Business Tips: Why Being Afraid to Ask Someone Out Is Bad for Business | DailyVee 500

Business Tips: Why Being Afraid to Ask Someone Out Is Bad for Business | DailyVee 500

Awesome Tip: Why Being Afraid to Ask Someone Out Is Bad for Business | DailyVee 500



There are so many people out there who were too scared to ask out the person they were most into … and missed out on the chance to marry the perfect person.

It’s how life works…you don’t ask, you don’t get.

Same thing applies in business.


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Gary Vaynerchuk is the chairman of VaynerX, a modern-day media and communications holding company and the active CEO of VaynerMedia, a full-service advertising agency servicing Fortune 100 clients across the company’s 4 locations.

In addition to VaynerMedia, VaynerX also includes Gallery Media Group, which houses women’s lifestyle brand PureWow and men’s lifestyle brand ONE37pm. In addition to running VaynerMedia, Gary also serves as a partner in the athlete representation agency VaynerSports, cannabis-focused branding and marketing agency Green Street and restaurant reservations app Resy.

Gary is a board/advisory member of Ad Council and Pencils of Promise, and is a longtime Well Member of Charity:Water.

Gary is a highly sought after public speaker, a 5-time New York Times bestselling author, as well as a prolific angel investor with early investments in companies such as Facebook, Twitter, Tumblr, Venmo, and Uber.

Gary is currently the subject of DailyVee, an online documentary series highlighting what it’s like to be a CEO and public figure in today’s digital world, as well the host of The GaryVee Audio Experience, a top 100 global podcast, and host of #AskGaryVee, a business and advice Q&A show which can be found on both YouTube and Facebook.

Gary also appeared as judge in Apple’s first original series “Planet of the Apps” alongside Gwyneth Paltrow, Jessica Alba and Will.i.am.

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33 Replies to “Business Tips: Why Being Afraid to Ask Someone Out Is Bad for Business | DailyVee 500”

  1. Gary I fucking loved that ending brother! I've only been watching you for about a month now but what you've taught me with your videos is insane. I was attacked in Laughlin about 3 months ago, and got fired from my job while in the hospital, and crashed and wrecked my truck as well. I was so bummed about all of it, but now I feel like it was the best thing ever. I invested my last pay check, before being fired, into a bunch of military items I thought I could flip. It's only been about 2 weeks but I already made 5 times my money back by selling them on eBay. If it wasn't for your videos putting that idea into my head, i'd be super depressed, wondering wtf imma do. I'm so glad that shitty job fired me when I was at my lowest, cause now im driving for more. I can't wait to see what 2019 has in store.

  2. You know when they say everything happens for a reason? It's based off moments like this. She got into that accident for a reason. She wasn't meant to work for Adidas. Did she give up? NO! She kept on trying. Did Gary say forget it and walk away towards his evening? NO! He stayed and took that one last call. Coincidence? I think not! And now she's here in the place where she would have never even sought out if she were at Adidas and she's so much better off for it. I don't believe in coincidences. I believe in design. Everything works out in the end. It just does! If it's not working out then it's not the end yet. Life's about the journey.

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