Personally, take the sure thing over the big bet. In baseball terms, round the bases with singles instead of always swinging for the home run. Also, don't mar

Personally, take the sure thing over the big bet. In baseball terms, round the bases with singles instead of always swinging for the home run. Also, don't marry someone that you'll have to give everything you've ever earned to get out of your life. It's hard to summarize all my life's experiences. I tried very hard to learn from my parent's and other's mistakes. I'm not a failure, but I'm not retirement wealthy either. Best advice is read a lot of writeups on failed startups more than successful ones (if that's your goal). You learn more by seeing where people could have done better than by studying those that for the most part got lucky (yes they worked hard too, but sometimes timing, connections, location, etc. doesn't work out). If you're looking toward just being successful in your career, that's a different line of study (how to win friends and influence people, etc.). If you'd like to have an actual discussion, shoot me your email. I'd meet the criteria for failed startup founder (I'm on #7 or 8 right now, too lazy to go review how many failed I've had :-)