You're right that telling somebody they are screwed wouldn't help. What would help is figuring out the factors that actually lead to success. I'm guessing things like education, good healthcare, financial literacy, access to capital, role models, etc... all matter.

Work on programs to make sure these basic things are available to everybody. Start mentorship and apprenticeship programs early. Work for a strong social safety net so that people don't have to worry if they start a business and it fails, they won't be homeless or without healthcare.

So don't teach hopelessness. Instead recognize the failures and fix them.