Here are questions I'd think about: * Why are they interested in your company? If it's technology, would others be interested in the same technology? What are

Here are questions I'd think about: * Why are they interested in your company? If it's technology, would others be interested in the same technology? What are alternatives to your tech? Scarcity and competition will drive up prices. A good investment banker can help you identify these opportunities and get the most out of your situation. If it's for the market opportunity, you want to consider the buy-it versus build-it quandary they are evaluating and keep this in mind as you negotiate. * Are you through the risky part of you business? When you start a new venture, there is a huge amount of risk you are assuming, particularly on the front that the business will actually work. If you've proven the business will work for your customers and the business model will be profitable, you're in a much higher position of leverage. If your business is not clear of risk yet, you should keep this in mind. * What is your chance of success at this company and how will it affect how much cash you'll be able to extract from the deal/stocks? Will you be caught up with red tape? Is it going to be like delicious at Yahoo? Will you have control over your future? * Are you planning for the worst case scenario? If they could fire you on day 2 and leave you with almost nothing, I'd never agree to it. Contracts and agreements should be planned with the mindset that if things can go wrong, they will go wrong. * How can you get more money sooner? A mostly stock deal that was vested over 4 years the deal seems crazy for me personally unless it'll set you up for life. You've gotten a taste of entrepreneurship. You have been genetically mutated forever and will never be normal again. You'll likely get the bug to start something else in a year or 2... or sooner so keep that into account when thinking through the deal. Good luck.