The Amazing Race to Trump Doral

In 2022 when I originally started this blog, my thought was to document my travels through Europe in a quest to find an olive oil for my brand, Palloncino. 50 Days = 50 Blogs.

But now on a post-olive oil journey, I sit back and ask: why did I really start the blog and what did I really write about?

In October 2022, two days before my initial flight to Madrid, I was in Columbus, Ohio with my parents and some of their friends. Both their friends and my brother’s college friends had found out through the grapevine that I’d be heading to Europe to learn about olive oil.

At the end of every conversation, people gave me the following remarks:

• ‘let me know how you like…’

• ‘send pictures in…’

• ‘let me know how the food is in…’

• ‘keep us informed’

Most of the time, people say any of these without intention of actually hearing how things are, but rather as an expression of interest to make me (or the other party in a given situation) feel good. It’s the right thing to say. We all do it.

This gave me an idea.

I don’t have the time to text my grandparents, brother, parents, my friends, their friends, extended family members, and random interested strangers while traversing the mountains of Kalamata, Greece. But I did want to keep people engaged. This was an ‘Aha’ moment for me — instead of crafting personalized messages, pictures and videos, create 1 message for the people interested in my travels.

And how do I send a message to these people?

A blog. The same one you are reading now.

What I now realize is at the root of it, this blog is not about olive oil, it’s a public facing diary of the quirks and intricacies of my daily life. I’ve moved away from this in recent times and focused more on educating about olive oil — which wasn’t necessarily wrong.

But for this entry I am going back to the core functionality of this blog: 1 raw message for the people interested in my work.

The Belt

My mom LOVES to buy me clothing. Unlike my brother, I am the least grateful recipient of her clothing and am inclined to say NO to everything. The classic interaction is “Jack I bought you a new shirt — do you want it?” I always say — mom, you don’t need to buy me any more clothing. I have enough shirts. She’s gotten smart enough to strategically purchase these items as gifts for my birthday or a holiday — where I am not in proper position to say NO. And every once in a while, I just say yes to move on from the conversation.

In tandem with this low level of gratitude for receiving new clothing, I never buy clothing for myself. I overwear everything in my closet — for example the Seaview Market Fire Island hat. My family has told me to toss it about 50 times this year. It’s easy and matches everything, so why do I need another hat? The stress around making a decision for a new hat that I don’t even want is just not worth it.

But every so often, I do need clothing, and when there’s a need, I actually enjoy the purchasing process. I know exactly what I need, so I can efficiently go into a store (physical or online) of choice, find the color and size, and make a purchase. Easy, right?

Friday, January 3rd, 2025

It’s Day 2 of a Three Day Video Shoot for an Orthodox Jewish Wedding (hired by Birch) at Trump Doral. I’m scheduled to be on the property from 3pm-7pm.

Prior to the shoot, I knew my once-white-now-black pair of Vejas I’ve been rocking since summer 2023 was not going to cut it, so I went to Dick’s Sporting Goods and bought $74 white vans. Great investment. I’m thankful I bought the shoes on Thursday AM as little did I know the wedding itself was Thursday Night! The new shoes made up for my partially wrinkled Amazon Sports Jacket that will never see the light of day again (lesson learned).

So when I wake up Friday morning, I mean to go to LifeTime Fitness Immediately upon waking. However I had to comb through the Day 1 Footage to send to Birch and my desired workout got pushed back to 1pm.

At the conclusion of my workout at 2pm, I open the locker and realized I made a massive mistake: I forgot my belt.

This was not good — even though I’m up 3 pounds on the two-week Miami Trip, my new Lululemon ABC pants can’t hold up on their own. Without a belt, my Fruit-of-the-Loom underwear would be visible in <15 seconds. That would not cut it.

By the time I get to the car, it’s 2:15pm.

45 minutes until shoot time.

Doral is 25 Minutes from Lifetime and I still hadn’t eaten Lunch.

Here’s where I detract from normal people.

Normal person stops to buy a belt and goes straight to Doral. If there’s time, grab a bag of chips or something at the club.

But for me? The Fresh Market is staring at me in the face and telling me, “please Jack, come in and I’ll quench your hunger.”

I listen and proceed to realize the 3 person line for sandwiches was a standstill situation. The issue is the premade sandwiches looked no bueno, and they didn’t have the Mush Overnight Oats I’d been relying on all trip. With a self-imposed 15 seconds to act, I find a California Roll for $9. Done.

I had to tell myself 3 or 4 times on the run to the car to wait until I’m driving to eat that California Roll. Gosh it was so tempting to eat in the parking lot but I successfully waited it out.

Time — 2:21pm

Shoot Time — 3:00pm

Time to Destination: 25 Minutes.

Time to Buy a Belt — 14 Minutes.

This was actually a miscalculation as the self-parking lot was a 12 minute walk from the clubhouse. Or a 4 minute sprint. Over the 3 days on-site, I always picked sprint out of necessity.

After taking roughly 45 seconds to down a 10 piece supermarket California Roll + Ginger, I tried finding suit shops on Apple Maps. Didn’t work, but I quickly came to the conclusion that there will be something that shows up on the side of the road. So many stores in Miami.

There was a place called Ross Dress for Less but in the 2 seconds I had to make the decision, I felt that a big store like that could take too much time to buy a belt. And I wasn’t sure what kind of clothing they carried Pass.

Well, 17 minutes later and now only 8 minutes of route left, I realize my wait and see strategy was not working. My Great Uncle is a member of Doral, but I wasn’t willing to pull the card of asking him for locker and belt access. That crosses the line.

I then think back to that Ross store, do a quick Siri Google Search and realize they carry belts.

Lucky for me, there was a Ross directly en Route to Doral. Phew.

2:47pm I pull directly into the Ross Parking Lot — but Ross was on Floor 2. Ugh.

I proceed to sprint to the nearest staircase and head up to floor 2 to realize this was a service entrance with a locked door. I then go back down the stairs, sprint all the way around the building (very big), and find a staircase that took me up to Floor 2. I continue my sprinting ways up the stairs and I see a Marshall’s and Ross.

I change my 90% sprint to a 70% casual (but not casual) brisk jog. I first venture into Marshalls to see no clothing in sight, so I exit within 6 seconds and now turn the jets back up to 90% towards the entrance of Ross.

Now at a 70% Jog Speed, I am a hawk inside Ross searching for belts. I glance at the checkout line and see 15 people with full shopping carts and 1 poor lady dealing with an angry customer at the register. Uy. That was a later problem though. The priority is to find the belt.

As I shuffle through aisles and casually do spin moves around moms with strollers, I see in the corner of my eye, at the back left corner of the store, a display of discounted leather-looking long things of many colors. 70% turns to 90% and I arrive at the solution to my problem.

Belts!

The Amazing Race was one of my favorite shows growing up, and I treated this experience as I would a leg of an Amazing Race episode.

Set internal timer for 15 seconds — Go.

This is a real thing. I gave myself only 15 seconds to find a size 32 black belt. Quick price check: $13.

It worked. Found in 13 seconds.

I’m sweating bullets through my white shirt and still haven’t changed my shoes to the white vans (which is good b/c my New Balance v5s are better designed for the sprint).

Now I turn the engine all the way up to 95% to get to the line for the register. Ok, I arrived, now I can breathe and wait my turn.

I wait 10 seconds. No movement.

Fuck. I have to cut this line for my belt. 12 people in front of me, 2 of whom know the English Language.

The scenario left me no choice: I had to cut the line. For the person in front of me in line, I proceed to respectfully point towards my belt, put my hands out like I’m begging to get to the front of the line, and one-by-one get the OK to cut all the way to the front of the line.

I have no idea how I pulled it off but GD I wish I always carried that energy while shopping. I rushed through checkout / payment so quick that they never cut off tags, so I had to run back in, disrupt another person at the register to get an Xacto knife to cut through everything. That took 30 seconds, and finally my belt was ready for use. Problem solved.

Down the stairs I go, thinking I took the shortcut to the car.

Nope, the door is roped off. I let out a big ole F-Bomb to the streets of Miami.

However, whoever did the roping did a poor enough job to leave just enough space for a desperate me to squeeze through and make it to the other side. 12 second process total.

95% sprint to the car, and I pull out of my spot, not enough angle, pull out more, exit.

Ok I’m on the road. Exhale.

Time: 2:56pm

Doral ETA: 3:01pm

Clubhouse ETA via Sprint: 3:05pm

Clubhouse ETA via Walk: 3:12pm

I’m late. Not good.

Very fortnuately for me, the navigation budgetted in an extra 2 minutes to navigate the parking lot of Doral. I arrive at 2:59pm and rapidly throw on my new shoes, grab my camera (a Wilson Pickleball Bag for this trip) and drone bag and have caught enough breath to weather a final sprint to the clubhouse.

But in the corner of my eye, I see a guy around my age, wearing a Trump shirt with a nametag, in a golf cart with some food and drink inside. I played dumb and I ask if he was on the way to the clubhouse even though he was clearly going the other way.

He looked at me, looked at his food, looked at me again, and gave the nod.

I sit in his cart and he floors it to the clubhouse. What a guy.

3:01 arrival.

Next time, don’t forget a belt.

-Jack

If you want to see some photos or videos of the event, follow @bircheventdesign on Instagram and check through their stories today. I also reposted these to instagram.com/extravirginguy