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TLDR; Three months ago I used to weigh 250 pounds. Yesterday I finished my 3rd 100+ mile bike ride and weighed in at 199.4 pounds. This is my story.

I am the Kingpin… Apparently

It started about 4 months ago, mid-Aril 2019.  I hadn’t seen a dermatologist in several years.  In order to make sure the doctor could see “everything”, I prepared the night before by shaving off my iconic beard.  At first this change was fun seeing the newly exposed skin below, but then my kids all freaked out… 

Dad!  What happened to your beard?  No!  You don’t look like you. You look like Fiske, the Kingpin, from Spiderman. 

I looked in the mirror in horror, they were right.  I tried to not let it bother me, and I played along.  I put on a black shirt and a necktie and took a photo of myself similar to a screenshot from the video game.  And although I did Photoshop the lighting and background, I did not photoshop my face in any way.  I shared it with family and friends for a good laugh.  But, deep down inside, it hurt.  A lot.  

Why have I always been “fat”?
Why can’t I just be normal?

Karma’s a Bitch

I had a sudden memory of when I was a young kid, probably around 6.  I touched my Mom’s belly and asked if she was going to have a little brother for me.  No, she wasn’t.   Mom, now I understand how that childlike honesty made you feel.   Mom, I’m so sorry.

So, in having this moment of awakening, I sent her an email apologizing for my 6-year-old comments. This started a deeper conversation around how we both have struggled with our weights our entire lives. But she told me something that challenged my deep-held beliefs.  She told me that I was never fat as a kid.  Wait, what?  At first I brushed it off in disbelief.  I have always been the “fat kid”, ever since elementary school, or as long as I can remember.  I’ve always had this negative impression of myself that I’m fat, and I’ve carried that idea with me since childhood. I don’t know exactly why, I just have.


This strong cognitive dissonance really messed me up for several days.  Could I have been fundamentally wrong about my self-image all those years?

Finding the Truth in Photos

I pulled out my childhood photo album and started looking through it.  It was hard for me to believe at first, but my mom was… right.  I didn’t look fat… I looked, dare I say, normal.  I had a tough time processing this.  I couldn’t reconcile the difference between what I’ve always believed and what I was seeing for myself, now, 30+ years later.  

What was wrong with me?  What was wrong with my self-image, thinking I’ve always been fat when I was clearly not?   More importantly, how did I actually become obese anyway?

Did I, in some way, actually cause this for myself though an infinite loop of negative comments echoing in my head?  By telling myself for all those years that “I’m fat” did I somehow cause it to become true over the next 30 years?  I don’t know, but I’m done with it.

If a mindset filled with incorrect beliefs can cause this obesity, then I can change what I think, and I can change who I am.

The Webb Diet

It started around May 1st.  I decided to try my own eating plan.  I had done this in the past with short-term success.  It allowed me to lose weight while still being able to eat all the stuff I loved.  The reason I had failed before, was because I never thought I could be anything else but fat.  That was changing.


The Webb Diet is simple:

  • Eat less than half
  • Drink only water.

The Power of Intention

I also started to practice all the “power of intention” techniques that I’ve learned over the years from people like Wayne W. Dyer and the movie The Secret.
  • When I showered in the morning I would take time to just stand there while the water ran over my body, and imagine what it felt like to look down and see over my flat stomach to my strong legs.
  • I would look in the mirror, pull my stomach in, and try to imagine my fit body.
  • When I drove to/from work, I would tighten my abs as long as I could so that I could feel the sensation of not to have my stomach resting on my legs.
Being able to visualize my new body was SO tough, because my self-image has been distorted for so many years, and my current reality reinforced that image. When I looked down and saw the flab of a belly that has been there my entire life, how could I possibly imagine anything else?  This was really tough.

Initial Results

After the first week of dieting and visualization I was seeing great results; I was down 7 pounds.  I knew that most of that was a combination of water weight, and pooping out all the extra food that was still in my system.  However, with those encouraging results I thought, “what else could I do to help accelerate this?”  I did occasional set of pushups or sit-ups, but it wasn’t enough.

My wife Sharon had just finished running the Colorado Half Marathon in Fort Collins.  I really, really dislike running.  However, I’ve always enjoyed biking, so I thought maybe I could start commuting to work on my bike again.  Maybe that would help accelerate things.

Biking Begins

For the last 3 weeks of May I started to bike to work and home a few times, but I was pretty out of shape and it was tough.  It took me 53 minutes to go 8 miles, for a pathetic average of 9mph… each way, lots of hills.  I skipped a lot of days because I was scared that I’d either not get there in time, or not have the energy to do good work after I got there.  Baby steps.  I had to start somewhere.

The Game-Changer

On Friday May 31st, I had a pretty rough day at work.  It was probably the closest I’ve ever been to leaving my job. Ironically, that Monday June 3rd, I had taken the day off so Sharon and I could celebrate our 24th anniversary.  We had lunch together and I tried to enjoy the day, but I had too much pent up anger and energy.  I was feeling like I didn’t really have control over my life and I needed to do something crazy that would give me the feeling that I could grab the bull by the horns again.

This is when I decided to try a 30-mile ride to downtown Denver.  In my mind it was little crazy.  It was a 3-hour bike ride, when the longest I had ever ridden was 1 hour.  The view of the downtown skyline was just a spec from where I lived, which challenged my perceptions, again. Needless to say, completion of that ride opened up a new world, and reset what I thought I was capable of accomplishing. 

Bike to Denver - An Unexpected Journey

Doubling Down on New Eating Habits

After accomplishing my 30-mile ride, I had a renewed sense for eating well.  I was curious to compare what I used to eat with what I was currently eating, and I quickly understood what I was doing wrong.  The reality is that I was eating way, way, way too much food. Let’s be honest, a handful of peanut M&M’s is fine. A can of Coke is fine. A bagel or breakfast burrito is fine. Eating them multiple times a day, day over day, was my big problem.  This renewed my faith that portion control was definitely working well for me.


Daily Eating habits
  • Breakfast: Homemade Egg McMuffin, or Bacon/Egg/Cheese bagel.  A large mug of decaf coffee with sugar and half-and-half. 400-550cal
  • 2nd Breakfast: After getting to work, on Fridays they’d have free bagels and/or breakfast burritos. I’d often have 2x. 400-800cal
  • AM Snack: Some sort of pre-packaged snack like trail mix, a bag of chips, or a granola bar. 250cal
  • Lunch: A large left-over portion of dinner from that week, or frozen meal. Can of Coke.  500-800cal
  • PM Snack: 2nd can of Coke. Another pre-packaged snack: chips, granola bar, trail mix. 200-400cal
  • Ongoing Snack: Our work also had an unlimited supply of peanut M&M’s, so I’d randomly grab a handful here and there through-out the day. 100-200cal
  • Dinner: Whatever homemade meal our family prepared: Spaghetti and meatballs, BBQ ribs, almond crusted chicken, tacos, chicken tiki masala with naan bread, Friday night pizza, etc.  I would eat over-sized portions. Often, I would also finish the food that my kids wouldn’t eat. 600-1000cal
  • Night Snack: Watching late-night TV shows with my oldest son Apollo. Often we would eat half-bag of tortilla chips, a half-jar of salsa, and I’d drink 1-2 Mike’s Hard Lemonades.  300-700cal.

The Next Challenge: 50 Miles

The next two weeks I biked to work 2 days a week and I was feeling a little bit stronger now.  So I decided I wanted to set an even crazier goal.  What if I did 50 miles?  That would be crazy, right?  So I planned a trip to bike to Fort Collins for Saturday June 15th.  I did it!  Sharon meet me up there and we had lunch afterwards.  I was absolutely and completely fried, and the last 10 miles were painful and exhausting.  I learned afterwards that I almost bonked, but luckily I didn’t.  Of course, “bonking” was a new phrase that I learned after experiencing this ride.  I had accomplished my goal, but I felt like I had hit another barrier.  Maybe 50 miles was my limit?

July started, I was down 30 pounds, and something transformative happened.  My commute to work was like an Altoids mint, it suddenly felt curiously strong and refreshing.  I hit hills with a vigor that had felt tedious before, and almost every ride I set a handful of new PR’s.  My 10-mile commute now seemed almost insignificant in effort to the perspective of a 50-mile ride.  

At my fastest, I had gotten my commute time down to just 35 minutes from 55, and my average speed increased from 9mph to over 16mph.  I was blown away by my progress and re-encouraged that what I was doing was working.  It was time to face my fear of going past 50 miles.  But how?

Research for Longer Rides

I started doing some research about how to properly fuel for long bike rides.  I learned that I needed to be eating 100-200 calories every hour in order to keep the sustained energy for the calories that I was burning.  That definitely explained why I almost bonked on my ride to Fort Collins, since I had barely eaten anything.

But I had trouble with this new information about fueling. 100-200 calories an hour means I’d be taking in an extra 400-800 calories! 


My ambition to bike longer distances was now at odds with my primary goal of losing weight.  AGH!

I looked at this situation similar to the adage “you need money to make money” in that perhaps “you need calories to burn calories.” Okay, I was willing to trust the advice and give it a try.

On July 6th, I planned a route out to Fort Lupton, down to Brighton, and home again.  Instead of eating a Cliff bar, I got turned onto RxBars which seemed to contain less processed and more natural ingredients.  I ate a half of a bar every 30 minutes, about 200 calories an hour, so I always would have energy.  It worked perfectly.  After 57 miles I returned the loop home and felt as good as I did 4 hours earlier, and I was excited to feel that I could have kept going if I wanted to.   I had broken through another barrier.  I was no longer scared of passing 50 miles.

The next week my commute was ON FIRE, riding 3 days in a row and feeling strong.  However, I decided to take off on Thursday and Friday to get ready for my biggest challenge yet.  Could I do 75 miles?  Now that I had a working “fueling” plan while I was riding, I wanted to see how far I could push it.  I planned a route to return to downtown Denver, but this time loop around the Cherry Creek Reservoir, and end with a full ride down the Cherry Creek Trail.  Well, I did it, and it was AWESOME.  I felt great the whole time, and again I was excited to feel that I still had energy left and I could have gone farther.

Overcoming the Fear of Hills

I knew that I was close to being able to ride a century, the holy grail of bike riding and a goal that has been on my bucket list for years.  However, I needed to do one more week of hard training to be sure.  A hard week it was.  I biked to work 3 days that week, doing longer routes, biking in the pouring rain, dropping my iPhone off the bike and shattering the screen, and having a bee fly into my helmet and sting me on the forehead.  Ugh.  With all that work, I wanted something special for the weekend ride.

I was still intimidated by hills.  How could I break through that mental limitation?  I knew I could go 50 miles, so what if I biked 50 miles up the side of a mountain?  What if I biked to Idaho Springs?  Crazy, right?  Over 4000ft of elevation gain including a single sustained climb of 2000ft over 12 miles.  Compared to my 600ft gains on my commute rides, this was pretty terrifying.  If I could do this ride and conquer my last fear, then I knew I would be ready for my first century ride.

I did it!!!  Well, sort of.  During the exhausting climb, I missed a turn for refilling my water bottles.  I got caught 10 miles short of my goal without any water, so I decided to stop early.  Even though I was short, I accomplished what I had really wanted:  I overcame my fear of long, steep hills.  I now knew that I could do my 100 mile ride.

Riding A Century

The following week I spent most of my time planning the route for my first century, trying to find a route that I thought I would be achievable.  I found a small town to the northeast called Fort Morgan that had minimal elevation gain, and planned out my route with all needed rest stops.

The night before the ride, our family tradition of Friday pizza night was well welcomed in all it’s carb-filled glory.  I even treated myself to TWO pieces of pizza, when I had spent months training my eating habits to just have one.  It was a rare, but purposeful treat.

Nutrition and Hydration Plan

The day of the ride I woke up at 4am.  Honestly, I was awake before that, but just quietly laid in bed trying to get back to sleep with no success.  Had a nice bowl of steel cut oatmeal with brown sugar, cinnamon, blueberries and raspberries.  I gathered my my day’s prepared nutrition: an assembly of Rx Bars, Larabars, a few Gu gels, 2x bananas, a peanut butter sandwich, and some other high-carb snacks.  I wasn’t sure what I was going to be in the mood for, so I over-packed on purpose a combination of real food and pre-packaged food.   I was able to put all my goodies into the back pockets on my biking jersey for easy access. Paranoid of being stranded without hydration, I strapped 3x extra Gatorade drinks to the back rack of my bike, just in case.  Spoiler alert: bungie cords didn’t do their job.  My apologies to the people who had to clean up my bottles… wherever they fell off.

My First Century Ride

The ride was great.  I started off strong and other than getting a flat tire in mile 43, I was making great time and felt great through mile 60.  The tough part was the upcoming 30-mile stretch between Kersey and Wiggins, with no services in between.  At an average pace of about 15mph, that’s two hours straight without being able to refill water bottles.  It didn’t help that I got a 2nd flat tire around mile 69, while surrounded by mutantly-huge grasshoppers. After fixing the flat, I was horrified by the continuous sounds of crunching as I couldn’t avoid running over hundreds of them over the next 10 miles.  Sorry little guys.

Maybe karma was paying me back, because around that time I started to have bad gastrointestinal issues.  My stomach felt horrible, and I didn’t feel like eating anything.  I knew this was going to be a big problem because I HAD to eat 100-200 calories every hour or else I would bonk, and bonking in the middle of nowhere would be very, very bad.  I forced food in my body, and even though I had dropped to a 12mph pace, I pushed on and finished my first 100 mile bike ride.  I did it.  I freekin did it!

Self Deprecation… Continued

I had done it, but barely.  My wife Sharon told me that now I was an athlete, as this was on-par with running a marathon.  I had trouble really believing that I was an athlete. That term was reserved for people with ripped bodies, olympians, super-stars… right?  Could I really be an athlete now, even if my BMI classified me as “obese”? Maybe, but my physical success still didn’t feel real. It felt like a flash in the pan, or lightning in a bottle.  I wasn’t comfortable with it.

The next weekend, I decided to bike another century.  Sharon thought I was crazy and I should take at least a week off, but I couldn’t let it go.  I planned another route around downtown Denver, and set the goal at over 120 miles.  I talked with several experts including my multi-Ironman brother-in-law, to get more information about long-term fueling on super-long athletic events.  I took this new information and implemented it.  When I arrived home 9 hours later, I was tired but I had done it again, and felt great.

Believe it or not, I was still having a really tough time grasping that I could actually be an athlete.  I couldn’t let it go, so just yesterday I did yet another ride for 110 miles.  While I didn’t make it the full 130 I had planned, I was satisfied with what I needed to know: 100-mile rides were now entirely possible.

Wrapping It Up

A Changed Man

This morning I woke up and weighed in at 199.4 pounds.  I had now officially lost over 50 pounds and weigh under 200 pounds for the first time since high school almost 30 years ago.  My BMI was now out of “obese” and into simply “overweight.”  This was the final piece of the puzzle I think I had been missing.  I had done it.  I had challenged a life-long belief that I was fat, and that I was always going to be fat.  As a result I changed those beliefs, which changed my actions, and changed my reality.  I can exercise for 6-8 hours straight, traveling over 100 miles.

Okay, I am now an athlete.

Next Steps

So, what now?  My goal used to be 185 pounds.  I still plan on getting there, but I’m thinking about changing the goal to be 165.  At 165 I would technically no longer be “Overweight”.  That would truly be another barrier to break through.  Also, Sharon now challenged me to start running.  Perhaps I could run a 5K, 10K, Half-Marathon, or heck even a FULL Marathon.  Who knows?   Luckily, now I know what I need to do to get there.

Thank You to my Patrons

Thank you to my Patrons on Patreon for your support.
Pathfinder: Jay Kimble
Rock Star: Sharon Pickersgill