🏍️🔥 Episode 40 — Josh @IMRidingPlaces : Bet on Yourself, Buy the Bike, and See What Happens Saarloos and sons – Chopping it up – With Keith Saarloos
Chopping It Up with Keith Saarloos · Released March 28, 2026 · Santa Ynez Valley, California
About this conversation
Josh | Motorcycles, Risk, Freedom, and the Kind of Life You Have to Go Chase
Some people wait until life gives them permission.
Some people buy the motorcycle first.
And every once in a while, somebody decides to stop overthinking it, leave the nest, and find out who they really are out on the open road.
This episode is about freedom.
I sat down with my buddy Josh — aka “I Am Riding Places” — for a conversation about leaving behind a successful chapter, betting on himself, buying a 25-year-old Harley sight unseen in Florida, and riding it solo all the way back to California. Along the way, we got into motorcycles, Americana, fear, risk, purpose, documenting your life, and what happens when you stop asking “what if it goes wrong?” and start asking “what if it goes right?”
Josh spent the better part of a decade riding Harley-Davidsons across the country, documenting small-town America, family legacy, and small business. Then he stepped away from that chapter, gave himself no excuses, and started building something of his own — one mile, one camera roll, and one leap of faith at a time.
This one is about motorcycles.
But it is also about courage.
• 🛣️ Leaving the Nest
Josh talks about stepping away from a great run, knowing when a chapter is over, and taking ownership of what comes next.
• 🏍️ Buying the Bike and Going Anyway
A 25-year-old Harley. Facebook Marketplace. Sight unseen. Florida to California. Solo. Sometimes the best ideas sound a little insane at first.
• 🌎 What the Road Teaches You
From documenting small-town America to meeting people face-to-face, Josh explains what years on a motorcycle taught him about culture, family legacy, and human connection.
• 🔥 Why Risk Matters
No kids. No mortgage. No excuse not to go. This episode gets into the beauty of betting on yourself when life gives you a window to jump.
• 🧠 Underthink It
One of my favorite ideas from this whole conversation: sometimes the way forward is to stop manufacturing fear, quiet the noise, and just go do the thing.
• 🌵 Texas, Wind, Heat, and the Real Ride
Josh shares stories from the road — the wind, the miles, the sunburn, the old-school bike, the screw-down throttle, and the kind of trip that strips life back to basics.
• 📷 Documenting a Life Worth Remembering
Why carrying a camera matters, why the internet can still inspire good things, and why it is worth leaving behind proof that you really lived.
• ⚡ What If It Goes Right?
The whole episode circles around one big idea: fear kills more dreams than failure ever will, and sometimes the only thing left to do is grab the bars and go.
This conversation is about motorcycles.
But deeper than that, it is about becoming.
It is about the version of you at 8 years old.
The version of you at 80.
And whether both of them would be proud of the life you chose to live.
It is about shaking hands.
Making the leap.
Trusting the road.
And realizing the boogeyman is usually a lot smaller than you made him out to be.
This isn’t about playing it safe.
It’s about buying the bike.
Taking the trip.
And coming home changed.
You can find Josh here:
Instagram / YouTube: I Am Riding Places
Creative project: CR8CO.com
And if this one hits you in the chest a little bit, good.
Maybe it means it’s time to go do the thing you’ve been thinking about.
From Keith’s original Valley archive
The following material is preserved from the original episode post. Existing transcript text is an archive copy and may contain transcription errors.
Episode 40: Josh, I Am Riding Places, Motorcycles, Risk, Freedom, and What If It Goes Right?
In Episode 40 of Chopping It Up with Keith Saarloos, Keith sits down with his friend Josh, the motorcycle traveler, photographer, filmmaker, and creator behind I Am Riding Places, for a conversation about Harley-Davidsons, solo travel, risk, freedom, creativity, small-town America, and the kind of life you have to go chase.
This episode is about motorcycles.
But it is also about courage.
Keith and Josh talk about leaving a successful chapter, betting on yourself, buying a 25-year-old Harley-Davidson sight unseen in Florida, and riding it more than 3,000 miles back to California.
The conversation explores what the open road teaches you, why fear kills more dreams than failure ever will, how motorcycles strip life back to the basics, and why the better question is not always “what if it goes wrong?”
Sometimes the better question is:
What if it goes right?
-
Summery
n Episode 40 of Chopping It Up with Keith Saarloos, Keith sits down with Josh, better known online as I Am Riding Places, for a conversation about motorcycles, freedom, risk, creativity, entrepreneurship, friendship, and what happens when a person stops waiting for permission and starts building a life of his own.
I Am Riding Places Instagram:
https://www.instagram.com/imridingplaces/I Am Riding Places YouTube:
https://www.youtube.com/@imridingplacesCR8CO:
https://cr8co.com/The episode begins with Keith introducing Josh as a cowboy in the best sense of the word. Not necessarily because of a horse, a hat, or a saddle, but because of the way he moves through the world: independent, willing to take risk, curious, unafraid of distance, and drawn toward the open road.
Josh explains that for the better part of a decade, he worked an incredible career riding Harley-Davidson motorcycles across the country and documenting small-town America, family legacy, independent businesses, and the people who make the backroads of this country worth seeing.
That chapter was connected to Two Lane Life, where Josh spent years traveling, filming, photographing, creating, and helping tell stories from the road.
Two Lane Life:
https://www.twolanelife.com/Two Lane Life YouTube:
https://www.youtube.com/@TwoLaneLifeHarley-Davidson:
https://www.harley-davidson.com/After about six years, Josh realized it was time for a new chapter. He was 29 years old. No kids. No mortgage. No excuses. He knew that if there was ever a season to take a risk, this was it.
So he stepped away from the safe thing.
He gave his friends notice.
He made sure they were set up.
He left well.And then, three days later, he flew from Los Angeles to Tampa, Florida.
From there, he took an Uber to St. Petersburg, bought a 25-year-old Harley-Davidson from Facebook Marketplace sight unseen, and rode it solo all the way back to Ventura County, California.
More than 3,000 miles.
On an old bike.
Still not registered.
Across the country.
Alone.
Facebook Marketplace:
https://www.facebook.com/marketplace/Tampa, Florida:
https://www.visittampabay.com/St. Petersburg, Florida:
https://www.visitstpeteclearwater.com/Ventura County, California:
https://visitventuraca.com/Keith and Josh pause on that moment because it captures the whole spirit of the episode. There is something deeply American about buying the bike, taking the leap, and riding into the unknown. Keith says that whether someone wears a cowboy hat or not, there is a little cowboy in every American.
The road calls.
The unknown calls.
The part of you that wants to know what you are made of calls.
Josh says the ride from Florida to California was one of the best experiences of his life.
The conversation then turns to what motorcycles teach you.
Keith talks about how every motorcycle trip should change you. If you come home the same person, the trip failed. A motorcycle does not just move your body through space. It puts you inside the weather. Inside the wind. Inside the heat. Inside your own head.
On a motorcycle, your brain has one job first: keep you alive.
Then it starts doing the second job.
It starts untangling the knot.
The worries.
The fear.
The ego.
The excuses.
The overthinking.
The imaginary monsters.
The things you were carrying that maybe you did not need to carry anymore.Zen and the Art of Motorcycle Maintenance:
https://en.wikipedia.org/wiki/Zen_and_the_Art_of_Motorcycle_MaintenanceJosh agrees and talks about what the end of one chapter taught him. He was 23 years old when he first stepped into that world. He had a business degree because he did not know what else he wanted to do. He picked up a camera almost by accident. Then two friends gave him a shot and asked him to help build a YouTube channel.
He did not fully know what he was doing.
But he figured it out.
That decision changed his life.
Photography became a tool.
Motorcycles became a way of seeing the country.
The road became a classroom.Josh says the biggest lessons from those years were culture, family legacy, human connection, and the importance of sitting down with someone, looking them in the eye, and learning where they came from and why.
And also:
Buy a motorcycle.
Keith asks Josh what 29-year-old Josh would tell 23-year-old Josh.
Josh’s answer is simple:
Do it again.
Put your head down.
Work hard.
Treat something like it is your own, even if it is not.
Shake hands.
Let yourself be guided.
Let your ego fall out the window.That leads Keith into one of the strongest ideas of the episode: there are really two versions of yourself you have to make proud.
The eight-year-old version of you.
And the eighty-year-old version of you.
The eight-year-old version still remembers what made you feel alive before the world got complicated. The eighty-year-old version knows what mattered and what did not. Keith tells Josh that 50-year-old Josh will be proud of 29-year-old Josh, and also proud of 23-year-old Josh, because he made choices that honored both who he was and who he was becoming.
Josh says there have been countless times between 23 and 29 when he realized his eight-year-old self would be absolutely stoked.
He grew up in a non-motorcycle household. The rule was basically: if you buy a motorcycle, you better find a place to live. But as a kid, he loved mini bikes and pocket bikes. He would sneak off to ride them. Somewhere inside him, that desire never left.
The decision to buy a motorcycle became one of the best decisions of his life.
The decision to choose a creative path became another.
At first, his parents did not fully understand either one. But over time, they saw that he was doing something that resonated with who he really was.
Keith connects Josh’s life to Zen and the Art of Motorcycle Maintenance and the idea that caring for a machine, taking a trip, and facing the road can teach a person how to care for his own life.
Then the episode moves into the road stories.
Josh explains that from Tampa to Los Angeles, the trip took exactly 14 days. Aside from a few days at home, he had been gone almost three weeks. The trip was not just about distance. It was about taking time. Visiting friends. Continuing conversations. Smelling the roses. Learning the difference between traveling for work and traveling because the road itself has something to teach you.
Keith says that if you want to hate the country, watch it on television.
If you want to love the country, ride across it on a motorcycle.
That idea sits at the heart of the episode.
Motorcycle travel puts you face-to-face with the country. Not the headlines. Not the noise. Not the outrage machine. The actual country. Gas stations. Backroads. Diners. Heat. Wind. Small towns. Strangers. Friends. People who help. People who wave. People who tell stories.
Small-town America is different when you meet it at eye level.
Josh says one of the biggest lessons of the trip was to underthink it.
Not to be reckless.
Not to be stupid.
Not to ignore real danger.But to stop worshiping imaginary danger.
He says most of the things running through your head will not be changed by thinking about them more. Prepare as best you can. Surround yourself with good people. Ride a good machine. Eat good food. Drink good wine. Carry what you need.
Then go.
If something happens and it is not life-threatening, you will learn a lesson that no paragraph, podcast, or advice column could ever teach you.
Keith and Josh talk about analysis paralysis and how people can think so long about launching something, announcing something, building something, or beginning something that it never actually happens.
The trip itself was a leap.
Flying across the country alone.
Buying a motorcycle from a stranger.
Riding 3,000 miles home.
No perfect plan.
No guarantee.
No full certainty.Just a decision.
Keith calls it a leap of faith.
He says most people live very safe lives. Safe cars. Safe neighborhoods. Predictable schedules. Trash pickup on Thursday. Street sweeping on Friday. Restaurants where the food is probably safe. Phones that can call help from almost anywhere.
But if people do not have an element of danger in their lives, they often invent one.
They manufacture fear.
They manufacture the boogeyman.
They manufacture the monster around the corner.Keith admits that he does this too. When everything is going right, he starts looking for the thing that is going to go wrong. But looking back over 50 years of life, he says he would not change much. The failures taught him. The hard things shaped him. The dangers that actually arrived were handled when they arrived.
The problem was all the time wasted fearing things that never came.
Josh says the mindset shift is simple:
What can go right?
Instead of only asking what can go wrong.
Then he adds another phrase:
Why not me?
But he explains that the same words can carry two completely different meanings.
“Why not me?” can be victim language. It can mean looking at someone else’s life and complaining that you do not have it.
Or it can be ownership language. It can mean looking at someone doing what you want to do and realizing that maybe they do not have anything magical that you do not have.
Maybe they just started.
Maybe they just tried.
Maybe they had half the money, half the resources, and twice the courage.Keith connects that idea to taking risks, betting on yourself, and swinging for the fence. He says failure has never killed as many dreams as fear has. A lot of people never fail because they never get off the bench.
The conversation then moves into the practical and brutal realities of the road.
Keith asks Josh about the hardest part of the cross-country ride.
Josh answers with one word:
Texas.
Texas was the soul crusher.
Wind.
Heat.
Construction.
Rough roads.
A lighter motorcycle.
No wind protection.
A cooked motor mount.
Long stretches.
Real miles.Texas Tourism:
https://www.traveltexas.com/Keith and Josh talk about the difference between modern touring motorcycles and older bikes. New motorcycles can have cruise control, Bluetooth, screens, comfort, and technology that would have seemed impossible decades ago.
But Josh’s old Harley was different.
Its “cruise control” was basically a screw under the throttle. Tighten it enough, and the throttle stays where it is. Keith jokes that it is like putting a zip tie on a chainsaw.
Josh tells a story about trying to use it once so he could remove sun sleeves while riding. A Range Rover got too close behind him, he throttled away, then realized the screw-down throttle was still holding speed and nothing was slowing him down.
He turned it off and never touched it again.
The episode then turns to the way motorcycles make you part of the elements.
Keith explains that on a motorcycle, you can tell what state you are in by feeling it. The heat, the cold, the wind, the rain, the smell, the road surface, the landscape. You are not sealed off in a climate-controlled bubble with the air conditioning set to 72 degrees.
You are in it.
You are part of it.
You are stripped down to the basics.
Keith asks Josh what he carries on a motorcycle trip when he is limited to saddlebags.
Josh’s essentials are simple:
Snacks.
Water.
Tire patch kit.
Portable air pump.
Tool roll.
Straps.
A camera.
A good person if possible.
Maybe spare fuel depending on the bike.The snack part matters because being broken down in the middle of Texas is bad.
Being broken down, thirsty, hungry, and hours from help is worse.
Keith and Josh also talk about Arizona heat, Phoenix, sunburn, and what happens when you choose a three-quarter helmet instead of a full-face helmet because you do not want people calling you through the intercom. Josh wanted to be in the moment, so he went old-school.
Arizona Tourism:
https://www.visitarizona.com/Phoenix, Arizona:
https://www.visitphoenix.com/Keith jokes that Phoenix is a testament to man’s arrogance.
Josh says he spent time with lifelong friends there, cooled off, went swimming, used sunscreen, and recovered from the sunburn before continuing home.
But he was not in a rush.
That matters.
The trip was not about escaping the road.
It was about experiencing it.
From there, Keith reflects on the importance of Josh documenting the whole thing. He talks about seeing Josh online, riding across unknown states, singing at the top of his lungs, living fully in the moment, and leaving behind proof that he was really there.
Keith says this is not just for Josh’s eight-year-old self.
It is for his eighty-year-old self.
It is also for his future family, future children, future friends, and future strangers who may one day look back and say, “What was he like in 2026?”
Josh will be able to show them.
He picked up a camera so he could remember experiences in both good times and bad. He kept holding the camera because other people were inspired by what he shared.
That is one of the most important creative lessons in the episode.
The internet can be a mess.
But it can also be a place where someone sees another person living with courage and decides to go do something with their own life.
Maybe they do not ride across the country.
Maybe they just ride the motorcycle to work.
Maybe they pick up the camera.
Maybe they start the business.
Maybe they take the first step.
Maybe they get a little bit freer than they were yesterday.
Keith closes the episode by giving Josh room to talk about his work. Josh shares I Am Riding Places on Instagram and YouTube, where he documents motorcycle travel, photography, writing, creative lessons, and experiences from the road.
He also talks about CR8CO, his new creative project born from the necessity to create. Through CR8CO, Josh plans to share writing, photography, apparel, camera gear, and creative work for people who want to start their own journey.
CR8CO:
https://cr8co.com/Keith points out that this kind of career did not really exist 10 years ago in the same way. Today, a person can follow a passion, learn the craft, ask questions, build an audience, document the journey, and create a life around the things that make them come alive.
Keith ends with a line from Jacques Cousteau:
If you have an exceptional life, you have no right to keep it to yourself.
Jacques Cousteau:
https://www.cousteau.org/That is what this episode is really about.
Not motorcycles only.
Not Instagram only.
Not travel only.
Not risk for the sake of risk.
It is about living an exceptional life and sharing it in a way that invites other people to go live theirs.
It is about buying the bike.
Taking the trip.
Trusting the road.
Shaking hands.
Letting the ego fall out the window.
Making the eight-year-old you proud.
Making the eighty-year-old you proud.
And realizing that the boogeyman is usually smaller than you made him out to be.This episode is about motorcycles.
But really, it is about freedom.
Listen to Episode 40:
PASTE SPOTIFY EPISODE LINK HERE
Chopping It Up Podcast Archive:
https://saarloosandsons.com/sscopodSaarloos & Sons:
https://saarloosandsons.com/Related Links and Resources
Listen to Episode 40 on Spotify:
PASTE SPOTIFY EPISODE LINK HEREChopping It Up Podcast Archive:
https://saarloosandsons.com/sscopodSaarloos & Sons:
https://saarloosandsons.com/I Am Riding Places Instagram:
https://www.instagram.com/imridingplaces/I Am Riding Places YouTube:
https://www.youtube.com/@imridingplacesCR8CO:
https://cr8co.com/Two Lane Life:
https://www.twolanelife.com/Two Lane Life YouTube:
https://www.youtube.com/@TwoLaneLifeHarley-Davidson:
https://www.harley-davidson.com/Facebook Marketplace:
https://www.facebook.com/marketplace/Tampa Bay:
https://www.visittampabay.com/St. Petersburg / Clearwater:
https://www.visitstpeteclearwater.com/Ventura County:
https://visitventuraca.com/Texas Tourism:
https://www.traveltexas.com/Arizona Tourism:
https://www.visitarizona.com/Phoenix, Arizona:
https://www.visitphoenix.com/Zen and the Art of Motorcycle Maintenance:
https://en.wikipedia.org/wiki/Zen_and_the_Art_of_Motorcycle_MaintenanceJacques Cousteau:
https://www.cousteau.org/ -
Topics Covered
Topics Covered
Josh
Josh Seiden
I Am Riding Places
IM Riding Places
imridingplaces
I Am Riding Places Instagram
I Am Riding Places YouTube
CR8CO
CR8CO.com
Chopping It Up Episode 40
Chopping It Up with Keith Saarloos
Keith Saarloos
Saarloos and Sons
Saarloos & Sons
Santa Ynez Valley podcast
Los Olivos podcast
Crazy Country 105.9
Motorcycle podcast
Harley-Davidson podcast
Harley-Davidson travel
Harley-Davidson road trip
Harley-Davidson culture
Motorcycle travel
Solo motorcycle travel
Cross-country motorcycle trip
Florida to California motorcycle trip
Tampa to California motorcycle ride
St. Petersburg Florida motorcycle
Ventura County motorcycle
California motorcycle creator
Buying a motorcycle sight unseen
Facebook Marketplace motorcycle
25-year-old Harley-Davidson
Old Harley-Davidson
Motorcycle adventure
Adventure motorcycle travel
American road trip
Two-lane roads
Two Lane Life
Leaving Two Lane Life
Small-town America
Americana
Documenting America
Family legacy
Small business stories
Independent business
Backroads of America
Open road
Freedom
Risk
Courage
Betting on yourself
Creative entrepreneurship
Creator economy
YouTube creator
Instagram creator
Motorcycle filmmaker
Motorcycle photographer
Travel photography
Motorcycle photography
Filmmaking
Content creation
Documenting your life
Creative career
Camera gear
Writing
Storytelling
Building your own path
Leaving the nest
Starting over
Taking the leap
Leap of faith
What if it goes right
What if it goes wrong
Why not me
Fear kills dreams
Failure and fear
Analysis paralysis
Underthink it
Stop overthinking
Personal growth
Finding yourself
Road lessons
Life lessons from motorcycles
Zen and the Art of Motorcycle Maintenance
Motorcycle essentials
Motorcycle packing list
Motorcycle saddlebags
Motorcycle tool roll
Tire patch kit
Portable air pump
Motorcycle snacks
Motorcycle road safety
Texas motorcycle ride
Texas wind motorcycle
Arizona motorcycle heat
Phoenix motorcycle trip
Sunburn motorcycle ride
Three-quarter helmet
Old-school motorcycle riding
Screw-down throttle
Motorcycle cruise control
Road Glide
Harley touring bikes
Motorcycle culture
Motorcycle freedom
American freedom
Cowboy spirit
Modern cowboy
Eight-year-old self
Eighty-year-old self
Make yourself proud
Living an exceptional life
Jacques Cousteau quote
Exceptional life
Real people doing real things
Ask people how
Creative inspiration
Go do the thing
Take the trip
Buy the bike
Trust the road
Coming home changed -
FAQ
Who is Josh from I Am Riding Places?
Josh, also known as I Am Riding Places, is a motorcycle traveler, photographer, filmmaker, writer, and creative entrepreneur who documents Harley-Davidson travel, small-town America, open-road experiences, and life on two wheels.
I Am Riding Places Instagram:
https://www.instagram.com/imridingplaces/What is I Am Riding Places?
I Am Riding Places is Josh’s creative platform where he shares motorcycle travel, photography, filmmaking, writing, road stories, creative lessons, and open-road experiences.
I Am Riding Places YouTube:
https://www.youtube.com/@imridingplacesWhat is Episode 40 of Chopping It Up about?
Episode 40 is a conversation between Keith Saarloos and Josh from I Am Riding Places about motorcycles, risk, freedom, solo travel, Harley-Davidsons, creativity, entrepreneurship, and the question “what if it goes right?”
What motorcycle trip does Josh talk about in this episode?
Josh talks about flying from Los Angeles to Tampa, Florida, buying a 25-year-old Harley-Davidson sight unseen from Facebook Marketplace, and riding it more than 3,000 miles back to Ventura County, California.
How far did Josh ride from Florida to California?
Josh says he rode 3,018 miles from early in day one to his home in Ventura County, California. In the conversation, the trip is described as more than 3,000 miles across the country.
Where did Josh buy the motorcycle?
Josh bought the motorcycle in St. Petersburg, Florida, after flying into Tampa and taking an Uber to meet the seller.
What kind of motorcycle did Josh buy?
Josh bought a 25-year-old Harley-Davidson motorcycle sight unseen from Facebook Marketplace.
Why did Josh leave his previous career chapter?
Josh explains that after years of riding motorcycles, documenting small-town America, and working with friends who became family, he felt it was time to take ownership of his own life and build something of his own.
What is Two Lane Life?
Two Lane Life is a motorcycle travel and lifestyle platform focused on Harley-Davidson riding, road trips, backroads, small towns, and motorcycle culture.
Two Lane Life:
https://www.twolanelife.com/Was Josh part of Two Lane Life?
Yes. In the episode, Josh talks about spending years working with the Two Lane Life team, riding Harley-Davidsons around the country, filming, photographing, and helping document small-town America and family legacy.
What does “leave the nest” mean in this episode?
“Leaving the nest” means stepping away from a successful and comfortable chapter in order to build something new. For Josh, it meant leaving a good thing well and taking responsibility for his own creative path.
What does Keith Saarloos mean by “there is a little cowboy in every American”?
Keith uses the phrase to describe the independent, risk-taking, freedom-seeking part of people that wants to face the unknown, explore the country, and find out what life can become beyond the safe road.
What does “what if it goes right?” mean?
“What if it goes right?” is one of the main ideas of the episode. Instead of only asking what could go wrong, Josh and Keith talk about asking what could go right if you take the leap, trust yourself, and start moving.
Why does Josh say to “underthink it”?
Josh says “underthink it” because overthinking can become analysis paralysis. His point is not to be careless, but to prepare well, stop manufacturing fear, and go do the thing before fear talks you out of it.
What is analysis paralysis?
Analysis paralysis is when someone thinks, plans, worries, and evaluates for so long that they never actually take action. Keith and Josh discuss how overthinking can prevent people from launching projects, taking trips, or changing their lives.
What does this episode say about fear?
The episode says fear often kills more dreams than failure. Keith and Josh talk about how people manufacture imaginary danger, build up the boogeyman in their minds, and avoid risks that might actually change their lives for the better.
What does Josh mean by “why not me?”
Josh explains that “why not me?” can be said with a victim mindset or with an ownership mindset. It can either mean complaining that someone else has the life you want, or realizing that you may have the ability to build that life too.
What does Keith mean by the eight-year-old you and the eighty-year-old you?
Keith says there are two versions of yourself you should try to make proud: the eight-year-old version who remembers what made you feel alive, and the eighty-year-old version who will look back and know whether you lived honestly and courageously.
Why are motorcycles important in this episode?
Motorcycles are important because they represent freedom, risk, presence, and direct contact with the world. Keith and Josh talk about how riding a motorcycle strips life down to basics and forces you to be present.
What does the open road teach Josh?
The open road teaches Josh patience, connection, humility, courage, presence, and the importance of slowing down enough to meet people, visit friends, and experience the country beyond the freeway.
Why does Keith say if you want to love the country, ride across it on a motorcycle?
Keith says watching the country on television can make a person angry or disconnected, but riding across it on a motorcycle puts you face-to-face with real people, real towns, real weather, and real America.
What did Josh learn from documenting small-town America?
Josh learned the importance of culture, family legacy, small business, human connection, and taking the time to sit with people, look them in the eye, and understand where they come from.
What is CR8CO?
CR8CO is Josh’s creative project focused on writing, photography, apparel, camera gear, creative work, and helping people begin their own creative journeys.
CR8CO:
https://cr8co.com/What does Josh share through CR8CO?
Josh plans to share writing, photography, apparel, camera gear, creative resources, and lessons from his own life as a motorcycle traveler, photographer, filmmaker, and creator.
What does Josh carry on a motorcycle trip?
Josh mentions snacks, water, a tire patch kit, portable air pump, tool roll, straps, a camera, and possibly spare fuel depending on the motorcycle.
Why are snacks and water important on a motorcycle trip?
Josh says snacks and water matter because if you break down in the middle of nowhere, especially somewhere like Texas, being hungry and thirsty makes a hard situation worse.
What was the hardest state on Josh’s ride?
Josh says Texas was the hardest and most intense part of the ride. He describes it as scary, rewarding, and enjoyable, with rough roads, construction, wind, heat, and long stretches.
Why was Texas difficult on the motorcycle?
Texas was difficult because of the wind, construction, rough roads, long distances, and the fact that Josh was riding an older motorcycle with no wind protection and mechanical limitations.
What happened with Josh’s screw-down throttle?
Josh’s old Harley had a screw-style throttle lock. He used it once while trying to remove sun sleeves, but after accelerating away from a Range Rover, he realized the throttle lock was still holding speed. He turned it off and never used it again.
What happened to Josh in Arizona?
Josh says the weather was good until Arizona. By then he was sunburned from riding with a three-quarter helmet and no face protection. He stopped near Phoenix to spend time with lifelong friends, cool off, swim, and recover.
Why did Josh wear a three-quarter helmet?
Josh wore a three-quarter helmet because his full-face helmet had an intercom, and he did not want calls coming in. He wanted to be fully present on the ride.
Why does Keith mention Zen and the Art of Motorcycle Maintenance?
Keith mentions Zen and the Art of Motorcycle Maintenance because the book connects motorcycles, travel, maintenance, philosophy, self-examination, and the way a journey can teach a person about life.
Zen and the Art of Motorcycle Maintenance:
https://en.wikipedia.org/wiki/Zen_and_the_Art_of_Motorcycle_MaintenanceWhat does this episode say about documenting your life?
The episode says documenting your life matters because photos, videos, and writing become proof that you lived. They also inspire other people to go live more fully.
Why does Josh carry a camera?
Josh carries a camera to remember experiences, preserve moments, tell stories, and inspire other people through the life he is living.
What does Keith mean by “if you have an exceptional life, you have no right to keep it to yourself”?
Keith uses that Jacques Cousteau idea to say that when someone lives a meaningful, adventurous, inspiring life, sharing it can encourage other people to live more courageously too.
Jacques Cousteau:
https://www.cousteau.org/Is Episode 40 only for motorcycle riders?
No. This episode is for motorcycle riders, but it is also for anyone thinking about taking a risk, starting over, building something creative, leaving a safe chapter, or doing the thing they have been afraid to do.
Is this episode about Harley-Davidson motorcycles?
Yes, Harley-Davidson motorcycles are a major part of the episode, but the deeper conversation is about freedom, risk, creativity, courage, and personal growth.
Where can I find Josh online?
You can find Josh at I Am Riding Places on Instagram and YouTube, and through his creative project CR8CO.
I Am Riding Places Instagram:
https://www.instagram.com/imridingplaces/I Am Riding Places YouTube:
https://www.youtube.com/@imridingplacesCR8CO:
https://cr8co.com/Where can I listen to Episode 40 with Josh?
You can listen to Episode 40 of Chopping It Up with Keith Saarloos here:
PASTE SPOTIFY EPISODE LINK HERE
Where can I find more Chopping It Up episodes?
You can find more episodes of Chopping It Up with Keith Saarloos here:
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THE Transcript
Josh, Josh Seiden, I Am Riding Places, IM Riding Places, imridingplaces, I Am Riding Places Instagram, I Am Riding Places YouTube, CR8CO, CR8CO.com, Chopping It Up Episode 40, Chopping It Up with Keith Saarloos, Keith Saarloos, Saarloos and Sons, Saarloos & Sons, Santa Ynez Valley podcast, Los Olivos podcast, Crazy Country 105.9, motorcycle podcast, Harley-Davidson podcast, Harley-Davidson travel, Harley-Davidson road trip, Harley-Davidson culture, motorcycle travel, solo motorcycle travel, cross-country motorcycle trip, Florida to California motorcycle trip, Tampa to California motorcycle ride, St. Petersburg Florida motorcycle, Ventura County motorcycle, California motorcycle creator, buying a motorcycle sight unseen, Facebook Marketplace motorcycle, 25-year-old Harley-Davidson, old Harley-Davidson, motorcycle adventure, adventure motorcycle travel, American road trip, two-lane roads, Two Lane Life, leaving Two Lane Life, small-town America, Americana, documenting America, family legacy, small business stories, independent business, backroads of America, open road, freedom, risk, courage, betting on yourself, creative entrepreneurship, creator economy, YouTube creator, Instagram creator, motorcycle filmmaker, motorcycle photographer, travel photography, motorcycle photography, filmmaking, content creation, documenting your life, creative career, camera gear, writing, storytelling, building your own path, leaving the nest, starting over, taking the leap, leap of faith, what if it goes right, what if it goes wrong, why not me, fear kills dreams, failure and fear, analysis paralysis, underthink it, stop overthinking, personal growth, finding yourself, road lessons, life lessons from motorcycles, Zen and the Art of Motorcycle Maintenance, motorcycle essentials, motorcycle packing list, motorcycle saddlebags, motorcycle tool roll, tire patch kit, portable air pump, motorcycle snacks, motorcycle road safety, Texas motorcycle ride, Texas wind motorcycle, Arizona motorcycle heat, Phoenix motorcycle trip, sunburn motorcycle ride, three-quarter helmet, old-school motorcycle riding, screw-down throttle, motorcycle cruise control, Road Glide, Harley touring bikes, motorcycle culture, motorcycle freedom, American freedom, cowboy spirit, modern cowboy, eight-year-old self, eighty-year-old self, make yourself proud, living an exceptional life, Jacques Cousteau quote, exceptional life, real people doing real things, ask people how, creative inspiration, go do the thing, take the trip, buy the bike, trust the road, coming home changed.
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Saarloos + Sons archive host Keith Saarloos. Context photograph; not a portrait of the guest or a photograph of this recording.
