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Essay

GaryVee and Me

My Five Year Journey to Landing My Dream Guest

By Jacob KellyApril 16, 2023Also on Substack

From Day 1 GaryVee was my dream podcast guest. On Day 1632, I released my interview with him. This is that story.

Wanna go to New York?

I became a Gary fan after watching 'The Ultimate Advice For Every 20 Year Old’. It led me to his podcast which a year later led to me starting my own, My Social Life.

My first interview was with my good friend Hayden Cashion and I released it on July 30th, 2018. At the time, I wanted all of the episodes to be done in person which meant I was only recording with people who lived in the same city as me. That was about to change.

When I was four episodes in, Andy Krainak, Gary’s Brand Director, tweeted out an Ask Me Anything – I saw an opportunity. I told him once I passed 15 episodes I was going to take a trip to New York to record interviews and asked if he’d be willing to come on the show. I had no such goal and had no plans of being in New York… until Andy said yes.

On February 3rd, Hayden and I touched down in New York for six days of interviews. We’d spent the weeks leading up to the trip reaching out to people we thought would make great guests – including Gary. By the time we landed we only had two yeses and a few maybes. We were optimistic for the week ahead but didn’t know what to expect. We ended up recording ten podcasts.

While we never did end up booking Gary or Andy, we did land interviews with two Vayner employees — Caleb Ralston, who was a videographer on Team Gary and Brandon Hatcher, a videographer for VaynerTalent. Both guys asked if we’d be willing to do the interviews at Vayner and I was stunned. I can still remember sitting in Think Coffee across the street from the office, trying to keep my nerves down while waiting for Caleb to message us.

I went on to interview a handful of past and present Vayner employees throughout my four years running the podcast:

From my very first “Vayner Interview” with Caleb I was cognizant of the fact that the conversation was not about Gary. He would naturally come up as he was a part of Caleb’s story, but that’s what the podcast was about – Caleb’s story. Whenever I did a podcast with anyone from Vayner, I made sure they were my focus. I didn’t want anyone to feel like I interviewed them to try and get to Gary. I asked them for nothing but their time, not help, not an intro, not a recommendation – nothing.

I know this made a difference because Caleb thanked us for interviewing him. We should have been the ones (and we were) saying thank you but because the interview was about him, it made a difference. I’ll never forget turning around and seeing him hold his hands together like a prayer as he said thank you. I have chills writing about it all these years later.

A couple days after Caleb, we were back for the interview with Brandon. He had no hard stop and was down to hangout all night, which he did. We showed up around 6:00pm and Brandon gave us a 45 minute tour of VaynerMedia. This was the first time we got a glimpse of Gary's office – he was traveling that day but just seeing it in person was surreal. The podcast was almost two hours long and it was deep. After, we had an even deeper chat for another 90 minutes. I can remember at one point Brandon said he wished Gary hadn’t been traveling that day because he really wanted him to meet us. So close!

By the time we left the boardroom, it was after 10:00pm and the office was deserted. On our way out Brandon looked over at Gary’s empty office and asked if we wanted to go in. He rested his palm on the handle and wondered if it’d be locked or not. Then he twisted it and the door popped open. We were in. Hayden and I were flying home the next day but could have skipped our flight – the high of getting into Gary’s office would have carried us home.

Leaving New York, I knew it was only a matter of when, not if I would have Gary on the podcast. With that in mind, I started a note in my phone to prepare for the interview. From that point forward, everytime he said something I’d never heard him say before I would add it to the note. That way, when the opportunity presented itself I’d be locked and loaded with questions nobody had ever asked him. I didn’t know it at the time, but I’d spend the next four years prepping.

Do you have a VeeFriend?

I didn’t buy VeeFriends Series 1, but you know who did? Hayden. He actually got two, and they each came with a ticket to VeeCon. He called me up and asked if I’d want to go with him – it would bring us full circle. He came with me to New York and we got into Gary’s office, and now I’d go with him to Minneapolis for his conference.

I brought all of my podcast gear with me to Minnesota so I could record episodes while we were there. I’d lined up seven interviews in advance (not a single one ended up happening) so on the first day I went around the venue looking for a quiet enough place to record. After going around the stadium a few times I decided to catch up with Hayden, who I thought was at “The Dirt Stage”, because Gary was going to be speaking there.

The Dirt Stage was a side stage located underneath the stands and when I walked in, it was packed. Everybody wanted to see Gary. There was floor seating and balcony seating and I thought my best bet would be to head upstairs to see if I could try and spot Hayden from above. When I got up there, I noticed a small lineup people going out into the stadium. Curious about what they were lining up for, I peaked my head out the next tunnel and saw they were taking pictures with Gary who was hanging out before going on stage. The meet and greet lines at VeeCon tended to be around 3-4 hours long, this had less than 10 people in it. I started taking pictures of Gary from off to the side because I didn’t think I’d ever get this close again and then it clicked, THERE WERE LESS THAN 10 PEOPLE IN LINE.

I joined the queue and knew I had an opportunity to make an impression. I pulled out my phone and started frantically going through the list of questions I’d been compiling. I settled on one and crossed my fingers that they wouldn't cut the line off before it was my turn. I was the second last person they let through. I handed off my phone for the picture and asked Gary if I could ask him a question. I did this intentionally knowing that this would set the bar low, because he’d likely think I was going to ask something basic like “how do I grow my TikTok?”, I asked him this instead:

“When you buy the Jets, is Grub Ball going to be a part of practice?”

Grub Ball was a football variant game that Gary invented in high school because he wasn’t on the actual team. As legend has it, Grub Ball became so popular at his school that kids were quitting football so they could play Grub Ball instead. The fact that I knew about it caught him so off guard he broke eye contact with the camera and looked at me.

“How do you know about Grub Ball? That’s a deep cut.” 

This was my opportunity.

“I’m a podcast host known for my research. For the last couple of years, every time you’ve said something I’ve never heard you say before I’ve written it down. Can we do a five minute interview?”

He told me to email him with Grub Ball in the subject line and we’d find the time. I pretty much blacked out at this point and staggered off to try and process what had just happened. I pulled out my phone and filmed a video right away to document it while it was fresh, but I remember DRock was standing off to the side recording for DailyVee as well. This means that there should be footage of me asking Gary my question somewhere on a hard drive at VaynerMedia. I would love to see that one day.

After finding all of my friends and telling them how I met Gary, I gathered myself and sent off an email to his team.

After months of back and forth with Gary’s team, we settled on a date – Wednesday, November 9th at 5:00pm. 

I don’t need to do any more prep, right?

Over the years, my list of questions stretched to four pages. When it came time for the interview, I figured I’d only need to organize what I had into a structure that would provide the most natural flow but I wouldn’t need to do any more prep. Then the Sunday before the podcast I convinced myself a little extra research wouldn’t hurt. I spent two days pulling lesser known Gary facts from the depths of Google and 48 hours later my four pages had tripled to 12. I went through and cut everything that I didn’t think was good enough, but still ended up with 10 pages of questions for a 15 minute interview.

You’re probably thinking that that’s overkill and you’re right. I wouldn’t even need a single page to fill a 15 minute interview but I’ve always over indexed on research since starting My Social Life. I would spend hours upon hours prepping for every single episode. It started from a place of insecurity and being worried about running out of things to talk about and morphed into a way to set myself apart. I wanted to have information nobody else had and ask questions nobody would even know to ask. 

That’s the reason I had 10 pages. I wanted to have EVERYTHING and then decide what the best possible questions were from the hundreds that I had. I knew that that would give me a pretty good chance of making an impression. On November 9th, I was ready. I knew that I was going to crush the interview, I was going to rise to the occasion and make the most of my opportunity. Then I got this email: 

My moment would have to wait. But by this point I’d spent years waiting, a couple more months wasn’t gonna hurt.

“Have you done a lot of 15 minute interviews?”

We rescheduled for January 11th and that just meant that the time between my last interview and the most important interview of my life would be longer. Since the end of September I’d only done two podcasts and I was worried I’d be rusty. Right before the holiday break, I was on a call with Danny Miranda and he asked me if I’d done a lot of 15 minute interviews. I hadn’t. He recommended that I schedule some to practice because it would go by faster than I thought.

The only 15 minute interview I’d done was episode 40 with John Lee Dumas, host of Entrepreneurs on Fire, one of the most successful podcasts of all time. It was a big get for me so early on in my journey, this was a guy operating at the top of the game so I wanted to do well. As soon as we started recording the call dropped. I was living in a bad apartment at the time with even worse wifi so I assumed it was my fault. I restarted my router and sat in the call for about four minutes until John popped back in. His wifi had gone down, not mine. He told me we could do a 10 minute interview or we could reschedule six months later. After some quick deliberation I opted to go ahead and I completely botched it. 

John told me in no exact words that the interview wasn’t great because I didn’t bring anything new to the table, I hadn’t asked him anything he hadn’t gotten before. My takeaway at the time wasn’t how to do a 15 minute interview better, it was to never do a 15 minute interview again. And I didn’t… until Gary.

I never did end up scheduling those practice podcasts but on January 11th I wished I had. I knew exactly how I wanted to start the interview and what the first question was going to be but beyond that I had no plan. I was worried the rust was going to show and that I wouldn’t make the most of it.

Was I nervous? Honestly, not for most of the day. I was anxious. This interview had been hanging over me for so long that I just kind of wanted to get it over with at that point. As the day went on I slowly got more and more nervous, but I also got more and more excited. I eventually hit an emotional peak I’ve never really experienced before where my heart was beating so hard it felt like my whole body was pulsing. After the interview, my partner Halle told me she could hear me doing breathing exercises to try and calm down before the podcast. They didn’t work.

At 4:00pm Lara from Gary’s team jumped into the call and told me that his meeting was running long so he’d be a couple minutes late. Just like with John Lee Dumas, my 15 minute interview was going to be even shorter than expected.

You ready?

A couple minutes later Gary’s face blinked into the call. After years of waiting, my dream guest was sitting across from me. We exchanged quick hellos and then I got straight into the intro. Normally, I wouldn’t advise wasting time with a live recorded intro when you only have 12 minutes, but I weaved in a deep cut that I knew would set us off on the right foot. 

“Today on the podcast we are joined by Gary Vaynerchuk, some of you know him as GaryVee, some of you might know him as GNuts…”

GNuts was his username when he created an account online for the first time. I didn’t explain that on the podcast, I just did it because I thought Gary would get a kick out of it — which he did. He laughed at the mention of his old username and we were off.

By the time I’d finished the intro I fell into my usual flow. I no longer felt nervous, at least in my mind. The aggressive pounding in my chest was present throughout the entire interview. It was like the emotional high was so great that the physical comedown took longer than the mental one.

“I want you to describe to me what nostalgia feels like to you but I want to know about it in a very specific context. I don’t know when the last time you did this was, but I know every few years you used to drive past your childhood home and just kind of soak in the nostalgia. So when you’re staring out the car window at 53 Teaberry Drive – I believe it was in a triplex, the one on the left – what’s that feeling, when you’re looking at your childhood home?” 

I opened the podcast with a question about nostalgia because it checked multiple boxes. I know Gary is a very nostalgic person so I wanted to unpack what that felt like for him. I had also decided to focus the interview on old stories so I wanted to set the scene for the listener as to why I made that decision. Plus, it allowed me to incorporate a few deep cuts. Not many people know Gary’s childhood home address or the fact he used to revisit it every couple of years.

“I’ve heard you say that ‘82 to ‘88-‘89 is some of the fondest years of your life so I kind of want to stick in that pocket for this interview. I know you used to set up signs down Oaktree Road and Tingley Lane for the lemonade stand. I know you used to specifically set them at a certain height so the drivers would see them. I’m curious what was actually on those signs that attracted the drivers.” 

I don’t exactly remember why I went with this question next. It was a risky move because Gary has talked about his lemonade stands extensively. His placement of the signs is common knowledge so I made sure to call that out in the question so he didn’t rehash old material in his answer. I wasn't sure if he’d ever talked about what he actually wrote on signs though so I took the risk and it paid off.

“I haven’t answered anything about that… ever in my life. So that’s a great job by you Jacob trying to bring out some different stuff.

When answering this question, Gary reflected that a theme throughout his life was that he would watch what others did and learn from their mistakes, even as a kid. This anecdote was a gift for me because it provided me with a narrative for the interview. I now had something to reference and fall back on throughout the conversation to make it feel like there was a consistent arc and not just a bunch of random questions.

“I know you got into baseball cards at John Adams Middle School, right? In the baseball card club?”

This was my worst question of the whole interview. I asked it because I wanted the validation of having known where he got into baseball cards. Gary still gave a solid answer – he can do that with pretty much any question, but time was such a limited resource that if I’d coupled this question with the next one I could have saved time and asked another, better one later.

“When you’re at your first baseball card show at the JCC on Oaktree Road, how do you set your table up there versus how would you set up your table up now?”

How he sets up his table at baseball card shows was one of the first 15 questions I ever wrote down. I later added in the contrast between his current and past setups because I thought it was a fun angle. At first, I didn’t think it was going anywhere because he didn’t seem to remember much but then something clicked in his mind and he started remembering.

“This is a fun interview, thank you for being so prepared.”

That moment was why I spent years preparing for this interview. Obviously it’s great to get recognition from someone I admire, but to see a question I asked unlocking a memory in real time is one of the coolest feelings you can have as a host.

“You learned a lot from the lemonade stands, you learned a lot from the baseball card shows – I’m curious what you learned from the pig farm. Because if I’m not mistaken your Dad bought a pig farm when you were in the eighth grade and you were shovelling pig shit your eighth grade summer.”

In the moment, and even after the interview I felt like I could have asked a better question here. But I watch all my interviews back the same way an athlete watches game tape and in doing that I realized this was the perfect question to ask. The segue called back to what we’d been talking about, it was still in chronological order with the rest of the questions, and it provided a moment of levity before getting into deeper topics. 

“Can you tell me about your family trip to Disney World that you took with your mom and your sister?

I thought this would be a good question to start winding the interview down with. I know how much his mom and sister mean to him so I left it pretty open for him to take in whatever way was most meaningful. It worked because when he starts talking about the trip a smile keeps fighting its way onto his face and there’s a twinkle in his eye. He wasn’t talking to me, he was reliving those memories. 

“How do you think about creating those moments for your kids? In a world where they can probably have everything, meet anyone, have any experience they want.

Knowing this was going to be my last question, I had to make a decision. Do I go for another deep cut? If so, which one? Would a natural follow up be better? If so, what’s the follow up?

I went with my gut and asked a proper follow up. What I mean by that is I didn’t have the question written down, it came to me in the moment. I thought it made the most sense given where we were in the interview. I know Gary thinks deeply about parenting, it related to the previous question, and it built off the good energy we had instead of hitting a random left turn to try and squeeze in one more question that I thought might impress him.

It worked as well as I could have hoped for. The twinkle in his eye returned when he told me that he looks back on his childhood fondly, not because of the struggle but because of the love he received in spite of it. Therefore, he doesn’t need to try and recreate the struggle for his own kids, he just needs to recreate the love. To me, this was a profound note to end on.

So, how does it feel?

If I’m being completely honest, I wasn’t exactly happy with how the interview had gone. I wasn’t unhappy either but I felt like I’d left a lot on the table. Even though I only had 10 minutes, I still thought I’d find a way to extract 60 minutes worth of value, and deep down I hoped that if I impressed him enough I would get more time. When I didn’t, I felt like I’d held my strongest hand back, that my decision to go for a cohesive narrative got in the way of me asking some of my better questions. I didn’t think I’d made the most of my opportunity.

My feelings towards the interview have since changed. When I listen to it now, I feel proud. In 10 minutes I was able to get some good reactions out of Gary, ask questions nobody had ever asked him before, and establish a cohesive narrative and a satisfying arc. If you ask me, I made the most of my opportunity.

What do you mean it’s the end?

When I think about the journey, it’s filled with juxtapositions.

I simultaneously believed that my interview with Gary was going to happen but also that it was an unattainable dream. I told myself that one day I'd get the chance but I didn’t actually think it was possible. I didn’t believe in it at all but I also believed in it more than anything.

It simultaneously took thousands upon thousands of hours of work to get there but it also took 30 seconds and a bit of luck. Those thousands of hours is what allowed me to take advantage of my lucky break. 

I was simultaneously more prepared than I’d ever been, but also more nervous than I’d ever felt. I always researched more than I needed to so I wasn’t worried about running out of questions but preparation doesn't prepare you for what the moment will actually feel like. 

The interview itself was simultaneously everything to me, but also nothing. I had talked about this goal for almost five years, I’d been preparing for four, everyone knew this was a big deal for me, but now that I’ve achieved it, the moment’s passed. I’m on to the next goal.

Now that I’ve done the interview it simultaneously marks the end but also the beginning. “10 Minutes with GaryVee” is the final episode of My Social Life, but it’s also the beginning of my next chapter.

Where’s the journey heading? At some point, right back to Gary Vaynerchuk. This is not the last time I’m going to interview him, I can promise you that. I still have over nine pages of deep cut questions, so whenever he gives me another opportunity, I’m ready to make the most of it.

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