How Three Tech Dudes Biked 500 Miles from SF to LA (Finale)

Pismo Beach, California

If you missed it, here’s part I and part II.

200 miles to go

As I cycled up “The Climb”, The bright blue skies welcomed me to the peak of the hill. I pulled out my Gatorade, chugged it and closed out the hardest climb of this ride.

We ended the day in the small town of Cambria: 71 miles, 5514 feet of climbing, 5000 calories burned.

Six days down. Four days left. Two hundred miles to go. After Big Sur, the three of us leveled up in cycling. Pismo Beach, 45 miles, 2000 feet of elevation? Easy money.

We left at 11am the next day and crushed the first 18 miles at a 14.5 mile per hour pace. (Note: The average pace was around 10 to 12 mph depending on incline). I ran into problems with my gear shifters where I couldn’t shift from my larger gear to my smaller gear. We stopped at Morro Bay to get my gears fixed and munch on Taco Bell.

As we continued along the route, we stopped by a gas station to fuel up and use the bathroom. At each stop, we’d take turns watching each others bike while the other went inside to grab water and snacks. We laid our bikes down and rested on the curb. As I pulled out more topical ointment to rub on my knee, a soft-spoke, old lady, probably in her 60’s approached us.

San Francisco had trained me to ignore strangers. But as she came up to us, she seemed befuddled. An emergency tire light went off in her car. I explained to her that she just needed to fill up her tires. I intended to end the interaction there, but we could see it in her eyes that she needed our help. Raymond, being the great samaritan, stepped in and helped her fill up her tires.

She told us that normally, her husband knew what to do. But he had just passed away, so she was freaking out. I had been battling my knee pain & Raymond had battled his back, but it was important to put things in perspective. It’s easy to forget that we aren’t the center of the world. Everybody is going through their own challenges.

We left the gas station. I was expected to lead the whole trip but this time, I asked Raymond to lead.

Something was wrong.

Like a baby in the middle of the night, the pain in my knee started screaming its way into puberty. The volume on my music was turned on full blast, yet I couldn’t hear it. There was absolutely no way I could bear this much pain for another 200 miles.

I popped a painkiller which would dull the pain for 40 minutes. But like a lion trapped in a den, it returned with hunger and vengeance. I endured four days on this knee, by pressing the ignore button but I could no longer do that. If pain was an education in enlightenment, I guess it was time to start class.

Brian and Raymond cycled off into the distance. They got so far ahead, they were no longer visible. I had about 20 miles left. My mind began thinking of the next four days. 200 miles on this would literally be impossible, but I couldn’t focus on the 200 miles. I had to focus on the next step.

The pain would ignite every time my left leg was at the top of its stroke, bent at a 90 degree angle. At 70 pedals per minute, this meant I’d be bending my leg about 8,400 times until I got to Pismo Beach. I could compensate the pedaling with my right leg, cruise for 10 to 15 seconds then repeat. This could cut down the amount of times I’d bend my leg by about 20-30%. I just needed to make it to Pismo Beach and then I could figure it out from there.

It’s funny. When something is painful or uncomfortable, the mind will start to self-rationalize its way out of the pain. I became fearful that I was causing permanent damage. And this fear, caused me to be more timid and slurped away at my self-confidence.

As I continued cycling, I see black dots turn into actual human beings. Brian and Raymond. They waited for me and we were close. 5 miles out. We made it to Pismo Beach.

The Search

When we got to Pismo beach, I spent hours ferociously Googling the shit out of the words: “bike”,”knee”,”pain.” I stumbled upon various solutions: getting a full custom bike fit, using CBD oil, ice, topical Castor Oil, a stronger knee brace, more pain killers and cryotherapy. I decided I would try all of them.

I spent the night with an ice pack glued to my knee. I spent $20 on an uber to CVS just to get a stronger knee brace. I called every bike shop in Pismo Beach for a bike fit. I called everywhere for CBD oil & cryotherapy. I had to do everything in my control to solve this problem. If I lost, so be it.

The devil in my mind convinced me that I could be permanently damaging my knee. That shot my confidence. The next day, we had a 60 mile ride to Solvang. 45 miles on this knee was fuckin hard. There no way I could do 60 miles on this knee.

With a few strokes on the pedal, I couldn’t do it. I was done.

Ubering was the last resort and I had no other choice. I had to call the $120 Uber to Solvang. Fuck. Fuck. Fuck.

I felt like I was compromising on the challenge. I felt like taking an Uber once gave me an easy out. It would make it easy for me to take an uber the rest of the way till LA. But physically, there was no way I could relive those painful 45 miles again. I had to accept the circumstance. I did everything.

I arrived in Solvang and found a bike shop that re-adjusted my seat. When cycling, pressing the heel of your foot on the pedal, your leg should lock straight. With the ball of your foot on the pedal, the leg should bend at about 30 degrees. We raised my seat up about an inch.

This made a HUGE difference. The pressure was no longer on my tendon, but on my thigh.

Next, I purchased CBD oil from the nearest health market to help treat the inflammation. The closest cryotherapy shop was The Lab in Santa Barbara.

The next day, I left Solvang at around 8am with the hope of making it to the cryotherapy shop by 2pm. I felt the cold breeze of the morning as I cycled past the Solvang vineyards, gingerly pedaling to keep the pain dormant. I pedaled up the ramp of the highway, with cars frequently vrooming by at 60 mph. The shoulder was wide and with each stroke, I pumped more confidence through my legs.

I pedaled for about 7 miles. A giant hill loomed. And then it awoke.

The pain started kicking, screaming, begging me to give up. Breathe. Breathe. Breathe. I’d often start meditating when my knee began hurting but the pain was unbearable. I clutched the brake, pulled over to the side and rubbed some Bengay on my leg. Nope, not happening. I called an Uber for the last 35 miles to Santa Barbara.

When I arrived in Santa Barbara, I immediately went to the cryotherapy shop. I had tried every single item on my list and this was my last hope. I had already Uber’ed two legs of this trip. If this didn’t work, it was game over.

When I got to The Lab, the shop reminded me of a high-tech garage from the future:

The place had a VO2 max monitor, a locker room, astroturf grass with thick ropes. Maximizing human performance. Now this was my type of place!

There were two blonde-haired men standing at the counter, with a slick-back comb over dressed in track suits. I explained to them that I was on a bike trip from SF to LA and that I had patellar tendonitis. He responds by saying Oh, cryotherapy for inflammation injuries. Let’s get you in.

I strip off my clothes, with only my boxers remaining. I put on a robe and slip on a pair of socks & slippers. This is what the chamber looks like:

The trainer explained that I’ll be inside for three minutes. I step into the chamber and the trainer yells out “if it gets too cold, just let me know and I can let you out early.” Fuck that, I’m going the full three minutes.

The chamber starts and liquid nitrogen starts permeating every inch of space within the chamber. The temperature is -275 degrees. I stand and start focusing on my breathe. I could feel my hands and feet start shivering and pretty soon my entire body was numb. It felt as if I was getting stabbed by thousands of needles. I start breathing heavily since shallow breaths would make me feel colder. The temperature dropped to -300 degrees  and then I stepped out.

When your body is brought to extremely low temperatures, the body pushes the blood to its vital organs. But when you step out of the chamber, vasodilation occurs. This means the blood vessels expand wider than normal. This resupplies the body with much richer, nutrient-dense, oxygenated blood, which is especially good for injuries.

The trainer wrapped an ice pack around my knee. As I walked out I asked the trainer if I could cause permanent damage to my knee if I kept biking. He nonchalantly replied that many people come in with patellar tendonitis and assured me I wouldn’t tear anything. In fact, he encouraged me to finish the ride.

Boom. Part of what had been stopping me from biking wasn’t the pain. It was the fear of permanent damage. But because the trainer had said I couldn’t make it any worse, I took the pain I had to endure as a personal challenge. I promised myself that I was going to make up the 35 miles I had missed.

I returned to our hotel, changed back into my biking clothes and clipped onto my bike. I began pedaling. No pain. I took a few more strokes to the stop light. No pain. I pedaled another block. No pain. I pedaled another mile. No pain. 4 hours later, the pain gradually started creeping back, but I had made up the 35 miles I missed.

Call it placebo, but I was back in business. Cryotherapy had worked.

The Home Stretch

By this point both Brian & Raymond were tired, but they were in much better condition than I was. After pushing through Big Sur, each route was relatively flat. Armed with my newfound confidence, I was ready to complete the ride. We had two days left: 45 miles, 1700 feet elevation to Port Hueneme, then 50 miles, 900 feet elevation into Santa Monica.

After cryotherapy, I was able to bike but my left knee felt ginger. I couldn’t exert a ton of force on it, but I could ride at a  relatively consistent pace. I stayed on lower gears and kept my own pace while Raymond, Brian flew ahead of me.

We completed the 45 miles to Port Hueneme and the vicious pain I experienced at Pismo Beach continue to stay asleep. One more day, 50 miles into Santa Monica.

As we pedaled into Santa Monica, the SoCal blasted heat on our yellow jerseys as we pedaled into Santa Monica. I’d turn right, and see ocean blue waves, breaking along the coast, as surfers caught the next break. Beautiful, bikini-clad women, hairy old men, bubbling young kids frolicked across the sandy beaches as we coasted by. Southern California. Malibu.

Malibu was the most dangerous portion of the ride. 50 mph, small bike shoulder with cars double-parked meant we shared the lane with the angry LA drivers. As I glanced at my Apple Watch, I’d saw the mileage tick up. 23, 24. Each tick inching us closer and closer to Santa Monica.

My knee has slight bits of pain but it was manageable. With LA in sight, adrenaline started to kick in, dulling the pain, allowing me to use my left leg to pedal.

Brian felt his tire and felt it falling flat. Probably a hole. But at this point, we didn’t give a f*ck. We tasted victory. So he pumped it up a bit and continued cycling.

The road transformed into a beach and the famous Santa Monica pier got larger and larger. I kept telling myself to pedal faster.

As I pedaled, in the corner of my eye, I see a cute girl.

Nope. I pedal harder and harder as if I didn’t even have patellar tendonitis. At this point, my mind was in this not give a f*ck attitude. I was willing to give up my ability to walk for a few weeks.

Coastal shrubs turned into beautiful mansions. Bright blue skies became tinted with white smog population. Los Angeles. We made it.

Epilogue

Raymond, Brian and I gathered at the Pier and took a final picture:

By the end, here were our statistics:

• 506 miles

• 10 flat tires

• 21,000 feet of elevation

• 21,960 calories burned per person

• 11.8 average miles per hour

It might be easy to think that the three of us were extremely fit. Or that we’re crazy. Or that we’re “outdoorsy.” Brian didn’t have a bike before agreeing to go on this trip. Yet, he cycled the highest number of miles out of all of us.

Your misogi might not be physical. It can be intense, like coding everyday for 365 days, going from zero experience to world championships in public speaking or losing 100 lbs.

But it can also be on a small scale, talking to that guy/girl that’s out of your league, emailing the celebrity, singing your lungs out at the karaoke bar.

Because looking back on our lives, the moments we’re proudest of, are the moments we pushed ourselves to be greater than we ever thought possible. They’re the moments when we said f*ck you to fear and did it anyway. They’re the moments when we crushed our self-imposed limitations.

So step out the door, take a whiff of the beautiful world we call life. Because once you realize the power of the human mind, I promise you, that you’ll never be the same again.

Thanks for reading!

How Three Tech Dudes Biked 500 Miles from SF to LA (Part 2)

Santa Cruz, California

When Raymond called me, we were right here: 

We were in the bum effin middle of nowhere. No ubers. No taxis. This is what the road looked like: 

I offered to carry a portion of his luggage but he didn’t want to do that to us. He planned to call and uber and taxi to meet us in Santa Cruz. 

My skills at persuasion were good. But the firmness of his statement meant his decision was made. At that point, the pain was so unbearable, he wanted to cry. 

After hopping off the phone, he took a swig of water, unloaded his backpack and sat on the curb. He opened up the uber app, a blank green canvas map engulfed his phone. He centered his location and pressed enter, attempting to get the nearest driver. Uber & Lyft service unavailable. Shit. 

Rather than give up, his bulldozer mind cycled through ideas on how he could get to Santa Cruz. We had just passed by the town of Pescadero, which had an arts festival going on. Maybe, just maybe, he could find a person in town to give him a lift to Santa Cruz. 

He exhales and takes a swig of water allowing his body to recuperate. He throws his backpack back on his back, only to feel a sharp twinge on his lower back. He tries to pedal but the sharp pain stabs his lower back. He walked to the town of Pescadero. 

Pescadero was a small, quiant town with no large buildings. He finds a gas station, purchases a bottle of water. He googles for a car service. None available. Since Pescadero had an arts festival that day, maybe he could ask a stranger to give him a lift. He talks to three tourists only to find that they were all going towards San Francisco. 

As Raymond ticked off each idea, he was running out of options. He had phone last option: phone a friend. Dun dun dun *Insert who wants to be a millionaire music*

He facetimes one of his best friends, Ryan. In the background, he notices that Ryan isn’t home. He’s outside. Where was he? Ryan had planned to take his girlfriend skydiving that day. Unfortunately, when he got to the skydiving location, the weather conditions weren’t suited for skydiving. But where was this skydiving location? 

Santa Cruz. 

In a miraculous turn of luck, Ryan, Raymond’s last option, had been in the area. If the weather conditions were good, he wouldn’t have been free. Ryan found Raymond in Pescadero and took him to Santa Cruz. 

Upon arrival, he called every bike shop in town asking Do you guys carry paneers? 

We do. 

Mission saved.  

Brian and I cruised 30 miles into Santa Cruz, arriving at 5pm. Santa The day totaled to 60 miles, 3000 feet of elevation. We re-convened with Raymond at the hostel and spent the rest of the day devouring thai food and exploring the boardwalk.

Santa Cruz is Northern California’s premiere surftown. A town of 90,000 people, home of UC Santa Cruz, the city is a blend of bushy forests & soothing beaches. Since Santa Cruz is a surf town, we thought we should make the most of our visit by going surfing. Internet surfing. We surfed mindless youtube videos, refreshed instagram and vegetated the rest of the night. Fun stuff. 

Our next ride was 45 miles to Marina, CA. A random city that sat adjacent to Monterey: 

We left at around 11am and enjoyed an easy, flat ride towards Marina. We pedaled through flat farmlands, putrid smelling horse poop, as the sun settled past the horizon. The crisp sounds of music tapped my eardrum, with each note soothing my mind into the flow of the ride.   

Poke. 

A spec of pain poked the front of my left knee, barely noticeable. I treated this poke like an annoying baby. 

Ignore. 

Soon, the spec of pain evolved into an annoying little brother, banging on the door of my mind, begging to come in. 

Ignore. 

At some point I had to open the door. Not right now though. 

Ignore. 

I had no clue what it was. It kinda hurt, but we still had about 350 miles left, with our hardest day in two days. One thing I learned from Raymond’s fiasco was that small discomforts multiply out. Raymond wearing a 30lb bag for 20 miles is do-able. Multiplying that across 500 miles is nearly impossible. The pain in my knee was no different. 

When we biked, Brian wasn’t concerned with speed, he was concerned with pedaling correctly. Combine this with hybrid wheels, he’d often be pedaling slower in the back. Through his life, he’s had multiple injuries: breaking his foot, tearing his shoulder, injuring his back. In life, it’s the painful experiences that shape our behavior. And these experiences made Brian a bit neurotic about an injury during this ride. 

In preparation for this ride, Raymond & I had an attitude of youth invincibility. Brian did the opposite. He researched, trained and took the most precaution, which meant he was the most prepared. 

When I brought up my knee pain, Brian immediately knew the answer: your bike seat might be too low. Might be good to see if you can get a bike fit. 

A bike fit requires a bike fitter to measure the dimension of your body, pedal stroke and hand positions. Then, he/she will re-adjust the saddle height, position to your body size. If the seat is too low, you’d be putting too much pressure on the front of your knee:

You can see in this photo, how the man’s knee is nearly in front of his toe(black line). Raising the seat would push the knee back, thus, putting less pressure on the knee(red line). 

Although the pain was manageable, I began to panic. I had no idea what a small knee pain, multiplied over 300 miles would become. Would I be completely incapacitated in 100 miles? 200 miles? 

We stopped by REI where I got my bike seat adjusted + bought a patellar tendon strap. However, the REI crew didn’t have proper bike fit measurement equipment which meant my bike seat was still too low after they adjusted it. This would come back to bite me. 

The patellar tendon strap absorbed some of the pressure that I put on my tendon. My knee hurt, but the pain was bearable. If the pain didn’t get worse, I think I could keep going. I self-diagnosed myself with patellar tendonitis.  

On we went. The 71 mile monster, lurking ahead of us. 

Big Sur 

The trek into Big Sur was an easier 45 mile ride. Through Big Sur was the tough one:

The roads in Big Sur slivered like a snake on alongside the jagged cliffs. Ocean waves crumbled against the coastline while a cool breeze rustled through the luscious green trees. The bike shoulder was only 1-2 feet so cars would vroom by awfully close:

Because the roads winded, this limited the speed of cars. We’d pedal up hills, cruise down, pedal up again, cruise down. At one stoplight, I pull up next to two bikers. They were dressed in a blue and red bike jersey. And both had steel-carved calves. Damn. And they also looked to be retired and in their 70’s. Damn. 

As the light flicks green, one of the men pedal right beside me:

Old Dude: How’s it going? Where are ya guys headed?

Me: We’re headed from SF to LA. You?

Old Dude: We’re headed from Santa Cruz to Orange County. 

We chat for a few seconds and he pedals past me. After a few minutes, he’s pedaled into the distance. I can’t see him. This guy is probably three times my age but he flew right past me as if I was the 70 year old. It’s always refreshing to meet people who haven’t allowed age to suppress their lust for adventure. I’d like to be that old dude when I’m 70. 

We arrived at Big Sur Lodge and rested up for the toughest ride of this trip: 71 miles, 5511 feet of elevation. We left Big Sur lodge at 9am and planned to end in the small town of Cambria. 

About 40 miles in, the three of us concluded that Big Sur wasn’t as hard as we thought. That is, until we hit “The Climb.” 

The Climb, was a 1000 foot, straight uphill climb. When cycling up a hill, we usually shift to a lower gear. 

Good cycling technique means maintain consistent pedaling cadence. To maintain cadence, you shift your gears higher with incline, lower when it’s flat. Climbing becomes exponentially harder when you already hit your lowest gear but cannot maintain cadence. The only thing you can do is generate more power with your legs to push through the resistance. 

I could feel a thick wad of moisture underneath the straps of my backpack. My backpack started to stink of sweat. I don’t remember if my left knee hurt. My focus was on the burn in my thighs and conquering this 71 mile beast. 

The beauty behind endurance sports like cycling, running, swimming is the repetitive motion. Unlike football, basketball, you are repeating the same exact physical motion, in this case, for hours. Some might see this as boring. But boredom is the best test for the equanimity of your mind. Nothing in life is boring. When we feel bored, it’s our failure to squeeze the interesting juices from the amazing world around us. Endurance sports train this skill. 

I clicked my gears lower until I hit my lowest gear. I couldn’t click any lower, which meant I needed to exert more force through my legs. As rivers of sweat drifted down my forehead, the beautiful views of Big Sur faded in the background. I was alone in the crevices of my mind. 

Why was I doing this? Why did I feel this urge to bike 500 miles? Was I doing this to impress girls? What did I have to prove to others? Was I running away from something? 

A few years ago, I went on a 10-day vipassana meditation retreat. The retreat required us to meditate for 10 hours per day with a break every hour, no talking, no writing, no cell phone. There was one moment on the retreat where I had been meditating for one hour straight and I felt like I was sitting on burning stove. Usually, we would have a 5 minute break every hour of meditation. This time, I challenged myself to meditate through the break and go for two hours. 

There was an odd moment where the pain became so unbearable, I started giggling like a little school girl. It was as if I was a 3rd person, in my own story, watching the pain sit in my legs. Yes! That was it. I completely detached from the pain in my legs. What Buddha meant with enlightenment is suffering is that any sort of pain, physical, emotional is the path to enlightenment. Peace comes from the detachment and overcoming of pain. 

A woman I dated a few months ago  went through a soul-crushing breakup, which triggered her to start reading, investing in her passion for cooking and start exercising. Colin O’Brady when traveling in Thailand suffered 3rd degree burns from a fire accident. This accident triggered him to win a triathlon, ultimately spurring an amazing career as an athlete. He became the fastest man to cross Antarctica solo, unassisted. It was ultimately the pain of her mother that led Cheryl Strayed to go on the 1,100 mile hike through the Pacific Coast Trail. This led to the book & movie: Wild. 

And that’s why I was doing this ride. I knew that pushing through the pain, struggle would sculpt the best version of myself. 

Little did I know, the worst pain of this trip had yet to come. 

END OF PART 2

Click here for the final part!

How Three Tech Dudes Biked 500 Miles from SF to LA (Part 1)

A searing knife of pain sliced through my knee as I pressed down on the pedal. Burn. Each pedal stroke, igniting a flame within my swollen red knee. Cars whiffed by at 80 mph. My friends, no longer visible, as they pedaled into the distance. The pain was unbearable. My self confidence was shot……..  

In Japan, misogi is a water purification ritual to reach spiritual enlightenment. In the west, it means to do something that radically expands what you believe is possible. This bike trip, was our misogi. San Francisco to Los Angeles. 506 miles. 10 flat tires. 21,436 feet of elevation. 65,880 calories burned. Patellar Tendonitis. Stranded with no ubers or taxi’s. 1000 foot climbs. Steel-calved 70 year olds. This is the story of our misogi. 

The Call to Adventure

Three years ago, I was unemployed and living at home. The combination of a non-existent dating life & lots of free time, gave room for interesting ideas to dance in my head. One idea caught my eye: biking from SF to LA.

Telling my dad this idea was a mistake. He wasn’t pleased. He begged, made threats, used passive aggression. And eventually, I agreed to not go on this trip, if he helped me pay for part of my data science bootcamp. Negotiation FTW. 

So I buried the idea. At least until I moved out. 

After climbing the Month to Master mountain, I needed to find a new mountain. It’s the large goals that give our every days a sense of purpose. Biking from San Francisco to LA resurfaced and BAM, it had a WWE chokehold on my brain. 

Assembling the Team 

Finding people interested in this was hard. I sent texts, emails, FB messages, went into long diatribes at parties. Here was my pitch: 

If you do the math, 500 miles/10 days = 50 miles per day. If we go 10 mph, that’s about 5 hours per day. 6 hours if we count breaks. If we sleep about 8 hours per day, that’s still 10-11 hours. Very do-able.  

Despite my persistent & mathematical efforts at persuasion, I had no bites. 

Until Raymond. 

Raymond is my roommate who currently doubles as a robust bulldozer. This is a man who can party for seven days straight at yacht week and a man who loves triathlons. An adventurous fellow. Climb a mountain, take a salsa class, jump off a cliff, this is the dude you can count on to say “I’m down.” A man who lives life on the edge. I’ll let his dating profile pic speak for itself: 

As we sat at our dining table, I prepared to give Raymond the full pitch. Before I could dive in, Raymond blurted: Oh, I’ve always wanted to do that. I’m down. That was easy. 

For Brian, not as much. 

A VR, product-designer and real-life “hype man”. After a night out, this is a dude who can’t sleep since he needs the hype to “settle.” Neurotic about injuries since he’s had problems with his back, feet, shoulder (which ultimately benefits him for this trip). A dude you can always count on bring up the energy level, but can’t count on to change a tire. I’ll let this instagram story speak for itself:

Brian needed convincing. He didn’t own a bike. But one night, as we were eating delicious Greek food, he said Fuck it, I’m in.  He purchased a $900 hybrid Kona Rove. Team assembled.

As complete noobs to bike touring, we were in over our heads. We prepped by biking to San Jose, Sacramento and multiple trips to Hawk Hill in Marin County. The San Francisco summer days chugged along and soon, the date was upon us. 

August 17, 2019 - San Francisco, California 

This was the full route not including detours:

On August 17, 2019 at 12 noon, we started our cycling adventure at the busy, tourist-packed San Francisco Ferry Building. The first leg ended at the lighthouse hostel near Half Moon Bay. Here’s a picture of us at the SF ferry building:

I lead the initial legs of this trip through the coast of San Francisco, Sutro baths and down the coastline along ocean beach. We cycled through Daly City, which required a solid amount of uphill climbing.

If you’re a dude who skips leg day, an easy way to eliminate chicken legs is to cycle uphill. Cycling uphill is like pouring gasoline on the flame of your thighs. Every stroke ignites the fire while beads of sweat drizzle down your forehead attempting to cool you off. 

In cycling elevation trumps distance. Biking 100 miles with 0 feet elevation is much easier than biking 50 miles with 5000 feet of elevation. Our first few days was low on the mileage but high on elevation, which meant a majority of our ride would consist of climbing. 

Just as we completed a 200 foot climb in Daly City, google maps robotically commanded me to make a right in 300 feet. To our dismay, google maps didn’t tell us there was another damn hill.

That’s when Raymond, the bulldozer, started to crack. 

Raymond, a normally tame, proper, positive person, exclaimed: Jeff, did you check the route we we’re going on?!? No more hills, okay! We’re not trying to kill ourselves. 

Although what he said wasn’t rude, it was unusual. Raymond never gets upset. Something was up.

We ended at the lighthouse hostel and ate scrumptious seafood in Half Moon Bay. The next day, we had a 60 mile ride into Santa Cruz. I asked Raymond how he was doing and he stoicly replied: Terrible. I was worried.

The First Hurdle

About 15 miles in, we hit a 500 foot climb. Raymond lagged further and further back. When we reached the top, we took a break to fuel up on water, energy gels and bars. Raymond’s face had the look of death. Raymond unclipped his pedals, sat on the curb, closed his eyes and buried his face in his arms. He didn’t say a word for the next ten minutes. 

At this point, both Brian and I were tired but not at the point of dying. Raymond wasn’t out of shape. He’s run triathlons, plays basketball, tennis and lives an active lifestyle. It was his back. 

Imagine going into a gym, grabbing a 30 pound dumbbell and dropping it in your backpack. Then, wear this for literally the whole day. This was what Raymond was doing. Oh wait, he was also cycling uphill. Oh, and let’s throw in 500 miles to LA. 

I meekly asked him if he was okay. He replied: I’ll make it to Santa Cruz. We cycled on. 

Since I was leading these legs, I would periodically glance back to make sure everyone was in sight. After another 10 miles, I glance back and see Brian right behind me. But Raymond was nowhere to be found. 

In a few seconds, I get a call: 

“Jeff, I’m done. I can’t do this anymore.” 

END OF PART 1

Click here for Part 2!!!

How do I break into data science without a relevant degree, experience?

I’ve done dozens of interviews and ZERO people do this. As someone who might not have a traditional math, statistics background, this is the single best strategy to break into data science. 

If you’re looking for advice on learning technical skills, read my Quora post. 

In 2019, there are dozens of masters programs sprouting up at major universities like MIT, Berkeley etc. Although the technical skills are important, you won’t be able to compete directly with PhD’s in math. 

You’ll need to use the briefcase technique. And this is how it works: 

1.Informational Interview: Before applying for a company, you’ll need to discover your target company’s pain-points. There are multiple ways to do this: 

• Conduct an informational interview

• Use the product and find areas of improvement 

• Read forums, comments from users on areas of improvement

The most informative will be conducting an informational interview. Conducting informational interviews deserves a separate post. For now, I’d recommend this post. When conducting the interview, the most important question you can ask is what are your biggest challenges? 

This will give us ammunition to WOW the hiring manager later on. 

2. Briefcase/Pre-Interview Project - Once you have the pain-points, spend 3 to 5 hours researching this problem. Then you’ll package this research into a doc or slide deck to send to the hiring manager. Document should contain: 

• Pain-Points

• Project Ideas

• Resource Requirements

• Time estimated

• Prioritization 

When you send this to the hiring manager, do this tactfully. DO NOT expect anything in return. Although you’ve spent time thinking about their problems, they do not owe you anything.