would be pretty bad for me, at least.


It sounds like this was a question for me, but it looks like a reply to a different comment. I actually never take calls, especially in the middle of the night. :) Sometimes, I'll email customers and ask if they'd like to chat on the phone about their ideas, but phone support isn't realistic for us.

I do respond to emails if it seems like the customer could really benefit from a response, and even sometimes when they aren't looking for a response. Sometimes, if it can wait, I'll go back to sleep and handle it first things in the morning.


Nah, it was memt for patio. I stalk him om here so the taking phone calls was based on another comment he made elsewhere.


That was a very frustrating week, but it was one frustrating week in six years, and I've gotten past it.

Story time: Customer X signed up for the free trial of Appointment Reminder. 3 minutes later he sends an email asking if I can please hop on a call with him. This is at 2 AM Japan time but I am just putzing around on HN so I apologize to Ruriko, say that I'm going to make a five minute phone call, and call him from my cell phone in Japan. He asks a typical pre-sales question, I answer it, and we're done in five minutes.

Fast forward to three hours later: phone rings. Customer X, who now has my Japanese phone number, is calling with a new issue. He has been using the software and thinks that grey text on a yellow button is difficult to read, and I should fix this for him. He sent me an email but I didn't respond to it. I tell him that I live in Japan, that it is 5 AM, and that I will ordinarily respond to emails within 24 hours. He asks another question and I, somewhat testily, strongly suggest writing it in an email and end the conversation.

Next day, he calls back at 2 AM. He wonders whether the software will also send SMSes. I tell him that the first line of text on the front page is "Appointment Reminder sends out customizable phone reminders, text message reminders (also called SMS reminders), and email reminders to your clients, so that they come in on time and you get paid." and that he could have asked this question over email. I then remind him that I am in Japan, that it is 2 AM in the morning, and that the service level for a $29 a month account is best-effort email.

Three days and six calls later I finally lose my patience and tell him something to the effect of: "There is an actual cost involved in having our head engineer wake up at 5 AM to answer your phone calls, which -- by the way -- you have made more of in the last week than our entire customer base has ever. If you need this level of service, you should purchase an SLA, which will cost you north of $5,000 a month, or I will assist you in finding a service provider more appropriate to your needs."

Customer X takes the hint, then begins badgering me over email. Despite having time zones and the 24 hour thing explained multiple times, he gets very upset when I don't respond to emails in 20 minutes. My happiness level deteriorates over the week.

Finally, I tell Customer X that he is making economically non-viable use of customer support, and that if he needs this level of support, I will assist him in finding a provider appropriate to his needs. I then explicitly, for the first time, mention that we can terminate accounts. That's the only time in my life I have hinted at that threat.

This quiets him down. Several weeks later he self-cancels and I take Ruriko out to dinner to celebrate.

But again, compared to the amount of drama I suffered when full-time employed, this is a funny story affecting 2% of my time, I've made a process improvement to avoid it in the future (I now do customer phone calls through a Twilio proxy so they don't get my Japanese cell number and, if someone is X-like again, I will cut them off earlier), and I'm currently enjoying my honeymoon in Hawaii 98% disconnected with no real worries.


I've worried about it, I'm definitely interested in hearing more.




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