Gary Vaynerchuk creates 100 pieces of content a day to fuel his digital empire. Can the average creativepreneur pull this off? Let’s find out.



This blog post May contain referral links.  I don’t recommend stuff that my clients and I haven’t loved on our creative biz adventure.  I will receive a modest credit to my account should you love these tools and apps as much as I do!

The Orbital Pull of Gary VAYnerChuk

By now, I’m sure you’ve heard the motivational and often-sobering truths of social media marketing from none other than digital marketing master Gary Vee.  From keynote speeches (my personal faves) to podcasts to IG Stories and YouTube, this guy is EVERYWHERE.

And once you enter the Gary Vee universe, you are sucked into an orbital pull of relentless content on all platforms.

Dare I say, homebody is omnipresent.


So how did Gary Vee get so big online?

  • He is an early adapter to digital technologies:  Gary got his start leveraging Google Adwords and SEO practices to build his family’s wine and spirit business back in the early 2000’s. He later invested money and time into thoughtfully produced YouTube videos designed to educate, inform, and build online sales.
  • He “ate shit for years”:  His words, obviously, not mine.  It took years of consistent and cohesive marketing on platforms many people had yet to adopt to become the brand name that he is today.  His own father laughed at him when he wanted to start a wine tasting channel on YouTube.
  • He listens more than he talks: A big part of Gary Vee’s strategy is to do a whole lot of social listening and then let his audience help inform the content he creates. He also responds personally to Tweets and IG comments to build his audience in a meaningful and thoughtful way.  Gary has communicated great disdain for folks who leave their audience hanging by not responding to public comments.


“Stop focusing on dumb shit. Don’t be afraid to break things. Don’t be romantic. Don’t take the time to breathe. Don’t aim for perfect. And whatever you do, keep moving.” – Gary Vaynerchuk



The Impetus

I can definitely say that I am a better content strategist for having stuck Gary Vee’s messages into my earholes on an almost daily basis. 

I typically cast YouTube from my phone to my TV, and listen to his impressive body of keynote speeches at industry events, or queue up his bite-sized podcast and video segments in a playlist on topics relevant to what I’m working on, like growing my LinkedIn or making my content voice-search friendly.

One ongoing topic that continues to strike me is that he produces 100 pieces of content to post on social media Every. Damn. Day.

Take into consideration that VaynerMedia has 800+ employees across the United States and United Kingdom.  He’s got plenty of staff support to help splice and dice his videos into well-packaged segments for both podcast, social stories, and YouTube videos.

Also take into consideration that he owns and operates a straight-up marketing and branding agency, so he has all the good equipment, staff support, and editing software to bang out content, fresh and daily. 

Let’s throw in the fact that he has years upon years of expertise and experience in successfully honing his craft and achieving his vision.

I am but one Luca, and while I do not have a dedicated videographer trailing my every move (mostly from couch to kitchen, how exciting) and even despite the fact that my video and audio equipment cost me under $100 at this current juncture, I believe there is a lot to be learned by embarking on the almost overwhelming task of a content creation blitz at my skill and expertise level.



The GAry Vee COntent Strategy

Gary Vee knows the value of multi-tasking each individual piece of content produced.  Here are just a few of the ways he puts his content to work:

  • Gary Vee creates a big piece of “pillar content”:  For him, this is his daily GaryVee Video Experience, hosted on his Facebook Page.  For me, this is likely going to be my blog while I rebuild my content distribution infrastructure and shift from blog to video.
  • Gary Vee then repurposes his “pillar content” into smaller bites:  His daily video is broken into smaller segments for distribution on on his YouTube channelFacebook Watch Page, and IGTV.  His other “pillar content” is his podcast series, which is then distributed to his iTunesOvercast, and Stitcher.
  • Gary Vee reserves “micro-content” for his social channel:  After building out the big stuff into smaller pieces, he then turns key quotes, concepts, and take-aways into shareable pieces of micro-content on InstagramSnapchatLinkedInQuora.  The goal is to build awareness and drive traffic back to the original long-form pillar content


The Gameplan

For the sake of this challenge, I am considering 100x pieces of content to be original content that I have created, not content reshared.  I am also including any personal content that I have created on my personal accounts that brings brand awareness  to Creative Enabler.  



  • Original pieces of content: Images, Video, Audio, Text, Downloads, Whitesheets, Presentations
  • Existing original pieces of content that I have previously created and are being repurposed in a new way will count towards the 100x
  • Embellishing or adding my own twist to a graphic, picture, or video someone else took and changing its meaning or context by over 50% to make something new will count towards the 100x


  • Reshares of other peoples’ articles or content will not be counted towards the 100x 
  • Sharing original content to groups online is not considered a piece of content (That’s distribution, son)
  • Content that I create for my clients (And there’s a lot of it!) will not count towards my 100x


The Infrastructure

Every ambitious idea requires a modicum of thoughtful analysis and strategy, and for this seemingly insane self-imposed challenge, I must first establish my goals, take inventory of what I have in my toolbox to pull this off, and plan to pivot as needed.


Goals for this Challenge: 

Surprisingly, it’s *not* necessarily for me to hit 3,000 original pieces of content over the next month or so, but to make more quality original content and a better workflow for my content distribution

The goal for me is to aggressively rebuild my content strategy and distribution methods by doing the work to make a meaningful change to my digital marketing efforts.   

I want to make a nice, meaty, value-rich blog post or video and break that baby down into bite-sized hunks of Creative Enabler goodness across a number of platforms.

I want to saturate you in what I have to say.

One of my goals for my content marketing in 2019 is to actually show my audience how to do the work, not just tell them how to build a content strategy and send them on their way. 

This self-imposed challenge is helping me hit other goals that I previously set with my business.


Current Creative Enabler Content Stats:



I would say 75% of what I share on my social channels is reposted content from other sources, and the rest of my content is engaging questions that I pose to my audience (polls, etc.) and original content, including blog posts, video, stories, images, and photography.

This challenge will definitely help me improve that ratio of sharing more of my original content without skipping a beat on the consistency front.


Inventory of Infrastructure

In the words of the immortal Jake Blues, I’ve got everything I need…almost.   Here’s what I’m starting this challenge with:

  • Website on WordPress CMS & Divi theme
  • I am recording video with 2x Samsung Galaxy S8+ cell phones
  • I am using a Lenovo ThinkPad T420 that is loyal af but has seen better days (R.I.P.,  I Key)

Wired Lavalier Mic:

Selfie Light with Cell Holder:

Inventory of Tools/Apps

Thankfully, I already am locked and loaded on my tool/app front and will not have a foreseeable learning curve:

The MInDset

As I indicated above, this challenge is really about reworking my existing infrastructure so that I can make meaningful moves with my audience growth and brand authority by leveraging my expertise and personality, and ultimately, my bottom line.  

This will also allow me to explain a process I often teach in my workshops, but have not shared in a “behind-the-scenes” or “step-by-step” format for those who learn best by watching a strategy in motion.

This self-imposed challenge is not about “being held accountable”, a phrase that is so overused online it makes my eyes roll back into my head every time I read it.  

I have an accountability buddy; It’s called my bank account.

I’m putting this online for you to watch, listen, and react to so that perhaps my efforts can help you gain new insight into how to tackle your own content marketing and self-promotion in 2019.

I am approaching this from a “Document, Don’t Create” mindset, as this will give me room to adapt my message, explore, and be in the moment.  


    The LUCA C. Content STRATEGY

    Stay tuned for the next blog post on this journey where I will share my content strategy for this mission.  I will be hashtagging posts related to this challenge #garyvee100 on Facebook, Instagram, LinkedIn, Pinterest, and Twitter.

    It looks like there’s a 100x pieces of content over 100 day challenge inspired by Gary Vee with the hashtag #garyveechallenge.  That’s all well and good, but I’m going to do this my way.


    Want to follow my progress?  Come and join the conversation in Creativepreneur Happy Hour.

    No Fake News(letters) 

    #JustTheTips is not an elaborate sales pitch masquerading as a resource for creative entrepreneurs.  

    Get microdoses of achievable inspiration weekly, revealing the mindset, strategy, and business infrastructure of successful brands.