My $1,000 Weight Loss Bet – 11 Weeks to Lose 44 lbs



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The past 18 months have been incredibly busy with signicatly more attention and focus on the trajectory of my career (and thus finances) then on my own health & fitness. Part of the reason that I set a workout goal and nutrition goal was to try to play defense against the carnage to my waistline that was coming. I tend to work in boom and bust like cycles when it comes to my career, and when things are really booming, the buttons on my pants start busting :).

Although I have been getting workouts in, they have not been given the intensity they deserve, but more importantly the nutrition side of the equation was way out of wack. It is true when they say that abs are made in the kitchen, not in the gym. I know this first hand because this is not the first cycle that I have experienced like this. I feel like this post deserves a bit of a preamble of how we got to present day.

My Back Story

I grew up a chubby kid and really didn’t get much exercise until I reached high school and made the conscious decision to exercise and get fit. When I was in high school I started lifting weights and running 5-6 days a week. I read every book related to health and fitness that I could get my hands on. I also became and avid subscriber of Men’s Health as a freshman in high school. By the time I was a sophomore in high school, I could no longer be described as the chubby kid, in fact I would have described myself, and probably did, as really lean (but not quite ripped).

Now that I had a body I wasn’t afraid to show off at the beach or poolside, I decided to join the swim team. The swim training schedule along with school cut out my extra time I had for lifting. But 2-3 hour practices 6 days a week kept me in tip top shape. With so much more training time, my body needed more calories to keep it running. As I mentioned briefly above, I had always struggled with weight as a kid, but I was now in a sport that allowed me to eat whatever I wanted without any weight gain. I am sure some of you reading this now can remember those days…Oh the good old days!

So I graduated high school and went onto college where I kept swimming for the most part. The college I chose to attend did not have a swim team, so I competed through USA Masters swimming. Although I didn’t train nearly as much as I had in high school, I still remained in decent shape. But the story really starts when I finished college and entered the so called “real world”.

I graduated college at 6′ weighing 190lbs, but within three years I had ballooned to 240lbs. I couldn’t believe it when I saw that number on the scale in January of 2011.

I had completely lost touch with the healthy lifestyle habits I had consciously created as a freshman in high school. When I was in high school I actually thought one day I might go on to be a personal trainer and I vowed that I would never lose my health and fitness again. I remember having numerous conversations with my aunts and uncles warning me that it was easy as an adult to lose sight of your fitness. And of course being the know it all teenager that most of us were, I would argue “that will never be me”. Hmmmm was I way off or what?

How did this happen? Well I ended up not going the personal training route and instead got my bachelor’s degree in Finance. After graduation I went on to work for a big oil company and slowly but surely the weight started packing on. It came on slowly at first and then I would go through periods of hitting the gym to lose some of the weight only to gain it all back and then some after I had stopped. Sound familiar? I also never adjusted my calorie intake that was elevated when I was swimming competitively. I was going to fancy dinners and out for cocktails with co-workers…leaving me in a constant state of calorie surplus, which simply equals WEIGHT GAIN!

It was no mystery to me, I knew I was gaining weight and that it was my own lack of attention to my health and fitness…but I found every excuse in the book not to workout.

The more weight I gained the more lethargic I became. I was once again that “Fat Kid“.

It was time for CHANGE! I kept promising myself that I would get in shape “someday”, but someday never comes, there is only Monday through Friday.

Finally in May of 2011 when I stepped on the scale and it read 240lbs (again the same number I saw in January of 2011), I was now ready to live up to the promise I had vowed never to break in high school. Finally armed with real motivation I made the commitment to do P90X, yes that workout program that you have seen on the infomercials. This set off a 22 month streak and obsession with health and fitness.

Below are the before and after pic’s of what I was able to do in about 250 days, and that I maintained for almost 3 years.

P90X Transformation

I went from 240lbs with 28% bodyfat down to 187 lbs with 9% bodyfat.

Coming back to present day…

November of 2012 was really the month I can look back to and see the start of the gradual decline. I started skipping workouts and then I started to get really sloppy with my eating habits again. Being the data junkie that I am, I had been keeping score all along by jumping on a scale almost daily, and the results confirm my intuition. Below is the historical trend that I get from my Withings Scale that syncs to the Withings app on my iPhone.

2011 - 2016 Weight Trend

At my leanest in September of 2012 I weighed 188.8 lbs, and that was the trough of my weight loss (that was 51.2lbs from peak to trough, over 17 months). Do you like how I worked in some terms that most use to talk about investments :)?

Back in those days I set an intervention value at 220lbs. I didn’t want to let myself ever get back to 240lbs again, well you can see from the chart above that I recently jumped right past 220 and hit a high of 228.4lbs on 10/7/16. I decided it was time to make a change, luck had it that I was at a leadership retreat, and a coworker of mine needed some extra motivation to get her own weight back under control. She also tends to work in booms and busts. One night at dinner we decided to not only hold each other accountable, but to also put some real stakes up with a $1,000 bet.

My latest side hustle???

Details Behind The $1,000 Bet

We both want to lose at least 20 lbs (minimum) and since she is a female and we are doing absolute weight, I agreed to give her a 5lb handicap. Being the gentlemen that I am, I will not divulge her starting weight, even though no one will no who I am talking about, you never divulge a ladies weight.

  • If neither of us lose at least 20lbs the bet is off, meaning no one gets paid. We liked the idea of a high water mark.
  • As I mentioned above, she will get a 5 lb handicap, which really means that if she loses 20lbs I will have to lose 25lbs to be equivalent.
  • The final weigh in is 12/21/16 (the bet was made on the night of 10/6/16, making this an 11 week bet)
  • The prize is $1,000 for the person who loses the most weight.

Throughout the 11 weeks we have both agreed to check in twice a week with each other on Mondays and Fridays. This will serve as a sense of accountability for each of us. During each check in we will share our current weight.

My Plan of Attack

First, I should state that my official goal is to drop 43.4 lbs in 11 weeks. I have never dropped that much weight in such a short period of time. In the story that I shared above I dropped 51.2 lbs, but that was over 250 days.

I know it’s possible, because I have read stories of others that have done it. But it takes a hell of a lot of planning and discipline. It is very easy to figure out how to do it mathematically from a calorie standpoint. In it’s simplest form, weight loss is all about creating a calorie deficit. In wealth building the secret is to spend less than you earn. In weight loss the revers is true, you want to spend more calories than you consume. But the idea is the same, it is all about creating a gap.

One pound is equivalent to 3,500 calories.

Based on my goal of losing 43.4 lbs, I am going to have to lose 4 lbs a week, which I think will be easy for the first 3-4 weeks. Mathematically speaking, that means I need to create a calorie deficit of 14,000 calories per week or 2,000 calories per day. This will be accomplished through calorie restriction (i.e eating a lot less food) and high intensity workouts (HIIT style training paired with strength training).

The first thing to do is to figure out your resting metabolic rate (the amount of calories you burn to basically just be alive). I have a long formula set up in a spreadsheet that I found on some fitness blog a long time ago, it tells me that my resting metabolic rate to maintain 228 lbs is 2,200 calories (it takes into account gender, height, and weight). The short cut to arrive at your own resting metabolic rate is to take your current weight multiplied by 10. This number is just for essentially being alive. But then you need to adjust it based on your activity level (see table below):

Activity Level

Since I workout 3-5 days a week on average, I will be using a 1.55 multiplier. Therefore when I take the 2,200 calories X 1.55, it brings my total daily calorie expenditure (TDEC) to 3,410 calories in order to stay exactly the same. That passes the sniff test, as I estimate I have been consuming 3,400 to 4,000 calories per day on average.

Now I can back into my daily calorie target by taking the difference between my TDEC of 3,410 and the required calorie deficit of 2,000.

In order to reach my goal I will need to take in 1,408 calories per day. This is a bit larger of a deficit that I have run in the past, previously the largest deficit I ran was 1,500 for a sustained period. If I find this too hard, I will adjust it up to 1,910 calories, but it will slowdown the weight loss (but should still amount to about 38.5 lbs).

My Personal Guidelines/Rules

  1. Replace one meal a day with Shakeology (the best shake on the market in my opinion)
  2. Meal Prep on Sundays for the entire week (plan all meals)
  3. Follow workouts as subscribed (using a combination of beachbody workouts;Insanity, Asylum, P90X)
  4. No Processed Carbs (carbs should only come from veggies, except on cheat day).
  5. High protein (very dense and filling)
  6. Unlimited Veggies (nutrient dense, hunger is usually a sign of your body searching for nutrients it’s lacking)
  7. Drink lots of water (when your dehydrated, your body mistakes hunger for thirst)
  8. 1 Cheat day per week (inspired by Tim Ferris, author of 4 hour work week)

In addition to these rules I also have the following contingencies in place if I fall behind my plan. If I am behind goal, then an additional workout is required. I will also be required to use the app myfitnesspal to track my calories. In the past I have been pretty good about estimating it, but something this sever may prove difficult.

If I am within 1 lb from goal then I have the option of doing either a 3 mile run or a 20 minute insanity workout I have called “Fast & Furious”. If I am behind by 1 lb or more than I have the choice of a 5 mile run or “Insanity Sports Conditioning”.

Last But Not Least…The Tracking Table

Being the data junkie that I am, of course I need a systematic way to track and record my progress. So, I created the spreadsheet below:

Weight Loss Tracking

I have only shared a portion of the tracking sheet in the essence of space on your screen. You will notice that I set this up as a daily tracking sheet, and have pre-calculated my daily target weight in order to achieve my goal. As I am writing this I am currently down 6.10 lbs and am 2.71 lbs ahead of schedule. (I only had to be down by 3.39 lbs by this day). The goal is to be as aggressive as possible for the first 4 weeks.

You may be wondering what the “$ Value” column represents. This is the cumulative cost/reward of each passing day of this 11 week challenge.  The way I look at it is that I am not only going to win but I am getting paid to lose weight. Each day is worth $13.16!

I will plan to do another update to this plan in November to give everyone an update on my progress. I am sharing this on the blog as another form of accountability. It is amazing the amount of pressure you can create by sharing and announcing goals publicly. I really don’t want to let myself down, but more importantly I don’t want you let you my readers down.

One of my core beliefs whether is wealth building or weight loss is…THE PATH IS ALL MATH!!!

-Gen Y Finance Guy

Gen Y Finance Guy

Hey, I’m Dom - the man behind the cartoon. You’ll notice that I sign off as "Gen Y Finance Guy" on all my posts, due to the fact that I write this blog anonymously (at least for now). I like to think of myself as the Chief Freedom Officer here of my little corner of the internet. In the real world, I’m a former 30-something C-Suite executive turned entrepreneur turned capital allocator. I am trying to humanize finance by sharing my own journey to Financial Freedom. I believe in total honesty and transparency. That is why before I ever started blogging, I decided that I would share all of my own financial stats. I do this not to brag, but instead to inspire motivate, and also to hold myself accountable. My goal is to be a beacon of hope, motivation, and inspiration, for you, the reader, by living life by example and sharing it all here on the blog. My sincere hope is that you will be able to learn from me - both from my successes and my failures! Read More



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12 Responses

  1. Great you are taking some serious action here! Sounds like you are going about it with a lot of knowledge, I’m sure you’ll be successful.

    I’m finally starting to take my mobility seriously rather than buying into the limiting belief that I’m not flexible. Starting by measuring a few moves to keep track of progress (not quite as simple as a scale) and a daily MobilityWOD video:

    1. Hey Brian – I have done it before, just not in this short of a time period. Just like wealth building it is not rocket science, it is simple disciplines that are easy to do, but also easy not to do.

  2. This should be easy for you. Just stop going out to eat. You will drop pounds and save thousands of dollars. Win/win. Gl!

    1. Sue – Your right, I hadn’t considered the savings we would realize. We should save at least $500/month if not $1,000/month by not eating out nearly as much.

      Thanks for the vote of confidence!

  3. Wow you’ve been able to do some amazing work with P90x. I didn’t have a lot of success (it’s probably cause back then I played tennis and that made me eat a lot more than I should.. two and a half subway foot long sandwiches in one sitting plus room for dinner? How did I live?!).

    I’ve heard of wages on weight losses but I haven’t checked it out yet. Hoping for the best for your challenge!

  4. I love a challenge!

    You had some massive deltoids when you were in fighting shape!

    I understand how weight creep works. I’m about 170 lbs now at 5’10” after being ~165 for 15 years in a row. I’m trying to get back to 160-165, but I’m failing.

    But I’m determined by end of year! Having an extra 5-15 pounds of weight is terrible for the knees and for tennis. Slows me down!


    1. Hey Sam – have you heard of In addition to this $1,000 challenge I joined a few challenges there that add a bit extra motivation.

      Maintaining your weight for 15 years is great. That is my goal after getting back into shape, putting a system in place to maintain that level of fitness. I don’t need the booms and busts anymore.

  5. Do a Cyclical Ketogenic Diet. By far the hardest of all diets, but also the most muscle sparing. If you have the discipline you should easily be able to hit those numbers with only moderate exercise.

  6. Nice work here on the accountability using $$.. That’s intense, 50 pounds or around 30 kg’s (being an Aussie) in 11 weeks..

    Looking forward to hearing how that goes and would be cool to read a series on your mindset and practicalities of this? If it hasn’t been written already 🙂

    1. As I respond to your comment I have 24 days to go in the challenge. When you get to the next goal check for October you will see an update on my progress.

      I will plan to write a full post mortem and share my plan going forward.

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