I hear you. My worry is that if we say "all UConn grads who stay in CT," thats a ton of people who are already staying in CT, so it doesn't create as much change. I also went to UConn and I respect its value, but there is a huge range of intelligence and talent there. There are some people who go through UConn that are absolutely brilliant, and some who are not smart at all, and who I don't think it would be worth investing in. My opinion (which may be wrong) is that schools like Yale don't have that same wide range in its students abilities. You make a good point in regards to giving to folks who show some sort of quantitative metric for improving the state economy, but it would have to be more broad than something that fits only entrepreneurs. Doctors, lawyers, engineers are just some folks who would be unlikely candidates to start a business, but whose value is very high. That makes me wonder if maybe GPA or test scores could be a determining factor, as the program would only attract people to stay in state if they guarantee the loans paid back, and less folks would be willing to take a gamble that they would start a successful business and then guarantee getting loans paid for (not sure if that wording makes sense). Basically, I'm trying to say that you'd need to find a way to secure the repayment program before people even entered the work force to get large numbers to agree to it, and that in it of itself would mean that we can't use metrics like how many folks you employ, etc. It would be difficult to figure out the particulars, but like others have noted, Boston tech succeeds because of Harvard and MIT, so it's important to keep Yale folks in CT to do the same.