I actually think this is a very fair question. An important one.
Start-ups are businesses. Very competitive businesses--more so today than at any time in my career. This is capitalism, not charity. It's not a game. Yes, it's about the journey. But a journey to something that makes the founders no money is a failed journey, to me.
The real answer, statistically is: Almost None of Them.
But, if you (x) build a great company, (y) that really gets to Scale, in a hot space, and (z) don't get diluted to nothing ... (aa) and get acquired (or IPO, but let's put that aside) ... you WILL make a million dollars.
There are something like 40-80 acquisitions like this per year, in internet/tech, as near as I can tell that are acquired for $40m+ or more and have raised significantly less capital than their acqusition price. If that happens, and you are truly a co-founder, you have a good chance to make $1,000,000. Just do the math.
So it's "simple": co-found and build one of the best 40-80 companies possible each year, build it to something great with true scale, with blood sweat and tears, with the best possible founders ... budget years to get there, not months, as you seem to be doing ... and you've got a very solid shot at "making you a millionaire".
Aim low though--not to build one of the best 40-80 (call it Top 50) new start-ups a year ... and your odds go way, way, way down. Don't just start something 11% better than another start-up that is barely in the Top 50 themselves. Don't just give it a year to see how it goes. That won't get you into the Top 50 of This Year.
It's not random. There's a lot of luck, yes, but it's not random. If it were, there were be no early stage VCs. And if you look at the track record of repeat founders ... maybe luck is actually a very small part of it. Maybe luck is really or at least mostly just executing really well (great co-founders) in an emerging market that explodes (deep insight and commitment, ability to be hyper-limber and evolve rapidly ... but not luck).
And it's OK to talk about money--quietly, with your co-founder. Not every day, but at the beginning ... and the end ... you should.
*40-80 a year data extrapolated from here:
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