Success as a Tipped Employee

My life has never been “normal.” When I supported myself and my family with tips working as a server and bartender for decades this was made clear often. I had regulars at a prime steakhouse here in Chicago who would spend frivolously and tip me even more recklessly – the first time they came in they added the subtotal and tip incorrectly: the accident would put an extra $1,000 in my pocket. Following protocol, I pointed out the error and asked them to change the total, so that they were not overcharged (and I wouldn’t risk being in trouble too). They’re reply? “Oh, that was my bad, not yours. Just round up!”

Over the next several years this small group made me their regular, flying me on private jets to Vegas, taking me to sky box suites to my favorite local sports events and concerts, and tipped me hundreds of thousands of dollars. Servers would line-up behind me to watch me close out checks when they’d come in – $5,000, $10,000; they once tipped me nearly $20,000 on a single bill when they found out I had to split/share the tip. Being their regular server was something I never took for granted – I was always going above and beyond to continue to earn their business, as it were. We’d become “friends,” but I never lost sight of the fact that I was their servant (albeit a well-paid one).

If you google “Canopy Financial” you’ll see OpEds and news articles about the two founders embezzling hundreds of millions of dollars and getting caught. One killed himself, the other is serving decades in federal prison. These were my regulars. My managers at the steakhouse had always told me that what was happening with them and I was not normal. It turned out they were right.

The distillate? When things seem too good to be true, often they are – but that does not mean they won’t still happen. I impressed them initially by being conversational, welcoming, thorough, and offering to go above and beyond from the word “go.” Although not everyone will get five-figure tips from it – it’s a formula that is certain to ensure financial success as a tipped employee.

Cory Warfield, Founder and Chief Visionary Officer, ShedWool