Don't forget to hold on to your health insurance; under COBRA rules you can extend corporate coverage for 18 months on your own dime. By then your company should be robust enough to afford a policy. Once you hire one person, you'll qualify for a group policy, which is almost always cheaper than an individual plan. You can leave your 401(k) behind at your former employer, but you may want to roll it over into an IRA. Then when you open your business' retirement plan, you'll have a relationship with a fund company or an investment manager.