How do you stay competitive with similar products without instituting deadlines?

I work for a small company (less than 10 employees) that follows a very similar working process. No deadlines, one (very short) weekly meeting. We don't try to stay competitive with similar products. That's impossible with VC funding flooding the market. What we do instead is focus on making our current customers happy. Everyone is involved in support. We follow up with customers when we do launch features they requested, even if that's years later. It seems to be working well. It's not going to be hockey stick growth, but "freedom" for us (the employees) is well preserved.

I'm glad to hear that works for you.

I'm a customer of several smallish (but bigger than 10 employees) services and if I'm paying something like $120/year for something even remotely useful, I'm not going to switch unless the competition solves a specific problem or I'm really mad at the current provider. In the former case I would at least have told support about my problem.

I do believe that there is "enough" money to be made solving real-world problems for people and treating them like humans so they aren't going to drop you like a hot rock at the first chance. I'm happy to see some voices confirming that in this thread.

Yeah, we see plenty of churn on smaller/newer accounts, but a good chunk of our customers, especially on the larger plans, have been with us for years. It's partly platform lock in, because it's probably a pain to switch, but I like to think it's also we solve a majority of their needs at a decent price and provide good support. So why would they switch? I think it also helps that we are generally targeting that small to medium size company. Or even smaller departments/teams within larger companies. So we're not subject to the whims of a C-suite that is looking to cut 5% off their budget every quarter.

Signal?

No, http://ghostinspector.com/

I thought that plan sounded pretty good, except for the health insurance part. Where do you get your health insurance?

I can't speak for the OP but, since you are a contractor and not an employee, wouldn't you get your health insurance in exactly the same place as all the other independent contractors do in your country?

[Edit to clarify because this is being downvoted: many countries require that independent contractors buy private health insurance. Germany, where I live, requires it. As I understand it the situation is similar, for different reasons, in the USA. So independent contractors are very often all in the same boat, insurance-wise, but that boat varies by country.]

In the US, you can buy medical insurance from the same mega corps that offer it through Fortune 500 companies... its just not subsidized by your employer so you pay larger premiums.

They might be the same corporations offering coverage, but the plans are different. It isn't just the employer subsidization that you need to factor in, but that you as an individual will never be able to negotiate the terms of the plans you're offered, nor will you be able to negotiate for group plan rates.

I didn’t say anything about pricing.

You pay the whole premium more like. The plans in the state exchanges are pretty decent at least in WA. Gold level plans are about equal to a decent average company plan (not like a Google level one)

I'm really interested in reducing meetings by writing more, can you give some insights on how you do it ? Thanks !

I'm sure there are specifics for Gumroad, but there are lots of insights available via other remote companies:

https://blog.doist.com/asynchronous-communication/

https://zapier.com/blog/how-to-work-asynchronously/

Basically instead of waiting for a meeting to communicate, just write it down and send it out, via Slack or whatever. People can consume it on their own time.

I'll read it thanks!

It strikes me how atypical your landing pages are. I can't imagine that it converts into signups as well as it could. The front page offers little of substance. I'm curious if this is the result of testing multiple designs or if little effort has gone into optimizing so far?

i reckon most people learn about gumroad just seeing how other people make money on gumroad. that is what i did.

I'm also surprised by this, and I'm surprised by the fact that the focus seems to be on selling. It's not at all clear to me how all the buyers find what's being sold (maybe I'm missing an alternate landing page for buyers?).