November 8, 2025 | Read online
I’m writing this on Friday last week for the newsletter this week because I already had scheduled last week’s newsletter to go out but I had to get this experience down on paper while it was fresh in my head.
The shit I went through last Friday is an example of me living the Make it Happen mentality, albeit extremely painfully.
I’ll try to make it brief and pull out whatever learning lessons I can along the way but buckle up, this one's a doozy. It also ends with a heavy dose of perspective.
Last Thursday I had a meeting in NYC with a potential partner. I was meeting with the CEO, CRO and the Head of Brand and Marketing of a unicorn company so it was kind of a big deal.
We were meeting at their office downtown at 4:00 and then had dinner scheduled for 5:30.
I booked the 10am flight from BOS to LGA on AA which usually has a flight every hour.
Lesson 1: ALWAYS book the earliest flight out. They are the least delayed.
The flight was delayed an hour, then we sat on the tarmac for another hour. This is when it dawned on me that the weather was supposed to be terrible up the east coast on Thursday and Friday and the Government shutdown was in full effect with air traffic controllers missing their first paycheck that week.
Lession2: I probably shouldn’t have COMPLETELY unplugged from the news over a month ago.
Laguardia grounded all flights for a while so our plane went back to the gate and they allowed whoever wanted to get off. I looked at the weather map and saw it was only getting worse in NYC so I made the strategic call to rent a car and make the (typically) 4 hour drive from Boston to New York.
By the time I got in the car the ETA said 4:00 and one of my true joys in life is beating Waze’s estimated arrival time so I thought I had a chance.
And then the heavens opened up. There were parts of the drive where I couldn't see 2 cars ahead of me because it was raining so hard. As I got closer to NY the streets were flooded and multiple times 3 lanes converged to one as we drove through waist deep water.
The ETA kept getting later and later so I was updating the partner along the way and we made the call to just meet at dinner.
Previously, when I scheduled the flights, I left myself plenty of time to do more research on the partner’s business and better prepare for the meeting. With my drive, I didn’t have the chance to review any of my notes, but I had four podcasts saved in a playlist featuring the CEO discussing various aspects of the business, including its history, strategy, goals, and priorities. I listened to all 4 of them on the ride which was better than any documents or articles I might have found on them.
Then, I opened up ChatGPT on my phone, found the thread I had been using to prepare for the meeting with all the research, turned on the microphone and talked to her. I asked her questions on their financials, strategy, background, and details of the execs I was meeting with, and more. I even ran through a few scenarios and role plays based on some of the goals I had for the meeting.
Lesson 3: If you’re not using ChatGPT like this you’re falling behind. It’s a super power when you’re curious and you use it the right way.
I finally got to the restaurant in time for the reservation at 5:30, albeit a little frazzled but well prepared.
We dove right into some rapport building with the trials and tribulations of my voyage as we took a seat in the back of the restaurant where it was a lot quieter.
I won’t go into the details of the meeting but let’s just say, you can’t have that type of meeting over Zoom.
Lesson 4: Whenever you can get face-to-face with a prospect/partner/customer you should.
After the meeting, we parted ways. I debated on whether or not to get a hotel room and stay in the city or head home that night. It was 8:00pm, it had stopped raining and I wanted to get home to see my family, so I decided to suck it up and make the 4 hour ride home in the dark.
About an hour into the side the heavens opened up again. About 30 minutes later the “low tire pressure” alert went off for the back passenger tire.
It was getting worse so I knew and had to get to an exit as soon as possible. Thankfully, there was an exit less than a mile up with a gas station right off the highway.
I pulled up to the air compressor, hoping the tire was just low and I could fill it up and be on my way. As I got out of the car in the rain and heard the hissing that no one wants to hear.
I pulled the car under the awning and went to the trunk to see what we had for a spare in this rental. I haven’t replaced a tire in over 20 years at this point but thankfully, it’s not that hard to remember.
Lesson 5: If you haven’t done it already, please learn how to change a tire.
It’s now 11:00pm, pouring rain and I need to get this done. I take out the jack, pump up the car, bring down the spare and grab the wrench to take the lugnuts off.
I knocked the lugnuts into the air and yelled “ohhhh.fuuuuudge” and they fell into the snow.
Just kidding. If you don’t know that reference then I’m worried for your childhood.
There was a problem however. It was a Volkswagon and the lugnuts didn’t look like typical lugnuts. They had a black female star versus the typical male hexagon. (if you don’t know what that means, pick up a hammer every once in a while). Here’s what they looked like:
I tried using the tire iron, but it didn’t even come close to fitting into where the lugnuts were. After tearing the trunk and car apart and even using ChatGPT to help me figure it out, I gave up and called for 24-hour roadside assistance.
Lesson 6: I use ChatGPT all the time to figure out stuff I don’t know by taking a picture of whatever it is and asking for help.
An hour later, a tow truck showed up. He couldn’t figure out the lugnut situation either which meant we had to tow the car back to his garage 45 minutes away. It’s now midnight and I need to find a place to sleep.
I asked if he could drop me off at a hotel close to the garage and he agreed, so we jumped in the cab of the tow truck and got ready to head back out into the rain. It’s now 1:00am.
He was a cool dude but looked about as miserable as I was and smelled even worse.
As we were getting ready to leave he got a call from dispatch. All I hear is him sighing and begrudgingly agreeing to what he obviously does not want to do.
He then informed me that we need to go on an adventure to find (2) ten-gallon fuel tanks, fill them with diesel and bring them to a truck on the side of the highway on the way back.
You can’t make this shit up.
What am I going to say? No? Fuck you. Bring me to my warm hotel and drop me off?
Lesson 6: Know your role and who has the leverage in every situation and act accordingly.
So off we went into the darkness, searching for gas tanks and diesel at 1:30am in the middle of nowhere, Connecticut in the pouring rain.
At this point, I had given up any hope of sleeping or this being over any time soon so I just accepted it and made small talk with my new friend and laughed about how miserable we both were.
After about 45 minutes of searching, he got a call from dispatch that the truck had cancelled the request so we headed to my hotel.
The “Quality” Inn was the closest to the garage and right next to the highway so it was the winner of all the “quality” establishments in the area. I had called ahead to reserve the room even though I’m fairly confident they had more than a few vacancies.
I checked in at 2:30 and noticed a large sign that said “THIS IS A 100% NON-SMOKING FACILITY” which I’m always a fan/yet skeptic of.
My skepticism was confirmed as I opened the door to my “luxury room” and was welcomed with the aroma of a stale ash tray. One of my favorite scents.
My room was facing the highway so the buzz of the trucks whizzing didn’t exactly help soothe me to sleep.
I pulled the cover sheet to the bed back and laid down in my clothes, praying there were no bedbugs that would add to my misery.
I passed out and must have gotten a solid 2-3 hours of sleep before being woken up by someone yelling outside my door for their partner to “HURRY UP!!!!”
After taking an oh-so-refreshing shower that definitely wasn’t moldy, I headed out to grab a gourmet breakfast sandwich at the gas station deli-mart next door.
From there I headed to the garage to see if they could get the tires off the car so I could head back home.
I found out they were able to get them off… easily…
Apparently, the little black stars on top of the lugnuts were just covers for the lugnuts, and this little stupid metal hook was the thing you needed to take them off to get to the lugnut with the tire iron.
Do you know how close I was to figuring that out that night before? I had that stupid hook in my hand, put it into the black star and tried to move it around but it wouldn't hook on anything. Apparently I needed to go about a centimeter deeper (I'd insert a joke here but I don’t want to offend anyone. If you know you know.)
That centimeter cost me $100 hotel room, $650 tow fee and about 10 hours of pure misery.
With my pride barely intact, I took my keys and started off on the remaining 2 hour ride home.
That all sounds horrible, right? It was. But life sometimes has a not-so-funny way of putting things into perspective.
As I was driving home, marveling at how shitty the past 24 hours had been for me, I got a call from my cousin who gave me some news about another family member that made what I had been through sound like a vacation.
I’ll spare you the details but let’s just say it's the type of news that no one ever wants to get.
The rest of my ride home was filled with sadness, reflection, gratitude and more sadness.
It made me remember that even my worst day is better than what many others are dealing with on a regular basis.
I don’t want to end this newsletter on a bad note so I’ll say what I always say at the end of all my podcasts:
PLEASE - go out there and make someone smile today because no matter how bad your day is going or how bad you think it went, if you make someone smile you know you had a good day, and the world needs A LOT more of that right now.
#MakePositivityHappen
SPOTLIGHT: Otter.ai
Remember how I was listening to the podcasts and talking to my GPT to help prep for the meeting? One of the tools I used to do that was Otter.ai
If you want to learn about the different techniques and processes to proactively handle objections, and see how I use Otter to help role play objection handling scenarios, you’re going to want to join my next Free Training Thursday on November 20th at 12:00pm EST.
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