Halloween is always a surreal holiday for me, because on Halloween 2006, we sold @reddit to Conde Nast... the deal was months in the making and I wish I'd had more advisors around the table giving me more perspective on the sale. I thought I was getting away with something...

because for 16mos worth of work, I was getting more money than my parents had made their entire working lives. And there were lots of things about management, team-building, leadership, that I desperately needed to learn (one reason why @sevensevensix offers coaching from day1)

But tbh, my mom's illness weighed on me the most. She was diagnosed with terminal brain cancer just a couple months into founding the company, so the idea of rewarding her life-long unflagging confidence in me with a $10M exit was tremendously appealing.

I wish I'd had an investor tell me there were other options (like raising a Series A!) and there would be a path to much greater things given how fast the audience was growing at a time when our engineers had basically stopped working on the product

All these mistakes are just lessons, and opportunities for growth, and I hope to do a better job guiding the next Alexis Ohanian, 22 and wide-eyed, who is running a startup that I hope will make MUCH better decisions than I did.

Every single company I back and every single CEO I mentor, gives me a chance at a little redemption.

I'm going to do a better job publishing these things, too, because we're only investing in ~30 companies a fund and there's no reason for me to be greedy with these lessons.

And if you want a fun counterfactual, in 2006, I also managed to get in front of the leadership of WPNI (Washpo/NewsweekInteractive) and they did diligence on a potential acquisition of Reddit but didn't want to compete with Conde Nast's offer, so they passed.