I knew nothing when I started a media company (The Hustle). Nothing! Had never worked in the industry, didn’t know what CPM meant, didn’t know a single person who worked in the field.
So I reached out to a bunch of successful media founders, hoping they’d guide me.
But how on earth do you find someone super successful to give you, a piss ant with next to nothing to give in exchange, some good life changing advice?
I ended up finding this guy, Kevin Ryan, who, I think, is a billionaire. He started Gilt, MongoDB, and Business Insider.
I found his email and sent him a note asking to talk. Zero reply. So I kept following up with updates on the business and my life. Revenue growth, issues in the business, how I was feeling about it all. Almost like an investor update, but written in an entertaining way.
After doing this for months, I finally got a reply saying he was available in NYC for a very quick meeting
“What a coincidence,” I told him, "I happen to be in NYC, let’s do it!”
I was in SF at the time. And obviously didn’t have a trip planned to NYC but I booked the next flight anyway.
And it worked! Kevin met with me and in our short meeting gave me very needle moving advice that had a huge impact on my business and life.
This habit of googling cool people and then cold emailing them, it likely was the #1 most impactful thing on my career. I’d cold email them, get no reply, then follow up with business/life updates until I got a reply. I made the emails fun to read and people would get invested and think “ok, this guy might be legit, I’ll give him a chance.”
That’s how I met my Hampton cofounder Joe - I googled something generic like “fast growing media startups” and then I asked to hang out. We ended up becoming close buddies, after 6 years of being friends, cofounders.
In fact, this is how I met Shaan!
Nowadays, Twitter makes this much easier. Use the same profile picture across gmail, social, etc…post a ton, reply a ton, and people get to know you.
Moral of the story - nobody is out of reach. Make the ask…and follow up, follow up, follow up!