Well, 'Rich Dad Poor Dad' by Robert Kiyosaki is very popular. It tells the story of two dads with different financial mindsets and offers valuable lessons on financial intelligence and entrepreneurship.
One great book is 'The Lean Startup' by Eric Ries. It's a must - read for entrepreneurs. It offers practical advice on building and growing a startup in a very competitive market.
Common caricature hairstyles for senior citizens could be a very short, spiky cut or a full, white afro. Sometimes they are shown with a comb-over to add a comical effect.