companies I coulda woulda shoulda invested in but didn't .. (aka the "greatest misses")

@calm - I am friends w/ @tewy & @acton and think they are ballers. probably could've invested at seed round (~$5M valuation). Now worth $1B+ easily. 200x+ return

didn't invest because I didn't consider myself an investor at the time

@clearbit - friendly w/ @maccaw - told me about it over lunch.

Seemed like a decent idea but I didn't fully understand it (still don't)....But I thought he was really clever (I remember a story about a detection thing he built)

Shoulda asked to invest. now worth $250M+

@ApplyBoard I asked a 13 year old ( @SoroushG_ ) to scout deals for me. He intro'd me to @MartinBasiri . Loved the concept of helping international students apply to US colleges (I finished highschool in beijing)

Woulda been $25k at $5M. Now worth $1B+. Chickened out last min

@loom - buds with @_shahedk, had him at my mastermind to help think through loom. could've invested early on (~$5M cap?) now worth $250M+.

Didn't see it being that big and as much as I loved shahed - founder seemed young/likely to trip over their own feet. wrong!

@TheSocialChain - hired @SteveBartlettSC when he was like 20? 21? thought he was a future star.

Should've handed him his 1st check when he wanted to go do SC fulltime. Best way to show you believe in someone.

Started as a meme ad agency.. now a $200M+ public company.

ok that's about as much regret as I can handle in one sitting. will add more to the thread later.

biggest takeaway: shoulda invested in my friends