7 Entrepreneurial Lessons Learned From Years of Bartending


Thinking of starting your own business? Before jumping in, do yourself a favor: tie on an apron, shake up a martini, and chat with a stranger or two about their love lives. Take it from me: be a bartender. 

I bartended for years in my 20’s, all over New York City. I served the corporate Midtown happy-hour drinkers, the beer-guzzling frat scene on the Upper East Side, the hipster contingency in Brooklyn, and the blue-collar crowd down in the East Village. I moonlighted while working my full-time graphic design job. I’d rush to clock in after auditions. I spent hours polishing glasses, squeezing fresh citrus juice, reconciling credit card receipts and listening to customers talk politics. Looking back, I was just trying to pay rent; who knew it would solidify skills and tenets that would one day lead to entrepreneurship?

Whether you’re a server, bartender, chef or customer service rep, working in the service industry teaches some great, hands-on lessons. Here are seven of them. Cheers!

1) You will make mistakes — and it’s okay. Tune out the noise, learn your lesson, and move on.

My first time slinging drinks was at the ripe age of 21, at Carolina-style BBQ joint Brother Jimmy’s. I was green, naive, and a newbie to New York. Not even a real drinker myself, my mind reeled as I fumbled through the maelstrom of beer taps, cases upon cases of liquor, speed racks and soda guns, coolers full of icy bottles of beer, and various regulars whom I was told it was imperative to recognize.

One busy night, I found myself serving a man shrouded in a trenchcoat and sunglasses, drinking by himself in the middle of the bar. I noticed he was finishing up his second cocktail; I asked if he wanted another, and he told me he had a tab going. I looked. I couldn’t find it. Instead of asking my senior bartender Dave about it (he was crazy busy at the service end of the bar), I decided start a new check for Trenchcoat and add his previous drinks to it. Then I brought him the check. He looked at it in disgust and called Dave over, who hurriedly grabbed the tab and ripped it up. “Angela’s new, sorry — she didn’t know we totally take care of you here.” Dave then introduced us. Red-faced, I mumbled an apology and extended my hand to Lenny Dykstra of the New York Mets.


I learned I should have introduced myself to the customer earlier. I should have asked Dave about the tab no matter how busy he was. I should not have brought the bill out to a customer who wasn’t ready to leave. Perhaps I should’ve done my homework, knowing that pro athletes liked to hang here — but I didn’t. So I had to make the best of it in the end. And yes, I’ve also learned that you get a handful of customers (celebs or not) who don’t treat you well. You live through it, you figure out how to handle it the next time around, you move on.

In Mamachic’s first year of business, I’ve already learned some big “hindsight” lessons as far as production, marketing strategy, and business pitches. A few weeks ago, I sent out a customer survey about the actual product, which provided insight on my initial missteps. For instance, a few said that I should include a more thorough booklet that explains how to wear the Mamachic. The online how-to video we shot moved too quickly for some to retain. Awesome. Here is simple, focused feedback that I can learn from. I won’t dwell in what I did “wrong” — my product and business can only get stronger, moving forward.

2) Multi-tasking skills are vital.

The most fast and furious I’ve ever worked in my life was at dive bar Bar None, near NYU. Every night, we’d get mobbed with college kids, locals, and the bridge-and-tunnel crowd. The throngs of people literally piling up to the bar were insane. Here’s a typical two minutes for me on a given night: I’d take multiple orders at once without writing a thing down, immediately total up each bill on the spot (in my head) so the customers could be ready with their payment, make all the drinks in order of efficiency (even if they weren’t part of the same order), and dole them out to the right people in the same sequence that they ordered. All in under two minutes, with a smile.

Now, running my own business, I am constantly ruminating over the 10 or so things that are urgent on the docket — whether it be troubleshooting new samples with my factory, reaching out to potential brand partners, writing brilliant blog posts (like this), curating social media posts, reconciling expenses, designing retail packaging, figuring out new marketing strategies, refining investor pitches — just to name a few. While they’re all important, it takes a keen eye (and some trial and error) to figure out efficiency, get it all done — with a smile.

3) Be daring & brave in engaging with customers.

Screenshot 2015-11-11 22.06.17Starting your own business from the ground up is not for the faint of heart — and neither is bartending. In both cases, stepping out of your social comfort zone and interfacing with customers is key. Flame Deal worked her way up from behind the bar at Brother Jimmy’s in New York, to becoming a managing partner there, and eventually started her own event planning company.  As a bartender, she saw firsthand how she could make a positive impact on customers by engaging with them, standing less than four feet away. “Bartending made me brave enough to talk to strangers,” she says. “Quickly they became my regulars, and I knew I made a difference in not only the bar’s business, but the customer’s lives.”

Deal’s outreach strategy helped reel in some high-profile customers to Brother Jimmy’s, including sports icons Derek Jeter, David Cone, Roger Clemmons, and ESPN commentator Dan Patrick. Your business can also land customers far and wide, too — you just gotta have the guts to reach out to them in the first place.

4)  If you’re having a good time, your customers will too — and they’ll buy what you’re selling. 

Screenshot 2015-11-11 22.06.55New York City native Jamie Jensen bartended at Bar None and Webster Hall for years, and now runs her own copywriting business, Your Hot Copy. She has seen firsthand how her clients’ negative moods can destroy their sales. “I can’t tell you how many times I’ve helped an entrepreneur with their service or product descriptions, only to discover that their fear, or dissatisfaction, straight-up exhaustion or lack of perspective was interfering with selling. Picture a miserable bartender mixing your drinks and pouring your shots. You’re not about to throw one back and be like ‘Yay, let’s party!'”

Jensen’s words are, as always, spot on. Working a service job can refine major compartmentalization skills. Even if I was having a rotten morning, or going through a breakup, or on my period — I wouldn’t bring any of that to the bar.  And luckily, current Mamachic work can be very creative, hands-on, productive and fun. As Jensen advises, “Give your audience and customers a fun experience, by exuding fun.” Do it!

5) Treat your co-workers with the utmost respect.

Barbacks are amongst the hardest-working people I know. At Bar None, Filipe and his son Gonzalo put in 12 hours a day working on the nitty-gritty — restocking inventory, scrubbing down the sticky, grungy bar, cleaning the bathrooms — you name it. They closed the bar at 5 am, and often were the first ones setting it back up in the morning. Without them, there would be no bar. I always made sure to thank them profusely when I tipped them out. Even at the feverish, chaotic times of the night, I never once lost my cool and demanded they do something for me. We were friends. So, during operational hours, they ran for me, and because of their efficiency and attention, tips were bigger all around, and everyone was happy.

With Mamachic, I am so appreciative of all the partnerships and connections I’ve made, from working with Opportunity Threads, Factory45 and KenDor Textiles, to fellow business owners and brands, that I don’t take anything — or anyone — for granted.

6) Customers prefer things “straight up.”

There’s a reason why drinks are made right on the bar, for all to witness: patrons want to see exactly what goes into the making of their purchase.  Who wouldn’t appreciate directness as well as transparency? According to Jamie Jensen, that’s why it’s extremely important to be clear in explaining what you do, and what you’re offering. “Putting too much clever into your branding and business is like adding too much juice to a drink. If they wanted Capri Sun, they would have never left grade school.”

Strive to be a trustworthy brand. Jensen adds, “Don’t be afraid to give your customers the goods by being honest with them about your services and products. That’s all they really want.”

7) Attitude is everything.

Screenshot 2015-11-11 22.07.31Shannon Whitehead, founder of sustainable fashion accelerator Factory45, was 22 years old when she landed her first bartending gig at an Irish pub in downtown Boston. As she followed that up with bar jobs in Australia and South Africa while traveling, she learned the importance of keeping her cool under stress.

“Some of my most high-stress nights behind the bar were when the place is packed and I accidentally hit a glass on the side of the ice well. It breaks into a million pieces into the ice that is supposed to go into customers’ drinks. While the bar-back digs out the ice and replaces it, patrons start yelling at me to hurry up and make their drinks. The only thing I can do in that situation is put a smile on my face, apologize for the delay and say, ‘S#!t happens.'”

In running your own business, things certainly don’t go perfectly the first time around. Delays will happen. Setbacks will hit you in the face and seem to knock you cold. The difference between a good business owner and a great business owner is your ability to roll with the punches, look ahead, and keep on trucking.


Meet the expert contributors to this post:

FLAME DEAL is the woman, the myth, and the legend behind Brother Jimmy’s BBQ, and helped solidify its status as a New York City institution. She has reeled in a multitude of high-profile regulars for the bar, and as a managing partner, increased restaurant revenue sales to over $12 million. She helmed her own event planning company Flame Deal Events, for over five years.


JAMIE JENSEN created Your Hot Copy to serve the fun-tastic entrepreneurs of the wild, wild web. To date, Your Hot Copy has helped over 100 businesses go BIG with their brand and get CLEAR with their communication.


SHANNON WHITEHEAD is the founder of Factory45, an accelerator program that takes sustainable apparel companies from idea to launch. Shannon got her start in 2010 when she co-founded {r}evolution apparel, an ethical clothing company for female travelers and minimalists that was featured in The New York Times, Forbes.com, TheWallStreetJournal.com and Yahoo! News.

4 replies
  1. Lisa J
    Lisa J says:

    Excellent points. Definitely working a service industry makes you tougher, too. You hear a lot more criticism but then learn to respond to it quickly and productively, and you don’t take much personal offense. If anything your skin gets thicker.

  2. Lisa Ann
    Lisa Ann says:

    Yes working in the service industry teaches so many lessons… working since 1981 and I love being in service to people and with people. And it makes you honor the service providers in your life as we all live and work among one another.


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