Your best memory of those early years?
First cigar I really remember smoking... Vegas in my very early 20's. Up about $1200 on a blackjack table at the Flamingo Hilton, just drunk enough to be really enjoying myself. Bullshitting with the pit boss, who calls the cigar/cigarette girl over and tells her to give me a cigar on the house. She gives me Macanudo Portofino. I thought I was the king of the world. Got me hooked.
Your biggest regret?
Not buying more Partagas Coronas and Dip 4s.
Things you would you have done differently - your best piece of advice for newcomers?
If you find something you love, buy A LOT of them. You never know when blends will change or get disco'd. Also, don't stress. Invest in a decent humidor/humidification system and enjoy your smokes. I remember agonizing over every minor change in RH or Temp. Really took the enjoyment out of it at first.