companies I coulda woulda shoulda invested in but didn& #39;t .. (aka the "greatest misses")

@calm - I am friends w/ @tewy & @acton and think they are ballers. probably could& #39;ve invested at seed round (~$5M valuation). Now worth $1B+ easily. 200x+ return

didn& #39;t invest because I didn& #39;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& #39;t fully understand it (still don& #39;t)....But I thought he was really clever (I remember a story about a https://abs.twimg.com/emoji/v2/... draggable="false" alt="🍆" title="Aubergine" aria-label="Emoji: Aubergine"> 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& #39;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 minhttps://abs.twimg.com/emoji/v2/... draggable="false" alt="🤦‍♂️" title="Mann schlägt sich die Hand vors Gesicht" aria-label="Emoji: Mann schlägt sich die Hand vors Gesicht">

@loom - buds with @_shahedk, had him at my mastermind to help think through loom. could& #39;ve invested early on (~$5M cap?) now worth $250M+.

Didn& #39;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& #39;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& #39;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