How I Gained and Lost 60 Pounds as an Entrepreneur — and So Can You!

Welcome to the less-talked-about underbelly of “killing it” and “crushing it”. And your ticket out.

A before and after that was 30 months in the making. Left: speaking at Refresh D.C., November 2011 (34.1% body fat). Right: Gussied up in ‘Rent the Runway’ attire for a girls’ weekend in Vegas, April 2014 (21.8% body fat). If you are what you measure, then consider me more concerned about my body mass index and ratio of muscle-to-fat than what the scale tells me. My 2015 goal is to get to 18% body fat, which is considered a “fit female athlete”. As for losing weight? Nah. I’m losing inches and gaining strength.

Six years to gain it, 30 months to lose it, and a lifetime to keep it off. While weight is the central focus of my headline and photos, it isn’t really the point. Rather, the weight gain and damage I was doing to my health should be seen as manifestations of an overworked mind and body, and underfed soul.

If my story helps just one entrepreneur or ambitious ladder-climber / jungle-gym-swinger avoid (or come back from) unhealthy habits, then I consider sharing my very personal journey a success.

Skiing Diamond Peak with my mom and dad, circa 1985 (Lake Tahoe, NV).

Growing up, I was a multi-sport athlete and a hard-charging gym rat in my early 20s. Thanks to good habits instilled in me by my parents, I always ate healthy whole foods (many of which we raised / grew on our farm), drank lots of water (and nearly zero drops of caffeine), and made sure to get plenty of sleep. But after moving to Washington, D.C. after graduating college, my healthy routines started to fall away in favor of carving out more hours in the day for my career ambitions.

Two years into living in D.C., I started my own company with my then-boyfriend. Any vestiges of my good habits went out the window. And I took off on the ride of my life.

While executing ground-breaking work in the data visualization space, winning countless industry awards, and generating $13 million dollars in revenue (without any outside funding), I put on about 10 pounds a year. For six years. This works out to one pound of weight gained for every $216,667.00 (gross revenue) we made.

Oh, but wait, there’s more. As if the weight gain wasn’t enough, I had a laundry list of health issues that ranged from poor skin, to perpetually ‘on-end’ nerves, to frequent “file not found” moments when my brain tried to take on certain tasks or access my vast Latin-powered vocabulary.

As a professional problem solver skilled in the art of follow-through, I finally hired myself to do what I do best: get results. Over the course of 30 months, I took my life back. I got healthy. I meaningfully re-engaged with my sister, mom, dad, and close friends. I got back my kick ass vocabulary and brain power. And I shed nearly 60 pounds.

As you read on, I want to underscore two things:

  • There were many factors that contributed to my weight gain and unhealthy habits. I will call-out the major ones and allude to the minor ones. If even one of these factors sounds familiar, I implore you to get ahold of it now before it gets any worse.
  • There were 30 months and many steps that I took on a daily basis to “get my life back”. Detailed at great length in my contribution to The 10 Habits of Highly Successful Women, I’ve chosen to highlight the most important health-based factors here. TL;DR: a plan, prioritizing yourself, consistency, patience, and a commitment to “forever change” are key.

Seven steps to guarantee that you will gain weight while building your company (or your career). Additionally, these are great for eliminating healthfulness, happiness, and joy from your life.

1) Put yourself dead last. Work comes first. This includes clients, customers, employees, new business leads, industry press, consumer press, and requests from your co-founder or boss. If there are any hours (or minutes, honestly) left in the day, give those to your family, loved ones, and friends. But above all, if you want to ensure you will gain weight over time, do not — I repeat do not — carve out time for your health, any outside-of-work interests, sleep, or proper and consistent nutrition.

Presenting at the Economist’s “The World in 2011" summit, December 2010. Although stoked about the forum and topic (global economic opportunity for women), I was running on only three hours of sleep from the night before. Photo credit: Taylor Davidson for The Economist.

2) Speaking of sleep, take pride in not needing much (any) of it. Insist on only needing four hours of sleep a night (or go for broke and pull all-nighters… frequently, and maybe even in succession). Wear this “superhuman power” like a badge of honor, and make sure to let people know that you will “sleep when you are dead” and that “sleep is for quitters.”

3) And while you are at it: stop any personal care activities. This includes, but is not limited to: showering only when absolutely necessary (working from home does not constitute necessity); don’t drink enough water, keep your stress levels high, and don’t get enough sleep (#2 above) so your skin goes to hell; miss haircuts for months, years even; cease any sort of waxing activities [think: Frida Kahlo]; work from home, wear sweats (if you even elect to put pants on), and stay “focused” (a.k.a. sedentary) for as many hours as you can; and do not, I repeat DO NOT participate in any sort of physical activity (#4 below).

4) Exercise? Just in case you were thinking about doing it…don’t. This includes restricting any and all physical activity (even just walking). Make sure to schedule every waking moment of the day with meetings or work sessions. And make sure these work sessions entail as much sitting as humanly possible, for as business innovator Nilofer Merchant posits in an HBR article that went viral “Sitting Is the Smoking of Our Generation.” And if you think you can get in a workout at some point, start checking and responding to email so that this urge passes. Remember: there will always be one more thing you can do that can keep you from the gym, a run, or a pickup game of soccer with friends.

5) Outside of a few minutes, do not make uninterrupted time for friends, family, or loved ones. Be so busy that you aren’t there for them when they need you. When you do happen to get to get together or talk on the phone, make sure you are multitasking so as not to miss a beat with your work — and so as not to not really hear a word they are saying. This can take the form of incessantly checking / being on your phone; taking calls that interrupt your time with them; thinking about your work while they are talking; and talking about your work issues in a one-sided way.

6) Be too busy to eat, until it is too late and you opt to eat ALL THE THINGS. This is a particularly important step toward an unhealthy lifestyle and guaranteed weight gain, so you will want to pay attention.

First, when you wake up (provided you even went to bed), reach for some sort of caffeinated beverage before any water or food. This will ensure that you surpress your appetite, throw off your metabolism, and delay hunger for a few hours. If you do in fact get hungry again in the morning or early afternoon, just go for more caffeine.

Second, by the time you head into the afternoon / early evening, you will start to notice symptoms of hunger that can range from drawing a blank when trying to think or recall, to being irritable or “hangry” if you will, to even having sharp pains in your stomach. At this point, go for the nearest delivery menu you can access (thanks to Seamless and services like it in many cities, there’s even an app for that!) and order as many dishes that sound good, including appetizers and desserts, and drink some more caffeine as you wait for it to arrive.

Finally, once the food is delivered, consume it by inhalation and avoid chewing too much. Also when you start to feel full, keep going. Who knows when you will eat again?!

7) Cease all extracurricular activities (especially the ones that bring you any sort of joy). This includes, but is not limited to: reading books, traveling for pleasure and not for work, learning about non-work-related things that interest you, reading the news, keeping up any hobbies like writing or knitting or playing an instrument, meditation, practicing your religion, mentoring others, and much more!

Remember, you need to squeeze every second out of the day and you absolutely cannot give up any temporal ground to such things.

So which of those seven are you guilty of? If the answer is none, then I salute your ability to find and keep balance. If the answer is one or more, here are seven steps to help you stop, take stock, and make some simple, yet powerful, changes to get you back on track.

Seven steps to guarantee that you will lose excess weight or maintain a healthy weight while building your company (or your career). Additionally, seven sure-fire ways to be happy and live a joyful life.

1) Plan the work, work the plan. To reclaim my health (and waistline), I created a project plan for my life that structurally followed the way I scoped a statement of work for a client. It included a realistic timeline, key performance indicators (“KPIs”), and discrete deliverables. The timeline was two years. The milestones were body fat percentage, how things fit, how I felt, and how I looked (requires a commitment to recording in a journal to see the progress). The deliverables were commitments I was making with myself.

I also realized I needed outside resources to execute my plan. I hired an executive coach (Karen Vander Linde!), a trainer (Deemsy Arias!), and a clean food delivery service (Clean Food Miami!). The least I could do with some of the money I made while treating myself so poorly was reinvest it in myself. These three investments saved my important relationships, my mental well-being, my physical body, and my overall health.

In particular, Karen’s role was one of not just mentorship, but one of weekly accountability. With her guidance from 2011–2012: we identified the systemic issues needing improvement, A/B tested a variety of new approaches — and when certain issues were unresolvable with respect to the management style of my co-founder at JESS3—she was instrumental in helping me plan and execute a responsible and professional exit from a company I built and ran for six years. To this day, Karen and I remain close and toast frequently to our successful mission.

My departure from JESS3 meant leaving my life in D.C., heading briefly to LA to see through my duty of setting up the team for success, and moving onward to help build a text-to-video startup in Miami. But what happened outside of my new Florida-based job was perhaps the most transformative.

If Karen helped me change my mental state in D.C., Deemsy helped me change my physical state in Miami. I referred to him as ‘coach’ — which harkened back to my highly competitive sport-playing days. When I wanted to quit or move on to a new lift or circuit, he would say: “Now we are really cooking with oil, let’s keep going.” He also helped me “clean up” my diet (literally, figuratively). He said bluntly to me once I rattled off how I was eating: “You have good intentions, but bad execution.” If there is one thing I pride myself in, it is my execution. So I took this very seriously and immediately adhered to a 90 / 10 ratio of clean, paleo eating to the very occasional ‘less clean’ eating.

Now that I am in New York City, I miss Karen and Deemsy dearly, but their voices and encouragement ring in my ears anytime I want to give in or give up.

2) Timeline: Be realistic and know that depending on your starting point, this might take years, not months, and not weeks. And then a lifetime after that. For 30 months, I worked my plan every, single, day. And to this day, I still work that same plan.

PSA: I am pretty sure people know that fad diets at best give you temporary results (Oprah once famously said of her liquid diet days: ‘I was a size 6 in the studio, then I looked at some food, ate something solid, and was up to a size 10 by the time I got to my car’). And at worst, they give you false hope that it only takes a few weeks and some magic supplement. The real secret? Be patient and be consistent.

3) Key Performance Indicators: body fat, clothing, feelings, appearance. Unlike any other “diet moment” in my life, I got away from the number on the scale as the main determinant in my success. And I suggest that you do as well. Why? Because in order to overhaul your metabolism permanently, you need to build muscle. Muscle-building requires protein and weight lifting.

Lifting heavy on leg day, November 2014. Surrounded by professional models (no, seriously) at my Manhattan gym, I went ahead and leg pressed 270 lbs x 8 reps; 360 lbs x 8 reps; 450 lbs x 6 reps. When asked by a passer by after I finished my final set: “What are you training for?” I replied: “Life”.

If the scale is your main metric, you are incentivized to do a lot of cardio and starve yourself, neither of which are sustainable (and arguably, to paraphrase my good friend and fellow lifter-entrepreneur-UChicago alumna buddy Julie Fredrickson, these are activities of a “renter” who makes superficial upgrades, while a “buyer” makes remodel upgrades that last).

Even more to the point, a pound of muscle takes up much less mass than fat and looks great in any circumstance. I firmly (pun intended) believe: STRONG IS THE NEW SKINNY.

4) Discrete deliverables: more sleep, more water, lots of exercise, limited unhealthy beverages and foods, reasonable work hours, and regular non-work activities. ALL THE THINGS CONSISTENTLY. There are a few more deliverables I went after, but these were my foundation. I even grouped them together in my “Elementary Happiness” talk at HubSpot’s annual conference in 2013.

  • Sleep: at least eight hours every night.
  • Water: at least 90 ounces a day.
  • Diet: five meals a day, protein and fiber, with some complex carbs (e.g., quinoa, whole oats, sweet potatoes). In terms of caloric intake, I recommend consulting a nutritionist to set a reasonable target for your age, gender, and weight goals (e.g., losing, maintaining, replacing fat with muscle). That’s what I did!
Of course you want the best conditions and gear, but you won’t always have it. Don’t let that be an excuse. Ever. In 2013, I forgot my tennis shoes while on a business trip, but I didn’t let it stop me. I threw on what I had (knee-high boots) and still pumped iron. I travel with the TRX band, weight gloves, and tennis shoes (when I remember) so I can be ready to do body weight, gym, or outdoor training.
  • Exercise: at least five times a week. Must include a combination of aerobic and anaerobic activities. I am a big fan of HIITs (high intensity interval training) and weight-lifting circuits that rotate muscle groups each workout. What do you like? Figure out what you like doing and do it for 45 — 60 minutes every day (e.g., running, team sports, hiking, walking, spinning, yoga, etc.). Walk to your meetings if you live in an urban area (and winter isn’t an excuse, just bundle up!). Go to classes. Hire a trainer to jump start you. Have a buddy to hold you accountable and make the time pass faster.
  • Cheat foods: sugar and simple carbs should only be consumed in a pre-planned, moderate way during a weekly “cheat meal” and that’s it.
  • Caffeine: minimal and not for appetite suppressant or to jump-start an over-run system. Only for the taste and ritual a few times a week at most.
  • Alcohol: none. Say whaaaa? Yep. None. My exceptions are life event celebrations with very special people. As a partner in my family’s pinot noir vineyard, this feels blasphemous. But to truly see results, it is a must. After you’ve reached your maintenance zone, go ahead and bring it back. But in serious moderation.
  • Curiosity and expression: what did you love when you were younger? Or in college? Painting? Drawing? Reading? Learning new things? Writing fiction? Taking trips not for business? Hiking? Camping? Get these things on your calendar and cultivate them just for you. While it feels like a potential drain on your “all day every day” work calendar, taking these steps in fact increased my creative abilities and recharged me for better execution at work.

5) You are likely not in the life-saving business, so draw lines about your work hours. One of the sure-fire ways to burn yourself and others out is to always be “on.” Just like a “hero” mentality emanates from the “non-sleepers,” the “super responders” and “24/7/265’ers” love to proudly flex their “always-on” badge.

Only I could end the cycle and I did so by not responding to emails after 7pm; if I had the urge, I saved it as a draft and sent first thing the next morning. In the rare occasion that it was in fact urgent, I would hop on the phone and resolve it so I didn’t get stuck in a game of email-tennis. If I had a work product that needed to get done, I set aside focused, non-interruption hours and got it done (as opposed to bouncing around from tab to tab, conversation to conversation, with lots of fits and starts).

6) Don’t sweat the small stuff. And it’s all small stuff. I am not advocating that you ignore the details, but I am insisting that you put your work-centric approach into perspective. Is what you are working on worth snapping at employees or family members? Worth not sleeping? Worth gaining 60 pounds? Worth spinning up your team on a weekend when they should be re-charging so they can come back strong on Monday? Very rarely is the answer yes to any of these things.

7) This is for life, not just for now. The second you think “I’ve made it to my goal, now I can finally stop all these healthy mind / body things” is the second you risk slipping back into the awful habits that robbed you of your health and vitality. This is a commitment for life and one that you need to make sure is sustainable; I recently came across a great guide from Precision Nutrition thanks to fellow-entrepreneur-buddy Ellie Cachette. Check it out as you evaluate what’s sustainable for your goals and for what makes sense for your schedule.


Happy, healthy, loving my new team at my new job, engaged in my new home (New York City), and dressed to take on any situation. Backpacks and tennis shoes are essentials! I call this my “urban turtle” mode, November 2014.

At the end of 30 months, I not only regained my mental health, but I also replaced lots of fat with lots of muscle. All told, I dropped 58 pounds and shed 12.3 percent off of my body fat. I fit into clothes that I wore in high school (which my sister kindly reminds me: doesn’t mean I should wear them, as fashions have changed since the 90s). My skin, hair, and teeth look and feel like I’ve gone back in time to my youth without surgery. I take on the things I love (like writing) with a renewed sense of purpose and energy. I give my most important relationships the time, focus, and respect they deserve. And my ‘playbook’ is chock full of tools, tips, and tricks to ensure I never get that far afield again (FYI: said ‘playbook’ is in the text above, shared with you in hopes it can serve you in the ways you need).

So there you have it. Seven steps to a better you. Do I religiously follow each and every one, every single day? No, but I aim to at least 80 percent of the month. And if I want to push to new levels of strength and trimness, like I do in 2015, then it is closer to 90 to 95 percent of the time. A few other examples of when upping your game past the 80 percent mark might help you get to the other side with ‘flying colors’: when you are going through a difficult time; when you are preparing to and following the act of giving birth; or when you are transitioning geographies.


In the end, even when I thought I operated outside of laws of nature, there was a very real level of deterioration of my abilities that noticeably occurred over time. I was less sharp after not sleeping, which meant I had to work twice as long to finish tasks, which meant I had to stay up late working, which meant I didn’t ever get enough sleep. It’s a vicious cycle and to be at my best mentally and physically, I had to put an end to it. Over two years ago, I did just that.

If you take one thing away from my story, let it be this: The “sleep when I am dead” or “eat right and exercise once I sell my company” mentalities will surely speed up your death, make the years you live more miserable, and be costly in time and money to overcome the longer you subscribe to them.

I hope you get started today so that your future self (and everyone who cares about you) will thank your present self. Because it is never too late to change everything.


Timeline of Companies Built, Activities Done, Weight Gained / Lost

1993 — present: Co-founder and partner at bootstrapped Bradshaw Vineyards.

  • Year-round weight training and varsity letters in volleyball and softball in high school; played basketball from 6th — 10th grade
  • Weight training and long distance running in college
  • Farmhand for our family’s 95-acre farm, of which 44-acres is our pinot noir vineyard (“Bradshaw Vineyards”)

2006 — 20012: Co-founder, COO and President at bootstrapped data visualization agency JESS3.

  • Gained 60 pounds over the course of 6 years; this works out to be approximately 10 pounds per year or $216,667.00 gross revenue generated per pound of weight gained
  • Awarded: Inc 500 x 2; AdAge Small Agency of the Year, southeast; Inc 30 Under 30; Fast Company ‘Most Influential Women in Tech — Executive’
  • Daily doubles (cardio / weights) for six months and change in diet and habits; lost first 15 pounds before departing in late November 2012

2012 — 2014: Founding team member and COO at venture-backed text-to-video startup, Guide.

  • Lost 45 pounds
  • Awarded: Fast Company ‘Most Creative People in Business’

2014 — present: New York Managing Partner for London-based product innovation company, Made by Many.

  • Inspired by and learning from my teammates on a daily basis
  • Happily maintaining balance, following my own advice
  • Working out 6x a week
  • Pushing for some new strength and body fat goals in 2015 — stay tuned!

In my monthly newsletter “Professional Excellence” launching on December 5th, I plan to drop knowledge like a book bag with holes in it.

Please consider subscribing: https://tinyletter.com/LeslieBradshaw.