PODCAST: Guide to Tipping Etiquette

The Sharp Gentleman's Guide to Tipping etiquetteToday’s podcast is about something you’re all familiar with, but may not know exactly what the rules are in it: tipping etiquette. Gratuity – when should you, how much should you, what makes a good tip, why should you, etc. These questions roll around the heads of many men every day, and we’re here to talk about what the rules are, and what to be aware of in the tipping world.

This is also a special show because I’m introducing my friend, and potential future podcast cohost, Oscar Guerrero to all of you. He’s a stand up guy that has his own story of struggling to make sense of the world and how, after an anxiety attack in front of his CEO, he literally “got a grip” and started working to make himself and the people around him…better.

Today’s show is about knowing the right time and amount to tip, but more importantly, it’s about why you should be a good tipper in the first place.

Take a listen to the show and don’t forget to leave a comment below on what you think about tipping and gratuity in today’s modern society. [remember to Subscribe Here]

Subscribe Here

Show Notes

Oscar Guerrero The Sharp Gentleman Podcast Blake HammertonFirst things first, allow me to introduce Oscar Guerrero. Oscar G. is a Colombian American gentleman living in the Miami area. A world traveler since an early age, Oscar spent the first half of his 20s living and working in China. Now back in Miami, he works in global marketing at a Fortune 1000 company and has a strong passion for personal development and fashion.

Oscar quietly struggled most of his life with self doubt, confidence and anxiety issues. It wasn’t until that anxiety attack in front of his CEO that he realized that he needed to confront his fears head on and take control of his life before they took control of him.

A certified life coach, stylist and self proclaimed “personal development guinea pig”, he is now on a mission to share his story and help other men overcome their personal fears, take control of their limiting beliefs, and become the confident men they were born to be.

Remember, if you think he should stay and be a permanent part of the Sharp Gentleman, let us know! Leave a comment below and we’ll let you decide his fate! :::::evil laughter:::::

We’ve all been that guy…

Look, we’ve all been that guy – the one who tips too little on a bill that’s too big. There are a myriad of reasons why we did/do it – we hated the service, we didn’t have enough in our checking account, we didn’t have any extra cash… whatever the reason, we didn’t leave the customary 15%+ on the table. Don’t worry, my friend, we’re going to help figure out the rules of tipping and how to always feel comfortable with what you leave behind.

What Oscar and I explore is the cultural norms surrounding tipping etiquette. Is tipping a universal construct? Do all countries and cultures tip? The answer is no. Many of us know that certain cultures aren’t aware of the tipping standards in the US, and who can blame them? Let’s be honest for a second here, where is the manual that describes where we should tip, how much, and for what reason?

The instructions don’t exist.

Here’s what you need to know about tipping in America:

1. Tipping isn’t universal.

People from outside the US aren’t accustomed to tipping, so cut them some slack. It’s not that they’re bad patrons; they’re just from a culture where tipping is either not required, not expected, or insulting. If you travel to some cultures and tip there, it may be poorly received because they’re not a tipping-friendly society. It’s considered an insult.

2. Do not go out without considering the tip.

One of the biggest mistakes guys make –especially when on a date– is leaving a poor tip after a nice meal. Jami (my fiancée) has been in the service industry for a decade now, and it makes us keenly aware of the guys that take a girl out and pay close attention to her, only to completely shaft the server that waited on them all night. This is a big no-no.

Imagine for a moment two scenarios:

  1. You take her out and treat her right, but you tip $3 on a $57 dinner. She happens to glance at the bill and sees your meager (honestly shameful) tip. She also happens to be a server or bartender somewhere else. Your chances of date #2 are done, my friend. You are the cheapskate that doesn’t value servers, in her mind… which means you don’t value her. You = toast.
  2. Same scenario, but she’s not in the service industry. She sees the meager tip, judges you as being cheap, feels bad, and “goes to the bathroom” before leaving. This is so she can tip the server on her way there as a way of apologizing for you. Again, you = toast.

If you can’t afford to pay for the service, don’t go to a restaurant. Great date alternatives are picnics, home-cooked meals, and carry-out.

3. Consider your time investment.

Tipping Etiquette - The Sharp Gentleman Podcast - Oscar Guerrero Blake HammertonOne of the biggest gripes I hear from servers and bartenders about patrons is their lousy tips after factoring in their time investment. When considering what to tip on a meal or drinks, take into account the time your server invested in making your experience better. If you and your date split an appetizer and each had two drinks, but were at the bar / restaurant for 3 hours, factor that into your tip. Your server kept your satisfaction in mind the entire time and may have given up other tables and tips to serve you. Treat him or her accordingly.

This is also a good time to bring up services that encourage tipping, but don’t often get it due to their time-value equation. Professional body piercers, for example, often have a tip jar, but the body piercing is already expensive and takes less than 3 minutes to perform. It’s hard for many of us (myself included) to justify a tip on an already silly price tag. Another place is the local coffee shop. They have a tip jar, and it’s a good place for loose change, but not necessary. Although, if you frequent the same place often, my professional advice is to tip your barista. He or she will remember you, give you preferential treatment, and often comp. drinks for you. Your grandmother’s idea of catching more flies with honey than with vinegar is most assuredly alive and well.

4. Give 15%+ because it’s good for you.

Already, I can feel some of you preparing to write me angry rebuttals on this one, referencing bad service, freedom of choice, and general “don’t tell me what to do” opinion pieces. Here’s the truth, Gentlemen: you can afford it. You’re more than capable of being the bigger man and providing compensation to someone that helped add value to your experience. That server is usually making $2.13 per hour and relies on those tips to pay rent, utilities, vacations, childcare, etc.

Many of us have a bonus structure in our jobs and earn extra money for hitting certain goals or doing a job well. Imagine if your normal $80k annual salary was reduced to $25k, but you had bonus incentives if you worked hard and met goals. Many of you wouldn’t even think about it, right? Servers are working for tips the same way you’re working for your check – it’s your livelihood. And you wouldn’t turn down a bonus by saying, “no thank you, I’m just doing my job.”

Exactly. Don’t ask a server to do the same. They do their jobs well and use the tips (bonuses) to live. A gentleman doesn’t wrestle with giving a tip or not…he’s a gentleman and he values what others are and do. A gentleman tips (quite handsomely most often, but that’s up to you).

5. Remember, social media never turns off.

Do I have your attention now? We’ve all seen those posts on Facebook and the news that detail a server getting stiffed on a $100 tab, often including some judgmental comment in place of a tip on the receipt. This kind of publicity lives on forever in cyber space. When you’re less than gentlemanly out at the local watering hole, and you decide to leave a comment instead of a tip, you’re asking to become internet-famous… and for all the wrong reasons.

More often than not, you will be spoken about very kindly and remembered for next time when you tip well and are friendly. One time I went to dinner with my friend Megan and paid with a credit card. I wrote “CASH” in the tip line (tip: this is a server’s best friend. Cash tips are always best). I had full intentions of leaving cash, but Megan and I were laughing and talking and got distracted… and left.

I got home and was mortified. This is not me. This is not who I am. I am not that guy. What a dick move. For shame, Blake. You need to make this right.

I called the restaurant and explained my mistake. The server had left for the night, but I said I would be in tomorrow to make up for it. I drove in for lunch and personally handed her double what I was going to tip the night before as my own personal apology. From that point forward, I was remembered and almost always given complimentary items off the menu.

When you make a good impression, it follows you. When you make a bad impressions, it follows you.

So remember, gentlemen, you are being waited on by another person. Yes, he or she is paid to do so, but it’s less than $3 an hour. Be courteous, be friendly, be generous, and be a gentleman. It will only help your legacy when you leave.

Bonus – Here’s what many suggest for tipping places and amounts:


What do you think about tipping? Do you fancy yourself a “good” tipper?
What do you think of the new cohost Oscar? 
Should we keep him or send him packing?
Let us know! And remember to SUBSCRIBE to the podcast!

Previous post

The Best Belt You'll Ever Own

Next post

Master Your Email Etiquette with These 7 Easy Steps

The Author

Blake Hammerton

Blake Hammerton

Blake Hammerton is the founder and coach at The Sharp Gentleman, and helps men earn more respect while gaining confidence in who they are. He is a certified relationship coach and loves writing about men's fashion, style, character-building, relationships, travel, adventure, and more.