How Gary Vaynerchuk Generates $100 Million Every Year

28 Dec. 2022


  • [Tip 1]: Gary Vaynerchuk’s 100 Million Business Strategy Reverse-Engineered

  • [Tip 2]: What VaynerMedia’s Sales Funnel Would Look Like If They Hired Me

  • [Tip 3]: Gary Vaynerchuk’s Crazy Content Marketing Plan Explained


This article is for online business owners and marketers who want to figure out how Gary Vaynerchuk uses content to fuel his multi-channel, entrepreneurial machine that ultimately brings in over $100 million in revenue each year and learn how to apply those same funnel principles to their own products & businesses to increase conversion rates and revenue.


Side note:


I have never worked for or with VaynerMedia or Gary Vaynerchuk. Everything in this article was created from my own experiences and research with Gary’s brand and company. Also, Gary’s brand and marketing changes often and rapidly, so keep in mind that by the time you read this some of this may be dated.

[Tip 1]: Gary Vaynerchuk’s 100 Million Agency Strategy Reverse-Engineered

In order to understand how Gary builds awareness and revenue, you first need to understand why GaryVee does what he does.


You need to get the big picture…


I got this from an interview on Impact Theory:


I want to be the poster child of the person who built the biggest, baddest empire and did it by being a good dude along the way.”


Gary wants to turn entrepreneurship into something cool, and he wants to inspire current and future wantrepreneurs to take risks and try to build billion-dollar businesses while being the kindest person on the block.


He wants to be the rockstar of good-guy business — to trick the business world into being a kinder place. To leave a legacy.

Got it? Great.


Next up is figuring out how he is fulfilling and funding his mission, and that question can be difficult to answer.


GaryVee does a lot..


He’s a serial entrepreneur, motivational speaker, agency director, content creator, angel investor, and more. He has mastered diversification.


But, I’d argue his true differentiator lies in his ability to produce and distribute content. GaryVee creates multipurpose content that brings in leads to every part of his “empire.”


In other words..

Gary Vaynerchuk is the KING of Repurposing Content

Gary is the master of taking content and spreading it around to a multitude of different outlets with appropriate context. It’s viral lead generation at its best.


GaryVee is all about approaching attention as a precious commodity, and he’s going to do his damndest to get it.


But how does he manage to do that without getting burnt out?


He chose his best medium and stuck with it…


Gary is really good at video content. He recognized this and hired a videographer to follow him around all the time to record his life and general awesomeness. They find viral moments, edit them down, and repurpose, repurpose, repurpose.


Here are just a few of the platforms Gary is active on:



Gary takes videos and sends them to all of his platforms while keeping the platform’s style and personality in mind. He changes the caption or thumbnail to better fit the medium, and that’s the key…


He also lets people find his content on whatever platform they prefer.


Take his podcast for example..



Crazy, right?


It doesn’t matter what you use. If you want to find GaryVee, you can. And after you’ve engaged with any of his awareness, viral content, he pulls you into his retargeting campaigns via paid social advertising, continuing to bring you into Vayner’s world and maximizing the exposure of each piece.


We’ll cover more on his distribution and repurposing and how you can apply it to your online business later.

Gary Vaynerchuk Always Promotes Virality

Every single piece of content GaryVee puts out is built for sharing. Every post, link, blog, podcast — you name it. Instead of pointing people toward email signups or additional content downloads, GaryVee always asks for the share.


While there’s no doubt this strategy has helped him get to where he is today, there are definitely opportunities for growth… which I’ll cover in a bit.

How Gary Vaynerchuk Monetizes His Audience

GaryVee wears a lot of hats, and his revenue streams are diversified. With this in mind, Gary’s monetization strategy and value ladders (for an overview of value ladders check out my VideoFruit case study) depend on the customer avatar, but he has 3 main segments & value propositions:


  • Wantrepreneurs or current entrepreneurs (books, events, and consumer products like shoes)

  • Small to medium-sized businesses (SMB consulting services at 10k a pop w/ an exclusive community “VaynorMentors”)

  • Fortune 500 Marketing Clients for VaynerMedia (multi-million dollar marketing projects & retainers)


All of the marketing GaryVee does fits into each of these three verticals in a pretty fascinating way..


By tying his personal brand to VaynerMedia and demonstrating his expertise through his own business, he’s able to attract massive companies that are searching for the best while training people under him to help the multitude of current and future SMB entrepreneurs he inspires and reaches with his viral content.


Everything sort of blends and swirls together, and once a customer identifies themselves as a particular avatar they are directed to the appropriate channel.

GaryVee’s Value Ladder:

With this framework in mind, let’s focus in on his SMB business value ladder


Here’s how GaryVee approaches SMBs:



By focusing almost all of his attention on his lead magnets, he brings in consistent inbound leads to his other, more lucrative services by expanding his personal brand.


Smart, right?

How Gary Vaynerchuk Continues to Build His Legacy

As you’d expect from Gary, he doesn’t stop with the revenue he’s generating from VaynerMedia. Instead, he chooses to reinvest that cash into projects he cares about. From investing in tech startups (Facebook, Uber) to buying companies like PureWow and sponsoring musicians & influencers, Gary aims to build a legacy that lasts by diversifying his portfolio and interests. He wants to create his own distribution network that is uniquely GaryVee.

Main Takeaways:

  • Pick your business’s best content medium and focus on that.

  • Tie your personal brand to your business if applicable.

  • Establish your value ladder.

  • Grow your brand through complementary diversification to reduce content load.

[Tip 2]: What VaynerMedia’s Agency Funnel Would Look Like If They Hired Me

Okay. Now that you get GaryVee and know what he stands for, let’s get a bit more specific on what I think he does well and what he could do better.There is no arguing that Gary is one of (if not the) best in the world when it comes to viral content and high-level brand awareness content. As we talked about, GaryVee does a great job repurposing and spreading his viral content around, and there’s nothing I (or anyone else) could teach him.


But, GaryVee optimizes all of his content for maximum exposure — possibly to a fault.


Everything is built around sharing at the moment, and he has only a limited amount of places for leads to take the next step.


As you know from running or working in your own business, capturing an email address is often the key to building a sustainable audience, and Gary’s opportunities for an email capture are pretty limited.


You can sign up for his weekly newsletter (sent out every Monday) on his homepage:


You can sign up on the sidebar of blogs:



Or you can sign up for his First in Line VIP messaging service:



That’s it. No content segmentation or upgrades.

For example, this is how he ends a recent blog post:



Sure, it’s on brand and inspirational, but he could be growing his brand insiders faster.

Suggestion #1: Include more specific content upgrades to increase opt-ins.

Considering the sheer amount of people who read and interact with GaryVee’s content, it’s amazing they don’t take advantage of content upgrades more.


The first thing I would do is link every blog post with a relevant content upgrade.


By pointing people toward a lead magnet directly related to the blog, we can capture their email and send them specific content based on the problems they’re facing and goals they want to achieve.


Once we have an email address, we can control the conversation.


Gary wouldn’t have to depend on Facebook’s algorithm to share anymore, and we could target specific segments directly with advertising and email.


If your funnel conversion rates are lower than you want, I guarantee lack of specificity and context are part of the problem.

Suggestion #2: Build a two-step segmentation process.

Gary is building an empire, and he needs to know exactly what types of people are responding to what types of content.


Sure, you can guess based on the content they converted on. But why not ask and qualify people at the same time?


Without customer information, your content is running blind.


Let’s define his segments in a bit more detail.

Gary’s customer segmentation buckets:


  • Students who don’t know what to do with their lives.

  • Wantrepreneurs who want to start a business but don’t know how.

  • People trapped in a 9-5 and are unhappy with their job.

  • Business owners who want to grow their business to next level.

  • Brick & mortar businesses (restaurants, etc) who want to get started with digital marketing.

  • Fortune 500 enterprise businesses.

  • The hustlers and make money fast people — making a quick buck online.

  • Marketers interested in learning social media (since he’s the king).

  • Large companies wanted to modernize their digital presence.


Now we should add a lead bucketing option during sign-ups using condensed versions of these segments.


For example, if someone is on one of Gary’s blogs coupled with one of our new and relevant content upgrades, they could decide to download the accompanying materials.


The next screenshot is from the last case study we did on VideoFruit.

Once they click, a segmentation form appears.



The key to creating a good form survey is to create the survey to be focused on their goals and common problems.


For Gary’s avatars, these could be:


I want to accelerate my small business through viral marketing but I don’t know where to start.” (for his SMB audience).




I run a multi-million dollar company and am looking to work and learn from the best marketing minds in the biz.” (for his enterprise clients).


You could also create a survey that segments people based on the services they are trying to sell like so:



Make sense?



Suggestion #3: Enroll segmented audiences into a multi-channel, evergreen funnel.

Once someone opts-in to the GaryVee community and automatically segments, themselves, we need to establish a relationship and trust.


We can build this trust and install beliefs with a multi-channel, evergreen system:


Channel #1: Evergreen Email Sequence.Channel #2: Bot Sequence (separate from Gary’s First in Line).Channel #3: Facebook Ad Retargeting Funnel.


Email is the key to controlling Gary Vaynerchuk’s audience. He can use these emails to install the most critical beliefs before asking for a sale or upsell.


What is the most important belief to install with this evergreen sequence?


That Gary Vaynerchuk is the baddest badass entrepreneur of them all.


People need to want to be like Gary.


By sending the best content Gary has to new subscribers in the form of 7 evergreen emails and triggering more engagement opportunities through bots and retargeting ads as they move through the funnel, new leads will understand who GaryVee is and why he does what he does in the context of their specific segment (SMB vs. Enterprise vs. Wantrepreneurs, etc.).


Enterprises won’t want to hear “start your own hustle” inspiration. The same way wantrepreneurs won’t find “How viral marketing grew this $10 million dollar business to $100 million” as interesting as startup marketing. It works both ways. The beauty is with segmentation we can send them the exact content we know they’ll like.


With this information in hand, we can begin to control the conversion timing and sell moment based on dynamic engagement tracking, or lead scoring (offered in most CRMs).



The goal is to get people’s lead scores in your CRM up high enough to be ready for the conversion event.


Once we know who they are, what they want, and how engaged they are, we can begin the next step.


We use Wild Mail for all of our tracking & funnel triggers and love it.


This is our funnel tools stack to build a sales funnel that converts at 8%

How I Would Further Monetize Gary’s Audience:

Once they hit a certain score based on actions (opened 4 emails, watched 3 videos and listened to two podcasts, etc.), we can dynamically trigger the next step using our ESP and/or CRM.




That next step is to aim for a sale using the same multi-channel configuration.


In other words, I would sell specific products based on funnel engagement & customer type using the same tools we’ve already set up.


By using the bot sequence, Facebook advertising, email, etc., we can say things like: “Hey, I noticed you were interested in learning how to hustle a business from $0 to $10,000 in revenue in under 6 months. I actually wrote a book about exactly that. It’s only $10, and it was a New York Times Bestseller. You should get this book if you want to take things to the next level.”


As long as you show social proof, touch on those beliefs installed in the emails (most badass ever etc.), and speak to their specific problems identified in the segmentation process, it will work.


For example, check out this excerpt from the first email in an automation sequence we have set up:



Try thinking and writing out 3 beliefs you need to establish from the get-go with your own audience. Then take those and implement them into any of the early funnel experiences someone has with your brand.


We can also turn these funnel pieces off or on based on whether they buy or don’t buy etc. using custom audiences in Facebook and more.


And then, depending on their avatar, we can continue upselling the next piece. So with GaryVee, if they’re a SMB I’d offer the VaynerMentors or Enterprises consulting services.


Even though Gary acts like he hates selling, he sells all the time — he has to. And selling is a good thing. Gary helps his customers make more money and build the lives they want, and I’d approach those sales with that in mind.

What happens after Gary’s Evergreen Funnel?

I would…


  • Continue optimizing for maximum exposure (encourage shareability).

  • Use an evergreen newsletter (not broadcast style) with a mix of old and new content (increase frequency above more than 1 per week).

  • Retarget existing audiences with new or unbought offers via TruView & Facebook.

Main Takeaways:


  • Establish beliefs and answer objection questions early.

  • Match your content with a relevant content upgrade.

  • Allow your customers to segment themselves through a two-step form.

  • Send your customers specific content based on their avatar.

  • Let their engagement determine the speed at which you sell.

  • Always offer the next step you’d like customers to take after they complete an engagement action.

[Tip 3]: Gary Vaynerchuk’s Crazy Content Marketing Plan Explained

We talked about how GaryVee is the king of content marketing and repurposing. He’s everywhere, or at least it seems like it. But, once you break down the processes he has it becomes much more realistic to replicate in your own business.


He basically has a bunch of content habits and tricks he and his employees use all the time.

Habit #1: Gary Edits Video Content Differently Across Platforms

Gary always fits into the platform for better engagement. Even if the content is the same, his team changes the cropping and copy to better fit the medium. In his words, it’s “context”. For Instagram, these videos are short, bright, and inspirational.



Facebook is a bit more forgiving and engagement for longer videos depends on the audience, but Gary tends to make videos that are slightly longer than Instagram and always have captions for better engagement.



Youtube gives Gary the most freedom. This Close Your Eyes Till You’re 29 video is actually a compilation of other videos he released on Youtube, and he generally reserves his longer-form content for Youtube & Facebook. Notice how he always adds in a personal description to make it feel like he’s speaking directly to you.



The idea is to experiment with each platform, figure out what works best for you and your audience, and fit your content into those models.


It’s also worth noting that he repurposes image content across platforms as well, for example:

Instagram to Pinterest:



So remember this works for any type of content, not just video!

Habit #2: Gary Takes Video and Translates it to Audio Platforms

Gary excels at public speaking. In order to capitalize on that content, he almost always strips the audio from his videos and puts them out as podcasts or on Soundcloud with a brief intro.


Take his Business Squared Keynote for example:



Gary hits this keynote from all angles — the event itself, a version on Facebook in its entirety, and the same audio on all of his audio platforms. Now, that may be a bit long for Facebook audiences, but people also know what they’re getting into when someone says, “Keynote”.


That term carries prestige and immediately conveys a longer time commitment. Without that distinction, this would not do nearly as well.


Here’s that same Keynote on his podcast:



Pretty cool.

Habit #3: Gary Makes Mashups Based on Common Themes

As mentioned with the, “Close Your Eyes Until You’re 29” Youtube video, Gary and his team love to repurpose content by making new content out of old content.


Take this podcast short for example:



This release is 14 minutes and 17 seconds of GaryVee being inspirational as hell all based around a theme, “No excuses.There was nothing new shot or recorded for this segment. It’s just Gary being Gary, and these opportunities compound the more content you put out.


Then, once the mash-up is finished, he puts that material onto ALL platforms imaginable.



Again, Gary wants to be EVERYWHERE.


He wants to meet you where you’re at…

Habit #4: Gary Cross Promotes Content on Different Platforms


Some content is restricted by medium. For example, you can’t have long videos on Instagram, but that doesn’t mean you shouldn’t promote that video on Instagram.


That’s where cross-promotion comes in, and Gary does a great job of it.



Gary will embed his Youtube videos into his Pinterest account with a link going back to Youtube. This allows Pinterest users to choose their preferred platform.

Youtube to Instagram:


One thing that GaryVee does ALL the time is take stills from his popular Youtube videos and slap a caption on the image before sending it out to his social feed. With the amount of video content GaryVee puts out, this is a really common tactic of theirs.



It’s simple but really effective.

Instagram & Facebook to Youtube:

Here’s an example of Gary taking a shorter edit of his new Youtube video and using Instagram to push traffic to Youtube.



He also includes the link in his bio, and since GaryVee fans know how often he puts out content, his audience gets used to checking there for quick links to the latest videos.



Gary also uses Instagram stories to push traffic to his podcasts & Youtube videos. By including the link in the Swipe Up option, he can pull people directly to Youtube or his podcast to get them more involved.



And here’s him doing the same thing on Facebook. Notice it’s cropped appropriately & includes captions (Facebook specific habits).



If Gary has a big launch or charity he’s interested in promoting, he knows he can motivate his audience to help something go viral by running contests.


Here’s an example of him launching #FirstinLine. He uses Instagram stories to explain the rules and pushes people to his new Messenger Bot with the promise of winning prize


It’s not Gary’s Facebook or Gary’s Instagram… It’s this giant social hub of content that all connects to each other seamlessly.

Habit #6 – Retargeting for Maximum Exposure

Once you view almost any piece of GaryVee content, he’ll keep sending you more — even through ads on his own videos!


For example, I was trying to watch a GaryVee video, and I got an ad for another GaryVee video.


By taking his most popular videos and cross-advertising them on his other videos, he makes sure new viewers see him at his best (another form of establishing belief!).


Main Takeaways:

  • Fit your content into each platform’s culture. A.k.a. context.

  • Develop ways to repurpose your content in a way that’s both fresh and not super labor-intensive.

  • Direct traffic to the best platform for viewing that particular piece of content.

  • Use retargeting to bring people to your best content.


WHAT’S NEXT:Okay, online business owners and marketers, here’s how to start taking advantage of this for your brand or business right now.


  • Take a look at your mission, your passion. What makes you, you? What’s your end-game? How would you need to diversify to get there? Think top down here. Figure out what makes your business tick and envision your future. Be bold. Be brave.

  • Find your medium. Is it video? Audio? Text? How is your voice best represented and what’s the most fun/motivating type of content for your business to create? If you have no idea, try EVERYTHING and go from there. Let the data make the decision for you.

  • Once you have one piece of content you’re really proud of, think about how it should change from platform to platform, and then release it around to as many channels as possible.

  • Take a look at your own funnel and compare it to the suggestions. Where are the holes? Do you always provide a next step? Have you established the right beliefs at the beginning? Are you segmenting appropriately? Can you be more specific toward your customer avatars?

  • Establish a good lead scoring system and pair that with retargeting to always supply your leads with the appropriate next step at the right time.

  • Enjoy the process 🙂


That’s it!


I hope this helps you crush it like GaryVee.


He does even more than what I cover in this article, but this should at least get you in the mindset and give you some ideas on how GaryVee approaches marketing/how you can apply it to your own business.

And if you know GaryVee or think he should see this. Hit him up!





Until next time.

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