Please do not mistake me asking in a direct way as arrogance, but: Are you making this claim based on the assumptions that cashflows over medium user acquisition & support cost will work out or have you pulled this off yourself?

I'm currently scoping a small - medium enterprise concept with a very concrete set of paying first customers, but thinking ahead this looming uncertainty really bothers me.

To back who you are replying to. My story might be interesting.

Small niche software doesn't suck : if you love that niche, if you can create something that that niche loves and that what you create is difficult for others to replicate.

I have small business with small client base that will forever remain small. ~ 140 clients. A couple of staff members now days.

Cost of acquisition is high. I need to retain a client for 2 years to achieve ROI. That bit is hard work. But you structure things accordingly. From the clients perspective, changing competitors products is very disruptive so I need to make sure I create something that makes it worth their while. The product itself and its capabilities compared to competitors, where the product is headed, support etc around that product and whether or not their is a genuine need for the product.

Making good money. Now bringing home more than market salary, but only after many years of sitting under so probably not at net break even just yet. In a few years all going well I'll sell out and will live very comfortably in retirement off what I expect to be able to sell for.

Fairly happy with my lifestyle. Flexible and generally a little less hours than full time. Can be pressured/stressful at times but no more than I remember when I worked for others.

I'll never be Peter Thiel wealthy but I am on track to achieve my financial goals.

Congrats! Fellow entrepreneur, interested to hear more about your story.

I can't talk for OP but I've been running a software company with both software products and bespoke service lines that generate a good level of income...I reckon I can assist you with your uncertainty - feel free to email me on [email protected]

It's a matter of scaling. Small business-focused products generally will scale linearly with inputs. Good for a "lifestyle" business that keeps its owners and employees happy, bad for a VC-funded business that needs to hit a grand slam just to break even.

And this is why, from the point of view of a "lifestyle" business owner, VC funding looks like the kiss of death. Scaling fast is risky, and if you're gambling with your own money, you don't want to be forced to turn your sure bet into someone else's moonshot.