This ridiculous picture is of me yesterday afternoon after spending 3 hours riding an 800lb motorcycle around and around in my driveway by myself in 90 degree Florida heat.

But that pic is the end of the story not the beginning.

It all started when I went to Mexico a couple years ago with some business buddies. We spent the week with a guy named Guillermo Sauza. His family started the Sauza Tequila company many generations ago. Guillermo owns Fortaleza Tequila which is arguably the best Tequila in the world.

Guillermo is literally the guy that they created the avatar for the “Most Interesting Man in the World” ad campaign for DosXX beer. He has been on the cover of the Wall Street Journal. Walks around town with a 45 Calber Pistol in a holster on his hip… And has an 80 acre compound in town on a hill looking over Tequila Mexico… Sorta like a King or the head of a Cartel would.

We get to hang out with this guy for the week because a buddy in the group is a made man in the hospitality world. Sean Finter knows everybody. Everybody loves him. He likes to introduce guys like us to guys like Guillermo. Our worlds could not be farther apart.

Guillermo lives in Jalisco Mexico less than an hour away from Guadelajara where Felix Guallardo birthed the Mexican Cartel 30 years ago. At the time, I was living in a family friendly subdivision a couple blocks from the beach in Newport Beach California.

During the trip, we had street tacos and watched the NFL in Guillermo’s CAVE. Yep his man cave is a literal cave.

We got to drive through town at night and wonder if we were going to get killed. Had drinks at some famous place with a 94 year old bartender where the locals were throwing popits at us letting us know that the gringos were not welcome there.

It was a helluva experience.

One of the coolest things we did during the week was visit a place called Hacienda El Carmen. Look it up. It is amazing.

H.E.C. is a 500 year old Mexican Hacienda turned into a resort-ish type place in the mountains of Mexico in the middle of nowhere. But it is one of the most beautiful places I have spent a day in my life. Truly amazing.

But the point of this long story is not the Hacienda. It was the 1 hour roadtrip to it that changed things for me.

See… the morning of the trip… Guillermo comes out and says…

“I’m gonna ride my Harley. I also have Harleys for anybody else who wants to ride up with me…”

(That’s Guillermo on the left)

Sean… the guy on the right who brought us there is a big Harley rider. And surprisingly to me… my buddy Rob Kosberg hopped right in and knew how to ride a Harley as well… that’s him on the 2017 FatBoy in the middle.

I got the privilege of riding up in a honda SUV with Guillermo’s 28 year old girlfriend and two other non-Harley riding pusscakes like me who will remain nameless.

I felt like I was missing out on something special. I had never ridden a motorcycle in my life because we had a family tragedy when I was a kid… my father owned a motorcycle… but his sister (my aunt) got killed on one when an old lady ran a stoplight and hit them circa 1980 or so.

My dad sold his bike and it just wasn’t a thing for us.

But now… I felt like I was missing out.

After they rode together, Guillermo gave Rob and Sean this amazing t-shirt with an agave scull and bones thing that he had made just for people who rode Harleys with him. Now I really felt like an outsider.

They had this experience within the experience that I couldn’t participate in. I didn’t let on that much at the time but I was really bummed I didn’t know how to ride a bike and go with them.

The rest of the trip was great and we got back from Mexico in one piece about a month or two before the plandemic hit.

When I got back, we went into full focus mode to get out of California. So we spent the next 6 months getting our stuff together and sold and moved from Newport Beach to St Augustine FL mid June 2020.

The desire to maybe start riding a motorcycle was still there but had been pre-empted by our 4th cross country move in my lifetime.

I would have never bought a bike in SoCal. The traffic is too crazy there.

But here in Florida… it didn’t feel so daunting. So I started looking.

On October 1st I bought myself a Harley. A 2017 Heritage Softail. Beautiful bike. It just spoke to me and I had to have it. I asked the guy at the dealership if it was a good bike to learn on… he said “SURE!”

He lied.

That bike weighs nearly 800lbs. It is not the right bike to learn on. Especially if I actually want to take care of it and not beat it to death in the process of dropping it and all the mistakes one makes as they try to ride for the very first time.

It sat in my garage for a month. I would go out and crank it up everyday. It sounded amazing! I posted pictures of it on Instagram and FB and people congratulated me on a beautiful bike. But I was too scared to ride it.

I bought all the gear. Two $500 helmets. $500 jackets. $300 Kevlar blue jeans. $500 boots. Gloves. Goggles. More jackets. Another pair of boots.

I signed up for the motorcycle endorsement class that was given jointly by the state of Florida and Harley Davidson.

The class was 3 days. One night session and two all day riding sessions. The night session was the “book test”. I aced it. Teachers pet. Curious. Asking dumb questions. Just totally excited.

Next day… first riding day. Was broken into steps. There were 9 steps to getting your motorcycle endorsement.

Step1: Knowing the bike. This is the step where you tell where the signals are… crank it up. Check oil levels. All the pre-riding stuff. There were nice little acronyms like T-CLOCS. Aced it again.

Step2: Duck walking. This was the first time I had ever sat on a moving motorcycle. Ever. Like the very first time. We had a 50 yard course. An orange cone on each end that denoted my particular lane (there were 8 of us). And i did it. We duck walked 3 times across and 3 times back.

The thing nobody had told me was that the way you turn around a motorcycle manually is pretty tiring. We had to turn the handlebars hard right… then walk it to the point of perpendicular to the course then turn the bars hard left and do a semi-circle back to the left to get fully turned around.

Doing that 6 times was a bit tiring in all the gear I was wearing. At this point, it probably makes sense to describe the scene a little more. In my class, there are 7 others besides me.

There are two dudes about my age who apparently have been riding motorcycles for 30 years each but never got their endorsements and decided to get “legal”.

A lady a bit older than me who moved from Louisiana and wanted to get her endorsement. She had been riding sport bikes for 40 years she said.

And 4 young limber cocky dudes.

Here I was in full Harley gear. Literally wearing almost $2k worth of shit.

One of the young dudes was in sweatpants and reebok velcro hightops.

I looked like Lloyd and Harry from Dumb and Dumber after they found the money in the briefcase.

Now we move on.

Step3: Feet on Pegs.
In this step, we are supposed to put our feet up on the pegs for the first time in crossing the 50 yard course. Now, it’s important to know that the bike we were riding was the Street500. The smallest bike in the Harley line. They had everybody test on this bike so that men and women could ride it in the class.

I started across. Duckwalking fine. Went to pull my feet up on the pegs and my $300 Kevlar jeans got hung on the peg. WTF.

Let’s try again. I went back and forth 6 times. Failing every time. Getting more and more frustrated. More and more tired. Sweating in all that damn gear I was wearing.

All the other students were done after 6 runs across. But Coach Jimmy kept working with me… alone… in the middle of the course. While everybody watched me fail. The teachers pet. Completely exposed. Like a raw nerve. I could not get my feet up on the pegs.

So Coach Jimmy told us all to take a break. Have reflection time in our riding Journal and get together and talk about the experience so far. I wrote “Fuck this” in my journal. I had no words for the group.

Then Coach Jimmy was like… ok guys… on to Step4.

I was like hey Coach Jimmy… I assume that this class builds on the skills learned in the last section right?

Yep.

Well I don’t know if you noticed… but… ugh.

I bowed out of the class. Made the walk of shame back to my 4 wheeled vehicle and drove home. When I got home I messaged my wife and RobK who both ridiculed me. They thought I was joking. I mean only a loser could fail the motorcycle endorsement class right?

Well I certainly felt like a loser.

I licked my wounds. This was a pretty spectacular failure for me.

It was December. It had been a few weeks since my class. I was at a crossroads… at this point all the memories of Mexico had faded away and the only memories vivid in my head were the ones of the stupid kevlar pants getting hung on the pegs.

But I had a decision to make.

At this point it would have been easy to sell the Heritage and move on. Believe me I thought a lot about that.

But what kind of example would that be to my kids? Try something… don’t succeed right away… quit. That isn’t what I want to teach them. So I made the decision to keep trying. I just needed a new approach.

I figured that I needed a practice bike like the one in the class.

So I bought a Triumph Bonneville T100.

I got it home with the help of a friend. Now I had 2 bikes in the garage.

I went out there and started sitting on it and cranking it and using the friction zone on the clutch to slowly move forward and roll it back into place. I felt like I was making progress.

Then I forgot to put the kickstand down and the bike fell on top of me… in the garage… and I was pinned under the 400lb bike because my shoe was pinned by the peg in a weird way.

So I started yelling for my wife (Dawn) to come help me out. When she got out there all she could do is laugh and ran to get her phone because she wanted a picture. 

Luckily my son Wylie was above childish humor and saved me. The gear lever was bent. I had to buy a new one on ebay and install it a few weeks later when it arrived.

Just one more indignity stacking up in this quest to ride. And I torqued my knee a bit.

So my buddy Rob Kosberg came up to give me some riding lessons on my new Triumph one day… we go to an empty culdesac in our neighborhood and I actually got my feet up on the pegs.

I was doing small slow doughnuts around the culdesac until it was time to stop… my boot got hung on the peg and I dropped the bike. The clutch lever was bent.

Rob said we could bend it back and proceeded to break it off.

So I ordered a clutch lever from ebay and installed it a few weeks later when it arrived.

During this time, I got to thinking. There are two problems with this new bike I had… the triumph.

Problem number one is the fact that it has a different riding profile to the Harleys… the Harley is a sit back and feet forward riding style. The Triumph is more of a lean forward and feet mid to back riding style.

Something you would see a skinny euro dude riding maybe. Or a hip anime asian female with pastel helmet et al.

Not a 49 year old dude with a bit of a belly.

The second problem was that I was learning 5 things at once. The gear shifter with my left foot. The back break with my right foot. The clutch lever and friction zone with my left hand. The front brake and throttle with my right hand.

…and how to balance and not fall down.

Which at 49 years old is a bit more treacherous than it is at 18. The prospect of multiple falls while learning all these skills wasn’t super appealing.

So… I decided to buy my third motorcycle. A 2016 Harley Davidson Freewheeler Trike.

This was a great purchase.

I took the 3 wheel motorcycle endorsement class and passed.

I got the trike and didn’t have to worry about falling off. I started riding around the block. Then around the neighborhood. Then out to the publix. Then the gas station. Then eventually I took it on the road for the first time. Then I started riding farther and faster.

I put 1000 miles on the Trike in 2 months. I got proficient with the throttle and clutch and hand and foot brakes.

I got to the point where I felt like i could ride a little bit. I took the trike to Daytona Beach for cigars one trip and then later for bike week with Rob Kosberg. We spent the day down there riding around. It was fun.

I feel like a rider.

But also a bit NOT like a rider since most of the guys on trikes are 20 years my senior…. and the guy with the trike in Sons of Anarchy was Piney – the old guy who had it fitted to also hold his oxygen tank.

But it served a purpose. I feel very comfortable with the controls now.

So… I decided the only way I was gonna get comfortable riding a two wheeler was to get YET ANOTHER BIKE.

So a few weeks ago… I bought my 4th bike.

It’s a 2000 Victory Hammer that has the exact riding profile of my Heritage Classic. I paid $2500 for this bike. It looks pretty cool but is really a beater. If I drop it… who cares. It is a cheap bike perfect for learning on. 

I don’t have to protect it like I would the Heritage. It has the riding profile I need unlike the Triumph. It is a two wheeler unlike the Trike. 

I bought it and got it home. It has rained on and off for the last two weeks so it has sat in the driveway… getting wet. There is no more room in the garage. So it has to sleep outside. 

But yesterday was a beautiful sunny 90 degree day. I was done with my work early. So I decided to start trying to ride my bike on my own. 

I took all the cars out of the driveway. 

Then started going back and forth from the house to the street. Without anybody else there. Just me and the bike. Duckwalking. 

After about 3 hours… I started putting my feet up. 

By the end of the day… I was getting my feet up on the boards every time. Without falling. Without Rob’s help or watchful eye. 

I did it. I got both feet up. On the pegs(boards). It felt good. 

I told my wife… after I came in… It only took 9 months for me to get through Step3. 

Of course I know that I am not a rider yet. But it felt like a big step. And I feel like there are many lessons for me and others throughout this journey. 

Here is what I have learned. 

1.  My 14 year old Son was the first one to congratulate me on getting up on the bike and sticking with it for all this time. He is paying attention. 

2. If feels good to conquer something like fear in your late 40’s. The first dozen or so times I rode the trike on the main roads I was pretty scared. It is not a natural thing. 

3. Learning to master a new skill like this is exactly the same process it takes to make your funnel or ads or business work. You are going to have obstacle after obstacle come up in your face. You get to choose whether to quit or keep adapting. Keep trying new things. Getting small wins. This is the business game we play. It is what makes business interesting and fun and challenging. 

4. I am having to work on myself to make this possible. My hip flexors are too inflexible. I have been doing stretching every day to be able to ride. This is the person I have to become to do the thing I want to do. It is this way with most things. You have to become a different person to add to your life. 

5. As much as it is helpful to have a friend or mentor or coach helping you… it will never “take” until you get out in your driveway by yourself and sweat for 3.5 hours straight in the 90 degree heat and get it done. The most important work is always alone. 

6. Don’t listen to the naysayers. I had quite a few people ask me if I was having a mid-life crisis. But all I was doing was iterating how I was going to acquire this skill in a somewhat safe manner for me. I was working through the process. 

7. The way it works. Solve a problem. Discover a problem. Solve that problem. Discover the next problem. Until you reach the end result. 

I am sure there are more lessons. But the biggest takeaway is the metaphor that this journey and struggle has 

been for my business life. It is the same. It really does take this type of hard work and dogged determination to make a business work. Most people are not willing to embarrass themselves.

Most people aren’t willing to keep trying. Buy 4 bikes when even their wives are making fun of them lol.

Most people also will never ride in the mountains of Mexico with Guillermo Sauza either… but this mofo will.