There have been many times in my career where I just couldn't see it...

One day at Vimeo, I looked over my monitor and saw Zach Hoeken (nickname Iowa), one of our engineers working on some sort of CAD robot drawing.

I remember being pissed because he was supposed to be coding up new mockups I had for the video page.

I walked over and said flippantly, "yo what the heck are you working on?"

"A printer that can print out other printers"

"Oh ok cool yea I don't understand what you're saying, but when do you think you can have these new changes live?"

I was confused and unsure why anyone would spend so much of their time working on such a strange hobby.

Turns out Zach was going to Brooklyn every day to work on some of the very first 3d printers with a guy named Bre Pettis.

While I missed the vision...Jake Lodwick (cofounder of Vimeo) invested, and Zach and Bre went on to build MakerBot, selling it for $400m.

I remember Jake coming to my desk and talking about this small blogging site that his friend David was building.

He told me he had put a small amount of money in and thought it would change the blogging world.

I brushed it off and thought no one could beat Blogger.com or Wordpress, they were too big.

While I missed the vision, Jake invested, David Karp went on to build Tumblr, and eventually sold it to Yahoo for $1b.

I remember talking to Jake a few weeks later about a sports site his cousin was building.

ESPN has cornered that market I thought, there's no way a small site is going to make a dent in the sports world, it's just too hard.

While I missed the vision, Jake invested, and Bryan Goldberg went on to build Bleacher Report, selling it for $175m.

I remember working across the Vimeo office with Josh Mohrer (nickname Jay-Mo), who was running Busted Tees at the time.

He would bust on us at Vimeo all the time because we weren't making any money, and Busted Tees was raking in millions. (Ouch he was right…)

He was a fantastic operator and keen businessman, and when I found out he had joined a black cab mobile app after he left Busted Tees, I thought it was a shame to waste all that talent.

While I missed the vision, Josh went on to be one of the early employees at Uber, growing Uber's New York area business to $3bn in annual revenue.

I remember the day my business partner Jonathan told me that his long time mentor at IAC John Foley, was starting a "bike company".

John was an early investor in two of our companies, and I knew he was really sharp, but I couldn't for the life of me understand why he would leave tech and start a spin company.

While I brushed it off and didn't see the vision...John Foley went on to build Peleton, which had revenues of $1.06b in 2020.

I learned later on in my career to NEVER underestimate ANYONE.

Reading the stories of great entrepreneurs, almost no one saw them coming.

From Steve Jobs and Woz building phone hacking boxes out of their garage, to Phil Knight selling shoes made from a waffle iron out of the trunk of his car.

Any one of us could easily look at those visionaries and say "I don't see it".

So the next time you’re pitched an idea, give them the benefit of the doubt, encourage them, because you never know where their vision will take them...and the world!

BTW, If you're looking to raise money for your next big vision, I just launched my new live workshop on pitch deck design.

An in-depth 2hr training on how to craft pitch decks that impress investors & close deals. Learn the same techniques I've used to design decks that raised $250m+.

http://designfordecks.com

Reply back to this email and I'll give you a $100 off coupon code, as my guest.

Till next time!

Jack

Startup Stories from the Trenches

Can't see the forest for the trees.