In 2019, I did a meetup at Wine Library because I’m always trying to help out pops and because I love going back to my old “stomping grounds.” During that ~4.5 hour session, I had hundreds of people show up and ask me questions – this is the mega blog post of the questions and answers!

Here’s the full video for reference:

Below, you’ll find 100+ questions that I was asked plus timestamps of where you can find my answer in the video. Hope you enjoy, and hope it brings you value!

#1 — 2:26 

“How do I deal with the internet squeezing the middle man?”

#2 – 7:57 

“How do I find out what I want to do?”

#3 – 9:37 

“Should I change my career path?”

#4 — 11:25

“People get so mad when I ask them for business — how should I sell?”

#5 — 13:20

“How do I find my drive again?”

#6 — 14:53

“My time is split between building two businesses for my parents – how do I handle it?”

#7 — 16:28 

“How do I take my business from $10 million revenue to $100 million and sell it?”

#8 —  21:13

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

#9 — 22:52

“Graduated two years ago, but I still can’t find a job I like. What should I do?”

#10 — 25:40

“How do I avoid oversaturating my feed with content?”

#11 — 27:23

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

#12 — 28:43

“How do I maintain my growth?” 

#13 — 30:27

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

#14 — 40:07

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

#15  — 44:06

“My brother and I started to flip, we’re making almost $3,000 a week.”

#16 — 48:58

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

#17 — 50:29

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

#18 — 58:20

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

#19  — 59:44

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

#20 — 1:01:23

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

#21 — 1:03:38

“I started my own eBay business and in the last 60 days made $540.”

#22 — 1:05:13 

“I’ve created an organization to help people with the same struggles, just wanted to share that”

#23 — 1:07:06

“WIll you sign my shoe?”

#24 — 1:07:44 

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

#25 —1:10:47

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

#26 — 1:13:17

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

 #27  — 1:14:50

“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?”

#28 — 1:16:04

“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.”

#29 — 1:18:00

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

#30 — 1:19:50

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

#31 — 1:21:01

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

#32 — 1:22:37

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

#33 — 1:23:46

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

#34 — 1:24:50

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

#35 — 1:27:32

“How do you know who to talk to at these big companies to get clients?”

#36 — 1:28:47

“I have a gift for you made from pennies.”

#37  — 1:30:14

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

#38 — 1:31:30

“Can you give advice to people about the importance of saving?”

#39 — 1:32:25

“My students told me that I’m so Jersey, I’m similar to Gary Vaynerchuk.”

#40 — 1:33:46

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

#41 — 1:39:09

How do I find good mentorship?

#42 — 1:40:30 

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

#43 — 1:40:50

“I left my job to start my own business and now I’m pregnant – how should I handle it?”

#44 — 1:41:44

“How do we grow an audience that follows our business?”

#45 – 1:43:18

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

#46 — 1:44:03

“How often do you adjust your end game?”

#47 — 1:44:35

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

#48 — 1:45:59

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

#49 — 1:46:44

“But I don’t use TikTok!”

#50 — 1:47:21

“I want to open up a smoothie shop, but I’m in the same spot as I was 4 months ago.”

#51 — 1:50:43

“Can you give some words of advice to my brother?”

#52 — 1:51:35

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

#53 —  1:55:22

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

#54 — 1:56:37

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

#55 — 2:00:22

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

#56 — 2:01:50

“As a young entrepreneur, how do I market my products?”

#57 — 2:04:11

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

#58 — 2:04:48

“When can I have you on the podcast?

#59 — 2:05:30

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

#60 — 2:06:30

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

#61 — 2:08:14

“How often should we update our LInkedin?”

#62 — 2:10:52

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

#63 — 2:12:44 

“You changed my life, I was homeless for two years.”

#64 — 2:13:49

“How do I get more exposure?”

#65  2:15:25

“I’m still here with a smile on my face after all that’s happened to me.”

#66  2:17:05

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

#67 — 2:15:31

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

#68 — 2:22:54

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

#69 — 2:23:57

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

#70 — 2:26:44

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

#71 — 2:29:49

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

#72 —  2:32:26

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

#73 — 2:37:30

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

#74 — 2:39:29

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

#75 — 2:41:15

“How do we market in Ecuador?”

#76 — 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?”

#77 — 2:53:16

“What advice do you have for millennials starting from zero?”

#78 — 2:55:44

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

#79 — 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” 

#80 — 3:01:07

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

#81 — 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.”

#82 — 16:29

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

#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”

#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 — 3:35:08

“I come from a broken family, and a lot of people we don’t know how to step into business.”

#91 — 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.”

#92 — 3:40:58

“Why do you do show the 5?”

#93 — 3:43:00

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

#94 — 3:47:16

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

#95 — 3:52:47

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

#96 — 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?”

#97 — 3:57:30

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

#98 — 3:59:34

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

#99 — 4:01:39

“What advice do you have for generating leads”

#100 — 4:02:52

“I’m starting my own podcast but I’m worried about hate.”

#101 — 4:04:50

“Would you GM the Jets?”

#102 4:09:39

“I’m listening and I am executing …”

#103 — 4:11:03

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

#104 — 4:13:58

“What motivates you to motivate other people?”

Watch the full mega vlog here:

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