Working with startups often leads to accumulating technical debt for three main reasons: (1) the need to get products out quickly to validate ideas, (2) a preference for solutions that are easy to implement using familiar skills and concepts, and (3) prioritizing new features over refactoring due to time pressures and financial needs. The top ways to minimize resulting damage include incrementally refactoring without stopping product development, carefully considering whether paying down technical debt principal is less costly than accumulating more interest, and decomposing monolithic systems into independent components.