1. Is he asking for your feedback? Founders are forever hearing "that will never work, you should go back to your job." If he's not soliciting your feedback, consider deciding not to pile on.
2. Conversely, if he is asking, give it to him straight. People have a tendency to think "this will never work" while saying things like, "wow, that's cool!" Don't be that guy. He won't appreciate it when he thinks back to the years of time wasted.
3. If you do give feedback, focus on concrete and constructive building blocks, not your value judgments. "How will you solve the chicken and egg problem?" is a far more useful phrasing than "Your latest idea will never work." For bonus points, brainstorm solutions with him. This is harder and more time-consuming, but more helpful for your friend.
4. Remember that the most successful ideas are often the most counterintuitive. Twitter is my favorite example here, but honestly it applies to most huge tech companies. Keep an open mind through the process.
Good luck! Entrepreneurs can seem schizophrenic, balancing logical considerations with the desire to do something extraordinary and contrarian. But helping him navigate this is what makes you a good friend. :)
3 especially. Communicating the "why specifically" is what distinguishes you from the "don't get it" types and is less hostile than implying that he couldn't possibly understand the why.
I've been in many situations (though more about philosophical ideas than business ones) where someone would repeatedly insist that something I was proposing was wrong, and only by extensive research did I find out that the whole time they could have just said X, and it would have made sense. (Or discover that they didn't understand the field or idea as well as they claimed.)
1. Is he asking for your feedback? Founders are forever hearing "that will never work, you should go back to your job." If he's not soliciting your feedback, consider deciding not to pile on.
2. Conversely, if he is asking, give it to him straight. People have a tendency to think "this will never work" while saying things like, "wow, that's cool!" Don't be that guy. He won't appreciate it when he thinks back to the years of time wasted.
3. If you do give feedback, focus on concrete and constructive building blocks, not your value judgments. "How will you solve the chicken and egg problem?" is a far more useful phrasing than "Your latest idea will never work." For bonus points, brainstorm solutions with him. This is harder and more time-consuming, but more helpful for your friend.
4. Remember that the most successful ideas are often the most counterintuitive. Twitter is my favorite example here, but honestly it applies to most huge tech companies. Keep an open mind through the process.
Good luck! Entrepreneurs can seem schizophrenic, balancing logical considerations with the desire to do something extraordinary and contrarian. But helping him navigate this is what makes you a good friend. :)