Answering 105 Questions From Fans


#1 — 2:26 

“How does a retailer deal with the internet squeezing the middle man?”

#2 — 8:49

“How do I qualify to be interviewed by you in the next two years?” 

#3 — 10:13

“As a young rapper, how do I maintain growth?” 

#4 — 12:04

“I’m in law school, and want to start my own business and be the next Sarah Blakely, but should I work for someone to learn and get experience or start at a larger company?”

#5 — 16:53

“How do we educate people so we can grow as fast as we can?’

#6 — 25:46

“What would you think about offering people wine tastings at the doctor’s office?”

#7  — 30:14

“My brother and I starting to flp making almost $3,000 a week, we met you before.”

[I like this one because Gary shows off his memory]

#8 — 34:48

“I came out from Brooklyn to tell you … You’re gonna go down as one of the greatest”

#9 — 35:56

“What’s the best way to share a clear, concise message to parents?”

#10 — 37:56

“I’m a school teacher any words of advice for the kids?”

#11 — 43:53

“What did you learn from social media this week?”

#12  — 45:15

“I have a huge fear of time — how different life is gonna be in 20 years.”

#13 — 46:54

“We just started marketing, but we also want to make time for the people we love.”

#14 — 49:12

“I started my own eBay business and last 60 days make $540.”

#15 — 50:38 

“I”m a senior in high school I battled depression as a sophomore and junior and now I’m a late entry for the Marines — I’ve created an organization to help people with the same struggles.”

#16 — 52:42

“WIll you sign my shoe?”

#17 — 53:00 

“I’m self conscious about my teeth — should I make it part of my story?”

#18 –56:39

“What advice do you have for a 28-year-old immigrant?”

#19 — 58:40

“How important is to convey to potential employers my independence?”

 #20 — 1:00:28

“We’re trying to create a plan of attack with cryo-therapy. It’s died down a lot. What would your plan of attack be?”

#21 — 101:40

“I’m big into TikTok influencer marketing … I’m not really worried about it dying down because when it does die down I’ll just move on to the next thing.”

#22 — 103:26

“What’s the key to staying consistent in whatever you’re doing?” .

#23 — 1:05:28

“For entrepreneurship is there a model you can follow like working out?

#24 — 1:06:37

“From the bottom of my heart, you unlocked everything I need for the rest of my life.”

#25 — 1:08:01

“I run an encryption company … any advice for me on how to get marketshare?” 

#26 — 1:09:24

“We have a collective of artists, how do we market all of us together?”

#27 — 1:10:19

“I own a mobile car detailing business, what’s the next step?”

#28 — 1:12:58

“I started a construction business — how do you know who to talk to at these big companies?”

#29 — 1:14:15

“I’m a former drill instructor in the military and law enforcement and I have a gift for you made from pennies.”

#30 — 1:15:50

“I need a bold red wine that represents my grandmother.“

#31 — 1:17:06

“I wrote book about 401K investing ..  can you give advice to people about the importance of saving?”

#32 — 1:17:56

“I’m a college professor, I didn’t know who you were until two months ago until my students said he’s so Jersey, he’s Gary Vaynerchuk.”

#33 — 119:13

“When I’m juggling a lot of things, how do I deal with it when I drop something?”

#34 — 1:24:39

How do I find good mentorship?

#35 — 1:25:56

“I always asked, why you never text me back – and then you texted me back.”

#36 — 126:17

“I’m a massage therapist and I left my job to start my own business and now I’m pregnant.”

#37 — 127:12

“I’m in the home construction business, how do we grow an audience that follows our business.”


“What do you think is the #1 quality in a woman?”

#39 — 129:22

“How often do you adjust your ending?”

#40 — 130:03

“I chose not to go to college, but what if that impacts my ability to find love/life partner?”

#41 — 131:09

“I’m a musician who just got signed by a label, how do I get to millions of people?”

#42 “But I don’t use TikTok”

#43 — 1:32:27

“I want to start a business so I can go into the music game with [something], I want to open up a smoothie shop.”

#44 — 1:36:00

“I think gratitude is everything, can you give me a message for Shawn?”

#45 — 1:37:29

“I started flipping over the summer I made $15K.”

#46 — 1:40:18

“How do I build a subscription model on Linkedin?”

#47 — 1:42:15

“I had a near-death experience getting hit on my bike training for an Ironman.”

#48 — 1:45:50

“How do I find the right partner and capital to grow my business?”

#49 — 1:47:17

“I’m in real estate, but people get so mad when I ask them for business — is there any other marketing options?”

#50 — 1:49:06

“How do I find my drive again?”

#51 — 1:50:36

“I have my hands in two things — my parents coffee shop and a transportation business. Where do I put my energy?”

#52 — 1:52:19

“If you’re looking to start a business at a young age, what are some strategies you would use to get people’s attention to buy my thing?”

#53 — 1:54:57

“You have advice for me building up my company to get more customers?

#54 — 1:55:15

“When can I have you on the podcast?

#55 — 1:55:55

“I have an illustration company that’s blowing up, but as for the operations, I’m fucking lost.”

#56 — 1:57:03

“I’m doing custom apparel — we started podcast will you be on episode #5?”

#57 — 1:58:49

“How often should we update our LInkedin?”

#58 — 2:01:15

“I”m creating a flip book — how can I get you to look at it.”

#59 — 2:02:54

“You changed my life, I was homeless for two years … Crushing it was one of the first books I read … it hit the switch man.”

#60 —  2:03:59

“Is it wrong of me to be selfish and change my mind?”

#61 — 2:05:48

“How do I get more exposure?”

#62 2:07:40

“You’re such an inspiration, found out an hour ago they’re about to foreclose on my house but I still made it here.”

#63 2:09:18

“I’m trying to brand myself what can I do?”



#64 — 2:15:31

“As a kid, on eBay what should I invest in?”

#65 — 2:22:54

“I’m awesome at the wine, but not the marketing.”

#66 — 2:23:57

“I want to do music videos, but want to go to college to make the connections.”

#67 — 2:26:10

“What’s your favorite color, number and cartoon?”

#68 — 2:26:44

“What advice do you have for me if I get frustrated?”

#69 — 2:29:49

“I’m 17 years old and you changed my fucking life … what about Shopify. What would be your shopify strategy?”

#70– 2:32:26

“We’re juniors now, I don’t really know what I want to do”

#71 — 2:37:30

“I listen to you on repeat, because I’ve really got to put it into action and trust the process.”

#72 — 2:39:29

“Can you deliver a message to young entrepreneurs in South America, Ecuador, Latin America?” 

#73 — 2:41:15

“How do we market in Ecuador?”

#74 — 2:42:55

“Was working in construction with my father and quit 2 years ago — I did business with China and got finessed and now trade bitcoin. I hate to work construction but my dad’s sick. Should I stop trading and do construction to help my family?”

#75 — 2:53:16

What advice do you have for Millennials starting from zero?

#76 — 2:55:44

“What advice do you have for idealists in school?”

#77 — 2:56:17

“I’m shaking a little bit, I’m an artist and I got a TikTok two days ago. I sell copiers and it take hour and half to get to work” 

#78 — 3:01:07

“My job is in marketing it ends in January, I’m 26 and I feel lost.”

#79 — 3:01:58

“You’ve inspired my sons to be entrepreneurs and one is not going to college — what advice do you have for Georgie. They wake up with hope and faith because of you.”

#80 — 3:03:34

“I’m selling coffee, what’s a pointer you have?”

#81 — 3:04:25

“We sold $10M last three years, selling sports apparel business and how do I get to $100M?”

#82 —  3:11:18

“I had some bad business experience with my family, what should I do now?”

#83 — 3:14:13

“Starting my own pressure washer business. How do I do it?”

#84 — 3:16:17

“My parents support but razz me about my business. My dad doesn’t believe in me.”

#85 — 3:18:34

“Trying to make it about happiness over success — how do you get there? My mom wants me to be a doctor or a lawyer.”

#86 — 3:21:24

“Can you shoot a shout out to roommate Matt?”

#87 — 3:22:15

“I think I look like you … want some advice”

// creating content is the actual answer …. The question is why you don’t post”

#88 — 3:25:42

“I’m a high school junior in Springfield, NJ and  I’m not entirely enthusiastic about school. I’m passionate about creating. Would you be willing to let me shadow you for a day?”

#89 — 3:28:36

“I started my own coaching services, what advice do you have?”

#90 — 3:30:37

“Graduated two years ago, but I still can’t find a job. I see myself in the future and I just can’t figure out what it is?”

#91 — 3:35:08

“I wanted to thank you specifically about self-awareness. I come from a broken family, and a lot of people we don’t know how to step into business.”

#92 — 3:40:20

“You’re one of the five people I listen to … You’ve lit the fire under my ass to get it moving.”

#93 — 3:40:58

“Why do you do show the 5?”

#94 — 3:43:00

“I want to start a business of connecting people … but I need a future pep talk”

#95 — 3:47:16

“My first garage sale a bought at mahjong game from 1974 for $1 sold it for $250?”

#96 — 3:52:47

“When it comes to music making, why is completionism is better than perfectionism?”

#97 — 3:56:11

“I have a company that’s gonna drop some clothes, we open in two days  starting, do you have words of advice?”

#98 — 3:57:30

“What’s your opinion on what’s happening with Isreaeli wines?” 

#99 — 3:59:34

“I wanted your opinion on music and high-end audio?”

#100 — 4:01:39

“What advice do you have for generating leads”

#101 — 4:02:52

“In a finance 9-5 job, but you’ve inspired me to do improv, standup comedy and playing an instrument — I’m starting my own podcast and creating my personal brand is a struggle and I’m worried about hate.”


#102 — 4:04:50

“Would you GM the Jets?”

#103 4:09:39

“I’m listening and I am executing and it’s making such a fucking difference.”

#104 — 4:11:03

“What advice do you have for Immigrants who struggle with saying I love you to your kids.”

#105 — 4:13:58

“What motivates you to motivate other people?”








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