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Lesson 2: Always Ask

  • Bowtieguy
  • Jun 23, 2017
  • 4 min read

This is a lesson I learned on my US Road Trip and then applied on my European Train Trip. I also think about this lesson every day. It has opened countless doors for me and surprised me each time with the results.

When I was on my US Road Trip, initially, my goal was not to earn my way around the country. In fact, I had been a saver since I was in 1st grade and I was really to spend my well-earned money. I had been a paper boy for seven years and had countless other business ventures as a child. So I planned every expense of this trip and budgeted $10,000. However, just days after starting the trip, when my entrepreneurial spirit kicked in, I learned about the power of asking. I developed a one-minute pitch that told people what I was doing and asked for their support.

Not long after coming up with the pitch (and revising it at least 30 times), I began to receive free food from restaurants, farmers markets, and locals. I had to tailor each speech to its audience, show my enthusiasm and connect with the person to whom I was speaking. Sometimes getting ahold of the right person to talk to was the key to getting a yes, and it was surely the hardest part.

I continued to revise my pitch and began to use it for museums and attractions. I said to myself if these YouTubers and blogger who I read about and watch all the time can do it, why can’t I? After the first three weeks, the only thing I was paying for was gas. Still, I was only asking for what I would consider small things (valued at under $20) in most situations. It was only when I arrived in Santa Cruz that I truly realized the power of asking when I pitched myself for something worth $120. Here is that story.

I had told myself before arriving in California that one of the things I wanted to try was surfing. Then, I found out that one surf lesson cost about $120, which was much more than I wanted to pay. I felt defeated. That is until I thought about my pitch. I kept telling myself it would never work. Surely, they wouldn’t give me something that costs $120 for free. I thought about it hard and asked myself, “What is the worst that could happen if I asked?” They would just say no, right? I did not have to fear legal action or being embarrassed, besides, who knows if I would ever meet these people again. The only two possible results would be yes or no. So I tried it.

I went to a surf school, and I spoke to an employee who told me that the manager was out. She informed me that when he returned he would ask on my behalf and then call me back. From experience, I knew that was a bad sign. When asking for something for free, your goal is to personally make the pitch to the person in power. First, a face-to-face interaction means that the words coming out of one's mouth now represent who they are as an individual. This leads people to want to say and do more favorable things (if you want to know more I suggest taking a psych course or two). Also, it allows the other party to interpret body language and feel your energy. Most importantly it allows you to connect one on one with the other party by reshaping your pitch and conversation to align with what the other party cares most about. Only by being there in person can you effectively and accurately diagnose the situation. On the other hand, playing a game of Telephone often ends with dissatisfying results.

To pass the time, I went off to a local art museum, The Museum of Art and History (I totally recommend it). Unfortunately, I could not stop thinking about the surf lesson. My mind was racing with the possible scenarios, and they all ended with some form of no, which seemed devastating at the time. The funny thing is that if the answer were no, I would not be hurt or changed in any negative way. I would be just fine, even if I didn’t learn to surf.

One hour later the phone rang. I picked it up, and you know what happened next? They said YES! I was going to get a free surf lesson. I raced back to the beach and took advantage of their generous offer. It was the craziest thing ever! I successfully learned to surf after just one hour. Before that day I thought that surfing was something only other pro athletes tried. I do not know why but I thought that you had to be good at other sports as a gateway requirement to trying out surfing. The feeling that you get when you stand up on the board, successfully hold your balance and feel the wind across your body is inexplicable. It is a perfect metaphor for how it feels to have worked so hard on developing a pitch, refining it and then executing it with success!

If you would like to develop a pitch of your own, whether for travel or for another goal of yours, I have included the elements of a pitch and tips for a successful pitch below. If you want a more interactive and visual explanation you can go to my YouTube channel (Luke Makris) where I posted a video explaining this. The video is titled, “How to Form a Successful Sales Pitch for Travel.”

ELEMENTS OF “THE PITCH”

  1. Introduce yourself

  2. Tell them what you are doing

  3. Provide yourself with credibility

  4. Tell them what you will do for them

  5. Ask for exactly what you want (don’t hold back)

TIPS FOR DELIVERING A SUCCEFUL PITCH

  • Make every effort to speak to the highest seniority person, or second best, the marketing head

  • State your name and alias on social media if it is different

  • Firm handshake

  • Eye contact

  • SMILE

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