It took me about 10 years to gently convince an investment-averse friend to put money into stocks. She has a retirement account through work, a rental property, and tons of savings from thrifty living. We are comfortable sharing financial details with each other. I never pressured her, but whenever the conversation turned to that topic I would tell her my index fund investments have returned over 7% over time... while her savings account has been earning less than 1%... A few months ago she put about $5,000 into VTSAX (probably 10% of her current cash holdings) and immediately told me. I was so proud!!!