At the time I was working in the Vimeo office (around 2009) and we were jammed into the back corner of the College Humor office. We had to be quiet most of the time because CH was recording their new MTV show. In between takes of taser wars and them filling up Rickys office with Chuck-E-Cheese balls, we managed to get work done on the new HD embed, but most of the time we just filmed funny videos and goofed off.

That day Gary had stopped over to see Ricky and Josh, the founders of CH, and I happened to see him sitting alone in the conference room.

“This is your chance Zerby, go pitch him on what you’ve been working on”.

I was working on Flavors.me, a new website builder that created instant personal websites from API data from Instagram, Facebook, Flickr, Twitter. We were ready to launch the beta, and I wanted to show Gary.

Flavors.me original demo video

My internal dialogue was racing as I stood right outside the door.

“Don’t do it dude, you’re gonna look like an idiot, what if it throws an error, what if he steals the idea, what if he laughs you out of the room, what if you trip and fall and break your nose on your way in?”

Eventually I said screw it and walked in.

“Gary can I show you something?”

“Sure dude!”

And the next 10 minutes were a blur. I showed him that you could create a personally branded website using nothing but your social data, in under 60 seconds. I didn’t blab on about the vision of the company, the market size, the business plan, the exit strategy…I just walked in and showed him how anyone can create a beautiful personal website in 60 seconds.

He got it right away and started talking Godaddy partnership, selling domains, upsells, downsells, future of identity, etc…and he said he was IN and wanted to invest.

I shook his hand and walked out on cloud nine. I ran outside and called my wife Marisa and told her we’re gonna be millionaires and about how Vary Gee wants to invest, and half a dozen other rambling sentences.

I had pushed through the fear and did it.

Then I screwed it all up…

It turns out Gary wanted a small amount of equity in exchange for doing all the marketing through his new firm Vaynermedia. Looking at that now you’d think it was a no brainer. 1% in exchange for Gary personally marketing your product to millions upon millions of his audience (who were all in our market)?? What idiot would say no to that…

“Hey Gary, I don’t think I can do that deal, but would love to talk about integrating Corkd’s API”

🤦‍♂️

Let me explain why I came to this ridiculous conclusion. We needed money, not marketing, to hire developers and support staff. And besides, Gary was the “Wine Guy” with a new marketing book called “Crush It”, could we really trust him to deliver?

Gary went on to become one of the top marketers in the world, and we continued to slog along raising money.

Here are 3 lessons I pulled from this experience:

Don’t be afraid to pitch anyone at anytime. If you believe in the product and you know it’s an amazing opportunity for them as an investor or customer, take your shot.
If you can’t show the value of the product and the problem it solves in under 60 seconds, you’ve lost the pitch.
Checks aren’t everything. We’ve raised big money from Pharma CEO’s who added no value other than cash, and we’ve raised small money from Angel investors who have given us WAY more value than they invested. Like Gary’s offer, sometimes the real value is in the network and influence of the investor.

Till next time,

Jack

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