Fresh out of college, I took my family wine business and grew it from a $3M to a $60M business in just five years by hosting a wine YouTube show. Now I run VaynerMedia, a 600+ digital agency, invest in companies like Facebook, Snapchat, Twitter, Tumblr, Uber, and Birchbox, and co-founded Vayner/RSE, a $25M investment fund.

I currently host The #AskGaryVee Show on YouTube, a Q&A show where I take questions via Twitter, Instagram, and Facebook about social media, entrepreneurship, startups, and family business based on my experience of building successful, multi-million dollar companies.

My latest book "#AskGaryVee: One Entrepreneur's Take on Leadership, Social Media & Self-Awareness" comes out tomorrow (3/8) and showcases the most useful, surprising, and thought-provoking questions from the YouTube show.

Book available here:

Read more about me here:


*** Thanks guys! I'm done answering questions for now, but check me out on the #AskGaryVee show!

Comments: 681 • Responses: 59  • Date: 

WhatDoesTaiLopezDO33 karma

What does Tai Lopez actually do?

askgaryvee42 karma

I am not sure. I've met him once and the truth is I don't know.

ParanoidPanda3520 karma

Have you ever considered getting into e-sports?

askgaryvee39 karma

Not only have I considered it, but I'm going to be actively doing stuff with it.

jordansideas16 karma

Hey Gary,

According to Wall Street, Facebook is currently 23 times more valuable than Twitter. Do you think this is a fair valuation, and if not, why do you think investors are erroneously thinking this way?

askgaryvee20 karma

I believe that that is a fair evaluation. I would actually put it at a higher multiple than that. I am extremely bullish on FB and think it is grossly underpriced.

*I'm a stock holder of both.

Fitnessisruined14 karma

I'm a personal trainer who is on my own journey to loose weight after an injury. I'm thinking about documenting this journey but at the same time i'm wondering "who wants to watch a fat personal trainer talk about fitness?". Any quick tips?

askgaryvee28 karma

The truth is undefeated. I think a ton of people would want to watch that journey because a ton of people are also going through that journey now.

LordStandley13 karma

Thanks for doing this Gary!

If you could choose one person to review and promote your new book, who would you choose?

Can't wait until tomorrow to get my hardcover and audio versions!

askgaryvee22 karma

That's a great question. That's a really good question...

Taylor Swift.

conrad52113 karma

You could have done anything - why an agency? Not known for setting the world on fire in terms of revenue.

askgaryvee14 karma

Because I'm stunningly patient and I knew that scaling my strength as being a marketer would pay back dividends... it would help me scale all my other passions and goals.

PB_hold_the_J12 karma


I first came across the #AskGaryVee Show through Casey Neistat's Vlog. I wasn't a fan of your aggressive style of interviewing, but after a friend of mine told me to dive deeper I found the wealth that is your knowledge. In my opinion your show is much better when you're alone and don't have a guest.


If you were dropped in the middle of a country where no one knows your name, who you are, what you do, what you're capable of, with nothing but the clothes on your back. That means no money, no phone, no internet capable devices of any kind. How would you make it back to Vaynermedia to have your Caesar salad with no dressing that trainer Mike has waiting for you?

askgaryvee14 karma

I would hitchhike. People grossly underestimate people's kindness.

badnewsbaron11 karma

Gary I'm at a mexican restaurant right now. They have margaritas. Do I get it frozen, or on the rocks? Regular, strawberry, or mango? I'm in some real serious shit, Gary. I need your advice Gary. The server is almost back. I can't tell her I need more time Gary, I just did that. Tequila is on the line here.

askgaryvee16 karma

Do they have wine?

go rocks and regular. keep it classic.

OculusNYC10 karma

Hi Gary, totally enjoyed your talk at the 92nd St Y last night! What are your top criteria for the clients you choose and the business you pursue? Thank you!

askgaryvee17 karma

If they're willing to pay... lol the truth is we react to inbound opportunities. We got the only client I ever wanted, as our first client: the New York Jets

DaRealMidnight10 karma

Hey Gary, any advice to a freshman who wants to start his own business after college?

askgaryvee34 karma

Make sure you use these next four years to learn a lot because you will never have this much downtime again. Do entrepreneurial things every day.

taylornikolai10 karma

I'm a "Snapchat Influencer." How can I best leverage my influence right now?

askgaryvee20 karma

I'm not sure but email me at gary [at] vaynermedia [dot] com with how many views your getting and I want to collab. up!

Newcicci10 karma

Hi Gary, is it me, or are you just EVERYWHERE right now? How has that come together? Was it planned? I'll be at your gig in Sydney next week, can I bring you wine?

askgaryvee12 karma

Yes bring me wine

As far as part one, not it's just luck ;)

TheSassyNinja10 karma

What do you think of reddit as a whole and for marketing?

askgaryvee8 karma

I think it's a massively important community on the internet and has substantial marketing opportunities.... my team is embarking on some reddit ads and I'll have some more insights this summer.

royalbailey10 karma

Does anyone eat bananas like you?

Colin K

askgaryvee11 karma


quietandconstant10 karma

What new verticals do you see being the most profitable in the next 3-5 years?

askgaryvee5 karma

I don't predict, I just react

Cydonium9 karma

Hey Gary! First of, huge fan here, you're a big inspiration! Keep Hustlin' My question; I'm from an eastern european country and I've recently launched a local digital marketing agency. The problem I'm facing is stubbornness of business owners here. Many businesses here don't even own a website, let alone a more serious digital presence, even though it would benefit them tremendously. How do I get these people to change their minds?


askgaryvee20 karma

By not selling to the unsellable.

Instead of focusing on people who can't be shifted, focus on the people who are flirting with it.

This is how I built vayner in 2009 we had a similar situation in the US.

venturecapital919 karma

Would you rather be able to sign mo and snacks or keep fitzpatrick?

askgaryvee9 karma

Keep fitzpatrick!

TheeSargent9 karma

What's your thoughts on Search Engine Optimization compared to Social Media?

askgaryvee13 karma

I think that I day trade attention and there's a better arbitrage on social media than SEO right now, but it depends on the business.

xiloki9 karma

Regardless of how much it would cost, what do you think it would mean for the music industry if Google acquired Spotify? Do you think it would finally mean an all-in-one product for audio and video (ie integrating with YouTube)?

askgaryvee5 karma

Ummmmm...yeah. I mean, I dunno. Fine. I'm not trying to be mean to the question, I just think it would mean a more substantial competitor to Apple but I don't think it would be THAT much.

wifiteacher8 karma

Gary Vee!!!

I am a teacher. My income is capped. Where do you see a market for teachers??

askgaryvee20 karma

For teachers to understand they're in the same place as athletes in the 50s. They need to find a way to make income in the summer through their passions and skills.

SportsBAMF8 karma

If you had to choose which platform to start on what would it be? Blogging, Podcasting, or YouTube Videos?

askgaryvee13 karma

I would reverse engineer my talents....

For me, I'm great on video, so I would start with YouTube. Know your strengths and work on the platform best for you.

linchpinfilms8 karma

Do you consider multi level marketing entrepreneurship?

askgaryvee15 karma

No. There is a difference between the companies at the top and the bottom. What makes the difference in the companies that aren't at the top is the disproportional amount of people at the bottom.

cpietr018 karma

When will you be acquiring the New York Jets?

askgaryvee11 karma

Hoping for 25 years from this moment.

Anaafi127 karma

How would you advise jabbing an executive on twitter you would like to connect with, and then bringing value to on an ongoing basis?

askgaryvee21 karma

By reading the last 100 tweets that he or she has put out to create context around what they care about / find out what they do outside of business.

gsnakedaily7 karma

What 3 skills should someone in their early 20s start developing and mastering asap?

Stated differently, what 3 skills do you believe will be the most valuable in the coming future?

askgaryvee17 karma

gratitude. empathy. self awareness.

kylelreed7 karma

So happy you are doing this and excited to get my books tomorrow.

Did you ever think about Franchising Wine Library? If yes, how would you have set it up? If no, why?

askgaryvee3 karma

I thought about it a lot. I never got far enough to figure out how I would set it up but ultimately my career took another turn with tech & investments.

Brometheus57 karma

Gary, how do you view Instagram as a marketing tool for teens?

askgaryvee3 karma


1986JamesHetfield7 karma

Hey Gary,

I'm going to be a Dad in a few months. What is one piece of advice you have?

Also... shooooooowwwwwwwwww.

askgaryvee16 karma

You're gonna be scared at first, and that's okay. My advice is to just enjoy it.

samsheffer7 karma

Gary! Was good seeing you yesterday!

My question: what's your favorite spread to put on bread?

askgaryvee12 karma

Nothing now because of my trainer Muscle Mike but historically peanut butter.

rchittner6 karma

What do you use or recommend using to track social analytics beyond what is included on that network's site?

askgaryvee11 karma

i don't use other things outside of the site's native analytics. truth is, the sites are creating more than enough useful data.

plzgivmecoke6 karma

If your blood were a wine, what year would it be, and would it get me drunk?

askgaryvee15 karma

1975 because that's the year I was born and you would get drunk on passsssssion!!!!

Wabes6 karma

What does your sleep pattern look like? When do you usually go to bed and when do you wake up? Do you have a morning routine that helps jumpstart your day?

askgaryvee8 karma

basically 12-6, core norm for sleep. jump start with the alarm then working out with mike.

SushiMakingRobot6 karma

Hey Gary! Long-time fan of everything you do. Congrats on the release of the fourth book. Can't wait to get my copy tomorrow!

Question: What's the best piece of advice you could give someone starting a new job as a social media manager at a CPG company? How can I make the biggest impact / best impression in the first week?

askgaryvee13 karma

By talking about sales and nothing else. Realize that social media is a gateway to a transaction not a fluffy thing or marketing jargon.

hollyac6 karma

What is the #1 most important thing to you when investing in a new company?

askgaryvee10 karma

A and B: (A) The jockey--the CEO and (B) I have to believe that the product is scratching an itch in the marketspace.

AlexSandalis6 karma

Hey Gary, been watching you since I was 17, 21 now. So a long time follower thank you for everything you do for us.

  1. Is there anything you would trade a year of your life for?

  2. Will you follow me on Snapchat and maybe Instagram? @alexsandalis

Bonus: My most popular piece on Medium titled 'Self Awareness' is largely result of what you taught me about the subject. It featured you and I thank you for unlocking that piece in me.

askgaryvee3 karma

  1. Nothing. UHHHH actually a Jets Super Bowl.

ihateatmfees6 karma

Have any advice for someone wanting to make and sell mobile games?

askgaryvee12 karma

first and foremost understand how difficult it is, it's outrageously competitive. Be ready to be in the top 1%

blackleaf315 karma

What is your net worth?

askgaryvee12 karma

I know there is a search result that says it's 10 million I can assure you it is much larger than that.

The truth is this: I really don't know. truly. I mean that. I really really don't know. i know it's not 10 million. wine library alone is worth more than that.

chadchud4 karma

I'm a timelapse photographer and I'm wondering how to expand my business when clients want me to shoot their projects. I can train people but they still want to book me for me! Any suggestions to stop being a one man band?

askgaryvee7 karma

By not giving the option for people to book you. You're allowing your ego to trump the upside of your business.

padix4 karma

Your best advices to succeed in selling T-Shirt on Teespring with Facebook ads?

askgaryvee8 karma

were not sure but we'll run tests and hit you back with some data.

hit us up on may 3rd for the info!

rlv094 karma

What do you think about MBAs and grad school in general?

askgaryvee11 karma

I think that if you're an entrepreneur, it's a bad ROI. If you want to be a consultant for a big firm, it's a good ROI.

Portmanteutally4 karma

You travel all the time. What are your must-have items, tips and tricks for being an expert road warrior?

askgaryvee7 karma

my phone. and my hoodie so i can cover my eyes sometimes.

rubberduckiedale3 karma

What is the worst customer service experience you have ever had?

askgaryvee8 karma

I'm not sure because I literally don't accept the negativity.

But now that I think about it, when I was 18 the westin hotel wouldn't give us a room. I got competitive and wanted to be a baller because i had the money for the penthouse. they pissed me off when i was 18.

epicPiglet3 karma

What do you think of the hypnotherapy market? for things like anxiety, good sleep, lose weight?

thanks gary, love the shoooooow

askgaryvee4 karma

I don't know much.

Molves2 karma

Love your videos! I am 39. Have a shit ton of experiencing and success advertising on Facebook. Just left my day job to start my own consulting company for promoting seminars. I am also working on 2 start ups, supplement company and small business marketing e-learning. Married with two wild boys, 4 and 2. Am I spreading myself to thin and should I drop shit and focus on one project at a time?

askgaryvee5 karma

I don't think so. I'm going on intuition here.

I think you should drop leisure, and go for it. There are moments and times in an entrepreneur's career when you have to sacrifice leisure for upside.

jwb71112 karma

Question: How do you balance persistent follow-up vs being annoying/rude? Whats your process for determining that? Thanks for all you do!

askgaryvee3 karma

Gut feeling. Everybody has a different gut feeling but your ability to use your gut feeling will be the variable for your success in that environment.

BenNieIV2 karma

How important do you think an elevator pitch is? And can we hear yours for Vayner Media? :D #FEWDM

askgaryvee6 karma

I do not think it's that important to the top investors of the world, but it is very important for second and third tier investors.

20dollerbill2 karma

Hey Gary,

Just want to know when you're going to play me one on one in basketball? I've upped my wager from 50 to 75 books.

Will travel.

askgaryvee3 karma

The truth is I'm not confident in my basketball game and I like to put myself in a position to win. Mike isn't letting me play right now. :(

omenemo2 karma

Is there any media (books, videos, etc) you would recommend for people who want to run a company that is focused on human resources and improving company culture?

askgaryvee2 karma

I will be writing about that shortly... but the truth is I don't know. I don't consume stuff like that, so I just don't know. I'm sure there are people who do.

missnorthernbelle2 karma

Hi Gary, if you were to start a few subscription box businesses, which niches would you choose?

askgaryvee2 karma

a wrestling box i love wrestling and people are into it, the only box i will pay for is wrestling actually.

call it the squared circle!!!!

rdavemacdonald1 karma

We get asked a lot about Twitch and the attention it provides. I would love to hear your thoughts on esports. Does VaynerMedia look at Twitch for clients looking to capture Millennials attention? Thanks

askgaryvee3 karma

We've not done enough digging into twitch as we should, especially given my enormous attention to esports. WHICH IS A MISTAKE.

1986JamesHetfield1 karma

Gary, what is your workout regimen these days? When the hell do you normally do your workouts?

askgaryvee2 karma

We normally do workouts at 6:15am weekdays and later on weekends. 1 hour workouts. 3 days of upper body, 1 day of lower, 1 day yoga, 2 days of cardio.

totterman1231 karma

Who are the 2 people (not including your parents) you learned most from by watching?

askgaryvee3 karma

I only really learned from one person: the market.

The_Paul_Alves1 karma

Hey Gary, What wine are you drinking RIGHT NOW?

askgaryvee3 karma

None, because Mike has me on a real fucking shred.

iamnitro1 karma

Who do you want the Jets to keep or sign as a Free Agent?

askgaryvee2 karma

Keep everybody, but I know that's not proper. I think Snacks is the guy who's gonna walk. But awfully scared of Fitz walking....

LordStandley1 karma

Gary, why no audio book for JJJRH?

askgaryvee3 karma

I felt it was too much of a textbook. I also really struggle with reading and didn't want to go into the booth.... left a lot of money on the table.

StriveForExcellent1 karma

Gary, you talked on Lewis's podcast about being very self-aware of your strengths. Do you have any advice/resources someone could use to help them discover their biggest strengths?

Dexosaurus1 karma

Coming to see you next week in Sydney, excited!

You got asked a question in the last #AskGaryVee that I had a slightly different spin on: You grew Vayner Media really quickly - did you do this through acquiring smaller agencies and their clients, or was it completely through recruitment and sales?

askgaryvee2 karma

Completely thought sales and recruitment, except with the LA office.