The follow up hustle: How I got Gary Vaynerchuk to do an interview

Last year, I interviewed the one and only Gary Vaynerchuk for our blog. To a lot of people, that was a pretty impressive feat, especially because last year we had a much smaller audience, whereas Gary had more than a million followers on Twitter and amazing Facebook page engagement.

Friends kept asking me, "How did you pull that off? How did you get Gary to dedicate an hour of his time to do an interview with you, Steli?"

Learn more about how to connect with famous or busy people by getting a free copy of The Follow-Up Formula: How to Get Everything You Want by Doing What Nobody Else Does.

How I made the interview happen

In terms of Internet fame, I was basically a zero. Until that point, most of my entrepreneurial triumphs happened under the radar, and the small amount of notoriety I had was generated by me stubbornly struggling with a startup that had been a failure many years before I realized it.

Gary, on the other hand, was getting paid tens of thousands of dollars to speak for an hour at events.

So it was a fair question to ask: how did I convince Gary Vee to do the interview?

Here’s the short answer:

Persistent follow-up hustle

As long as I think it’s worth it, I don’t give up. The first time I reached out to Gary was several years ago, even before Close or ElasticSales existed. At that time, a couple of my friends and I were trying to build the Internet’s QVC—an online shopping channel for the new generation. We were live-streaming from a studio in Los Angeles, spending many thousands of dollars on Facebook ads to buy an immediate audience, and moving tens of thousands of dollars in product.

During that period, I read Gary’s first book Crush It! (If you haven’t read it, it’s an absolute must-read even though it was published in 2009.)

At the end of the book, he listed five billion-dollar business ideas that he liked but didn’t have the time to pursue. Guess what the first idea was?


When I saw that, I got very excited: “Wow! We gotta get Gary to invest in us and get him involved in this venture!”

Our elaborate pitch

We wrote Gary a very long cold email. (Back then I knew surprisingly little about cold emailing. I should’ve gotten into a time machine and listened to this.)

We created a website on a ridiculous domain, something like, and plastered its background with the NY Jets logo (we had learned he wanted to buy the Jets one day). We also put in a couple of video snippets of our QVC live stream along with a business plan.

We invested a lot of time and energy into this pitch. Convinced that our pitch was irresistible, we sat back and waited for Gary’s enthusiastic response—surely he’d want to invest.

His response?


Nothing. No reply. We sent another email. No response. A couple more follow-up emails, tweets, and phone calls. Nothing. Either he wasn’t even aware of our efforts, or he completely ignored them.

I could have felt hurt or upset that we put in all this effort and didn’t get a reply from him or anyone on his team. I could have felt entitled to get some kind of reaction.

But I didn’t, and neither did my friend. We didn’t attach any feelings to this non-outcome. We tried our best to get Gary’s attention, and then we just moved on.

Several years later

Fast-forward to 2013. I was watching a video of Gary Vaynerchuk together with a friend, and we heard Gary say he’s a salesperson at his core.

I’ve watched a ton of videos of Gary, and nobody ever asked him about sales. Everyone wanted to hear his thoughts on social media, ecommerce, Internet businesses, and marketing, but no one ever asked him about his thoughts on how to sell.

So I got this idea of doing an interview with Gary on salesmanship.

A common acquaintance

One of our investors is a close friend of Gary’s, so I reached out to him and pitched him the idea.

At first, he gave us a polite pass: “Gary is currently on a book tour. Follow up with me me again in a couple of months, and maybe I’ll try.”

Which is exactly what I did.

Our investor asked Gary if he’d be willing to do the interview, and Gary said he liked the idea.

And then: silence.

I followed up a couple of times again.


Followed up again.

Finally, a response from Gary’s team: “Gary’s interested. He wants to do the interview.”

Yes! … or no?

Now I had my official yes: Gary had made the commitment ... Except I had to keep following up for months to finally make the interview happen. There were all kinds of scheduling conflicts, last-minute cancellations, and other obstacles in the way.

I could have thrown in the towel or gotten all indignant about this.

But I realized that Gary is just a crazy busy guy who’s overwhelmed with requests. If I wanted to get an hour of his time, I’d have to work around that.

Conducting the interview

If you watch the interview, you’ll see Gary isn’t excited at first. Clearly, he feels there are a lot of things he would rather do than an hour-long Skype interview in his hotel room with some dude nobody ever heard about—it’s written all over his face. But as the interview proceeds, you can see his energy changes and he genuinely begins to enjoy the opportunity to explore a couple of questions no one has ever asked him.

According to his wife, this was the best interview he did in years!

What the interview did for us

This video got more than 20,000 views, which might not mean much if you’re posting a 30-second video of a cute cat, but it is pretty impressive for a 43-minute talking-heads Skype video with crappy sound and video quality.

I enjoyed interviewing Gary very much, but it was our company that really benefited from it.

Here is what happened as a result of the interview:

  • A lot of trial signups for our sales software
  • Thousands of dollars in revenue
  • Some of Gary’s followers started following our brand as well
  • It elevated our brand and our credibility as a company

Your current results in life are an indicator of your past hustle

Everything that’s going on right now in our business is the result of the work we did months or even years ago.

Just consider the interview with Gary. I was able to engage him in a really interesting conversation only because I knew his stuff: I had read his books, I had watched his videos, and over 15 years I had developed a deep understanding of the sales process.

I didn’t ask him the same questions he’d already answered a hundred times—I made it interesting for him by asking him questions that prompted him think about himself in ways he might not have deliberated in the past.

Not happy with your current achievements?

If you think what you have accomplished thus far is not enough, it’s not because of what you’re doing today. It’s because of what you did and didn’t do in the months and years leading up to this very day.

And if you’re grinding and putting in hard work today, don’t expect results tomorrow! That’s not how real life works. That’s what Hollywood movies and the media can make it look like because the dream is what sells.

But in real life, your success is the result of years spent on the grind. Those overnight successes represent only 0.1% of the people who succeed, and in many cases even their overnight successes have been preceded by years of hard work.

How can you outhustle your past self?

That’s the question you should be asking yourself: what can I do today that will create bigger results six months from now than those I’m having today as a result of my efforts six months ago?

Although you want to operate with some sense of urgency, focusing only on the near future will give you a myopic perspective of your goals and achievements. Make sure you have a long-term view of your goals and enough patience to see them through.

Want to become a master of the follow up hustle? Get a free copy of my book, The Follow-Up Formula. You'll learn: how to follow up systematically, creative tactics for following up with prospects when the stakes are high, and which common mistakes to avoid when following up (and how to do it right).

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