A year ago, I decided to take a leap of faith. I left my perfectly fine, thousands of team members company, and joined a startup of approximately thirty people. "Why would you do this?", "But you have children!", "You will burn out", were some of the phrases I heard. Was I scared? Yes. Was it risky? Yes. Would I do it again? Absolutely. This story is for you if you are in a portion of your career, where you find yourself tempted by the perspective of leaving the comfort of your current established role and joining a potential unicorn company that could provide you with a challenge, and a reward, big enough to buy a jet fighter. This talk is for you if you have recruiters calling you, or friends enticing you to join their teams at companies in early stages of funding. You will acquire a playbook filled with questions about burn rate, communication style, culture, and stock vesting. You will hear the cold hard truth about why working for a startup is awesome, but also extremely challenging, no bull, no sugar coating, no recruiting. At the end of the day, the decision and the risks are yours, but the experience and potential may just be worth the grey hairs. At least that is my current hope.