From left to right, author and Gary Vee. All images courtesy of author.

Gary Vaynerchuk is Don Draper meets Tony Robbins meets Ritalin. The wily, hard-talking entrepreneur is the chairman of VaynerX, a “modern-day media and communications holding company,” and the acting CEO of VaynerMedia, a “full-service advertising agency servicing Fortune 100 clients.” Renowned for his rants, advice, and energy, Vaynerchuk’s also a motivational speaker, author, and influencer, with millions of disciples scattered across Instagram, YouTube, Facebook, and Twitter.

The guy’s schedule is more of an algorithm. There are no warm ups or cool downs. Everything is preplanned and precise. He’s been known to schedule three-minute-long meetings, and doesn’t eat during the day to save time.

His chaotic schedule varies day-by-day, but the template stays the same. He launches out of bed at 5 AM, exercises, and then works from 7 AM to 11 PM. During the week, Gary Vee, as he’s known online, doesn’t touch fun with a 100-foot pole. He has no appetite for booze, chillin’ out, naps, TV, sports, procrastination, or aimless Facebook scrolling. Anyone or anything stopping him from becoming the Greatest, Most Admired Entrepreneur of All Time is put in the crosshairs of a rant, tweet, Snapchat story, or blog post. It’s this type of intensity that’s turned him into the king of hustle culture.

I admired Vaynerchuk’s message. His lifestyle was cool and exciting and edgy. He got whisked around in Ubers, wore tight shirts, starred in daily vlogs, and said stuff like “reverse-engineer,” and “predicated on.” As an experiment, I tried to keep pace with him. Every day for one week, I pledged to work 16-odd hours, sleep five, and exercise for one. (Vaynerchuk says 30% of his time is spent travelling, so I allotted an hour or so to commuting).

I don’t advise for huge companies or give speeches, so I superimposed The Gary Doctrine onto my own student schedule. I’d follow His Commandments as closely as possible: I vowed not to relax, drink, chill with friends, go on social media, procrastinate, nap, fire-up Netflix or watch hockey. In other words, a Complete and Total Embargo on Fun. Every second would be filled with writing, university work, meetings, or exercising.

To get into character, I got the same short, aerodynamic haircut as Vaynerchuk, copied his outfit, filmed a Daily Vee_-inspired vlog, recorded a podcast Q&A, walked really fast, and swore a _shit ton. I even started to learn Russian on Duolingo, Vaynerchuk’s mother tongue.

I attempted, as best I could, to get inside his head. Here’s what happened.

Monday

Vaynerchuk claims he’s “not a morning person at all,” but he rolls out of bed at 5 AM. He skims through news, hits the gym, transitions into Work Mode, and then bulls on until 11 PM.

As I slipped into character, I felt the last scraps of my sanity melting away. I had gotten Vaynerchuk’s short prison haircut on the Friday prior, which, along with my tired, ocean eyes, made me look like the understudy to Justin Bieber’s 2014 mugshot.

After polishing off an article, I headed to the gym to confront Vaynerchuk’s morning workout: a super-quick, super-intense stir-fry of chin-ups, curls, and stretching. His Spotify playlist reminded me why, exactly, I was in an empty gym doing quadruped thoracic twists at 7:30 AM on a Monday morning.

In addition to “eating perfectly,” Vaynerchuk apparently fasts all day because he “doesn’t get hungry.” I tried a 20-hour fast but my willpower had been stretched to its limit by the pre-dawn workout, the elaborate staging of a Vaynerchuk-styled photo-op, and 17 hours of work.

When I got home that night, adrenaline and exhaustion met and mixed, giving me the same sort of smouldering buzz you get after pulling an all-nighter. It felt great, but I knew it wouldn’t last: I was getting the runner’s high on day one of seven—my brain was congratulating me for finishing, but I was barely out of the starting block. I collapsed around 11 PM.

Tuesday

Gary Vaynerchuk’s vocabulary is half of what makes him so interesting. Stuttering, mumbling, and stumbling are foreign to him. His rants have been viewed millions of times, making him one of the most popular motivational speakers on YouTube. His style blends the repetition and melodrama of a sermon with the cadence of ’90s rap. More than anything else, his rants sound like Jonah Hill’s slam poetry in 22 Jump Street:

Slam... poetry. Yelling! Angry! Waving my hands a LOT! Specific point of view on THINGS! Cynthia! Cyn-thi-a! Jesus died for our sin-thi-as! Jesus cried, runaway bride. Julia Roberts! Julia Rob... hurts! Cynthia! Ooh, Cynthia. You're dead. You are dead.

Just carpet-bomb in the market and micro vs. macro and it could pass as one of Vaynerchuk’s monologues. His speeches are inspiring, though—his rough, random sentences tend to slam into you like runaway trains. For instance, when asked about people who “don’t necessarily subscribe” to his Hard Work Ideology, Vaynerchuk exploded:

“They’re gonna lose, they’re gonna lose, I don’t give a fuck about them. They’re gonna lose. They’re gonna rent their suits and drink their champagne. And I wanna remind everybody, just because you put ‘entrepreneur’ in your Instagram title doesn’t mean that you’re a successful entrepreneur!”

He’s direct, crude, and unflinching—three qualities that make him very popular online.

I started parroting his buzzwords ( reverse-engineer, R.O.I., predicated, and curse words galore) on Monday, but it felt phony. Realizing I had to go deeper, I decided to carve 20 minutes out of every evening to learn Vaynerchuk’s native Russian on Duolingo. I managed to get “hello” on lock, and can recite any combination of “good evening/afternoon/morning, that is my radio/bicycle/house.”

After I got Vaynerchuk’s lingo down, everything else started to fall into place. My eyes were half-closed during my Tuesday evening lectures, but my bursts of wild-eyed participation seemed to impress the professors. And even though I couldn’t hang out with my friends, I enjoyed silently typing next to them at the library. It was just the lonely one-man stand from 8 AM to 11 PM that made me question the whole thing.

I ended up falling asleep in my clothes after a 19-hour day.

Wednesday

Vaynerchuk’s lifestyle feels like being shot out of a cannon. The guy has speed and endurance: constant, quick bursts and fourth-quarter composure.

So far, the mornings have had a sky-high R.O.I. Finishing a Medium article, workout, and essay before noon has been a great pattern to fall into.

The afternoons are a different story.

There’s a saying that those who “rise like rockets are apt to come down like sticks.” Vaynerchuk flies through the morning, but he does not come down.

I could not harness such energy or discipline. After launching out of bed at 5 AM and charging through the morning, the post-lunch come down was devastating.

Between lectures, I crumpled into a chair and had a sinful 20-minute nap. I regretted it right away, though, and asked Him for forgiveness.

I hoped my 14.5-hour work day would compensate for it.

Thursday

Gary came to me in a dream and told me to work my fuckin’ face off. That was enough to shock me out of my sleep and propel me through the morning and afternoon. No more naps.

Apart from the night terrors, the most terrifying part of this challenge is that Vaynerchuk refuses to walk anywhere. He lives in New York and, rightfully so, Ubers to every meeting.

As the head of two multi-million dollar companies, he’s forced to . I’m the editor of a campus satire paper and I have 12 hours of class per week. The stakes aren’t as high, sure, but the Lyft fares, sadly, are the exact same.

Oddly enough, Vaynerchuk’s 43rd birthday was on Wednesday. I cranked through my day so quickly that I missed it. To celebrate, I poured out some water and sipped it down during my Russian lesson: за тебя, Gary!

Friday

Gary Vaynerchuk is best known for his Daily Vee vlogs. His right-hand man, David Rock (known as D-Rock), shadows Vaynerchuk, and records the never-ending cycle of meetings, rants, workouts, Uber trips, conferences, and speeches.

I recreated Vaynerchuk’s look (a green New York Jets jacket, joggers, and ever-present earbuds), and recruited my friend Max to film a low-budget Daily Vee remake. Trying to imitate Vaynerchuk, with all his energy and ego, proved harder than the 20-hour day itself:

By 8 PM, we were both delirious from stress and strain. The University of Toronto campus looked like Hoth, we had run out of money from Ubering everywhere, and our friends, a short walk away, were wondering when we were coming over to start drinking.

But the forecast called for three more hours of workin’ our fuckin’ faces off.

We vetoed The Fun: beer, loud music, and hanging out make up the first three levels of Vaynerchuk’s Inferno, and I knew that if I caved, I’d never forgive myself. Instead of partying, we recorded a mock AskGaryVee podcast, requesting and answering questions from our Facebook friends. We zonked out at around 1 AM after a long, loud day.

Weekend

There is no Sabbath with Gary as God. He devotes Saturday and Sunday to his kids now, but Vaynerchuk said that, between the ages of 15 and 30, he didn’t go out once. There is absolutely no way this is true, but I went along with it.

Unsurprisingly, the final two days turned out to be just as tough and bland as the first five.

I did, however, schedule one of those three-minute meetings with my friend just so that I knew what it felt like. And since I had 36 hours of free time, I was able to reflect on the week as a whole.

I thought that after the challenge I’d be a highly-fulfilled superhuman, but, at the end of it all, I just feel like a tired guy who hasn’t seen his friends in seven days. The results weren’t as mind-boggling as I expected them to be, and my memory of the week is coloured more by what I missed than whatever I gained from 100 hours of “hustling.”

It was a week filled with adrenaline, but not much else. I didn’t have genuine conversations with anyone: nearly everything I said was communicated at meetings, whispered across library desks, or yelled through earbuds. My tired, vacant eyes and constant swearing didn’t make me any friends, either.

I did finish loads of readings and essays, and my Medium audience skyrocketed from all the articles I published. People seemed to really enjoy my political pieces, especially the chatty brigade of new friends I met on the Russian Duolingo forums.

After publishing what would be my last article on Saturday night, I raced home from the Starbucks that had acted as my war room for the week. Because I only did 10 hours of work, I knew I’d have to return the next day.

Stopped by a red light, my mind drifted to who, exactly, would qualify as Vaynerchuk’s Evil Opposite—the Cain to his Abel, the Stalin to his Roosevelt. I settled on Ferris Bueller, whose motto was “leisure rules,” and who put more energy into getting out of work than Vaynerchuk does putting into it.

As the light turned green and I lurched across the street—sides aching from quadruped thoracic twists and eyes heavy from five hours of sleep—Bueller’s famous quote floated into my head: “Life moves pretty fast. If you don’t stop and look around once in awhile, you could miss it.”

I took my time getting back to Starbucks on Sunday.

End of Week Statistics

Hours worked: 94

Coffees consumed: 30

Time spent hanging out with friends: 18 minutes

Time spent watching Netflix, hockey: 0 minutes

Time spent aimlessly scrolling through Facebook: 38 minutes

Sleep per day:

Naps: 2

Final essays finished: 2.5

Pages of university readings completed: 400

Time spent in class: 12 hours

Articles on Medium published: 12

Workouts: 6

Meetings: 11

Three-minute meetings: 1

Ubers/Lyfts taken: 10. $40.11

Times I deeply regretted this assignment: 100+