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کتاب: از گریوی بپرس / فصل 18

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CHAPTER 16

INVESTING

IN THIS CHAPTER I’LL TALK ABOUT WHAT TO LOOK FOR IN A HORSE, WHAT TO LOOK FOR IN A JOCKEY, AND MY BEST HACK FOR FINDING THE NEXT HOT INVESTMENT POSSIBILITY.

Aside from queries looking for beginner entrepreneurial advice, I probably get more emails asking me to consider investing in start-ups than any other. I have a lot of evolving feelings about being an investor. By now I’ve probably looked at tens of thousands of deals, and yet it’s still a pretty new role for me. My investing career didn’t follow the most traditional path. Most successful investors probably start small, take a few missteps, and have some success here and there before finally getting into a position to hit the mother lode. I kind of did things backward.

What happened was I started recognizing that I had been right about a lot of things like email marketing, e-commerce, banner advertising, and Google AdWords. And then one day I read that YouTube, the video-sharing platform I had long been saying was going to be huge, had sold to Google for $2 billion. It occurred to me that maybe all this “right” could probably make me a lot more money than just selling a few extra bottles of Cabernet. So I promised myself that whatever I spotted as the next big thing—it could have been a chewing gum as easily as a new digital platform—I’d try to get involved with it. That thing was Twitter.

Twitter caught my attention in 2006–2007. While everyone else was debating the value of a platform that lets you tell the world you were eating pizza, I recognized it as a communication platform that would change the world. I became bullish on Twitter and consequently became friendly with early employees. Eventually an opportunity came in the form of one who decided to sell off his stock (talk about emotion causing you to make a bad decision) and after spending some time talking him out of selling all of it, I was able to buy some Twitter stock at an outrageously low valuation.

Once that happened I stepped back and took note of Tumblr. I thought it looked interesting, and when a high school student (who is now a VaynerMedia employee) named Louis Geneux told me that everyone he knew was on Tumblr, I knew it had gone mainstream. Eventually I became friends with Tumblr founder David Karp and former president John Maloney. They were looking for marketing ideas and by 2008 I had established myself as a personality in that space. That gave me the opportunity to invest in its “D” round at a ridiculously low level that turned around substantially for me when Yahoo bought Tumblr for a billion dollars.

During that same period, maybe even within a month, my two-year relationship with several Facebook employees put me in a position to invest at very low valuations there when a member of the Facebook family decided to sell shares.

So within an incredibly short amount of time I made three investments that turned out to be enormously profitable events for me. I started off so hot, maybe it was inevitable that when I finally stumbled it would be a face-plant of epic proportions. Get this: I was actually in the room with Travis Kalanick and Garrett Camp when the idea for Uber started taking shape.

And still I passed on the angel round.

Twice.

If I had gone in it would have probably changed my life immensely. It sure would have gotten me a lot closer to buying the New York Jets. I like to refer to this event as my “one almond moment,” after the AskGaryVee episode where I promised Vayner Nation that if anyone could guess the number of almonds filling a big glass jar next to me on the table, I’d pay their way to New York and they could sit next to me during the filming of an episode.

There were 1,424 almonds in the jar.

@BoostLacrosse guessed 1,423.

Close but no cigar.

Luckily, Travis gave me another chance to invest later and I grabbed it. And I’m sure @BoostLacrosse won’t let the next big opportunity slip away, either. The almond jar always gets refilled, and when it does, you try again.

I learned from my mistake and was lucky enough to go on to become part of a small group of “super angels,” men and women with personal brand awareness, like Kevin Rose, Chris Sacca, and Jason Calacanis, looking for opportunities to invest. I later made some nice investments in companies like Wildfire and Birchbox, and eventually in late 2013 I started a venture fund with Stephen Ross, Matt Higgins, and my brother called VaynerRSE, a $20 million seed fund that invests in early-stage Internet media companies. By the time you’re reading this I’ll have another one called Vayner Capital, which is a later-stage venture fund.

I’ve been watching and learning, and I think we’re living in interesting times. I see a lot of young companies going for the investments, and then instead of building up their business they spend all their time working toward the next round of funding. There seems to be a disturbing lack of patience and scrappiness out there in investment land, to the point I’ve changed the way I consider businesses. In fact, I’d go so far as to advise a lot of businesses to reconsider going for the VC money. It’s useful, to be sure, but I think it can make people lazy. The company whose founders have made great things happen on a shoestring and spent every dime and drop of sweat on building the best product they can before reaching out for VC dollars—that’s the company I’ve got my eye on.

What should I focus on with the companies that I invest in?

You’ve said that sometimes you invest in horses (companies) and sometimes in the jockeys (founders). What do you look for in each?

What’s your stance on investing in competitive companies?

You talk a lot about upcoming companies and predicting their success. Where and how do you find these companies?

What usually prompts you to walk away from great opportunities?

How do you balance risk and reward?

Does instability with China and the macroeconomic environment affect how you see the world?

How beneficial do you think patents are in being able to set a start-up apart from the competition?

Why don’t you invest in space, biotech, or life sciences?

How does geography affect your investment decisions? Is where founders or their businesses are located important to you?

Will you ever play in syndicate platforms like CircleUp or AngelList in the future?

What should companies expect from their investors at each stage of investment?

Should founders always be the ones that end up running their company when and if they reach a billion-dollar valuation?

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