Software that supports a lifestyle business is typically different than YC scale or ideas accepted by YC. If your goal is to build a lifestyle business that affords a salary of ~$100K, you likely don't need to scale beyond $1M in revenue.

You would actively want to avoid raising money (from YC or other investors) because their goals are to get companies to $100M+. That isn't a bad thing — it actually opens up the door to a much wider range of problems & niches, with more flexibility & less pressure.

1. Given the above, scrap the YC aspect of the question. But ideas can come from your own experiences with problems or pain points you felt. Or can pick an industry or role and have conversations with people to find common issues or challenges.

2 & 3. This depends on the vertical & industry you serve + their role. If you're selling to VP of sales of startups, can get by with emailing + LinkedIn. If you're selling to local professional services, can get by with cold calling. Where you build your list will depend on your target.

Selling to owners of < 10 employees) is very different to < 100 and so on.

If your business is tiny it can be hard to sell to a business that is large. The larger the business the more they evaluate your business as a potential long-term supplier and less about the product.

As you are starting out I recommend talking to smaller, rather than larger businesses.

The key insight was: marketing was the most important part. And the most important part of marketing was finding (and validating) a painful problem businesses would pay for.

- It is important to talk directly with real prospects: real business owners. You can use stuff like Gartner reports to help find a niche, but it is essential to talk directly with real people who have the problem.

- Validation involved getting a prepayment even though the software did not exist. Not even a design. Prepayment got the initial 10 or so "champions" a lifetime discount and personal input into how the app would be developed.

- The prepayments served as a much stronger validation than a verbal "yes." Also it funded development of the initial version. The 10 champions' input also made the initial version much better.

- Generally, a "painful" problem will result in at least a 10X ROI (additional revenue, saved expenses, saved time, etc). If you describe the painful problem better than the prospects themselves can, they will assume you have the solution and jump straight to "how do I pay you? (sign up)"

- The market research math is roughly: find a niche with at least 10,000 prospects. Plan to capture 1% of this market, or 100 customers. If you can find a painful problem whose solution is worth paying $100-200/month, you should be able to achieve $80K profit/year.

(The Paperless Pipeline origin story is slightly different. For example, there was really only a single true "champion." But this champion was the happy customer of another SaaS that was built with the same process. This champion kept asking for this other SaaS that turned into PaperlessPipeline.)

---

So I think the resources below provide the most risk-free (highest chance of success) way of achieving your goal (I think YC targets "unicorns" with much higher potential ROI with the understanding at least 90% will fail):

- The founder of Paperless Pipeline has been teaching his method: https://startfromzero.com (Specifically "Idea Extraction" is the most important part)

- Apparently he is going to start a YouTube channel where he teaches his stuff for free.

- https://30x500.com is another great course that teaches a similar method, and more geared toward engineer-types.

- https://shop.stackingthebricks.com: Kind of like the a-la-carte version of the 30x500. The two most valuable parts are probably "Sales Safari" and "Just F*ckin Ship."

Second question, if your goal is to make less than $100K, any developer job in the US in second tier major city pays that much for junior/mix developers on average with a lot less work. Heck I made that much non inflation adjusted in 2001 working at a no name company as a VB6/C++ developer in Atlanta, four years out of school.

Can you sell? Can you build? Can you pivot without ego? Can you deal with snakes/assholes who try to sabotage you? Can you fail? Can you deal with no profit for some time? Can you do all these and way more at the same time?

Congrats you might have a chance!

Maybe you can do consulting? Or some other services based thing? Might be easier and give you a good income to live on.

If you want to do venture scale (read: 1 billion USD outcome or bigger) you need to answer those questions I asked.