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I've been thinking about this a bit, and am also interested in others views of this.

Increasingly I think the way to increase your chances of success is to pick a problem space that applies to both large and small businesses, and forget about the large businesses for a long time.

Small businesses are generally going to be more open to building with you, taking a risk, accepting that you don't yet have SOC2, etc. Often they are in a similar place maturity wise so they are (more likely to be) understanding

I'd love to hear others views on how to approach this though - most of my ideas for side projects are inspired by friction/frustration I'm encountering in the workplace, and therefore b2b. Even with targeting small businesses I'm still uncertain where the bar is, and how to balance financial risk when looking for product market fit in a bootstrapped/side gig fashion.

I don't yet have anything ready to attempt to sell, but I'm thinking entrepreneur meetups or something might be a good route - assuming I've built something that solves an acute problem experienced early in a companies life might be the best way to go



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