My Job: Never Underestimate Anyone


Anyone can go from a nobody to a somebody overnight — so my job as an angel investor is to never underestimate anyone.

Truth is, people starting their careers often look awkward, are broke, and they seem desperate.

You know why I know this? Because that’s how I looked when I started Silicon Alley Reporter back in ‘95. I was so broke that I lived in Brooklyn when it wasn’t cool. I had no money, so I printed the first issue of my zine at a photocopy store.

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Back then I would walk my magazine (the 16-page photocopy I delusively called a magazine) to the offices of Razorfish,, DoubleClick, Flatiron Partners, Pseudo, and SiteSpecific.

When I brought in the stack of magazines — carried on a cheap luggage cart — people would ask me, “who is the editor or CEO of Silicon Alley Reporter?”

“Me!” I would reply as I untied the bungee cords and handed the receptionist 25 issues.

At the time I had no idea folks were laughing at me and considered me somewhere between a pest and a joke. However, some folks didn’t sleep on me. Some folks noticed the hustle behind the dorky kid with the photocopied magazines who couldn’t afford to UPS them to receptionists.

Fred Wilson and Jerry Colonna threw their support behind the magazine, as did Jeff Dachis and Craig Kanarick at Razorfish. One group made fun of me, while the other bought ads and would invite me into their offices and share with me what they were doing.

I’m an angel investor in Craig’s, as well as Jeff Dachis’ new startup — which is going to debut at the LAUNCH Festival in 30 days. Oh yeah, Fred Wilson is giving a keynote at the festival, and his wife Joanne Wilson — who is a prolific angel investor — is going to be a judge.

Jerry Colonna is a favorite guest on my podcast This Week in Startups.

All of these people have one thing in common: they didn’t underestimate me when I was a dork. When I was broke. When I needed help.

Now I’m forever loyal to them. I would do anything for those five people, and I actually try and figure out how I can help them every chance I get … almost 20 years later.

Today I take the same attitude. Someone asked if they could pitch me in the hallway at WeWork while I was in between tapings of my podcast.

“I don’t have time right now,” I said … before catching myself and saying “but you can pitch me while I’m taking a leak!”

The person followed me into the bathroom and pitched me … while I was taking a leak. That’s my job, never saying no to someone who is awkward and who wants my time. That person could be the next Travis, Zuckerberg, or Sophia Amoruso — I better not say no!

Never. Underestimate. Anyone.

We’re all awkward at the start, but where you start is soon forgotten. Fight the good fight, support the new.

best @jason

Epilogue: Even to this day I have people underestimating me. I told one of them last week, “You know what, this is probably going to be the last year you could actually do me a favor — I’m kind of bummed you’re not jumping at the chance to support me!” They fumbled around an explanation and I just smiled, knowing how true it was.

PS – LAUNCH Festival Hackathon is about to fill up.

PPS – Check out the list of speakers at LAUNCH Festival — content is full!

PPPS – If you are hiring, buy a $3,000 table for three days at the LAUNCH Festival job fair; it’s the best place to find talent (10,000 folks coming!).



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