More first cigars are ruined in the first ninety seconds than at any other point in the smoke. A cut that goes too deep unravels the cap and fills your mouth with loose filler. A light that catches one side of the foot before the other sets up a burn that runs crooked for the rest of the hour. Both are easy to avoid, and neither requires expensive tools.
Start with the cut. Find the shoulder - the point where the rounded cap stops and the straight body of the cigar begins - and cut just below it, taking off roughly 2 millimetres of cap. That is far less than most people expect. The cap is what holds the wrapper leaf closed at the head; remove too much and there is nothing binding the wrapper, and it will peel back as the cigar warms. A double-guillotine cutter is the most forgiving tool for a beginner. A punch cut is cleaner still but only suits round heads and larger ring gauges; a V-cut gives a concentrated draw that some blends reward and others choke on.
Commit to the cut. A hesitant, sawing motion tears the wrapper. One decisive squeeze, all the way through, is what you want. If your cutter is dull enough that a single squeeze does not do it, replace it - a dull cutter has ended more good cigars than any other piece of equipment behind our bar.
Now toast the foot before you light it. Hold the flame about half an inch below the foot, off to one side, and rotate the cigar slowly without the flame ever touching the tobacco. You are warming the foot, not igniting it. After fifteen or twenty seconds you will see an even ring of orange glow around the whole circumference. That ring is the whole point: it is what gives you an even burn line for the next hour.
Only then draw. Bring the cigar to your lips, hold the flame just below the foot again, and take slow, gentle draws while rotating. Three or four draws is usually enough. Then take the cigar out, look at the foot, and gently blow across it - you want an even, glowing circle with no dark patches. If one side is lagging, touch it up now rather than fifteen minutes from now when the burn has gone properly crooked.
Two things to avoid. First, a soft-flame lighter that runs on lighter fluid; the fuel taints the first third of the smoke and there is no recovering from it. Use a butane torch, a butane soft flame, or a cedar spill. Second, do not relight repeatedly through the smoke. A cigar that has gone out for more than a few minutes has cooled, and relighting cold tobacco produces a harsh, ashy character. Draw once every minute or so and it will stay lit on its own.
If any of the above sounds fussy, come sit with us for an evening. Every member of the lounge staff will happily cut and light your first one for you, and watching it done once is worth more than reading it three times.