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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