Get Free Drinks, Upgrades And Smiles When You Travel


A version of this article previously appeared Forbes.

A very good friend of mine has heard me tell many a tale of trips in which I have scored free drinks, gratis hotel and car rental upgrades and various travel freebies. However, without experiencing my stories first hand, he always suspected there was a degree of embellishment involved to make my stories a bit more entertaining.

We recently had the opportunity to travel to Hawaii together and I was able to show demonstrate the power of a little respect and an authentic smile.

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It’s Kool To Be Kind

We began our trip sitting in the dreary, uncomfortable airport terminal, with ample time before our flight. Bored, I explored the terminal and located the airline’s club lounge. Despite not being a member, I entered and immediately knew where I was going to spend the next couple of hours. Sitting behind the receptionist desk, in a chair that was two sizes too small for him was, Don, a large Hawaiian with a hearty smile. He was clearly bored with the paperback book in his oversized hands and he seemed open to chatting.

After some brief pleasantries, I asked him what it cost to join the club and if they offered a one-day pass. He laughed and apologetically said, “It’s something like $500 a year. We don’t have day rates, but I can let you slide this time if you just want to check it out.” I thanked him and hurried back to grab my buddy.

After a leisurely time in the airline club, we boarded our flight and met Kelly, a young surfer dude in his early twenties who was our attendant for the next five hours. Once everyone was settled in their seats, I asked him where he lived in Hawaii, where he surfed, what sort of board he used, etc.

As soon as we were airborne, I asked Kelly if he could hook me up with a Mai Tai. He laughed and asked if I wanted one of his “special creations.” My reply, without hesitation, “Why of course.”

He returned and waited for me to sample the drink. I took a large swallow and sincerely told him, “You are an artist. You should call this ‘Kelly’s Creation.” I had several more of Kelly’s Creations before we landed, all at no charge.

We bid Kelly farewell, hoping we’d see him again on our return flight and headed toward the car rental agency. It was very hot and the woman at the counter did not look happy.

I approached her with a broad smile and asked how her day was going. She replied, “It’s about to get worse. All the flights from the mainland are landing.” She clearly wasn’t happy.

After a bit of joking around, she begrudgingly grinned and eventually was laughing at my corny humor. She waived the fee for my friend to be an authorized driver she gave us a gratis upgrade to a slightly nicer vehicle.

So What

Entrepreneurs are likewise well served to seek out and cultivate transitory relationships with service employees whom self-important professionals generally overlook, such as: waitresses, car rental agents, flight attendants and call-center agents.

Such folks encounter a horde of unhappy, disgruntled and downright surly travelers each and every day. Thus, it is easy to differentiate yourself by simply smiling and showing these hard-working people the courtesy they deserve. Greeting someone by genuinely asking, “Wow. How can you look so cool under pressure when you are so busy?” will often be rewarded with a Bro deal.

Landing A Bro Deal

Identifying and closing a Bro Deal involves three simple steps.

Open The Door – You must make an authentic connection with your potential Bro. Always start with a friendly, sincere smile. Then engage your would-be Bro as a peer, a courtesy they may seldom experience from most of their harried, self-absorbed customers.

The specifics of what you say will depend on the situation. Irrespective, it should be a genuine expression of interest. For instance, after a long day of travel, I approached the night clerk at a hotel at about 1:00 in the morning. He was clearly studying a textbook. I immediately respected the fact that he had a night job while attending college. Rather than ignoring his book or asking him a superficial question like, “What’s your major” or “Where do you go to school?” I asked him, “What are your dreams once you graduate?” He hesitated, clearly debating if he should give me a thoughtful, honest answer or if he should remain in transaction mode and give me a cursory, glib reply.

He opted for honesty and told me that he wanted to someday open a veterinary clinic because he loved animals. We had a pleasant conversation, I was given a free upgrade without even asking and we parted with me sincerely wishing him the best. I didn’t even realized he had upgraded me until I arrived in my multi-room suite.

Obviously, the more unique, appropriately personal and clever your remarks, the faster and wider the door will open.

Make A Connection – Once the door is open, make a connection by finding a point of commonality. By politely probing, you should be able to identify a city, college, country, occupation, sports team, author, musical artist, etc. that you and your Bro have in common. Such similarities lead to liking and liking ensures that your Bro will relate to you as a kindred soul, rather than another anonymous customer.

I recently rented some kayaks on a beach in Southern California. Within three minutes of chatting with my Kayak Bro, I learned that: (i) he previously lived within a few blocks of me on the same street in Philadelphia, (ii) his brother went to my Alma Matta, and (iii) he currently attends the University where I teach.

After I had opened the door and made a solid connection, I asked him if he could give me a “Local’s Only” discount. Without hesitating, he gladly knocked 20% off the price.

Ask For A Deal – Once you establish a personal connection with your Bro, ask them for a deal. If you handled steps one and two appropriately, giving you a deal will be a natural byproduct of your camaraderie.

Bro Deal Tips

Not every situation is conducive to cutting a Bro deal and not every person you meet is a potential Bro. Below are considerations that will significantly enhance your Bro deal success rate.

Time And Place – Avoid attempting to cut a Bro in hectic situations in which you cannot properly make a connection with your potential Bro. If there is no connection, there will be no deal.

Out Of Earshot – Even if you establish a solid connection, do not ask for a Bro deal if your Bro’s boss or other customers are within earshot. Not only is it simply bad form, it will also decrease your chances of getting a deal. If there are a line of customers behind you, be cool and lower your voice when you ask for a deal.

Bending vs. Breaking – Bending the rules to get a free upgrade is one thing. Breaking the rules is something else altogether. Only request things which are relatively inexpensive and will not put your Bro’s job in jeopardy.

Be Realistic – No matter how much you Bro-up with someone, there is a limit as to what they can do for you. Use a liberal dose of common sense as you assess each potential Bro situation.

For instance, it is easier for a flight attendant to provide coach passengers free drinks when the plane has a First Class cabin, as the tracking of beverages is more difficult on such flights. The absence of a First Class cabin on a commuter planes generally takes free drinks off the Bro menu.

Timing Is Everything – Do not rush the Bro relationship. Even though your entire interaction may only encompass a few minutes, if you become too familiar too quickly, you will greatly decrease your chances of success.

Let your potential Bro set the tempo. If your displays of respect and kindness are well received, great. If they are ignored or rejected, keep smiling, but stop pounding on the Bro door.

The Real Reward

If you are rolling your eyes and wondering why anyone would bother asking for such petty deals, I will let you in on a secret – the real reward is not saving a few shekels.

The foundation upon which Bro Deals are built is the levity and personal connection infused into otherwise tedious situations. Traveling becomes less mundane and a lot more joyful when you create a genuine rapport with the folks you meet along the way. The small, tangible freebies that sometimes result from such interactions are a nice bonus, but the real payoff is making brief, yet meaningful connections with otherwise anonymous people who share this planet with you.

Follow John’s startup-oriented Twitter feed here: @johngreathouse.

Image: Photo by Eric Charbonneau/Invision for Twentieth Century Fox/AP Images

John Greathouse

John Greathouse is a Partner at Rincon Venture Partners, a venture capital firm investing in early stage, web-based businesses. Previously, John co-founded RevUpNet, a performance-based online marketing agency sold to Coull. During the prior twenty years, he held senior executive positions with several successful startups, spearheading transactions that generated more than $350 million of shareholder value, including an IPO and a multi-hundred-million-dollar acquisition.

John is a CPA and holds an M.B.A. from the Wharton School. He is a member of the University of California at Santa Barbara’s Faculty where he teaches several entrepreneurial courses.

Note: All of my advice in this blog is that of a layman. I am not a lawyer and I never played one on TV. You should always assess the veracity of any third-party advice that might have far-reaching implications (be it legal, accounting, personnel, tax or otherwise) with your trusted professional of choice.

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