My favorite quote: "A man holding a cat by the tail learns something he can learn in no other way" -Mark Twain You need to grab that tail and learn things yo

My favorite quote: "A man holding a cat by the tail learns something he can learn in no other way" -Mark Twain You need to grab that tail and learn things you will not otherwise. From that it follows that the answer to your question is: As early as possible. This also means you probably should not make your first experiences the most grandiose ideas. You might actually want to assume failure. Don't assume you know anything about business at all. Jump in. Make mistakes. Learn. If you get lucky, great. If your experience is +/- on standard deviation from the mean, you'll come out of the experience all cut-up and bloody (image: holding cat by tail). And you will also come out with tons of wisdom. That's why you don't bet the farm on your first attempts. You are far more likely to fail. Don't worry. Keep going. Make small bets. Don't risk it all in one hand. Make small bets and learn. Definitely self-fund. Don't play with someone else's money. I know this is very much counter to the YC/SV culture of funding young teams with and idea and zero business experience. So be it. Around 90% of startups fail. YC does a bit better than that. I think I can say that failure is far more probable than success. So, fail small and fail a bunch of times. Every try to learn to play a musical instrument? You can't learn without constantly making mistakes. In fact, neuroscience tells us that learning requires making mistakes. Why should business be any different? Can you start something with a few hundred dollars? If you fail, so be it. You will learn invaluable lessons. The challenge from The Wolf of Wall Street, "Sell me this pen", is extremely important. You have to understand how to sell. If you don't, and your competition does, you are never going to succeed. At the end of the day, making a better mousetrap isn't enough. In fact, making the same mousetrap is just fine if you are good at selling. I know a guy who decided to sell US flags. He didn't make anything. He bought them from a manufacturer and focused on selling. He was soon making over three million dollars per year. Sell me this pen.